KR101943302B1 - Skin external application composition and cosmetic composition comprising ellagic acid and dihydromyricetin - Google Patents
Skin external application composition and cosmetic composition comprising ellagic acid and dihydromyricetin Download PDFInfo
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- KR101943302B1 KR101943302B1 KR1020170009488A KR20170009488A KR101943302B1 KR 101943302 B1 KR101943302 B1 KR 101943302B1 KR 1020170009488 A KR1020170009488 A KR 1020170009488A KR 20170009488 A KR20170009488 A KR 20170009488A KR 101943302 B1 KR101943302 B1 KR 101943302B1
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- South Korea
- Prior art keywords
- skin
- dihydromyricetin
- dhm
- ega
- ellagic acid
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- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 title claims abstract description 86
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- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
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- 239000000341 volatile oil Substances 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
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Abstract
본 발명은 엘라그산(ellagic acid) 또는 디하이드로미리세틴(dihydromyricetin)을 유효성분으로 함유하는 피부 외용제 및 화장료 조성물에 관한 것으로, 구체적으로 본 발명의 엘라그산 또는 디하이드로미리세틴은 자외선에 의한 홍반, 광노화, 염증 등을 유의적으로 억제하고, 특히 엘라그산 및 디하이드로미리세틴을 병용처리할 경우, 현저한 상승적(synergistic) 효과를 나타내므로, 엘라그산 또는 디하이드로미리세틴는 자외선 차단용 피부 외용제, 및 피부노화 개선, 항염증, 항산화, 피부주름 개선 등 다양한 용도의 화장료 조성물로 유용하게 사용될 수 있다.The present invention relates to an external preparation for skin and a cosmetic composition containing ellagic acid or dihydromyricetin as an active ingredient. More specifically, the present invention relates to an external preparation for skin and cosmetic composition, Photoinitiator, inflammation and the like are remarkably inhibited, and in particular, a combination of eragic acid and dihydroimiricetin exhibits a remarkable synergistic effect, so that eragic acid or dihydroimisetin is a skin external preparation for ultraviolet screening, Anti-aging, anti-inflammation, antioxidation, skin wrinkle improvement, and the like.
Description
본 발명은 엘라그산(ellagic acid), 디하이드로미리세틴(dihydromyricetin), 또는 이의 혼합물을 유효성분으로 함유하는 자외선 차단용 피부 외용제, 및 자외선 차단, 피부 광손상 개선, 피부노화 개선, 항염증, 항산화, 피부주름 개선 및 피부탄력 개선용 용도를 갖는 화장료 조성물에 관한 것이다.
The present invention relates to an ultraviolet screening external preparation for external sunscreen containing ellagic acid, dihydromyricetin, or a mixture thereof as an active ingredient, and a cosmetic composition for ultraviolet screening, skin light damage improvement, skin aging improvement, , Skin wrinkles, and skin elasticity.
피부의 노화는 크게 생물학적 과정에 따라 시간이 지나면서 나타나는 연대학적 노화(내인적인 노화)와 햇볕에 노출되는 부위에 일어나는 퇴행성 변화와 연대학적 노화가 복합적으로 발생하는 광노화(광인성 노화)로 구분된다. 광노화에서는 피부가 건조해지고 거칠어지며 두꺼워지는 반면 연대학적 노화에서는 오히려 피부가 얇고 매끄러워진다. 이 밖에도 광노화에서는 연대학적 노화와는 다르게 깊은 주름이 생기고 이완, 얼룩진 과색소 침착과 저색소 침착, 모세 혈관 확장, 자반, 가성반흔 등이 나타난다. 이외에도 연대학적 노화와 광노화는 여러 가지 임상 양상의 차이가 있다.
Skin aging is largely classified into chronological aging (internal aging) that develops over time according to biological processes, photoaging (photo-aging) in which degenerative changes and chronological aging occur in sun exposure . In photoaging, skin becomes dry, rough and thick, whereas in chronological aging, skin becomes thinner and smoother. In addition, in photoaging, deep wrinkles are formed unlike chronological aging, and there are relaxation, stained hyperchromatic hyperpigmentation, hypopigmentation, capillary dilatation, sputum and caustic scars. In addition, chronological aging and photoaging have different clinical features.
햇빛에 의한 손상은 피부노화의 주요 원인으로 광노화를 발생시키는 주요 원인은 자외선이다. 자외선은 그 파장의 길이에 따라 UV-A, B, C로 나눌 수 있는데, 이중 UV-A(320-400 nm)는 피부에 대한 자극이 미약하여 UV-B보다는 피부에 해가 적지만 오랫동안 노출될 경우 기미나 검버섯 등의 색소 침착이 일어나고 피부 노화를 심화시킬 뿐 아니라, 심한 경우 피부암까지 발생시킬 수 있다. UV-C(200-280 nm)는 X선과 근접한 파장을 가진 광선으로 발암성이 매우 높지만 오존층에 의해 모두 차단되므로 별도로 차단해야 할 필요는 없다. UV-B(280-320 nm)는 인체에 가장 쉽고 빠르게 영향을 나타내어 피부손상에 관여하며 건조 및 피부홍반, 색소침착, 표피비후 등의 현상과 산화적 스트레스 및 항산화 기전의 불균형 유발을 통해 피부를 구성하는 지질, 단백질, 효소 등을 손상시킴으로써 염증반응과 피부암 및 광노화를 심화시켜 피부손상을 초래한다. 특히 UV-B 노출에 의해 생성이 유도되는 활성산소종(reactive oxygen species, ROS)은 광노화 주요원인 중 하나로 세포내 신호전달 체계를 자극하여 DNA와 지질 및 단백질과 같은 생체분자에 산화적 스트레스 유발을 통한 피부조직 손상을 야기한다. 또한, 활성산소종은 표피 각질세포와 진피 섬유아세포의 자극으로 활성화 단백질(activator protein-1, AP-1) 및 핵인자 카파 B(nuclear factor kappa-light-chain-enhancer of activated B cells, NF-κB)의 전사인자를 활성화하고 염증관련 사이토카인(cytokine)을 분비토록 하여 콜라겐 분해효소들(matrix metalloproteinase, MMPs)의 발현을 증가시킨다. 증가된 콜라겐 분해효소들(MMPs)은 피부의 콜라겐을 분해한다. 콜라겐은 피부의 주요 구성 성분으로 진피층의 경우 90%를 차지하고 있고 피부에 강도와 장력을 부여하며 이로 인해 외부의 자극이나 힘으로부터 피부를 보호하는 역할을 하고 있기 때문에 자외선 노출에 의한 콜라겐 분해효소들(MMPs)의 발현증가에 따른 콜라겐의 감소는 피부 노화와 주름형성을 유발한다. 따라서 체내에서는 활성산소에 의해 생성 및 활성화된 지질과산화물(lipid peroxide)과 산화효소에 대한 방어로 카탈라아제(catalase, CAT), 수퍼옥사이드 디스뮤타아제(superoxide dismutase, SOD) 및 글루타티온 S-전달효소(glutathione-s-transferase, GST) 등과 같은 항산화 효소가 작용하여 활성산소에 의한 피부 손상을 방어할 수 있는 것으로 알려져 있다. 또한 UV-B 조사는 각질형성세포(keratinocyte)가 종양괴사인자-알파(tumour necrosis factor-α, TNF-α), 인터루킨-1베타(interleukin-1β, IL-1β), IL-6, IL-10 와 IL-8을 세포 외로 분비하도록 자극하여 염증을 유도한다. 특히 TNF-α는 초기 자극에 대한 중요한 염증 유발인자로서 염증반응을 유도해 유도형 NO 생성효소(inducible NO synthase, iNOS) 발현이 증가시키고 iNOS에 의해 생성된 염증매개 물질인 NO는 피부 세포에서 콜라겐 생성에 중요한 영향을 끼칠 뿐 아니라 피부 세포 성장에 주요한 역할을 한다고도 알려져 있다.
Damage caused by sunlight is the main cause of skin aging. Ultraviolet rays are the main cause of photoaging. Ultraviolet rays can be divided into UV-A, B, and C depending on the wavelength. UV-A (320-400 nm) is less harmful to the skin than UV-B, , Pigmentation such as spots or black spots occurs and not only deepens skin aging but also can cause skin cancer even in severe cases. UV-C (200-280 nm) is a ray of light with a wavelength close to that of X-rays, but it is highly carcinogenic. UV-B (280-320 nm) has the easiest and fastest effect on the human body and it is involved in skin damage. It is affected by skin irritation, pigmentation, skin thickening and oxidative stress and unbalance of antioxidant mechanism. It damages the constituent lipids, proteins, enzymes, etc., thereby deepening the inflammation reaction, skin cancer and photoaging, resulting in skin damage. In particular, reactive oxygen species (ROS), which is induced by UV-B exposure, is one of the major causes of photoaging. It stimulates intracellular signaling pathways and induces oxidative stress on biomolecules such as DNA, lipids and proteins Resulting in damage to the skin tissue. In addition, the active oxygen species were activated by the stimulation of epidermal keratinocytes and dermal fibroblasts with activator protein-1 (AP-1) and nuclear factor kappa-light-chain-enhancer of activated B cells (NF- κB) and increases the expression of matrix metalloproteinases (MMPs) by secretion of inflammatory cytokines. Increased collagenase (MMPs) break down collagen in the skin. Collagen is a major constituent of the skin, which accounts for 90% of the dermal layer, and gives strength and tension to the skin, which protects the skin from external stimuli or forces. Therefore, collagen degradation enzymes Decreased collagen with increased expression of MMPs leads to skin aging and wrinkling. Therefore, in the body, as a defense against lipid peroxide and oxidase produced and activated by active oxygen, catalase (CAT), superoxide dismutase (SOD) and glutathione S-transferase -s-transferase, GST), which is known to inhibit skin damage caused by reactive oxygen species. In addition, UV-B irradiation can be induced by keratinocyte in tumor necrosis factor-α, interleukin-1β, IL-6, IL- 10 and IL-8 to the extracellular secretion to induce inflammation. In particular, TNF-α is an important inflammatory inducer for early stimulation and induces inflammatory response to increase expression of inducible NO synthase (iNOS). NO, an inflammatory mediator produced by iNOS, It is also known to play a major role in skin cell growth as well as to have a significant impact on production.
