• Plant Biotechnology Reports
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• v.5 no.1
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• pp.79-88
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• 2011

Vitis vinifera cv. Koshu is a traditional grape cultivar that has been grown for centuries in Japan. The Koshu grape has pink-colored skin and Koshu wines have slight astringency. We demonstrated for the first time the characterization of hydroxycinnamic acids, flavan-3-ols, and flavonoids in Koshu grape using high-performance liquid chromatography and liquid chromatography-mass spectrometry. The gross weight of phenolic compounds excluding anthocyanins and proanthocyanidins in Koshu grape at harvest was higher than those in Sauvignon Blanc, Chardonnay, and Merlot grapes. In addition, hydroxycinnamic acid and monomeric flavonol contents in Koshu grape were also higher than those in the other grape cultivars. Transcription analysis of cinnamic acid 4-hydroxylase, p-coumarate 3-hydroxylase, caffeate methyltransferase, and flavonol synthase genes indicated high accumulation of hydroxycinnamic acids and flavonols in Koshu grape skin compared with the other cultivars. These findings obtained by chemical and molecular approaches partially explained the phenolic characteristics and the peculiar astringency of Koshu grape.

• Korean Journal of Medicinal Crop Science
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• v.5 no.4
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• pp.302-306
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• 1997

One flavan 3-ol derivative was isolated from the stem of Acer mono Max, along with two known coumarins. On the basis of spectroscopic evidence, the structures of these compounds were established as (-) - epicatechin, scopoletin and isoscopoletin. Antioxidative activity of (-) - epicatechin was examined by the DPPH free radical scavenging method. Antioxidative activity of (-) - epicatechin $(RC_{50}\;:\;7.5\;{mu}g)$ was more greater than those of ${\alpha}-tocopherol\;(RC_{50}\;:\;12\;{mu}g)$ and $BHA\;(RC_{50}\;:\;14\;{mu}g)$.

• YAKHAK HOEJI
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• v.41 no.4
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• pp.439-443
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• 1997

From the root bark of Broussonetia kazinoki (Moraceae) two antioxidant components were identified. Their structures were determined as kazinol A (1) and kazinol E (2) (is oprenylated flavan and isoprenylated 1,3-diphenyl propan derivatives) by comparing NMR data with those of the reported compounds from relative plants. The antioxidant activity of 1 and 2 were monitored by the method of DPPH radical scavenging activity, whose $SC_{50}$ values were $41.4{\mu}M\;and\;33.4{\mu}M$, respectively. These compounds also exhibited inhibitory activity against tyrosinase, which is the sole key enzyme for the melanin biosynthesis and play a role in conversion of tyrosine to dopa, and dopa to dopaquinone. The antioxidant effect and the suppression of melanin biosynthesis are useful for anti-aging, increasing vitality in the incidence of major degenerative diseases, and cosmetic products in relation to hyperpigmentation.

• Proceedings of the Korean Society of Crop Science Conference
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• 2022.10a
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• pp.27-27
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• 2022

(-)-Epicatechin (EC), a primary form of flavan-3ol and a building block of proanthocyanidins, has health benefits as it is a potent antioxidant. So far, no quantitative trait loci (QTLs) associated with EC have yet been identified in soybean. In this study, QTLs for EC and hilum color were identified in recombinant inbred lines (RILs) derived from the varieties Jinpung and IT109098 using high-resolution single nucleotide polymorphism linkage mapping. This revealed two major QTLs for EC content, qEC06 and qEC08. qEC06 spanned the T Locus encoding flavonoid 3'-hydroxylase. qEC08, located near the I locus on Chr08, was also a major QTL for hilum color; however, allelic stacking of qEC08 and I revealed no relationship between I and EC content. RILs with IT 109098 alleles at both qEC06 and qEC08 had higher EC content than other lines. These results will enable the production of soybean varieties with high EC content via marker-assisted selection.

• Archives of Pharmacal Research
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• v.16 no.1
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• pp.18-24
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• 1993

