• Archives of Pharmacal Research
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• 제28권9호
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• pp.1031-1036
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• 2005

[ $(+)-Lyoniresinol-3{\alpha}-O-\beta-D-glucopyranoside$ ] (1) was isolated from an ethyl acetate extract of the root bark from Lycium chinense Miller, and its structure was determined using 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC. $(+)-Lyoniresinol-3{\alpha}-O-\beta-D-glucopyranoside$ exhibited potent antimicrobial activity against antibiotic-resistant bacterial strains, methicillin-resistant Staphylococcus aureus (MRSA) isolated from patients, and human pathogenic fungi without having any hemolytic effect on human erythrocytes. In particular, compound 1 induced the accumulation of intracellular trehalose on C. albicans as stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae caused by the pathogenesis. This indicates that $(+)-Lyoniresinol-3{\alpha}-O-\beta-D-glucopyranoside$ has excellent potential as a lead compound for the development of antibiotic agents.

• Journal of the Korean Wood Science and Technology
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• 제31권2호
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• pp.45-51
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• 2003

큰잎자작 변재의 메탄올(methanol, MeOH) 조추출물로부터 silica gel column, CPC 등의 크로마토그라피를 이용하여 4종의 화합물을 단리하였으며, 단리물질에 대한 NMR 등의 기기분석 결과, flavonoid 및 lignan 배당체인 catechin 7-O-𝛽-D-xylopyranoside, lyoniresinol 9'-O-𝛽-D-glucopyranoside, 그리고 diarylheptanoid인 11-oxo-3, 8, 12, 17-tetrahydroxy-9-ene [7, 0]-metacyclophane 및 11-oxo-3, 8, 9, 10, 12, 17-hexahydroxy [7, 0]-metacyclophane으로 각각 동정하였다.

• Journal of the Korean Wood Science and Technology
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• 제34권3호
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• pp.64-72
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• 2006

참식나무(Neolitsea sericea Koidz) 추출물의 염색특성을 구명하기 위하여 수피의 열수추출물에 대해 검토했다. 참식나무 수피의 열수추출물로부터 디에틸에테르와 에틸아세테이트로 분획하여 얻은 fraction을 TLC 및 column chromatography 처리하여 2개의 물질을 단리하였다. 기기분석을 통하여 단리물질의 구조를 해석한 결과, 알칼로이드 계열의 4H-dibenzoquinoline-2,10-diol, 5,6,6a,7-tetrahydro-1,9-dimethoxy-6-methyl (화합물I)과 리그난 계열의 lyoniresinol (화합물II)로 동정되었다. 이들 물질이 염색에 관여하는지 확인하기 위하여 HPLC를 사용하여 검토한 결과, 화합물(I)과 화합물(II)의 retention time이 참식나무 추출물 염색액 및 탈염액의 에틸아세테이트 fraction 중 주성분 피크의 retention time과 동일한 결과를 보였다. 따라서 화합물(I)과 화합물(II)가 참식나무 수피의 주요 염착물질임을 확인할 수 있었다.

• Natural Product Sciences
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• 제20권4호
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• pp.269-273
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• 2014

Activity guided phytochemical examination of the rhizome of Phragmites communis has led to the isolation of two phenolic acids and two lignans. Structures of these compounds were elucidated as methyl gallate (1), ${\rho}$ -hydroxy cinnamic acid (2), (+) -lyoniresinol (3), (+)-lyoniresinol-9'-O-${\beta}$-D-glucopyranoside (4) by comparisons with previously reported spectral data. To investigate the melanogenesis inhibitory effects of these compounds, the melanin level and tyrosinase activity were examined in B16F10 melanoma cell. Each compound inhibited both tyrosinase activity and melanin synthesis compared with positive control, kojic acid and arbutin. These results suggest that the phenolic compounds from Phragmites communis might be developed as a potent skin whitenting cosmeceuticals.

• 생약학회지
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• 제42권3호
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• pp.223-228
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• 2011

Chaenomeles sinensis Koehne (Rosaceae) is a deciduous tree and is distributed in China, Korea and Japan. In previous studies on the fruits of C. sinensis, some triterpenoid compouds such as oleanolic acid, tormentic acid were reported. In an ongoing investigation into biologically active compounds from natural products, the methanol extract of the stems of C. sinensis was investigated. By means of the repeated column chromatography using silica gel, Sephadex LH-20, LiChroprep RP-18, betulin (1), tormentic acid (2), 1-${\beta}$-D-glucopyranosyl-3,4,5-trimethoxybenzene (3), lyoniresinol-2a-O-${\alpha}$-L-rhamnopyranoside (4) were isolated. The chemical structures of compounds 1-4 were determined by the basis of physico-chemical properties and spectroscopic methods such as 1D and 2D NMR. For the isolated compounds (1-4), the inhibitory activity of IL-6 production in TNF-${\alpha}$ stimulated MG-63 cell was examined. Among the isolates, betulin (1), 1-${\beta}$-D-glucopyranosyl-3,4,5-trimethoxybenzene (3), lyoniresinol-2a-O-${\alpha}$-L-rhamnopyranoside (4) showed inhibitory effects on IL-6 production in TNF-${\alpha}$ stimulated MG-63 cell.

