KR20100092626A - Skin inflammation, cancer, and photoaging preventive composition comprising 7,3',4'-trihydroxyisoflavone - Google Patents
Skin inflammation, cancer, and photoaging preventive composition comprising 7,3',4'-trihydroxyisoflavone Download PDFInfo
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- KR20100092626A KR20100092626A KR1020090011837A KR20090011837A KR20100092626A KR 20100092626 A KR20100092626 A KR 20100092626A KR 1020090011837 A KR1020090011837 A KR 1020090011837A KR 20090011837 A KR20090011837 A KR 20090011837A KR 20100092626 A KR20100092626 A KR 20100092626A
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- trihydroxyisoflavone
- composition
- skin
- weight
- active ingredient
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A23V2200/00—Function of food ingredients
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Abstract
Description
본 발명은 대두 및 콩과 식물의 주요 구성 아이소플라본인 다이드제인 (daidzein)의 대사체인 7,3',4'-트리하이드록시아이소플라본 (7,3',4'-trihydroxyisoflavone)을 유효성분으로 포함하는 피부염증, 피부암 및 피부광노화 예방 및 치료용 조성물에 관한 것으로, 더욱 상세하게는 본 발명은 자외선에 의해 증가된 싸이클로옥시게나제-2(cyclooxygenase-2, COX-2)의 발현 저해 및 2단계 마우스 종양 형성 억제 효과를 나타내어 피부 염증, 피부손상 및 피부 암 예방 및 치료 효과를 나타내며 이와 더불어 자외선에 의해 증가된 메트릭스 메탈로프로티아제-1(Matrix Metalloproteinase-1, MMP-1) 활성 억제를 나타내어 피부 광 노화 예방 및 치료 효과가 있는 7,3',4'-트리하이드록시아이소플라본을 사용하는 예방 및 치료 조성물에 관한 것이다.The present invention is an active ingredient of 7,3 ', 4'-trihydroxyisoflavone (7,3', 4'-trihydroxyisoflavone) which is a metabolite of daidzein, which is an isoflavone which is a major component of soybeans and legumes. The present invention relates to a composition for preventing and treating skin inflammation, skin cancer and skin photoaging, and more particularly, the present invention relates to inhibition of expression of cyclooxygenase-2 (COX-2) increased by ultraviolet rays and Inhibits the formation of two-stage mouse tumors and prevents and treats skin inflammation, skin damage and skin cancer. In addition, it inhibits the activity of matrix metalloproteinase-1 (MMP-1) that is increased by ultraviolet rays. The present invention relates to a prophylactic and therapeutic composition using 7,3 ', 4'-trihydroxyisoflavone having a skin light aging prevention and treatment effect.
최근 들어 현대인의 환경오염 노출과 스트레스의 증가, 식생활 변화에 따라 우리 몸의 면역 체계가 교란되고 따라서 각종 피부병 질환이 급증하고 있다. Recently, the immune system of our body is disturbed by the exposure of environmental pollution, the increase of stress, and the change of diet of the modern people, and thus various skin diseases are increasing rapidly.
태양 빛은 가시광선, 자외선, 적외선으로 구성된다. 이중 자외선은 체내에서 비타민D를 합성하고, 살균작용의 역할이 있으나, 피부염, 피부암, 일광 화상, 피부노화, 건조, 잔주름 등을 생기게도 한다. 자외선(Ultraviolet, UV)은 파장길이에 따라 A,B,C의 3가지로 나뉘는데, 이 중 UVC는 오존층에서 차단되고 UVA와 UVB가 피부에 영향을 미친다. 특히 중간 파장인 UVB (290-320 nm)는 급성이나 만성적으로 노출되었을 경우, 심각한 피부 손상을 야기하는데, 주로 피부에 염증을 일으켜 홍반이나 수포를 만드는 일광화상을 일으킨다. 과다하게 조사했을 경우 피부 염증을 일으켜 암을 유발한다고 알려져 있다(Oro, A.E. et al., Science, 276:817-821, 1997; Kim HJ et al., Apoptosis 9:449-456, 2004). Sun light is composed of visible, ultraviolet and infrared light. UV rays synthesize vitamin D in the body and play a role in sterilization, but may also cause dermatitis, skin cancer, sunburn, skin aging, drying, and fine lines. Ultraviolet (UV) is divided into three types, A, B, and C, depending on the wavelength, among which UVC is blocked in the ozone layer, and UVA and UVB affect the skin. In particular, the medium wavelength UVB (290-320 nm) causes severe skin damage when exposed to acute or chronic exposure, causing sunburn, mainly causing inflammation of the skin and erythema or blisters. Overexposure is known to cause skin inflammation and cancer (Oro, AE et al., Science , 276: 817-821, 1997; Kim HJ et al., Apoptosis 9: 449-456, 2004).
염증물질이 과도하게 생성될 경우, 과도한 면역반응을 야기하여 각종 염증성 질환이나 피부 손상을 유발하게 된다. 염증에 중요하게 관여하는 효소인 싸이클로옥시게나제-2(cyclooxygenase, 이하 COX-2라 함)는 아라키돈산(arachidonic acid)을 염증성 물질인 프로스타글란딘류(prostaglandins)를 생성하는 대표적인 효소이다(Hla T and Neilson K. Proc Natl Acad Sci U S A. 89(16):7384-8, 1992, Grewe M et al., J Invest Dermatol. 101(4):528-31, 1993; Joyce E. Rundhaug et al., Mol Carcinog., 46:692-698, 2007). 최근 연구에서 여러 종류의 암종에서 COX-2의 활성이 증가되어 있음이 보고되었다(Dubois RN, FASEB J, 12:1063-73, 1998, Brecher AR., J Drugs Dermatol., 1(1):44-7, 2002). 이에, 피부염증 및 피부손상 예방 및 치료제로써 COX-2 발현을 억제시킬 수 있는 물질의 개발이 요구되고 있다.When excessively inflammatory substances are produced, it may cause excessive immune response, causing various inflammatory diseases and skin damage. Cyclooxygenase-2 (hereinafter referred to as COX-2), an enzyme that is important in inflammation, is a representative enzyme that produces arachidonic acid (prostaglandins) as an inflammatory substance (Hla T and Neilson K. Proc Natl Acad Sci USA . 89 (16): 7384-8, 1992, Grewe M et al., J Invest Dermatol . 101 (4): 528-31, 1993; Joyce E. Rundhaug et al., Mol Carcinog. , 46: 692-698, 2007). Recent studies have reported increased COX-2 activity in several types of carcinoma (Dubois RN, FASEB J , 12: 1063-73, 1998, Brecher AR., J Drugs Dermatol ., 1 (1): 44 -7, 2002). Accordingly, there is a need for development of a substance capable of inhibiting COX-2 expression as an agent for preventing and treating skin inflammation and skin damage.
피부의 노화는 광노화와 자연노화로 나눈다. 광노화의 주요한 원인은 반복적인 자외선의 노출이며 자외선에 의해 생성되는 염증성 싸이토카인 (cytokine) 들은 피부에서 콜라겐 (collagen) 의 합성을 억제하며, 콜라겐을 분해하는 효소들의 발현을 증가시켜 불규칙적인 콜라겐을 형성한다. 이러한 특징적인 변화들은 광노화를 유도하며 피부홍반, 거칠기, 깊은 주름 및 흑화를 유도하는 것으로 알려져 있다 (Fisher, G. J et al., N. Engl. J. Med, 337:1419-1428., 1997; Moon HJ et al., Biol Pharm Bull. 31(2):284-9, 2008).Aging of the skin is divided into photoaging and natural aging. The main cause of photoaging is repeated exposure to ultraviolet light, and inflammatory cytokines produced by ultraviolet light inhibit the synthesis of collagen in the skin and increase the expression of enzymes that break down collagen, forming irregular collagen. . These characteristic changes induce photoaging and are known to induce skin erythema, roughness, deep wrinkles and blackening (Fisher, G. J et al., N. Engl. J. Med , 337: 1419-1428., 1997 Moon HJ et al., Biol Pharm Bull . 31 (2): 284-9, 2008).
