KR20140117003A - A composition comprising the phenolic compounds isolated from extract of Carthamus tinctorious seeds as an active ingredient for skin whitening - Google Patents
A composition comprising the phenolic compounds isolated from extract of Carthamus tinctorious seeds as an active ingredient for skin whitening Download PDFInfo
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- KR20140117003A KR20140117003A KR1020130031528A KR20130031528A KR20140117003A KR 20140117003 A KR20140117003 A KR 20140117003A KR 1020130031528 A KR1020130031528 A KR 1020130031528A KR 20130031528 A KR20130031528 A KR 20130031528A KR 20140117003 A KR20140117003 A KR 20140117003A
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- Prior art keywords
- acid
- composition
- extract
- lotion
- active ingredient
- Prior art date
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Abstract
Description
본 발명은 홍화자 추출물로부터 분리된 화합물을 유효성분으로 함유하는 미백용 조성물을 제공한다.The present invention provides a whitening composition comprising, as an active ingredient, a compound isolated from a safflower extract.
[문헌 1] Yu YG, Jeong MS, Choe JY, Kim JY. A study on Whitening Effect of Ephedra sinica extracts. Journal of the Korean Society of Design Culture. 31(2): 153-159 (2005)[Document 1] Yu YG, Jeong MS, Choe JY, Kim JY. A study on Whitening Effect of Ephedra sinica extracts. Journal of the Korean Society of Design Culture. 31 (2): 153-159 (2005)
[문헌 2] Jeong MH, Kim SS, Kim JS, Lee HJ, Chio GP, Lee HY. Jour. Korean For. Soc. 99(4): 470-478 (2005)[Reference 2] Jeong MH, Kim SS, Kim JS, Lee HJ, Chio GP, Lee HY. Jour. Korean For. Soc . 99 (4): 470-478 (2005)
[문헌 3] Bell AA, Weeler MH. Biosynthesis and function of fungal melanin. Annual Review Phytopathology. 24: 411-451 (1986) [Document 3] Bell AA, Weeler MH. Biosynthesis and function of fungal melanin. Annual Review Phytopathology. 24: 411-451 (1986)
[문헌 4] Lerner AB, Fitzpatrick TB. Biochemistry of melanin formation. Physiological Review. 30: 91-126 (1950)[Literature 4] Lerner AB, Fitzpatrick TB. Biochemistry of melanin formation. Physiological Review. 30: 91-126 (1950)
[문헌 5] Chen JS, Wei C, Marxhall MR. Inhibition mechanism of Koji acid on polyphenol oxidase. Journal of Agricyltural and Food Chemistry. 58: 79-110 (1991)[Literature 5] Chen JS, Wei C, Marxhall MR. Inhibition mechanism of koji acid on polyphenol oxidase. Journal of Agricutural and Food Chemistry. 58: 79-110 (1991)
[문헌 6] Urabe K, Aroca P, Tsukamoto K, Mascagna D, Paulumbo A, Prota G and Hering VJ. The inherent cytotoxicty of melanin precursors. 1221: 272-278 (1994) [Literature 6] Urabe K, Aroca P, Tsukamoto K, Mascagna D, Paulumbo A, Prota G and Hering VJ. The inherent cytotoxic effect of melanin precursors. 1221: 272-278 (1994)
[문헌 7] Hearing VJ, Tsukamoto K. Enzymatic control of pigmentation in mammals. FASEB J. 5(14): 2902-2909 (1991)[Literature 7] Hearing VJ, Tsukamoto K. Enzymatic control of pigmentation in mammals. FASEB J. 5 (14): 2902-2909 (1991)
[문헌 8] Jimenez-Cervantes C, Solano F, Kobayashi T, Urabe K, hearing V, Lezano J, Garcia-Gorreni JC. A new enzymatic function in the melanogenic pathway. J. Biol. Chem. 269(27): 17993-18000 (1994) [Literature 8] Jimenez-Cervantes C, Solano F, Kobayashi T, Urabe K, hearing V, Lezano J, Garcia-Gorreni JC. A new enzymatic function in the melanogenic pathway. J. Biol. Chem. 269 (27): 17993-18000 (1994)
[문헌 9] Maeda K, Fukuda M. Arbutin: mechanism of its depigmenting action in human melanocyte culture. J. Phamacol. Exp. Ther. 276: 765-769 (1996)[9] Maeda K, Fukuda M. Arbutin: mechanism of its depigmenting action in human melanocyte culture. J. Phamacol. Exp. Ther. 276: 765-769 (1996)
[문헌 10] Battaini GE, Monzani L, Casella L, Santagostini R, Pagliarin. Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. J. Biol. Inorg. Chem. 5: 262-268 (2000)[Literature 10] Battaini GE, Monzani L, Casella L, Santagostini R, Pagliarin. Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. J. Biol. Inorg. Chem. 5: 262-268 (2000)
[문헌 11] Chun HJ, Chli WH, Baek SH, Woo WH. Effect of quercetin on melanogenesis in melan-a melanocyte cells. Korean J. Pharmacogn. 33: 245-251 (2002). [Document 11] Chun HJ, Chli WH, Baek SH, Woo WH. Effect of quercetin on melanogenesis in melan-a melanocyte cells. Korean J. Pharmacogn. 33: 245-251 (2002).
[문헌 12] Curto EV, Kwong C, Hermersdorfer H, Glatt C, Santis V, Virador VJ and Dooley TP. Inhibitions of mammalian melanocytes tyrosinase: In vitro comparisons of alkyl esters of gentiic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663-672 (1999 )[Document 12] Curto EV, Kwong C, Hermersdorfer H, Glatt C, Santis V, Virador VJ and Dooley TP. Inhibitions of mammalian melanocytes tyrosinase: In vitro comparisons of alkyl esters of gentiic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663-672 (1999)
[문헌 13] Seo BI, Lee ES, Park JH, Kim SC, Byun BH, Choi HY. A efficacy of Korean and Chinese Carthami Semen on analgesic effect , anti - inflammation and arthritis. Kor. J. Herbology. 16(1): 1-10 (2001) [Literature 13] Seo BI, Lee ES, Park JH, Kim SC, Byun BH, Choi HY. A efficacy of Korean and Chinese Carthami Semen on analgesic effect, anti-inflammation and arthritis. Kor. J. Herbology. 16 (1): 1-10 (2001)
[문헌 14] Hur TY, Yun MY, Cho EH, Lee OJ, Kim KS, Cho NG. Clinical Study on Effect of Carthmi-Flos Herbal acupuncture therapy on Osteoarthritis in Knee Joint. The Journol of Korean Acupuncture & Moxibustion Society. 19(2): 189-200 (2002)[14] Hur TY, Yun MY, Cho EH, Lee OJ, Kim KS, Cho NG. Clinical Study on Effect of Carthmi-Flos Herbal Acupuncture Therapy on Osteoarthritis in Knee Joint. The Journol of Korean Acupuncture & Moxibustion Society. 19 (2): 189-200 (2002)
[문헌 15] Jang SJ, Lee CH, Yook TH. Effects of Laennec.N.HO (Hominis placenta. Cervi pontotrionum cornu . Carthami semen) aqua-acupuncture on the ovariectomized osteoporotic Rats. Korea Institute of Science and Technology Information. 19(1): 5-18 (1998) [Document 15] Jang SJ, Lee CH, Yook TH. Effects of Laennec.N.HO ( Hominis placenta. Cervi pontotrionum cornu . Carthami semen ) aqua-acupuncture on the ovariectomized osteoporotic Rats. Korea Institute of Science and Technology Information. 19 (1): 5-18 (1998)
[문헌 16] Seung KR, Jung KH. Effect of Carthamus tinctorius L. Semen on Endotoxin-induced Thrombosis in Rats. The journal of applied pharmacology. 9: 258-262 (2001)[Document 16] Seung KR, Jung KH. Effect of Carthamus Tinctorius L. Semen on Endotoxin-induced Thrombosis in Rats. The journal of applied pharmacology. 9: 258-262 (2001)
[문헌 17] Jung KW, Jeong CS, Jeong JS. Effect of Subfractions of Carthamus tinctorius L. Semen on the Lipid Peroxidation and Oxygen Free Radical Scavenging Enzyme Activities in CCI₄-induced Hepatotoxic Rats. J. Fd Hyg. Safety 14(2): 179-185 (1999)[Document 17] Jung KW, Jeong CS, Jeong JS. Effect of Subfractions of Carthamus tinctorius L. Semen on the Lipid Peroxidation and Oxygen Free Radical Scavenging Enzyme Activities in CCI4-induced Hepatotoxic Rats. J. Fd Hyg. Safety 14 (2): 179-185 (1999)
[문헌 18] Sakamura, A., T erayama, Y., Kawakat su, S., Ichihara, A. and Saito, H. Conjugated serotonins and phenolic constituent s in safflower seed (Carthamus tinctorius L.). A g ric . B iol . Chem ., 44, 2951 (1980).[18] Sakamura, A., Terayama, Y., Kawakata, S., Ichihara, A. and Saito, H. Conjugated serotonins and phenolic constituents in safflower seed ( Carthamus tinctorius L.). A g ric . B iol . Chem , ≪ / RTI > 44, 2951 (1980).
[문헌 19] Michikawa M, Lim KT, McLarnon JG, Kim SU:Oxygen radical-induced neurotoxicity in spinal cord neuron cultures. J. Neurosci Res. 37:62-70 (1994)[19] Michikawa M, Lim KT, McLarnon JG, Kim SU: Oxygen radical-induced neurotoxicity in spinal cord neuron cultures. J. Neurosci Res. 37: 62-70 (1994)
[문헌 20] Carmichael J, Degraff WG, Gadzar AF. 1987. Evaluation of a tetrazolium based semiautomated colorimetric assay: Assessment of chemosensitivity testing. Cancer Res 477: 936-942.[Literature 20] Carmichael J, Degraff WG, Gadzar AF. 1987. Evaluation of a tetrazolium based semiautomated colorimetric assay: Assessment of chemosensitivity testing. Cancer Res 477: 936-942.
[문헌 21] Yagi AT, Kanbara T, Morinobu N. The effect of tyrosinase inhibition for aloe. Planta Med. 3981: 517-519 (1986).
[21] Yagi AT, Kanbara T, Morinobu N. The effect of tyrosinase inhibition for aloe. Planta Med. 3981: 517-519 (1986).
급속한 산업화에 따른 환경오염으로 인해 오존층이 파괴되어 자외선 조사량이 증가하고 있다(Yu YG, Jeong MS, Choe JY, Kim JY. A study on Whitening Effect of Ephedra sinica extracts. Journal of the Korean Society of Design Culture. 31(2): 153-159 (2005)). 인간의 피부색은 내적, 외적 요인에 의해 달라지는데 그 중 피부색을 결정하는 근본적인 내적인자는 천연 피부 색소인 melanin이다(Jeong MH, Kim SS, Kim JS, Lee HJ, Chio GP, Lee HY. Jour. Korean For. Soc. 99(4): 470-478 (2005)). The ozone layer is destroyed due to environmental pollution caused by rapid industrialization, and ultraviolet radiation dose is increasing ( Yu YG, Jeong MS, Choe JY, Kim JY. A study on Whitening Effect of Ephedra sinica extracts. Journal of the Korean Society of Design Culture. 31 (2): 153-159 (2005) ) . Human skin color depends on internal and external factors. Among them, melanin, a natural skin pigment that determines the skin color, is a melanin ( Jeong MH, Kim SS, Kim JS, Lee HJ, Chio GP, Lee HY. Soc ., 99 (4): 470-478 (2005) ).
멜라닌(Melanin)은 자외선, 건조, 극한 온도 등에 대한 생존능력을 높여주고, 커피, 차, 담배 등의 품질을 향상시키나(Bell AA, Weeler MH. Biosynthesis and function of fungal melanin. Annual Review Phytopathology. 24: 411-451 (1986) Lerner AB, Fitzpatrick TB. Biochemistry of melanin formation. Physiological Review. 30: 91-126 (1950)), 과도한 멜라닌 합성은 인체에 기미, 주근깨, 피부반점을 형성하고 피부노화를 촉진하며 피부암 유발에 관여하는 것으로 알려져 있다(Chen JS, Wei C, Marxhall MR. Inhibition mechanism of Koji acid on polyphenol oxidase. Journal of Agricyltural and Food Chemistry. 58: 79-110 (1991) Urabe K, Aroca P, Tsukamoto K, Mascagna D, Paulumbo A, Prota G and Hering VJ. The inherent cytotoxicty of melanin precursors. 1221: 272-278 (1994)). 티로신(Tyrosine)으로부터 멜라닌의 생합성에서 가장 중요한 단계는 티로시나제(tyrosinase)의 촉매작용을 통하여 일어나는 초기 반응(Hearing VJ, Tsukamoto K. Enzymatic control of pigmentation in mammals. FASEB J. 5(14): 2902-2909 (1991))으로 티로신(tyrosine)의 히드록시(hydroxyl)기를 부착시켜 DOPA(3,4-dihydroxy phenylalanine)을 생성하는 기작이다(Jimenez-Cervantes C, Solano F, Kobayashi T, Urabe K, hearing V, Lezano J, Garcia-Gorreni JC. A new enzymatic function in the melanogenic pathway. J. Biol. Chem. 269(27): 17993-18000 (1994)). Melanin improves the survival ability of ultraviolet rays, drying, extreme temperatures, and improves the quality of coffee, tea, and tobacco ( Bell AA, Weeler MH, Biosynthesis and function of fungal melanin, Annual Review Phytopathology 24: 30: 91-126 (1950) ) , excessive melanin synthesis forms spots, freckles, skin spots in the body and promotes skin aging ( J), Wei C, Marxhall MR, Inhibition mechanism of koji acid on polyphenol oxidase, Journal of Agricutural and Food Chemistry 58: 79-110 (1991) Urabe K, Aroca P, Tsukamoto K , Mascagna D, Paulumbo A, Prota G and Hering V. The inherent cytotoxic effects of melanin precursors 1221: 272-278 (1994) ) . The most important step in the biosynthesis of melanin from tyrosine is the initial reaction that occurs through the catalysis of tyrosinase ( Hearing VJ, Tsukamoto K. Enzymatic control of pigmentation in mammals. FASEB J. 5 (14): 2902-2909 (1991)), were attached to an hydroxyl (hydroxyl) of tyrosine (tyrosine) is a mechanism for generating a DOPA (3,4-dihydroxy phenylalanine) ( Jimenez-Cervantes C, Solano F, Kobayashi T, Urabe K, hearing V, Lezano J, Garcia-Gorreni JC. A new enzymatic function in the melanogenic pathway. J. Biol. Chem. 269 (27): 17993-18000 (1994) ) .
