KR101717020B1 - The composition comprising saponins derived from green tea seed having antifungal and anticancer activity and manufacturing method thereof - Google Patents
The composition comprising saponins derived from green tea seed having antifungal and anticancer activity and manufacturing method thereof Download PDFInfo
- Publication number
- KR101717020B1 KR101717020B1 KR1020160056518A KR20160056518A KR101717020B1 KR 101717020 B1 KR101717020 B1 KR 101717020B1 KR 1020160056518 A KR1020160056518 A KR 1020160056518A KR 20160056518 A KR20160056518 A KR 20160056518A KR 101717020 B1 KR101717020 B1 KR 101717020B1
- Authority
- KR
- South Korea
- Prior art keywords
- green tea
- tea seed
- ethanol
- extract
- seeds
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 32
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- 229940121375 antifungal agent Drugs 0.000 title claims abstract description 21
- 229930182490 saponin Natural products 0.000 title claims description 36
- 235000017709 saponins Nutrition 0.000 title claims description 36
- 150000007949 saponins Chemical class 0.000 title claims description 35
- 238000004519 manufacturing process Methods 0.000 title description 8
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Abstract
Description
본 발명은 녹차씨 추출물로부터 유래된 항진균 및 항암 활성을 갖는 사포닌류에 대한 것으로서 항진균 활성과 항암 활성이 우수하다.The present invention relates to antifungal agents derived from green tea seed extract and saponins having anticancer activity, and has excellent antifungal activity and anticancer activity.
식품, 생활용품, 의약품 및 화장품 등은 생산, 유통, 저장 단계에서 다양한 미생물에 의한 생물학적 부패, 변질이 수반되며, 이러한 부패 및 변질은 제품의 품질 악화는 물론 제품 생산 자체를 불가능하게 하기도 한다. 실제 농산물의 경우 부패 변질에 의한 손실은 전체 산업의 약 40%를 상회하며, 따라서 효율적인 부패, 변질의 방지는 특정 제품의 생산성을 2배 정도 증가시키는 효과를 나타낸다. 따라서, 미생물에 의한 부패를 막아주고 제품을 오랫동안 유지하기 위해서 제조 공정에서 미생물을 제거하거나 보존료(preservative)를 사용한 미생물제어가 필수적이다.Food, household goods, medicines and cosmetics are accompanied by biological corruption and deterioration by various microorganisms in production, distribution and storage stages. Such corruption and deterioration may deteriorate product quality and make production itself impossible. In the case of actual agricultural products, the loss due to corruption is more than 40% of the total industry, and therefore, effective prevention of corruption and alteration has the effect of doubling the productivity of a specific product. Therefore, in order to prevent microbial decay and maintain the product for a long time, microbial control using microbial removal or preservative is essential in the manufacturing process.
식품 변패 미생물 중에서도 효모류를 포함한 곰팡이는 식품 전반에 걸쳐서 오염되어 제품의 품질을 저하시키며 증식 억제가 어려운 동시에 다른 미생물에 비해서 특히 천연 보존료로 제어하기가 힘든 미생물로서 막대한 경제적인 손실을 입힌다. 식품 변패를 유발하는 효모류로는 간장 산막효모(Zygosaccharomyces rouxii), 간장 팽창 효모(Candida versatilis), 소스류 및 식초 음료의 내산성 효모(Zygosaccharomyces sp.), 떡 변패 효모(Pichia anomala, Candida boildinii), 야채 음료 유래 효모 등이 있으며, 이 효모들은 주로 가스 발생으로 식품 포장 용기를 팽창 및 파손시킨다. 따라서 식품 제조시에 효모 증식 억제는 매우 중요한 식품 관리 포인트에 해당한다.Among food microorganisms, fungi including yeast are contaminated throughout the food to deteriorate the quality of the product, and it is difficult to inhibit the growth of microorganisms, and it is a microorganism which is difficult to control with other natural microorganisms. Yeasts that cause food deterioration include soy safflower yeast ( Zygosaccharomyces rouxii ), yeast expansion yeast ( Candida versatilis , Zygosaccharomyces sp. of sauces and vinegar drinks, Pichia anomala , Candida boildinii , and vegetable beverage-derived yeast. These yeasts mainly expand and break food packaging containers due to gas generation. Therefore, inhibition of yeast growth during food production is a very important food management point.
식품에서 효모류는 솔빈산, 안식향산, 파라옥시안식향산에틸(POBE), 파라옥시안식향산메틸과 같은 합성방부제를 사용하거나, 비타민B1라우릴황산염(영양강화제)과 같은 합성 식품첨가물, 주정, 유카추출물, 겨자정유와 같은 천연소재를 사용하여 제어한다. 하지만 주정, 겨자 정유 및 유카추출물은 소재 특성상 제한적으로 사용되며, 합성방부제가 첨가된 식품을 소비자들이 기피하는 경향이 있으므로 다양한 식품에 적용이 용이한 천연 항진균제제의 개발이 필요하다.Yeasts in foods are produced by using synthetic preservatives such as sorbic acid, benzoic acid, p-hydroxybenzoic acid (POBE), and p-hydroxybenzoic acid, or synthetic food additives such as vitamin B1 lauryl sulfate (nutritional enhancer), alcohol, Control using natural materials such as oil. However, it is necessary to develop a natural antifungal agent which is easy to apply to diverse foods because of the limited use of alcoholic beverages, mustard essential oil and yucca extract, and consumers tend to avoid synthetic preservative added food.
녹차(Camellia sinensis)는 Camellia 속에 속하는 Theaceae(차나무)과의 종자식물로서, 세계적으로 30개국 이상에서 재배되고 있으며, 물 다음으로 많이 소비되는 음료이다(Haixia et al., Journal of food science, 74, 6, 2009). 음료는 잎을 건조시켜 우려내어 마시며, 잎을 발효시킨 정도에 따라서 주로 3가지 종류 즉, 홍차, 녹차 또는 우롱차의 형태로 소비되고 있다. 홍차는 완전 발효시킨 것이고, 우롱차는 부분적으로 발효시켰으며, 녹차는 발효되지 않은 것으로 홍차나 우롱차보다 더 많은 카테킨을 포함한다(Alastair, AU Journal of Technology, 12, 4, 251-265, 2009). 차는 거의 4,000여개의 생리활성 물질을 포함하고 있다. 그 중 1/3이 폴리페놀이며, 그 밖에도 휘발성 오일, 카페인, vitamin C, tannin, saponin과 같은 생리활성에 도움을 주는 2차 대사산물들을 포함하고 있다. 녹차의 주요 폴리페놀은 카테킨으로 카테킨은 (-)-epicatechin gallate (ECG), (-)-epicatechin (EC), (-)-epigallocatechin (EGC), 그리고 (-)-epigallocatechin gallate (EGCG)이다. 녹차에서 발견되는 카테킨 중 가장 풍부한 것은 epigallocatechin gallate (EGCG)이다(Parmar et al., Global Journal of Pharmacology, 6, 2, 52-59, 2012). 이런 폴리페놀 성분들은 여러 가지 건강에 기여하는 생리활성물질로서 녹차의 체중감소 촉진, 항산화 효과, 심혈관 질병 예방, 항염증 효과, 스트레스 감소, 피부보호 같은 효과를 가진다(Raymond et al., The Journal of Alternative and Complementary Medicine, 11, 3, 521-528, 2005). 건강에 대한 인식이 높아지면서 녹차의 생산량도 증가될 것으로 예상되고 있다. Camellia sinensis is a seed plant with theaceae belonging to the genus Camellia , grown in more than 30 countries worldwide, and is the next most consumed beverage (Haixia et al. , Journal of food science , 74, 6, 2009). The beverage is dried by frying the leaves, and is consumed in three forms, namely tea, green tea or oolong tea depending on the degree of leaf fermentation. Tea is completely fermented, oolong tea is partially fermented, and green tea contains more catechins than non-fermented tea or oolong tea (Alastair, AU Journal of Technology , 12, 4, 251-265, 2009) . The tea contains almost 4,000 physiologically active substances. One third of them are polyphenols, and they also contain secondary metabolites that help physiological activities such as volatile oils, caffeine, vitamin C, tannin, and saponin. The major polyphenols of green tea are catechins and catechins are (-) - epicatechin gallate (ECG), (-) - epicatechin (EC), (-) - epigallocatechin (EGC) and (-) - epigallocatechin gallate (EGCG). The most abundant catechins found in green tea are epigallocatechin gallate (EGCG) (Parmar et al. , Global Journal of Pharmacology , 6, 2, 52-59, 2012). These polyphenols are physiologically active substances contributing to various health effects such as promotion of weight loss, antioxidative effect, prevention of cardiovascular diseases, anti-inflammatory effect, stress reduction, skin protection, etc. (Raymond et al. , The Journal of Alternative and Complementary Medicine , 11, 3, 521-528, 2005). It is expected that the production of green tea will increase as the awareness of health increases.
