KR20180013666A - Antioxidant composition comprising uldavioside A - Google Patents
Antioxidant composition comprising uldavioside A Download PDFInfo
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- KR20180013666A KR20180013666A KR1020170000378A KR20170000378A KR20180013666A KR 20180013666 A KR20180013666 A KR 20180013666A KR 1020170000378 A KR1020170000378 A KR 1020170000378A KR 20170000378 A KR20170000378 A KR 20170000378A KR 20180013666 A KR20180013666 A KR 20180013666A
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Abstract
Description
본 발명은 유근피 추출물로부터 분리한 울다비오시드 A(uldavioside A) 화합물을 유효성분으로 함유하는 항산화 조성물에 관한 것이다. The present invention relates to an antioxidative composition containing, as an active ingredient, an uldavioside A compound isolated from a radish extract.
현대적 산업의 발달과 더불어 풍요로운 경제적, 문화적 혜택을 누리고 있지만, 평균 수명의 연장과 함께 성인 질환과 고령화 사회에 따른 삶의 질에 대한 인식이 동반되고 있다. With the development of modern industry, it enjoys rich economic and cultural benefits, but it is accompanied by an awareness of the quality of life due to adult diseases and an aging society, with an increase in life expectancy.
생체 내에서 에너지 생산을 위한 산화과정 중에 상당량의 유해한 활성산소(reactive oxygen species, ROS)들이 생성된다. 이들 활성산소는 생체 내 제거 기작에 의해 대부분 소멸 되지만 순간적으로 활성산소가 발생되어 항산화 방어계와의 균형이 깨지면 각종 질환의 원인이 된다(Aruoma O.I., et al., 1998). 또한 생체 내에서 산화와 관련된 현상으로 노화의 원인을 산소에서 유래되는 활성산소의 역할이 대두되어 이들의 제거에 대한 관심이 높아지고 있다(Fridorich I., 1978).A significant amount of harmful reactive oxygen species (ROS) are produced during the oxidation process for energy production in vivo. These active oxygen species mostly disappear by the in vivo elimination mechanism, but if the balance with the antioxidant defense system is disrupted by instantaneous generation of active oxygen, it causes various diseases (Aruoma O.I., et al., 1998). In addition, as a phenomenon associated with oxidation in vivo, the role of active oxygen derived from oxygen is becoming a cause of aging, and there is a growing interest in elimination thereof (Fridorich I., 1978).
활성산소 생성의 생체 내적 요인으로는 세포 대사 작용, 산화효소, 박테리아 작용 등을 들 수 있고, 생체 외적 요인으로는 오염된 공기, 대사율 증가, 흡연, 발암물질, 특정 항생제, 자외선, 열, 인스턴트 음식의 과량섭취 등을 들 수 있다. In vivo factors of active oxygen production include cellular metabolism, oxidizing enzyme, bacterial action, and in vitro factors include contaminated air, increased metabolic rate, smoking, carcinogens, certain antibiotics, ultraviolet rays, heat, And excessive intake of
활성산소의 종류로는 일반적으로 리피드 라디칼(lipid radical), 슈퍼옥사이드 라디칼(superoxide radical) 및 히드록시 라디칼(hydroxy radical, ·OH)과 같은 라디칼 뿐 만 아니라 비라디칼인 과산화수소(hydrogen peroxidase, H2O2), 리피드 퍼옥시드(lipid peroxide), 차아염소산(hypochlorous acid), N-클로라민(N-chloramine) 성분들을 포함한다. 이들 활성산소들은 단백질, 불포화 지방산 등과 결합하여 과산화 지질을 생성하고, DNA, RNA 등에 손상을 일으키며, 생체막의 손상, 면역능력의 약화와 함께 고혈압, 동맥경화, 심부전, 류미티스 관절염, 알레르기, 암과 같은 각종 질병과 노화를 유발시키게 된다(Chung H.Y., 1992; Yagi K., 1987; Lopaczyski W., et al., 2001; Yu B.P., 1994; Cooke M.S., et al., 1997). 또한 활성산소는 산화스트레스의 주요 요인으로 노화와 깊게 관련되어 있으며 이는 노화 관련 퇴행성질환 뿐만 아니라 만성염증 질환의 주요 원인이기도 하다. 여러 동물에서 활성산소의 비율은 개체 수명과 상관관계가 있으며 활성산소의 양은 개체의 노화 진행 상태를 결정짓는 요인이 된다(Yu B.P., 1994). The active oxygen species generally include radicals such as lipid radicals, superoxide radicals and hydroxy radicals (OH), as well as radicals such as hydrogen peroxidase (H 2 O 2 ), lipid peroxide, hypochlorous acid, and N-chloramine components. These reactive oxygen species bind to proteins, unsaturated fatty acids, and produce lipid peroxides. They cause damages to DNA, RNA, etc., and damage biological membranes and immune functions, as well as hypertension, arteriosclerosis, heart failure, rheumatoid arthritis, allergies, (Chung HY, 1992; Yagi K., 1987; Lopaczyski W., et al., 2001; Yu BP, 1994; Cooke MS, et al., 1997). Active oxygen is also a major factor in oxidative stress and is closely related to aging, which is a major cause of chronic inflammatory diseases as well as aging-related degenerative diseases. In many animals, the ratio of active oxygen is correlated with the life span of the individual, and the amount of active oxygen is a determinant of the aging process of the individual (Yu BP, 1994).
세포내 항산화 효과에 의한 항상성 유지는 세포의 기능을 회복할 수 있으며, 이는 노화의 진행을 예방 또는 지연시킬 뿐만 아니라 만성염증제어 및 면역력을 향상시켜 건강한 삶의 질을 높일 수 있다. 노화 과정에서 항산화 물질은 결함이 나타난 미토콘드리아의 활성을 도모할 수 있고 항상성을 유지시켜 궁극적으로 세포의 생존력을 높이는 것으로 알려져 있다(Lee Y.H., et al., 2015; Yang T.K., et al., 2013). Retention of homeostasis by intracellular antioxidant activity can restore cellular functions, which can prevent or delay the progression of aging, as well as improve the quality of life by improving chronic inflammation control and immunity. It is known that antioxidants in the process of aging can maintain the activity of defective mitochondria and maintain homeostasis, ultimately enhancing the viability of cells (Lee, YH, et al., 2015; Yang, TK, .
따라서 이러한 활성산소들을 효과적으로 제어시키는 항산화제에 대한 연구가 자연스럽게 증가하게 되었다(허수진, 2005). 그러나 디부틸히드록시톨루엔(dibutyl hydroxy toluene, BHT), 부틸히드록시아니솔(butylated hydroxy aniosle, BHA), 삼차부틸히드로퀴논(tert-butylhydroquinone, TBHQ) 등과 같은 합성 항산화제는 열안정성과 인체에 대한 독성이 문제시 되고 있어 사용상에 많은 제한을 받고 있다(Jun B.S., et al., 2001). 따라서 보다 안전하고 우수한 효능을 가진 천연 항산화제에 대한 개발이 지금까지 꾸준히 시도되고 있다. 천연 항산화제는 대부분 식물기원의 항산화성 물질로서 오미자 추출물(Jang E.J., et al., 1996), 칡 추출물(Han M.J., et al., 1999), 감귤류 플라보노이드(Cha J.H., et al., 2000), 뽕나무(Kim H.J., et al., 2000) 등이 항산화능이 높다고 알려져 있다. Therefore, research on antioxidants that effectively control these active oxygen species has naturally increased (Heo, Su-Jin, 2005). However, synthetic antioxidants such as dibutyl hydroxy toluene (BHT), butylated hydroxy anisole (BHA), and tert-butylhydroquinone (TBHQ) (Jun BS, et al., 2001). Therefore, development of natural antioxidants having safer and superior efficacy has been continuously tried. Natural antioxidants are mostly antioxidant substances of plant origin, such as omija extract (Jang EJ, et al., 1996), 칡 extract (Han MJ, et al., 1999), citrus flavonoid (Cha JH, et al., 2000) , And mulberry (Kim HJ, et al., 2000).
