Components of ether-insoluble resin glycoside (rhamnoconvolvulin) from rhizoma jalapae braziliensis.
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-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-[O-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->2)-[O-alpha-L-rhamnopyranosyl-(1-->6)]-O-beta-D-glucopyranoside on the basis of spectroscopic data and chemical evidence. The absolute configuration of exogonic acid determined from the alpha-methoxy-alpha-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.
Ono
Masateru
M
School of Agriculture, Tokai University, Aso, Kumamoto 869-1404, Japan. mono@agri.u-tokai.ac.jp
Nishioka
Hiroko
H
Fukushima
Tadashi
T
Kunimatsu
Hiroko
H
Mine
Aiko
A
Kubo
Hideo
H
Miyahara
Kazumoto
K
D001938:Brazil; D002240:Carbohydrate Sequence; D004986:Ether / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D027741:Ipomoea / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D018517:Plant Roots / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; C482480:operculinic acid; D004986:Ether