이와 같은 높은 유용성으로 녹차의 소비량이 계속적으로 증가하고 있으므로 녹차씨의 생산량도 증가하고 있으나, 녹차씨 오일 사용 외에는 이용이 없으므로 녹차 수확이 끝난 후 녹차씨는 거의 폐기되고 있는 실정이다. 하지만, 최근에는 녹차씨로부터 유효한 생리활성 성분을 분리하여 부가가치를 높일 수 있는 연구들이 진행되고 있다.As the consumption of green tea is continuously increased due to such high availability, the production amount of green tea is increasing, but since there is no use other than the use of green tea seed oil, green tea seeds are almost discarded after the green tea harvest is completed. However, in recent years, studies have been made to increase the added value by separating effective physiologically active ingredients from green tea seeds.
녹차씨는 속씨를 감싸고 있는 겉껍질상태로 열리는데 이 속에는 2~4개의 속씨가 들어있다. 녹차씨에는 단백질 함량이 잇꽃종실이나 해바라기씨의 함량과 거의 비슷하며, 조지방의 경우 잇꽃종실과 유사한 수준으로써 식물유지 자원으로 활용할 수 있는 가능성이 많다. 녹차씨가 함유하고 있는 지방산은 oleic acid가 가장 많으며, 또한 조사포닌은 콩보다 3배 더 많이 함유하고 있어 계면활성제나 항종양제 등으로 사용 가능할 것으로 기대되는 농산 부산물이다(Na HH et al., Journal Korean Agric. Chem . Soc ., 35, 4, 272-275, 1992). 특히 녹차씨 사포닌은 녹차씨 건조물의 10% 이상을 차지하는데 항거담제, 항염증(Yuji et al., Japan Agricultural Research Quarterly, 35, 3, 185-188, 2001), 위장보호(Toshio et al., Journal of Natural Products, 69, 2, 185-190, 2006) 등의 기능들이 연구되었다. The green tea is wrapped in a bark wrapped around the seeds, which contains two to four seeds. The protein content of green tea seeds is similar to that of safflower seeds and sunflower seeds, and crude fat is likely to be used as a plant maintenance resource at a level similar to that of safflower seeds. Green tea contains most of the fatty acids, oleic acid, and crude saponin, which is three times more abundant than soybean, which is expected to be used as a surfactant or antitumor agent (Na HH et al. Journal of Agric. Chem . Soc . , 35, 4, 272-275, 1992). In particular, green tea saponin accounts for more than 10% of the green tea seeds, and has been shown to be an antiseptic, anti-inflammatory (Yuji et al. , Japan Agricultural Research Quarterly , 35, 3, 185-188, 2001), gastrointestinal protection (Toshio et al. Journal of Natural Products , 69, 2, 185-190, 2006).
녹차의 잎에 관한 많은 연구가 진행된 반면에 녹차씨에 관한 선행연구로는 '발아 녹차씨 추출물을 함유하는 피부 외용제 조성물'(국내 특허제2012-0037794호), '녹차씨 껍질 추출물을 유효성분으로 함유하는 항산화 또는 항염 활성을 갖는 화장료 조성물'(국내 특허제2010-0032134), '녹차오일을 함유한 모발 및 두피상태 개선용 조성물'(국내 특허제2005-0044901호), '피부 탄력 증진 효과를 갖는 녹차씨 오일을 함유하는 화장료 조성물'(국내 특허제2006-0025340호), '항산화, 항염 및 항동맥경화 활성을 갖는 녹차씨 추출물을 함유하는 약학 조성물'(국내 특허제2006-003737호) 등 녹차씨유, 녹차씨 껍질 및 항염, 항산화 활성에 대한 특허가 보고되었다. Although a lot of studies on green tea leaves have been carried out, prior studies on green tea seeds have shown that the composition for external application for skin containing ginger green tea seed extract (Korean Patent No. 2012-0037794), green tea seed extract as an active ingredient (Korean Patent No. 2010-0032134), 'Composition for improving hair and scalp condition containing green tea oil' (Korean Patent No. 2005-0044901), 'Effect of improving skin elasticity' (Korean Patent No. 2006-0025340), 'Pharmaceutical composition containing green tea seed extract having antioxidant, anti-inflammatory and anti-arteriosclerotic activity' (Korean Patent No. 2006-003737), etc. Green tea seed oil, green tea seed husk, and anti-inflammatory and antioxidant activity.
녹차씨 유래 물질들에 대해서도 다양한 효능들이 보고가 되어 있으며, 그에 따라 saponin, flavonoid, vitamin, polyphenol 과 오일과 같은 많은 생리활성 물질들도 보고가 되어 있다. 녹차씨의 polyphenol 중 cathechin류인 epigallocathechin-3 gallate (EGCG), epigallocathechin (EGC)과 epicathechin-3 gallate (ECG) 등은 항산화 효과와 항암 효과가 있는 것으로 보고되어 있다(Natl Cancer Inst. 85, 1038-1049, 1993). 녹차씨 flavonoid 물질 중 kaempferol과 nicotiflorin은 tyrosinase 억제 효과와 melanin 합성 저해 효과가 있는 것으로 밝혀져 있다(Bull. Korean Chem. Soc. 34(7), 2199~2202, 2013). 또한, camelliaside A와 B 또한 항암 효과가 있는 것으로 알려져 있다. 녹차씨의 saponin중 assamsaponin은 위장배출 활성이 있으며 (Chem. Pharm. Bull., 48, 1720-1725, 2000), sasanquasaponin은 항암활성이 있으며(Fitoterapia, 84, 123-129, 2013), floratheasaponin은 항고지혈증 효과가 있고 (J. Nat. Prod., 68, 1360-1365, 2005), theasaponin은 위 점막 보호 효과가 보고되어 있다(J. Nat. Prod., 69, 185-190, 2006).There have also been reports of various efficacies on green tea seeds, and many other physiologically active substances such as saponins, flavonoids, vitamins, polyphenols and oils have also been reported. Epidermal growth factor (EGC), epigallocathechin (EGC) and epicathechin-3 gallate (ECG) have been reported to have antioxidant and anticancer effects among the polyphenols of green tea seeds (Natl Cancer Inst. 85, 1038-1049 , 1993). Kaempferol and nicotiflorin among flavonoids of green tea have been shown to inhibit tyrosinase and melanin synthesis (Bull. Korean Chem. Soc. 34 (7), 2199 ~ 2202, 2013). Camelliaside A and B are also known to have anticancer effects. In the case of green tea saponins, assamsaponin has gastrointestinal activity (Chem. Pharm. Bull., 48, 1720-1725, 2000), sasanquasaponin has anticancer activity (Fitoterapia, 84, 123-129, 2013) ( J. Nat. Prod ., 68, 1360-1365, 2005), theasaponin has been reported to have gastric mucosal protective effects ( J. Nat. Prod ., 69, 185-190, 2006).
녹차씨 추출물의 주요 항암 활성 물질은 폴리페놀계인 cathechin류와 플라보노이드계인 camelliaside류로 알려져 있으며, 최근 sasanquasaponin이 유방암 세포의 apoptosis를 유도하여 암세포를 사멸시키는 것으로 보고되었다(Fitoterapia, 84, 123-129, 2013).The main anticancer activity of green tea seed extract is known to be polyphenolic cathechin and flavonoid camelliaside. Recently, sasanquasaponin has been reported to induce apoptosis of breast cancer cells and kill cancer cells (Fitoterapia, 84, 123-129, 2013) .
종래의 발명은 녹차씨 추출물과 카테킨류를 포함하는 녹차씨 유래 폴리페놀 화합물들의 항암 및 항산화 효능에 대해서 주로 보고하였으나, 녹차씨 유래 사포닌류인 assamsaponin C, assamsaponin D, theasaponin E1의 항진균 효과와 항암 활성에 대해서는 알려진바가 없다. Conventional invention reported mainly anticancer and antioxidant efficacy of green tea seed polyphenol compounds including green tea seed extract and catechins. However, antimicrobial activity and anticancer activity of assamsaponin C, assamsaponin D and theasaponin E1 of green tea seed saponins There is no known information.
본원발명은 상기와 같은 문제점을 해결하기 위한 것으로 그 목적은 항진균 및 항암 효과를 가지는 녹차씨로부터 유래된 사포닌을 포함하는 녹차씨 조성물을 제공하기 위한 것이다.DISCLOSURE OF THE INVENTION The present invention provides a green tea seed composition comprising saponin derived from green tea seeds having antifungal and anti-cancer effects.
국산 녹차씨(Green tea seed)는 보성 및 하동지역에서 구매하여 외껍질을 제거하여 사용하였다. Green tea seeds were purchased from Boseong and Hadong area and used to remove outer skin.
