Components of Ether-Insoluble Resin Glycoside (Rhamnoconvolvulin) from Rhizoma Jalapae Braziliensis

Masateru Ono; Hiroko Nishioka; Tadashi Fukushima; Hiroko Kunimatsu; Aiko Mine; Hideo Kubo; Kazumoto Miyahara

doi:10.1248/cpb.57.262

Regular Articles

Components of Ether-Insoluble Resin Glycoside (Rhamnoconvolvulin) from Rhizoma Jalapae Braziliensis

Masateru Ono, Hiroko Nishioka, Tadashi Fukushima, Hiroko Kunimatsu, Aiko Mine, Hideo Kubo, Kazumoto Miyahara

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Keywords: resin glycoside, Ipomoea operculata, Rhizoma Jalapae Braziliensis, operculinic acid H, 3S,12S-dihydroxyhexadecanoic acid, exogonic acid

JOURNAL FREE ACCESS

2009 Volume 57 Issue 3 Pages 262-268

DOI https://doi.org/10.1248/cpb.57.262

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Abstract

Alkaline hydrolysis of the ether-insoluble resin glycoside (convolvulin) fraction of the roots of Ipomoea operculata (GOMES) MART. (Convolvulaceae) afforded a glycosidic acid named operculinic acid H along with isovaleric, tiglic, and exogonic (3,6:6,9-diepoxydecanoic) acids. Operculinic acid H was characterized to be 3S,12S-dihydroxyhexadecanoic acid 12-O-β-D-glucopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2)-[O-β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→2)-[O-α-L-rhamnopyranosyl-(1→6)]-O-β-D-glucopyranoside on the basis of spectroscopic data and chemical evidence. The absolute configuration of exogonic acid determined from the α-methoxy-α-trifluoromethylphenylacetic acid esters of the hydrogenolysis products revealed that exogonic acid exists as a mixture (ca. 1 : 1) of two epimers, (3S,6S,9R)- and (3S,6R,9R)-diepoxydecanoic acids.

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