사람의 피부 중 주요한 구성 성분은 콜라겐이며 특히 type I 콜라겐은 80 %, type III 콜라겐은 15 % 를 차지한다. 정상 피부에서는 type I 콜라겐의 합성과 그 분해 효소인 MMP-1이 균형을 이루고 있다. 그러나 광노화된 피부에서는 type I, III 콜라겐의 합성이 저하되고, MMP-1의 활성이 증가되어 있으며 이러한 변화는 콜라겐의 합성과 분해의 불균형을 가져와 피부의 깊은 주름을 가져온다. (Talwar, J. S, J. Invest. Dermatol, 105: 285-290, 1995; Kim S et, al., J Lipid Res., Dec;49(12):2571-81, 2008) 따라서 피부 광노화의 예방 및 치료제로써 MMP-1 활성을 억제 시킬 수 있는 물질의 개발이 요구 된다. The major constituent of human skin is collagen, especially 80% of type I collagen and 15% of type III collagen. In normal skin, the synthesis of type I collagen and its degrading enzyme, MMP-1, are balanced. However, in photo-aged skin, the synthesis of type I and III collagen is decreased, and the activity of MMP-1 is increased, and this change leads to an imbalance between collagen synthesis and degradation, resulting in deep wrinkles of the skin. (Talwar, J. S, J. Invest. Dermatol, 105: 285-290, 1995; Kim S et, al., J Lipid Res ., Dec; 49 (12): 2571-81, 2008). As a prophylactic and therapeutic agent, development of a substance capable of inhibiting MMP-1 activity is required.
본 발명은 상기 종래기술의 문제점을 해결하고 상기 필요성에 의하여 안출된 것으로서 , 본 발명의 목적은 피부염증, 피부암 및 피부광노화 예방 및 치료제를 제공하는 것이다. The present invention solves the problems of the prior art, and the object of the present invention is to provide an agent for preventing and treating skin inflammation, skin cancer and skin photoaging.
상기 목적을 달성하기 위하여, 본 발명은 유효량의 하기 화학식 1의 7,3',4'-트리하이드록시아이소플라본을 유효성분으로 포함하는 약학 조성물을 제공한다.In order to achieve the above object, the present invention provides a pharmaceutical composition comprising an effective amount of 7,3 ', 4'-trihydroxyisoflavone of the formula (1) as an active ingredient.
[화학식 1][Formula 1]
본 발명의 일 구체예에 있어서, 상기 조성물은 피부염증, 피부암 및 피부광노화로부터 선택된 질환의 치료 또는 예방에 효과적이나, 이에 한정되지 아니한다.In one embodiment of the invention, the composition is effective in the treatment or prevention of diseases selected from skin inflammation, skin cancer and skin photoaging, but is not limited thereto.
또한 본 발명은 유효량의 하기 화학식 1의 7,3',4'-트리하이드록시아이소플라본을 유효성분으로 포함하는 암 예방 또는 치료용 조성물을 제공한다.In another aspect, the present invention provides a composition for preventing or treating cancer, comprising an effective amount of 7,3 ', 4'-trihydroxyisoflavone of the general formula (1) as an active ingredient.
[화학식 1][Formula 1]
본 발명의 일 구체예에 있어서, 상기 조성물은 피부암에 대하여 항암 효과를 가지는 것이 바람직하나 이에 한정되지 아니한다.In one embodiment of the present invention, the composition is preferably one having an anticancer effect against skin cancer, but is not limited thereto.
또한 본 발명은 하기 화학식 1의 7,3',4'-트리하이드록시아이소플라본을 유효성분으로 포함하는 식품 조성물을 제공한다.In another aspect, the present invention provides a food composition comprising 7,3 ', 4'-trihydroxyisoflavone of the general formula (1) as an active ingredient.
또 본 발명은 In addition, the present invention
하기 화학식 1의 7,3',4'-트리하이드록시아이소플라본을 유효성분으로 포함하는 화장료 조성물을 제공한다.It provides a cosmetic composition comprising 7,3 ', 4'-trihydroxyisoflavone of the formula (1) as an active ingredient.
[화학식 1][Formula 1]
본 발명자들은 인체 안전성이 확보된 피부 염증 예방 및 치료제에 대하여 연구하던 중, 7,3',4'-트리하이드록시아이소플라본이 자외선에 의해 증가한 COX-2 발현과 종양 형성 및 MMP-1 활성을 효과적으로 억제할 수 있음을 확인하였으며, 이를 토대로 본 발명을 완성하게 되었다.The inventors of the present invention, while researching a preventive and therapeutic agent for skin inflammation, in which human safety is ensured, 7,3 ', 4'-trihydroxyisoflavones have been shown to increase COX-2 expression, tumor formation, and MMP-1 activity by UV rays. It was confirmed that the present invention can be effectively suppressed, and thus, the present invention has been completed.
본 발명은 7,3',4'-트리하이드록시아이소플라본을 유효성분으로 포함하는 피부염증, 피부암 및 피부광노화 예방 및 치료제에 관한 것이다. 7,3',4'-트리하이드록시아이소플라본은 시판되고 있는 화합물을 용이하게 구입 가능 한 것이다.The present invention relates to a preventive and therapeutic agent for skin inflammation, skin cancer and skin photoaging comprising 7,3 ', 4'-trihydroxyisoflavone as an active ingredient. 7,3 ', 4'-trihydroxyisoflavone is a commercially available compound readily available.
본 발명의 피부염증, 피부암 및 피부광노화 예방 및 치료제에 포함되는 7,3',4'-트리하이드록시아이소플라본 함량은, 예방 및 치료제의 사용방법, 복용자의 상태, 질환의 종류 및 질환의 중증정도에 따라 바람직하게 조절하는 것이 좋다. 본 발명의 조성물에서 7,3',4'-트리하이드록시아이소플라본의 유효함량은 0.01 내지 50 중량% 일 수 있으나, 이에 한정되는 것은 아니다. 그러나, 그 함량이 0.01 중량% 미만인 경우 항염증과 피부손상을 방지 효과가 미비할 수 있으며, 50 중량% 초과하는 경우 사용량 대비 효과 상승률이 낮아 비경제적일 수 있다.7,3 ', 4'-trihydroxyisoflavone content included in the prophylaxis and treatment of skin inflammation, skin cancer and skin photoaging of the present invention, the method of use of the prophylaxis and treatment, the condition of the user, the type of disease and the severity of the disease It is good to adjust suitably according to a degree. The effective content of 7,3 ', 4'-trihydroxyisoflavone in the composition of the present invention may be 0.01 to 50% by weight, but is not limited thereto. However, if the content is less than 0.01% by weight may be ineffective anti-inflammatory and skin damage prevention, if the content exceeds 50% by weight can be uneconomical low effect increase rate.
또한 본 발명의 실시예에 있어서, 상기 유효량은 10μM에서 1mM인 것이 바람 직하나 이에 한정되지 아니한다. In addition, in the embodiment of the present invention, the effective amount is preferably 10μM to 1mM, but is not limited thereto .
본 발명의 피부염증, 피부암 및 피부광노화 예방 및 치료제는, 유효성분 이외에 약제학적으로 허용가능한 담체, 희석제 또는 부형제를 더욱 포함할 수 있으며, 이때 유효성분의 함량은 전체 조성물에 0.001 내지 99 중량%인 것이 좋다. 사용가능한 담체, 부형제 또는 희석제로는, 락토즈, 덱스트로즈, 수크로즈, 솔비톨, 만니톨, 자이리톨, 에리스리톨, 말티톨, 전분, 아카시아 고무, 알지네이트, 젤라틴, 칼슘 포스페이트, 칼슘 실리케이트, 셀룰로즈, 메틸 셀룰로즈, 미정질 셀룰로즈, 폴리비닐피롤리돈, 물, 메틸하이드록시벤조에이트, 프로필하이드록시벤조에이트, 탈크, 마그네슘 스테아레이트 및 광물유가 있으며, 이들은 1종이상 사용될 수 있다. 또한 예방 및 치료제가 약제인 경우 충진제, 항응집제, 윤활제, 습윤제, 향료, 유화제 또는 방부제 등을 더욱 포함할 수 있다.The skin inflammation, skin cancer and skin photoaging prevention and treatment agent of the present invention may further comprise a pharmaceutically acceptable carrier, diluent or excipient in addition to the active ingredient, wherein the content of the active ingredient is 0.001 to 99% by weight of the total composition It is good. Carriers, excipients or diluents which may be used include lactose, dextrose, sucrose, sorbitol, mannitol, ziitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, Microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil, which may be used one or more. In addition, when the prophylactic and therapeutic agent is a medicament, it may further include fillers, anti-coagulants, lubricants, wetting agents, fragrances, emulsifiers or preservatives.