외껍질을 탈피한 녹차씨를 0.001~0.5mm 크기의 입자로 분쇄한 후, 상기 분쇄된 녹차씨를 5~30배 중량의 물 또는 5~80% 에탄올(ethanol)을 각각 가한 뒤, 5~24시간 동안 25~35℃의 온도에서 교반추출하되, 바람직하게는 16시간 30℃에서 교반하여 사포닌류를 포함하는 녹차씨 추출물을 추출한다. 상기 녹차씨 추출물을 1~8㎛의 필터로 여과하고 농축하여 추출물을 얻는다. 상기 물 또는 에탄올 추출물을 하기 6종의 미생물에 대한 항균력을 평가하였다.The green tea seeds which have been peeled off from the outer skin are pulverized into particles having a size of 0.001 to 0.5 mm and then the pulverized green tea seeds are added with 5 to 30 times by weight of water or 5 to 80% The mixture is stirred at a temperature of 25 to 35 ° C, preferably for 16 hours at 30 ° C to extract green tea seed extract containing saponins. The green tea seed extract is filtered with a filter of 1 to 8 탆 and concentrated to obtain an extract. The water or ethanol extract was evaluated for the antimicrobial activity against the following six microorganisms.
본원발명은 녹차씨로부터 항진균 활성 성분의 최적 추출 조건을 평가하기 위해서 상기 녹차씨 분쇄물을 100%, 80%, 60%, 40%, 20% 에탄올 및 물로 각각, 25℃에서 16시간 동안 추출한 후 여과하고 감압 농축하여 녹차씨 추출물을 얻었으며, 또한 상기 녹차씨 분쇄물을 90℃의 물로 5시간 동안 열수추출 후 여과하고 감압농축하여 녹차씨 열수추출물을 얻었다. In order to evaluate the optimal extraction conditions of antifungal active ingredients from green tea seeds, the green tea seeds were extracted with 100%, 80%, 60%, 40%, 20% ethanol and water at 25 ° C for 16 hours Filtered and concentrated under reduced pressure to obtain a green tea seed extract. The green tea seeds were further extracted with hot water at 90 ° C for 5 hours, filtered, and concentrated under reduced pressure to obtain a green tea extract.
상기 녹차씨 추출물 및 열수추출물은 다시 추출한 용매로 녹인 다음 효모류인 칸디다 알비칸스(Candida albicans ATCC 10231)와 간장에서 분리한 산막 효모인 자이고사카로마이세스 룩시(Zygosaccharomyces rouxii)에 대한 항균력을 평가하였다.The green tea seed extract and the hot water extract were dissolved in the extracted solvent, and then the antibacterial activity against Zygosaccharomyces rouxii , which is a yeast isolate from Candida albicans ATCC 10231 and liver, was evaluated.
본원발명은 녹차씨 추출물의 열 및 pH 안정성을 평가하기 위하여 상기 60% 에탄올로 추출한 녹차씨 추출물을 다시 추출 용매로 10% 용액을 제조한 다음, 80℃, 100℃와 121℃에서 30분 동안 각각 열처리한 후 항균력을 평가하였다. 또한 pH 안정성은 1N HCl, 1N NaOH로 pH 3.0, pH 5.0, pH 7.0, pH 10.0으로 조정한 다음 실온에서 24시간 반응 후에 중화한 다음 항균력을 평가하였다. In order to evaluate the heat and pH stability of green tea seed extract, 10% solution of green tea seed extract extracted with 60% ethanol was prepared again at 80 ° C., 100 ° C. and 121 ° C. for 30 minutes After the heat treatment, the antimicrobial activity was evaluated. In addition, pH stability was adjusted to pH 3.0, pH 5.0, pH 7.0, pH 10.0 with 1N HCl, 1N NaOH, neutralized after reaction at room temperature for 24 hours, and then evaluated for antibacterial activity.
또한 본원발명은 녹차씨 추출물로부터 항진균 활성 물질 분리정제 및 구조를 동정하기 위하여 60% 에탄올로 추출한 녹차씨 추출물을 부탄올 분획(buthanol), 분취용 고성능 액체크로마토그래피(Preparative HPLC)로 분리 정제하였다.In order to identify the purification and structure of the antifungal active substance from green tea seed extract, green tea seed extract extracted with 60% ethanol was separated and purified by butanol fractionation preparative HPLC (preparative HPLC).
또한 본원발명은 녹차씨 추출물로부터 유래된 사포닌류의 생리활성을 검증하기 위하여 녹차씨로부터 분리한 사포닌류의 항진균 활성을 확인한 결과 Candida albicans에 대해서 156ppm의 MIC값을 나타내었고, 추출물 대비 6배 강한 활성을 보였다. In order to verify the physiological activities of saponins derived from green tea seed extract, the present invention was examined to examine the antifungal activities of saponins isolated from green tea seeds. As a result, Candida The MIC value of albicans was 156ppm, which was 6 times higher than that of the extract.
본 발명은 녹차씨 추출물로부터 유래된 사포닌류를 포함하는 조성물에 관한 것으로 상기 사포닌류를 포함하는 조성물은 항진균 및 항암 활성을 나타내는 조성물로 이를 정제하여 식품, 화장품, 의약품 또는 생활용품에도 적용할 수 있다.The present invention relates to a composition comprising saponins derived from green tea seed extract. The composition containing saponins can be applied to foods, cosmetics, medicines or household goods by purifying them with antifungal and anticancer activity .
녹차씨를 80% 에탄올 추출물과 물 추출물의 항균 활성 확인 결과, 항진균 활성에서도 특이적으로 효모 균주에 대해서만 우수한 항균 활성을 나타내었다. 또한 본원 발명의 녹차씨를 에탄올 추출물과 물 추출물에서 거의 유사하게 항암활성에 효과가 있는 것으로 나타났다.As a result of confirming the antimicrobial activity of 80% ethanol extract and water extract of green tea seed, the antimicrobial activity exclusively for yeast strain was also exhibited specifically also in antifungal activity. In addition, the green tea seeds of the present invention were found to have almost the same anticancer activity as the ethanol extract and the water extract.
본원 발명의 녹차씨 추출물의 에탄올 농도별 항균 활성을 평가한 결과 실온에서 추출 시, 물 추출물에서부터 80% 에탄올 추출물까지 항진균 활성이 우수하였으며, 특히 60% 에탄올로 추출한 녹차씨 추출물의 항진균 활성효과가 가장 좋았다. 또한 본원 발명의 열 안정성이 매우 높았으며, pH 안정성은 pH 3.0 에서 pH 10.0까지 모두 안정적인 활성을 나타냈다.The antimicrobial activity of the green tea seed extract of the present invention was evaluated by the ethanol concentration, and the antifungal activity was excellent from the water extract to the 80% ethanol extract at room temperature. Especially, the antifungal effect of green tea seed extract extracted with 60% it was good. In addition, the thermal stability of the present invention was very high, and the pH stability showed stable activity from pH 3.0 to pH 10.0.
도 1은 본 발명의 녹차씨 조성물의 사포닌류 LC-MS chromatogram
도 2는 본 발명의 LC-MS 주요 피크의 High resolution LC-MS/MS chromatogram
도 3. 본 발명의 항진균 활성 물질의 화학구조식
도 4. 본 발명의 녹차씨 추출물의 간장 보존 효과 그래프
도 5. 본 발명의 녹차씨 추출물의 화장품 방부 효과를 나타낸 그래프Fig. 1 is a graph showing the saponin-type LC-MS chromatogram
Figure 2 is a high resolution LC-MS / MS chromatogram of the LC-MS major peak of the present invention
3. The chemical structure of the antifungal active substance of the present invention
Fig. 4. Effect of green tea seed extract of the present invention on preservation of soy sauce
Figure 5. Graph showing the cosmetic preservation effect of the green tea seed extract of the present invention
이하에서는 녹차씨로부터 유래된 사포닌류를 포함하는 항진균 및 항암 활성 조성물 및 그 제조방법에 관하여 상세히 설명하기로 한다.Hereinafter, antifungal and anticancer active compositions including saponins derived from green tea seeds and a method for producing the same will be described in detail.
도 1은 본 발명의 녹차씨 조성물의 사포닌류 LC-MS chromatogram이고, 도 2는 본 발명의 LC-MS 주요 피크의 High resolution LC-MS/MS chromatogram이며, 도 3. 본 발명의 항진균 활성 물질의 화학구조식이다. 도 4. 본 발명의 녹차씨 추출물의 간장 보존 효과 그래프이고, 도 5. 본 발명의 녹차씨 추출물의 화장품 방부 효과를 나타낸 그래프를 나타낸 것이다.2 is a high-resolution LC-MS / MS chromatogram of the LC-MS main peak of the present invention. Fig. 3 is a graph showing the LC-MS chromatogram of saponins of the present antifungal active substance It is a chemical structural formula. FIG. 4 is a graph showing the soy sauce preservation effect of the green tea seed extract of the present invention, and FIG. 5 is a graph showing the cosmetic preservation effect of the green tea seed extract of the present invention.