In this inverstigation, the various flavonoid aglycones were evaluated for their inhibitory activities against croton-oil or arachidonic acid induced mouse ear edema by oral or topical administration. The compounds tested were thirteen derivatives of flavan-3-ol(catechin and epicatechin), flavanone (flavanone and naringenin), flavone (flavone, chrysin and apigenin), flavonol(favonol, galangin, quercetin and morin) and isoflavone (biochanin A and 2-carbethoxy-5,7-dihydroxy-4'-methoxyisoflavone), along with hydrocortisone, indomethacin, 4-bormophenacyl bromide, nordihydroguaiaretic acid and phenidone as positive controls. A(isoflavone) were found to show broad inhibitoty activities (14-52%) against croton-oil or arachidonic acid induced ear edema by oral or topical application at the dose of 2 mg/mouse, although they showed less activity than hydrocortisone (26-88%) or indomethacin (36-80%). Flavonoid agtlycones tested showed higher activity when aplied topically than by the oral administration. It was also found that they inhibited arachidonic acid induced edema more profoundly than croton-oil induced edema by topical application. In arachidonic acid induced edema when applied topically, flavone derivatives such as flavone, chrysin and apigenin were revealed to be the good inhibitory agents in addition to flavonols and isoflavones. When quercetin and biochanin. A were selected for evaluating in carrageenan induced rat pleurisy and biochanin both flavonoids showed antiinflammatory activity at the dose of 70 mg/kg by the oral adminis-tration. All of these results revealed that flavonoid aglycones, especially 5,7-dihydroxy-flavonols having hydroxyl group(s) in B-ring and biochanin A (isoflavone) possessed in vivo antiinflammatory activity.

• Proceedings of the Korean Society of Postharvest Science and Technology of Agricultural Products Conference
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• 2002.04a
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• pp.29-40
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• 2002

감잎으로부터 통풍치료, 미백효과, 고혈압 억제효과의 개발목적으로 9종의 flavan-3-ol 화합물을 분리하였고 기기분석에 의해 화학구조를 자혔다. 각 화합물은 (+)-catechin (+)-gallocatechin procyanidinB-l, pyrocyanidin C-1, prodelphinidin B-3, gallocatechin-(4$\alpha$$\longrightarrow$8)-catechin과 감나무 잎에서 새로운물질인pocyanidin B-7-3-0-gallate, procyanidin C-1-3'-3" -3.'S _0-trigallate, (-)-epigallocatechin-(4 $\beta$ -18)-epigallocatechin-(4$\beta$-'8)-catechin 3종류를 발견하였다. 감잎으로부터 순수 분리한 polyphenol류의ACE 저해활성측정을 실험한 결과 pocyanidin B-7-3-0-gallate는 100rM농도에서 94%의 저해효과를 나타내었으며 epigallocatechin-(4$\beta$$\longrightarrow$8)-epigallo-catechin-(4$\beta$$\longrightarrow$8)-catechia procyanidin C-1-3'-3" -3f'.-0-trigallate는 각각 90.69, 80.90% 저해를 하였다. Xanthine oxidase 저해활성측정을 조사한 결과pocyanidin B-7-3-0-galtate와 pocyanidin C-1-3'-3" -3/'S _0-trigallate 즉, gallate가 붙은 호합물에서100rM의 농도에서 66%와 63%의 강한 저해효과를 나타났다. Tyrosinase 저해활성을 측정한 결과는pocyanidin C-1-3'-3" -3.'S _0-trigallate는 100rM에서 70%의 강한 저해효과를 나타냈으며,epigallocatechin-(4$\beta$$\longrightarrow$8)-epigallo-catechin-(4$\beta$$\longrightarrow$8)-catechin는 51%의 저해효과를 나타내었다. 산업적응용을 위해 분획한 폴리페놀군은 미백효과 검증실험인 tyrosinase 저해율 측정평가에서 폴리페놀 함량이 가장 높은 Fraction 111의 경우 Sooppm에서 74.2%의 높은 저해율을 나타내었다. 항산화력 실험에서는500pw1이상에서 강한 활성능을 보인 SOD 유사활성능을 제외한 나머지 DPPH와 xanthine oxidase 저해효과에서는 Fraction II와III 모두가50ppm이상에서 80% 이상의 높은 유리라디칼 소거능력을 나타내었다. 그리고 각 Fraction별 항균력 측정 결과 Fraction 르와 111이 우수하게 나타났고 항균활성은 그람음성균보다 그람양성균에서 효과적이었으며, 농도별 항균력시험 결과 농도가 증가할수록 비례하여 저해율도 증가함을 알 수 있었다. 첨가농도를 달리하여 미생물의 생육도를 측정한 결과, fraction II磎꼭\ulcorner경우 그람양성균에 대해 500 ppm 이상에서 뚜렷한 증식억제효과를 나타내었다.서 뚜렷한 증식억제효과를 나타내었다.

• Applied Biological Chemistry
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• v.39 no.6
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• pp.477-481
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• 1996

It has been shown that tannins have adverse effects on growth of animals and feed utilization. Tannins are usually classified into hydrolyzable and condensed types but the adverse effects are more marked in condensed tannin in hydrolyzable tannin. Furthermore, the principle condensed tannins found in banana fruits are pro types by the polymerization of flavan-3, 4-diols either alone or in combination with other flavonoids such as catechins. Tannin of the investigated banana(Banana; Musa sapientum LINN)fruits was fractionated into four or five molecular forms, according to the degree of polymerization by chromatography on a column of Sephadex LH-20. The protein-precitating capacity of the fraction noted tannins increased in degree polymerzation. The inhibitory effect of tannins on trypsin(EC 3. 4. 21. 4), ${\alpha}-amylase$(EC 3. 2. 1. 1) and lipase(EC 3. 1. 1. 3) activities in vitro also increased with the incraesed in degree of polymerization.