유근피는 느릅나무과(Ulmaceae)에 속하는 느릅나무의 코르크층을 벗긴 수피 및 근피를 건조한 것이다(지형준, et al., 1988). 한방에서 유근피는 맛이 달고, 무독하며, 종창, 관절염, 위궤양, 위장병 등에 사용되고, 거담, 항암, 상처 치료 및 염증에도 탁월한 효과가 있다고 보고되어 있다(Duke J.A., 1985). 유근피에 존재하는 천연물로서 β-시토스테롤(β-sitosterol), 피토스테롤(phytosterol), 스티마스테롤(stimasterol), 탄닌(tannin), 전분(starch), 다당류(polysaccharide) 등이 있다. 또한 진통작용을 나타내는 성분인 프리델린(friedelin)과 에피프리엔델라롤(epifriendelalol), 타락세롤(taraxerol) 등의 분리(Matsuzaki T., et al., 1985)와 화학적 조성에 관한 연구(Duke J.A., 1985) 등이 많이 이루어져 있으나 유근피의 다양한 생리활성을 연구한 시도는 아직까지 거의 이루어지지 않았다. It is the dried bark of the cork layer of the elm belonging to the Ulmaceae ( Uljiceae ) and the dried skin (Ji Hyunjoon, et al., 1988). In the oriental medicine, it has been reported that it has an excellent effect on germination, anticancer, wound healing and inflammation (Duke JA, 1985) because it is tasteful, nontoxic, swelling, arthritis, gastric ulcer and gastrointestinal disease. There are natural products such as β-sitosterol, phytosterol, stimasterol, tannin, starch, and polysaccharide. (Matsuzaki T., et al., 1985) and the chemical composition (Duke JA et al., 1985) and the separation of friedelin, epifriendelalol and taraxerol, , 1985). However, attempts to study diverse physiological activities of the carrageenan have not been conducted yet.
이에, 본 발명자는 유근피의 추출물을 함유하는 항산화 조성물을 연구하는 과정에서, 유근피 추출물로부터 분리된 울다비오시드 A(uldavioside A) 화합물이 우수한 항산화 활성을 가지고 있음을 확인함으로써 본 발명을 완성할 수 있었다.Accordingly, the inventors of the present invention have completed the present invention by confirming that the uldavioside A compound, which is isolated from the extract of the radish root extract, has an excellent antioxidative activity in the course of studying an antioxidative composition containing the extract of the radish root .
종래 선행기술로서 한국등록특허 제0893166호에는 느릅나무 추출물의 섬유아세포(fibroblast)의 증식 및 항산화 효과가 기재되어 있고, 한국공개특허 제2008-0036694호에는 유근피를 포함하는 혼합생약 추출물을 함유하는 조성물의 항산화효과가 기재되어 있으나, 울다비오시드 A 화합물이 언급된 바가 없어 본 발명의 구성과 차이가 있다. Korean Patent No. 0893166 discloses a proliferation and antioxidative effect of fibroblast of elm extract and Korean Patent Publication No. 2008-0036694 discloses a composition containing a mixed herbal extract However, the compound of the present invention is different from the composition of the present invention because no cryovioside A compound is mentioned.
또한, 비특허문헌으로서 Son B.W., et al.은 느릅나무에서 분리한 울다비오시드 A 화합물이 기재되어 있으나, 울다비오시드 A 화합물의 항산화 활성은 기재된 바가 없다. As a non-patent document, Son B. W., et al. Discloses a cryobioside A compound isolated from elm, but no antioxidative activity of the cryobioside A compound has been described.
본 발명의 목적은 유근피 추출물로부터 분리한 울다비오시드 A(uldavioside A) 화합물을 유효성분으로 함유하는 항산화 조성물을 제공하는 데 있다. It is an object of the present invention to provide an antioxidative composition containing an uldavioside A compound, which is isolated from an acanthoi extract, as an active ingredient.
본 발명은 하기 화학식 1의 울다비오시드 A 화합물을 유효성분으로 함유하는 항산화 조성물에 관한 것이다. The present invention relates to an antioxidative composition containing, as an active ingredient, a cryoprecipitate A compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 항산화 조성물은 약학적으로 허용 가능한 담체 또는 부형제를 포함하는 약학적 조성물일 수 있다. The antioxidant composition may be a pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient.
상기 약학적 조성물은 울다비오시드 A 화합물이 조성물 총 중량을 기준으로 0.001중량% 내지 50중량%로 첨가될 수 있다. The pharmaceutical composition may be added in an amount of 0.001% by weight to 50% by weight based on the total weight of the composition of the cryovioside A compound.
상기 약학적 조성물은 활성산소에 의해 생성되는 산화물들에 기인하는 질환의 예방 또는 치료를 위하여 사용될 수 있다. The pharmaceutical composition may be used for the prevention or treatment of diseases caused by oxides produced by active oxygen.
상기 활성산소에 의해 생성되는 산화물들에 기인하는 질환은 노화, 만성알콜중독, 죽상동맥경화증, 암, 관상심장질환, 백내장, 당뇨병, 다운증후군, 간염, 허혈이나 재관류성 손상, 류마티스성 관절염, 관절염, 신부전증, 각종 퇴행성 신경질환, 뇌졸중 발작, 아토피성 피부염, 기관지염, 간질, 만성폐쇄성 질환, 당뇨병성 혈관합병증 및 심근경색으로 이루어진 군에서 선택되는 1종 이상의 질환일 수 있다. The diseases caused by the active oxygen-induced oxides include but are not limited to aging, chronic alcoholism, atherosclerosis, cancer, coronary heart disease, cataract, diabetes, Down syndrome, hepatitis, ischemia or reperfusion injury, rheumatoid arthritis, , Renal failure, various degenerative nerve diseases, stroke, atopic dermatitis, bronchitis, epilepsy, chronic obstructive disease, diabetic vascular complication, and myocardial infarction.
또한, 상기 항산화 조성물은 화장료 조성물일 수 있다. In addition, the antioxidant composition may be a cosmetic composition.
상기 화장료 조성물은 울다비오시드 A 화합물이 조성물 총 중량을 기준으로 0.001중량% 내지 50중량%로 첨가될 수 있다. The cosmetic composition may be added in an amount of 0.001% by weight to 50% by weight based on the total weight of the composition of the cryobioside A compound.
상기 화장료 조성물은 피부 노화 방지용일 수 있다.The cosmetic composition may be used for preventing skin aging.
또한, 상기 항산화 조성물은 항산화 효과를 갖는 건강기능식품일 수 있다. In addition, the antioxidant composition may be a health functional food having an antioxidative effect.
상기 건강기능식품은 울다비오시드 A 화합물이 조성물 총 중량을 기준으로 0.001중량% 내지 50중량%로 첨가될 수 있다. The health functional food may be added in an amount of 0.001 wt% to 50 wt% based on the total weight of the composition of the urodavioside A compound.
이하 본 발명을 상세하게 설명한다. Hereinafter, the present invention will be described in detail.
상기 화학식 1의 울다비오시드 A 화합물은 통상적인 방법에 따라 합성할 있으며, 약학적으로 허용 가능한 염으로 제조될 수도 있으며, 또는 유근피 추출물로부터 분리, 정제될 수 있다. The urodiboside A compound of
상기 유근피는 느릅나무과(Ulmaceae)에 속하는 느릅나무의 코르크층을 벗긴 수피 및 근피를 건조한 것이다.The yukigi is a dried bark and fleshy skin of the elm belonging to the Ulmaceae which has been stripped of the cork layer.