따라서 이 반응의 억제를 통해 멜라닌 생합성을 억제 할 수 있다. 현재 미백제로 가장 많이 사용되는 아부틴(arbutin)은 L-티로신(tyrosine)과 경쟁적으로 작용하는 저해제이며(Maeda K, Fukuda M. Arbutin: mechanism of its depigmenting action in human melanocyte culture. J. Phamacol. Exp. Ther. 276: 765-769 (1996)), 아부틴(arbutin), 아스코르빈산 (ascorbic acid)는 티로시나제 (tyrosinase) 활성 부위의 구리이온(copper)를 킬레이팅 (chelating)하여 티로신(tyrosine)에서 DOPA로 그리고 DOPA에서 DOPA 퀴논(quinone)으로 진행되는 과정을 저해한다(Battaini GE, Monzani L, Casella L, Santagostini R, Pagliarin. Inhibition of the catecholase activity of biomimetic dinuclear copper complexes by kojic acid. J. Biol. Inorg. Chem. 5: 262-268 (2000)). 그러나 현재 의학계나 화장품업계에서는 피부 안전성, 제형 안정성 등의 문제로 제한된 양만 사용되고 있다(Chun HJ, Chli WH, Baek SH, Woo WH. Effect of quercetin on melanogenesis in melan-a melanocyte cells. Korean J. Pharmacogn. 33: 245-251 (2002) Curto EV, Kwong C, Hermersdorfer H, Glatt C, Santis V, Virador VJ and Dooley TP. Inhibitions of mammalian melanocytes tyrosinase: In vitro comparisons of alkyl esters of gentiic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663-672 (1999 )). 특히 천연 한방약용식물을 소재로 한 연구가 관심 받고 있다. Therefore, it is possible to inhibit melanin biosynthesis through inhibition of this reaction. Currently, the most commonly used whitening agent, arbutin, is an inhibitor that competes with L-tyrosine ( Maeda K, Fukuda M. Arbutin: mechanism of its depigmenting action in human melanocyte culture, J. Phamacol. .. Ther 276: 765-769 (1996 )), Abu tin (arbutin), ascorbic acid (ascorbic acid) is a tyrosinase (tyrosinase) the copper ion (copper) of the active site chelating (chelating) to tyrosine (tyrosine) and in inhibiting the process proceeds to DOPA quinone (quinone) as in DOPA and DOPA (Battaini GE, Monzani L, L Casella, Santagostini R, Pagliarin. inhibition of the activity of biomimetic catecholase dinuclear copper complexes by kojic acid. J. Biol Inorg. Chem. 5: 262-268 (2000) ) . However, in the current medical and cosmetic industries, only limited amounts of skin safety and formulation stability have been used ( Chun HJ, Chli WH, Baek SH, Woo WH. 33: 245-251 (2002) Curto EV, Kwong C, Hermersdorfer H, Glatt C, Santis V, Virador VJ and Dooley TP. Inhibitions of mammalian melanocytes tyrosinase: In vitro Comparisons of alkyl esters of gentiic acid with other putative inhibitors. Biochem. Pharmacol. 57: 663-672 (1999) ). In particular, studies using natural herbal medicinal plants have been attracting interest.
피부의 색조를 결정하는 주요한 인자인 melanin은 표피 기저층의 melanocyte라고 불리는 색소세포내의 melanosome에서 생합성 된다. 멜라닌을 합성하는데 있어서의 출발물질은 아미노산의 일종인 tyrosine이다. 또한 tyrosinase는 피부 멜라닌 생성에 있어서 매우 중요한 역할을 하고 있으며, melanosome 내에서 tyrosine을 산화시켜 DOPA를 만드는 tyrosine hydroxylase로, DOPA를 산화시켜 DOPA quinone을 만드는 DOPA oxidase로서 작용하여 멜라닌 중합체를 합성하는데 중요한 효소로 작용한다. Melanin, a key determinant of skin tone, is biosynthesized in melanosomes in pigmented cells called melanocytes in the epidermal basal layer. The starting material for the synthesis of melanin is tyrosine, an amino acid. Tyrosinase plays an important role in the formation of melanin in the skin, tyrosine hydroxylase which oxidizes tyrosine in the melanosome to form DOPA, which acts as a DOPA oxidase which oxidizes DOPA to form DOPA quinone and is an important enzyme for synthesizing melanin polymer .
홍화자 (Carthamus tinctorius L.)는 홍화의 씨로 잇꽃의 종자가 성숙한 여름철에 채취하고 볕에 건조하여 약제로 쓰는데, 성질이 따뜻하고 맛이 달다([Seo BI, Lee ES, Park JH, Kim SC, Byun BH, Choi HY. A efficacy of Korean and Chinese Carthami Semen on analgesic effect , anti - inflammation and arthritis. Kor. J. Herbology. 16(1): 1-10 (2001) Hur TY, Yun MY, Cho EH, Lee OJ, Kim KS, Cho NG. Clinical Study on Effect of Carthmi-Flos Herbal acupuncture therapy on Osteoarthritis in Knee Joint. The Journol of Korean Acupuncture & Moxibustion Society. 19(2): 189-200 (2002)). 또한 민간에서는 홍화자가 골절에 효과가 있다고 알려져 있고, 개나 닭의 골절치료에 특효를 보았다는 기록이 전해지고 있어 홍화꽃과 달리 홍화씨는 이혈약의 작용이외에 골혈성작용이 있는 것을 거론되고 있으나, 홍화자에 대한 한방의 기록은 홍화의 약능과 같은 이혈작용에 관한 것뿐이며, 홍화자가 골절질환에 유효하다는 한방고전문헌은 존재하지 않는다(Jang SJ, Lee CH, Yook TH. Effects of Laennec.N.HO (Hominis placenta. Cervi pontotrionum cornu . Carthami semen) aqua-acupuncture on the ovariectomized osteoporotic Rats. Korea Institute of Science and Technology Information. 19(1): 5-18 (1998)). Carthamus tinctorius L.) is a seed of safflower. Seed of the safflower is harvested in the mature summer season and dried in the sun to be used as a medicament. It is warm and tasty in its nature. ( Seo BI, Lee JS, Kim SC, Byun BH, Choi HY. A efficacy of Korean and Chinese Carthami Semen on analgesic effect, anti-inflammation and arthritis. Kor. J. Herbology. Hur TY, Yun MY, Cho EH, Lee OJ, Kim KS, Cho NG. Clinical Study on Effect of Carthmi-Flos Herbal Acupuncture Therapy on Osteoarthritis in Knee Joint. The Journol of Korean Acupuncture & Moxibustion Society. 19 (2): 189-200 (2002) ) . In addition, it has been reported that safflower is effective for fracture in the private sector, and it has been reported that it has a special effect on the treatment of dog or chicken fracture. Unlike safflower flower, safflower seed is said to have a hemorrhagic action in addition to the action of a hemicycle drug. History of Herbal about is only about yihyeol will act as yakneung of safflower, Oriental classical literature honghwaja is that effective fracture disease does not exist (Jang SJ, Lee CH, Yook TH. effects of Laennec.N.HO (hominis placenta. Cervi pontotrionum cornu . Carthami semen ) aqua-acupuncture on the ovariectomized osteoporotic Rats. Korea Institute of Science and Technology Information. 19 (1): 5-18 (1998) ) .
그리고 최근 관상 동맥 확장 및 혈압을 낮추는 작용이 있으며 고콜레스테롤혈증을 향상시키고 혈전을 치료하는 효과 있다고 보고된바 있고(Seung KR, Jung KH. Effect of Carthamus tinctorius L. Semen on Endotoxin-induced Thrombosis in Rats. The journal of applied pharmacology. 9: 258-262 (2001)) 골절 및 골다공증 의 예방제로 사용되고 있다(Jung KW, Jeong CS, Jeong JS. Effect of Subfractions of Carthamus tinctorius L. Semen on the Lipid Peroxidation and Oxygen Free Radical Scavenging Enzyme Activities in CCI₄-induced Hepatotoxic Rats. J. Fd Hyg. Safety 14(2): 179-185 (1999)). Recently, it has been reported that coronary artery dilatation and lowering of blood pressure have been shown to be effective in improving hypercholesterolemia and treating thrombosis ( Seung KR, Jung KH. Effect of Carthamus Tinctorius L. Semen on Endotoxin-induced Thrombosis in Rats. The journal of applied pharmacology. 9: 258-262 (2001) ) and is used as a preventive agent for fractures and osteoporosis ( Jung KW, Jeong CS, Jeong JS. Effect of Subfractions of Carthamus tinctorius L. Semen on the Lipid Peroxidation and Oxygen Free Radical Scavenging Enzyme Activities in CCI4-induced Hepatotoxic Rats. J. Fd Hyg. Safety 14 (2): 179-185 (1999) ) .
따라서 본 연구에서는 멜라닌(melanin) 합성을 감소시키고 동시에 천연의 미백제를 찾기 위해 홍화자 추출물로부터 분리된 화합물을 유효성분으로 티로시나제(tyrosinase) 저해활성 및 멜라닌(melanin) 형성 저해효과, 멜라닌형성(melanogenesis) 관련 메카니즘을 규명하고자 한다.Therefore, in this study, the compounds isolated from Safflower extract were used as an effective ingredient to inhibit melanin synthesis and to find a natural whitening agent, and to inhibit tyrosinase inhibitory activity, melanin formation inhibitory effect, melanogenesis- Mechanism.
그러나, 지금까지 상기 문헌 어디에서도 홍화자 추출물로부터 분리된 화합물 추출물이 미백을 위한 조성물로서 사용가능하다고 교시되거나 기재된 바 없다.However, it has not been taught or described in the above-mentioned literatures that a compound extract isolated from a safflower extract can be used as a composition for whitening.
이에 본 발명자는 홍화자 추출물로부터 분리된 화합물은 티로시나제 (Tyrosinase) 효소 저해 활성, 멜라노마 세포생존율 증가, 멜라닌(melanin) 생합성 저해활성 등이 탁월함을 확인함으로써, 상기 조성물을 미백용 피부외용 약학조성물 또는 화장료 조성물로 유용하게 이용 가능함을 확인함으로써 본 발명을 완성하였다.
Accordingly, the inventors of the present invention found that the compound isolated from the safflower extract is excellent in tyrosinase enzyme inhibition activity, melanoma cell viability increase, melanin biosynthesis inhibition activity, and the like, The present invention has been completed.
상기 목적을 달성하기 위하여, 본 발명은 홍화자 추출물로부터 분리된 화합물을 유효성분으로 함유하는 미백용 피부 외용 약학조성물을 제공한다.In order to attain the above object, the present invention provides a whitening dermatological pharmaceutical composition comprising a compound isolated from a safflower extract as an active ingredient.
상기 추출물은 피부외용 약학조성물은 총 중량에 대하여 0.1 내지 50 중량%으로 포함함을 특징으로 한다.The extract of the present invention is characterized by containing 0.1 to 50% by weight based on the total weight of the dermatological pharmaceutical composition.
상기 약학 조성물은 크림, 젤, 패취, 분무제, 연고제, 경고제, 로션제, 리니멘트제, 파스타제 또는 카타플라스마제 제형을 포함한다. The pharmaceutical composition includes a cream, a gel, a patch, a spray, an ointment, an alarm, a lotion, a liniment, a pasta or a cataplasmal formulation.
또한, 상기 목적을 달성하기 위하여, 본 발명은 홍화자 추출물로부터 분리된 화합물을 유효성분으로 함유하는 미백용 화장료 조성물을 제공한다.In order to achieve the above object, the present invention provides a whitening cosmetic composition comprising a compound isolated from a safflower extract as an active ingredient.
또한, 상기 화장료 조성물은 화장수, 스킨, 로션, 영양로션, 영양크림, 마사지 크림, 에센스, 팩의 제형을 포함한다.In addition, the cosmetic composition includes formulations of lotion, skin, lotion, nutrition lotion, nutritional cream, massage cream, essence, and pack.
본원에서 정의되는 “홍화자 추출물로부터 분리된 화합물”은 아카세틴(acacetin), 코스모시인(cosmosiin), N-페룰로세로토닌(feruloylserotonin), 또는 N-(p-쿠마로일)세로토닌)로부터 선택된 화합물을 포함한다.As used herein, a " compound isolated from a safflower extract " refers to a compound selected from acacetin, cosmosiin, N -feruloylserotonin, or N - ( p -coumaroyl) serotonin .
본원에서 정의되는 추출물은 물, 에탄올, 메탄올, 프로판올, 부탄올, 아세톤, 에틸아세테이트, 헥산, 부틸렌글리콜, 프로필렌글리콜, 함수부틸렌글리콜, 함수프로필렌글리콜, 함수글리세린으로 구성된 그룹으로부터 선택된 하나 이상의 용매, 바람직하게는 물 및 에탄올, 가장 바람직하게는 60% 내지 90% 에탄올 가용 추출물을 포함한다. An extract as defined herein is one or more solvents selected from the group consisting of water, ethanol, methanol, propanol, butanol, acetone, ethyl acetate, hexane, butylene glycol, propylene glycol, hydrolyzed butylene glycol, Preferably water and ethanol, most preferably 60% to 90% ethanol soluble extract.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명의 생약 추출물 및 분리 화합물은 하기와 같이 수득될 수 있다. Herbal medicine extracts and separation compounds of the present invention can be obtained as follows.