엘라그산(ellagic acid)은 폴리페놀 4개의 링으로 구성되어 있으며, 식물체 내에서는 전구물질인 엘라기탄닌(ellagitannin) 형태로 존재하며, 포도, 딸기, 석류, 나무딸기, 땅콩류 및 녹차 등에 존재하는 식물성 페놀물질로 항 돌연변이 및 항암기능이 있는 것이 알려져 있으며, 디하이드로미리세틴(dihydromyricetin)은 기름모과나무(Xanthoceras sorbifolia), 고산지대 코카인 식물(Catha edulis)로부터 분리된다고 알려져 있으나, 엘라그산과 함께 유의적인 자외선 차단 효과, 피부노화 개선, 항염증, 항산화, 피부주름 개선 및 피부탄력 개선효과를 나타낼 수 있음은 전혀 알려져 있지 않다.
Ellagic acid is composed of four rings of polyphenols and exists in the form of ellagitannin, a precursor in the plant. It is also present in plants such as grape, strawberry, pomegranate, raspberry, It is known that phenolic materials have antimutagenic and anticancer properties, and dihydromyricetin is known to be a potent antioxidant for Xanthoceras sorbifolia , high altitude cocaine plants ( Catha edulis ). However, it is not known that it can exhibit significant UV blocking effect, skin aging improvement, anti-inflammation, antioxidation, skin wrinkle improvement and skin elasticity improvement effect together with erlage acid.
한편, 항노화를 위한 대표적인 피부 주름 개선 물질로 알려진 레티놀, 레티노이드 및 그 유도체들의 경우 콜라겐 분해효소(MMP-1)를 억제해 콜라겐 손실을 방지하여 내인성 및 광노화를 방지하고 회복시키는 것으로 알려져 있으나 홍반, 가려움, 건선 등의 국소적 피부 부작용을 일으킬 수 있다고 알려져 있으며 피부 염증 또는 트러블에는 아직까지 안정성에 논란이 되고 있는 스테로이드 또는 비스테로이드계의 합성 물질 또는 신경 펩타이드 길항제 등이 이용되는 경우가 많다.
On the other hand, it is known that retinol, retinoid and derivatives thereof, which are known as anti-aging agents for skin wrinkles, inhibit collagen degradation enzyme (MMP-1) to prevent collagen loss and prevent and recover endogenous and photoaging, Itch, and psoriasis. Steroids or nonsteroidal synthetic substances or neuropeptide antagonists, which are still controversial for skin irritation or trouble, are often used.
따라서, 본 발명자들은 부작용이 적은 자외선 차단용 조성물, 광손상 또는 피부노화 개선용 조성물을 제조하기 위해 노력한 결과, 엘라그산(ellagic acid) 또는 디하이드로미리세틴(dihydromyricetin)은 자외선에 의한 홍반, 광노화, 염증 등을 유의적으로 억제하고, 특히 엘라그산 및 디하이드로미리세틴을 병용처리할 경우, 현저한 상승적(synergistic) 효과를 나타냄을 확인함으로써, 상기 엘라그산(ellagic acid) 또는 디하이드로미리세틴(dihydromyricetin)을 자외선 차단용 피부 외용제, 및 자외선 차단, 피부 광손상 개선, 피부노화 개선, 항염증, 항산화, 피부주름 개선 및 피부탄력 개선용 용도를 갖는 화장료 조성물로 유용하게 사용될 수 있음을 밝힘으로써, 본 발명을 완성하였다.
Accordingly, the present inventors have made efforts to produce a composition for protecting ultraviolet light, a composition for improving photodamage or skin aging, which has few side effects, and as a result, ellagic acid or dihydromyricetin has been found to be effective for erythema, Inflammation and the like, and in particular, when it is confirmed that a synergistic effect is exhibited when the combination of eragic acid and dihydroimiricetin is used, the above-mentioned ellagic acid or dihydromyricetin, Can be effectively used as a cosmetic composition having an external application for skin protecting against ultraviolet rays and a use for ultraviolet ray shielding, skin light damage improvement, skin aging, anti-inflammation, antioxidation, skin wrinkle improvement and skin elasticity improvement. .
본 발명의 목적은 엘라그산(ellagic acid), 디하이드로미리세틴(dihydromyricetin) 또는 이의 혼합물을 유효성분으로 함유하는 피부 외용제, 또는 화장료 조성물을 제공하기 위한 것이다.
An object of the present invention is to provide an external preparation for skin or a cosmetic composition containing ellagic acid, dihydromyricetin or a mixture thereof as an active ingredient.
상기 목적을 달성하기 위하여, 본 발명은 엘라그산(ellagic acid) 및 디하이드로미리세틴(dihydromyricetin), 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 자외선 차단용 피부 외용제를 제공한다.In order to achieve the above object, the present invention provides an ultraviolet screening external preparation for skin which comprises, as an active ingredient, ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof.
또한, 본 발명은 엘라그산(ellagic acid) 및 디하이드로미리세틴(dihydromyricetin), 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 화장료 조성물을 제공한다.The present invention also provides a cosmetic composition comprising, as an active ingredient, ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof.
또한, 본 발명은 엘라그산(ellagic acid) 및 디하이드로미리세틴(dihydromyricetin), 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 피부 광손상 예방 및 치료용 피부 외용제를 제공한다.The present invention also provides an external preparation for skin for the prevention and treatment of skin damage, comprising ellagic acid, dihydromyricetin, or a pharmaceutically acceptable salt thereof as an active ingredient.
또한, 본 발명은 엘라그산(ellagic acid), 디하이드로미리세틴(dihydromyricetin) 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 자외선 차단용 피부 외용제를 제공한다.The present invention also provides an ultraviolet screening external preparation for skin which contains, as an active ingredient, ellagic acid, dihydromyricetin or a pharmaceutically acceptable salt thereof.
아울러, 본 발명은 엘라그산(ellagic acid), 디하이드로미리세틴(dihydromyricetin) 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 화장료 조성물을 제공한다.
In addition, the present invention provides a cosmetic composition comprising, as an active ingredient, ellagic acid, dihydromyricetin or a pharmaceutically acceptable salt thereof.
본 발명의 엘라그산(ellagic acid), 디하이드로미리세틴(dihydromyricetin) 또는 이의 혼합물은 자외선에 의한 홍반, 광노화, 염증 등을 유의적으로 억제하고, 특히 엘라그산 및 디하이드로미리세틴을 병용처리할 경우, 현저한 상승적(synergistic) 효과를 나타내므로, 엘라그산 또는 디하이드로미리세틴은 자외선 차단용 피부 외용제, 및 피부노화 개선, 항염증, 항산화, 피부주름 개선 등 다양한 용도의 화장료 조성물로 유용하게 사용될 수 있다.
The ellagic acid, dihydromyricetin, or a mixture thereof of the present invention significantly inhibits erythema, photoaging, inflammation, and the like caused by ultraviolet rays, and particularly when a combination of eragic acid and dihydromyricetin is used , It exhibits a remarkable synergistic effect. Therefore, eragic acid or dihydroimisetin can be effectively used as a cosmetic composition for various purposes such as skin external application for ultraviolet ray shielding, improvement of skin aging, anti-inflammation, antioxidation, skin wrinkle improvement .
도 1은 엘라그산(ellagic acid; EGA) 또는 디하이드로미리세틴(dihydromyricetin; DHM) 처리 후, UV 조사에 의한 세포사멸 억제효과를 확인한 도이다.
도 2는 EGA 또는 DHM 처리 후, UV 조사에 따른 TBAES 및 ROS를 확인한 도이다.
도 3은 자외선 조사 후, Collagen 1 및 MMP-1의 발현에 대한 EGA 또는 DHM의 효과를 확인한 도이다.
도 4는 자외선 조사 후, Cu/Mn SOD 및 TNF-a의 발현에 대한 EGA 또는 DHM의 효과를 확인한 도이다.
도 5는 동물실험 방법을 개시한 도이다.
도 6은 본 발명의 동물실험에서 마우스에 UV를 처리하는 모습을 나타낸 도이다.
도 7은 본 발명의 동물 실험에서 UV 조사 후, 피부의 변화를 나타낸 도이다.
도 8은 본 발명의 동물 실험에서 UV 조사 후, 홍반 정도의 변화를 나타낸 도이다.
도 9는 본 발명의 동물 실험에서 UV 조사 후, 화상 정도의 변화를 나타낸 도이다.
도 10은 본 발명의 동물 실험에서 UV 조사 후, 짖물음 정도의 변화를 나타낸 도이다.
도 11은 본 발명의 동물 실험에서 UV 조사 후, 상처 정도의 변화를 나타낸 도이다.
도 12는 본 발명의 동물 실험에서 등 조직의 조직학적 변화를 나타낸 도이다.
도 13은 본 발명의 동물 실험에서 UV 조사 후, 표피 및 진피의 두께 변화를 나타낸 도이다.