상기 느릅나무과에 속하는 느릅나무는 참느릅나무(Ulmus parvifolia JACQ), 비술나무(Ulmus pumila), 느릅나무(Ulmus davidiana var japonica NAK), 당느릅나무(Ulmus davidiana PLANCH), 흑느릅나무(Ulmus davidiana var suberosa), 난티나무(Ulmus laciniata), 왕느릅나무(Ulmus macrocarpa HANCE), 및 큰잎느릅나무(Ulmus macrocarpa var, macrophylla NAK) 등 일 수 있고, 이에 한정되지 않는다.The elm belonging to the elm belongs to Ulmus parvifolia JACQ, Ulmus pumila , Ulmus davidiana var japonica NAK, Ulmus davidiana PLANCH, Ulmus davidiana var suberosa ), Ulmus laciniata , Ulmus macrocarpa HANCE, and Ulmus macrocarpa var, macrophylla NAK, and the like.
상기 유근피 추출물은 유근피를 물, C1 내지 C4의 저급 알코올 또는 이들의 혼합용액을 용매로 하여 추출할 수 있다. 상기 C1 내지 C4 알코올은 메탄올, 프로판올, 이소프로판올, 부탄올 및 이소부탄올로 이루어진 군에서 선택될 수 있다. 바람직하게는 물로부터 추출한다. The extract can be extracted with water, C1 to C4 lower alcohols or a mixed solution thereof as a solvent. The C1 to C4 alcohols may be selected from the group consisting of methanol, propanol, isopropanol, butanol, and isobutanol. Preferably, it is extracted from water.
상기 유근피 추출물로부터 분리된 화합물은 컬럼 크로마토그래피(column chromatography)를 이용하여 정제할 수 있다. 상기 크로마토그래피는 실리카겔 컬럼 크로마토그래피(silica gel column chromatography), HP-20 컬럼 크로마토그래피(HP-20 column chromatography), RP-18 컬럼 크로마토그래피(RP-18 column chromatography), LH-20 컬럼 크로마토그래피(LH-20 column chromatography), 고성능 액체 크로마토그래피 (High-performance liquid chromatography) 등에서 선택하여 사용할 수 있다. The compound isolated from the carrot extract can be purified using column chromatography. The chromatography was carried out by silica gel column chromatography, HP-20 column chromatography, RP-18 column chromatography, LH-20 column chromatography LH-20 column chromatography, and high-performance liquid chromatography.
상기 활성산소에 의해 생성되는 산화물들에 기인하는 질환은 노화, 만성알콜중독, 죽상동맥경화증, 암, 관상심장질환, 백내장, 당뇨병, 다운증후군, 간염, 허혈이나 재관류성 손상, 류마티스성 관절염, 관절염, 신부전증, 각종 퇴행성 신경질환, 뇌졸중 발작, 아토피성 피부염, 기관지염, 간질, 만성폐쇄성 질환, 당뇨병성 혈관합병증 및 심근경색으로 이루어진 군에서 선택되는 1종 이상의 질환일 수 있다. The diseases caused by the active oxygen-induced oxides include but are not limited to aging, chronic alcoholism, atherosclerosis, cancer, coronary heart disease, cataract, diabetes, Down syndrome, hepatitis, ischemia or reperfusion injury, rheumatoid arthritis, , Renal failure, various degenerative nerve diseases, stroke, atopic dermatitis, bronchitis, epilepsy, chronic obstructive disease, diabetic vascular complication, and myocardial infarction.
상기 노화는 활성산소에 의해 생성되는 산화물들에 기인하는 노화일 수 있다. 바람직하게는 활성산소에 의해 생성된 산화물들에 의해 촉진되는 노화일 수 있다.The aging may be aging due to oxides produced by active oxygen. Preferably aging promoted by oxides produced by active oxygen.
상기 퇴행성 신경질환은 알츠하이머병(Alzheimer's disease), 파킨슨병(Parkinsons's disease) 헌팅톤병(Huntington's disease), 다발성 경화증(multiple sclerosis), 다발성 신경위축(polyneuropatchy), 간질(epilepsy), 뇌질환 또는 뇌졸중(stroke) 및 치매(dementia) 등 일 수 있다. The degenerative neurological disease may be selected from the group consisting of Alzheimer's disease, Parkinsons ' s disease Huntington's disease, multiple sclerosis, polyneuropathy, epilepsy, ) And dementia.
상기 항산화 조성물은 상기 화학식 1의 울다비오시드 A 화합물 및 부형제를 포함하는 약학적 조성물을 제공한다. 상기 화합물은 전체 조성물 총 중량에 대하여 바람직하게는 0.001중량% 내지 50중량%, 더 바람직하게는 0.001중량% 내지 40중량%, 가장 바람직하게는 0.001중량% 내지 30중량%로 하여 첨가될 수 있다. The antioxidant composition provides a pharmaceutical composition comprising the cryovioside A compound of
상기 약학적 조성물은, 각각 통상의 방법에 따라 산제, 과립제, 정제, 캡슐제, 현탁액, 에멀젼, 시럽, 에어로졸 등의 경구형 제형, 외용제, 좌제 및 멸균주사용액의 형태로 제형화하여 사용될 수 있다. 상기 약학적 조성물에 포함될 수 있는 담체, 부형제 및 희석제로는 락토즈, 덱스트로즈, 수크로스, 솔비톨, 만니톨, 자일리톨, 에리스리톨, 말티톨, 전분, 아카시아 고무, 알지네이트, 젤라틴, 칼슘포스페이트, 칼슘 실리케이트, 셀룰로즈, 메틸 셀룰로즈, 미정질 셀룰로스, 폴리비닐 피롤리돈, 물, 메틸히드록시벤조에이트, 프로필히드록시벤조에이트, 탈크, 마그네슘 스테아레이트 및 광물유를 들 수 있다. 제제화할 경우에는 보통 사용하는 충진제, 증량제, 결합제, 습윤제, 붕해제, 계면활성제 등의 희석제 또는 부형제를 사용하여 조제된다. 경구투여를 위한 고형제제에는 정제, 환제, 산제, 과립제, 캡슐제 등이 포함되며, 이러한 고형제제는 본 발명의 울다비오시드 A 화합물에 적어도 하나 이상의 부형제, 예를 들면, 전분, 탄산칼슘, 수크로스 또는 락토즈, 젤라틴 등을 섞어 조제된다. 또한 단순한 부형제 이외에 마그네슘 스테아레이트, 탈크 같은 윤활제들도 사용된다. 경구를 위한 액상 제제로는 현탁제, 내용액제, 유제, 시럽제 등이 해당되는데 흔히 사용되는 단순희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제, 보존제 등이 포함될 수 있다. 비경구 투여를 위한 제제에는 멸균된 수용액, 비수성용제, 현탁제, 유제, 동결건조제제, 좌제가 포함된다. 비수성용제, 현탁제로는 프로필렌글리콜, 폴리에틸렌글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. 좌제의 기제로는 위텝솔(witepsol), 마크로골, 트윈(tween)-61, 카카오지, 라우린지, 글리세로제라틴 등이 사용될 수 있다. The pharmaceutical compositions may be formulated in the form of powders, granules, tablets, capsules, oral preparations such as suspensions, emulsions, syrups and aerosols, external preparations, suppositories and sterilized injection solutions according to a conventional method . Examples of carriers, excipients and diluents that can be included in the pharmaceutical composition include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, Cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil. In the case of formulation, a diluent or excipient such as a filler, an extender, a binder, a wetting agent, a disintegrant, or a surfactant is usually used. Solid formulations for oral administration include tablets, pills, powders, granules, capsules and the like, which may contain at least one excipient, such as starch, calcium carbonate, Cross, lactose, gelatin and the like. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used. Examples of the liquid preparation for oral use include suspensions, solutions, emulsions, and syrups. In addition to water and liquid paraffin, simple diluents commonly used, various excipients such as wetting agents, sweeteners, fragrances, preservatives and the like may be included . Formulations for parenteral administration include sterilized aqueous solutions, non-aqueous solutions, suspensions, emulsions, freeze-dried preparations, and suppositories. Examples of the suspending agent include propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like. Examples of suppository bases include witepsol, macrogol, tween-61, cacao butter, laurin, glycerogelatin and the like.
