• 제목/요약/키워드: catechin compound

검색결과 99건 처리시간 0.031초

산겨릅나무 줄기추출물의 생리활성 및 유효성분 분리 (Biological Activities and Bioactive Compounds in the Extract of Acer tegmentosum Maxim. Stem)

  • 홍보경;엄석현;이찬옥;이지원;정종현;김재광;조동하;유창연;권용수;김명조
    • 한국약용작물학회지
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    • 제15권4호
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    • pp.296-303
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    • 2007
  • 본 연구에서는 소종과 외상출혈 치료에 사용되며, 주로 간암, 간경화 등의 간 질환 치료제로 사용되어 온 산겨릅나무 추출물에서 식품 및 음료 등과 같은 기능성 식품으로서의 다양한 산업적 응용분야에 널리 응용될 수 있는 기초연구의 일환으로 산겨릅나무 추출물을 이용하여 항산화 활성, 항지질과 산화 활성, 항미생물 활성, 항보체 활성을 실험하였으며, 또한 유용한 생리활성 성분을 분리, 동정하고자 하였다. 그 결과 산겨릅나무 추출물은 DPPH free radical 소거법에 의한 항산화 활성 실험에서는 ehtyl acetate 분획 ($RC_{50}= 3.15\;{\mu}g/m{\ell}$), butanol 분획 ($RC_{50}= 5.17\;{\mu}g/m{\ell}$)에서 강한 항산화 활성을 보였다. 또한 분리된 2개의 화합물도 대조군인 ${\alpha}-tocopherol$ 이나 BHA보다 유사하거나 강한 항산화 활성을 나타냈다. linoleic acid에 대한 항지질과산화 활성 실험은 15일 째에 물층을 제외한 추출물, 분획물 및 화합물에서 높은 활성을 나타냈으며 특히 화합물 2 (85%)는 항산화 물질로 알려진 catechin (85%)과 유사한 활성을 나타내었다. 박테리아에 대한 향균실험은 Staphylococus aureus 에서만 활성을 보이지 않았을 뿐 다른 피검균에서는 높은 활성을 보였다. 하지만 대부분의 피검균에 대하여 강한 활성을 보인 ethyl acetate 분획에서 분리된 화합물 1, 2는 모든 피검균에 대해 활성을 보이지 않았다. 다만 fungal strain인 Candida albicands에 대해 각각 $250\;{\mu}g/m{\ell}$. $500\;{\mu}g/m{\ell}$의 생육 억제 농도를 나타내었다. 보체계 활성화능을 측정한 결과 물 층 24%를 제외한 다른 분획물은 10% 이하의 낮은 억제효과를 보이거나 활성이 나타나지 않았다. 산겨릅나무 ethyl acetate 분획을 silica gel이 충전된 grass open column에 넣은 후, toluene, acetone, methanol의 혼합용매로 순차용출 (stepwise)시킨 후, ODS와 silica gel을 이용하여 column chromatography를 실시함으로서 2종의 단일 물질을 얻었다. 이 화합물은 $^lH-$$^{13}C-NMR$, IR, UV, EI/FAB-Mass spectrum을 이용하여 기기분석한 결과 compound 1은 catechin으로, compound 2는 ${\rho}-Hydroxyphenethyl$ alcohol 1-O-{\beta}-_D-(6'-O-galloyl)-glucopyranoside$로 동정되었으며, 특히 compound 2의 경우 산겨릅나무에서 처음 분리되었다. 위 결과 산겨릅나무 추출물은 항산화 활성, 항지질과산화 활성, 항미생물 활성이 우수하였다. 또한 산겨릅나무 추출물을 이용한다면 식품 및 음료 등과 같은 기능성 식품으로서의 다양한 산업적 응용분야에 널리 응용될 수 있으리라 사례된다.

쉬땅나무(Sorbaria sorbifolia var. stellipila MAX.) 열매의 항산화 활성 성분 (Antioxidative Constituents from Fruit of Sorbaria sorbifolia var. stellipila MAX.)