본 발명의 녹차씨로부터 유래된 사포닌류 조성물은 국산 녹차씨(Green tea seed)를 구입하여 외껍질을 제거하여 사용하였다. 국산 녹차씨(Green tea seed)는 보성 및 하동지역에서 구매하여 외껍질을 제외껍질을 탈피한 녹차씨를 0.001~0.5mm 크기의 입자로 분쇄한 후, 상기 분쇄된 녹차씨를 5~30배 중량의 물 또는 5~80% 에탄올(ethanol)을 각각 가한 뒤, 5~24시간 동안 25~35℃의 온도에서 교반추출하되, 바람직하게는 16시간 30℃에서 교반하여 사포닌류를 포함하는 녹차씨 추출물을 추출한다. 상기 녹차씨 추출물을 1~8㎛의 필터로 여과하고 농축하여 추출물을 얻는다. 상기 물 또는 에탄올 추출물로 구성되는 조성물을 하기 6종의 미생물에 대한 항균력을 평가하였다.The saponin composition derived from green tea seeds of the present invention was obtained by purchasing a green tea seed and removing the outer shell. The green tea seeds were purchased from Boseong and Hadong, and the green tea seeds, which had been peeled off the outer shells, were crushed into particles having a size of 0.001-0.5 mm. Then, the crushed green tea seeds were weighed 5 ~ 30 times Or 5 to 80% ethanol, and then stirred for 5 to 24 hours at a temperature of 25 to 35 ° C., preferably for 16 hours at 30 ° C. to extract green tea seed extract containing saponins do. The green tea seed extract is filtered with a filter of 1 to 8 탆 and concentrated to obtain an extract. The composition consisting of the water or the ethanol extract was evaluated for the antibacterial activity against the following six microorganisms.
상기와 같이 추출한 녹차씨 추출 조성물에는 녹차씨 건조물 대비 15% 이상의 사포닌을 함유하고 있으며, camelliasapoins, sasanquasaponin, assamsaponins, theasaponins 및 floratheasaponins 등의 사포닌류가 다량 함유되어 있다.The green tea seed extract composition thus extracted contains at least 15% of saponin in comparison with the dried green tea seeds, and contains a large amount of saponins such as camelliasapoins, sasanquasaponin, assamsaponins, theasaponins and floratheasaponins.
본원발명은 녹차씨로부터 항진균 활성 성분의 최적 추출 조건을 평가하기 위해서 상기 녹차씨 분쇄물을 100%, 80%, 60%, 40%, 20% 에탄올 및 물로 각각, 25℃에서 16시간 동안 추출한 후 여과하고 감압 농축하여 녹차씨 추출물을 얻었으며, 또한 상기 녹차씨 분쇄물을 90℃의 물로 5시간 동안 열수추출 후 여과하고 감압농축하여 녹차씨 열수추출물을 얻었다. In order to evaluate the optimal extraction conditions of antifungal active ingredients from green tea seeds, the green tea seeds were extracted with 100%, 80%, 60%, 40%, 20% ethanol and water at 25 ° C for 16 hours Filtered and concentrated under reduced pressure to obtain a green tea seed extract. The green tea seeds were further extracted with hot water at 90 ° C for 5 hours, filtered, and concentrated under reduced pressure to obtain a green tea extract.
상기 녹차씨 추출물 및 열수추출물은 다시 추출한 용매로 녹인 다음 효모류인 칸디다 알비칸스(Candida albicans ATCC 10231)와 간장에서 분리한 산막 효모인 자이고사카로마이세스 룩시(Zygosaccharomyces rouxii)에 대한 항균력을 평가하였다.The green tea seed extract and the hot water extract were dissolved in the extracted solvent, and then the antibacterial activity against Zygosaccharomyces rouxii , which is a yeast isolate from Candida albicans ATCC 10231 and liver, was evaluated.
본원발명은 녹차씨 추출물의 열 및 pH 안정성을 평가하기 위하여 상기 60% 에탄올로 추출한 녹차씨 추출물을 다시 추출 용매로 10% 용액을 제조한 다음, 80℃, 100℃와 121℃에서 30분 동안 각각 열처리한 후 항균력을 평가하였다. 또한 pH 안정성은 1N HCl, 1N NaOH로 pH 3.0, pH 5.0, pH 7.0, pH 10.0으로 조정한 다음 실온에서 24시간 반응 후에 중화한 다음 항균력을 평가하였다. In order to evaluate the heat and pH stability of green tea seed extract, 10% solution of green tea seed extract extracted with 60% ethanol was prepared again at 80 ° C., 100 ° C. and 121 ° C. for 30 minutes After the heat treatment, the antimicrobial activity was evaluated. In addition, pH stability was adjusted to pH 3.0, pH 5.0, pH 7.0, pH 10.0 with 1N HCl, 1N NaOH, neutralized after reaction at room temperature for 24 hours, and then evaluated for antibacterial activity.
또한 본원발명은 녹차씨 추출물로부터 항진균 활성 물질 분리정제 및 구조를 동정하기 위하여 60% 에탄올로 추출한 녹차씨 추출물을 부탄올 분획(buthanol), 분취용 고성능 액체크로마토그래피(Preparative HPLC)로 분리 정제하였다.In order to identify the purification and structure of the antifungal active substance from green tea seed extract, green tea seed extract extracted with 60% ethanol was separated and purified by butanol fractionation preparative HPLC (preparative HPLC).
또한 본원발명은 녹차씨 추출물로부터 유래된 사포닌류의 생리활성을 검증하기 위하여 녹차씨로부터 분리한 사포닌류의 항진균 활성을 확인한 결과 Candida albicans에 대해서 156ppm의 MIC값을 나타내었고, 추출물 대비 6배 강한 활성을 보였다. In order to verify the physiological activities of saponins derived from green tea seed extract, the present invention was examined to examine the antifungal activities of saponins isolated from green tea seeds. As a result, Candida The MIC value of albicans was 156ppm, which was 6 times higher than that of the extract.
1. 녹차씨 추출물의 항균력 평가1. Evaluation of antibacterial activity of green tea seed extract
실험에 사용한 미생물은 세균으로는 바실러스 세레우스(Bacillus cereus ATCC 21768), 스타필로코커스 아우레우스(Staphylococcus aureus ATCC 6538) 및 에스케리치아 콜리(Escherichia coli ATCC 25922), 슈도모나스 에어루지노사(Pseudomonas aeruginosa ATCC 9027) 균주를 사용하였고, 진균으로는 간장에서 분리한 자이고사카로마이세스 룩시(Zygosaccharomyces rouxii), 칸디다 알비칸스(Candida albicans ATCC 10231) 및 아스퍼질러스 나이거(Aspergillus niger ATCC 16404)를 사용하였다. The microorganisms used in the experiment were Bacillus cereus ATCC 21768, Staphylococcus aureus ATCC 6538 and Escherichia coli. coli ATCC 25922), Pseudomonas aeruginosa aeruginosa ATCC 9027) was used as a fungus. As fungi, Zygosaccharomyces sp. rouxii), Candida albicans (Candida albicans ATCC 10231) and Aspergillus niger ATCC 16404 were used.
세균은 Tryptic soy agar 배지에서 전배양하고 이를 105-6CFU/㎖ 농도가 되도록 희석하여 접종 균액으로 준비하였으며, 진균은 Potato dextrose agar 배지에서 전 배양한 후 104-5CFU/㎖의 접종액이 되도록 희석하여 준비하였다. 항균력 테스트에 사용한 액체배지는 세균용으로 TSB를 사용하였으며, 진균용으로는 PDB를 사용하였다.Bacteria were pre-cultured in Tryptic soy agar medium and diluted to a concentration of 5-6 CFU / ml to prepare inoculum. The fungi were pre-cultured in Potato dextrose agar medium and then inoculated with 10 4-5 CFU / Lt; / RTI > The liquid medium used for the antibacterial test was TSB for bacteria and PDB for fungi.
2. 녹차씨 추출물의 항암활성 평가2. Evaluation of anticancer activity of green tea seed extract
녹차씨 추출물을 DMSO(Dimethy sulfoxide)에 10％ 용액으로 희석한 후, DEME 배지를 이용하여 1/10씩 계열 희석하여 세포에 적용하였다. 세포는 피부세포인 Human dermal fibroblast(HDF)와 쥐의 대식세포에서 유래한 RAW 264.7 cell line(Mouse leukaemic monocyte macrophage cell line)을 사용하였다.Green tea seed extract was diluted with DMSO (Dimethy sulfoxide ) in 10% solution and then diluted 1/10 in DEME medium. Human dermal fibroblast (HDF), a skin cell, and RAW 264.7 cell line (mouse leukaemic monocyte macrophage cell line) derived from mouse macrophages were used.
