• 약학회지
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• 제43권4호
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• pp.516-525
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• 1999

Hedera rhombea (HR) has been used for treatments of hemorrage, chronic catarrh, jaundice, lithisis and convulsion. This study was done to isolate active compounds that have protective effect on liver damage. BuOH and EtOAc fractions of HR recovered serum glutamic pyruvic transaminase (GPT), glutamic oxaloacetic transaminase (GOT) and ${\gamma}-glutamyltranspeptidase$ (${\gamma}-GTP$) activities in CCl4 treated rats. We isolated 7 phenolic compounds from BuOH and EtOAc fractions, which were identified as 3-caffeoyl quinic acid, 3,4-di-O-caffeoyl quinic acid, 3,5-di-O-caffeoyl quinic acid, 4,5-di-O-caffeoyl quinic acid, caffeic acid, methyl 3,4-di-O-caffeoyl quinic acid and methyl 3,5-di-O-caffeoyl quinic acid by chemical and spectral analysis. These compounds reduced significantly serum GOT and GPT elevated by CCl4 treatment in rats, and 3-caffeoyl quinic acid, 3,5-di-O-caffeoyl quinic acid and caffeic acid also showed mild inhibitory activity against human immunodeficiency virus.

• 생약학회지
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• 제30권4호
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• pp.420-422
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• 1999

From the EtOAc fraction of Dipsacus asper, four compounds have been isolated. On the basis of spectral data, these compounds were identified as protocatechuic acid, caffeic acid, 3,4-di-O-caffeoyl quinic acid and methyl 3,4-di-O-caffeoyl quinate.

• 한국식품영양과학회지
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• 제46권6호
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• pp.759-764
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• 2017

당뇨합병증에 효과적인 천연물 유래의 신소재를 개발하기 위하여 본 연구를 수행하여 단풍취 70% 에탄올 추출물의 EtOAc 가용부로부터 최종당화산물 생성 억제능($IC_{50}=5.5{\pm}1.1{\mu}g/mL$)을 확인하였다. 활성을 나타내는 성분의 동정을 위하여 $C_{18}$겔 등을 활용한 칼럼크로마토그래피를 수행하여 4종의 dicaffeoylquinic acid 유도체 화합물을 분리하였고, 각 화합물의 화학구조는 NMR 스펙트럼 데이터 해석 및 표품과의 HPLC 직접 비교를 통하여 methyl 3,5-di-O-caffeoyl-epi-quinate(1), 3,5-di-O-caffeoyl-epi-quinic acid(2), 4,5-di-O-caffeoyl-quinic acid(3) 및 methyl 4,5-di-O-caffeoyl-quinate(4)로 동정하였다. 이들 화합물에 대해 최종당화산물 생성 억제능을 평가한 결과 4,5-di-O-caffeoyl-quinic acid(3)가 가장 강한 $0.4{\pm}0.1{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 3,5-di-O-caffeoyl-epi-quinic acid(2)가 $0.6{\pm}0.1{\mu}M$의 $IC_{50}$ 값을 나타내었다. 또한, 이들 물질에 대해 $ABTS^+$ 소거 활성을 평가하여 4,5-di-O-caffeoyl-quinic acid(3)가 가장 강한 라디칼 소거 활성인 $14.6{\pm}0.4{\mu}M$의 $IC_{50}$ 값을 나타내었으며, 구조 이성질체인 3,5-di-O-caffeoyl-epi-quinic acid(2)가 $18.8{\pm}0.4{\mu}M$의 $IC_{50}$ 값을 확인하였다. 단풍취에서 분리한 화합물의 활성은 caffeic acid의 결합방식 및 methyl화 여부에 따른 화합물의 구조에 따라 다름이 시사되었다. 향후 우수한 활성을 나타낸 이들 화합물의 in vivo 실험을 통한 활성기작의 검증이 필요하다고 생각된다. 또한, 추가적인 연구를 통하여 식의약 소재로 활용이 가능한 새로운 천연신소재 발굴을 위한 기초자료제공 및 당뇨합병증에 효과적인 천연 물질의 상업화를 위한 귀중한 자료로 활용할 수 있으리라 판단된다.

• 생약학회지
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• 제34권2호통권133호
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• pp.128-131
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• 2003

Four compounds were isolated from the roots of Dipsacus asper roots, and were identified as methyl 3,5-di-O-caffeoyl quinate, 3,5-di-O-caffeoyl quinic acid, sitosterol $3-O-{\beta}-D-Glucopyranoside$ and hederagenin $3-O-{\alpha}-L-arabinopyranoside$. Among the isolated compounds, methyl 3,5-di-O-caffeoyl quinate and 3,5-di-O-caffeoyl quinate acid have never been reported previously from this plant.

• 생약학회지
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• 제25권1호
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• pp.11-19
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• 1994

Gleditsia japonica var. koraiensis NAKAI(Leguminosae) is commonly distributed in Korea and has been used as a folk medicine in the treatment of bronchitis, neoplasm and blennorrhgia in the Orient. The aqueous acetone extract of the leaves of G. japonica was subjected to a combination of Sephadex LH-20, Cosmosil $75C_{18}-OPN$, TSK-gel Toyopearl HW 40F, Avicel cellulose, and MCI-gel CHP 20P chromatographies with various solvent systems. Twelve compounds were isolated and confirmed to be vitexin(1), isovitexin(2), orientin(3), isoorientin(4), 4-caffeoyl quinic acid(5), 5-caffeoyl quinic acid(6), 3, 5-dicaffeoyl quinic acid(7), 4, 5-dicaffeoyl quinic acid(8), caffeic acid(9), quercetin(10), isoquercitrin(11) and luteolin-7-O-glucoside(12), on the basis of chemical and spectroscopic evidences.