도 14는 본 발명의 동물 실험에서 UV 조사 후 mast cell의 수를 나타낸 도이다.1 is a graph showing the effect of inhibiting cell death by UV irradiation after treatment with ellagic acid (EGA) or dihydromyricetin (DHM).
Fig. 2 is a view showing TBAES and ROS according to UV irradiation after EGA or DHM treatment. Fig.
FIG. 3 shows the effect of EGA or DHM on the expression of
FIG. 4 shows the effect of EGA or DHM on the expression of Cu / Mn SOD and TNF-a after UV irradiation.
Fig. 5 is a view for explaining an animal experimental method. Fig.
FIG. 6 is a diagram showing a state in which mice are treated with UV in an animal experiment of the present invention. FIG.
Fig. 7 is a diagram showing changes in skin after UV irradiation in the animal experiment of the present invention. Fig.
Fig. 8 is a graph showing changes in the degree of erythema after UV irradiation in the animal experiment of the present invention. Fig.
Fig. 9 is a diagram showing a change in the degree of image after UV irradiation in the animal experiment of the present invention. Fig.
10 is a graph showing changes in the degree of barking after UV irradiation in the animal experiment of the present invention.
Fig. 11 is a graph showing changes in degree of wound after UV irradiation in the animal experiment of the present invention. Fig.
Figure 12 is a diagram showing histological changes of the back tissue in the animal experiment of the present invention.
Fig. 13 is a graph showing changes in the thickness of epidermis and dermis after UV irradiation in the animal experiment of the present invention. Fig.
14 is a graph showing the number of mast cells after UV irradiation in the animal experiment of the present invention.
이하, 본 발명을 상세한 설명한다.
Hereinafter, the present invention will be described in detail.
본 발명은 엘라그산(ellagic acid) 및 디하이드로미리세틴(dihydromyricetin), 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 자외선 차단용 피부 외용제 또는, 광손상 예방 또는 치료용 피부 외용제를 제공한다.The present invention provides an ultraviolet screening external preparation for skin which contains ellagic acid and dihydromyricetin or a pharmaceutically acceptable salt thereof as an active ingredient or a skin external preparation for preventing or treating photodamage do.
상기 엘라그산은 포도, 딸기, 석류, 나무딸기, 땅콩류 및 녹차 등에서 추출하거나, 합성한 것 모두 무방하게 사용될 수 있다. The above-mentioned elagic acid may be extracted from grapes, strawberries, pomegranates, raspberries, peanuts and green tea, or may be used in a synthetic manner.
상기 디하이드로미리세틴은 기름모과나무(Xanthoceras sorbifolia), 고산지대 코카인 식물(Catha edulis)으로부터 추출하거나, 합성한 것 모두 무방하게 사용될 수 있다. The dihydroimylsethin is an antioxidant, sorbifolia , high altitude cocaine plants ( Catha edulis ), and the like.
상기 엘라그산 및 디하이드로미리세틴은 1 : 0.1 내지 10의 비율로 혼합할 수 있으나, 이에 한정되지 않는다.The elastase and dihydroimylsethine may be mixed in a ratio of 1: 0.1 to 10, but are not limited thereto.
상기 엘라그산은 하기 [화학식 1]로 기재되는 화합물인 것이 바람직하고, 상기 디하이드로미리세틴은 하기 [화학식 2]로 기재되는 화합물인 것이 바람직하며, 본 발명과 동일한 활성을 갖는 상기 화합물의 유도체도 본 발명에 포함된다.The above-mentioned ellagic acid is preferably a compound described by the following
[화학식 1][Chemical Formula 1]
[화학식 2](2)
상기 외용제는 피부 주름, 홍반 또는 피부 짖물음을 개선하고, 피부를 재생하며, 피부의 염증을 예방, 개선 또는 치료하는 효과를 나타낸다. 또한, 상기 외용제는 노화, 피부 광손상, 보다 구체적으로 UV에 의한 광노화, 산화 또는 염증을 억제할 수 있고, 더욱 더 구체적으로 UV-B에 의한 노화, 산화 또한 염증을 억제할 수 있다.
The above external preparations have the effect of improving skin wrinkles, erythema or skin irritation, regenerating the skin, preventing, ameliorating or treating inflammation of the skin. In addition, the external preparation can inhibit aging, skin photodamage, more specifically UV-induced photo-aging, oxidation or inflammation, and more particularly, can suppress aging, oxidation and inflammation by UV-B.
본 발명의 구체적인 실시예에서, 본 발명자는 광노화에 대한 엘라그산, 디하이드로미리세틴 또는 이들의 병용처리 효과를 확인하기 위하여, UVB 조사에 의한 세포사멸 억제 효과를 확인한 결과, EGA 는 DHM 처리군에서 세포 사멸이 감소하였고, 특히 EGA 및 DHM를 병용처리군은 상승적으로(synergistic) 세포사멸을 억제하는 것을 확인하였다(도 1 참조).In a specific example of the present invention, the present inventors confirmed the effect of inhibiting cell death by UVB irradiation in order to confirm the effect of the treatment with elagance, dehydroximysin, or their combination on photoaging. As a result, The cell death was reduced, and in particular, the combination treatment of EGA and DHM inhibited synergistic cell death (see FIG. 1).
또한, 본 발명자는 자외선으로 인해 세포에서 생성되는 자유라디칼이 지질을 과산화시켜 과산화물을 생성하고, 이러한 과산화물은 세포막과 핵산의 손상을 일으켜 세포사멸을 나타내므로, EGA 또는 DHM의 UVB 조사에 의한 지질과산화물(lipid peroxide) 생성 억제효과를 확인한 결과, EGA 또는 DHM 처리군은 효과적으로 자외선으로 인해 생성되는 과산화물의 함량을 감소시켜고, 특히 EGA 및 DHM를 병용 처리군은 상승적으로(synergistic) 과산화물의 함량을 감소시키는 것을 확인하였다(도 2 참조).In addition, the inventor of the present invention found that free radicals generated in cells due to ultraviolet rays peroxidize lipids to produce peroxides, and these peroxides cause cell membrane and nucleic acid damage, leading to apoptosis. Therefore, lipid peroxides produced by UVB irradiation of EGA or DHM (EGA) or DHM (DHM) treatment decreased the amount of peroxide produced by ultraviolet light. Especially, the combination treatment of EGA and DHM decreased the synergistic peroxide content (See FIG. 2).
또한, 본 발명자는 자외선 조사 후, 항산화 또는 항염증 등에 관여하는 유전자에 대한 EGA 또는 DHM의 효과를 확인한 결과, EGA 또는 DHM는 collagen-1의 발현을 증가시키고, MMP1의 발현을 유의적으로 감소시켜 유의적인 피부 재생 효과를 갖는 것을 확인하였다(도 3 참조).The present inventors also confirmed the effect of EGA or DHM on genes involved in antioxidative or antiinflammation after ultraviolet irradiation. As a result, EGA or DHM increased the expression of collagen-1 and significantly decreased the expression of MMP1 (See Fig. 3).
또한, 자외선으로 생성된 자유라디칼을 제거하는 효소인 SOD의 발현은 EGA 또는 DHM에 의해서 효과적으로 증가하였고, 특히 EGA 및 DHM를 병용처리할 경우, SOD의 발현을 현저하게 증가시키는 것을 확인하였다. 또한, 염증 반응과 관련된 TNF-α의 발현은 EGA 또는 DHM에 의해서 효과적으로 감소하였고, 특히 EGA 및 DHM를 병용처리할 경우, TNF-α의 발현을 현저하게 감소되는 것을 확인하였다(도 4 참조).In addition, the expression of SOD, an enzyme that eliminates free radicals generated by ultraviolet light, was effectively increased by EGA or DHM, and especially when EGA and DHM were used in combination, the expression of SOD was remarkably increased. In addition, the expression of TNF-a in association with the inflammatory reaction was effectively reduced by EGA or DHM, and the expression of TNF-a was remarkably decreased when EGA and DHM were used in combination (see Fig. 4).
또한, 본 발명자는 광노화가 유도된 동물모델에서 EGA 또는 DHM의 효과를 확인한 결과, UV 노출로 인해, 대조군은 홍반이 나타나고 짖물음, 화상 등이 심해진 반면, EGA군과 DHM군은 대조군에 비해서 홍반과 화상이 가장 적었고 짖물음도 쉽게 없어지는 것을 볼 수 있었고, 특히 EGA+DHM이 가장 효과적으로 홍반, 짖물음, 화상이 없어지고 정상 상태로 회복되는 것을 확인하였다(도 7 내지 도 14).In addition, the present inventors confirmed the effects of EGA or DHM on the photoaging induced animal model. As a result of UV exposure, the control group showed erythema, barking, burning, etc., whereas EGA group and DHM group showed erythema (Fig. 7 to Fig. 14). In particular, EGA + DHM showed the most effective elimination of erythema, barking, and burning and recovery to a normal state (Figs. 7 to 14).
따라서, 본 발명의 엘라그산(ellagic acid), 디하이드로미리세틴(dihydromyricetin) 또는 이들의 혼합물은 자외선에 의한 홍반, 광노화, 염증 등을 유의적으로 억제하고, 특히 엘라그산 및 디하이드로미리세틴을 병용처리할 경우, 현저한 상승적(synergistic) 효과를 나타내므로, 엘라그산 또는 디하이드로미리세틴는 피부 주름, 홍반 또는 피부 짖물음을 개선하고, 피부를 재생하며, 피부의 염증을 예방, 개선 또는 치료하는 효과를 갖는 자외선 차단용 피부 외용제로 유용하게 사용될 수 있다.