3. 녹차씨 추출물의 간장 보존 효과3. Soybean preservation effect of green tea seed extract
본 발명의 녹차씨 추출물의 적용 효능을 확인하기 위해서, 주정을 포함한 보존료가 첨가되지 않은 간장으로 보존 효능 테스트를 실시하였다. 무보존료 간장에 녹차씨 추출물을 0.1%, 0.01%, 0.001% 첨가한 후, 간장 산막 발생 효모 균주인 자이고사카로마이세스 룩시 (Zygosaccharomyces rouxii)를 104CFU/ml(Colony forming uinit/ml) 접종 한 다음 30℃에 보관하면서 균주 사멸율을 확인하였다.In order to confirm the application efficacy of the green tea seed extract of the present invention, a preservation efficacy test was conducted with soy sauce containing no preservative including alcohol. After 0.1%, 0.01%, and 0.001% of green tea seed extract was added to soy sauce, Zygosaccharomyces sp. rouxii ) was inoculated with 10 4 CFU / ml (colony forming uinit / ml) and stored at 30 ° C.
간장 적용 결과 녹차씨를 60% 에탄올로 추출한 추출물의 농도가 0.1%, 0.01% 농도인 경우에 간장 산막 효모를 100% 사멸시켰으며, 반면에 대조구인 80% 발효주정을 1% 처리한 실험구에서는 산막 효모가 제어되지 않았다. 따라서 균을 과량으로 접종한 가혹 실험에서도 간장의 효모 증식 억제 효과가 우수하기 때문에, 실제 간장과 같이 초기 균이 거의 없는 상태에서는 녹차씨 추출물의 산막 효모 제어 효능이 더욱 효과적일 것으로 사료된다.As a result of application of soy sauce, 100% of soy sauce yeast was killed in the case of 0.1% and 0.01% concentration of extract of 60% ethanol of green tea seed, whereas in the experimental group treated with 1% of 80% Yeast was not controlled. Therefore, it is considered that the yeast control effect of the green tea seed extract is more effective in the case where there is little initial bacterium such as the actual liver, since the yeast growth inhibition effect of the liver is excellent even in the case of the harsh experiment in which the bacteria are overexcited.
4. 녹차씨 추출물의 화장품 방부 효과4. Cosmetic preservation effect of green tea seed extract
본 발명의 녹차씨 추출물의 화장품 적용 효능을 확인하기 위해서, 화장품 크림제형을 만들어서 25℃ 인큐베이터에 보관하여 무처리구 대비 균 감소 여부를 확인하였다. 무보존료 화장품에 녹차씨를 60% 에탄올로 추출한 추출물의 농도 0.1%, 0.01%, 0.001%를 첨가하여 칸디다 알비칸스(C. albicans)를 접종한 후, 1개월 동안 균 사멸정도를 Petrifilm으로 확인하였다. In order to confirm the efficacy of the green tea seed extract of the present invention in cosmetics, a cosmetic cream formulation was prepared and stored in an incubator at 25 ° C to confirm whether or not the antibacterial effect was reduced compared to the control. A no-preservative cosmetics Candida albicans (C. Albicans) was added to a concentration of 0.1% of the extract extracted seed green tea in 60% ethanol, 0.01%, 0.001% to after inoculation, the bacterial kill degree was confirmed by Petrifilm for one month.
상기 균을 전 배양하여 1×106CFU/g이 되도록 접종한 후, 상기 녹차씨 추출물을 농도별로 각각 첨가한 후, 1 ~ 28일까지 시간 경과를 관찰하여 그래프화 하였다.The bacteria were pre-cultured and inoculated to a concentration of 1 × 10 6 CFU / g. The green tea seed extract was added to each concentration, and the time course was observed from 1 to 28 days.
이하에서는 실시예를 통해 본 발명을 더욱 상세히 설명하고자 하며, 다만 이하에 실시예 등에 의해 본 발명의 범위와 내용이 축소되거나 제한되어 해석될 수 없다. 또한, 이하의 실시예를 포함한 본 발명의 개시 내용에 기초한다면, 구체적으로 실험 결과가 제시되지 않은 본 발명을 통상의 기술자가 용이하게 실시할 수 있음은 명백한 것이며, 이러한 변형 및 수정이 첨부된 특허청구범위에 속하는 것도 당연하다.Hereinafter, the present invention will be described in more detail with reference to the following examples, but the scope and content of the present invention can not be construed to be limited or limited by the following examples. It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit and scope of the present invention as set forth in the following claims. It is natural that it belongs to the claims.
실시예 1. 녹차씨 추출물의 항균력 평가Example 1. Evaluation of antibacterial activity of green tea seed extract
국산 녹차씨(Green tea seed)는 보성 및 하동지역에서 구매하여 외껍질을 제거하여 사용하였다. 탈피한 녹차씨를 분쇄한 후, 분쇄된 녹차씨에 15배수의 물과 80% 에탄올(80% ethanol)을 각각 가한 뒤, 16시간 30℃에서 교반 추출한 후, 8 ㎛이하의 필터로 여과하고 농축하여 추출물을 얻는다. 각 추출물을 하기 6종의 미생물에 대한 항균력을 평가하였다.Green tea seeds were purchased from Boseong and Hadong area and used to remove outer skin. 15% of water and 80% ethanol were added to the ground green tea seeds, and the mixture was stirred for 16 hours at 30 ° C, filtered through a filter having a diameter of 8 μm or less, and concentrated. The extract is obtained. Each extract was evaluated for the antimicrobial activity against the following six microorganisms.
실험에 사용한 미생물은 세균으로는 바실러스 세레우스(Bacillus cereus ATCC 21768), 스타필로코커스 아우레우스(Staphylococcus aureus ATCC 6538) 및 에스케리치아 콜리(Escherichia coli ATCC 25922), 슈도모나스 에어루지노사(Pseudomonas aeruginosa ATCC 9027) 균주를 사용하였고, 진균으로는 간장에서 분리한 자이고사카로마이세스 룩시(Zygosaccharomyces rouxii), 칸디다 알비칸스(Candida albicans ATCC 10231) 및 아스퍼질러스 나이거(Aspergillus niger ATCC 16404)를 사용하였다. The microorganisms used in the experiment were Bacillus cereus ATCC 21768, Staphylococcus aureus ATCC 6538 and Escherichia coli. coli ATCC 25922), Pseudomonas aeruginosa aeruginosa ATCC 9027) was used as a fungus. As fungi, Zygosaccharomyces sp. rouxii), Candida albicans (Candida albicans ATCC 10231) and Aspergillus niger ATCC 16404 were used.
세균은 Tryptic soy agar(TSA, pancreatic digest of casein 15g, papaic digest of soybean 5g, sodium chloride 5g, agar 15g)에서 37℃ 온도로 24시간 전배양하고 이를 105-6CFU/㎖ 농도가 되도록 희석하여 접종 균액으로 준비하였으며, 진균은 Potato dextrose agar(PDA, potato starch 4g, dextrose 20g, agar 15g) 배지로 30℃에서 24시간 동안 전 배양한 후 104-5CFU/㎖의 접종액이 되도록 희석하여 준비하였다. 항균력 테스트에 사용한 액체배지는 세균용으로 TSB를 사용하였으며, 진균용으로는 PDB를 사용하였다.Bacteria were preincubated at 37 ℃ for 24 hours in Tryptic soy agar (TSA, 15 g of pancreatic digest of casein, 5 g of papaic digest of soybean, 5 g of sodium chloride, 15 g of agar) and diluted to 10 5-6 CFU / The fungi were preincubated for 24 h at 30 ° C in a medium of Potato dextrose agar (PDA, potato starch 4 g, dextrose 20 g, agar 15 g) and diluted to 10 4-5 CFU / ㎖ of inoculum Prepared. The liquid medium used for the antibacterial test was TSB for bacteria and PDB for fungi.
항균력 테스트는 CLSI방법(The Clinical and Laboratory Standards Institute guideline)에 따라 microdilution법으로 하였으며, 세균은 배양 24시간 후, 진균은 배양 48시간 후 결과를 확인하여, 최소생육저해농도(MIC, Minimal Inhibitory Concentration)로 나타내었다. 그 결과를 하기 [표 1]에 나타내었다.The bacterial counts were determined 24 hours after culture and 48 hours after incubation. The results were compared with those of the Minimal Inhibitory Concentration (MIC) Respectively. The results are shown in Table 1 below.
