Two 2-hydroxy-2-benzylcoumaranone glycosides, 2,4,6-trihydroxy-2-[(4'- hydroxyphenyl) methyl]3(2H)-benzofuranone-4-yl-β-D-glucopyranoside (maesopsin 4-O-glucoside) (1) and 2,4,6-trihydroxy-2-[(4'-hydroxyphenyl) methyl]-3(2H)-benzofuranone-4-yl-β-D-glucopyranosido-4'-yl-α- Lrhamnopyranoside (maesopsin 4-O-glucosido 4'-O-rhamnoside) (2), two neolignan glycosides, 2R-(E)-2,3-dihydro-2-(4'hydroxy-3'-methoxylphenyl)-5- (3'-hydroxy-1'-propenyl)-7-methoxy-3-benzofuranmethanol-4'yl-β-D- glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(→2)]-β-D-glucopyranoside (3) and (threo) 1-(4'-hydroxy-3'-methoxy)-2-(4-hydroxymethyl-2,6- dimethoxyphenoxy)propane-1,3-diol-4'-yl-β-D-glucopynoside (4), and a phenylpropanoid glycoside, 3-methoxy-5(2'-propenyl)-1,2-benzenediol-1-ylβ- D-apiofuranosyl-(1→6)-β-D-glucopyranoside (5) were isolated from the bark of Hovenia trichocarea. Compounds 1-5 were named hovetricosides C-G, respectively, and their structures were established by extensive NMR experiments and chemical methods. Also obtained in this investigation were the known compounds acanthoside B, kelampayoside A, shashenoside I, and 3,4,5-trimethoxyphenol-1-O-β-D-xylopyranosyl-(1→6)β-D-glucopyranoside.
Carbohydrate Sequence, Molecular Sequence Data, hydrolysis, Magnetic Resonance Spectroscopy, glycosides, plant epidermis, high pressure liquid chromatography
NCBI PubMed ID: 9644065Publication DOI: 10.1021/np9800396Journal NLM ID: 7906882Publisher: American Society of Pharmacognosy
Institutions: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima, Japan
Methods: 13C NMR, 1H NMR, NOE, FAB-MS, acid hydrolysis, HPLC, UV, extraction, optical rotation measurement, CD, CC, melting point determination, HMBC, FT-IR