  • 박종혁;권진아;양윤정;한효상;한민우;이영일;김인수;이종일;강세찬
    • 한국자원식물학회지
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    • 제24권4호
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    • pp.337-342
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    • 2011
  • 합성항산화제의 독성과 부작용으로 인한 천연물유래 항산화제에 대한 관심과 연구개발이 활발한 가운데 추출물 단계에서 ORAC assay를 통하여 우수한 항산화 활성을 가지는 쉬땅나무(Sorbaria sorbfolia var. stellipila Max.) 열매의 생물학적 생리활성 성분을 분리, 동정하기 위하여 국내에 자생하는 쉬땅나무의 열매를 채집하여 80% MeOH로 추출한 후 일반적인 용매분획법에 의해 분획한 분획물과 추출물을 대상으로 ORAC assay를 실시한 결과 80% MeOH추출물과 EtOAc, n-BuOH분획에서 천연항산화제인 trolox보다 우수한 활성이 나타났으며, 이중 가장 우수한 활성을 나타낸 EtOAc 분획물로 부터 각종 chromatography 기법을 통하여 분리, 정제한 결과 flavonoid계열의 화합물인 catechin을 단리 하였다. 단리 되어진 catechin은 쉬땅나무의 열매에서는 처음으로 본 연구에서 보고되는 성분으로 ORAC assay에서 대조군인 trolox에 비해 높진 않지만 유사한 활성이 나타나, vitamine E와 유사한 항산화 활성을 나타내는 것으로 보여지며, 따라서, 이 성분 외에 다양한 항산화 활성 성분들의 복합작용으로 인하여 쉬땅나무열매 추출물 및 분획물이 vitamine E에 비하여 3배 이상의 높은 항산화 활성이 나타나고 있음을 시사하는 바이다. 현재까지 쉬땅나무에 대한 식물학적 성분연구 및 유효활성 성분연구가 다른 천연물에 비하여 상대적으로 활발하게 이루어지지 않았으나, flavonoid계 화합물이 TLC확인 시험을 통하여 확인한 바 다양하게 존재하고 있어, 향후 이와 유사한 다양한 flavonoid계열의 화합물을 분리하여, 우수한 항산화 활성을 갖는 천연물의약품의 기초자료 제공 등 항산화 성분연구에 많은 기여를 할 수 있을 것으로 판단된다.

주목열매 추출물 구조분석 (Structure Determination of the Extractives from the Taxus Cuspidata Fruits)

  • 박세영;최인규;배영수
    • Journal of the Korean Wood Science and Technology
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    • 제41권6호
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    • pp.566-575
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    • 2013
  • 주목열매에서 분리한 과육과 씨를 95% EtOH 용액을 사용하여 각각 1.15 kg과 0.94 kg을 유리 용기에 침지하여 추출하고, 농축된 추출용액을 용매의 극성에 따라 n-hexane, dichloromethane, ethyl acetate 및 수용성으로 순차 분획한 후, 동결건조하였다. 혼합물로부터 순수한 화합물을 분리하기 위하여 ethyl acetate 및 수용성 분획에 대하여 Sephadex-LH 20 칼럼크로마토그래피를 실시하였다. 단리된 화합물들의 구조는 flavan 화합물의 경우 $^1H$-NMR, $^{13}C$-NMR 및 EI-MS 스펙트럼을 측정하였으며, 탄수화물은 보다 정확한 구조를 결정하기 위해 COSY, HSQC와 같은 2-D NMR과 LC/MS 스펙트럼을 이용하여 구조를 결정하였다. 또한 구성당 분석을 위해 acid hydrolysis, permethylation을 실시하여 구성당의 성분과 결합위치를 확인하였다. 위의 실험을 통하여 (+)-catechin (1), (-)-epicatechin (2), (+)-gallocatechin (3), (-)-epigallocatechin(4) 및 ${\beta}$-D-fructofuranose-($2{\rightarrow}4$)-O-${\beta}$-D-glucopyranose($1{\rightarrow}4$)-O-${\alpha}$-D-glucopyranose-($1{\rightarrow}2$)-O-${\beta}$-D-fructofuranose (5)의 구조를 결정하였다.

