Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers.
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Glycosidic inhibitors of melanogenesis from leaves of Passiflora edulis.
Chem Biodivers
October 2013
College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Chiyoda-ku, Tokyo 101-8308, Japan.
A new flavonoid glycoside, chrysin 6-C-β-rutinoside (chrysin α-L-rhamnopyranosyl-(1→6)-C-β-glucopyranoside; 2), and two new triterpene glycosides, (31R)-31-O-methylpassiflorine (7) and (31S)-31-O-methylpassiflorine (8), along with 14 known glycosides, including three flavonoid glycosides, 1, 3, and 4, six triterpene glycosides, 5, 6, and 9-12, three cyano glycosides, 13-15, and two other glycosides, 16 and 17, were isolated from a MeOH extract of the leaves of Passiflora edulis (passion flower; Passifloraceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analysis and comparison with literature data. Upon evaluation of compounds 1-17 against the melanogenesis in the B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, isoorientin (1), 2, and (6S,9R)-roseoside (17), exhibited inhibitory effects with 37.
View Article and Find Full Text PDFA simple synthesis of four stereoisomers of roseoside and their inhibitory activity on leukotriene release from mice bone marrow-derived cultured mast cells.
Bioorg Med Chem
January 2009
Department of Fermentation Science, Faculty of Applied Biological Science, Tokyo University of Agriculture (NODAI), Sakuragaoka 1-1-1, Setagaya-ku, Tokyo 156-8502, Japan.
Four stereoisomers of roseoside (vomifoliol glucosides) were synthesized using glucose as a chiral resolving reagent. The four synthetic stereoisomers exhibited inhibitory activity on leukotriene release from mouse bone marrow-derived cultured mast cells (BMCMC). The (6S)-isomers of roseoside were about twice as active as (6R)-isomers.
View Article and Find Full Text PDFSynthesis of optically active vomifoliol and roseoside stereoisomers.
Chem Pharm Bull (Tokyo)
May 2005
Kobe Pharmaceutical University, Kobe 658-8558, Japan.
A synthesis of optically active vomifoliol stereoisomers 1-4 and their glucosides, roseoside stereoisomers 5-8, was accomplished via alpha-acetylenic alcohol 11a or 11b effectively prepared by an asymmetric transfer hydrogenation of alpha,beta-acetylenic ketone 10. Simultaneous separation of these stereoisomers by HPLC was also performed.
View Article and Find Full Text PDFThree new ionone glucosides named corchoionosides A, B, and C were isolated from the leaves of Corchorus olitorius, commonly called "moroheiya" in Japanese, together with seven known compounds, an ionone glucoside (6S,9R)-roseoside, a monoterpene glucoside betulalbuside A, two flavonol glucosides astragalin and isoquercitrin, two coumarin glucosides scopolin and cichoriine, and chlorogenic acid. The absolute stereostructures of corchoionosides A, B, and C were determined by chemical and physiochemical evidence, which included the result of application of a modified Mosher's method, the CD helicity rule, and chemical correlation with (6S,9R)-roseoside. Corchoionosides A and B and (6S,9R)-roseoside were found to inhibit the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.
View Article and Find Full Text PDFAlangionosides G-M: glycosides of megastigmane derivatives from the leaves of Alangium premnifolium.
Chem Pharm Bull (Tokyo)
May 1995
Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Japan.
Phytochemical investigation of the 1-BuOH-soluble fraction of the MeOH extract of Alangium premnifolium resulted in the isolation of ten megastigmane glycosides, of which, two, (6R,9R)-3-oxo-alpha-ionol apiofuranosylglucopyranoside and roseoside with (6S,9R)-blumeol A as an aglycone were known. The structures of the eight new compounds were determined by spectroscopic methods.
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