• Archives of Pharmacal Research
• /
• v.28 no.9
• /
• pp.1031-1036
• /
• 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.

• Natural Product Sciences
• /
• v.20 no.2
• /
• pp.95-101
• /
• 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.

• Journal of the Korean Wood Science and Technology
• /
• v.31 no.2
• /
• pp.45-51
• /
• 2003

One flavonoid, lignan glycosides and two diarylheptanoids were isolated from the sapwood of Betula maximowicziana. The structures were determined as : catechin 7-O-𝛽-D-xylopyranoside, lyoniresinol 9'-O-𝛽-D-glucopyranoside, 11-oxo-3, 8, 12, 17-tetrahydroxy-9-ene[7, 0]-metacyclophane and 11-oxo-3, 8, 9, 10, 12, 17-hexahydroxy[7, 0]-metacyclophane, respectively, on the basis of spectrosopic data and chemical correlations.

• Natural Product Sciences
• /
• v.11 no.2
• /
• pp.97-102
• /
• 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
• /
• v.20 no.4
• /
• pp.269-273
• /
• 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.