Therefore, the ellagic acid, dihydromyricetin, or a mixture thereof of the present invention significantly inhibits erythema caused by ultraviolet rays, photoaging, inflammation and the like, and particularly, in combination with eragic acid and dihydroimisetin When treated, it exhibits a remarkable synergistic effect, so that eragic acid or dihydroimlisetin improves skin wrinkles, erythema or skin irritation, regenerates skin, and prevents, improves or cures inflammation of the skin As a skin external preparation for ultraviolet ray shielding.
본 발명의 효과를 위하여, 적합한 외용 제형을 선택하는 것이 중요하다. 따라서, EGA 또는 DHM을 환부에 효과적으로 적용될 수 있도록 연고제로 제조할 수 있다. 상기 연고제는 본 발명의 EGA 또는 DHM, 또는 이의 혼합물을 무기물질과 배합한 다음, 이를 지용성 기제로 코팅하여 제조한다. 상기 무기물질은 항균성, 소염효과, 표피재생 효과 등이 우수한 소재를 사용하는 것이 바람직하고, 이들의 구체적인 예로는 산화아연, 탄산아연, 산화철 등이 있다. 또한, 본 발명 화합물을 안전하게 함침할 수 있는 세라믹 담체를 추가로 사용하는 것이 바람직하다. 상기 세라믹 담체로는 제올라이트, 활석, 석고, 모려분 및 이들의 혼합물이 바람직하게 사용된다. 이러한 세라믹 담체는 수용성 성분의 함침성이 우수하여 피부에 수용성 성분의 공급을 원활히 할 수 있다.For the effect of the present invention, it is important to select a suitable external dosage form. Therefore, EGA or DHM can be manufactured as an ointment so that it can be effectively applied to the affected part. The ointment agent is prepared by combining the EGA or DHM of the present invention or a mixture thereof with an inorganic substance and then coating it with a liposoluble base. The inorganic material is preferably a material having excellent antimicrobial activity, anti-inflammatory effect, epidermal regeneration effect, etc. Specific examples thereof include zinc oxide, zinc carbonate, iron oxide and the like. Further, it is preferable to further use a ceramic carrier capable of safely impregnating the compound of the present invention. As the ceramic carrier, zeolite, talc, gypsum, mortar and mixtures thereof are preferably used. Such a ceramic carrier is excellent in the impregnation property of the water-soluble component, so that the water-soluble component can be smoothly supplied to the skin.
또한, 피부 외용제로 사용하는 경우, 추가로 지방 물질, 유기 용매, 용해제, 농축제 및 겔화제, 연화제, 항산화제, 현탁화제, 안정화제, 발포제(foaming agent), 방향제, 계면활성제, 물, 이온형 또는 비이온형 유화제, 충전제, 금속이온 봉쇄제 및 킬레이트화제, 보존제, 비타민, 차단제, 습윤화제, 필수 오일, 염료, 안료, 친수성 또는 친유성 활성제, 지질 소낭 또는 피부용 외용제에 통상적으로 사용되는 임의의 다른 성분과 같은 피부 과학 분야에서 통상적으로 사용되는 보조제를 함유할 수 있다. 또한, 상기 성분들은 피부 과학 분야에서 일반적으로 사용되는 양으로 도입될 수 있다.
In addition, when used as an external preparation for skin, it may further comprise at least one selected from the group consisting of fatty substances, organic solvents, solubilizers, thickeners and gelling agents, softening agents, antioxidants, suspending agents, stabilizing agents, foaming agents, Any of those commonly used in emulsifying or emulsifying agents, fillers, sequestering and chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, ≪ / RTI > and other ingredients of the skin. In addition, the components can be introduced in amounts commonly used in the dermatology field.
본 발명은 화학식 1 또는 화학식 2로 표시되는 화합물뿐 아니라, 이의 약학적으로 허용되는 염, 이로부터 제조될 수 있는 가능한 용매화물, 수화물, 라세미체, 또는 입체이성질체를 모두 포함한다.The present invention includes all of the compounds represented by Formula (1) or (2) as well as pharmaceutically acceptable salts thereof, and possible solvates, hydrates, racemates, or stereoisomers thereof.
본 발명의 화학식 1로 표시되는 엘라그산, 화학식 2로 표시되는 디하이드로미리세틴은 약학적으로 허용 가능한 염의 형태로 사용할 수 있으며, 염으로는 약학적으로 허용 가능한 유리산(free acid)에 의해 형성된 산 부가염이 유용하다. 산 부가염은 염산, 질산, 인산, 황산, 브롬화수소산, 요드화수소산, 아질산 또는 아인산과 같은 무기산류와 지방족 모노 및 디카르복실레이트, 페닐-치환된 알카노에이트, 하이드록시 알카노에이트 및 알칸디오에이트, 방향족 산류, 지방족 및 방향족 설폰산류와 같은 무독성 유기산으로부터 얻는다. 이러한 약학적으로 무독한 염류로는 설페이트, 피로설페이트, 바이설페이트, 설파이트, 바이설파이트, 니트레이트, 포스페이트, 모노하이드로겐 포스페이트, 디하이드로겐 포스페이트, 메타포스페이트, 피로포스페이트 클로라이드, 브로마이드, 아이오다이드, 플루오라이드, 아세테이트, 프로피오네이트, 데카노에이트, 카프릴레이트, 아크릴레이트, 포메이트, 이소부티레이트, 카프레이트, 헵타노에이트, 프로피올레이트, 옥살레이트, 말로네이트, 석시네이트, 수베레이트, 세바케이트, 푸마레이트, 말리에이트, 부틴-1,4-디오에이트, 헥산-1,6-디오에이트, 벤조에이트, 클로로벤조에이트, 메틸벤조에이트, 디니트로 벤조에이트, 하이드록시벤조에이트, 메톡시벤조에이트, 프탈레이트, 테레프탈레이트, 벤젠설포네이트, 톨루엔설포네이트, 클로로벤젠설포네이트, 크실렌설포네이트, 페닐아세테이트, 페닐프로피오네이트, 페닐부티레이트, 시트레이트, 락테이트, 하이드록시부티레이트, 글리콜레이트, 말레이트, 타트레이트, 메탄설포네이트, 프로판설포네이트, 나프탈렌-1-설포네이트, 나프탈렌-2-설포네이트 또는 만델레이트를 포함한다.
Elagic acid represented by formula (1) of the present invention and dihydroximysin represented by formula (2) may be used in the form of a pharmaceutically acceptable salt. Examples of salts include salts formed by pharmaceutically acceptable free acids Acid addition salts are useful. Acid addition salts include those derived from inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid or phosphorous acid, and aliphatic mono- and dicarboxylates, phenyl-substituted alkanoates, hydroxyalkanoates, Dioleate, aromatic acid, aliphatic and aromatic sulfonic acids. Such pharmaceutically innocuous salts include, but are not limited to, sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihydrogenphosphate, metaphosphate, pyrophosphate chloride, bromide, Butyrate, caprate, heptanoate, propiolate, oxalate, malonate, succinate, succinate, maleic anhydride, maleic anhydride, , Sebacate, fumarate, maleate, butyne-1,4-dioate, hexane-1,6-dioate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, hydroxybenzoate, Methoxybenzoate, phthalate, terephthalate, benzene sulfonate, toluene sulfonate, chlorobenzene sulfide Sulfonate, methanesulfonate, propanesulfonate, naphthalene-1-sulphonate, naphthalene-1-sulphonate, , Naphthalene-2-sulfonate or mandelate.
본 발명에 따른 산 부가염은 통상의 방법, 예를 들면, 화합물을 과량의 산 수용액 중에 용해시키고, 이 염을 수혼화성 유기 용매, 예를 들면 메탄올, 에탄올, 아세톤 또는 아세토니트릴을 사용하여 침전시켜서 제조할 수 있다. 또한, 이 혼합물에서 용매나 과량의 산을 증발시켜서 건조하거나 또는 석출 된 염을 흡입 여과시켜 제조할 수도 있다.
The acid addition salt according to the present invention can be prepared by a conventional method, for example, by dissolving the compound in an excess amount of an aqueous acid solution and precipitating the salt using a water-miscible organic solvent such as methanol, ethanol, acetone or acetonitrile Can be manufactured. It is also possible to prepare the mixture by evaporating a solvent or an excess acid in the mixture, or by suction filtration of the precipitated salt.
또한, 염기를 사용하여 약학적으로 허용 가능한 금속염을 만들 수 있다. 알칼리 금속 또는 알칼리 토금속 염은, 예를 들면 화합물을 과량의 알칼리 금속 수산화물 또는 알칼리 토금속 수산화물 용액 중에 용해하고, 비용해 화합물 염을 여과하고, 여액을 증발, 건조시켜 얻는다. 이때, 금속염으로는 나트륨, 칼륨 또는 칼슘염을 제조하는 것이 제약상 적합하다. 또한, 이에 대응하는 은 염은 알칼리 금속 또는 알칼리 토금속 염을 적당한 음염(예, 질산은)과 반응시켜 얻는다.
In addition, bases can be used to make pharmaceutically acceptable metal salts. The alkali metal or alkaline earth metal salt is obtained, for example, by dissolving the compound in an excess amount of an alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and evaporating and drying the filtrate. At this time, it is preferable for the metal salt to produce sodium, potassium or calcium salt. The corresponding silver salt is also obtained by reacting an alkali metal or alkaline earth metal salt with a suitable salt (such as silver nitrate).