또한 본 발명의 유효성분으로 포함하는 피부염증, 피부암 및 피부광노화 예방 및 치료제는, 약제, 식품, 식품첨가제, 음료, 음료첨가제 또는 화장품 조성물 등으로 사용될 수 있다. 암 예방 조성물은 약제로 사용되는 경우 암 예방제일 수 있으며, 식품, 식품첨가제, 음료, 또는 음료첨가제로 사용되는 경우, 각종 식품류, 육류, 음료수, 초콜렛, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류, 알코올 음료, 비타민 복합제, 주류 및 그 밖의 건강보조식품류일 수 있으나, 이에 한정되는 것은 아니다. 이때, 암 예방 조성물은 최종 제조된 약제, 식품 또는 음료에 0.001 내지 50 중량%으로 포함될 수 있으나, 이에 한정되는 것은 아니다.In addition, the skin inflammation, skin cancer and skin photoaging prevention and treatment agent including as an active ingredient of the present invention can be used as a drug, food, food additives, beverages, beverage additives or cosmetic compositions. The cancer prevention composition may be a cancer prevention agent when used as a medicament, and when used as a food, food additive, beverage, or beverage additive, various foods, meat, beverages, chocolate, snacks, confectionary, pizza, ramen, other noodles, It may be, but is not limited to, gums, ice creams, alcoholic beverages, vitamin complexes, alcoholic beverages, and other health supplements. In this case, the cancer prevention composition may be included in 0.001 to 50% by weight in the final drug, food or beverage, but is not limited thereto.
피부염증, 피부암 및 피부광노화 예방 및 치료제의 제형은 사용방법에 따라 바람직한 형태일 수 있으며, 특히 포유동물에 투여된 후 활성 성분의 신속, 지속 또는 지연된 방출을 제공할 수 있도록 당업계에 공지된 방법을 채택하여 제형화하는 것이 좋다. 구체적인 제형의 예로는 경고제(PLASTERS), 과립제(GRANULES), 로션제(LPTIONS), 리니멘트제(LINIMENTS), 리모나데제(LEMONADES), 방향수제(AROMATIC WATERS), 산제(POWDERS), 시럽제(SYRUPS), 안연고제(OPHTALMIC OINTMENTS), 액제(LIQUIDS AND SOLUTIONS), 에어로솔제(AEROSOLS), 엑스제(EXTRACTS), 엘릭실제(ELIXIRS), 연고제(OINTMENTS), 유동엑스제(FLUIDEXTRACTS), 유제(EMULSIONS), 현탁제(SUSPESIONS), 전제(DECOCTIONS), 침제(INFUSIONS), 점안제(OPHTHALMIC SOLUTIONS), 정제(TABLETS), 좌제(SUPPOSITIORIES), 주사제(INJECTIONS), 주정제(SPIRITS), 카타플라스마제(CATAPLSMA), 캅셀제(CAPSULES), 크림제(CREAMS), 트로키제(TROCHES), 틴크제(TINCTURES), 파스타제(PASTES), 환제(PILLS), 연질 또는 경질 젤라틴 캅셀 등이 있다.Formulations of the prophylactic and therapeutic agents for dermatitis, skin cancer and skin photoaging may be in preferred forms depending on the method of use, in particular methods known in the art to provide rapid, sustained or delayed release of the active ingredient after administration to a mammal. It is good to adopt and formulate. Examples of specific formulations include PLASTERS, GRANULES, LOTION, LPTIONS, LINIMENTS, LIMONADES, AROMATIC WATERS, POWDERS, Syrup ( SYRUPS), OPHTALMIC OINTMENTS, LIQUIDS AND SOLUTIONS, AEROSOLS, EXTRACTS, ELIXIRS, OINTMENTS, FLUIDEXTRACTS, Emulsion ), SUSPENSIONS, DECOCTIONS, INFUSIONS, OPHTHALMIC SOLUTIONS, TABLETS, Suppositories (SUPPOSITIORIES), INJECTIONS, SPIRITS, CATASLSMA ), Capsules (CAPSULES), creams (CREAMS), troches (TROCHES), tinks (TINCTURES), pasta (PASTES), pills (PILLS), soft or hard gelatin capsules.
본 발명에 따른 피부염증, 피부암 및 피부광노화 예방 및 치료제의 투여량은, 투여방법, 복용자의 연령, 성별 및 체중, 및 질환의 중증도 등을 고려하여 결정하는 것이 좋다. 일예로, 본 발명의 피부염증, 피부질환 및 피부 암 예방 및 치료제는 유효성분을 기준으로 하였을 때 1일 0.1 내지 100 ㎎/㎏(체중)으로 1회 이상 투여가능하다. 그러나, 상기한 투여량은 예시하기 위한 일예에 불과하며 상기 범위에 한정되진 않는다.The dosage of the agent for preventing and treating skin inflammation, skin cancer and skin photoaging according to the present invention may be determined in consideration of the method of administration, the age, sex and weight of the recipient, and the severity of the disease. For example, the skin inflammation, skin disease and skin cancer prevention and treatment agent of the present invention can be administered at least once at 0.1 to 100 mg / kg (body weight) per day based on the active ingredient. However, the above dosage is only one example to illustrate and is not limited to the above range.
또한, 본 발명은 상기 화학식 1의 7,3',4'-트리하이드록시아이소플라본은 약제, 식품의 첨가제 또는 화장품 조성물로 사용할 수 있다. In addition, the present invention, 7,3 ', 4'-trihydroxyisoflavone of the formula (1) can be used as a pharmaceutical, food additives or cosmetic composition.
본 발명에 따른 조성물은 약제 조성물, 식품 조성물 또는 화장품 조성물일 수 있으며, 본 발명에서 식품 조성물이라 함은 식품, 식이 보조제, 식품 첨가제, 음료 및 음료첨가제 등을 포함하는 의도이다.The composition according to the present invention may be a pharmaceutical composition, a food composition or a cosmetic composition, the food composition in the present invention is intended to include food, dietary supplements, food additives, beverages and beverage additives and the like.
바람직하게, 본 발명의 조성물은 상기 화학식 1의 7,3',4'-트리하이드록시아이소플라본의 유효성분을 포함하는 약제학적 조성물일 수 있다.Preferably, the composition of the present invention may be a pharmaceutical composition comprising an active ingredient of 7,3 ', 4'-trihydroxyisoflavone of the formula (1).
즉, 본 발명의 방법은, 7,3',4'-트리하이드록시아이소플라본의 COX-2 발현과 종양 형성 및 MMP-1 활성 저해 효과를 이용한 방법으로, 피부염증, 피부암 및 피부 광노화를 예방하고 치료하는데 이용될 수 있다.In other words, the method of the present invention is a method using COX-2 expression, tumor formation and MMP-1 activity inhibition effect of 7,3 ', 4'-trihydroxyisoflavone to prevent dermatitis, skin cancer and skin photoaging And can be used to treat.
상기 약리활성을 갖는 유효성분은 항염증제일 수 있으며, 보다 바람직하게는 피부염증, 피부암 및 피부광노화 예방 및 치료제이다.The active ingredient having the pharmacological activity may be an anti-inflammatory agent, and more preferably, it is an agent for preventing and treating skin inflammation, skin cancer and skin photoaging.
또한, 본 발명에서 7,3',4'-트리하이드록시아이소플라본롤이 식품첨가제로 사용되는 경우 건강증진용 식품 또는 음료 조성물을 제공할 수 있다. 본 발명의 조성물이 식품첨가제로 사용되는 경우, 각종 식품류 예를 들면 육류, 곡류, 카페인 음료, 일반음료, 초콜렛, 빵류, 스넥류, 과자류, 피자, 라면, 기타 면류, 껌류, 아이스크림류, 알코올성 음료, 술, 비타민 복합제 및 그밖의 건강보조식품류 등에 사용될 수 있으나, 이에 한정되는 것은 아니다.In addition, the present invention may provide a food or beverage composition for health promotion when 7,3 ', 4'-trihydroxyisoflavonol is used as a food additive. When the composition of the present invention is used as a food additive, various foods such as meat, cereals, caffeine drinks, general beverages, chocolate, breads, snacks, confectionery, pizza, ramen, other noodles, gums, ice creams, alcoholic beverages, Alcohol, vitamin complexes and other health supplements can be used, but is not limited thereto.
본 발명의 7,3',4'-트리하이드록시아이소플라본은 조리된 식품에 일정량을 첨가하여 건강 증진용 식품 또는 음료를 제조할 수 있으며, 이 경우 최종적으로 제 조된 식품 또는 음료 중에 7,3',4'-트리하이드록시아이소플라본의 함량은 0.01 내지 50 중량% 범위로 포함될 수 있다. 이때, 7,3',4'-트리하이드록시아이소플라본의 함량이 0.01 중량% 미만이면 효과가 미비할 수 있고, 50 중량%를 초과하는 경우 사용량 대비 효과 증가가 미비하여 비경제적이다.7,3 ', 4'-trihydroxyisoflavones of the present invention can be added to the cooked food to a certain amount to prepare a health-promoting food or drink, in this case 7,3 in the finally produced food or drink The content of ', 4'-trihydroxyisoflavones may be included in the range of 0.01 to 50% by weight. In this case, when the content of 7,3 ', 4'-trihydroxyisoflavone is less than 0.01% by weight, the effect may be insignificant, and when the content exceeds 50% by weight, the increase in effect relative to the amount of use is inadequate.