본 발명의 약학적 조성물의 투여량은 치료받을 대상의 연령, 성별, 체중과, 치료할 특정 질환 또는 병리 상태, 질환 또는 병리 상태의 심각도, 투여 경로 및 처방자의 판단에 따라 달라질 것이다. 이러한 인자에 기초한 투여량 결정은 당업자의 수준 내에 있으며, 일반적으로 투여량은 0.01㎎/㎏/일 내지 대략 2000㎎/㎏/일의 범위이다. 더 바람직한 투여량은 1㎎/㎏/일 내지 500㎎/㎏/일이다. 투여는 하루에 한번 투여할 수도 있고, 수회 나누어 투여할 수도 있다. 상기 투여량은 어떠한 면으로든 본 발명의 범위를 한정하는 것은 아니다. The dosage of the pharmaceutical composition of the present invention will depend on the age, sex, body weight of the subject to be treated, the specific disease or condition to be treated, the severity of the disease or condition, the route of administration and the judgment of the prescriber. Dosage determinations based on these factors are within the level of ordinary skill in the art and generally the dosage ranges from 0.01 mg / kg / day to approximately 2000 mg / kg / day. A more preferable dosage is 1 mg / kg / day to 500 mg / kg / 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 약학적 조성물은 쥐, 가축, 인간 등의 포유동물에 다양한 경로로 투여될 수 있다. 투여의 모든 방식은 예상될 수 있는데, 예를 들면, 경구, 직장 또는 정맥, 근육, 피하, 자궁 내 경막 또는 뇌혈관 내 주사에 의해 투여될 수 있다. 본 발명의 화합물은 독성 및 부작용이 거의 없으므로 예방 목적으로 장기간 복용시에도 안심하고 사용할 수 있는 약제이다. The pharmaceutical composition of the present invention can be administered to mammals such as rats, livestock, and humans in various routes. All modes of administration may be expected, for example, by oral, rectal or intravenous, intramuscular, subcutaneous, intra-uterine dural or intracerebral injection. Since the compound of the present invention has little toxicity and side effects, it can be safely used even for long-term administration for preventive purposes.
또한, 상기 항산화 조성물은 화장료 조성물일 수 있다. In addition, the antioxidant composition may be a cosmetic composition.
상기 화장료 조성물은 상기 화학식 1의 울다비오시드 A 화합물이 전체 조성물 총 중량에 대하여 바람직하게는 0.001중량% 내지 50중량%, 더 바람직하게는 0.001중량% 내지 40중량%, 가장 바람직하게는 0.001중량% 내지 30중량%로 하여 첨가될 수 있다. The cosmetic composition preferably contains 0.001% by weight to 50% by weight, more preferably 0.001% by weight to 40% by weight, and most preferably 0.001% by weight, of the crybabioside A compound of
상기 화장료 조성물은, 용액, 겔, 고체 또는 반죽 무수 생성물, 수상에 유상을 분산시켜 얻은 에멀젼, 현탁액, 마이크로에멀젼, 마이크로캡슐, 미세과립구 또는 이온형(리포좀), 비이온형의 소낭 분산제의 형태, 크림, 스킨, 로션, 파우더, 연고, 스프레이 또는 콘실 스틱의 형태로 제공될 수 있다. 또한, 포말(foam)의 형태 또는 압축된 추진제를 더 함유한 에어로졸 조성물의 형태로도 제조될 수 있다.The cosmetic composition may be in the form of a solution, a gel, a solid or a paste anhydrous product, an emulsion obtained by dispersing an oil phase in an aqueous phase, a suspension, a microemulsion, a microcapsule, a microgranule or an ionic form (liposome) Creams, skins, lotions, powders, ointments, sprays or conical sticks. It can also be prepared in the form of a foam or an aerosol composition further containing a compressed propellant.
상기 화장료 조성물은 본 발명의 울다비오시드 A 화합물에 지방물질, 유기용매, 용해제, 농축제 및 겔화제, 연화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온봉쇄제 및 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭 또는 화장품에 통상적으로 사용되는 임의의 다른 성분과 같은 화장품 분야에서 통상적으로 사용되는 보조제를 함유할 수 있다. The cosmetic composition may be added to the cryoprecipitate A compound of the present invention in the form of a lipid, an organic solvent, a solubilizer, a thickening agent and a gelling agent, a softening agent, a suspending agent, a stabilizer, a foaming agent, a fragrance, Or any other commonly used in cosmetics such as nonionic emulsifiers, fillers, sequestering and chelating agents, preservatives, vitamins, barrier agents, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or cosmetics ≪ RTI ID = 0.0 > cosmetics. ≪ / RTI >
상기 화장료 조성물은 화장수, 젤, 유용성 리퀴드, 크림, 연고 및 에센스 중에서 선택될 수 있다. The cosmetic composition may be selected from lotion, gel, oil-soluble liquid, cream, ointment and essence.
상기 화장료 조성물은 피부 노화 방지용일 수 있다. The cosmetic composition may be used for preventing skin aging.
또한, 상기 항산화 조성물은 항산화 효과를 갖는 건강기능식품일 수 있다. In addition, the antioxidant composition may be a health functional food having an antioxidative effect.
상기 건강기능식품은 상기 화학식 1의 울다비오시드 A 화합물 및 식품학적으로 허용 가능한 식품보조 첨가제를 포함하는 항산화 효과를 갖는 건강기능식품을 제공한다. The health functional food provides a health functional food having an antioxidative effect including a crodobiose A compound of formula (1) and a pharmaceutically acceptable food-aid additive.
상기 울다비오시드 A 화합물은 전체 식품 총 중량에 대하여 바람직하게는 0.001중량% 내지 50중량%, 더 바람직하게는 0.001중량% 내지 30중량%, 가장 바람직하게는 0.001중량% 내지 10중량%로 하여 첨가될 수 있다. The above-mentioned urodibioside A compound is preferably added in an amount of 0.001 to 50% by weight, more preferably 0.001 to 30% by weight, and most preferably 0.001 to 10% by weight based on the total weight of the total food .
상기 건강기능식품은 정제, 캡슐제, 환제 또는 액제 등의 형태를 포함하며, 본 발명의 추출물을 첨가할 수 있는 식품으로는, 예를 들어, 각종 식품류, 음료, 껌, 차, 비타민 복합제, 건강기능성식품류 등이 있다. The health functional food includes forms such as tablets, capsules, pills, and liquids. Examples of the foods to which the extract of the present invention can be added include various foods, beverages, gums, tea, Functional foods.
본 발명은 유근피 추출물로부터 분리한 울다비오시드 A(uldavioside A) 화합물을 유효성분으로 함유하는 항산화 조성물에 관한 것으로, 상기 울다비오시드 A 화합물이 우수한 항산화 활성이 있음을 확인하였다. The present invention relates to an antioxidative composition containing, as an active ingredient, an uldavioside A compound isolated from a carrot extract, and it has been confirmed that the above-mentioned urodiboside A compound has an excellent antioxidative activity.
이를 통해, 본 발명의 울다비오시드 A 화합물을 활성산소에 의해 생성되는 산화물들에 기인하는 각종 질환의 예방 또는 치료용 조성물, 항노화 관련 화장료 조성물 및 항산화용 건강기능식품의 개발에 이용할 수 있을 것으로 기대된다. Accordingly, the present invention can be used for the development of a composition for preventing or treating various diseases caused by oxides produced by active oxygen, an anti-aging-related cosmetic composition, and a health functional food for antioxidation It is expected.
도 1은 본 발명의 울다비오시드 A(uldavioside A) 화합물에 대한 1H-1H COSY(bold lines) 및 1H-13C HMBC 상관관계(arrow)를 나타내는 그림이다.