작약근(芍藥根) 생육년수(生育年數)에 따른 성분(成分) 함양(含量) 변화(變化) (The Changes of Bioactive Component Concentrations in Different Aged-Peony (Paeonia lactiflora Pall.) Root)

  • 정명근;강광희;곽용호
    • 한국약용작물학회지
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    • 제7권3호
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    • pp.193-199
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    • 1999
  • 한국산 재배작약 중 "의성 작약" (Paeonia lactiflora Pall.)을 대상으로 작약근의 주 활성물질로 평가되는 paeonilforin, albiflorin 및 5종의 phenolic compounds 함량의 생육년수별 변화양상을 조사한 결과를 요약하면 다음과 같다. 생육년수별 의성작약의 생근굵기는 1년생이 5.3mm, 2년생이 10.3mm, 3년생이 15.6, 4년생이 19.1mm로 뚜렷한 차이를 나타내어 생육년수에 따라 일정한 경향으로 생근의 굵기가 증가 하였다. 생육년수별 paeoniflorin, albifiorin, (+)-catechin 및 benzoic acid의 함량은 가는 뿌리인 1년생의 함량이 높았고, gallic acid, (+)-taxifo.in 3-O-${\beta}-D$ glucoside 및 (-) -epicatechin 함량은 굵은 뿌리인 $3{\sim}4$년생의 함량이 더 높았다. 의성작약에 함유된활성 물질 증 (-) -epicatechin을 제외한 paeoniflorin, albiflorin 및 phenolic compounds의 각 함랑은 껍질이 있는 유피근이 껍질을 제거한 거피근보다 전반적으로 높은 양상을 나타내었다.

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Effects of quercetin derivatives from mulberry leaves: Improved gene expression related hepatic lipid and glucose metabolism in short-term high-fat fed mice

  • Sun, Xufeng;Yamasaki, Masayuki;Katsube, Takuya;Shiwaku, Kuninori
    • Nutrition Research and Practice
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    • 제9권2호
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    • pp.137-143
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    • 2015
  • BACKGROUND/OBJECTIVES: Mulberry leaves contain quercetin derivatives, which have the effects of reducing obesity and improving lipid and glucose metabolism in mice with obesity. It is not clear whether or not mulberry leaves can directly affect metabolic disorders, in the presence of obesity, because of the interaction between obesity and metabolic disorders. The aim of the current study was to assess the direct action of quercetin derivatives on metabolic disorders in non-obese conditions in short-term high-fat diet fed mice. MATERIALS/METHODS: C57BL/6N mice were fed a high-fat diet, supplemented with either 0% (control), 1%, or 3% mulberry leaf powder (Mul) or 1% catechin powder for five days. Anthropometric parameters and blood biochemistry were determined, and hepatic gene expression associated with lipid and glucose metabolism was analyzed. RESULTS: Body and white fat weights did not differ among the four groups. Plasma triglycerides, total cholesterol, and free fatty acids in the 1%, 3% Mul and catechin groups did not differ significantly from those of the controls, however, plasma glucose and 8-isoprostane levels were significantly reduced. Liver gene expression of gp91phox, a main component of NADPH oxidase, was significantly down-regulated, and PPAR-${\alpha}$, related to ${\beta}$-oxidation, was significantly up-regulated. FAS and GPAT, involved in lipid metabolism, were significantly down-regulated, and Ehhadh was significantly up-regulated. Glucose-metabolism related genes, L-PK and G6Pase, were significantly down-regulated, while GK was significantly up-regulated in the two Mul groups compared to the control group. CONCLUSIONS: Our results suggest that the Mul quercetin derivatives can directly improve lipid and glucose metabolism by reducing oxidative stress and enhancing ${\beta}$-oxidation. The 1% Mul and 1% catechin groups had similar levels of polyphenol compound intake ($0.4{\times}10^{-5}$ vs $0.4{\times}10^{-5}$ mole/5 days) and exhibited similar effects, but neither showed dose-dependent effects on lipid and glucose metabolism or oxidative stress.