녹차씨 80% 에탄올 추출물과 물 추출물의 항균 활성 확인 결과, 항세균 활성은 없었으며 항진균 활성에서도 특이적으로 효모 균주에 대해서만 우수한 항균 활성을 나타내었다. The antimicrobial activity of 80% ethanol extract and water extract of green tea seed showed no antibacterial activity and showed antimicrobial activity exclusively for yeast strains even in antifungal activity.
실시예 2. 녹차씨 추출물의 항암활성 평가Example 2. Evaluation of anticancer activity of green tea seed extract
녹차씨 추출물을 DMSO에 10％ 용액으로 희석한 후, DEME 배지를 이용하여 1/10씩 계열 희석하여 세포에 적용하였다. 세포는 피부세포인 Human dermal fibroblast(HDF)와 쥐의 대식세포에서 유래한 RAW 264.7 cell line(Mouse leukaemic monocyte macrophage cell line)을 사용하였다.Green tea seed extract was diluted with DMSO in 10% solution and then diluted 1/10 in DEME medium. Human dermal fibroblast (HDF), a skin cell, and RAW 264.7 cell line (mouse leukaemic monocyte macrophage cell line) derived from mouse macrophages were used.
상기 [표 2]에서와 같이 녹차씨의 에탄올 추출물과 물 추출물에서 거의 유사하게 항암활성이 있는 것으로 나타났다.As shown in [Table 2], the ethanol extracts of green tea seeds showed almost similar anticancer activities to the water extracts.
실시예 3. 녹차씨 추출물의 복귀돌연변이 시험Example 3: Return mutation test of green tea seed extract
녹차씨 추출물의 미생물 복귀돌연변이 유발 여부를 평가하기 위하여 Salmonella typhimurium의 히스디딘(histidine) 요구성 균주인 TA98, TA100, TA1535 및 TA 1537의 4개의 균주와 대장균(Escherichia coli)의 트립토판(tryptophan) 요구성 균주인 WP2uvrA를 이용하여 시험을 실시하였다. 실험예 1의 녹차씨 추출물을 DMSO에 용해한 다음 5,000㎍/plate를 최고농도로 하여 1,000, 500, 100 및 50㎍/plate 단계 희석하여 실시한 농도결정시험을 토대로 하여 본 시험에서는 5,000㎍/plate를 최고 농도로 하여 공비 2로 단계 희석하여 대사활성계 미적용(S9-) 및 적용 (S9+)에서 음성 및 양성 대조군과 함께 시험을 실시하였다.In order to evaluate the mutagenicity of green tea seed extract, four strains of TA98, TA100, TA1535 and TA1537, which are histidine requisites of Salmonella typhimurium , and Escherichia The test was performed using WP2uvrA, a tryptophan-requiring strain of E. coli . The green tea seed extract of Experimental Example 1 was dissolved in DMSO and then diluted to 1,000, 500, 100 and 50 μg / plate at the highest concentration of 5,000 μg / plate. In this test, 5,000 μg / (S9-) and application (S9 +) with the negative and positive control groups.
시험 결과, Salmonella typhimurium TA98, TA100, TA1535 및 TA 1537 및 대장균(Escherichia coli )의 트립토판(tryptophan) WP2uvrA 5균주에 대해 대사활성계 미적용 (S9-) 및 적용(S9+) 모두 음성 대조군과 비교하여 각 농도별 시험물질 처리군에서의 복귀돌연변이 콜로니 수는 증가 양상을 나타내지 않았다. 따라서 녹차씨 추출물은 상기 시험 조건하에 사용한 균주들에 대하여 복귀돌연변이를 유발하지 않으므로 돌연변이 유발성 물질이 존재하지 않는 것으로 판단된다.The test results, Salmonella typhimurium TA98, TA100, TA1535, and TA 1537 and Escherichia coli (Escherichia coli) tryptophan (tryptophan) each concentration of metabolic activation system unapplied (S9-) and applied to a WP2uvrA 5 strains both (S9 +) compared to the negative control, the The number of return mutant colonies in the test substance treated group did not show an increase pattern. Therefore, the green tea seed extract does not induce a return mutation in the strains used under the above test conditions, and thus it is judged that no mutagenic substance is present.
실시예 4. 녹차씨로부터 항진균 활성 성분의 최적 추출 조건 평가Example 4. Evaluation of optimum extraction conditions of antifungal active ingredients from green tea seeds
녹차씨 분쇄물을 100%, 80%, 60%, 40%, 20% 에탄올 및 물로 각각, 25℃에서 16시간 동안 추출한 후 여과하고 감압 농축하여 추출물을 얻었으며, 물로 90℃에서 5시간 동안 열수추출 후 여과하고 감압농축하여 녹차씨 열수추출물을 얻었다. 추출물은 다시 추출한 용매로 녹인 다음 효모류인 칸디다 알비칸스(Candida albicans ATCC 10231)와 간장에서 분리한 산막 효모인 자이고사카로마이세스 룩시(Zygosaccharomyces rouxii)에 대한 항균력을 평가하였다.The green tea seeds were extracted with 100%, 80%, 60%, 40%, 20% ethanol and water at 25 ℃ for 16 hours, respectively, and concentrated under reduced pressure to obtain an extract. The extract was filtered and concentrated under reduced pressure to obtain a green tea hydrothermal extract. The extract was dissolved in the extracted solvent, and the yeast Candida albicans ( Candida albicans ATCC 10231) and Zygosaccharomyces rouxii , a diaphragm yeast isolated from soy sauce.
녹차씨 추출물의 에탄올 농도별 항균 활성 평가 결과, 상기 [표 3]에서 나타내는 바와 같이 실온에서 추출 시, 물 추출물에서부터 80% 에탄올 추출물까지 항진균 활성이 우수하였으며, 특히 60% 에탄올로 추출한 녹차씨 추출물의 항진균 활성이 가장 우수하였다. 그러나 100% 에탄올 추출물은 오히려 항진균 활성이 약하게 나타났으며, 녹차씨를 물로 실온과 90℃에서 추출하였을 때, 실온 추출물의 항균력이 2배 강하게 나타났다. 따라서, 하기 실험에서는 항균력이 가장 우수한 60% 에탄올로 추출한 녹차씨 추출물을 사용하였다.As a result of evaluation of antimicrobial activity of the green tea seed extract according to the ethanol concentration, the antifungal activity was excellent from the water extract to the 80% ethanol extract at room temperature as shown in Table 3. As shown in Table 3, The antifungal activity was the best. However, 100% ethanol extract showed weak antifungal activity. When green tea seed was extracted with water at room temperature and 90 ℃, the antimicrobial activity of room temperature extract was 2 times stronger. Therefore, in the following experiment, green tea seed extract extracted with 60% ethanol having the best antibacterial activity was used.
실시예 5. 녹차씨 추출물의 열 및 pH 안정성 평가Example 5 Evaluation of Heat and pH Stability of Green Tea Seed Extract
녹차씨의 60% 에탄올 추출물을 다시 추출 용매로 10% 용액을 제조한 다음, 80℃, 100℃와 121℃에서 30분 동안 각각 열처리한 후 항균력을 평가하였다.The 60% ethanol extract of green tea seeds was again prepared as a 10% solution by extraction solvent and then heat treated at 80 ℃, 100 ℃ and 121 ℃ for 30 min, respectively, and the antibacterial activity was evaluated.
열 안정성 평가 결과, 상기 [표 4]에서 나타내는 바와 같이 녹차씨 추출물이 121℃ 고온 처리 시에만 C. albicans에 대한 항균력이 25% 상승하였고, Z. rouxii에 대한 항균력이 25% 감소하였으나, 100℃ 이하에서는 열처리에 따른 항균 활성의 차이가 없었으므로 열 안정성이 매우 높은 것으로 판단된다.Thermal stability evaluation results, the Table 4 only when the said green tea extract 121 ℃ high temperature treatment, as shown in C. The antimicrobial activity was up 25% on albicans, Z. The antimicrobial activity against rouxii was decreased by 25%, but the heat stability was very high because the antimicrobial activity was not changed by heat treatment below 100 ℃.
녹차씨의 60% 에탄올 추출물을 다시 추출 용매로 10% 용액을 제조한 다음, 1N HCl, 1N NaOH로 pH 3.0, pH 5.0, pH 7.0, pH 10.0으로 조정한 다음 실온에서 24시간 반응 후에 중화한 다음 항균력을 평가하였다. A 10% solution of 60% ethanol extract of green tea extract was prepared again with extraction solvent and adjusted to pH 3.0, pH 5.0, pH 7.0, pH 10.0 with 1N HCl, 1N NaOH, neutralized after reaction at room temperature for 24 hours The antibacterial activity was evaluated.
pH 안정성 평가 결과, 상기 [표 5]에서 나타내는 바와 같이 pH 3.0 에서 pH 10.0까지 모두 안정적인 활성을 나타내는 것을 확인 할 수 있었다. 이에 녹차씨 추출물 유래 항진균 활성물질은 pH 변화에 매우 안정한 것으로 판단된다.As a result of the evaluation of pH stability, it was confirmed that all of the activity from pH 3.0 to pH 10.0 showed stable activity as shown in Table 5 above. Therefore, it is considered that the antifungal active substance derived from green tea seed extract is very stable against pH change.