본 발명의 화합물이 화장료 조성물로 사용되는 경우에 전체 중량부에 대해, 7,3',4'-트리하이드록시아이소플라본의 함량은 총중량에 대해 0.01 중량% 내지 50 중량%, 바람직하게는 0.01 중량% 내지 11 중량%를 바람직하게 나타낸다. 만약 7,3',4'-트리하이드록시아이소플라본이 식물 추출물을 함유하는 용액의 형태로 존재한다면, 당업자는 상기 농도 범위의 이소플라보노이드를 수득하기 위해 본 발명에 따른 조성물 내에 이 용액의 양을 조절할 수 있을 것이다.When the compound of the present invention is used as a cosmetic composition, the content of 7,3 ', 4'-trihydroxyisoflavone is 0.01 to 50% by weight, preferably 0.01% by weight, based on the total weight. % To 11% by weight are preferred. If 7,3 ', 4'-trihydroxyisoflavones are present in the form of a solution containing a plant extract, one skilled in the art can determine the amount of this solution in the composition according to the invention to obtain isoflavonoids in the above concentration range. It will be adjustable.
본 발명의 화장료 조성물은 국소적 적용을 위해 보통 사용되는 임의의 약제학적 형태, 특히 수성, 수성-알콜성 또는 오일성 용액,수중유 또는 유중수 또는 다중 에멀젼, 수성 또는 오일성 겔, 액체, 페이스트성 또는 고체 무수 생성물, 소구체를 사용한 수성 상에의 오일 분산물 (이들 소구체는 나노구체 및 나노캡슐과 같은 중합체 나노입자일 수 있다) 의 형태일 수 있으며, 또는 보다 좋게는 이온성 및/또는 비이온성 형태의 지질 소포체의 형태일 수 있다.The cosmetic compositions of the present invention may be in any pharmaceutical form commonly used for topical application, especially aqueous, aqueous-alcoholic or oily solutions, oil-in-water or water-in-oil or multiple emulsions, aqueous or oily gels, liquids, pastes or Solid anhydrous product, may be in the form of an oil dispersion in an aqueous phase using globules, these globules may be polymer nanoparticles such as nanospheres and nanocapsules, or more preferably ionic and / or It may be in the form of a lipophilic endoplasmic reticulum.
본 발명의 조성물은 다소 유체일 수 있으며, 백색 또는 유색 크림, 연고, 밀크, 로션, 유액 (serum), 페이스트 또는 무스의 외관을 가질 수 있다. 이는 선택적으로 에어로졸 형태로 피부에 적용될 수도 있다. 이는 또한 고체 형태 예컨대, 스틱의 형태일 수 도 있다. 이는 피부용 케어 제품 및/또는 메이크업 제품으로서 사 용될 수도 있다.The compositions of the present invention may be somewhat fluid and may have the appearance of white or colored creams, ointments, milks, lotions, serums, pastes or mousses. It may optionally be applied to the skin in the form of an aerosol. It may also be in solid form, for example in the form of a stick. It may be used as a skin care product and / or makeup product.
공지된 방식으로, 본 발명에 따른 조성물은 또한 화장 분야에서 통상적인 보조제, 예컨대 친수성 또는 친지성 겔화제, 친수성 또는 친지성 활성제, 보존제, 항산화제, 용매, 방향제, 충전제, 차단제, 안료, 흡취제 및 염료를 함유할 수 있다. 이들 다양한 보조제의 양은 당해 분야에서 통상적으로 사용되는 양이며, 예컨대 조성물 총중량에 대해 0.01 중량% 내지 20 중량%이다. 그 성질에 따라, 이 보조제는 지방 상, 수성 상, 지질 소포체 및/또는 나노입자에 도입될 수 있다. 어떠한 경우에 라도, 보조제 및 그 비율은 본 발명에 따른 조성물의 바람직한 성질에 악영향을 미치지 않도록 선택될 것이다.In a known manner, the compositions according to the invention can also be used in conventional cosmetics such as auxiliaries such as hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic active agents, preservatives, antioxidants, solvents, fragrances, fillers, blockers, pigments, odorants. And dyes. The amounts of these various adjuvants are amounts commonly used in the art, such as from 0.01% to 20% by weight relative to the total weight of the composition. Depending on its nature, this adjuvant can be incorporated into the fatty phase, aqueous phase, lipid vesicles and / or nanoparticles. In any case, the adjuvant and its proportions will be chosen so as not to adversely affect the desirable properties of the composition according to the invention.
본 발명에 따른 조성물이 에멀젼인 경우, 지방 상의 비율은 조성물 총중량에 대해 5% 내지 80%, 바람직하게는 5% 내지 50% 범위일 수 있다. 에멀젼 형태의 조성물에서 사용되는 오일, 유화제 및 공유화제 (coemulsifier) 는 당해 분야에서 통When the composition according to the invention is an emulsion, the proportion of fat phase can range from 5% to 80%, preferably 5% to 50% by weight of the composition. Oils, emulsifiers and coemulsifiers used in compositions in emulsion form are known in the art.
상적으로 사용되는 것들 중에서 선택된다. 유화제 및 공유화제는 조성물 총중량에 대해 0.3% 내지 30%, 바람직하게는 0.5% 내지 20% 의 비율로 조성물 내에 존재한다.It is selected from those used commercially. Emulsifiers and covalent agents are present in the composition at a rate of 0.3% to 30%, preferably 0.5% to 20%, relative to the total weight of the composition.
본 발명에서 사용될 수 있는 오일로서, 미네랄 오일 (액체 석유 젤리) 및 그 에스테르, 식물 기원의 오일 (아보카도 오일,대두유), 동물 기원의 오일 (라놀린), 합성 오일 (퍼히드로스쿠알렌), 실리콘 오일 (시클로메티콘) 및 플로오로 오일 (퍼플루오로폴리에테르)를 언급할 수 있다. 지방성 알콜 (세틸 알콜), 지방산 및 왁스 (카르나우바 왁스, 오조케라이트) 또한 지방성 물질로서 사용될 수 있다.As oils that can be used in the present invention, mineral oils (liquid petroleum jelly) and esters thereof, oils of vegetable origin (avocado oil, soybean oil), oils of animal origin (lanolin), synthetic oils (perhydrosqualene), silicone oils ( Cyclomethicone) and fluoro oils (perfluoropolyethers) may be mentioned. Fatty alcohols (cetyl alcohol), fatty acids and waxes (carnauba wax, ozokerite) can also be used as fatty substances.
본 발명에서 사용될 수 있는 유화제 및 공유화제로서, 예컨대 PEG-20 스테아레이트와 같은 폴리에틸렌 글리콜의 지방산에스테르, 및 글리세릴 스테아레이트와 같은 글리세롤의 지방산 에스테르를 언급할 수 있다.As emulsifiers and covalent agents that can be used in the present invention, mention may be made of fatty acid esters of polyethylene glycol such as PEG-20 stearate, and fatty acid esters of glycerol such as glyceryl stearate.
친수성 겔화제로서 특히 카르복시비닐 중합체 (카르보머), 아크릴레이트/알킬아크릴레이트 공중합체와 같은 아크릴 공중합체, 폴리아크릴아미드, 폴리사카라이드, 천연 검 및 점토를 언급할 수 있고, 친지성 겔화제로서 벤톤과 같은 변성 점As the hydrophilic gelling agent, mention may be made in particular of carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkylacrylate copolymers, polyacrylamides, polysaccharides, natural gums and clays, and as lipophilic gelling agents Denaturation point such as benton
토, 지방산의 금속 염, 소수성 실리카 및 폴리에틸렌을 언급할 수 있다.Mention may be made of earth salts, metal salts of fatty acids, hydrophobic silica and polyethylene.
활성제로서, 본 조성물은 하나 이상의 자외선 차단제 및/또는 각질용해제 및/또는 피부 박리제를 함유하는 것이 바람직하다.As the active agent, the composition preferably contains one or more sunscreens and / or keratinants and / or skin exfoliants.
본 발명에 따른 7,3',4'-트리하이드록시아이소플라본은 자외선 조사에 의해 증가된 COX-2 발현 저해 효과, 2단계 마우스 발암 모델에서 종양 형성 억제 효과 및 자외선 조사에 의해 증가된 MMP-1 활성 억제 효과를 갖는다. 따라서 7,3',4'-트리하이드록시아이소플라본을 첨가한 조성물은 우수한 피부염증, 피부암 및 피부광노화 예방 및 치료제이다.7,3 ', 4'-trihydroxyisoflavones according to the present invention has the effect of inhibiting COX-2 expression increased by UV irradiation, tumor suppression effect in two-stage mouse carcinogenesis model, and MMP- increased by UV irradiation. 1 Has an activity inhibitory effect. Thus, the composition to which 7,3 ', 4'-trihydroxyisoflavones are added is an excellent skin inflammation, skin cancer and skin photoaging prevention and treatment.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 단, 이들 실시예들은 본 발명을 보다 쉽게 이해하기 위하여 예시하는 것일 뿐, 본 발명이 이들만으로 한정되는 것은 아니다.Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, these examples are only to illustrate the present invention more easily, the present invention is not limited to these.