In vitro and in vivo antidiarrhoeal activity of epigallocatechin 3-gallate: a major catechin isolated from indian green tea

  • Bandyopadhyay, Durba;Dutta, Pradeep Kumar;Dastidar, Sujata G;Chatterjee, Tapan Kumar
    • Advances in Traditional Medicine
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    • 제8권2호
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    • pp.171-177
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    • 2008
  • Epigallocatechin 3-gallate (EGCG), one of the major catechins of tea, was isolated from the decaffeinated, crude methanolic extract of Indian green tea (Camellia sinensis L. O. Kuntze) using chromatographic techniques. EGCG was then screened for antidiarrhoeal activity against 30 strains (clinical isolates) of V. cholerae, which is a well known Gram negative bacillus functioning as the pathogen of cholera. V. cholerae strains like V. cholerae 69, 71, 83, 214, 978, 1021, 1315, 1347, 1348, 569B and ATCC 14033 were inhibited by EGCG at a concentration of $25\;{\mu}g/ml$ whereas V. cholerae 10, 522, 976 were even more sensitive, being inhibited at $10\;{\mu}g/ml$ level. However, V. cholerae DN 16, DN 26, 30, 42, 56, 58, 113, 117, 564, 593, 972 and ATCC 14035 were inhibited at $50\;{\mu}g/ml$ level of EGCG. Only four strains were inhibited at $100\;{\mu}g/ml$. In this study the isolated compound was found to be bacteriostatic in its mechanism of action. In the in vivo experiment using the rabbit ileal loop model two different dosages of EGCG ($500\;{\mu}g/ml$ and $1,000\;{\mu}g/ml$) were able to protect the animals when they were challenged with V. cholerae 569B in the ileum.

Cytotoxic Phenolic Constituents of Acer tegmentosum Maxim

  • Park, Ki-Myun;Yang, Min-Cheol;Lee, Kyu-Ha;Kim, Kyung-Ran;Choi, Sang-Un;Lee, Kang-Ro
    • Archives of Pharmacal Research
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    • 제29권12호
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    • pp.1086-1090
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    • 2006
  • The chromatographic separation of the MeOH extract from the twigs of Acer tegmentosum led to the isolation of ten phenolic compounds. The structures of these compounds were determined using spectroscopic methods as 3,7,3',4'-tetramethyl-quercetin (1), 5,3'-dihydroxy-3,7,4'-trimethoxy flavone (2), 2,6-dimethoxy-p-hydroquinone (3), (-)-catechin (4), morin-3-O-${\alpha}$-L-lyxoside (5), p-hydroxy phenylethyl-O-${\beta}$-D-glucopyranoside (6), 3,5-dimethoxy-4-hydroxy phenyl-1-O-${\beta}$-D-glucoside (7), fraxin (8), 3,5-dimethoxy-benzyl alcohol 4-O-${\beta}$-D-glucopyranoside (9) and 4-(2,3-dihydroxy propyl)-2,6-dimethoxy phenyl ${\beta}$-D-glucopyranoside (10). The compounds were examined for their cytotoxic activity against five cancer cell lines. Compound 3 exhibited good cytotoxic activity against five human cancer cell lines with $ED_{50}$ values ranging from $1.32\;to\;3.85\;{\mu}M$.

