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Planta Med 1994; 60(5): 464-466
DOI: 10.1055/s-2006-959533
Paper

© Georg Thieme Verlag Stuttgart · New York

Novel Galloylhamameloses from Hamamelis virginiana 1

Claudia Haberland2 , H. Kolodziej2
  • 2Institüt für Pharmazeutische Biologie, Freie Universität Berlin, D-14195 Berlin, Federal Republic of Germany
1 Presented in parts as poster during the meeting of the Society of Medicinal Plant Research, Düsseldorf, FRG, Sept. 1993. Part of the projected thesis of C. Haberland
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Publication History

1993

1994

Publication Date:
04 January 2007 (online)

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Abstract

The range of natural galloylhamameloses is extended by the recognition of the highly unstable novel analogues, the 1-O-(4-hydroxybenzoyl)-2′,5-di-O-galloyl-α-D-hamamelofuranose and its 1-O-β-anomer. The observed facile elimination of the C-1 acyl moiety is discussed and a mechanism proposed. These compounds are accompanied in the bark of Hamamelis virginiana by the “conventional” hamamelitannin, the related new 1,2′,5-tri-O-galloyl-α-D-hamamelofuranose, and a tentatively characterized di-O-galloyl-D-hamamelopyranose, the first pyranose analogue, shown to be also present in commercially available hamamelitannin. The structures of these compounds were established from spectroscopic evidence of their acetate derivatives.

Key words

Hamamelis virginiana - Hamamelidaceae - galloylhamameloses