또한, 본 발명은 엘라그산(ellagic acid) 및 디하이드로미리세틴(dihydromyricetin), 또는 이들의 약학적으로 허용가능한 염을 유효성분으로 함유하는 화장료 조성물을 제공한다.The present invention also provides a cosmetic composition comprising, as an active ingredient, ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof.
상기 조성물은 자외선 차단, 피부 광손상 개선, 피부노화 개선, 피부 재생, 항염증, 항산화, 피부주름 개선 및 피부탄력 개선용으로 이루어진 그룹으로부터 선택되는 1종 이상의 용도로 사용될 수 있다.The composition may be used in at least one kind selected from the group consisting of UV blocking, skin light damage improvement, skin aging improvement, skin regeneration, anti-inflammation, antioxidation, skin wrinkle improvement and skin elasticity improvement.
또한, 상기 조성물은 피부 주름, 홍반 또는 피부 짖물음을 개선하고, 피부의 재생, 피부의 염증을 예방, 개선 또는 치료하는 효과를 나타낸다. 또한, 상기 조성물은 노화, 보다 구체적으로 UV에 의한 노화, 산화 또는 염증을 억제할 수 있고, 보다 더 구체적으로 UVB에 의한 노화, 산화 또한 염증을 억제할 수 있다.In addition, the composition exhibits an effect of improving skin wrinkles, erythema or skin irritation, restoring skin, preventing, ameliorating or treating inflammation of skin. In addition, the composition can inhibit aging, more particularly UV aging, oxidation or inflammation, and more particularly, aging, oxidation and even inflammation by UVB.
따라서, 본 발명의 엘라그산(ellagic acid) 및 디하이드로미리세틴(dihydromyricetin), 또는 이들의 약학적으로 허용가능한 염은 자외선 차단, 피부노화 개선, 항염증, 항산화, 피부주름 개선 및 피부탄력 개선용 용도를 갖는 화장료 조성물로 유용하게 사용될 수 있다.
Therefore, the ellagic acid and dihydromyricetin of the present invention, or a pharmaceutically acceptable salt thereof, can be used for ultraviolet screening, skin aging, anti-inflammation, antioxidation, skin wrinkle improvement and skin elasticity improvement It can be usefully used as a cosmetic composition having a use.
본 발명에 따른 화장료 조성물은 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클렌징, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션, 스프레이 및 이들의 혼합물로 구성된 군으로부터 선택되는 제형을 가질 수 있다.The cosmetic composition according to the present invention may be in the form of a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant-containing cleansing, oil, powder foundation, emulsion foundation, wax foundation, ≪ / RTI >
본 발명에 따른 화장료 조성물은 당업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클렌징, 오일, 분말 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화 될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 본 발명의 조성물이 화장료 조성물로 사용될 때에는 화장수, 에멀젼, 크림, 에센스, 젤, 팩 및 클렌징크림으로부터 선택되는 기초 화장료; 화운데이션 등의 메이크업 화장료로 구성되는 군으로부터 선택되는 제형으로 제조될 수 있다.The cosmetic composition according to the present invention may be prepared into any of the formulations conventionally produced in the art, for example, a solution, a suspension, an emulsion, a paste, a gel, a cream, a lotion, a powder, a soap, But are not limited to, cleansing, oil, powder foundation, emulsion foundation, wax foundation, and spray. More particularly, when the composition of the present invention is used as a cosmetic composition, a cosmetic preparation is selected from cosmetic lotion, emulsion, cream, essence, gel, pack and cleansing cream; Makeup cosmetics such as foundation, and the like.
본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다.When the formulation of the present invention is a paste, cream or gel, an animal oil, vegetable oil, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component .
본 발명의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다.When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component. In the case of a spray, in particular, / Propane or dimethyl ether.
본 발명의 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.When the formulation of the present invention is a solution or an emulsion, a solvent, a dissolving agent or an emulsifying agent is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, , 3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan fatty acid esters.
본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소 결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.In the case where the formulation of the present invention is a suspension, a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.
본 발명의 제형이 계면활성제 함유 클렌징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올 에테르 설페이트, 설포숙신산 모노에스테르, 이세티오네이트, 이미다졸리늄 유도체, 메틸타우레이트, 사르코시네이트, 지방산 아미드 에테르 설페이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세리드, 지방산 디에탄올아미드, 식물성 유, 라놀린 유도체 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다.When the formulation of the present invention is a surfactant-containing cleansing, the carrier component may include aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide ether Alkylamido betaine, aliphatic alcohol, fatty acid glyceride, fatty acid diethanolamide, vegetable oil, lanolin derivative, or ethoxylated glycerol fatty acid ester.
또한 본 발명의 화장료 조성물은 각각의 제형에 상기 기재한 성분들 이외에 일반 피부 화장료에 배합되는 유분, 물, 계면활성제, 보습제, 저급알코올, 증점제, 킬레이트제, 색소, 방부제, 또는 향료 등을 필요에 따라 적절히 배합하여 사용할 수 있다.In addition, the cosmetic composition of the present invention may further contain, in addition to the components described above, oil, water, a surfactant, a moisturizer, a lower alcohol, a thickener, a chelating agent, a coloring agent, an antiseptic, And can be appropriately used in combination.
예컨대, 유연화장수는 본 발명에 따른 화합물 이외에 다가알콜류(프로필렌글리콜, 글리세린 등) 1～10 중량% 및 계면활성제(폴리에틸렌올레일에테르, 폴리옥시에틸렌 경화피마자유 등) 0.05～2 중량%를 함유하도록 제조할 수 있다. 또한, 영양화장수 및 영양크림은 본 발명에 따른 화합물 이외에 오일류(스쿠알란, 바셀린, 옥틸도데칸올 등) 5～20 중량% 및 왁스성분(세탄올, 스테아릴알콜, 밀납 등) 3～15 중량%를 함유하도록 제조할 수 있으며, 에센스는 본 발명에 따른 화합물 이외에 글리세린, 프로필렌글리콜 등의 다가알콜류 5～30 중량%를 함유하여 제조할 수 있다. 마사지 크림은 본 발명에 따른 화합물 이외에 유동파라핀, 바셀린, 이소노닐이소노나노에이트 등의 오일 30～70 중량%를 함유하여 제조되며, 팩은 본 발명에 따른 화합물 이외에 폴리비닐알콜 5～20 중량%를 함유하는 필 오프(peel off) 팩 또는 일반유화형 화장료에 본 발명에 따른 화합물 이외에 카올린, 탈크, 산화아연, 이산화티탄 등의 안료가 5～30 중량% 함유된 워시오프(wash off) 팩으로 제조할 수 있다.
For example, besides the compound according to the present invention, the number of softening times may be adjusted so that 1 to 10% by weight of polyhydric alcohols (propylene glycol, glycerin, etc.) and 0.05 to 2% by weight of a surfactant (polyethylene oleyl ether, polyoxyethylene hardened castor oil, etc.) Can be manufactured. The nutritional lotion and nutritional cream may contain 5 to 20% by weight of oils (squalane, petrolatum, octyldodecanol, etc.) and 3 to 15% by weight of wax components (cetanol, stearyl alcohol, And the essence may be prepared by adding 5 to 30% by weight of polyhydric alcohols such as glycerin, propylene glycol and the like in addition to the compound according to the present invention. In addition to the compound according to the present invention, the massage cream is prepared by containing 30 to 70% by weight of an oil such as liquid paraffin, petrolatum, isononylisononanoate, etc. The pack contains 5 to 20% by weight of polyvinyl alcohol, A wash off pack containing 5 to 30% by weight of a pigment such as kaolin, talc, zinc oxide or titanium dioxide in addition to the compound according to the present invention in a peel off pack or general emulsifiable cosmetic containing Can be manufactured.
이하, 본 발명을 실시예에 의해 상세히 설명한다.Hereinafter, the present invention will be described in detail by way of examples.
단, 하기 실시예는 본 발명의 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예 및 실험예에 한정되는 것은 아니다.
However, the following examples are merely illustrative of the present invention, and the present invention is not limited to the following examples and experimental examples.
<실시예 1> 엘라그산(ellagic acid; EGA) 또는 디하이드로미리세틴(dihydromyricetin; DHM)의 UVB 조사에 의한 세포사멸 억제 효과 확인Example 1 Confirmation of Cellular Death Suppression Effect of UVA Irradiation of ElaGic Acid (EGA) or Dihydromyricetin (DHM)
광노화에 대한 엘라그산, 디하이드로미리세틴 또는 이들의 병용처리 효과를 확인하기 위하여, UVB 조사에 의한 세포사멸 억제 효과를 확인하였다. In order to confirm the effects of treatment with agar agar, dihydroimisetin, or a combination thereof on photoaging, the effect of suppressing cell death by UVB irradiation was confirmed.
