Alkaline hydrolysis of the ether-insoluble resin glycoside ("convolvulin") fraction, pharbitin, of the seeds of Pharbitis nil (Convolvulaceae) provided three organic acids, S-2-methylbutyric acid, (2R, 3R)-nilic acid and tiglic acid, and a new glycosidic acid named pharbitic acid B along with the known compounds pharbitic acids C and D. Pharbitic acid B was characterized as (3S,11S)-3,11-dihydroxyhexadecanoic acid 11-O-α-L-rhamnopyranosyl-(1→3)-O-β-D-quinovopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside. The structures of the sugar moieties of pharbitic acids C and D were revised.
resin glycoside, pharbitin, Pharbitidis Semen, Pharbitis nil, glycosidic acid, pharbitic acid B, pharbitic acid C, pharbitic acid D, (3S, 11S)-ipurolic acid oligoside, 11S)-3, 11-dihydroxyhexadecanoic acid oligoside, hydroxyfatty acid FD-MS
Journal NLM ID: 0377775WWW link: http://ci.nii.ac.jp/naid/110003628670Publisher: Pharmaceutical Society Of Japan
Institutions: Faculty of Pharmaceutical Sciences, Setsunan University, Japan
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, alkaline hydrolysis, permethylation analysis