예를 들어, 본 발명의 홍화씨를 분쇄하고 헥산, 에틸아세테이트, 클로로포름 등의 비극성용매로 추출하고 이를 반복수행하여 지방을 제거하는 제 1단계: 상기 단계에서 지방을 제거하고 남은 잔사에 이의 건조중량의 약 1 내지 30배 부피량, 바람직하게는 5 내지 15배에 달하는 부피의 물, 에탄올 및 메탄올 등과 같은 C₁내지 C₄의 저급알코올의 극성 용매 또는 이들의 혼합용매, 바람직하게는 50% 내지 90% 에탄올로, 약 50 내지 100℃, 바람직하게는 약 상온 내지 60℃에서 3시간 내지 12시간, 바람직하게는 4시간 내지 8시간, 동안 추출하여 얻어진 여액을 감압여과, 농축 및 동결 건조하여 홍화씨 조추출물을 수득하는 제 2단계; 상기 단계에서 얻은 조추출물을 상기 조추출물 중량의 약 0.05 내지 50배, 바람직하게는 0.5 내지 5배 부피 (v/w%)의 물을 가하여 현탁물을 제조하는 제 3단계; 상기 현탁물에 상기 현탁물 부피의 약 0.5 내지 20배 부피, 바람직하게는 1 내지 5배 부피 (v/w%)의 n-헥산, 헵탄, 메틸렌 클로라이드, 클로로포름 또는 에틸 아세테이트로부터 선택된 비극성용매, 바람직하게는 헥산 또는 에틸아세테이트 용매 및 부탄올 및 물을 가하여 순차적으로 분획과정을 반복수행하여 비극성 용매 가용분획물 및 극성용매 가용 분획물을 각각 수득하는 제 4단계; 상기 비극성용매 가용 분획물을 실리카겔 컬럼, 세파덱스 컬럼, 이온교환수지 등의 컬럼 크로마토그래피법 또는 재경화법 등의 정제법, 바람직하게는 전개용매 (클로포포름 및 물의 혼합용매를 극성을 올려 가면서 전개)를 이용한 실리카겔 컬럼및 재결정법을 이용한 정제과정을 반복수행하는 제 4단계 공정을 통하여 본 발명의 아카세틴(acacetin), 코스모시인(cosmosiin), N-페룰로세로토닌(feruloylserotonin), N-(p-쿠마로일)세로토닌) 등의 본 발명의 화합물을 분리가능하다.For example, the safflower seed of the present invention is pulverized, extracted with a nonpolar solvent such as hexane, ethyl acetate, chloroform and the like, and repeatedly performed to remove fat. The first step is to remove fat, A volume of water of about 1 to 30 times volume, preferably 5 to 15 times, a polar solvent of C 1 to C 4 lower alcohol such as ethanol and methanol, or a mixed solvent thereof, preferably 50% to 90% ethanol For about 3 hours to 12 hours, preferably for about 4 hours to 8 hours at about 50 to 100 캜, preferably about room temperature to 60 캜, is subjected to filtration under reduced pressure, concentration and lyophilization to obtain a safflower seed extract A second step of obtaining; A third step of adding the crude extract obtained in the above step to water by adding about 0.05 to 50 times, preferably 0.5 to 5 times the volume (v / w%) of the weight of the crude extract to the suspension; A non-polar solvent selected from n-hexane, heptane, methylene chloride, chloroform or ethyl acetate in an amount of about 0.5 to 20 times, preferably 1 to 5 times (v / w) A fourth step of sequentially obtaining a non-polar solvent-soluble fraction and a polar solvent-soluble fraction by sequentially repeating fractionation by adding hexane or ethyl acetate solvent, butanol and water; The non-polar solvent-soluble fraction is purified by a column chromatography method such as a silica gel column, a Sephadex column, or an ion exchange resin, or a purification method such as a re-curing method, preferably a developing solvent (developing a mixed solvent of chloroform and water with increasing polarity) (Paclitaxel), N - (feruloylserotonin), N - ( p - aminopyrimidine), and N - ( p - tocopherol) of the present invention through a fourth step of repeating the purification process using a silica gel column and a recrystallization method, Coumaroyl) serotonin), and the like.
또한, 본 발명의 생약들은 오랫동안 생약 및 식용으로 사용되어 오던 약재로서 이들로부터 추출된 본 발명의 생약 추출물 및 분리 화합물들은 독성 및 부작용 등의 문제가 없으며, 장기간 사용 시에도 안심하고 사용할 수 있다.
In addition, the herbal medicine of the present invention has been used for herbal medicine and food for a long time, and herbal medicine extracts and separation compounds of the present invention extracted therefrom have no problems such as toxicity and side effects, and can be used safely even when used for a long time.
상기 제조방법으로 제조된 화합물은 티로시나제 (Tyrosinase) 효소 저해 활성, 엘라스타제 (Elastase) 효소 저해활성, 세포 티로시나제 (celluar tyrosinase) 효소 저해활성, 멜라닌(melanin) 생합성 저해활성, 프로-콜라겐 (Pro-collagen) 생합성 저해 활성 등이 탁월함을 확인함으로써, 상기 조성물을 미백의 예방 및 치료용 피부외용 약학조성물 또는 화장료 조성물로 유용함을 확인하였다. The compound produced by the above-mentioned method can be used for inhibiting tyrosinase enzyme activity, Elastase enzyme inhibition activity, celluli tyrosinase enzyme inhibition activity, melanin biosynthesis inhibition activity, pro-collagen activity, collagen and biosynthesis inhibitory activity, it was confirmed that the composition is useful as an external dermatological pharmaceutical composition or cosmetic composition for preventing and treating whitening.
상기 화합물은 피부외용 약학조성물은 총 중량에 대하여 0.1 내지 50 중량%으로 포함함을 특징으로 한다.The above-mentioned compound is characterized in that it comprises 0.1 to 50% by weight based on the total weight of the dermatological pharmaceutical composition.
상기 약학 조성물은 크림, 젤, 패취, 분무제, 연고제, 경고제, 로션제, 리니멘트제, 파스타제 또는 카타플라스마제 제형을 포함한다. The pharmaceutical composition includes a cream, a gel, a patch, a spray, an ointment, an alarm, a lotion, a liniment, a pasta or a cataplasmal formulation.
또한, 상기 화장료 조성물은 화장수, 스킨, 로션, 영양로션, 영양크림, 마사지 크림, 에센스, 팩의 제형을 포함한다.In addition, the cosmetic composition includes formulations of lotion, skin, lotion, nutrition lotion, nutritional cream, massage cream, essence, and pack.
따라서 본원 발명은 하기 제조방법 및 상기 제조방법으로 수득된 화합물을 유효성분으로 함유하는 미백 치료 및 예방용 피부외용 약학 조성물 및 화장료 조성물을 제공한다.
Accordingly, the present invention provides a dermatological pharmaceutical composition and a cosmetic composition for whitening treatment and prevention comprising the following production method and a compound obtained by the production method as an active ingredient.
또한, 본 발명의 복분자 씨는 오랫동안 생약 및 식용으로 사용되어 오던 식품으로서 이들로부터 추출된 본 발명의 추출물 역시 독성 및 부작용 등의 문제가 없으며, 피부 첩포 시험에서 무자극 시료임이 입증되었으므로 장기간 사용 시에도 안심하고 사용할 수 있다.
In addition, the brambly seed of the present invention has been used for a long period of herbal medicine and food, and the extract of the present invention extracted therefrom has no problems such as toxicity and side effects and has proved to be a non-irritant sample in the skin patch test. Can be used with confidence.
본 발명의 화합물을 함유하는 피부외용 약학조성물은 크림, 젤, 패취, 분무제, 연고제, 경고제, 로션제, 리니멘트제, 파스타제 또는 카타플라스마제의 피부 외용제 형태의 약학조성물로 제조하여 사용할 수 있으나, 이에 한정하는 것은 아니다. The dermatological pharmaceutical composition containing the compound of the present invention can be used as a pharmaceutical composition in the form of external preparation for skin such as cream, gel, patch, spray, ointment, warning agent, lotion, liniment, pasta or cataplasm However, the present invention is not limited thereto.
본 발명의 화합물의 바람직한 투여량은 환자의 상태 및 체중, 질병의 정도, 약물형태, 투여경로 및 기간에 따라 다르지만, 당업자에 의해 적절하게 선택될 수 있다. 그러나 바람직한 효과를 위해서, 본 발명의 화합물은 1일 0.0001 내지 100 ㎎/㎏으로, 바람직하게는 0.001 내지 10 ㎎/㎏으로 투여하는 것이 좋다. 투여는 하루에 한번 투여할 수도 있고, 수회 나누어 투여할 수도 있다. 상기 투여량은 어떠한 면으로든 본 발명의 범위를 한정하는 것은 아니다. The preferred dosage of the compound of the present invention varies depending on the condition and the weight of the patient, the degree of disease, the type of drug, the route of administration and the period of time, but can be appropriately selected by those skilled in the art. However, for the desired effect, the compound of the present invention is preferably administered at 0.0001 to 100 mg / kg per day, preferably 0.001 to 10 mg / kg per day. The administration may be carried out once a day or divided into several times. The dose is not intended to limit the scope of the invention in any way.
본 발명의 화합물은 미백 방지 효과를 갖는 화장품 및 세안제 등에 다양하게 이용될 수 있다.The compounds of the present invention can be used variously in cosmetics and cleansers having a whitening-preventing effect.
본 조성물을 첨가할 수 있는 제품으로는, 예를 들어, 화장수, 스킨, 로션, 영양로션, 영양크림, 맛사지크림, 에센스, 팩 등과 같은 화장품류와 클렌징, 세안제, 비누, 트리트먼트, 미용액 등이 있다.Examples of products to which the present composition can be added include cosmetics such as lotion, skin, lotion, nutrition lotion, nutritional cream, massage cream, essence, pack, cleansing, cleanser, soap, have.
본 발명의 화장료는 수용성 비타민, 유용성 비타민, 고분자 펩티드, 고분자 다당, 스핑고 지질 및 해초 엑기스로 이루어진 군에서 선택된 조성물을 포함한다.The cosmetic composition of the present invention comprises a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high molecular weight peptides, polymeric polysaccharides, sphingolipids and seaweed extracts.
수용성 비타민으로서는 화장품에 배합 가능한 것이라면 어떠한 것이라도 되지만, 바람직하게는 비타민 B1, 비타민 B2, 비타민 B6, 피리독신, 염산피리독신, 비타민 B12, 판토텐산, 니코틴산, 니코틴산아미드, 엽산, 비타민 C, 비타민 H 등을 들 수 있으며, 그들의 염 (티아민염산염, 아스코르빈산나트륨염 등)이나 유도체 (아스코르빈산-2-인산나트륨염, 아스코르빈산-2-인산마그네슘염 등)도 본 발명에서 사용할 수 있는 수용성 비타민에 포함된다. 수용성 비타민은 미생물 변환법, 미생물의 배양물로부터의 정제법, 효소법 또는 화학 합성법 등의 통상의 방법에 의해 수득할 수 있다.The water-soluble vitamin is not particularly limited as long as it can be compounded in cosmetics. Preferably, vitamin B, vitamin B2, vitamin B6, pyridoxine, pyridoxine hydrochloride, vitamin B12, pantothenic acid, nicotinic acid, nicotinic acid amide, folic acid, vitamin C, And their salts (thiamine hydrochloride, sodium ascorbate, etc.) or derivatives (sodium ascorbic acid-2-phosphate, magnesium ascorbate-2-phosphate etc.) can also be added to water-soluble vitamins . The water-soluble vitamin can be obtained by a conventional method such as a microorganism conversion method, a purification method from a culture of a microorganism, an enzymatic method, or a chemical synthesis method.
유용성 비타민으로서는 화장품에 배합 가능한 것이라면 어떠한 것이라도 되지만, 바람직하게는 비타민 A, 카로틴, 비타민 D2, 비타민 D3, 비타민 E (d1-알파 토코페롤, d-알파 토코페롤, d-알파 토코페롤) 등을 들 수 있으며, 그들의 유도체 (팔미틴산아스코르빈, 스테아르산아스코르빈, 디팔미틴산아스코르빈, 아세트산 dl-알파 토코페롤, 니코틴산 dl-알파 토코페롤비타민 E, dl-판토테닐알코올, D-판토테닐알코올, 판토테닐에틸에테르 등) 등도 본 발명에서 사용되는 유용성 비타민에 포함된다. 유용성 비타민은 미생물 변환법, 미생물의 배양물로부터의 정제법, 효소 또는 화학 합성법 등의 통상의 방법에 의해 취득할 수 있다.Usable vitamins include vitamins such as vitamin A, carotene, vitamin D2, vitamin D3, vitamin E (d1-alpha tocopherol, d-alpha tocopherol, d-alpha tocopherol) , Derivatives thereof (such as palmitic acid ascorbin, stearic acid ascorbic acid, dipalmitic acid ascorbin, dl-alpha tocopherol acetic acid, dl-alpha tocopherol nicotinic acid vitamin E, dl-pantothenyl alcohol, D-pantothenyl alcohol, Ether, etc.) are also included in the usable vitamins used in the present invention. Usability Vitamins can be obtained by a conventional method such as a microorganism conversion method, a purification method from a culture of a microorganism, an enzyme or a chemical synthesis method.
고분자 펩티드로서는 화장품에 배합 가능한 것이라면 어떠한 것이라도 되지만, 바람직하게는 콜라겐, 가수 분해 콜라겐, 젤라틴, 엘라스틴, 가수 분해 엘라스틴, 케라틴 등을 들 수 있다. 고분자 펩티드는 미생물의 배양액으로부터의 정제법, 효소법 또는 화학 합성법 등의 통상의 방법에 의해 정제 취득할 수 있으며, 또는 통상 돼지나 소 등의 진피, 누에의 견섬유 등의 천연물로부터 정제하여 사용할 수 있다.The polymeric peptide may be any compound as long as it can be compounded in cosmetics, and examples thereof include collagen, hydrolyzed collagen, gelatin, elastin, hydrolyzed elastin, and keratin. The polymeric peptide can be obtained by a conventional method such as purification from a culture broth of a microorganism, an enzymatic method, or a chemical synthesis method, or it can be purified from natural products such as ducks such as pigs and cows and silk fiber of silkworms.
고분자 다당으로서는 화장품에 배합 가능한 것이라면 어떠한 것이라도 되지만, 바람직하게는 히드록시에틸셀룰로오스, 크산탄검, 히알루론산나트륨, 콘드로이틴 황산 또는 그 염 (나트륨염 등) 등을 들 수 있다. 예를 들어, 콘드로이틴 황산 또는 그 염 등은 통상 포유동물이나 어류로부터 정제하여 사용할 수 있다.The polymeric polysaccharide may be any compound as long as it can be incorporated in cosmetics, and examples thereof include hydroxyethyl cellulose, xanthan gum, sodium hyaluronate, chondroitin sulfate or a salt thereof (sodium salt, etc.). For example, chondroitin sulfate or a salt thereof can be usually purified from mammals or fish.