도 2는 본 발명의 울다비오시드 A 화합물의 C2C12(A) 및 NIH3T3(B) 세포에서의 과산화수소(H2O2)생성 억제 활성을 보여주고 있다.
도 3은 본 발명의 울다비오시드 A 화합물의 DPPH 라디칼 소거능을 보여주고 있다.
도 4는 본 발명의 울다비오시드 A 화합물의 총 항산화능을 보여주고 있다.
도 5는 본 발명의 울다비오시드 A 화합물의 C2C12(A) 및 NIH3T3(B) 세포에서의 세포 독성 결과를 보여주고 있다. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a diagram showing the correlation between 1 H- 1 H COZY (bold lines) and 1 H- 13 C HMBC for an uldavioside A compound of the present invention (arrow).
Figure 2 shows the C2C12 (A) and NIH3T3 (B) hydrogen peroxide (H 2 O 2) generated from the inhibitory activity of the cells of the invention A seed weep rainy compound.
Figure 3 shows the DPPH radical scavenging activity of the cryovioside A compound of the present invention.
Figure 4 shows the total antioxidant activity of the cryovioside A compound of the present invention.
FIG. 5 shows the cytotoxicity results of C2C12 (A) and NIH3T3 (B) cells of the cryovioside A compound of the present invention.
이하 본 발명의 바람직한 실시예를 상세히 설명하기로 한다. 그러나 본 발명은 여기서 설명되는 실시예에 한정되지 않고 다른 형태로 구체화될 수도 있다. 오히려, 여기서 소개되는 내용이 철저하고 완전해지고, 당업자에게 본 발명의 사상을 충분히 전달하기 위해 제공하는 것이다. Hereinafter, preferred embodiments of the present invention will be described in detail. However, the present invention is not limited to the embodiments described herein but may be embodied in other forms. Rather, the intention is to provide an exhaustive, complete, and complete disclosure of the principles of the invention to those skilled in the art.
<실시예 1. 울다비오시드 A 화합물의 분리>≪ Example 1: Isolation of cryptobioside A compound >
유근피는 느릅나무(Ulmus davidiana Planch)의 유근피를 농가에서 건조한 것을 구입하여 사용하였다. 건조된 유근피 10g에 정제수 1ℓ를 첨가한 후 반연속식 저온진공추출기로 25℃에서 12시간 동안 처리하는 것을 3회 반복하여 유근피 추출물을 추출하였고, 여과지를 이용하여 불순물을 제거하여 유근피 열수추출물을 얻었다. 유근피 열수추출물을 30% 메탄올, 50% 메탄올, 70% 메탄올, 100% 메탄올 순으로 극성을 높여가며 등용매 용출 조건으로 디아이온 HP-20 컬럼 크로마토그래피(Diaion HP-20 column chromatography)를 수행하여 3개의 분획물을 얻었다(Fr. E-1~E-3). 이 중 Fr. E-1을 70% 메탄올 등용매 용출 조건에 따른 세파덱스 LH-20 컬럼 크로마토그래피(sephadex LH-20 column chromatography)를 수행하여 울다비오시드 A 화합물(9㎎)을 분리하였다.Udon thunbergii was purchased from Ulmus davidiana Planch dried at the farm. After adding 1 L of purified water to 10 g dried rhizome, the mixture was treated with a semi-continuous low-temperature vacuum extractor at 25 ° C for 12 hours. The Rhizopus japonicus extract was extracted three times, and impurities were removed using a filter paper to obtain hot water extract . The diaion HP-20 column chromatography (Diaion HP-20 column chromatography) was performed on the isocratic elution conditions with 30% methanol, 50% methanol, 70% methanol and 100% Fractions were obtained (Fr. E-1 to E-3). Of these, Fr. E-1 was subjected to sephadex LH-20 column chromatography according to the elution conditions of 70% methanol and the like to separate the urodibioside A compound (9 mg).
<실시예 2. 울다비오시드 A 화합물의 물리화학적 구조 확인>Example 2: Identification of the physico-chemical structure of the urodavioside A compound [
Uldavioside A;Uldaviosidea;
연갈색분말;Light brown powder;
1H NMR 및 13C NMR 데이터는 하기 표 1 참조; ≪ 1 > H NMR and < 13 > C NMR data are shown in Table 1 below;
ESI-MS [M+H]+ m/z 423.1, C20H22O10. ESI-MS [M + H] + m / z 423.1, C 20 H 22 O 10 .
2.53 (1H, dd, J = 16.5, 8.3 Hz)2.84 (1H, dd, J = 16.5, 5.5 Hz)
2.53 (1H, dd, J = 16.5,8.3 Hz)
3.84 (1H, d, J = 9.6 Hz)4.07 (1H, d, J = 9.6 Hz)
3.84 (1H, d, J = 9.6 Hz)
b 1H NMR (600 MHz in CD3OD) spectroscopy data a 13 C NMR (150 MHz in CD 3 OD) spectroscopy data
b 1 H NMR (600 MHz in CD 3 OD) spectroscopy data
<< 실시예Example 3. 동물 세포의 배양> 3. Culture of animal cells>
본 발명의 울다비오시드 A 화합물의 활성을 확인하기 위해 동물 세포를 배양하였다. 이때 동물 세포는 근세포주인 C2C12, 섬유아세포주인 NIH3T3 세포를 이용하였다. 각각의 세포는 10% FBS(fetal bovine serum), 100U/㎖의 페니실린(penicillin) 및 100㎍/㎖의 스트렙토마이신(streptomycin)이 포함되어 있는 DMEM(Dulbecco's Modified Eagle's Medium) 배지를 넣고 37℃, 5% CO2 배양기에서 배양하였다. In order to confirm the activity of the cryovioside A compound of the present invention, animal cells were cultured. At this time, animal cells were used as myocyte host C2C12, fibroblast host NIH3T3 cells. Each of the cells was inoculated into DMEM (Dulbecco's Modified Eagle's Medium) medium containing 10% fetal bovine serum (FBS), 100 U / ml of penicillin and 100 μg / ml of streptomycin, % CO 2 incubator.
<실시예 4. 울다비오시드 A 화합물의 항산화 효과 확인>Example 4. Confirmation of antioxidative effect of the compound of cryptobiose A >
실시예 4-1. 울다비오시드 A 화합물의 과산화수소 생성 억제 확인 Example 4-1. Confirmation of hydrogen peroxide generation inhibition of urodibioside A compound
본 발명의 울다비오시드 A 화합물의 처리에 따른 항산화 효과를 확인하기 위해 과산화수소(H2O2) 검출 키트를 이용하였다. A hydrogen peroxide (H 2 O 2 ) detection kit was used to confirm the antioxidative effect of the cryoprecipitate A compound of the present invention.
상기 실시예 3에서 배양한 C2C12 및 NIH3T3 세포를 24웰 플레이트에 웰 당 5×105개 세포가 되도록 분주하여 24시간 동안 배양한 후, 울다비오시드 A 화합물을 1μM, 10μM 및 20μM이 되도록 세포에 처리하여 1시간 동안 전반응 시킨 다음 과산화수소를 생성하도록 글루코스 산화효소(glucose oxidase)를 7mU/㎖이 되도록 처리하여 24시간 동안 배양하였다. 이때 아무것도 처리하지 않은 C2C12 또는 NIH3T3 세포를 대조군으로 이용하였다. The C2C12 and NIH3T3 cells cultured in Example 3 were divided into 24 × 10 5 cells per well and cultured for 24 hours. Cells were seeded with 1 μM, 10 μM and 20 μM of the urodibioside A compound The cells were pre-reacted for 1 hour and then treated with glucose oxidase so as to produce hydrogen peroxide at a concentration of 7 mU / ml and cultured for 24 hours. At this time, C2C12 or NIH3T3 cells, which were not treated with either, were used as a control.