Free Radica1 Scavenging and Hepatoprotective Constituents from the Leaves of Juglans sinensis

  • An, Ren-Bo;Kim, Hyun-Chul;Tian, Yu-Hua;Kim, Youn-Chul
    • Archives of Pharmacal Research
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    • 제28권5호
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    • pp.529-533
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    • 2005
  • In the course of searching for hepatoprotective agents from natural products, six compounds were isolated from the MeOH extract of the leaves of Juglans sinensis, as guid ed by their DPPH free radical scavenging activity. The structures were determined as juglanoside B (1), quercetin 3-O-${\alpha}$-L-arabinofuranoside (avicularin, 2), quercetin 3-O-${\alpha}$-L-arabinopyranoside (guaijaverin,3), quercetin 3-O-${\alpha}$-L-rhamnopyranoside (quercitrin,4), (+)-catechin (5) and quercetin 3-O-${\beta}$- D-galactopyranoside (hyperin,6). Compounds 2-6 showed significant DPPH free radical scavenging effects. An evaluation for the hepatoprotective activity of the isolated compounds on drug-induced cytotoxicity was conducted, and compounds 1, 2, and 5 showed protective effects against nitrofurantoin-induced cytotoxicity, and compound 5 also exhibited a moderate protective effect on amiodarone-induced cytotoxicity in Hep G2 cells.

Identification of Antioxidative Constituents from Polygonum aviculare using LC-MS Coupled with DPPH Assay

  • Shin, Hyeji;Chung, Hayeon;Park, Byoungduck;Lee, Ki Yong
    • Natural Product Sciences
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    • 제22권1호
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    • pp.64-69
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    • 2016
  • A method for simultaneously identifying antioxidative compounds was developed using time-based LC-MS coupled with DPPH assay regardless of the time consuming process. The methanolic extract of Polygonum aviculare (Polygonaceae) showed significant DPPH radical scavenging activity. Time-based DPPH assay for simultaneous identification of active compounds from the extracts of P. aviculare was used. Major peaks of ethyl acetate fraction of P. aviculare showed high DPPH radical scavenging activity. A simple phenolic compound (1) and six flavonoids (2-7) were isolated from the ethyl acetate fraction of P. aviculare by silica gel and sephadex LH-20 column chromatography. The structures of seven compounds were determined to be protocatechuic acid (1), catechin (2), myricitrin (3), epicatechin-3-O-gallate (4), avicularin (5), quercitrin (6), and juglanin (7) based on the analysis of the $^1H$-NMR, $^{13}C$-NMR and ESI-MS data. All compounds exhibited significant antioxidant activity on DPPH assay and active compounds were well correlated with predicted one.

AMPK 활성화를 통한 (-)-Epigallocatechin-3-gallate의 지방세포분화 억제 효과 (Inhibitory Effects of (-)-Epigallocatechin-3-gallate on Adipogenesis via AMPK Activation in 3T3-L1 Cells)

  • 김영화
    • 한국식품영양학회지
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    • 제30권5호
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    • pp.1035-1041
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    • 2017
  • (-)-Epigallocatechin-3-gallate (EGCG) is a major catechin found in green tea. It is reported that EGCG possesses various health benefits including anti-cancer, antioxidant, anti-diabetes, and anti-obesity. The objective of this study was to investigate the effects of EGCG on adipogenesis via activation of AMP-activated protein kinase (AMPK) pathway in 3T3-L1 preadipocytes. In order to determine the effects of EGCG on adipogenesis, preadipocyte differentiation was induced in the presence or absence of EGCG ($0{\sim}100{\mu}M$) for a period of 6 days. EGCG significantly inhibited fat accumulation and suppressed the expression of adipogenic specific proteins including peroxisome proliferator-activated receptor (PPAR)-${\gamma}$. Also, EGCG markedly increased the activation of AMPK and acetyl-CoA carboxylase (ACC) and the production of intracellular reactive oxygen species (ROS). However, any pretreatment with a specific AMPK inhibitor, compound C, abolished the inhibitory effects of the EGCG on $PPAR{\gamma}$ expression. This study suggests that EGCG has anti-adipogenic effects through modulation of the AMPK signaling pathway and therefore, may be a promising antiobesity agent.