스핑고 지질로서는 화장품에 배합 가능한 것이라면 어떠한 것이라도 되지만, 바람직하게는 세라미드, 피토스핑고신, 스핑고당지질 등을 들 수 있다. 스핑고 지질은 통상 포유류, 어류, 패류, 효모 또는 식물 등으로부터 통상의 방법에 의해 정제하거나 화학 합성법에 의해 취득할 수 있다.Sphingo lipids may be any as long as they can be incorporated into cosmetics, and preferable examples thereof include ceramides, phytosphingosine and sphingoglycolipids. Sphingoid lipids can be purified from ordinary mammals, fish, shellfish, yeast or plants by conventional methods or can be obtained by chemical synthesis.
해초 엑기스로는 화장품에 배합 가능한 것이라면 어떠한 것이라도 되지만, 바람직하게는 갈조 엑기스, 홍조 엑기스, 녹조 엑기스 등을 들 수 있으며, 또, 이들의 해초 엑기스로부터 정제된 칼라기난, 아르긴산, 아르긴산나트륨, 아르긴산칼륨 등도 본 발명에서 사용되는 해초 엑기스에 포함된다. 해초 엑기스는 해초로부터 통상의 방법에 의해 정제하여 취득할 수 있다.The seaweed extract may be any of those which can be compounded in cosmetics. Preferably, the seaweed extract is selected from the group consisting of algae extract, red pepper extract, green algae extract and the like. Also, the algae extract may be colored guanine, arginic acid, Potassium alginate and the like are also included in the seaweed extract used in the present invention. Seaweed extract can be obtained from seaweed by a conventional method.
본 발명의 화장료에는 상기 필수 성분과 더불어 필요에 따라 통상 화장료에 배합되는 다른 성분을 배합해도 된다.The cosmetic of the present invention may be blended with other essential ingredients, if necessary, in combination with the essential ingredients.
이외에 첨가해도 되는 배합 성분으로서는 유지 성분, 보습제, 에몰리엔트제, 계면 활성제, 유기 및 무기 안료, 유기 분체, 자외선 흡수제, 방부제, 살균제, 산화 방지제, 식물 추출물, pH 조정제, 알콜, 색소, 향료, 혈행 촉진제, 냉감제, 제한(制汗)제, 정제수 등을 들 수 있다.Examples of the compounding ingredients that may be added include organic solvents such as a preservative component, a moisturizer, an emollient, a surfactant, an organic and inorganic pigment, an organic powder, an ultraviolet absorbent, a preservative, a bactericide, an antioxidant, a plant extract, a pH adjuster, A blood circulation accelerator, a cold agent, an antiperspirant agent, and purified water.
유지 성분으로서는 에스테르계 유지, 탄화수소계 유지, 실리콘계 유지, 불소계 유지, 동물 유지, 식물 유지 등을 들 수 있다.Examples of the oil retaining component include ester-based oil retaining, hydrocarbon-based oil retaining, silicone-based oil retaining, fluoric oil retaining, animal retention and plant retention.
에스테르계 유지로서는 트리2-에틸헥산산글리세릴, 2-에틸헥산산세틸, 미리스틴산이소프로필, 미리스틴산부틸, 팔미틴산이소프로필, 스테아르산에틸, 팔미틴산옥틸, 이소스테아르산이소세틸, 스테아르산부틸, 리놀레산에틸, 리놀레산이소프로필, 올레인산에틸, 미리스틴산이소세틸, 미리스틴산이소스테아릴, 팔미틴산이소스테아릴, 미리스틴산옥틸도데실, 이소스테아르산이소세틸, 세바신산디에틸, 아디핀산디이소프로필, 네오펜탄산이소알킬, 트리(카프릴, 카프린산)글리세릴, 트리2-에틸헥산산트리메틸롤프로판, 트리이소스테아르산트리메틸롤프로판, 테트라2-에틸헥산산펜타엘리슬리톨, 카프릴산세틸, 라우린산데실, 라우린산헥실, 미리스틴산데실, 미리스틴산미리스틸, 미리스틴산세틸, 스테아르산스테아릴, 올레인산데실, 리시노올레인산세틸, 라우린산이소스테아릴, 미리스틴산이소트리데실, 팔미틴산이소세틸, 스테아르산옥틸, 스테아르산이소세틸, 올레인산이소데실, 올레인산옥틸도데실, 리놀레산옥틸도데실, 이소스테아르산이소프로필, 2-에틸헥산산세토스테아릴, 2-에틸헥산산스테아릴, 이소스테아르산헥실, 디옥탄산에틸렌글리콜, 디올레인산에틸렌글리콜, 디카프린산프로필렌글리콜, 디(카프릴,카프린산)프로필렌글리콜, 디카프릴산프로필렌글리콜, 디카프린산네오펜틸글리콜, 디옥탄산네오펜틸글리콜, 트리카프릴산글리세릴, 트리운데실산글리세릴, 트리이소팔미틴산글리세릴, 트리이소스테아르산글리세릴, 네오펜탄산옥틸도데실, 옥탄산이소스테아릴, 이소노난산옥틸, 네오데칸산헥실데실, 네오데칸산옥틸도데실, 이소스테아르산이소세틸, 이소스테아르산이소스테아릴, 이소스테아르산옥틸데실, 폴리글리세린올레인산에스테르, 폴리글리세린이소스테아르산에스테르, 시트르산트리이소세틸, 시트르산트리이소알킬, 시트르산트리이소옥틸, 락트산라우릴, 락트산미리스틸, 락트산세틸, 락트산옥틸데실, 시트르산트리에틸, 시트르산아세틸트리에틸, 시트르산아세틸트리부틸, 시트르산트리옥틸, 말산디이소스테아릴, 히드록시스테아르산 2-에틸헥실, 숙신산디2-에틸헥실, 아디핀산디이소부틸, 세바신산디이소프로필, 세바신산디옥틸, 스테아르산콜레스테릴, 이소스테아르산콜레스테릴, 히드록시스테아르산콜레스테릴, 올레인산콜레스테릴, 올레인산디히드로콜레스테릴, 이소스테아르산피트스테릴, 올레인산피트스테릴, 12-스테알로일히드록시스테아르산이소세틸, 12-스테알로일히드록시스테아르산스테아릴, 12-스테알로일히드록시스테아르산이소스테아릴 등의 에스테르계 등을 들 수 있다.Examples of ester-based fats include glyceryl tri-2-ethylhexanoate, cetyl 2-ethylhexanoate, isopropyl myristate, butyl myristate, isopropyl palmitate, ethyl stearate, octyl palmitate, isostearyl isostearate, Butyl isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, isopropyl myristate, butyl, ethyl linoleate, isopropyl linoleate, ethyl oleate, isosilyl myristate, isostearic acid isostearyl, isostearyl palmitate, octyldodecyl myristate, Trimethylol propane, triisostearic acid trimethylol propane, tetra 2-ethylhexanoic acid pentaerythritol tetra (2-ethylhexanoate) , Decyl caprylate, decyl laurate, hexyl laurate, myristate decyl, myristyl myristate, myristine monoethyl stearate, stearyl stearate, decyl oleate, ricinoleic acid tri , Isostearyl stearate, isostearyl stearate, isodecyl stearate, octyldodecyl oleate, octyldodecyl linoleate, isopropyl isostearate, isopropyl stearate, isopropyl stearate, isopropyl stearate, -Hexyl stearate, stearyl ethylhexanoate, stearyl 2-ethylhexanoate, hexyl isostearate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicaprate, di (capryl, capric acid) propylene glycol, Propyleneglycol propionate, propyleneglycol propionate, dicaproic acid neopentyl glycol, dioctanoic acid neopentyl glycol, tricarboxylic acid glyceryl, triunsaturated glyceryl, triisopalmitic acid glyceryl, triisostearic acid glyceryl, neopentanoic acid octyldodecyl Octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, octanoic acid octanoate, Octyldecyl lactate, octyldecyl lactate, octyldecyl lactate, polyglycerin oleic acid ester, polyglycerin isostearic acid ester, triisocetyl citrate, triisobutyl citrate, triisooctyl citrate, lauryl lactate, myristyl lactate, But are not limited to, ethyl, acetyltriethyl citrate, acetyltributyl citrate, trioctyl citrate, diisostearyl malate, 2-ethylhexyl hydroxystearate, di-2-ethylhexyl succinate, diisobutyl adipate, diisopropyl sebacate, But are not limited to, dioctyl sebacate, stearic acid cholesteryl, isostearic acid cholesteryl, hydroxystearic acid cholesteryl, oleic acid cholesteryl, oleic acid dihydrocholesteryl, isostearic acid pitostearyl, Stearoyl hydroxystearic acid isostearyl, 12-stearoyl stearyl hydroxystearate, 12-stearo And monohydroxystearic acid and esters such as sostearyl.
탄화 수소계 유지로서는 스쿠알렌, 유동 파라핀, 알파-올레핀올리고머, 이소파라핀, 세레신, 파라핀, 유동 이소파라핀, 폴리부덴, 마이크로크리스탈린왁스, 와셀린 등의 탄화 수소계 유지 등을 들 수 있다.Examples of the hydrocarbon hydrocarbon-based fats include hydrocarbon fats and oils such as squalene, liquid paraffin, alpha-olefin oligomer, isoparaffin, ceresin, paraffin, floating isoparaffin, polybutene, microcrystalline wax and vaseline.
실리콘계 유지로서는 폴리메틸실리콘, 메틸페닐실리콘, 메틸시클로폴리실록산, 옥타메틸폴리실록산, 데카메틸폴리실록산, 도데카메틸시클로실록산, 디메틸실록산ㆍ메틸세틸옥시실록산 공중합체, 디메틸실록산ㆍ메틸스테알록시실록산 공중합체, 알킬 변성 실리콘유, 아미노 변성 실리콘유 등을 들 수 있다.Examples of silicone based oils include polymethyl silicone, methylphenyl silicone, methyl cyclopolysiloxane, octamethylpolysiloxane, decamethylpolysiloxane, dodecamethylcyclosiloxane, dimethylsiloxane-methylcetyloxysiloxane copolymer, dimethylsiloxane-methylstarchoxysiloxane copolymer, alkyl Modified silicone oils, and amino-modified silicone oils.
불소계 유지로서는 퍼플루오로폴리에테르 등을 들 수 있다.Examples of the fluorine-based oil include perfluoropolyether and the like.
동물 또는 식물 유지로서는 아보카도유, 아르몬드유, 올리브유, 참깨유, 쌀겨유, 새플라워유, 대두유, 옥수수유, 유채유, 행인(杏仁)유, 팜핵유, 팜유, 피마자유, 해바라기유, 포도종자유, 면실유, 야자유, 쿠쿠이너트유, 소맥배아유, 쌀 배아유, 시아버터, 월견초유, 마커데이미아너트유, 메도홈유, 난황유, 우지(牛脂), 마유, 밍크유, 오렌지라피유, 호호바유, 캔데리러왁스, 카르나바왁스, 액상 라놀린, 경화피마자유 등의 동물 또는 식물 유지를 들 수 있다.Examples of animal or vegetable oils include avocado oil, almond oil, olive oil, sesame oil, rice bran oil, new flower oil, soybean oil, corn oil, rape oil, apricot kernel oil, palm kernel oil, palm oil, castor oil, , Corn oil, palm oil, palm oil, cucumber nut oil, wheat germ oil, rice germ oil, shea butter, coltsfoot colostrum, marker daisy nut oil, mead home oil, egg oil, , Canned wax, carnauba wax, liquid lanolin, hardened castor oil, and the like.
보습제로서는 수용성 저분자 보습제, 지용성 분자 보습제, 수용성 고분자, 지용성 고분자 등을 들 수 있다.Examples of the moisturizing agent include water-soluble low-molecular moisturizing agents, oil-soluble molecular moisturizing agents, water-soluble polymers, and oil-soluble polymers.
수용성 저분자 보습제로서는 세린, 글루타민, 솔비톨, 만니톨, 피롤리돈-카르복실산나트륨, 글리세린, 프로필렌글리콜, 1,3-부틸렌글리콜, 에틸렌글리콜, 폴리에틸렌글리콜B(중합도 n = 2 이상), 폴리프로필렌글리콜(중합도 n = 2 이상), 폴리글리세린B(중합도 n = 2 이상), 락트산, 락트산염 등을 들 수 있다.Examples of the water-soluble low-molecular moisturizing agent include serine, glutamine, sorbitol, mannitol, sodium pyrrolidone-carboxylate, glycerin, propylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol B Glycol (polymerization degree n = 2 or more), polyglycerin B (polymerization degree n = 2 or more), lactic acid, lactic acid salt and the like.
지용성 저분자 보습제로서는 콜레스테롤, 콜레스테롤에스테르 등을 들 수 있다.Examples of the lipid-soluble low-molecular moisturizing agent include cholesterol and cholesterol ester.
수용성 고분자로서는 카르복시비닐폴리머, 폴리아스파라긴산염, 트라가칸트, 크산탄검, 메틸셀룰로오스, 히드록시메틸셀룰로오스, 히드록시에틸셀룰로오스, 히드록시프로필셀룰로오스, 카르복시메틸셀룰로오스, 수용성 키틴, 키토산, 덱스트린 등을 들 수 있다.Examples of the water-soluble polymer include carboxyvinyl polymer, polyaspartic acid, tragacanth, xanthan gum, methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, water-soluble chitin, chitosan, dextrin, etc. .
지용성 고분자로서는 폴리비닐피롤리돈ㆍ에이코센 공중합체, 폴리비닐피롤리돈ㆍ헥사데센 공중합체, 니트로셀룰로오스, 덱스트린지방산에스테르, 고분자 실리콘 등을 들 수 있다.Examples of the oil-soluble polymer include polyvinylpyrrolidone / eicosene copolymer, polyvinylpyrrolidone / hexadecene copolymer, nitrocellulose, dextrin fatty acid ester, and polymer silicone.
에몰리엔트제로서는 장쇄아실글루타민산콜레스테릴에스테르, 히드록시스테아르산콜레스테릴, 12-히드록시스테아르산, 스테아르산, 로진산, 라놀린지방산콜레스테릴에스테르 등을 들 수 있다.Examples of the emollients include long chain acyl glutamic acid cholesteryl ester, hydroxystearic acid cholesteryl, 12-hydroxystearic acid, stearic acid, rosin acid and lanolin fatty acid cholesteryl ester.