구체적으로, HACAT 세포를 96 웰 플레이트의 각 웰에 4 × 105 cell/well이 되도록 분주하고 37℃, 5% CO2 배양기에서 24시간 동안 배양한 후 DMEM 배지는 제거한 뒤 5% BSA(SIGMA, USA)가 첨가된 무혈청 저농도 포도당(free serum low glucose) DMEM(Gibco, USA)배지에 대조군으로 DMSO를 첨가하고, 실험군으로는 본 발명의 EGA 50 μM, DHM 50 μM 또는 EGA 25 μM + DHM 25 μM 농도로 각각 첨가하여 세포에 처리한 다음 10 시간 동안 37℃, 5% CO2 배양기에서 반응시켜 주었고 10시간이 지난 뒤 UVB를 각각 0 MED, 0.5 MED, 1 MED, 2 MED로 조사 후 12시간 동안 방치하였다. 12시간 후 배지는 제거한 뒤 MTT(3-(4,5-dimethylthiazol-2-yl-2,5-diphenyl tetrazolium bromide, SIGMA, USA) 용액(1 mg/ml)을 넣고 3시간 동안 37℃, 5% CO2 배양기에서 배양한 다음 각 웰에 들어있는 배지를 제거하고 DMSO(Dimethyl sulfoxide, SIGMA, USA) 100 μL를 넣어 녹을 수 있도록 10분간 방치 뒤 ELISA(VersaMaxTM, Molecular Devices)를 이용하여 490 nm에서 흡광도를 측정하였다. 이 흡광도는 MTT가 세포에 의해서 환원된 양을 나타내며, 따라서 각 웰에 존재하는 생존 수와 비례한다. 측정 시 공시료는 DMSO로 하였고, 세포의 생존율은 다음과 같이 계산하였다.Specifically, HACAT cells were plated at 4 × 10 5 cells / well in each well of a 96-well plate and cultured in a 5% CO 2 incubator at 37 ° C. for 24 hours. Then, DMEM medium was removed, and 5% BSA (SIGMA, DMSO was added as a control group to the free serum low glucose DMEM medium (Gibco, USA) supplemented with 50 μM of the present invention, 50 μM of DHM or 25 μM of EGA + DHM 25 μM. After 10 hours, the cells were treated with 0 MED, 0.5 MED, 1 MED and 2 MED, respectively. After 12 hours, the cells were incubated for 10 hours at 37 ° C in a 5% CO 2 incubator. Lt; / RTI > After 12 hours, the media was removed and MTT (3- (4,5-dimethylthiazol-2-yl-2,5-diphenyl tetrazolium bromide, SIGMA, USA) solution (1 mg / % CO 2 incubator. After removing the media from each well, 100 μL of DMSO (Dimethyl sulfoxide, SIGMA, USA) was added to the plate for 10 minutes to allow it to dissolve. Then, ELISA (VersaMax ™ , Molecular Devices) The absorbance was measured by the amount of the MTT reduced by the cells, and thus, was proportional to the number of viable cells present in each well. For the measurement, the blank was DMSO and the cell viability was calculated as follows .
그 결과, 도 1에 나타낸 바와 같이, 0 MED 시에는 실험군은 대조군과 비교하여 UVB 조사에 의한 세포사멸에 차이가 없었으나, 0.5 MED 부터 조사량이 증가할수록 EGA 50 μM 또는 DHM 50 μM 처리군에서 세포 사멸이 감소하였고, 특히 EGA 및 DHM를 병용처리한 EGA 25 μM + DHM 25 μM 처리군은 상승적으로(synergistic) 세포사멸을 억제하는 것을 확인하였다(도 1).As a result, as shown in FIG. 1, at 0 MED, there was no difference in UVB-induced apoptosis in the experimental group compared to the control group. However, as the dose was increased from 0.5 MED, 50 mg of EGA or 50 μM of DHM And that the treatment with EGA 25 μM + DHM 25 μM combined with EGA and DHM inhibited synergistic cell death (FIG. 1).
<< 실시예Example 2> 2> UVBUVB 조사에 의한 지질과산화물(lipid peroxide) 생성 억제효과 Inhibitory effect of lipid peroxide on lipid peroxide production by irradiation
자외선으로 인해 세포에서 생성되는 자유라디칼이 지질을 과산화시켜 과산화물을 생성하고, 이러한 과산화물은 세포막과 핵산의 손상을 일으켜 세포사멸을 나타내므로, 엘라그산, 디하이드로미리세틴의 UVB 조사에 의한 지질과산화물(lipid peroxide) 생성 억제효과를 확인하였다.Since ultraviolet light causes peroxidation of lipid peroxidation by free radicals generated in cells, these peroxides cause cell membrane and nucleic acid damage, leading to apoptosis. Therefore, lipid peroxide (UVA) lipid peroxide production inhibitory effect.
구체적으로, 상기 <실시예 1>과 동일하게 HACAT 세포를 배양한 후, EGA 50 μM, DHM 50 μM 또는 EGA 25 μM + DHM 25 μM 농도로 각각 세포에 처리한 다음, UVB를 1 MED로 조사 후 12시간 동안 방치하였다. 또한, TBARS 방법으로 과산화지질의 함량을 측정하기 위하여 세포 배양액을 제거한 후 PBS(pH 7.4)로 세포를 모아 세포 처리 후 오토클레이브(autoclave)한 마이크로 퓨즈 튜브(micro fuse tube)에 넣고 원심분리하고 상층액을 제거하고 세포에 0.38% TBA(2-Thiobarbituric acid, SIGMA, USA) + 15% TCA(Trichloroacetic acid, SAMCHUN) / 0.25N HCl를 1:1로 희석한 용액을 첨가한 후 100℃ 드라이 오븐(dry oven)에서 2시간 동안 반응시켜준 후 충분히 식힌 뒤 원심분리하여 상층액을 취해 ELISA를 이용하여 532 nm에서 흡광도를 측정하였다. 세포의 양에 따라 지질과산화물의 함량이 차이가 있으므로, 세포양을 측정하기 위해서 단백질 분석(Protein assay)을 이용하여 세포 양을 측정하여 보정해 주었으며 지질과산화물은 지질과산화물의 기준물질인 말론디알데히드(malondialdehyde, MDA)를 측정해 대조군에 대한 퍼센트(%)로 계산하였다. Specifically, HACAT cells were cultured in the same manner as in <Example 1>, treated with 50 μM of EGA, 50 μM of DHM or 25 μM of EGA + 25 μM of DHM, respectively, And allowed to stand for 12 hours. In order to measure the content of lipid peroxide by the TBARS method, the cell culture medium was removed, and the cells were collected with PBS (pH 7.4), and the cells were treated with autoclaved microfuse tubes, centrifuged, After the solution was removed, a solution of 0.38% TBA (2-Thiobarbituric acid, SIGMA, USA) + 15% TCA (Trichloroacetic acid, SAMCHUN) / 0.25N HCl diluted 1: 1 was added, dry oven for 2 hours. After cooling sufficiently, the supernatant was taken by centrifugation and absorbance was measured at 532 nm using ELISA. Since the amount of lipid peroxide varies depending on the amount of cells, the amount of the cell was measured and corrected using a protein assay to measure the amount of the cell. The lipid peroxide was used as a reference substance of malondialdehyde malondialdehyde, MDA) were measured and calculated as a percentage (%) of the control group.
그 결과, 도 2에 나타낸 바와 같이, EGA 50 μM 또는 DHM 50 μM 처리군은 효과적으로 자외선으로 인해 생성되는 과산화물의 함량을 감소시켜고, 특히 EGA 및 DHM를 병용처리한 EGA 25 μM + DHM 25 μM 처리군은 상승적으로 과산화물의 함량을 감소시키는 것을 확인하였다(도 2).
As a result, as shown in FIG. 2, 50 μM of EGA or 50 μM of DHM effectively reduced the content of peroxide generated by ultraviolet rays, and in particular, 25 μM of EGA + DHM combined with DHM The group synergistically reduced the content of peroxides (Fig. 2).
<< 실시예Example 3> 3> 광노화와With photoaging 관련된 유전자 발현에 대한 효과 확인 Identify the effect on gene expression
자외선 조사 후, 항산화 또는 항염증 등에 관여하는 유전자에 대한 엘라그산, 디하이드로미리세틴의 효과를 확인하였다.After irradiation with ultraviolet rays, the effect of erlagic acid and dihydrolymisetin on genes involved in antioxidant or antiinflammation was confirmed.
구체적으로, 상기 <실시예 1>과 동일하게 HACAT 세포를 배양한 후, EGA 50 μM, DHM 50 μM 또는 EGA 25 μM + DHM 25 μM 농도로 각각 세포에 처리한 다음, UVB를 1 MED로 조사 후 12시간 동안 방치하였다. 그런 다음, 멸균된 PBS (pH 7.4)로 접시를 2회 세척한 다음 PBS를 제거하고 트리졸 시약(TRIzol reagent, Life Technologies, Rockville, MD, USA)으로 전체 RNA를 추출하였다. RNA는 람다 850 분광광도계(Perkin Elmer, Waltham, MA, USA)로 정량하였고, cDNA는 추출된 1 μg의 RNA로부터 합성되었다. 역전사효소 키트를 사용하여 각 cDNA를 제조하여 실시간 PCR에 사용하였다. 특정 유전자에 대한 동량의 cDNA 및 프라이머를 SYBR 그린믹스(Bio-Rad, Richmond, CA)와 혼합하고 실시간 PCR 기구를 사용하여 증폭시켰다. 열 사이클 조건은 55℃에서 2분, 95℃에서 10분, 94℃에서 20초, 65℃에서 30초, 22℃에서 20초로 40 사이클 하였다. 염증과 관련된 유전자 측정을 위하여 유도성 NO합성효소 iNOS, 종양괴사 인자 TNF-α, 콜라겐분해효소 MPP-1, Cu/Zn SOD, TGF-β, 타입 I 콜라겐(collagen-I)을 검지하기 위한 프라이머들이 사용하여 유전자 발현 변화를 확인하였다.Specifically, HACAT cells were cultured in the same manner as in <Example 1>, treated with 50 μM of EGA, 50 μM of DHM or 25 μM of EGA + 25 μM of DHM, respectively, And allowed to stand for 12 hours. Then, the plate was washed twice with sterilized PBS (pH 7.4), then PBS was removed, and total RNA was extracted with TRIZOL reagent (Life Technologies, Rockville, MD, USA). RNA was quantified on a Lambda 850 spectrophotometer (Perkin Elmer, Waltham, Mass., USA) and the cDNA was synthesized from 1 μg of extracted RNA. Each cDNA was prepared using reverse transcriptase kit and used for real-time PCR. Equal amounts of cDNA and primers for specific genes were mixed with SYBR Greenmix (Bio-Rad, Richmond, Calif.) And amplified using a real-time PCR instrument. The heat cycle conditions were 40 cycles of 2 minutes at 55 占 폚, 10 minutes at 95 占 폚, 20 seconds at 94 占 폚, 30 seconds at 65 占 폚, and 20 seconds at 22 占 폚. A primer for detecting inducible NO synthase iNOS, tumor necrosis factor TNF-α, collagenase MPP-1, Cu / Zn SOD, TGF-β and type I collagen- Were used to confirm gene expression changes.