세포 배양액에 분비된 과산화수소를 H2O2 detection kit(biovision, USA)를 이용하여 측정하였다. 실험방법은 키트에서 제공되는 실험방법을 토대로 진행하였고, 그 결과를 도 2에 나타내었다. H 2 O 2 detection kit (biovision, USA) was used to measure the hydrogen peroxide secreted in the cell culture medium. The experimental method was carried out based on the experimental method provided in the kit, and the results are shown in FIG.
도 2에서 보여주듯이, C2C12(3A) 및 NIH3T3(3B) 세포 모두에서 본 발명의 울다비오시드 A 화합물 처리 농도 의존적으로 과산화수소의 양이 감소하는 것을 알 수 있었다. As shown in FIG. 2, it was found that the amount of hydrogen peroxide decreased in both of the C2C12 (3A) and NIH3T3 (3B) cells depending on the treatment concentration of the cryovioside A compound of the present invention.
실시예 4-2. 울다비오시드 A 화합물의 자유 라디칼(free radical) 소거능 확인 Example 4-2. Identification of free radical scavenging ability of urodibioside A compound
본 발명의 울다비오시드 A 화합물의 처리에 따른 항산화 효과를 확인하기 위해 DPPH(α,α-diphenyl-β-picrylhydrazyl) 라디칼 소거능을 확인하였다. DPPH 라디칼 소거능은 시료 내의 항산화 물질과 자유 라디칼인 DPPH 시약이 반응하여 자유 라디칼이 소거됨으로써 자색에서 노란색으로 탈색되는 원리를 이용한다.DPPH (?,? -Diphenyl-? -Picrylhydrazyl) radical scavenging ability was confirmed in order to confirm the antioxidative effect according to the treatment of the urobiosid A compound of the present invention. The DPPH radical scavenging ability is based on the principle that the antioxidant in the sample reacts with the DPPH reagent, which is a free radical, to decolorize from purple to yellow by eliminating free radicals.
에탄올에 용해시킨 0.4mM DPPH 용액 0.8㎖에 본 발명의 울다비오시드 A 화합물 0.2㎖을 혼합한 뒤 10분 동안 암실에서 반응시켰다. 이때, 울다비오시드 A 화합물은 최종 농도가 1, 10, 20 및 50uM이 되도록 처리하였고, 대조군으로 아스코르브산(ascorbic acid) 및 부틸히드록시아니솔(butylated hydroxyanisol, BHA)을 동일한 농도로 처리하였다. 반응이 끝난 후 517㎚에서 흡광도 값을 측정한 후, 하기 식을 이용하여 DPPH 라디칼 소거능을 계산하였고, 그 결과를 도 3 및 표 2에 나타내었다. 0.2 ml of the compound of the present invention was mixed with 0.8 ml of a 0.4 mM DPPH solution dissolved in ethanol, followed by reaction in a dark room for 10 minutes. At this time, the urodibioside A compound was treated to give final concentrations of 1, 10, 20 and 50 uM, and ascorbic acid and butylated hydroxyanisol (BHA) were treated at the same concentration as a control group. After the reaction was completed, the absorbance was measured at 517 nm, and the DPPH radical scavenging activity was calculated using the following equation. The results are shown in FIG. 3 and Table 2.
DPPH 라디칼 소거능(%)=(1-시료군 흡광도-공시료(blank) 흡광도)×100DPPH radical scavenging activity (%) = (1-sample group absorbance - blank absorbance) × 100
(IC50, uM)Free radical scavenging ability
(IC 50 , uM)
도 3에서 보여주듯이, 본 발명의 울다비오시드 A 화합물의 DPPH 라디칼 소거능이 1uM의 낮은 농도에서는 대조군으로 사용된 아스코르브산에 비해 월등히 높은 것으로 확인되었으며, 10uM 이상의 농도에서는 아스코르브산과 비슷하게 나타났다. 반면, 또 다른 대조군인 부틸히드록시아니솔(BHA)과 비교하면, 본 발명의 울다비오시드 A 화합물의 DPPH 라디칼 소거능이 모든 농도에서 월등히 높음을 알 수 있었다. As shown in FIG. 3, the DPPH radical scavenging ability of the urobiosid A compound of the present invention was significantly higher than that of ascorbic acid used as a control at a concentration of 1 uM, and was similar to that of ascorbic acid at a concentration of 10 uM or more. On the other hand, the DPPH radical scavenging ability of the urobiosid A compound of the present invention was significantly higher at all concentrations than the other control group, butylhydroxyanisole (BHA).
또한, 상기 표 2에서 보여주듯이, 본 발명의 울다비오시드 A 화합물의 DPPH 라디칼 소거능에 대한 IC50 값이, 대조군으로 사용한 아스코르브산과 유사하며, 부틸히드록시아니솔(BHA)보다 더 낮은 것을 확인하였다. In addition, as shown in Table 2, it was confirmed that the IC 50 value against the DPPH radical scavenging ability of the culdoubioside A compound of the present invention was similar to that of ascorbic acid used as the control group and lower than that of butylhydroxyanisole (BHA) .
이를 통해, 본 발명의 울다비오시드 A의 화합물의 자유 라디칼 소거능의 활성이 아스코르브산과 유사한 수준으로 매우 우수하다는 것을 알 수 있었다. As a result, it was found that the free radical scavenging activity of the compound of the present invention was very good, similar to that of ascorbic acid.
실시예Example 4-3. 4-3. 울다비오시드Cryobio seed A 화합물의 총 A total of compounds 항산화능Antioxidant ability (total antioxidant capacity) 확인(total antioxidant capacity)
본 발명의 울다비오시드 A 화합물의 총 항산화능(total antioxidant capacity)은 Biovision 사의 total antioxidant capacity colorimetric kit(항산화 활성에 의해 Cu2+가 Cu+로 변환되는 것을 측정)를 이용하여 측정하였고, 실험방법은 Biovision사에서 제공한 실험방법에 따라 수행하였다.The total antioxidant capacity of the cryoprecipitate A compound of the present invention was measured using a total antioxidant capacity colorimetric kit of Biovision Co. (measuring the conversion of Cu 2+ to Cu + by antioxidant activity) Were performed according to the experimental method provided by Biovision.
표준곡선으로 이용한 트롤록스(trolox, 6-hydroxy-2,5,7,8-tetramethylchroman-2-carbocylic acid)는 농도별로 희석하고, 울다비오시드 A 화합물 또는 대조군으로 사용한 아스코르브산 및 부틸히드록시아니솔은 10uM이 되도록 준비한 후, 각각의 샘플에 Cu2+를 10㎕씩 넣고 상온에서 90분 동안 반응 시킨 후 570㎚에서 흡광도 값을 측정하였다. Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carbocylic acid) used as a standard curve was diluted by concentration and ascorbic acid used as a cobaltoside A compound or a control group and butylhydroxy After preparing the sole for 10 μM, 10 μl of Cu 2+ was added to each sample, reacted at room temperature for 90 minutes, and the absorbance value was measured at 570 nm.
트롤록스의 농도별 흡광도 값을 이용해 표준곡선을 확보하고, 확보한 표준곡선을 통해 각 시료의 총 항산화능을 계산하여 그 결과를 도 4에 나타내었다. A standard curve was obtained by using the absorbance value of each concentration of Trolox, and the total antioxidative capacity of each sample was calculated through the obtained standard curve. The results are shown in FIG.
도 4에서 보여주듯이, 본 발명의 울다비오시드 A 화합물의 총 항산화 능력은 대조군으로 사용한 부틸히드록시아니솔 보다 월등히 높으며, 아스코르브산과 비슷한 수준으로 나타났다. As shown in FIG. 4, the total antioxidative capacity of the compound of the present invention was significantly higher than that of butylhydroxyanisole used as a control, and was similar to that of ascorbic acid.
이들 결과를 통해, 본 발명의 울다비오시드 A 화합물이 현저히 우수한 항산화 활성을 가지고 있음을 알 수 있었다. From these results, it can be seen that the compound of the present invention has a remarkably superior antioxidative activity.
