Tannins and Related Compounds. LI. Elucidation of the Stereochemistry of the Triphenoyl Moiety in Castalagin and Vescalagin, and Isolation of 1-Ο-Galloyl Castalagin from Eugenia grandis

GEN-ICHIRO NONAKA; KANJI ISHIMARU; MICHIYO WATANABE; ITSUO NISHIOKA; TATSUO YAMAUCHI; ALFRED S. C. WAN

doi:10.1248/cpb.35.217

Tannins and Related Compounds. LI. Elucidation of the Stereochemistry of the Triphenoyl Moiety in Castalagin and Vescalagin, and Isolation of 1-Ο-Galloyl Castalagin from Eugenia grandis

GEN-ICHIRO NONAKA, KANJI ISHIMARU, MICHIYO WATANABE, ITSUO NISHIOKA, TATSUO YAMAUCHI, ALFRED S. C. WAN

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Keywords: castalagin, vescalagin, C-glycosidic ellagitannin, atropisomerism, absolute stereochemistry, nonahydroxytriphenoyl group, flavogallonic acid, Eugenia grandis, 1-Ο-galloyl castalagin

JOURNAL FREE ACCESS

1987 Volume 35 Issue 1 Pages 217-220

DOI https://doi.org/10.1248/cpb.35.217

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Abstract

The chirality of the nonahydroxytriphenoyl group in castalagin (1) and vescalagin (2) was determined to be in the S, S-series on the basis of circular dichroism analysis. In addition, a new ellagitannin (4) has been isolated from the leaves of Eugenia grandis (Myrtaceae), and the structure was established to be 1-Ο-galloyl castalagin on the basis of chemical and spectroscopic evidence.

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