실시예 6. 녹차씨 추출물로부터 항진균 활성 물질 분리정제 및 구조 동정 Example 6 Isolation and Purification and Structure Identification of Antifungal Active Substances from Green Tea Seed Extract
60% 에탄올로 추출한 녹차씨 추출물을 부탄올 분획(buthanol), 분취용 고성능 액체크로마토그래피(Preparative HPLC)로 분리 정제하였다. The green tea seed extract extracted with 60% ethanol was separated and purified by butanol fractionation preparative HPLC.
녹차씨 추출물의 항진균 활성물질을 분리정제하기 위하여 우리나라에서 수확한 녹차씨 100g에 60% 에탄올(Ethanol) 900g을 가하여 실온에서 1일 정치하여 추출액을 얻었다. 이 여액을 여과지(Whatman filter paper No. 2)로 여과하여 회전식 진공 농축기로 감압 농축하여 녹차씨 추출물을 얻었다. 이 추출물에 60% 에탄올을 첨가하여 40% 용액을 만들었고, 이 용액에 동량의 클로로포름, 에틸아세테이트, 부탄올을 순차적으로 첨가하여 용매 분획하였고, 각 용매 분획을 감압 농축하여 건조물을 얻었다. 이 중 부탄올 분획에서 항진균 활성을 보였고, 유효 물질을 동정하고자 [표 6] 조건에 따라 분취용 HPLC로 유효성분을 정제하였다. HPLC 분획 중에서 항진균활성이 강한 5번 분획에서 사포닌 유도체가 3종 포함된 것을 확인하였고, LC-MS와 high resolution LC-MS/MS를 수행하였으며, 문헌자료와 비교하여 유효성분의 구조를 확인하였다.In order to separate and purify the antifungal active substance of green tea seed extract, 900 g of 60% ethanol (Ethanol) was added to 100 g of green tea seeds harvested from Korea, and the mixture was allowed to stand at room temperature for 1 day to obtain an extract. The filtrate was filtered through a filter paper (Whatman filter paper No. 2) and concentrated under reduced pressure using a rotary vacuum concentrator to obtain green tea seed extract. 60% ethanol was added to this extract to make a 40% solution. The same amount of chloroform, ethyl acetate, and butanol were sequentially added to this solution to separate the solvent fraction, and each solvent fraction was concentrated under reduced pressure to obtain a dried product. The active ingredient was purified by preparative HPLC according to the condition of [Table 6] in order to identify the active substance. It was confirmed that saponin derivatives were contained in fraction No. 5 with strong antifungal activity in HPLC fraction. LC-MS and high resolution LC-MS / MS were performed and the structure of active ingredient was confirmed by comparing with literature data.
녹차씨 유래 항진균 활성 물질의 LC-MS chromatogram과 주요 피크의 HR-LC-MS/MS chromatogram을 상기 [도 1]과 [도 2]에 각각에 나타내었으며, LC-MS 분석 결과 15.97분, 16.32분, 16.89분에서 주요 활성물질이라 예상되는 피크가 검출되었고, 이 피크들을 high resolution LC-MS/MS 를 수행하여 분석하였다. 그 결과, negative ion mode에서 각각 m/z 1231.5958 [M - H]-, m/z 1231.5845 [M - H]-, m/z 1229.5736 [M - H]- 이온들이 검출되었다. 각 peak들의 mass fragment ion들을 분석한 결과, 공통적으로 3-O-β-D-galactopyranosyl와 β-D-xylopyranosyl, α-L-arabinopyranosyl, β-D-glucopyranosiduronic acid 등 4개의 당과, angeloyl 그룹과 acetyl 그룹을 함유하고 있는 assamsaponin D (m/z 1232.5724), assamsaponin C (m/z 1232.5567), theasaponin E1 (m/z 1230.5562)로 동정되었다. 위 3개의 배당체 사포닌들은 이미 녹차씨에서 위장 보호 효과를 보이는 물질로 보고되었으나, 그 항진균 활성 및 항암활성에 대해서는 보고된 바가 없다 (Chem. Pharm. Bull., 48, 1720-1725, 2000, Chem. Pharm. Bull., 46, 1901-1906, 1998, J. Nat. Prod., 69, 185-190, 2006).The LC-MS chromatogram of the antifungal active substance derived from green tea seeds and the HR-LC-MS / MS chromatogram of the main peak are shown in FIGS. 1 and 2, respectively. The results of LC-MS analysis showed 15.97 minutes, 16.32 minutes , A peak expected to be a major active material was detected at 16.89 minutes, and these peaks were analyzed by performing high resolution LC-MS / MS. As a result, m / z 1231.5958 [M - H] - , m / z 1231.5845 [M - H] - and m / z 1229.5736 [M - H] - ions were detected in negative ion mode. As a result of analyzing the mass fragment ions of each peak, 4 sugars such as 3- O - β- D-galactopyranosyl and β- D-xylopyranosyl, α- L-arabinopyranosyl and β- D-glucopyranosiduronic acid, ( m / z 1232.5724), assamsaponin C ( m / z 1232.5567), and theasaponin E1 ( m / z 1230.5562) containing acetyl groups. The above three glycoside saponins have already been reported as gastrointestinal protective substances in green tea seeds, but no antifungal activity or anticancer activity has been reported (Chem. Pharm. Bull., 48, 1720-1725, 2000, Chem. Pharm. Bull., 46, 1901-1906, 1998, J. Nat. Prod., 69, 185-190, 2006).
실시예 7. 녹차씨 유래 사포닌류의 생리활성 검증Example 7. Verification of physiological activity of saponins derived from green tea seeds
녹차씨로부터 분리한 사포닌류의 항진균 활성을 확인한 결과 [표 7]에 나타낸 것과 같이 Candida albicans에 대해서 156ppm의 MIC값을 나타내었고, 추출물 대비 6배 강한 활성을 보였다. Results confirmed the antifungal activity of saponins isolated from green tea seed Candida, as shown in Table 7 The MIC value of albicans was 156ppm, which was 6 times higher than that of the extract.
또한, 녹차씨로부터 분리한 사포닌류의 항암 활성을 확인한 결과 [표 8]과 같이 ppm 수준에서 강한 항암 활성을 나타내었고, 이는 선행 연구에서 밝혀진 다른 종의 녹차씨(seeds of Camellia oleifera) 사포닌인 sasanquasaponin의 항암 활성보다 강한 활성인 것을 확인하였다(Fitoterapia, 84, 321-325, 2013).In addition, the anticancer activity of saponins isolated from green tea seeds showed strong anticancer activity at ppm level as shown in [Table 8]. This indicates that sasanquasaponin (saponin), a seeds of Camellia oleifera saponin, (Fitoterapia, 84, 321-325, 2013).
실시예 8. 녹차씨 추출물의 간장 보존 효과Example 8. Effect of Green Tea Seed Extract on Liver Preservation
본 발명의 녹차씨 추출물의 적용 효능을 확인하기 위해서, 주정을 포함한 보존료가 첨가되지 않은 간장으로 보존 효능 테스트를 실시하였다. 무보존료 간장에 녹차씨 추출물을 0.1%, 0.01%, 0.001% 첨가한 후, 간장 산막 발생 효모 균주인 자이고사카로마이세스 룩시 (Zygosaccharomyces rouxii)를 104CFU/ml(Colony forming uinit/ml) 접종 한 다음 30℃에 보관하면서 균주 사멸율을 확인하였다.In order to confirm the application efficacy of the green tea seed extract of the present invention, a preservation efficacy test was conducted with soy sauce containing no preservative including alcohol. After 0.1%, 0.01%, and 0.001% of green tea seed extract was added to soy sauce, Zygosaccharomyces sp. rouxii ) was inoculated with 10 4 CFU / ml (colony forming uinit / ml) and stored at 30 ° C.
간장 적용 결과, [도 4]에서 나타내는 바와 같이 녹차씨 60% 에탄올 추출물 0.1%, 0.01% 농도에서 간장 산막 효모를 100% 사멸시켰으며, 반면에 대조구인 80% 발효주정을 1% 처리한 실험구에서는 산막 효모가 제어되지 않았다. 따라서 균을 과량으로 접종한 가혹 실험에서도 간장의 효모 증식 억제 효과가 우수하기 때문에, 실제 간장과 같이 초기 균이 거의 없는 상태에서는 녹차씨 추출물의 산막 효모 제어 효능이 더욱 효과적일 것으로 사료된다.As shown in Fig. 4, 100% of soy sauce yeast was killed at the concentration of 0.1% and 0.01% of 60% ethanol extract of green tea, whereas in the case of 1% treatment of 80% , The membrane yeast was not controlled. Therefore, it is considered that the yeast control effect of the green tea seed extract is more effective in the case where there is little initial bacterium such as the actual liver, since the yeast growth inhibition effect of the liver is excellent even in the case of the harsh experiment in which the bacteria are overexcited.