• Natural Product Sciences
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• 제20권2호
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• pp.95-101
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• 2014

Five lignan glycosides, seven megastigmane glycosides, and seven phenolic compounds were isolated by repeated column chromatography from the MeOH extract of Salsola komarovii. Their structures were determined to be lariciresinol-9-O-${\beta}$-$\small{D}$-glucopyranoside (1), alangilignoside C (2), conicaoside (3), (+)-lyoniresinol 9'-O-${\beta}$-$\small{D}$-glucopyranoside (4), (8S,8'R,7'R)-9'-[(${\beta}$-glucopyranosyl)oxy]lyoniresinol (5), blumenyl B ${\beta}$-$\small{D}$-glucopyranoside (6), blumenyl A ${\beta}$-$\small{D}$-glucopyranoside (7), staphylionoside D (8), icariside $B_2$ (9), (6R,9S)-3-oxo-${\alpha}$-ionol ${\beta}$-$\small{D}$-glucopyranoside (10), 3-oxo-${\alpha}$-ionol 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (11), blumenol B 9-O-${\beta}$-$\small{D}$-apiofuranosyl-($1{\rightarrow}6$)-${\beta}$-$\small{D}$-glucopyranoside (12), benzyl 6-O-${\beta}$-$\small{D}$-apiofuranosyl-${\beta}$-$\small{D}$-glucopyranoside (13), canthoside C (14), tachioside (15), isotachioside (16), biophenol 2 (17), 2-(3,4-dihydroxy)-phenyl-ethyl-${\beta}$-$\small{D}$-glucopyranoside (18), and cuneataside C (19) by spectroscopic methods. All the isolated compounds 1 - 19 were reported from this source for the first time. Compounds 2, 3 and 6 upregulated NGF secretion to $118.8{\pm}3.6%$, $128.2{\pm}9.3%$ and $111.1{\pm}7.1%$ without significant cell toxicity.

• Natural Product Sciences
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• 제11권2호
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• pp.97-102
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• 2005

From the n-BuOH soluble traction of the 70% aqueous acetone extract of Rhododendron mucronulatum stem, twelve compounds were isolated. On the basis of spectral data, they were identified as scopoletin (1), (+)-taxifolin (2), quercetin (3), (-)-catechin (4), (+)-epicatechin (5), scopolin (6), lyoniside (7), ssioriside (8), fraxin (9), $(+)-lyoniresinol-3{\alpha}-O-{\beta}-D-glucopyranoside$ (10), $(+)-taxifolin-3-O-{\alpha}-L-arabinopyranoside$ (11), and astragalin (12), respectively. All isolated compounds were tested antioxidant activity against 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical. Compounds 2 and 3 showed the potent antioxidant activity, and compounds 5, 8, and 11 showed moderate activity.

• Natural Product Sciences
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• 제15권1호
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• pp.17-21
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• 2009

Column chromatographic separation of the alcoholic extract from the roots of Berberis amurensis yielded eight phenolic constituents including six lignans, hanultarin (1), (-)-secoisolariciresinol (3), (+)-lyoniresinol (5), (+)-syringaresinol (6), (+)-syringaresinol-O-$\beta$-D-glucopyranoside (7), liriodendrin (8), and two phenylpropanoids, 4-glucosyloxy-3-methoxyphenyl trans-propenoic ethyl ester (2), trans-ferulic acid (4). The structures were determined on the basis of NMR spectroscopic data. All isolated compounds(1-8) were reported for the first time from this source. Compound 1 exhibited moderate cytotoxicity against four human cancer cell lines in vitro using sulforhodamin B bioassay.

• Natural Product Sciences
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• 제8권2호
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• pp.62-65
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• 2002

Two lupane-type triterpenes, lupenone (1) and lupeol (2), a phytosterol, ${\beta}-sitosterol$ (3), two ursane-type triterpenes, $3{\beta}-acetoxy$ ursolic acid (4) and ursolic acid (5), a lignan, (-)-lyoniresinol $3a-O-{\beta}-D-xylopyranoside$ (6), and two flavanol glycosides, $catechin-7-O-{\beta}-D-xylopyranoside$ (7) and $catechin-7-O-{\beta}-D-apiofuranoside$ (8) were isolated from the stem bark of Sorbus commixta (Rosaceae). Their chemical structures were identified by physicochemical and spectroscopic methods.

• Archives of Pharmacal Research
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• 제25권4호
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• pp.433-437
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• 2002

A new phenolic amide, dihydro-N-caffeoyltyramine (1) was isolated from the root bark of Lycium chinense Miller, along with known compounds, trans-N-caffeoyltyramine (2), cis-N-caffeoyltyramine (3), and lyoniresinol $3{\alpha}-Ο-{\beta}-D-glucopyranoside$ (4). Their structures were determined by spectroscopic analysis. A NBT superoxide scavenging assay revealed that three phenolic amides showed potent antioxidative activity.