• 생약학회지
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• 제27권2호
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• pp.136-141
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• 1996

We have previously reported the isolation of nine hydrolisable tannins and five flavonoids from the aerial parts of Euphorbia ebracteolata. Further investigation about the same plant has led to the isolation of 5-O-caffeoyl quinic acid, kaempferol $3-O-(2'-O-galloyl-{\beta}-_D-glucoside)$ and euphorbin A.

• 약학회지
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• 제59권3호
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• pp.107-112
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• 2015

Blueberries (Ericaceae) are cultivated worldwide, and are used not only as foodstuff but also for relievement of eyestrain. Bluberry species representatively includes highbush blueberry (V. corymbosum L.), lowbush blueberry (V. angustifolium $A_{IT}$.), rabbiteye blueberry (V. ashei $R_{EADE}$), and bilberry blueberry (V. myrtillus L.). All of these species contain large amounts of phenolics and anthocyanins. In this regard, we isolated six compounds from Korea cultivated blueberry and identified as 3-O-caffeoylquinic acid (1), 5-O-caffeoylquinic acid (2), myricetin-3-O-${\beta}$-D-galactoside (3), quercetin-3-O-rutinoside (4), ethyl-3-O-caffeoylquinic acid ester (5), ethyl-5-O-caffeoyl quinic acid ester (6) by $^1H$-NMR, $^{13}C$-NMR and MS. Anti-oxidative activities of six compounds were verified by anti-oxidant assay such as DPPH, ABTS and Hypoxanthine/xanthine oxidase system. And then, anti-oxidant activities of Korea blueberry and Canadian were compared with each other. These results support that Korean blueberry has also the possibility to be potential supplementary material as healthy food like Canadian blueberry. Therefore, Korean blueberry can be used as a substitute of Canadian blueberry.

• Archives of Pharmacal Research
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• 제27권2호
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• pp.164-168
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• 2004

The chromatographic separation of the MeOH extract of the aerial parts of Solidago virga-aurea var. gigantea $M_{IQ}$ . (Compositae) led to the isolation of six terpenoids and four phenolic compounds, trans-phytol (1), ent-germacra-4(15),5,10(14 )-trien-1$\alpha$-ol (2), $\beta$-amyrin acetate (3), ent-germacra-4(15),5,10(14)-trien-1$\beta$-ol (4), $\beta$-dictyopterol (5), oleanolic acid (6), kaempferol (7), kaempferol-3-O-rutinoside (8), methyl 3,5-di-O-caffeoyl quinate (9), and 3,5-di-O-caffeoyl quinic acid (10). Their structures were established by chemical and spectroscopic methods. Compounds 4, 5, and 10 showed moderate cytotoxicity against five cultured human tumor cell lines in vitro with its E $D_{50}$ values ranging from 1.52∼18.57 $\mu\textrm{g}$/mL.L.

• Natural Product Sciences
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• 제25권1호
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• pp.64-71
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• 2019

The present study was conducted to investigate anti-nociceptive and anti-inflammatory effects of the leaves of Ilex latifolia Thunb (I. latifolia) in in vivo and in vitro. Writhing responses induced by acetic acid and formalin- and thermal stimuli (tail flick and hot plate tests)-induced pain responses for nociception were evaluated in mice. I. latifolia (50 - 200 mg/kg, p.o.) and ibuprofen (100 mg/kg, p.o.), a positive non-steroidal anti-inflammatory drug (NSAID), inhibited the acetic acid-induced writhing response and the second phase response (peripheral inflammatory response) in the formalin test, but did not protect against thermal nociception and the first phase response (central response) in the formalin test. These results show that I. latifolia has a significant anti-nociceptive effect that appears to be peripheral, but not central. Additionally, I. latifolia (50 and $100{\mu}g/mL$) and 3,5-di-caffeoyl quinic acid methyl ester ($5{\mu}M$) isolated from I. latifolia as an active compound significantly inhibited LPS-induced NO production and mRNA expression of the pro-inflammatory mediators, iNOS and COX-2, and the pro-inflammatory cytokines, IL-6 and $IL-1{\beta}$, in RAW 264.7 macrophages. These results suggest that I. latifolia can produce antinociceptive effects peripherally, but not centrally, via anti-inflammatory activity and supports a possible use of I. latifolia to treat pain and inflammation.

• Archives of Pharmacal Research
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• 제28권10호
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• pp.1122-1126
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• 2005

Tungtungmadic acid (3-caffeoyl-4-dihydrocaffeoyl quinic acid) is a new chlorogenic acid derivative that was isolated from the Salicomia herbacea. The structure of tungtungmadic acid was determined using chemical and spectral analysis. The antioxidant activity of tungtungmadic acid was evaluated using various antioxidant assays, including free radical scavenging, lipid peroxidation and hydroxyl radical-induced DNA strand breaks assays. Tungtungmadic acid ($IC_{50}\;=\;5.1\;{\mu}M\;and\;9.3\;{\mu}M$) was found to have higher antioxidant activity in the DPPH scavenging assay as well as in the iron-induced liver microsomal lipid peroxidation system. In addition, the tungtungmadic acid was also effective in protecting the plasmid DNA against strand breakage induced by hydroxyl radicals.