그 결과, 도 3에 나타낸 바와 같이 collagen-1의 발현은 EGA 또는 DHM에 의해서 효과적으로 증가하였고, 특히 EGA 및 DHM를 병용처리할 경우, collagen-1의 발현을 현저하게 증가시켜, 피부세포를 유의적으로 재생시키는 것을 확인하였다. 또한, EGA는 MMP1을 유의적으로 감소시키지 않았지만, EGA 및 DHM의 병용처리는 MMP1을 유의적으로 감소시켜, 피부 재생에 유의적인 효과를 나타냄을 확인하였다(도 3). 따라서, EGA 및 DHM의 병용처리는 콜라겐의 합성을 증가시켜, 피부 재생에 유의적인 효과를 나타냄을 확인하였다.As a result, as shown in FIG. 3, the expression of collagen-1 was effectively increased by EGA or DHM. Particularly, when EGA and DHM were used in combination, the expression of collagen-1 was markedly increased, . In addition, although EGA did not significantly decrease MMP1, it was confirmed that the combination treatment of EGA and DHM significantly decreased MMP1 and showed a significant effect on skin regeneration (FIG. 3). Therefore, it was confirmed that the combination treatment of EGA and DHM increased the synthesis of collagen and showed a significant effect on skin regeneration.
또한, 도 4에 나타낸 바와 같이, 자외선으로 생성된 자유라디칼을 제거하는 효소인 SOD의 발현은 EGA 또는 DHM에 의해서 효과적으로 증가하였고, 특히 EGA 및 DHM를 병용처리할 경우, SOD의 발현을 현저하게 증가시키는 것을 확인하였다. 또한, 염증 반응과 관련된 TNF-α의 발현은 EGA 또는 DHM에 의해서 효과적으로 감소하였고, 특히 EGA 및 DHM를 병용처리할 경우, TNF-α의 발현을 현저하게 감소되는 것을 확인하였다(도 4).
In addition, as shown in FIG. 4, the expression of SOD, an enzyme that eliminates free radicals generated by ultraviolet rays, was effectively increased by EGA or DHM. Especially, when EGA and DHM were used in combination, the expression of SOD was remarkably increased . In addition, the expression of TNF-a in association with the inflammatory reaction was effectively reduced by EGA or DHM, and the expression of TNF-a was remarkably reduced when EGA and DHM were used in combination (FIG. 4).
<< 실시예Example 4> 4> 광노화가Photo-aging 유도된 동물모델에서 In an induced animal model EGAEGA 또는 or DHMDHM 의 효과 확인Check the effect of
ICR 마우스(대한바이오링크)를 분양받아, 1주일간 일반식이로 적응시킨 후, 각 그룹당 6마리씩 총 5그룹으로 나누고, 3 주 동안 0.7% dextrin(대조군), 0.7% EGA, 0.7% DHM, 또는 0.35% EGA + 0.35% DHM (EGA+DHM)가 각각 첨가된 43% 고지방식이를 마우스에 공급한 후, UV-B를 1 MED 조사하였다.The mice were divided into 5 groups of 6 mice per group and were given 0.7% dextrin (control), 0.7% EGA, 0.7% DHM, or 0.35 The mice were fed a 43% high-fat diet supplemented with% EGA + 0.35% DHM (EGA + DHM), followed by 1 MED of UV-B.
한편, 도 6과 같이 UV-B를 조사하기 전, 도 5에 개시된 바와 같이, 대조군은 본 발명의 폴리페놀을 용해시킨 용매인 1,3-butylene glycol를 사용하였고, EGA군의 3% EGA 용액을 150 uL, DHM군은 3% DHM 용액을 150 uL, EGA+DHM군은 3% EGA 용액과 3% DHM 용액을 75uL씩 혼합하여 마우스에 도포하였다. UV-B를 조사는 UV-B(VL: 115 C, 30 W; Vilber Lourmat, Marne Lavalee, France) 램프를 a radiometer/photometer에 장착하고 UV-B를 피부에서 약 30cm 떨어진 곳에서 36.5 uW로 30 분 동안 상기 등의 털을 제모한 ICR mice의 등에 1 MED (1MED = 36.5uW/30min/cm2) 조사하여 광노화를 유발시켰으며, UV-B 조사 후, 매일 실험군을 마우스에 도포하였다(도 5 및 도 6).
As shown in FIG. 5, prior to irradiation with UV-B as shown in FIG. 6, 1,3-butylene glycol, a solvent in which the polyphenol was dissolved in the present invention, was used as a control, and 3% EGA solution , 150 uL of 3% DHM solution in DHM group, and 75 uL of 3% EGA solution and 3% DHM solution in EGA + DHM group. The UV-B was irradiated with UV-B (VL: 115 C, 30 W; Vilber Lourmat, Marne Lavalee, France) on a radiometer / photometer and irradiated with UV- 1 MED (1MED = 36.5 uW / 30 min / cm 2 ) was irradiated to ICR mice exposed to the hair of the dorsal hair for a minute, and the mice were applied daily to the mice after UV-B irradiation And FIG. 6).
<4-1> UV 조사 후, 등에 피부 변화 확인<4-1> Confirmation of skin changes after UV irradiation
상기 <실시예 4>의 각 군의 마우스에 대하여 UV 노출 후, 각 군들 사이에 등의 피부 변화를 육안으로 관찰하였다.After the mice were exposed to UV for each group of Example 4, skin changes of the back were visually observed.
그 결과, 도 7에 나타낸 바와 같이, UV 노출 후 0시간에는 군들 사이에 큰 차이가 없었으나, 대조군에서는 피부의 주름이 증가하고 수분이 적어지는 것을 볼 수 있었다. 또한, 시간이 지나면서 대조군은 점차 홍반도 나타나고 짖물음, 화상 등이 심해진 반면, EGA군과 DHM군은 대조군에 비해서 홍반과 화상이 가장 적었고 짖물음도 쉽게 없어지는 것을 볼 수 있었고, 특히 EGA+DHM이 가장 효과적으로 홍반, 짖물음, 화상이 없어지고 정상 상태로 회복되는 것을 확인하였다(도 7).
As a result, as shown in Fig. 7, there was no significant difference between the groups at 0 hour after UV exposure, but in the control group, the wrinkles of the skin increased and the moisture decreased. In addition, EGA and DHM groups had less erythema and burning than the control group, and they were more likely to lose barking, and EGA + DHM was found to be most effective in eliminating erythema, barking, burning, and recovering to a normal state (Fig. 7).
<4-2> UV 조사 후, 홍반의 변화 확인<4-2> Confirmation of change of erythema after UV irradiation
상기 <실시예 4>의 각 군의 마우스에 대하여 UV 노출 후, 각 군들 사이에 홍반의 변화를 확인하였다.After the mice were exposed to UV for each group of Example 4, the change of erythema was observed among the groups.
홍반 변화는 하기와 같이 점수로 변환하여 측정하였다:Erythema changes were measured and converted into scores as follows:
홍반이 전혀 없음: 0No erythema at all: 0
아주 가벼운 홍반(육안으로 식별할 정도): 1Very mild erythema (visible to the naked eye): 1
분명한 홍반: 2Clear erythema: 2
약간 심한 홍반: 3Some severe erythema: 3
심한 홍반(홍당무색 발적)과 가벼운 정도의 피부가 까지는 것: 4Severe erythema (reddish blotchy) and mild degree of skin up to: 4
그 결과, 도 8에 나타낸 바와 같이, EGA군, DHM군 및 EGA+DHM군 모두 대조군과 비교하여 홍반 증가를 감소시키고, 발생한 홍반도 유의적으로 회복시키므로, 자외선 차단 효과를 나타냄을 확인하였고, 특히 EGA+DHM군은 현저한 상승적 효과를 나타냄을 확인하였다(도 8).As a result, as shown in FIG. 8, the EGA group, the DHM group, and the EGA + DHM group both showed reduced erythema increase and significantly recovered erythema as compared with the control group, EGA + DHM group showed a remarkable synergistic effect (Fig. 8).
<4-3> UV 조사 후, 화상 정도의 변화 확인<4-3> After the UV irradiation, confirm the change in the image quality
상기 <실시예 4>의 각 군의 마우스에 대하여 UV 노출 후, 각 군들 사이에 화상 정도의 변화를 확인하였다.After UV exposure of the mice of each group of Example 4, changes in the degree of burning were observed among the groups.
