Megastigmane glucosides from Equisetum debile and E. diffusum

Abstract

A new megastigmane diglucoside, (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6- epoxy-3,9-diol 3,9-O-β-D-diglucopyranoside (3), was isolated from the aerial portion of Equisetum debile along with macarangioside D (debiloside A), sammangaoside A, (6R,9S)-3-oxo-α-ionol 9-O-β-D-glucopyranoside, debiloside B, kaempferol 3-O-sophoroside, kaempferol 3,7-O-β-D- diglucopyranoside, kaempferol 3-O-sophoroside-7-O-β-D-glucopyranoside, phenylethyl O-β-D-glucopyranoside, (Z)-3-hexenyl O-β-D- glucopyranoside, (7S,8R)-dehydrodiconiferyl 4-O-β-D-glucopyranoside, and L-tryptophan. The absolute configuration at C-6 of the original structure of debiloside A was revised to 6R-configuration, and was identical with macarangioside D (1). From the aerial portion of E. diffusum, four compounds, sammangaoside A, kaempferol 3-O-sophoroside and L-tryptophan and (3S,5R,6S,7E,9S)-megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-β-D- glucopyranoside were identified. The spectroscopic data of (3S,5R,6S,7E,9S)- megastigman-7-ene-5,6-epoxy-3,9-diol 3-O-β-D-glucopyranoside (13) were found to be identical with corchoionoside A (9R-isomeric compound). The structure of corchoionoside A was also discussed. Structure determinations were based on physical data and spectroscopic evidence. © 2007 Pharmaceutical Society of Japan.