계면 활성제로서는 비이온성 계면 활성제, 음이온성 계면 활성제, 양이온성 계면 활성제, 양성 계면 활성제 등을 들 수 있다.Examples of the surfactant include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.
비이온성 계면 활성제로서는 자기 유화형 모노스테아르산글리세린, 프로필렌글리콜지방산에스테르, 글리세린지방산에스테르, 폴리글리세린지방산에스테르, 솔비탄지방산에스테르, POE (폴리옥시에틸렌)솔비탄지방산에스테르, POE 솔비트지방산에스테르, POE 글리세린지방산에스테르, POE 알킬에테르, POE 지방산에스테르, POE 경화피마자유, POE 피마자유, POEㆍPOP (폴리옥시에틸렌ㆍ폴리옥시프로필렌) 공중합체, POEㆍPOP 알킬에테르, 폴리에테르변성실리콘, 라우린산알카놀아미드, 알킬아민옥시드, 수소첨가대두인지질 등을 들 수 있다.Examples of the nonionic surfactant include self emulsifying monostearate glycerin, propylene glycol fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, sorbitan fatty acid ester, POE (polyoxyethylene) sorbitan fatty acid ester, POE sorbit fatty acid ester, POE (Polyoxyethylene / polyoxypropylene) copolymer, POE.POP alkyl ether, polyether-modified silicone, polyether-modified silicone, polyoxyethylene-polyoxypropylene (POE) Alkanolamides, alkylamine oxides, hydrogenated soybean phospholipids, and the like.
음이온성 계면 활성제로서는 지방산비누, 알파-아실술폰산염, 알킬술폰산염, 알킬알릴술폰산염, 알킬나프탈렌술폰산염, 알킬황산염, POE 알킬에테르황산염, 알킬아미드황산염, 알킬인산염, POE 알킬인삼염, 알킬아미드인산염, 알킬로일알킬타우린염, N-아실아미노산염, POE 알킬에테르카르복실산염, 알킬술포숙신산염, 알킬술포아세트산나트륨, 아실화 가수분해 콜라겐펩티드염, 퍼플루오로알킬인산에스테르 등을 들 수 있다.Examples of the anionic surfactant include fatty acid soap, alpha-acylsulfonate, alkylsulfonate, alkylarylsulfonate, alkylnaphthalenesulfonate, alkylsulfate, POE alkyl ether sulfate, alkylamide sulfate, alkyl phosphate, POE alkyl ginseng salt, Alkylsulfosuccinic acid salts, acylated hydrolyzed collagen peptide salts, and perfluoroalkyl phosphoric acid esters, and the like can be mentioned. have.
양이온성 계면 활성제로서는 염화알킬트리메틸암모늄, 염화스테아릴트리메틸암모늄, 브롬화스테아릴트리메틸암모늄, 염화세토스테아릴트리메틸암모늄, 염화디스테아릴디메틸암모늄, 염화스테아릴디메틸벤질암모늄, 브롬화베헤닐트리메틸암모늄, 염화벤잘코늄, 스테아르산디에틸아미노에틸아미드, 스테아르산디메틸아미노프로필아미드, 라놀린 유도체 제 4급 암모늄염 등을 들 수 있다.Examples of the cationic surfactant include alkyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, stearyl trimethyl ammonium bromide, cetostearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride, behenyl trimethyl ammonium chloride, Benzalkonium, diethylaminoethylamide stearate, dimethylaminopropylamide stearate, quaternary ammonium salts of lanolin derivatives, and the like.
양성 계면 활성제로서는 카르복시베타인형, 아미드베타인형, 술포베타인형, 히드록시술포베타인형, 아미드술포베타인형, 포스포베타인형, 아미노카르복실산염형, 이미다졸린 유도체형, 아미드아민형 등의 양성 계면 활성제 등을 들 수 있다.Examples of the amphoteric surfactant include carboxybetaine type, amide betaine type, sulfobetaine type, hydroxysulfobetaine type, amidosulfobetaine type, phosphobetaine type, aminocarboxylate type, imidazoline derivative type and amide amine type Amphoteric surfactants and the like.
유기 및 무기 안료로서는 규산, 무수규산, 규산마그네슘, 탤크, 세리사이트, 마이카, 카올린, 벵갈라, 클레이, 벤토나이트, 티탄피막운모, 옥시염화비스무트, 산화지르코늄, 산화마그네슘, 산화아연, 산화티탄, 산화알루미늄, 황산칼슘, 황산바륨, 황산마그네슘, 탄산칼슘, 탄산마그네슘, 산화철, 군청, 산화크롬, 수산화크롬, 칼라민 및 이들의 복합체등의 무기 안료 ; 폴리아미드, 폴리에스테르, 폴리프로필렌, 폴리스티렌, 폴리우레탄, 비닐수지, 요소수지, 페놀수지, 불소수지, 규소수지, 아크릴수지, 멜라민수지, 에폭시수지, 폴리카보네이트수지, 디비닐벤젠ㆍ스티렌 공중합체, 실크파우더, 셀룰로오스, CI 피그먼트옐로우, CI 피그먼트오렌지 등의 유기 안료 및 이들의 무기 안료와 유기 안료의 복합 안료 등을 들 수 있다.Examples of the organic and inorganic pigments include inorganic pigments such as silicic acid, silicic anhydride, magnesium silicate, talc, sericite, mica, kaolin, Bengala, clay, bentonite, titanium mica, titanium oxide, bismuth chloride, zirconium oxide, magnesium oxide, Inorganic pigments such as calcium sulfate, barium sulfate, magnesium sulfate, calcium carbonate, magnesium carbonate, iron oxide, chromium oxide, chromium oxide, chromium hydroxide, But are not limited to, polyamide, polyester, polypropylene, polystyrene, polyurethane, vinyl resin, urea resin, phenol resin, fluororesin, silicon resin, acrylic resin, melamine resin, epoxy resin, polycarbonate resin, Silk powder, cellulose, CI Pigment Yellow, CI Pigment Orange, and composite pigments of inorganic pigments and organic pigments thereof.
유기 분체로서는 스테아르산칼슘 등의 금속비누 ; 세틸린산아연나트륨, 라우릴린산아연, 라우릴린산칼슘 등의 알킬인산금속염 ; N-라우로일-베타-알라닌칼슘, N-라우로일-베타-알라닌아연, N-라우로일글리신칼슘 등의 아실아미노산 다가금속염 ; N-라우로일-타우린칼슘, N-팔미토일-타우린칼슘 등의 아미드술폰산 다가금속염 ; N-엡실론-라우로일-L-리진, N-엡실론-팔미토일리진, N-알파-파리토일올니틴, N-알파-라우로일아르기닌, N-알파-경화우지지방산아실아르기닌 등의 N-아실염기성아미노산 ; N-라우로일글리실글리신 등의 N-아실폴리펩티드 ; 알파-아미노카프릴산, 알파-아미노라우린산 등의 알파-아미노지방산 ; 폴리에틸렌, 폴리프로필렌, 나일론, 폴리메틸메타크릴레이트, 폴리스티렌, 디비닐벤젠ㆍ스티렌 공중합체, 사불화에틸렌 등을 들 수 있다.As the organic powder, metallic soap such as calcium stearate; Metal salts of alkyl phosphates such as sodium zinc cetylate, zinc laurylate and calcium lauryl laurate; Acylamino acid polyvalent metal salts such as N-lauroyl-beta-alanine calcium, N-lauroyl-beta-alanine zinc and N-lauroylglycine calcium; Amidosulfonic acid multivalent metal salts such as N-lauroyl-taurine calcium and N-palmitoyl-taurine calcium; Such as N-epsilon-lauroyl-L-lysine, N-epsilon-palmitoylidene, N-alpha-paratyylnitine, N-alpha-lauroyl arginine, Acyl basic amino acids; N-acylpolypeptides such as N-lauroylglycylglycine; Alpha-amino fatty acids such as alpha-aminocaprylic acid, alpha-aminoaurauric acid, and the like; Polyethylene, polypropylene, nylon, polymethylmethacrylate, polystyrene, divinylbenzene-styrene copolymer, ethylene tetrafluoride, and the like.
자외선 흡수제로서는 파라아미노벤조산, 파라아미노벤조산에틸, 파라아미노벤조산아밀, 파라아미노벤조산옥틸, 살리실산에틸렌글리콜, 살리신산페닐, 살리신산옥틸, 살리신산벤질, 살리신산부틸페닐, 살리신산호모멘틸, 계피산벤질, 파라메톡시계피산-2-에톡시에틸, 파라메톡시계피산옥틸, 디파라메톡시계피산모노-2-에틸헥산글리세릴, 파라메톡시계피산이소프로필, 디이소프로필ㆍ디이소프로필계피산에스테르 혼합물, 우로카닌산, 우로카닌산에틸, 히드록시메톡시벤조페논, 히드록시메톡시벤조페논술폰산 및 그 염, 디히드록시메톡시벤조페논, 디히드록시메톡시벤조페논디술폰산나트륨, 디히드록시벤조페논, 테트라히드록시벤조페논, 4-tert-부틸-4'-메톡시디벤조일메탄, 2,4,6-트리아닐리노-p-(카르보-2'-에틸헥실-1'-옥시)-1,3,5-트리아진, 2-(2-히드록시-5-메틸페닐)벤조트리아졸 등을 들 수 있다.Examples of ultraviolet absorbers include paraaminobenzoic acid, ethyl parnamobenzoate, amyl paranobenzoate, octyl paranobenzoate, ethyleneglycol salicylate, phenyl salicylate, benzyl salicylate, benzyl salicylate, butylphenyl salicylate, homomenthyl salicylate, benzyl cinnamate , Octyl methoxycinnamate, dioctyl methoxycinnamate, mono-2-ethylhexane glyceryl dipyrromethoxycinnamate, isopropyl paratumoxycinnamate, diisopropyl-diisopropyl cinnamate ester mixture, Carninoic acid, ethyl urocanoate, hydroxymethoxybenzophenone, hydroxymethoxybenzophenone sulfonic acid and salts thereof, dihydroxymethoxybenzophenone, sodium dihydroxymethoxybenzophenone disulfonate, dihydroxybenzophenone , Tetrahydroxybenzophenone, 4- tert -butyl-4'-methoxydibenzoylmethane, 2,4,6-trianylino- p- (carbo-2'-ethylhexyl-1'- , 3,5-triazine, 2- (2- And the like can be mentioned hydroxy-5-methylphenyl) benzotriazole.
살균제로서는 히노키티올, 트리클로산, 트리클로로히드록시디페닐에테르, 크로르헥시딘글루콘산염, 페녹시에탄올, 레조르신, 이소프로필메틸페놀, 아줄렌, 살리칠산, 진크필리티온, 염화벤잘코늄, 감광소 301 호, 모노니트로과이어콜나트륨, 운데시렌산 등을 들 수 있다.Examples of the disinfectant include hinokitiol, trichloroacid, trichlorohydroxydiphenyl ether, crohexidine gluconate, phenoxyethanol, resorcin, isopropylmethylphenol, azulene, salicylic acid, zinc filitione, benzalkonium chloride, No. 301, mononitro and eicol sodium, and undecylenic acid.
산화 방지제로서는 부틸히드록시아니솔, 갈릭산프로필, 엘리소르빈산 등을 들 수 있다.Examples of the antioxidant include butylhydroxyanisole, gallic acid propyl, and eicosorbic acid.
pH 조정제로서는 시트르산, 시트르산나트륨, 말산, 말산나트륨, 프말산, 프말산나트륨, 숙신산, 숙신산나트륨, 수산화나트륨, 인산일수소나트륨 등을 들 수 있다.Examples of the pH adjuster include citric acid, sodium citrate, malic acid, sodium malate, fumaric acid, sodium fumarate, succinic acid, sodium succinate, sodium hydroxide, sodium monohydrogenphosphate and the like.
알코올로서는 세틸알코올 등의 고급 알코올을 들 수 있다.Examples of the alcohol include higher alcohols such as cetyl alcohol.
또한, 이외에 첨가해도 되는 배합 성분은 이에 한정되는 것은 아니며, 또, 상기 어느 성분도 본 발명의 목적 및 효과를 손상시키지 않는 범위 내에서 배합 가능하지만, 총중량에 대하여 바람직하게는 0.01 - 5 % 중량, 보다 바람직하게는 0.01 - 3 % 중량로 배합된다.In addition, any of the above components may be blended within the range not to impair the objects and effects of the present invention, but it is preferably 0.01 to 5% by weight based on the total weight, Preferably 0.01 to 3% by weight.
본 발명의 화장료는 용액, 유화물, 점성형 혼합물 등의 형상을 취할 수 있다.The cosmetic of the present invention may take the form of a solution, an emulsion, a viscous mixture or the like.
본 발명의 화장료 조성물에 포함되는 성분은 유효성분으로서 상기 화합물 이외에 화장료 조성물에 통상적으로 이용되는 성분들을 포함할 수 있으며, 예를 들면, 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제 및 담체를 포함한다.The ingredients contained in the cosmetic composition of the present invention may contain, as an active ingredient, the ingredients conventionally used in cosmetic compositions in addition to the above-mentioned compounds, for example, conventional additives such as stabilizers, solubilizers, vitamins, And a carrier.
본 발명의 화장료 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어 유액, 크림, 화장수, 팩, 파운데이션, 로션, 미용액, 모발화장료 등을 들 수 있다.The cosmetic composition of the present invention can be prepared into any formulation conventionally produced in the art, and examples thereof include emulsions, creams, lotions, packs, foundations, lotions, essences, and hair cosmetics.
구체적으로, 본 발명의 화장료 조성물은 스킨로션, 스킨소프너, 스킨토너, 아스트린젠트, 로션, 밀크로션, 모이스쳐 로션, 영양로션, 맛사지크림, 영양크림, 모이스처크림, 핸드크림, 파운데이션, 에센스, 영양에센스, 팩, 비누, 클렌징폼, 클렌징로션, 클렌징크림, 바디로션 및 바디클린저의 제형을 포함한다.Specifically, the cosmetic composition of the present invention can be used as a skin lotion, a skin softener, a skin toner, an astringent, a lotion, a milk lotion, a moisturizing lotion, a nutrition lotion, a massage cream, a nutrition cream, a moisturizing cream, a hand cream, Packs, soaps, cleansing foams, cleansing lotions, cleansing creams, body lotions and body cleansers.