화상 정도는 하기와 같이 점수로 변환하여 측정하였다:The degree of image was converted into scores as follows and measured:
화상이 전혀 없음: 0No image at all: 0
아주 가벼운 화상(육안으로 식별할 정도): 1Very light burns (visible to the naked eye): 1
분명한 화상: 2Clear image: 2
약간 심한 화상: 3Slightly severe burns: 3
심한 화상: 4Severe burns: 4
그 결과, 도 9에 나타낸 바와 같이, EGA군은 자외선 노출 후 화상이 나타났으나 대조군보다는 현저히 낮았고 그 후에는 더 이상 화상이 진행되지 않고, 회복되어서 자외선을 차단하는 효과를 나타냄을 확인하였다. 또한, DHM 군은 첫 번째 자외선 노출 후에는 홍반이 낮았던 것처럼 화상 정도도 다른 군들에 비해 현저하게 낮았으며, EGA+DHM군은 화상 정도 감소에 있어서도 유의적인 상승적 효과를 나타내는 것을 확인하였다(도 9).
As a result, as shown in FIG. 9, it was confirmed that the EGA group showed an image after exposure to ultraviolet light but was significantly lower than that of the control group. In addition, the degree of burning was significantly lower in the DHM group than in the other groups as the erythema was lower after the first UV exposure, and the EGA + DHM group showed a significant synergistic effect in the reduction of the burning degree (FIG. 9) .
<4-4> UV 조사 후, ≪ 4-4 > After UV irradiation, 짖물림Bark 정도의 변화 확인 Confirm change of degree
상기 <실시예 4>의 각 군의 마우스에 대하여 UV 노출 후, 각 군들 사이에 짖물림 정도의 변화를 확인하였다.After UV exposure of the mice of each group of Example 4, changes in the degree of barking between the groups were observed.
짖물림 정도는 하기와 같이 점수로 변환하여 측정하였다:The degree of barking was measured and converted into scores as follows:
짖물림이 전혀 없음: 0No barking at all: 0
아주 가벼운 짖물림(육안으로 식별할 정도): 1Very light barking (visible to the naked eye): 1
분명한 짖물림: 2Clear barking: 2
약간 심한 짖물림: 3Slightly severe barking: 3
심한 짖물림: 4Severe barking: 4
그 결과, 도 10에 나타낸 바와 같이, 짖물음은 모든 군에서 자외선 조사 2일부터 생기기 시작해서 2일째에 가장 많았으며 5일에 최고조에 도달하였고, 그 후 감소하는 경향을 나타냈으나, EGA+DHM 처리군은 대조군과 비교하여 짖물림 정도가 유의적으로 감소된 것을 확인하였다(도 10).
As a result, as shown in Fig. 10, the barking occurred at 2 days after ultraviolet irradiation in all groups, reached the peak at 5 days and then decreased, but EGA + DHM-treated group was significantly reduced in the degree of barking compared to the control group (FIG. 10).
<4-5> UV 조사 후, 상처 정도의 변화 확인 <4-5> After the UV irradiation, confirm the change in the extent of the wound
상기 <실시예 4>의 각 군의 마우스에 대하여 UV 노출 후, 각 군들 사이에 상처 정도의 변화를 확인하였다.After UV exposure, mice of each group of Example 4 were examined for changes in the degree of scarring among the groups.
상처 정도는 하기와 같이 점수로 변환하여 측정하였다:The degree of wound was converted to score as follows:
상처가 전혀 없음: 0No wounds at all: 0
아주 가벼운 상처(육안으로 식별할 정도): 1Very light wound (visible to the naked eye): 1
분명한 상처: 2Clear wounds: 2
약간 심한 상처: 3Some serious injuries: 3
심한 상처: 4Severe wound: 4
그 결과 도 11에 나타낸 바와 같이, UV 노출에 따라 손상된 상처가 EGA군, DHM군 및 EGA+DHM군 모두 대조군과 비교하여 감소되는 것을 확인하였고, 특히 EGA+DHM 처리군 현저한 상처 정도 감소 효과를 나타냄을 확인하였다(도 11).
As a result, as shown in Fig. 11, it was confirmed that the wound damaged by UV exposure was reduced in the EGA group, the DHM group, and the EGA + DHM group as compared with the control group, and the EGA + (Fig. 11).
<4-6> 등 조직의 조직학적 변화 확인<4-6> Identification of Histopathological Changes in Tissue
UV 노출 후 각 그룹의 등 조직을 분리한 후, 헤마톡실린 및 에오신(H-E) 염색 및 톨루이딘블루(toluidine blue)을 수행한 후, 각 실험군 마우스 등 조직의 조직학적 변화를 확인하였다.After UV exposure, the dorsal tissues of each group were separated, followed by hematoxylin and eosin (H-E) staining and toluidine blue, and histological changes of tissues such as mice in each experimental group were confirmed.
그 결과, 도 12에 나타낸 바와 같이 UV 조사는 세포의 크기가 커지고 세포의 배열이 엉성해지며 부종을 증가시켰으며, 피부의 표피 부분이 거칠어지고, 진피도 많은 변형을 나타냄을 확인하였다(도 12). 또한, 도 12 내지 도 14에 나타낸 바와 같이 염증세포의 mast cell의 수는 대조군에서 가장 많이 증가했으며 EGA군과 DHM군에서 모두 감소하였지만, 특히 EGA+DHM군에서 상승적으로 감소하는 것을 확인하였다(도 12 내지 도 14).
As a result, as shown in Fig. 12, it was confirmed that the UV irradiation increased the size of the cells, the arrangement of the cells became coarse, the edema increased, the skin part of the skin became rough, and the dermis showed many deformation (Fig. 12) . In addition, as shown in Figs. 12 to 14, the number of mast cells of the inflammatory cells was the highest in the control group and decreased in both the EGA group and the DHM group, but it was found to decrease in the EGA + DHM group 12 to 14).
<4-7> 등 조직의 사이토카인 발현 변화 확인<4-7> Identification of cytokine expression changes in tissues
UV 노출 후 각 그룹의 등 조직을 분리한 후 염증을 일으키는 사이토카인인 TNF-a와 IL-1b의 mRNA 발현을 상기 <실시예 3>과 동일한 방법으로 확인하였다.After UV exposure, mRNA expression of TNF-a and IL-1b, which are cytokines that cause inflammation after isolating each group of isoforms, was confirmed in the same manner as in Example 3 above.
그 결과, 도 15에 나타낸 바와 같이 염증성 사이토카인은 정상대조군에 비해 대조군에서 현저히 증가하였고, 이러한 증가는 EGA군과 DHM군을 처리하였을 때 감소하였는데, 특히 EGA+DHM군에서 현저하게 감소되는 것을 확인하였다(도 15).
As a result, as shown in Fig. 15, the inflammatory cytokine was significantly increased in the control group as compared with the normal control group, and this increase was decreased when the EGA group and the DHM group were treated, (Fig. 15).
Claims (11)
A disease selected from the group consisting of skin wrinkles, erythema, skin scars and skin wounds containing ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof as an active ingredient, Preventive and therapeutic topical skin.
A dermatological external preparation for skin phototherapy improvement or skin regeneration comprising, as an active ingredient, ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof.
An antiinflammatory skin external preparation containing, as an active ingredient, ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof.
An external preparation for skin for inhibiting photoaging, oxidation or inflammation by UV, which comprises, as an active ingredient, ellagic acid and dihydromyricetin, or a pharmaceutically acceptable salt thereof.
The present invention relates to a cosmetic composition which comprises an effective ingredient of ellagic acid and dihydromyricetin or a pharmaceutically acceptable salt thereof as an active ingredient for protecting against UV rays, improving skin photodamage, improving skin aging, regenerating skin, Improving skin wrinkles and improving skin elasticity. The cosmetic composition according to any one of claims 1 to 3,
6. The cosmetic composition according to claim 5, wherein the composition improves skin erythema or skin rash.
6. The cosmetic composition according to claim 5, wherein the composition inhibits aging, oxidation or inflammation caused by UV.
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| KR1020170009488A KR101943302B1 (en) | 2017-01-20 | 2017-01-20 | Skin external application composition and cosmetic composition comprising ellagic acid and dihydromyricetin |
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| KR1020170009488A KR101943302B1 (en) | 2017-01-20 | 2017-01-20 | Skin external application composition and cosmetic composition comprising ellagic acid and dihydromyricetin |
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| KR20180085880A KR20180085880A (en) | 2018-07-30 |
| KR101943302B1 true KR101943302B1 (en) | 2019-01-29 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200140106A (en) | 2019-06-05 | 2020-12-15 | (주)에스앤피인터내셔널 | Method for extractiong of ellagic acid from berry |
| KR20220135000A (en) | 2021-03-29 | 2022-10-06 | 농업회사법인제주생물자원㈜ | Anti-oxidant composition comprising the extract of rubus hongnoensis nakai as an effective component |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101451989B1 (en) * | 2008-10-13 | 2014-10-21 | 주식회사 엘지생활건강 | Cosmetic compostion for skin cell regeneration |
| KR101068763B1 (en) * | 2009-02-05 | 2011-09-28 | 한림대학교 산학협력단 | UV-induced skin aging inhibiting composition comprising ellagic acid |
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- 2017-01-20 KR KR1020170009488A patent/KR101943302B1/en active IP Right Grant
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200140106A (en) | 2019-06-05 | 2020-12-15 | (주)에스앤피인터내셔널 | Method for extractiong of ellagic acid from berry |
| KR20220135000A (en) | 2021-03-29 | 2022-10-06 | 농업회사법인제주생물자원㈜ | Anti-oxidant composition comprising the extract of rubus hongnoensis nakai as an effective component |
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| Publication number | Publication date |
|---|---|
| KR20180085880A (en) | 2018-07-30 |
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