<실시예 5. 울다비오시드 A 화합물의 세포 독성 확인>Example 5: Cytotoxicity of cryovioside A compound < RTI ID = 0.0 >
본 발명의 울다비오시드 A 화합물에 의한 세포 독성 여부를 MTT 어세이 방법을 이용해 확인하였다. The cytotoxicity of the cryovioside A compound of the present invention was confirmed by the MTT assay method.
상기 실시예 3에서 배양한 C2C12 및 NIH3T3 세포를 48웰 플레이트에 웰 당 1×105개 세포가 되도록 분주하여 24시간 동안 배양한 후, 0.5% FBS(fetal bovine serum), 100U/㎖의 페니실린(penicillin) 및 100㎍/㎖의 스트렙토마이신(streptomycin)이 포함되어 있는 DMEM(Dulbecco's Modified Eagle's Medium) 배지를 넣고 18시간 동안 배양하였다. 18시간 배양 후, 울다비오시드 A 화합물을 1μM 및 10μM로 처리하고, 24시간 동안 배양하였다. 이때 아무것도 처리하지 않은 C2C12 및 NIH3T3 세포를 대조군으로 이용하였다. 24시간 후에 세포에 100㎍/㎖의 농도로 MTT 용액을 처리하고 37℃에서 3시간 반응시킨 후 배양액을 제거하고 형성된 포마잔(formazan) 침전물을 DMSO(dimethyl sulfoxide) 200㎕로 녹이고 570㎚에서 흡광도를 측정하였고, 그 결과를 도 5에 나타내었다. The C2C12 and NIH3T3 cells cultured in the above Example 3 were seeded in a 48 well plate at 1 x 10 < 5 > cells Cells were cultured for 24 hours, and then cultured in DMEM (Dulbecco's Modified Eagle's Medium) containing 0.5% FBS (fetal bovine serum), 100 U / ml penicillin and 100 μg / ml streptomycin ) Medium and incubated for 18 hours. After 18 hours of incubation, the cryovioside A compound was treated with 1 [mu] M and 10 [mu] M and cultured for 24 hours. At this time, C2C12 and NIH3T3 cells, which were not treated with anything, were used as a control. After 24 hours, the cells were treated with MTT solution at a concentration of 100 μg / ml and reacted at 37 ° C. for 3 hours. The culture solution was removed, and the formazan precipitate formed was dissolved in 200 μl of DMSO (dimethyl sulfoxide) And the results are shown in Fig.
도 5에서 보여주듯이, 울다비오시드 A 화합물을 처리한 C2C12(3A) 및 NIH3T3(3B) 세포의 생존율이 대조군에 비해 증가하였다. 이를 통해, 본 발명의 울다비오시드 A 화합물이 세포 독성을 나타내지 않음을 알 수 있었다. As shown in Fig. 5, the survival rates of C2C12 (3A) and NIH3T3 (3B) cells treated with the cucurbitidoside A compound were increased compared to the control. As a result, it was found that the cryovioside A compound of the present invention did not show cytotoxicity.
<제제예 1. 약학적 제제>≪ Formulation Example 1 >
제제예 1-1. 정제의 제조Formulation Example 1-1. Manufacture of tablets
본 발명의 울다비오시드 A 화합물 200g을 락토즈 175.9g, 감자전분 180g 및 콜로이드성 규산 32g과 혼합하였다. 이 혼합물에 10% 젤라틴 용액을 첨가시킨 후, 분쇄하여 14 메쉬체를 통과시켰다. 이것을 건조시키고 여기에 감자전분 160g, 활성 50g 및 스테아린산 마그네슘 5g을 첨가해서 얻은 혼합물을 정제로 만들었다. 200 g of the compound of the present invention was mixed with 175.9 g of lactose, 180 g of potato starch and 32 g of colloidal silicic acid. A 10% gelatin solution was added to the mixture, followed by pulverization and passed through a 14-mesh sieve. This was dried, and a mixture obtained by adding 160 g of potato starch, 50 g of activity and 5 g of magnesium stearate was made into tablets.
제제예 1-2. 주사액제의 제조Formulation Example 1-2. Injection preparation
본 발명의 울다비오시드 A 화합물 1g, 염화나트륨 0.6g 및 아스코르브산 0.1g을 증류수에 용해시켜서 100㎖를 만들었다. 이 용액을 병에 넣고 20℃에서 30분간 가열하여 멸균시켰다. 1 g of the compound of the present invention, 0.6 g of sodium chloride and 0.1 g of ascorbic acid were dissolved in distilled water to make 100 ml. This solution was placed in a bottle and sterilized by heating at 20 DEG C for 30 minutes.
<제제예 2. 화장료 조성물의 제조>≪ Preparation Example 2: Preparation of cosmetic composition >
제제예 2-1. 크림 제조Formulation Example 2-1. Cream manufacturing
본 발명의 울다비오시드 A 화합물 5g에 시토스테롤 4g, 폴리글리세릴 2-올레이트 3g, 세라마이드 0.7g, 세테아레스-4 2g, 콜레스테롤 3g, 디세틸포스페이트 0.4g, 농글리세린 5.0g, 선플라우어오일 22g, 카르복시비닐폴리머 0.5g, 트리에탄올아민 0.5g, 방부제 및 향료 미량 및 정제수를 총 무게가 100g이 되도록 혼합하였고, 통상의 크림 제조 방법에 따라 영양 크림을 제조하였다. 4 g of sitosterol, 3 g of polyglyceryl 2-olate, 0.7 g of ceramide, 2 g of cetearate-4, 3 g of cholesterol, 0.4 g of dicetyl phosphate, 5.0 g of concentrated glycerin, 22 g of Spluaru oil 0.5 g of carboxyvinyl polymer, 0.5 g of triethanolamine, a small amount of preservative and perfume, and purified water were mixed to a total weight of 100 g, and a nutritional cream was prepared according to a conventional cream preparation method.
제제예 2-2. 화장수 제조Formulation Example 2-2. Lotion manufacturing
95% 에탄올 8g에 폴리피롤리돈 0.05g, 올레일알콜 0.1g, 폴리옥시에틸렌모노올레이트 0.2g, 향료 0.2g, 파라옥시안식향산메틸에스테르 0.1g, 소량의 산화방지제, 소량의 색소를 혼합 용해하였다. 본 발명의 울다비오시드 A 화합물 0.05g, 글리세린 5g을 정제수 85.33g에 용해한 것에 상기 혼합액을 첨가한 후 교반하여 혼합 생약의 추출물을 함유하는 화장수를 제조하였다.0.05 g of polypyrrolidone, 0.1 g of oleyl alcohol, 0.2 g of polyoxyethylene monooleate, 0.2 g of perfume, 0.1 g of p-hydroxybenzoic acid methyl ester, a small amount of antioxidant and a small amount of dye were mixed and dissolved in 8 g of 95% ethanol. 0.05 g of the urodibioside A compound of the present invention and 5 g of glycerin were dissolved in 85.33 g of purified water. The mixture was added to the mixture and stirred to prepare a lotion containing the extract of the mixed herb.
제제예 2-3. 유액 제조Preparation Example 2-3. Emulsion manufacturing
세틸알코올 1.2g, 스쿠알란 10g, 바세린 2g, 파라옥시안식향산에틸에스테르 0.2g, 글리세린모노에스테아레이드 1g, 폴리옥시에틸렌(20몰부가)모노올레이트 1g 및 향료 0.1g을 70℃에서 가열혼합용해하고, 본 발명의 울다비오시드 A 화합물 0.5g, 디프로필렌글리콜 5g, 폴리에틸렌글리콜-1500 2g, 트리에탄올아민 0.2g, 정제수 76.2g을 75℃로 가열해서 용해시켰다. 양자를 혼합하여 유화시킨 후 냉각하여 수중유(Oil-in-Water, O/W)형의 유액을 제조하였다.1.2 g of cetyl alcohol, 10 g of squalane, 2 g of vaseline, 0.2 g of p-hydroxybenzoic acid ethyl ester, 1 g of glycerin monoestearate, 1 g of polyoxyethylene (20 mols of addition) monooleate and 0.1 g of perfume were heated and mixed at 70 캜 0.5 g of the compound of the present invention, 5 g of dipropylene glycol, 2 g of polyethylene glycol-1,500, 0.2 g of triethanolamine and 76.2 g of purified water were dissolved by heating at 75 占 폚. The mixture was emulsified by mixing and then cooled to prepare an oil-in-water (O / W) type emulsion.