실시예 1: 7,3',4'-트리하이드록시아이소플라본의 COX-2 발현 저해 효과 측정Example 1: Determination of the COX-2 Expression Inhibition Effect of 7,3 ', 4'-trihydroxyisoflavone
쥐 피부상피세포인 JB 6 P+ 세포(입수처: 미국세포주은행(ATCC)를 5 % 우태아 혈청(fetal bovine serum; FBS)에 페니실린 7.5 mg/L, 스트렙토마이신 7.5 mg/L를 함유하고 MEM 배지를 사용하여 5 % CO2, 37℃ 배양기(Forma Scientific Co., Marjetta, OH, USA)에서 배양하였다. 배지 조성물들은 모두 GIBCO BRL(Grand Island, NY, USA)사 제품을 사용하였다. Rat skin epithelial cells JB 6 P + cells (obtained from the American Cell Line Bank (ATCC)) contained 7.5 mg / L of penicillin and 7.5 mg / L of streptomycin in 5% fetal bovine serum (FBS) and MEM medium. Incubated in a 5
7,3',4'-트리하이드록시아이소플라본이 UVB에 의한 COX-2의 발현을 저해하는지 측정하기 위해에 의해 웨스턴 블랏팅 분석법(western blotting analysis)[Upham, B. L., Kang, K. S., Cho, H. Y., & Trosko, J. E. Carcinogenesis 18:37-42, 1997]을 이용하여 분석하였다.Western blotting analysis by Upham, BL, Kang, KS, Cho, to determine whether 7,3 ', 4'-trihydroxyisoflavones inhibit the expression of COX-2 by UVB. HY, & Trosko, JE Carcinogenesis 18: 37-42, 1997].
7,3',4'-트리하이드록시아이소플라본을 농도별로 1 시간 전처리 후, UVB 4 kJ/m2를 조사한 후 4시간 동안 배양하였다. 배양된 세포로부터 단백질을 추출하기 위하여 1 mM 페닐메틸설포닐프루오라이드(Phenylmethylsulfonylfluoride, PMSF)을 포함하는 20% SDS로 추출하였다. 단백질 함량은 DC assay kit[Bio-Rad Corp., Richmond, CA, USA]를 이용하여 결정하였다. 각각의 단백질 추출물들로부터 약 15 ㎍에 해당하는 단백질을 10% SDS-PAGE에 넣어 전기영동하여 분리하였다. COX-2 폴리클론 항체[Cayman Chemical, Ann Arbor, MI, USA]를 이용하여 반응시킨 후, ECL 키트[Amersham, Life Science, Denver, USA]를 이용하여 감지하였다.After 7,3 ', 4'-trihydroxyisoflavones were pretreated for 1 hour by concentration,
도 1a는 7,3',4'-트리하이드록시아이소플라본의 COX-2의 억제 효과를 나타낸 것으로, 레인 1은 무처리 대조군이고 레인2는 UVB 조사군, 레인 3은 UVB와 7,3',4'-트리하이드록시아이소플라본 20 μM 처리군, 레인 4는 UVB와 7,3',4'-트리하이드록시아이소플라본 40 μM 처리군, 레인 5는 UVB와 7,3',4'-트리하이드록시아이소플라본 60 μM 처리군 이다. COX-2의 밴드가 농도 의존적으로 감소함을 확인하였다. 베타액틴은 동일한 양의 세포로 실험했음을 증명한다. Figure 1a shows the inhibitory effect of COX-2 of 7,3 ', 4'-trihydroxyisoflavones,
도 1b는 다이드제인은 COX-2의 발현 억제 효능이 없음을 나타낸 것으로, 레인 1은 무처리 대조군이고 레인2는 UVB 조사군, 레인 3은 UVB와 다이드제인 20 μM 처리군, 레인 4는 UVB와 다이드제인 40 μM 처리군, 레인 5는 UVB와 다이드제인 60 μM 처리군 이다. COX-2의 밴드가 다이드제인 처리에 따라 변화가 없었다. 베타액틴은 동일한 양의 세포로 실험했음을 증명한다. Figure 1b shows that Dyze-Zone is not effective in inhibiting the expression of COX-2,
따라서 7,3',4'-트리하이드록시아이소플라본는 자외선에 의해 증가된 COX-2의 발현을 농도 의존적으로 감소시키는것에 반해 다이드제인은 자외선에 의해 증가된 COX-2 발현에 영향을 끼치지 않았다.Thus, while 7,3 ', 4'-trihydroxyisoflavones reduce the concentration-dependent expression of increased COX-2 by UV light, Dyzedine does not affect the increased COX-2 expression by UV light. Did.
실시예 2: 7,3',4'-트리하이드록시아이소플라본의 COX-2 프로모터 활성 저해효과Example 2: Inhibitory Effect of 7,3 ', 4'-trihydroxyisoflavones on COX-2 Promoter Activity
JB 6 P+세포에 COX-2 루시퍼레이즈 플라스미드(luciferase reporter plasmid)를 안정적으로 도입시켜 COX-2 프로모터 활성여부를 측정하였다. 7,3',4'-트리하이드록시아이소플라본을 농도별로 1 시간 전처리 후, UVB 4 kJ/m2를 조사한 후 24 시간 동안 배양한 후 Luciferase 용액을 넣어서 루미노미터로 측정하였다. 도 2a에서 보이는 것과 같이 7,3',4'-트리하이드록시아이소플라본이 UVB로 유도한 COX-2 프로모터의 활성을 저해한 다는 것을 알 수 있다. 따라서 7,3',4'-트리하이드록시아이소플라본은 자외선에 의해 증가된 COX-2 프로모터의 활성을 농도 의존적으로 감소시킴을 알 수 있다. 그러나 도 2b에서 보이는 것과 같이 다이드제인 처리시에는 COX-2 프로모터의 활성을 감소시키지 못함을 할 수 있다. 따라서 7,3',4'-트리하이드록시아이소플라본은 COX-2 발현을 전사인자 수준에서 억제함을 알 수 있다. The COX-2 promoter activity was measured by stably introducing the COX-2 luciferase reporter plasmid into JB 6 P + cells. After pretreatment with 7,3 ', 4'-trihydroxyisoflavones by concentration for 1 hour,
실시예 3: 7,3',4'-트리하이드록시아이소플라본의 염증유발 전사인자 NF-kB 활성 저해효과Example 3: Inhibitory Effect of 7,3 ', 4'-Trihydroxy Isoflavone Induced Transcription Factor NF-kB Activity
JB 6 P+세포에 염증유발 전사인자인 NF-κB 루시퍼레이즈 플라스미드(luciferase reporter plasmid)를 안정적으로 도입시켜 활성여부를 측정하였다. 7,3',4'-트리하이드록시아이소플라본을 농도별로 1 시간 전처리 후, UVB 4 kJ/m2를 조사한 후 24 시간 동안 배양한 후 Luciferase 용액을 넣어서 루미노미터로 측정하였다. 도 3a에서 보이는 것과 같이 7,3',4'-트리하이드록시아이소플라본이 UVB로 유도한 NF-κB 전사인자의 활성을 저해한 다는 것을 알 수 있다. 따라서 7,3',4'-트리하이드록시아이소플라본은 자외선에 의해 증가된 NF-κB 전사인자의 활성을 농도 의존적으로 감소시킴을 알 수 있다. 그러나 도 3b에서 보이는 것과 같이 다이드제인은 7,3',4'-트리하이드록시아이소플라본에 비해 NF-κB 전사인자의 활성을 감소시키는 능력이 적음을 알 수 있다. 따라서 7,3',4'-트리하이드록시아이소플라본이 UVB로 유도된 COX-2 발현을 억제하는 것은 COX-2 와 NF-κB 의 전사인자 활성을 저해하기 때문임을 알 수 있다. NF-κB luciferase reporter plasmid, which is an inflammation-induced transcription factor, was stably introduced into JB 6 P + cells to measure activity. After pretreatment with 7,3 ', 4'-trihydroxyisoflavones by concentration for 1 hour,
실시예 4: 7,3',4'-트리하이드록시아이소플라본의 p38, JNK(Jun N-terminal kinase) 인산화 저해 효과 측정Example 4: Determination of p38, JNK (Jun N-terminal kinase) phosphorylation inhibitory effect of 7,3 ', 4'-trihydroxyisoflavone
7,3',4'-트리하이드록시아이소플라본이 자외선에 의해 COX-2 발현이 증가될 때 발생하는 주요한 현상인 p38, JNK 의 인산화를 저해하는지를 측정하기 위하여, 웨스턴 블랏팅 분석법을 이용하였으며, 7,3',4'-트리하이드록시아이소플라본을 농도별로 1 시간 전처리 후, UVB 4 kJ/m2를 조사한 후 30분 동안 배양한 후 단백질을 추출하였다. p38, JNK 의 인산화와 비인산화의 선택적인 항체[Upstate Biotechnology, Inc.,Lake Placid, NY]를 이용하여 반응시켰다. Western blotting was used to determine whether 7,3 ', 4'-trihydroxyisoflavones inhibit the phosphorylation of p38, JNK, a major phenomenon that occurs when COX-2 expression is increased by UV light. After pretreatment with 7,3 ', 4'-trihydroxyisoflavones by concentration for 1 hour,