본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물섬유, 식물섬유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다.When the formulation of the present invention is a paste, cream or gel, animal fiber, plant fiber, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component .
본 발명의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다.When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. In the case of a spray, in particular, / Propane or dimethyl ether.
본 발명의 제형이 용액 또는 유탁액의 경우에는 담체 성분으로서 용매, 용매화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌 글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.In the case of the solution or emulsion of the present invention, a solvent, a solvent or an emulsifier is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, , 3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan fatty acid esters.
본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.When the formulation of the present invention is a suspension, a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.
본 발명의 제형이 계면-활성제 함유 클린징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올 에테르 설페이트, 설포숙신산 모노에스테르, 이세티오네이트, 이미다졸리늄 유도체, 메틸타우레이트, 사르코시네이트, 지방산 아미드 에테르 설페이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세리드, 지방산 디에탄올아미드, 식물성 유, 리놀린 유도체 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다.
When the formulation of the present invention is an interfacial active agent-containing cleansing, the carrier component may include aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, linolenic derivatives or ethoxylated glycerol fatty acid esters.
상기에 언급한 바와 같이, 본 발명의 홍화자 추출물로부터 분리된 화합물은 티로시나제 (Tyrosinase) 효소 저해 활성, 엘라스타제 (Elastase) 효소 저해활성, 세포 티로시나제 (celluar tyrosinase) 효소 저해활성, 멜라닌(melanin) 생합성 저해활성, 프로-콜라겐 (Pro-collagen) 생합성 저해 활성 등이 탁월함을 확인함으로써, 상기 조성물은 미백용 피부외용 약학조성물 또는 화장료 조성물로 유용하다.
As described above, the compound isolated from the safflower extract of the present invention is useful as a tyrosinase enzyme inhibiting activity, an elastase enzyme inhibiting activity, a cellulous tyrosinase enzyme inhibiting activity, a melanin biosynthesis Inhibitory activity, pro-collagen biosynthesis inhibitory activity, and the like, the composition is useful as a whitening dermatological pharmaceutical composition or a cosmetic composition.
도 1는 홍화자 추출물로부터 분리된 화합물의 멜라노나 세포 (melanoma cell; B16F10)에서의 세포 생존율에 미치는 영향을 나타낸 도이며(결과는 3중치의 평균(means) ± S.D.으로 표시함);
도 2는 홍화자 추출물로부터 분리된 화합물들의 버섯 티로시나제 저해활성을 나타낸 도이며(결과는 3중치의 평균(means) ± S.D.으로 표시함);
도 3는 홍화자 추출물로부터 분리된 화합물의 멜라노나 세포 (melanoma cell; B16F10)에서의 티로시나제 관련 단백질 발현에 미치는 영향을 나타낸 도이며 {(a) acacetin, (b) cosmosin, (c) N-Feruloyl serotonin, (d) N-(p-coumaroyl) serotonin를 각각 나타내며, 세포는 1, 10 μM 시료 함유 배지에서 48시간 배양하였고, 개개 시료중 티로시나제 단백질 발현 수준은 β-액틴 양으로 정상화하였고, 동일 줄의 서로 상이한 첨자를 갖는 평균치는 유의적으로 상이함. p〈0.05)};
도 4는 홍화자 추출물로부터 분리된 화합물의 멜라노나 세포 (melanoma cell; B16F10)에서의 TRP-1 단백질 발현에 미치는 영향을 나타낸 도이며 {(a) acacetin, (b) cosmosin, (c) N-Feruloyl serotonin, (d) N-(p-coumaroyl) serotonin를 각각 나타내며, 세포는 1, 10 μM 시료 함유 배지에서 48시간 배양하였고, 개개 시료중 티로시나제 단백질 발현 수준은 β-액틴 양으로 정상화하였고, 동일 줄의 서로 상이한 첨자를 갖는 평균치는 유의적으로 상이함. p〈0.05));
도 5는 홍화자 추출물로부터 분리된 화합물의 멜라노나 세포 (melanoma cell; B16F10)에서의 TRP-2 단백질 발현에 미치는 영향을 나타낸 도이다 {(a) acacetin, (b) cosmosin, (c) N-Feruloyl serotonin, (d) N-(p-coumaroyl) serotonin를 각각 나타내며, 세포는 1, 10 μM 시료 함유 배지에서 48시간 배양하였고, 개개 시료중 티로시나제 단백질 발현 수준은 β-액틴 양으로 정상화하였고, 동일 줄의 서로 상이한 첨자를 갖는 평균치는 유의적으로 상이함. p〈0.05)).Brief Description of the Drawings Figure 1 is a graph showing the effect of a compound isolated from a safflower extract on cell viability in melanoma cells (B16F10) (the results are expressed as mean (mean) ± SD);
Figure 2 shows mushroom tyrosinase inhibitory activity of the compounds isolated from the extract of Safflower extract (the results are expressed as mean (mean) ± SD of triplicate);
3 shows the effect of a compound isolated from a safflower extract on tyrosinase-related protein expression in melanoma cells (B16F10), {(a) acacetin, (b) cosmosin, (c) N-feruloyl serotonin , and (d) N- (p-coumaroyl) serotonin, respectively. Cells were cultured for 48 hours in a medium containing 1 μM sample. The expression level of tyrosinase protein in each sample was normalized to the amount of β-actin. The mean values with different subscripts are significantly different. p <0.05)};
FIG. 4 is a graph showing the effect of a compound isolated from a safflower extract on the expression of TRP-1 protein in melanoma cells (B16F10), {(a) acacetin, (b) cosmosin, (c) N-feruloyl serotonin, and (d) N- (p-coumaroyl) serotonin. Cells were cultured for 48 hours in a medium containing 1 and 10 μM samples. The expression level of tyrosinase protein in each sample was normalized to the amount of β- The mean value with different subscripts is significantly different. p <0.05));
FIG. 5 is a graph showing the effect of a compound isolated from a safflower extract on the expression of TRP-2 protein in melanoma cells (B16F10) (acacetin, (b) cosmosin, (c) N-feruloyl serotonin, and (d) N- (p-coumaroyl) serotonin. Cells were cultured for 48 hours in a medium containing 1 and 10 μM samples. The expression level of tyrosinase protein in each sample was normalized to the amount of β- The mean value with different subscripts is significantly different. p < 0.05)).
이하, 본 발명을 하기 실시예 및 실험예에 의해 상세히 설명한다.Hereinafter, the present invention will be described in detail with reference to the following examples and experimental examples.
단, 하기 실시예 및 실험예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예, 참고예 및 실험예에 의해 한정되는 것은 아니다.
However, the following Examples and Experimental Examples are merely illustrative of the present invention, and the contents of the present invention are not limited by the following Examples, Reference Examples and Experimental Examples.
실시예 Example 1. 홍화자 추출 및 용매분획1. Safflower Extraction and Solvent Fraction
건조한 홍화씨를 분쇄한 다음 100% n-hexane을 가하여 상온에서 추출하여 지방을 제거하였다. 위의 추출조작을 3회 반복 실시하여 남은 잔사에 70% Ethanol을 가하여 상온에서 추출·여과하였다. 위의 추출조작을 실시하여 얻은 70% Ethanol 추출액을 감압·농축한 다음 여기에 n-hexane을 넣고 n-hexane층과 수층으로 분획하고 수층에 Ethyl acetate(EtOAc)을 넣고 EtOAc층과 수층으로 분획하고 수층에 n-buOH을 넣고 n-buOH과 수층으로 분획하였다. 위의 과정 중 EtOAc층을 감압·농축하여 EtOAc 추출물(388.61g)을 얻었다. EtOAc 추출물을 HPLC로 측정하여 주요 물질의 대략적인 정보를 파악하였다. 이 추출물 중 200g을 CHCl3:MeOH (10:1 to MeOH 100%) 혼액에 충진 시킨 후 Silicagel(230~400 mesh, Merck, Germany) column에 흡착시킨 후 7개 분획물을 얻었다. 이 중 Fr.E1과 Fr.E5는 MeOH를 이용한 재결정 유도법을 통하여 각각 acacetin(7.74mg), cosmosiin(4.76mg) 단일물질을 얻었다. Fr.E4 전량을 CHCl3:MeOH (5:1 to MeOH 100%) 혼액에 충진 시킨 후 Silicagel(230~400 mesh, Merck, Germany) column에 흡착시킨 후 5개 분획물을 얻었다. 이 중 Fr.E4.2는 MeOH를 이용한 재결정 유도법을 통하여 N-feruloylserotonin(6.13mg) 단일물질을 얻었다. Fr.E4.3을 CHCl3:MeOH (10:1 to MeOH 100%) 혼액에 충진 시킨 후 Silicagel(230~400 mesh, Merck, Germany) column에 흡착시킨 후 8개 분획물을 얻었다. 이 중 Fr.E4.3.4 전량을 CHCl3:MeOH (15:1 to MeOH 100%) 혼액에 충진 시킨 후 Silicagel(230~400 mesh, Merck, Germany) column에 흡착시킨 후 8개 분획물을 얻었다. 이 중 Fr.E4.3.4.7로부터 N-(p-coumaroyl)serotonin(15.33mg) 단일물질을 얻었다. (도 1 및 2 참조)Dried safflower seeds were ground and 100% n- hexane was added and extracted at room temperature to remove fat. The above extraction procedure was repeated three times and 70% ethanol was added to the remaining residue, which was then extracted and filtered at room temperature. Under reduced pressure for 70% Ethanol extract obtained by carrying out the extraction operation, the above concentration into the following here Ethyl acetate (EtOAc) and the aqueous layer into the n -hexane fraction with n -hexane layer from the aqueous layer, and the fraction with EtOAc layer from the aqueous layer N- BuOH was added to the water layer and the water was separated into n- BuOH and water. During the above procedure, the EtOAc layer was concentrated under reduced pressure to obtain EtOAc extract (388.61 g). The EtOAc extract was assayed by HPLC to obtain an approximate view of the major materials. 200g of this extract was packed in a CHCl 3 : MeOH (10: 1 to MeOH 100%) mixture and adsorbed on a column of Silicagel (230-400 mesh, Merck, Germany) to obtain 7 fractions. Among them, Fr.E1 and Fr.E5 obtained acacetin (7.74 mg) and cosmosiin (4.76 mg) respectively through recrystallization induction method using MeOH. CHCl Fr.E4 the total volume 3: MeOH (5: 1 to MeOH 100%) was charged into a mixture Silicagel (230 ~ 400 mesh, Merck , Germany) to obtain a five fraction was adsorbed to the column. Among them, Fr.E4.2 obtained N- feruloylserotonin (6.13 mg) single substance through recrystallization induction method using MeOH. The CHCl Fr.E4.3 3: MeOH (10: 1 to
하기에 홍화자 추출물로부터 분리된 개개화합물들의 물성치를 기재하고 이 물성치를 문헌에 개시된 물성치들과 각각 비교하여 그 구조를 동정하였다. (18Sakamura, A., T erayama, Y., Kawakat su, S., Ichihara, A. and Saito, H. (1980) Conjugated serotonins and phenolic constituent s in safflower seed (Carthamus tinctorius L.). A g ric . B iol . Chem ., 44, 2951.)
The physical properties of the individual compounds isolated from the extracts of the safflower extract were described below, and their properties were compared with the physical properties disclosed in the literature, and their structures were identified. (1980) Conjugated serotonins and phenolic constituents of safflower seed ( Carthamus tinctorius L.). A g ric ( 18) Sakamura, A., T erayama, Y., Kawakata, S., Ichihara, A. and Saito, B iol . Chem , ≪ / RTI > 44, 2951.)