실시예 9. 녹차씨 추출물의 화장품 방부 효과Example 9. Preservative effect of cosmetic product of green tea seed extract
본 발명의 녹차씨 추출물의 화장품 적용 효능을 확인하기 위해서, 화장품 크림제형을 만들어서 25℃ 인큐베이터에 보관하여 무처리구 대비 균 감소 여부를 확인하였다. 무보존료 화장품에 녹차씨 60% 에탄올 추출물을 0.1%, 0.01%, 0.001% 첨가하여 칸디다 알비칸스(C. albicans)를 접종한 후, 1개월 동안 균 사멸정도를 Petrifilm으로 확인하였다. In order to confirm the efficacy of the green tea seed extract of the present invention in cosmetics, a cosmetic cream formulation was prepared and stored in an incubator at 25 ° C to confirm whether or not the antibacterial effect was reduced compared to the control. After the preservative-free cosmetic Candida albicans (C. Albicans) to the green tea seeds 60% ethanol extract was added 0.1%, 0.01%, 0.001% to inoculation, the bacteria killed approximately for 1 month was confirmed by Petrifilm.
상기 화장품의 방부력을 측정하는 방법으로 USP와 CTFA 방법이 많이 사용되고 있으며, 본 시험 방법은 미국화장품공업협회(Cosmetic, Toiletry, and Fragrance Assocition, 이하 CTFA)의 미생물 가이드라인의 시험법을 사용하였다. 상기 균을 전 배양하여 1×106CFU/g이 되도록 접종한 후, 상기 녹차씨 추출물을 농도별로 각각 첨가한 후, 1 ~ 28일까지 시간 경과를 관찰하여 그래프화 하였다. CTFA기준에 따른 방부력 유효성으로 세균은 접종 7일 이내 99.9％ 이상 균수가 감소해야 하며, 시험기간 동안 증식이 없어야 하고, 진균은 접종 7일 이내에 적어도 90％ 이상 미생물 수가 감소해야 하며, 시험기간 중 지속적으로 미생물 수가 감소해야 한다.USP and CTFA methods are widely used as methods for measuring the buoyancy of the cosmetics, and the test method of the microorganism guideline of Cosmetic, Toiletry, and Fragrance Assay (CTFA) was used. The bacteria were pre-cultured and inoculated to a concentration of 1 × 10 6 CFU / g. The green tea seed extract was added to each concentration, and the time course was observed from 1 to 28 days. Due to the effectiveness of the buoyant force according to the CTFA standard, the number of microorganisms should be reduced by 99.9% or more within 7 days of inoculation, no proliferation during the test period, the number of microorganisms should be decreased by 90% or more within 7 days of inoculation, The number of microorganisms must be reduced continuously.
녹차씨 60% 에탄올 추출물을 화장품 적용 결과, 상기 [도 5]서 나타내는 바와 같이 0.1% 녹차씨 추출물 적용 시, 21일차에 효모가 96% 사멸하였고, 28일차에 98.8% 사멸하였다. 이는 합성방부제인 메틸파라벤처럼 강한 방부 활성은 아니지만 천연 식물추출물로서는 매우 우수한 방부 활성을 나타낸다. As shown in Fig. 5, when applying 0.1% green tea seed extract, 96% of yeast was killed on day 21 and 98.8% was killed on day 28 as a result of application of 60% ethanol extract of green tea seedlings. It is not a strong preservative activity like methylparaben which is a synthetic preservative, but it exhibits excellent preservative activity as a natural plant extract.
Claims (8)
상기 녹차씨 조성물은 분쇄한 녹차씨를 5~80% 에탄올 또는 물로 5~24시간 동안 실온에서 추출한 후 여과지로 거른 다음 농축하여 항진균활성과 항암활성이 우수한 사포닌인 assamsaponin C, assamsaponin D, theasaponin E1 중 하나 또는 둘 이상을 포함하는 것을 특징으로 하는 녹차씨 조성물
A green tea seed composition comprising saponins having antifungal activity and anticancer activity,
The green tea seed composition was prepared by extracting ground green tea seeds with 5 to 80% ethanol or water at room temperature for 5 to 24 hours, filtering with a filter paper, and then concentrating to obtain saponins such as assamsaponin C, assamsaponin D and theasaponin E1 Or two or more of the green tea seed compositions
상기 녹차씨 조성물은 분쇄한 녹차씨를 100% 에탄올, 80% 에탄올, 60% 에탄올, 40% 에탄올, 20% 에탄올 및 물로 각각, 25℃에서 16시간 동안 추출한 후 여과하고 감압 농축하는 것을 특징으로 하는 녹차씨 조성물
The method according to claim 1,
The green tea seed composition is prepared by extracting crushed green tea seeds at 25 ° C for 16 hours with 100% ethanol, 80% ethanol, 60% ethanol, 40% ethanol, 20% ethanol and water, Seed composition
상기 녹차씨 조성물은 효모균인 칸디다(Candida), 자이고사카로마이세스(Zygosaccharomyces) 및 사카로마이세스(Saccharomyces)에 대해 항균 활성을 가지는 것을 특징으로 하는 녹차씨 조성물
The method according to claim 1,
Wherein the green tea seed composition has antimicrobial activity against Candida , Zygosaccharomyces, and Saccharomyces , which are yeasts ,
상기 녹차씨 조성물은 대식세포인 RAW 264.7 cell line(Mouse leukaemic monocyte macrophage cell line)에 대한 항암 활성을 가지는 것을 특징으로 하는 녹차씨 조성물
The method according to claim 1,
Wherein the green tea seed composition has an anticancer activity against a macrophage RAW 264.7 cell line (mouse leukemic monocyte macrophage cell line)
상기 녹차씨 조성물은 식품, 화장품, 생활용품에 포함되어 방부력을 가지게 하는 것을 특징으로 하는 녹차씨 조성물
5. The method according to any one of claims 1 to 4,
Wherein the green tea seed composition is contained in foods, cosmetics, household products, and has a buoyant power.
상기 녹차씨 조성물은 건강기능성식품에 포함되는 것을 특징으로 하는 녹차씨 조성물
5. The method according to any one of claims 1 to 4,
Wherein the green tea seed composition is contained in a health functional food
상기 녹차씨를 분쇄하는 단계; 및
상기 분쇄된 녹차씨를 5~80% 에탄올 또는 물로 5~24시간 동안 실온에서 추출한 후 여과지로 거른 다음 농축하여 항진균활성과 항암활성이 우수한 사포닌인 assamsaponin C, assamsaponin D, theasaponin E1 중 하나 또는 둘 이상을 포함하는 것을 특징으로 하는 녹차씨 조성물의 제조방법.
A method for preparing a green tea seed composition comprising saponins having antifungal activity and anticancer activity,
Crushing the green tea seeds; And
The ground green tea seeds were extracted with 5 to 80% ethanol or water at room temperature for 5 to 24 hours, filtered through filter paper, and concentrated to obtain one or more of saponins C, assamsaponin D, and theasaponin E1, which are excellent antifungal and anti- ≪ RTI ID = 0.0 > 1, < / RTI >
상기 녹차씨 조성물의 제조방법은 분쇄한 녹차씨를 100% 에탄올, 80% 에탄올, 60% 에탄올, 40% 에탄올, 20% 에탄올 및 물로 각각 25℃에서 16시간 동안 추출한 후 여과하고 감압 농축하는 것을 특징으로 하는 녹차씨 조성물의 제조방법
8. The method of claim 7,
The green tea seed composition is prepared by extracting crushed green tea seeds at 25 ° C for 16 hours with 100% ethanol, 80% ethanol, 60% ethanol, 40% ethanol, 20% ethanol and water, Of green tea seed composition
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| KR102136422B1 (en) | 2018-10-02 | 2020-07-21 | 전남대학교 산학협력단 | Antimicrobial composition for poultry comprising green tea saponin |
| KR20210100383A (en) | 2020-02-06 | 2021-08-17 | (주)정옥 | Green tea extracts for inhibition of dexamethasone-induced atrophy |
| KR20220078154A (en) * | 2020-12-03 | 2022-06-10 | 주식회사 자연과 미래 | Control compositions for crop pests capable of water and soil treatment And Methods for preparing the same |
| KR102540101B1 (en) | 2020-12-03 | 2023-06-05 | 주식회사 자연과 미래 | Control compositions for crop pests capable of water and soil treatment And Methods for preparing the same |
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