도 4는 7,3',4'-트리하이드록시아이소플라본의 인산화 저해 효과를 나타낸 것으로, 레인 1은 무처리 대조군이고 레인2는 UVB 조사군, 레인 3은 레인 3은 UVB와 7,3',4'-트리하이드록시아이소플라본 20 μM 처리군, 레인 4는 UVB와 7,3',4'-트리하이드록시아이소플라본 40 μM 처리군, 레인 5는 UVB와 7,3',4'-트리하이드록시아이소플라본 60 μM 처리군 이다. UVB에 의해 인산화된 형태인 p-p38, p-JNK 의 밴드가 농도 의존적으로 감소함을 확인하였다. 인산화 되지 않은 p38, JNK 은 동일한 양의 세포로 실험했음을 증명한다. 따라서 7,3',4'-트리하이드록시아이소플라본은 자외선에 의해 인산화된 p38, JNK 의 발현을 농도 의존적으로 감소시킴을 알 수 있다.Figure 4 shows the phosphorylation inhibitory effect of 7,3 ', 4'-trihydroxyisoflavones,
실시예 5: 7,3',4'-트리하이드록시아이소플라본의 2단계 마우스 발암모델에서 만성 적인 UVB 의 처리에 의해 증가된 종양 형성 억제 및 항 염증 효과Example 5: Antitumor and Tumor Formation Increased by Chronic UVB Treatment in a Two-Stage Mouse Carcinogenic Model of 7,3 ', 4'-trihydroxyisoflavone
Female SKH-1 hairless 마우스의 등에 7,3',4'-트리하이드록시아이소플라본을 농도별로 1시간 전처리후, UVB를 0.18 J/cm2으로 조사하는 과정을 27 주간 일주일에 세 번씩 진행하였다. 종양의 발생을 일주일 마다 기록하였고 2주 이상 지속되고 직경이 1mm 이상인 경우에 종양으로 분류하였다. 도 5a 는 27 주 후 종양이 발생하고 7,3',4'-트리하이드록시아이소플라본의 종양 억제 효과를 보이고 있는 사진 결과이다. 도 5b 는 종양 개 수를 정량화 한 것으로 UVB 단독 처리 군의 종양 개수에 비해서 7,3',4'-트리하이드록시아이소플라본 10 nmol, 40 nmmol 처리시 종양의 발생이 억제 됨을 알 수 있었다. 도 5c 는 27 주 후 마우스의 등 피부를 적출하여 지방을 제거 후, 단백질을 추출하여 상기의 COX-2 폴리클론 항체를 이용하여 웨스턴 블랏팅 분석법을 통해 COX-2 발현을 확인한 결과이다. 레인 1~5은 무처리 대조군이고 레인6~10는 UVB 조사군, 레인 11~15은 UVB와 7,3',4'-트리하이드록시아이소플라본 10 nmol 처리군, 레인 16~20는 UVB와 7,3',4'-트리하이드록시아이소플라본 40 nmol 처리군 이다. 만성적인 UVB 조사에 의해 종양이 형성됨과 동시에 대표적 염증 지표인 COX-2 발현이 증가하였고, 이를 7,3',4'-트리하이드록시아이소플라본이 농도 의존적으로 감소 시켰다. 베타액틴은 동일한 양의 세포로 실험했음을 증명한다. 따라서 7,3',4'-트리하이드록시아이소플라본은 마우스 in vivo 실험을 통해서 만성적인 UVB 조사에 의한 피부 암 억제 효과와 자외선에 의해 증가한 염증 지표인 COX-2의 발현을 농도 의존적으로 저해함을 확인하였다.After 1 hour pretreatment with 7,3 ', 4'-trihydroxyisoflavones by concentration for 1 hour in female SKH-1 hairless mice, UVB was irradiated at 0.18 J / cm2 three times a week for 27 weeks. The incidence of tumors was recorded weekly and classified as tumors that lasted more than two weeks and were 1 mm or more in diameter. FIG. 5A is a photographic result of tumor development after 27 weeks and showing tumor suppression effect of 7,3 ′, 4′-trihydroxyisoflavone. FIG. Figure 5b is a quantification of the number of tumors compared to the number of tumors in the UVB treatment group, it can be seen that the occurrence of the tumor is suppressed when treatment with 7,3 ', 4'-trihydroxyisoflavone 10 nmol, 40 nmmol. FIG. 5C shows the results of confirming COX-2 expression through Western blotting analysis using the COX-2 polyclonal antibody after extracting protein after removing fat from the back skin of the mouse after 27 weeks. Lanes 1-5 are untreated controls, lanes 6-10 are UVB irradiated groups, lanes 11-15 are UVB and 7,3 ', 4'-trihydroxyisoflavones 10 nmol treated groups, and lanes 16-20 are UVB and 7,3 ', 4'-trihydroxyisoflavone 40 nmol treatment group. As the tumor was formed by chronic UVB irradiation, the expression of COX-2, a representative inflammatory marker, was increased, and the concentration of 7,3 ', 4'-trihydroxyisoflavone decreased. Beta-actin proves that experiments with the same amount of cells. Therefore, 7,3 ', 4'-trihydroxyisoflavone inhibits the skin cancer effect by chronic UVB irradiation and the expression of COX-2, which is an indicator of inflammation increased by UV rays, through mouse in vivo experiment. It was confirmed.
실시예 6: 7,3',4'-트리하이드록시아이소플라본의 MMP-1 활성 저해 효과 측정Example 6: Determination of the inhibitory effect of MMP-1 activity of 7,3 ', 4'-trihydroxyisoflavone
인간 피부 표피세포 (human keratinocyte cells) 인 HaCa T 세포를 10 % 우태아 혈청(fetal bovine serum; FBS)에 페니실린 7.5 mg/L, 스트렙토마이신 7.5 mg/L를 함유하고 DMEM 배지를 사용하여 5 % CO2, 37℃ 배양기(Forma Scientific Co., Marjetta, OH, USA)에서 배양하였다. 배지 조성물들은 모두 GIBCO BRL(Grand Island, NY, USA)사 제품을 사용하였다. HaCa T cells, human keratinocyte cells, contain 7.5 mg / L of penicillin and 7.5 mg / L of streptomycin in 10% fetal bovine serum (FBS) and 5% CO2 using DMEM medium. Incubated in a 37 ° C. incubator (Forma Scientific Co., Marjetta, OH, USA). Media compositions were all used by GIBCO BRL (Grand Island, NY, USA).
7,3',4'-트리하이드록시아이소플라본이 UVB에 의한 MMP-1의 발현을 저해하는지 측정하기 위해에 의해 웨스턴 블랏팅 분석법(western blotting analysis)[Upham, B. L., Kang, K. S., Cho, H. Y., & Trosko, J. E. Carcinogenesis 18:37-42, 1997]을 이용하여 분석하였다.Western blotting analysis by Upham, BL, Kang, KS, Cho, to determine whether 7,3 ', 4'-trihydroxyisoflavones inhibit the expression of MMP-1 by UVB. HY, & Trosko, JE Carcinogenesis 18: 37-42, 1997].
7,3',4'-트리하이드록시아이소플라본을 농도별로 1 시간 전처리 후, UVB 0.01 J/cm2를 조사한 후 48 시간 동안 배양하였다. MMP-1 은 세포 밖으로 분비되는 효소로써 이를 모으기 위해 배양된 세포의 배지를 회수 하였다. 단백질 함량은 DC assay kit [Bio-Rad Corp., Richmond, CA, USA]를 이용하여 결정하였다. 각각의 단백질 추출물들로부터 약 30 ㎍에 해당하는 단백질을 10% SDS-PAGE에 넣어 전기영동하여 분리하였다. MMP-1 모노클론 항체 [Epitomics, CA, USA]를 이용하여 반응시킨 후, ECL 키트[Amersham, Life Science, Denver, USA]를 이용하여 감지하였다.7,3 ', 4'-trihydroxyisoflavones were pretreated for 1 hour by concentration, and then incubated for 48 hours after irradiation with UVB 0.01 J / cm 2 . MMP-1 is an enzyme secreted out of the cells to recover the culture of the cultured cells to collect them. Protein content was determined using a DC assay kit [Bio-Rad Corp., Richmond, CA, USA]. About 30 μg of protein from each protein extract was separated by electrophoresis into 10% SDS-PAGE. After the reaction using the MMP-1 monoclonal antibody [Epitomics, CA, USA], it was detected using the ECL kit [Amersham, Life Science, Denver, USA].