화합물 1 : Compound 1: 아카세틴Acacetin ( ( AcacetinAcacetin ))
성상: 백색 무정형 분말(white amorphous powder)Appearance: white amorphous powder
분자량(Molecular Weight): 270.2369Molecular Weight: 270.2369
1H-NMR (500MHz, DMSO-d 6+D2O) : δ 6.86 (1H, H-3), 6.20 (1H, d, J=2Hz, H-6, ), 6.50 (1H, d, J=2Hz, H-8), 8.03 (2H, d, J=9Hz, H-2',6'), 7.10 (2H, d, J=9Hz, H-3',5') 1 H-NMR (500MHz, DMSO- d 6 + D 2 O): δ 6.86 (1H, H-3), 6.20 (1H, d, J = 2Hz, H-6,), 6.50 (1H, d, J = 2Hz, H-8), 8.03 (2H, d, J = 9Hz, H-2 ', 6'), 7.10 (2H, d, J = 9Hz, H-3 ', 5')
13C-NMR (500MHz, DMSO-d 6+D2O) : δ 163.3 (C-2), 103.6 (C-3), 181.8 (C-4), 157.4 (C-5), 98.9 (C-6), 164.3 (C-7), 94.1 (C-8), 161.5 (C-9), 103.8 (C-10), 122.9 (C-1'), 128.4 (C-2',6'), 114.6 (C-3',5'), 162.3 (C-4'), 55.6 (-OCH3)
13 C-NMR (500 MHz, DMSO- d 6 + D 2 O):? 163.3 (C-2), 103.6 (C-3), 181.8 6), 164.3 (C-7), 94.1 (C-8), 161.5 (C-9), 103.8 114.6 (C-3 ', 5 '), 162.3 (C-4 '), 55.6 (-OCH 3)
화합물 2 : 코스모신(Compound 2: Cosmosin ( CosmosinCosmosin ))
성상: 백색 무정형 분말(white amorphous powder)Appearance: white amorphous powder
분자량(Molecular Weight):432.3775Molecular Weight: 432.3775
1H-NMR (500MHz, DMSO-d 6+D2O) : δ 6.82 (1H, H-3), 6.43 (1H, H-6), 6.86 (1H, d, J=2.5Hz, H-8), 7.94 (2H, dd, J=9Hz, 2.5Hz, H-2',6'), 6.93 (2H, dd, J=9Hz, 2.5Hz, H-3',5'), 5.10 (1H, d, J=7.5Hz, glucose-H) 1 H-NMR (500MHz, DMSO- d 6 + D 2 O): δ 6.82 (1H, H-3), 6.43 (1H, H-6), 6.86 (1H, d, J = 2.5Hz, H-8 ), 7.94 (2H, dd, J = 9 Hz, 2.5 Hz, H-2 ', 6'), 6.93 (2H, dd, J = 9 Hz, 2.5 Hz, H- d, J = 7.5 Hz, glucose-H)
13C-NMR (500MHz, DMSO-d 6+D2O) : δ 164.3 (C-2), 103.1 (C-3), 182.0 (C-4), 161.1 (C-5), 99.5 (C-6), 163.0 (C-7), 94.9 (C-8), 157.0 (C-9), 105.4 (C-10), 121.0 (C-1'), 128.7 (C-2',6'), 116.0 (C-3',5'), 161.4 (C-4'), 99.9, 77.2, 60.6, 69.6, 76.4, 73.1 (glucose-C)
13 C-NMR (500MHz, DMSO- d 6 + D 2 O): δ 164.3 (C-2), 103.1 (C-3), 182.0 (C-4), 161.1 (C-5), 99.5 (C- 6), 163.0 (C-7), 94.9 (C-8), 157.0 (C-9), 105.4 C-4 '), 99.9, 77.2, 60.6, 69.6, 76.4, 73.1 (glucose-C)
화합물 3 : Compound 3: NN -페룰로세르토닌(- ferulocortonin ( feruloylserotoninferuloylserotonin ))
성상: 백색 무정형 분말(white amorphous powder)Appearance: white amorphous powder
분자량(Molecular Weight): 352.3838Molecular Weight: 352.3838
1H-NMR (500MHz, Methanol) : δ 6.93 (1H, H-2), 6.88 (1H, d, J=2Hz, H-4), 6.58 (1H, dd, J=2.5Hz, 8.5Hz, H-6), 7.07 (1H, d, J=8.5Hz, H-7), 2.84 (2H, t, J=7Hz, H-10), 3.48 (2H, t, J=7Hz, H-11), 7.01 (1H, d, J=1.5Hz, H-2'), 6.69 (1H, d, J=8Hz, H-5'), 6.91 (1H, d, J=1.5Hz, H-6'), 7.35 (1H, d, J=15.5Hz, H-7'), 7.32 (1H, d, J=15.5Hz, H-8') 1 H-NMR (500MHz, Methanol ): δ 6.93 (1H, H-2), 6.88 (1H, d, J = 2Hz, H-4), 6.58 (1H, dd, J = 2.5Hz, 8.5Hz, H -6), 7.07 (1H, d , J = 8.5Hz, H-7), 2.84 (2H, t, J = 7Hz, H-10), 3.48 (2H, t, J = 7Hz, H-11), 7.01 (1H, d, J = 1.5Hz, H-2 '), 6.69 (1H, d, J = 8Hz, H-5'), 6.91 (1H, d, J = 1.5Hz, H-6 '), 7.35 (1H, d, J = 15.5Hz, H-7 '), 7.32 (1H, d, J = 15.5Hz, H-8')
13C-NMR (500MHz, Methanol) : δ 124.4 (C-2), 112.8 (C-3), 103.7 (C-4), 151.3 (C-5), 112.5 (C-6), 112.7 (C-7), 133.3 (C-8), 129.6 (C-9), 26.6 (C-10), 41.6 (C-11), 128.5 (C-1'), 111.7 (C-2'), 149.4 (C-3'), 149.9 (C-4'), 116.6 (C-5'), 123.4 (C-6'), 142.1 (C-7'), 119.0 (C-8'), 169.4 (C-9'), 56.4 (-OCH3)
13 C-NMR (500MHz, Methanol ): δ 124.4 (C-2), 112.8 (C-3), 103.7 (C-4), 151.3 (C-5), 112.5 (C-6), 112.7 (C- (C-1), 111.7 (C-2), 149.4 (C-11), 133.6 C-3 '), 149.9 (C-4'), 116.6 (C-5 '), 123.4 '), 56.4 (-OCH 3)
화합물 4 : Compound 4: NN -(- ( pp -- 쿠마로일Kumaroto )) 세르토닌Serotonin ( ( NN -(- ( pp -- coumaroylcoumaroyl )) serotoninserotonin ))
성상: 백색 무정형 분말(white amorphous powder)Appearance: white amorphous powder
분자량(Molecular Weight): 322.3578Molecular Weight: 322.3578
1H-NMR (500MHz, Methanol) : δ 6.91 (1H, H-2), 6.86 (1H, d, H-4), 6.56 (1H, dd, J=2.5Hz, 8.5Hz, H-6), 7.05 (1H, dd, J=3.0Hz, 8.5Hz, H-7), 2.82 (2H, t, J=7Hz, H-10), 3.46 (2H, t, J=7Hz, H-11), 7.28 (1H, d, J=5.5Hz, H-2'), 6.67 (1H, d, J=5.5Hz, H-3'), 6.67 (1H, d, J=5.5Hz, H-5'), 7.28 (1H, d, J=5.5Hz, H-6'), 7.34 (1H, dd, J=2.5Hz, 15.5Hz, H-7'), 6.28 (1H, dd, J=3.5Hz, 15.5Hz, H-8') 1 H-NMR (500MHz, Methanol ): δ 6.91 (1H, H-2), 6.86 (1H, d, H-4), 6.56 (1H, dd, J = 2.5Hz, 8.5Hz, H-6), 7.05 (1H, dd, J = 3.0Hz, 8.5Hz, H-7), 2.82 (2H, t, J = 7Hz, H-10), 3.46 (2H, t, J = 7Hz, H-11), 7.28 (1H, d, J = 5.5Hz , H-2 '), 6.67 (1H, d, J = 5.5Hz, H-3'), 6.67 (1H, d, J = 5.5Hz, H-5 '), 7.28 (1H, d, J = 5.5Hz, H-6 '), 7.34 (1H, dd, J = 2.5Hz, 15.5Hz, H-7'), 6.28 (1H, dd, J = 3.5Hz, 15.5Hz , H-8 ')
13C-NMR (500MHz, Methanol) : δ 124.6 (C-2), 112.5 (C-3), 103.7 (C-4), 151.3 (C-5), 112.6 (C-6), 112.8 (C-7), 133.3 (C-8), 129.6 (C-9), 26.6 (C-10), 41.6 (C-11), 127.9 (C-1'), 130.7 (C-2'), 116.8 (C-3'), 160.6 (C-4'), 116.8 (C-5'), 130.7 (C-6'), 141.9 (C-7'), 118.7 (C-8'), 169.4 (C-9')
13 C-NMR (500MHz, Methanol ): δ 124.6 (C-2), 112.5 (C-3), 103.7 (C-4), 151.3 (C-5), 112.6 (C-6), 112.8 (C- (C-11), 127.9 (C-1), 130.7 (C-2), 116.8 (C-10) 3 '), 160.6 (C-4'), 116.8 (C-5 '), 130.7 (C-6'), 141.9 ')
실험예Experimental Example 1. One. MTTMTT assayassay 에 의한 세포 생존율 측정Of cell survival
실시예에서 얻은 시료들의 MTT assay에 의한 세포 생존율을 시험하기 위하여 문헌에 개시된 Carmichael의 방법을 응용하여 하기와 같이 실험하였다(Carmichael J, Degraff WG, Gadzar AF. 1987. Evaluation of a tetrazolium based semiautomated colorimetric assay: Assessment of chemosensitivity testing. Cancer Res 477: 936-942..)
In order to test the cell viability by MTT assay of the samples obtained in the examples, Carmichael's method disclosed in the literature was applied as follows (Carmichael J, Degraff WG, Gadzar AF 1987. Evaluation of a tetrazolium based semiautomated colorimetric assay : Assessment of chemosensitivity testing. Cancer Res 477: 936-942 ..)
1-1. 세포 배양1-1. Cell culture
마우스 흑색 (B16F10, Manassas, VA) 세포는 Michikawa등(Michikawa M, Lim KT, McLarnon JG, Kim SU:Oxygen radical-induced neurotoxicity in spinal cord neuron cultures. J. Neurosci Res. 37:62-70 (1994)19)의 방법에 따라 배양 세포에 0.25% trypsin 용액을 희석 처리한 후 세포를 분리한 다음 DuLbeco's modified eagle’s medium(DMEM) 배지에 10% fetal bovine serum(FBS)과 1% penicillin/streptomycin(100U/mL)을 첨가하여 37℃, 5% CO2 배양기에 적응시켜 배양하였다.
Cells of mouse black (B16F10, Manassas, Va.) Cells were cultured in the presence or absence of cells of the spinal cord of neurons cultured in the spinal cord of neurons cultured in spinal cord neuron cultures, J. Neurosci Res. 37: 62-70 (1994), Michikawa et al. ( Michikawa M, Lim KT, McLarnon JG, according to the process of 19) was separated and then diluted with process a 0.25% trypsin solution to the culture cells following DuLbeco's modified eagle's medium (DMEM ) 10% fetal bovine serum (FBS) in the culture medium and 1% penicillin / streptomycin (100U / mL ) Was added and cultured at 37 ° C in a 5% CO 2 incubator.
1-2. 1-2. MTTMTT assayassay 에 의한 세포 생존능력 측정Of cell viability
세포 생존률 측정은 Carmichael 등(Carmichael J, Degraff WG, Gadzar AF. 1987. Evaluation of a tetrazolium based semiautomated colorimetric assay: Assessment of chemosensitivity testing. Cancer Res 477: 936-942.20)의 방법에 따라 측정하였다. Melanoma(B16F10)을 96well plate에 5×104cells/well이 되게 0.18mL 분주하고, 시료를 농도 별로 조제하여 0.02mL 첨가한 후 37℃, 5% CO2 incubator에서 48시간 배양하였다. 대조군은 시료와 동량의 증류수를 첨가하여 동일한 조건으로 배양하였다. 여기에 5mg/mL 농도로 제조한 MTT 용액 0.02mL를 첨가하여 4시간 배양한 후 배양액을 제거하고 각 well당 DMSO:EtOH (1:1) 0.15mL를 가하여 실온에서 30분간 반응 시킨 뒤 ELISA reader로 550nm에서 흡광도를 측정하였다. 세포 독성 측정은 하기 수학식 1의 시료용액의 첨가군와 무첨가군의 흡광도 감소율로 나타내었다.Cell viability was measured by the method of Carmichael et al. ( Carmichael J, Degraff WG, Gadzar AF 1987. Evaluation of a tetrazolium-based semiautomated colorimetric assay: Cancer Res 477: 936-942. 20) . Melanoma (B16F10) was dispensed into a 96-well plate at a concentration of 5 × 10 4 cells / well (0.18 mL), and 0.02 mL of each sample was added to the wells and incubated at 37 ° C in a 5% CO 2 incubator for 48 hours. In the control group, the same amount of distilled water as that of the sample was added and the cells were cultured under the same conditions. After adding 0.02 mL of MTT solution (5 mg / mL) and incubating for 4 hours, the culture solution was removed, and 0.15 mL of DMSO: EtOH (1: 1) was added to each well and reacted at room temperature for 30 minutes. Absorbance was measured at 550 nm. Cytotoxicity measurement was expressed by the absorbance reduction ratio of the group of addition of the sample solution and the group of no addition of the following formula (1).
멜라노마(melanoma) 세포의 생존율을 MTT assay에 의해 확인한 결과, 도 1와 같이 나타내었다. acacetin, cosmosin, N-feruloyl serotonin, N-(p-Coumaroyl) serotonin의 경우 1, 10 μM의 농도에서 80%에 가까운 생존율을 나타내어 낮은 세포 독성율을 확인 하였으며, 50, 100 μM의 농도에서는 50%이하의 생존율을 나타내어 강한 세포 독성율을 나타내는 것을 확인하였다. 멜라노나 세포 (melanoma cell; B16F10)에서의 티로시나제(tyrosinase) 활성도와 멜라닌 생합성량, 미백관련 신호전달 인자 측정은 생존율이 100%에 가까운 농도인 1, 10 μM의 농도로 확인하였다.
The survival rate of melanoma cells was confirmed by MTT assay as shown in Fig. (p-Coumaroyl) serotonin showed a low cytotoxicity with a survival rate of 80% at concentrations of 1 and 10 μM, and 50% at 50 and 100 μM, respectively. The survival rate was as follows, indicating a strong cytotoxicity rate. Tyrosinase activity, melanin biosynthesis and whitening signal transduction factors in melanoma cells (B16F10) were measured at concentrations of 1 and 10 μM, which were close to 100% in survival rate.
실험예Experimental Example 2. 미백 활성 실험 2. Whitening activity experiment
2-1. 2-1. 티로시나제Tyrosinase 저해활성 Inhibitory activity
실시예에서 얻은 시료들의 티로시나제 (Tyrosinase) 저해활성을 시험하기 위하여 문헌에 개시된 Yagi 등의 방법을 응용하여 하기와 같이 실험하였다 ((21)Yagi AT, Kanbara T, Morinobu N. The effect of tyrosinase inhibition for aloe. Planta Med. 3981: 517-519 (1986))In order to test the tyrosinase inhibitory activity of the samples obtained in the examples, the following experiment was conducted by applying the method of Yagi et al. ( 21 ) to Yagi AT, Kanbara T, Morinobu N. The effect of tyrosinase inhibition aloe, Planta Med., 3981: 517-519 (1986))
반응구는 0.175M sodium phosphate buffer(pH 6.8) 0.5mL에 10mM L-DOPA를 녹인 기질액 0.2mL 및 시료용액 0.1mL의 혼합액에 mushroom tyrosinase(110U/mL) 0.2mL을 첨가하여 25℃에서 2분간 반응시켜 반응액 중에 생성된 DOPA chrome을 475nm에서 측정한다. Tyrosinase 저해활성은 하기 수학식 2의 시료용액의 첨가구와 무첨가구의 흡광도 감소율로 나타내었다.To the reaction mixture, 0.2 mL of mushroom tyrosinase (110 U / mL) was added to a mixture of 0.2 mL of the substrate solution in which 10 mM L-DOPA was dissolved in 0.5 mL of 0.175 M sodium phosphate buffer (pH 6.8) and 0.1 mL of the sample solution and the mixture was reacted at 25 ° C. for 2 minutes And the DOPA chrome produced in the reaction solution is measured at 475 nm. The tyrosinase inhibitory activity was represented by the absorbance reduction rate of the sample solution of the following formula (2) and the non-added sample.
본 실험 결과, 버섯(mushroom) 유래의 티로시나제(tyrosinase) 저해 활성 측정 결과는 도 2와 같이 나타내었다. 본 연구에서는 아카세틴(acacetin), cosmosin, N-feruloyl serotonin, N-(p-Coumaroyl) serotonin에서 1,000μM의 농도에서 tyrosinase 활성이 감소되는 것을 확인할 수 있었다. 특히, acacetin의 경우 1,000 μM에서 59.2%의 저해능을 나타내어 가장 우수한 효능을 나타내었다.