• Journal of the Korean Society of Food Science and Nutrition
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• v.32 no.1
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• pp.109-114
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• 2003

Antimicrobial activities of grape seed ethanol extract and its serial solvent fractions were investigated against various food poisoning microorganisms. The grape seed ethanol extract showed dose dependant antimicrobial activity against Bacillus subtilis ATCC 9372 or Staphylococcus aureus ATCC 6538, whereas had limited effect on Pseudomonas aeruginosa IFO 3080, Salmonella enteritidis IFO 3313 and Escherichia coli ATCC 25922. Ethylacetate and butanol fractions ameng the serial solvent fractions of grape seed ethanol extract contained the catechin at the levels of 35.7 mg/g and 20.2 mg/g, respectively. Nevertheless, the butanol fraction of grape seed ethanol extract showed intense antimicrobial activity compared with the ethylacetate fraction on all microorganisms tested. It was found that the butanol fraction was mainly composed of oligomeric or polymeric polyphenols such as condensed tannins by the fractionation on C l8 cartridge according to the difference in the degree of polymerization. Therefore, it seems that the antimicrobial activity of grape seed ethanol extract is related to the degree of polymerization of proanthocyanidin as well as the total content of flavan-3-ol composing the proanthocyanidin.

• Fashion & Textile Research Journal
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• v.8 no.3
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• pp.343-348
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• 2006

This study aims to attain gray tone dyed goods by using tannin that is contained in green tea. Tannin is given general name of polyphenol, which has a characteristic that bonds with protein and it is used for food preservative that protects against bacteria, as well as its purpose of black tone dye for silk treatment that has been processed since its early ages. In particular, as tannin reacts with all kinds of metallic mordant and changes to various colors, when tannin acid is combined with iron, it becomes tannin steel and produces gray tone color. Tannin that is contained in green tea is condensed tannins and its structure does not hydrolyze, thus having flavan type structure. In order to find the suitable condition for processing tannin, UV-Vis part absorption spectrum of green tea tannin, dye ability based on temperature and time, reflection rate based on concentration, color changes based on acid treatment and alkali treatment, changes on surface based on concentration or metal mordant condition, and lightfastness were measured. Maximum absorption wavelength (${\lambda}_{max}$) of green tea tannin was at around 273nm, while strong absorption was also observed at below 350 nm. Dye ability of green tea tannin is done more easily on silk rather than cellulose fibers such as cotton, while the optimum condition for dyeing was observed to be at $60^{\circ}C$, for 20 minutes. As a result of acid treatment, the color of dye material consisted highly of gray tones and showed overall gray tone with the combined color of yellow and red after the alkali treatment. While it was observed that as dye concentration and metal mordant concentration increased, the color changed at counter-clockwise direction on the Y-scale of Munsell's scale of colors. Additionally, lightfastness was more on a normal fading.

• Archives of Pharmacal Research
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• v.27 no.10
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• pp.1043-1047
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• 2004

Thirteen compounds were isolated from the $CH_2Cl_2$ fraction of Machilus thunbergii as phospholipase $C{\Upsilon}1\;(PLC{\Upsilon}1)$ inhibitors. These compounds were identified as nine lignans, two neolignans, and two flavans by spectroscopic analysis. Of these, 5,7-di-O-methyl-3',4'-methylenated (-)-epicatechin (12) and 5,7,3'-tri-O-methyl (-)-epicatechin (13) have not been reported previously in this plant. In addition, seven compounds, machilin A (1), (-)-sesamin (3), machilin G (5), (+)-galbacin (9), licarin A (10), (-)-acuminatin (11) and compound 12 showed dose-dependent potent inhibitory activities against $PLC{\Upsilon}1$ in vitro with $IC_{50}$ values ranging from 8.8 to 26.0 ${\mu}M$. These lignans, neolignans, and flavans are presented as a new class of $PLC{\Upsilon}1$ inhibitors. The brief study of the structure activity relationship of these compounds suggested that the benzene ring with the methylene dioxy group is responsible for the expression of inhibitory activities against $PLC{\Upsilon}1$. Moreover, it is suggested that inhibition of $PLC{\Upsilon}1$ may be an important mechanism for an antiproliferative effect on the human cancer cells. Therefore, these inhibitors may be utilized as cancer chemotherapeutic and chemopreventive agents.