Diarylheptanoids from the Rhizomes of Curcuma xanthorrhiza and Alpinia officinarum

SHIN-ICHI UEHARA; ICHIRO YASUDA; KAZUYUKI AKIYAMA; HIROSHI MORITA; KOICHI TAKEYA; HIDEJI ITOKAWA

doi:10.1248/cpb.35.3298

Diarylheptanoids from the Rhizomes of Curcuma xanthorrhiza and Alpinia officinarum

SHIN-ICHI UEHARA, ICHIRO YASUDA, KAZUYUKI AKIYAMA, HIROSHI MORITA, KOICHI TAKEYA, HIDEJI ITOKAWA

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Keywords: diarylheptanoid, Curcuma xanthorrhiza, Alpinia officinarum, Zingiberaceae, (3S, 5S) -1, 7-bis (4-hydroxy-3-methoxyphenyl) -heptane-3, 5-diol, (1ζ) -1-hydroxy-1, 7-bis (4-hydroxy-3-methoxyphenyl) -6-heptene-3, 5-dione, (3R, 5R) -1- (4-hydroxyphenyl) -7-phenylheptane-3, 5-diol, exciton chirality rule, CD

JOURNAL FREE ACCESS

1987 Volume 35 Issue 8 Pages 3298-3304

DOI https://doi.org/10.1248/cpb.35.3298

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Abstract

Five diarylheptanoids including two new compounds were isolated from the rhizomes of Curcuma xanthorrhiza (Zingiberaceae). The structures of the new compounds were determined to be octahydrocurcumin ((3S, 5S) -1, 7-bis (4-hydroxy-3-methoxyphenyl) -heptane-3, 5-diol) (Ia) and (1ξ) -1-hydroxy-1, 7-bis (4-hydroxy-3-methoxyphenyl) -6-heptene-3, 5-dione (II) on the basis of spectral and chemical evidence.
The absolute configurations of Ia and a new similar diarylheptanoid, (3R, 5R) -1- (4-hydroxyphenyl) -7-phenylheptane-3, 5-diol (VIa), isolated from the rhizomes of Alpinia officinarum (Zingiberaceae), were established by application of the exciton chirality rule.

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