제제예 2-4. 미용액 제조Formulation Example 2-4. Serum preparation
95% 에틸알콜 5g에 폴리옥시에틸렌솔비탄모노올레이트 1.2g, 키툴로오즈 0.3g, 히야론산나트륨 0.2g, 비타민 E-아세테이트 0.2g, 감초산 나트륨 0.2g, 파라옥시안식향산에틸에스테르 0.1g, 본 발명의 울다비오시드 A 화합물 1g 및 적량의 색소를 혼합하여 미용액을 제조하였다.To 5 g of 95% ethyl alcohol, 1.2 g of polyoxyethylene sorbitan monooleate, 0.3 g of quitrose, 0.2 g of sodium hyaluronate, 0.2 g of vitamin E-acetate, 0.2 g of sodium permanganate, 0.1 g of paraoxybenzoic acid ethyl ester, 1 g of the compound of the present invention was mixed with an appropriate amount of coloring matter to prepare a serum.
<제제예 3. 식품 제조>≪ Formulation example 3. Food production >
제제예 3-1. 조리용 양념의 제조Formulation Example 3-1. Manufacture of cooking seasonings
본 발명의 울다비오시드 A 화합물을 조리용 양념에 1중량%로 첨가하여 건강 증진용 조리용 양념을 제조하였다. The cryobioside A compound of the present invention was added to the cooking seasoning at 1 wt% to prepare a cooking sauce for health promotion.
제제예 3-2. 밀가루 식품의 제조Formulation Example 3-2. Manufacture of flour food products
본 발명의 울다비오시드 A 화합물을 밀가루에 0.1중량%로 첨가하고, 이 혼합물을 이용하여 빵, 케이크, 쿠키, 크래커 및 면류를 제조하여 건강 증진용 식품을 제조하였다. A food for health promotion was prepared by adding 0.1% by weight of the compound of the present invention to wheat flour, and preparing bread, cake, cookie, cracker and noodle by using this mixture.
제제예 3-3. 스프 및 육즙(gravies)의 제조Formulation Example 3-3. Manufacture of soups and gravies
본 발명의 울다비오시드 A 화합물을 스프 및 육즙에 0.1중량%로 첨가하여 건강 증진용 스프 및 육즙을 제조하였다. The health-enhancing soup and juice were prepared by adding 0.1% by weight of the compound of the present invention to the soup and the juice.
제제예 3-4. 유제품(dairy products)의 제조Formulation Example 3-4. Manufacture of dairy products
본 발명의 울다비오시드 A 화합물을 우유에 0.1중량%로 첨가하고, 상기 우유를 이용하여 버터 및 아이스크림과 같은 다양한 유제품을 제조하였다. The dulabioside A compound of the present invention was added to milk in an amount of 0.1% by weight, and various dairy products such as butter and ice cream were prepared using the milk.
제제예 3-5. 야채주스의 제조Formulation Example 3-5. Manufacture of vegetable juices
본 발명의 울다비오시드 A 화합물 0.5g을 토마토주스 또는 당근주스 1,000㎖에 가하여 건강 증진용 야채주스를 제조하였다. 0.5 g of the compound of the present invention was added to 1,000 ml of tomato juice or carrot juice to prepare vegetable juice for health promotion.
제제예 3-6. 과일주스의 제조Formulation Example 3-6. Manufacture of fruit juices
본 발명의 울다비오시드 A 화합물 0.1g을 사과주스 또는 포도주스 1,000㎖에 가하여 건강 증진용 야채주스를 제조하였다. 0.1 g of the compound of the present invention was added to 1,000 ml of apple juice or grape juice to prepare vegetable juice for health promotion.
Claims (10)
[화학식 1]
1. An antioxidative composition comprising, as an active ingredient, a cryoprecipitate A compound represented by the following formula (1).
[Chemical Formula 1]
상기 조성물은 약학적으로 허용 가능한 담체 또는 부형제를 포함하는 약학적 조성물인 것을 특징으로 하는 항산화 조성물. 3. The method of claim 2,
Wherein said composition is a pharmaceutical composition comprising a pharmaceutically acceptable carrier or excipient.
상기 약학적 조성물은 울다비오시드 A 화합물이 조성물 총 중량을 기준으로 0.001중량% 내지 50중량%로 첨가되는 것을 특징으로 하는 항산화 조성물.3. The method of claim 2,
Wherein said pharmaceutical composition is added in an amount of from 0.001% to 50% by weight, based on the total weight of the composition, of the urodiboside A compound.
상기 약학적 조성물은 활성산소에 의해 생성되는 산화물들에 기인하는 질환의 예방 또는 치료를 위하여 사용되는 것을 특징으로 하는 항산화 조성물. The method according to claim 2 or 3,
Wherein said pharmaceutical composition is used for the prevention or treatment of diseases caused by oxides produced by active oxygen.
상기 활성산소에 의해 생성되는 산화물들에 기인하는 질환은 노화, 만성알콜중독, 죽상동맥경화증, 암, 관상심장질환, 백내장, 당뇨병, 다운증후군, 간염, 허혈이나 재관류성 손상, 류마티스성 관절염, 관절염, 신부전증, 각종 퇴행성 신경질환, 뇌졸중 발작, 아토피성 피부염, 기관지염, 간질, 만성폐쇄성 질환, 당뇨병성 혈관합병증 및 심근경색으로 이루어진 군에서 선택되는 1종 이상의 질환인 것을 특징으로 하는 항산화 조성물. 5. The method of claim 4,
The diseases caused by the active oxygen-induced oxides include but are not limited to aging, chronic alcoholism, atherosclerosis, cancer, coronary heart disease, cataract, diabetes, Down syndrome, hepatitis, ischemia or reperfusion injury, rheumatoid arthritis, Wherein the antioxidant composition is at least one disease selected from the group consisting of renal failure, various degenerative nerve diseases, stroke, atopic dermatitis, bronchitis, epilepsy, chronic obstructive disease, diabetic vascular complication, and myocardial infarction.
상기 조성물은 화장료 조성물인 것을 특징으로 하는 항산화 조성물. The method according to claim 1,
Wherein the composition is a cosmetic composition.
상기 화장료 조성물은 울다비오시드 A 화합물이 조성물 총 중량을 기준으로 0.001중량% 내지 50중량%로 첨가되는 것을 특징으로 하는 항산화 조성물.The method according to claim 6,
Wherein the cosmetic composition is added in an amount of 0.001% to 50% by weight based on the total weight of the composition of the cryovioside A compound.
상기 화장료 조성물은 피부 노화 방지용인 것을 특징으로 하는 항산화 조성물. 8. The method according to claim 6 or 7,
Wherein the cosmetic composition is for preventing skin aging.
상기 조성물은 항산화 효과를 갖는 건강기능식품인 것을 특징으로 하는 항산화 조성물. The method according to claim 1,
Wherein the composition is a health functional food having an antioxidative effect.
상기 건강기능식품은 울다비오시드 A 화합물이 조성물 총 중량을 기준으로 0.001중량% 내지 50중량%로 첨가되는 것을 특징으로 하는 항산화 조성물.10. The method of claim 9,
Wherein said health functional food is added in an amount of 0.001 wt% to 50 wt% based on the total weight of the composition of the urodavioside A compound.
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