As a result of this experiment, the results of measurement of inhibitory activity of tyrosinase derived from mushroom are shown in FIG. In this study, tyrosinase activity was reduced at a concentration of 1,000 μM in acacetin, cosmosin, N-feruloyl serotonin and N- (p-Coumaroyl) serotonin. In particular, acacetin exhibited the best efficacy with a sensitivity of 59.2% at 1,000 μM.
2-2. 미백 관련 단백질의 발현2-2. Expression of whitening-related proteins
실시예에서 얻은 시료들의 미백 관련 단백질의 발현에 미치는 영향을 시험하기 위하여 문헌에 기재된 웨스턴 블롯법(Western blot)을 통한 미백 관련 단백질의 발현 측정 방법을 응용하여 하기와 같이 실험하였다.In order to test the effect of the samples obtained in the examples on the expression of the whitening-related protein, the method of measuring the expression of the whitening-related protein through the Western blot method described in the literature was applied as follows.
미백관련 인자 MITF, TRP-1, TRP-2, 티로시나제 (tyrosinase) 활성을 보기 위하여 B16F10 멜라노마(melanoma) 세포를 100mm tissue culture dish에 2×104cells/well에 되도록 분주하고 24시간 동안 배양하였다. 배지를 제거한 후 시료를 농도별로 처리한 배지로 교환하고 48시간 배양한 후 PBS로 세척하였다. Lysis buffer (Pierce, Rockford, IL) 100㎕를 첨가하여 세포를 용해시키고 원심분리하여(12,000rpm, 4℃, 20min) 세포막 성분들을 제거하였다. 원심 분리하여 얻은 단백질은 bradford assay로 정량하였으며, 60㎕의 단백질을 10%의 SDS-PAGE(Pierce, Rockford, IL) 를 이용하여 전기 영동한 후, 항체의 비특이적 결합을 억제시키기 위해 PVDF membrane에 옮긴 다음 30~40V에서 2시간 이상 transfer하였다. 분리된 단백질은 PVDF membrane(Hercules, CA, USA)에 옮긴 다음 실온에서 1시간 blocking buffer (5% skim milk in TBST)에서 incubation 시켰다. MMP-1 각각의 1차 항체를 1:1000으로 희석하여 4℃에서 over night한 다음, 다시 10분 간격으로 TBST(Tris-Buffered Saline and Tween , Santa Cruz, CA)로 3회 세척하고 mouse anti-rabbit IgG HRP(Santa Cruz, CA)의 각각의 2차 항체를 1:1,000로 희석하여 실온에서 2시간 동안 배양하였다. 3회 washing한 뒤 LAS 4,000 image analyzer (Fugifilm life science, Tokyo, Japan) 기기를 이용하여 밴드 확인 및 정량하였다. B16F10 melanoma cells were divided into 2 × 10 4 cells / well in a 100-mm tissue culture dish and cultured for 24 hours to examine whitening factors MITF, TRP-1, TRP-2 and tyrosinase activity . After the medium was removed, the sample was exchanged with the treated medium for various concentrations, cultured for 48 hours, and then washed with PBS. Cells were lysed by adding 100 μl of lysis buffer (Pierce, Rockford, IL) and centrifuged (12,000 rpm, 4 ° C, 20 min) to remove cell membrane components. The proteins obtained by centrifugation were quantitated by bradford assay, and 60 μl of the protein was electrophoresed using 10% SDS-PAGE (Pierce, Rockford, Ill.) And transferred to a PVDF membrane to inhibit nonspecific binding of the antibody And then transferred at 30 to 40 V for 2 hours or more. The separated proteins were transferred to PVDF membrane (Hercules, CA, USA) and incubated in blocking buffer (5% skim milk in TBST) for 1 hour at room temperature. Each of the primary antibodies was diluted 1: 1000 and then over-night at 4 ° C. The cells were washed three times with TBST (Tris-Buffered Saline and Tween, Santa Cruz, CA) Each secondary antibody of rabbit IgG HRP (Santa Cruz, Calif.) was diluted 1: 1,000 and incubated at room temperature for 2 hours. After washing three times, bands were identified and quantified using a LAS 4000 image analyzer (Fugifilm life science, Tokyo, Japan).
본 발명의 시료가 멜라닌(melanin) 합성에 관계된 효소인 tyrosinase에 미치는 영향을 알아보기 위하여 B16F10 mouse melanoma 세포에 농도별로 1, 10 μM 처리 한 후 48시간 뒤에 TRP-1, TRP-2, tyrosinase protein 발현을 western blotting으로 확인하였다. 이때 세포의 여러 조건에서도 그 발현정도의 차이가 거의 없는 house keeping gene인 β-actin(Santa Cruz, CA)을 양성 대조군 (positive control)로 사용하였다. In order to investigate the effect of the present invention on tyrosinase, an enzyme involved in the synthesis of melanin, B16F10 mouse melanoma cells were treated with 1, 10 μM of TRP-1, TRP-2, tyrosinase protein Were confirmed by western blotting. Β-actin (Santa Cruz, CA), a house keeping gene with little difference in expression level, was used as a positive control.
도 3 내지 5(=Fig. 3~5)에서 보는 바와 같이 acacetin, cosmosin, N-feruloyl serotonin, N-(p-Coumaroyl) serotonin을 처리 하지 않은 B16F10군에서는 각 전사인자의 단백질 발현이 증가 하였지만, acacetin, cosmosin, N-feruloyl serotonin, N-(p-Coumaroyl) serotonin을 농도별로 1, 10 μM을 처리한 B16F10군에서는 MITF, TRP-1, TRP-2, tyrosinase protein의 발현이 처리하지 않은 군보다 감소하였다. 이러한 결과로 미루어 보아 acacetin, cosmosin, N-feruloyl serotonin, N-(p-Coumaroyl) serotonin은 MITF, TRP-1, TRP-2, tyrosinase의 발현을 단계적으로 저해시킴으로서 멜라닌 생성 억제에 효과가 있을 것으로 판단된다.
As shown in Figs. 3 to 5 (= Fig. 3 to 5), the protein expression of each transcription factor was increased in the B16F10 group not treated with acacetin, cosmosin, N-feruloyl serotonin and N- (p- Coumaroyl) serotonin, The expression of MITF, TRP-1, TRP-2 and tyrosinase protein in the B16F10 group treated with 1, 10 μM of acacetin, cosmosin, N-feruloyl serotonin and N- (p- Coumaroyl) Respectively. These results suggest that acacetin, cosmosin, N-feruloyl serotonin and N- (p-Coumaroyl) serotonin may inhibit melanogenesis by inhibiting the expression of MITF, TRP-1, TRP-2 and tyrosinase do.
이하, 본 발명의 제형예로서 크림, 맛사지크림, 로션, 스킨로션, 에센스, 팩, 클렌징폼의 제형을 예시하고 있으나, 본 발명의 화장품 조성물을 포함하는 제형은 이에 한정되는 것은 아니다.
Hereinafter, formulations of cream, massage cream, lotion, skin lotion, essence, pack, and cleansing foam are exemplified as the formulation examples of the present invention, but the formulations including the cosmetic composition of the present invention are not limited thereto.
제제예Formulation example 1. One. 헤어hair 토닉의Tonic 제조 Produce
아카세틴(acacetin) -------------------------------- 1%Acacetin -------------------------------- 1%
에탄올 ----------------------------------------- 55.0%Ethanol ----------------------------------------- 55.0%
피마자유 ---------------------------------------- 5.0%Castor Freedom ---------------------------------------- 5.0%
글리세린 ---------------------------------------- 3.0%Glycerin ---------------------------------------- 3.0%
피록톤아민 -------------------------------------- 0.1%Pyrrotonamine -------------------------------------- 0.1%
향료, 색소 -------------------------------------- 적량Fragrance, coloring --------------------------------------
정제수 ------------------------------------------ 잔량Purified water ------------------------------------------ Remnant
계 -------------------------------------------- 100.0%
Total -------------------------------------------- 100.0%
제제예Formulation example 2. 2. 헤어hair 로션의 제조 Manufacture of lotions
코스모시인(cosmosiin) --------------------------- 1.0%Cosmosi (cosmosiin) --------------------------- 1.0%
세토스테아릴알코올 ------------------------------ 2.0%Cetostearyl alcohol ------------------------------ 2.0%
염화스테아릴트리에틸암모늄 ---------------------- 2.0%Stearyl triethylammonium chloride - 2.0%
히드록시에틸셀룰로오즈 -------------------------- 0.5%Hydroxyethylcellulose 0.5%
피록톤올아민 ------------------------------------ 0.1%0.0 > 0.1% < / RTI >
향료, 색소 -------------------------------------- 0.5%Spices, coloring -------------------------------------- 0.5%
정제수 ----------------------------------------- 잔량Purified water ----------------------------------------- Remainder
계 -------------------------------------------- 100.0%
Total -------------------------------------------- 100.0%
제제예Formulation example 3. 3. 헤어hair 비누의 제조 Manufacture of soap
N-페룰로세로토닌(feruloylserotonin) ------------- 0.1% N - Feruloylserotonin ------------- 0.1%
이산화티탄 -------------------------------------- 0.2%Titanium Dioxide -------------------------------------- 0.2%
폴리에틸렌글리콜 -------------------------------- 0.8%Polyethylene glycol -------------------------------- 0.8%
글리세린 ---------------------------------------- 0.5%Glycerin ---------------------------------------- 0.5%
에틸렌디아민테트라아세트산 --------------------- 0.05%Ethylenediamine tetraacetic acid - 0.05%
나트륨 ------------------------------------------ 1.0%Sodium ------------------------------------------ 1.0%
색소, 비누향 ------------------------------------ 적량Pigment, soap fragrance ------------------------------------
화장비누베이스(수분 13%, 중량부) ---------------- 잔량Makeup soap base (moisture content 13%, parts by weight) ---------------- Remainder
계 -------------------------------------------- 100.0%
Total -------------------------------------------- 100.0%
제형예Formulation Example 1. 크림조성물 1. Cream composition
유상과 수상을 각각 75 ℃로 가열 혼합한 후 실온으로 냉각한다.The oil phase and water phase are heated to 75 ° C and cooled to room temperature.
제형예Formulation Example 2. 2. 맛사지크림Massage Cream 조성물 Composition
유상과 수상을 각각 75 ℃로 가열 용해 혼합한 후 실온으로 냉각한다.The oil phase and water phase are mixed by heating at 75 DEG C and then cooled to room temperature.
제형예Formulation Example 3. 로션 조성물 3. lotion composition
유상과 수상을 각각 75 ℃로 가열 혼합 유화한 후 실온으로 냉각한다.The oil phase and water phase are mixed and emulsified by heating at 75 ° C and then cooled to room temperature.
제형예Formulation Example 4. 스킨로션 조성물 4. Skin lotion composition
수상과 에탄올상을 각각 제조 혼합한 후 여과한다.The water phase and the ethanol phase are respectively prepared and mixed and then filtered.
제형예Formulation Example 5. 에센스 조성물 5. Essence composition
수상과 에탄올상을 각각 제조 혼합한 후 여과한다.The water phase and the ethanol phase are respectively prepared and mixed and then filtered.
제형예Formulation Example 6. 팩 조성물 6. Pack composition
수상과 에탄올상을 각각 분산 용해하여 혼합시킨 후 실온으로 냉각한다.The water phase and the ethanol phase are dispersively dissolved and mixed, and then cooled to room temperature.
제형예Formulation Example 7. 7. 클렌징폼Cleansing Foam 조성물 Composition
수상과 오일상을 각각 분산 용해하여 혼합 검화한 후 실온으로 냉각한다.The water phase and the oil phase are dispersed and dissolved, mixed and sieved, and then cooled to room temperature.
상기 조성비는 비교적 기호음료에 적합한 성분을 바람직한 실시예로 혼합 조성하였지만 수요계층이나, 수요국가, 사용용도 등 지역적, 민족적 기호도에 따라서 그 배합비를 임의로 변형 실시하여도 무방하다.Although the compositional ratio is relatively mixed with a component suitable for a favorite drink, it is also possible to arbitrarily modify the compounding ratio according to the regional or national preference such as the demand class, the demanding country, and the use purpose.
Claims (5)
상기 추출물은 물, 에탄올, 메탄올, 프로판올, 부탄올, 아세톤, 에틸아세테이트, 헥산, 부틸렌글리콜, 프로필렌글리콜, 함수부틸렌글리콜, 함수프로필렌글리콜, 함수글리세린으로 구성된 그룹으로부터 선택된 하나 이상의 용매인 피부외용 약학조성물.The method according to claim 1,
Wherein the extract is at least one solvent selected from the group consisting of water, ethanol, methanol, propanol, butanol, acetone, ethyl acetate, hexane, butylene glycol, propylene glycol, hydrolyzed butylene glycol, Composition.
상기 약학 조성물은 크림, 젤, 패취, 분무제, 연고제, 경고제, 로션제, 리니멘트제, 파스타제 또는 카타플라스마제 제형인 피부외용 약학조성물.The method according to claim 1,
Wherein the pharmaceutical composition is a cream, a gel, a patch, a spray, an ointment, a warning agent, a lotion, a liniment, a pasta or a catarcoma.
상기 화장료 조성물은 화장수, 스킨, 로션, 영양로션, 영양크림, 마사지 크림, 에센스, 또는 팩의 제형인 화장료 조성물.The method of claim 4, wherein
The cosmetic composition is a formulation of lotion, skin, lotion, nutrition lotion, nutritional cream, massage cream, essence, or pack.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2016111477A1 (en) * | 2015-01-07 | 2016-07-14 | 코스맥스 주식회사 | Cosmetic composition for alleviation or improvement of sebum secretion stimulated by stress, comprising, as active ingredient, extract of carthamus tinctorious l. seed, or mixed extract of carthamus tinctorious l. seed and areca catechu l. seed |
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2013
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2016111477A1 (en) * | 2015-01-07 | 2016-07-14 | 코스맥스 주식회사 | Cosmetic composition for alleviation or improvement of sebum secretion stimulated by stress, comprising, as active ingredient, extract of carthamus tinctorious l. seed, or mixed extract of carthamus tinctorious l. seed and areca catechu l. seed |
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