도 6a는 7,3',4'-트리하이드록시아이소플라본의 MMP-1 활성 억제 효과를 나타낸 것으로, 레인 1은 무처리 대조군이고 레인2는 UVB 조사군, 레인 3은 UVB와 7,3',4'-트리하이드록시아이소플라본 20 μM 처리군, 레인 4는 UVB와 7,3',4'-트 리하이드록시아이소플라본 40 μM 처리군 이다. MMP-1의 밴드가 농도 의존적으로 감소함을 확인하였다. Figure 6a shows the effect of inhibiting the MMP-1 activity of 7,3 ', 4'-trihydroxyisoflavones,
도 6b 는 도 6a 의 결과에서 MMP-1 활성을 정량한 그래프 이다. 7,3',4'-트리하이드록시아이소플라본은 자외선에 의해 증가된 MMP-1 활성을 농도의존적으로 감소시킴을 알 수 있다. Figure 6b is a graph quantifying the MMP-1 activity in the results of Figure 6a. It can be seen that 7,3 ', 4'-trihydroxyisoflavone reduces concentration-dependently increased MMP-1 activity by ultraviolet light.
실시예 7: 인간 피부 표피 세포에서 7,3',4'-트리하이드록시아이소플라본의 MMP-1 조절 전사인자인 AP-1 활성 저해효과Example 7 Inhibitory Effect of 7,3 ', 4'-trihydroxyisoflavone on AP-1 Activity, an MMP-1 Regulatory Transcription Factor in Human Skin Epidermal Cells
인간 피부 표피세포 (human keratinocyte cells) 인 HaCa T 세포에 MMP-1 조절 전사인자인 AP-1 루시퍼레이즈 플라스미드(luciferase reporter plasmid)를 안정적으로 도입시켜 활성여부를 측정하였다. 7,3',4'-트리하이드록시아이소플라본을 농도별로 1 시간 전처리 후, UVB 0.01 J/cm2를 조사한 후 5 시간 동안 배양한 후 Luciferase 용액을 넣어서 루미노미터로 측정하였다. 도 7에서 보이는 것과 같이 7,3',4'-트리하이드록시아이소플라본이 UVB로 유도한 AP-1 전사인자의 활성을 저해한 다는 것을 알 수 있다. 따라서 7,3',4'-트리하이드록시아이소플라본은 자외선에 의해 증가된 AP-1 전사인자의 활성을 농도 의존적으로 감소시킴을 알 수 있다. 따라서 7,3',4'-트리하이드록시아이소플라본이 UVB로 유도된 MMP-1 활성을 억제하는 것은 AP-1 의 전사인자 활성을 저해하기 때문임을 알 수 있다. MMP-1 regulatory transcription factor AP-1 luciferase reporter plasmid was stably introduced into HaCa T cells, which are human keratinocyte cells, to determine their activity. After pretreatment with 7,3 ', 4'-trihydroxyisoflavones by concentration for 1 hour, UVB 0.01 J / cm 2 was irradiated for 5 hours and then Luciferase solution was added to measure the luminometer. As shown in FIG. 7, it can be seen that 7,3 ', 4'-trihydroxyisoflavone inhibits the activity of UV-1 induced AP-1 transcription factor. Therefore, it can be seen that 7,3 ', 4'-trihydroxyisoflavone reduces concentration-dependently the activity of AP-1 transcription factor increased by ultraviolet rays. Therefore, it can be seen that 7,3 ', 4'-trihydroxyisoflavone inhibits UVB-induced MMP-1 activity because it inhibits the transcription factor activity of AP-1.
실시예 8: 항암제 제조Example 8: Anticancer Agent Preparation
8-1. 산제8-1. Powder
7,3',4'-트리하이드록시아이소플라본 2 g에 유당 1 g을 혼합하고, 기밀포에 충진하여 산제를 제조하였다.1 g of lactose was mixed with 2 g of 7,3 ', 4'-trihydroxyisoflavones and filled into an airtight cloth to prepare a powder.
8-2. 정제8-2. refine
7,3',4'-트리하이드록시아이소플라본 100 ㎎, 옥수수전분 100 ㎎, 유당 100 ㎎ 및 스테아린산 마그네슘 2 ㎎을 혼합한 후 통상의 정제 제조방법에 따라 타정하여 정제를 제조하였다.Tablets were prepared by mixing 100 mg of 7,3 ', 4'-trihydroxyisoflavones, 100 mg of corn starch, 100 mg of lactose and 2 mg of magnesium stearate, followed by compression according to a conventional tablet preparation method.
8-3. 캡슐제8-3. Capsule
7,3',4'-트리하이드록시아이소플라본 100 ㎎, 옥수수전분 100 ㎎, 유당 100 ㎎ 및 스테아린산 마그네슘 2 ㎎을 혼합한 후 젤라틴 캡슐에 충전하여 캡슐제를 제조하였다.A capsule was prepared by mixing 100 mg of 7,3 ', 4'-trihydroxyisoflavone, 100 mg of corn starch, 100 mg of lactose and 2 mg of magnesium stearate, and then filling the gelatine capsule.
8-4. 주사제8-4. Injection
7,3',4'-트리하이드록시아이소플라본 100 ㎎에 주사용 증류수 적량을 가하여 용해시키고, pH를 약 7.5로 조절한 다음 2 ㎖ 용량의 앰플에 충진 및 멸균시하여 주사제를 제조하였다.An injection was prepared by adding a suitable amount of distilled water for injection to 100 mg of 7,3 ', 4'-trihydroxyisoflavone, adjusting the pH to about 7.5, and then filling and sterilizing a 2 ml ampoule.
실시예 9: 기능성 식품 제조Example 9: Functional Food Preparation
9-1. 선식9-1. Wire
현미, 보리, 찹쌀, 율무를 공지의 방법으로 알파화시켜 건조시킨 것을 배전한 후 분쇄기로 입도 60메쉬의 분말로 준비하였다. 검정콩, 검정깨 및 들깨 각각을 공지의 방법으로 쪄서 건조시킨 후 배전 및 분쇄하여 입도 60 메쉬의 분말로 준비하였다.Brown rice, barley, glutinous rice, and yulmu were alphad by a known method, and then dried and roasted. Black beans, black sesame seeds and perilla were each steamed and dried in a known manner, then roasted and ground to prepare a powder having a particle size of 60 mesh.
이후, 현미 30 중량%, 율무 15 중량%, 보리 20 중량%, 찹쌀 9 중량%, 들깨 7 중량%, 검정콩 8 중량%, 검정깨 7 중량%, 7,3',4'-트리하이드록시아이소플라본 3 중량%, 영지 0.5 중량% 및 지황 0.5중량%을 혼합하여 선식을 제조하엿다.Then, 30% by weight brown rice, 15% by weight barley, 20% by weight barley, 9% by weight glutinous rice, 7% by weight perilla, 8% by weight black soybean, 7% by weight black sesame, 7,3 ', 4'-trihydroxyiso A wire was prepared by mixing 3% by weight of flavone, 0.5% by weight of ganoderma lucidum and 0.5% by weight of turmeric.
9-2. 츄잉껌9-2. Chewing gum
껌 베이스 20 중량%, 설탕 76.9 중량%, 향료 1 중량%, 물 2 중량% 및 7,3',4'-트리하이드록시아이소플라본 0.1 중량%를 배합하여 통상의 방법으로 츄잉껌을 제조하였다.Chewing gum was prepared in a conventional manner by combining 20% by weight of gum base, 76.9% by weight of sugar, 1% by weight of perfume, 2% by weight of water, and 0.1% by weight of 7,3 ', 4'-trihydroxyisoflavone.
9-3. 캔디9-3. candy
설탕 60 중량%, 물엿 39.8 중량%, 향료 0.1 중량% 및 7,3',4'-트리하이드록시아이소플라본 0.1 중량%를 배합하여 통상의 방법으로 캔디를 제조하였다.Candy was prepared in a conventional manner by combining 60% by weight of sugar, 39.8% by weight of starch syrup, 0.1% by weight of perfume, and 0.1% by weight of 7,3 ', 4'-trihydroxyisoflavone.
9-4. 비스켓9-4. Biscuits
박력 1급 25.59 중량%, 중력 1급 22.22 중량%, 정백당 4.80 중량%, 식염 0.73 중량%, 포도당 0.78 중량%, 팜쇼트닝 11.78 중량%, 암모니움 1.54 중량%, 중조 0.17 중량%, 중아황산나트륨 0.16 중량%, 쌀가루 1.45 중량%, 비타민 B₁0.0001 중량%, 비타민 B₂0.0001 중량%, 밀크향 0.04 중량%, 물 20.6998 중량%, 전지분유 1.16 중량%, 대용분유 0.29 중량%, 제일인산칼슘 0.03 중량%, 살포염 0.29 중량% 및 분무유 7.27 중량%와 7,3',4'-트리하이드록시아이소플라본 1 중량%를 배합하여 통상의 방법으로 비스켓을 제조하였다. Force 1st class 25.59 wt%, 1st class gravity 22.22 wt%, white sugar 4.80 wt%, salt 0.73 wt%, glucose 0.78 wt%, palm shortening 11.78 wt%, ammonium 1.54 wt%, sodium bicarbonate 0.17 wt%, sodium bisulfite 0.16 wt %, Rice flour 1.45 wt%, Vitamin B₁0.0001 wt%, Vitamin B20.0001 wt%, Milk flavor 0.04 wt%, Water 20.6998 wt%, Whole milk powder 1.16 wt%, Substitute milk powder 0.29 wt%, Calcium phosphate 0.03 wt% , Biscuits were prepared in a conventional manner by combining 0.29 wt% of spraying salt, 7.27 wt% of spray oil, and 1 wt% of 7,3 ′, 4′-trihydroxyisoflavone.
9-5. 건강음료9-5. Health drink
꿀 0.26 중량%, 치옥토산아미드 0.0002 중량%, 니코틴산아미드 0.0004 중량 %, 염산리보플라빈나트륨 0.0001 중량%, 염산피리독신 0.0001 중량%, 이노시톨 0.001 중량%, 오르트산 0.002 중량%, 물 98.7362 중량% 및 7,3',4'-트리하이드록시아이소플라본 1 중량%를 배합하여 통상의 방법으로 건강 음료를 제조하였다.0.26% by weight of honey, 0.0002% by weight of thioctoamide, 0.0004% by weight of nicotinic acid, 0.0001% by weight of riboflavin sodium hydrochloride, 0.0001% by weight of pyridoxine hydrochloride, 0.001% by weight of inositol, 0.002% by weight of orthoic acid, 98.7362% by weight of water, and 7, 1% by weight of 3 ', 4'-trihydroxyisoflavones was blended to prepare a health beverage in a conventional manner.
9-6. 소세지9-6. sausage
돈육 65.18 중량%, 계육 25 중량%, 전분 3.5 중량%, 대두단백 1.7 중량%, 식염 1.62 중량%, 포도당 0.5 중량% 및 글리세린 1.5 중량%와 7,3',4'-트리하이드록시아이소플라본 1 중량%를 배합하여 통상의 방법으로 소세지를 제조하였다.65.18% pork, 25% poultry, 3.5% starch, 1.7% soy protein, 1.62% salt, 0.5% glucose and 1.5% glycerin and 7,3 ', 4'-trihydroxyisoflavones 1 Sausage was prepared by the conventional method by combining the weight percent.
9-7. 건강보조식품9-7. Health Supplement
스피루리나 55 중량%, 구아검효소 분해물 10 중량%, 비타민 B₁염산염 0.01중량%, 비타민 B6 염산염 0.01 중량%, DL-메티오닌 0.23 중량%, 스테아린산 마그네슘 0.7 중량%, 유당 22.2 중량% 및 옥수수전분 1.85 중량%와 7,3',4'-트리하이드록시아이소플라본 10 중량%를 배합하여 통상의 방법으로 정제형 건강보조식품을 제조하였다.55% by weight of spirulina, 10% by weight of guar gum enzyme digestion, 0.01% by weight of vitamin B₁ hydrochloride, 0.01% by weight of vitamin B6 hydrochloride, 0.23% by weight of DL-methionine, 0.7% by weight of magnesium stearate, 22.2% by weight of lactose and 1.85% by weight of corn starch And 7,3 ', 4'-trihydroxyisoflavones were blended to prepare a dietary supplement food in a conventional manner.
9-8. 주류9-8. mainstream
7,3',4'-트리하이드록시아이소플라본 0.5 %를 소주, 맥주, 양주 또는 과실주와 혼합하여 에멀전 상태로 만든 후, 진공상태에서 7,000 rpm으로 15분간 원심분리하거나 고속믹서기로 9,000 rpm에서 혼합하여 7,3',4'-트리하이드록시아이소플라본 혼합물이 함유된 주류를 제조하였다. 0.5% of 7,3 ', 4'-trihydroxyisoflavones are mixed with soju, beer, liquor or fruit liquor to make an emulsion, followed by centrifugation at 7,000 rpm for 15 minutes in a vacuum or at 9,000 rpm with a high speed mixer. Liquor containing 7,3 ', 4'-trihydroxyisoflavone mixtures was prepared.
도 1은 쥐 피부상피세포주 JB6 P+에서 자외선 조사에 의해 발생되는 싸이클로옥시게나제-2(cyclooxygenase-2, COX-2)의 발현에 있어 다이드제인은 효과가 없는 반면 7,3',4'-트리하이드록시아이소플라본의 억제 효능을 측정한 결과이다.FIG. 1 shows that the expression of cyclooxygenase-2 (COX-2) caused by ultraviolet irradiation in the rat dermal epithelial cell line JB6 P + has no effect while 7,3 ', 4' It is a result of measuring the inhibitory effect of -trihydroxyisoflavone.
도 2은 COX-2 프로모터 활성에 있어서 다이드제인은 억제효과가 없는 반면 7,3',4'-트리하이드록시아이소플라본은 저해 효능을 보인 결과이다. Figure 2 shows the result of showing the inhibitory effect of the Dyezein, 7,3 ', 4'-trihydroxyisoflavone while COX-2 promoter activity has no inhibitory effect.
도 3은 염증유발 전사인자인 NF-kB의 활성화에 있어서 다이드제인 보다 우수한 7,3',4'-트리하이드록시아이소플라본의 저해 효능을 측정 결과이다.Figure 3 shows the result of measuring the inhibitory effect of 7,3 ', 4'-trihydroxyisoflavones superior to the didase in the activation of NF-kB, an inflammation-inducing transcription factor.
도 4는 JB6 P+에 자외선을 조사하였을 경우 COX-2 발현을 조절하는 단백질인 p38, JNK(Jun N-terminal kinase) 의 인산화에 있어 7,3',4'-트리하이드록시아이소플라본의 저해 효능을 측정한 결과이다. Figure 4 shows the inhibitory effect of 7,3 ', 4'-trihydroxyisoflavones in phosphorylation of p38, JNK (Jun N-terminal kinase), a protein that regulates COX-2 expression when irradiated with ultraviolet light to JB6 P + Is the result of measuring.
도 5는 2단계 마우스 종양형성 모델에서 피부에서 자외선을 조사하였을 경우 종양 형성과 증가된 COX-2 발현에 있어 7,3',4'-트리하이드록시아이소플라본의 보호 효과를 측정한 결과이다. Figure 5 is a result of measuring the protective effect of 7,3 ', 4'-trihydroxyisoflavones in the tumor formation and increased COX-2 expression when the skin was irradiated with UV in a two-step mouse tumorigen model.
도 6은 인간 피부 표피세포인 HaCa T 세포에 자외선 조사에 의해 발생되는 MMP-1 의 활성에 있어 7,3',4'-트리하이드록시아이소플라본의 억제 효과를 측정한 결과이다.Fig. 6 shows the results of measuring the inhibitory effect of 7,3 ', 4'-trihydroxyisoflavones on the activity of MMP-1 generated by UV irradiation on HaCa T cells, which are human skin epidermal cells.
도 7은 HaCa T 세포에서 MMP-1의 발현을 조절하는 전사인자인 AP-1의 활성화에 있어서 7,3',4'-트리하이드록시아이소플라본의 억제 효과를 측정한 결과이다. 7 shows the results of measuring the inhibitory effect of 7,3 ', 4'-trihydroxyisoflavones on the activation of AP-1, a transcription factor that regulates the expression of MMP-1 in HaCa T cells.
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|---|---|
| KR (1) | KR20100092626A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150049667A (en) * | 2013-10-30 | 2015-05-08 | 서울대학교산학협력단 | Composition for improving atopic skin comprising 7, 8, 4'-trihydroxyisoflavone as active ingredient |
-
2009
- 2009-02-13 KR KR1020090011837A patent/KR20100092626A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150049667A (en) * | 2013-10-30 | 2015-05-08 | 서울대학교산학협력단 | Composition for improving atopic skin comprising 7, 8, 4'-trihydroxyisoflavone as active ingredient |
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