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Planta Med 1997; 63(4): 347-351
DOI: 10.1055/s-2006-957698
Papers
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Dammaranes, Esterified with Malonic Acid, from Leaves of Betula pendula

U. Hilpisch1 , R. Hartmann2 , K.-W. Glombitza1
  • 1Institut für Pharmazeutische Biologie, Universität Bonn, Nussallee 6, D-53115 Bonn, Germany
  • 2Institut für Physiologische Chemie, Universität Bonn, Nussallee 11, D-53115 Bonn, Germany
Further Information

Publication History

1996

1997

Publication Date:
04 January 2007 (online)

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Abstract

Three known and five new dammarane triterpenes, esterified with malonic acid at C-3 with hemolytic activity were identified from the ethanol-water extract of leaves of Betula pendula Roth: 12-O-acetyl-3α,12β,20(S),24(R)-tetrahydroxydammar-25-en-3-yl hydrogen propanedioate, 12-O-acetyl-3α,12β20(S),24(S)-tetrahydroxydammar-25-en-3-yl hydrogen propanedionate, 12-O-acetyl-3α,12β,17α,20(S),24(R)-pentahydroxydammar-25-en-3-yl hydrogen propanedioate, [12β-acetoxy-4,4,8,10,14-pentamethyl-17-(2-methyl-5-oxotetrahydrofuran2(S)-yl)-hexadecahydrocyclopenta[a]phenanthren-3α-yl] hydrogen propanedioate, 12-O-acetyl-3α,12β,20(S),25-pentahydroxydammar-23(E)-en-3-yl hydrogen propanedioate, and one which was new for Betula pendula but found in other Betula species: 12-O-acetyl-20,24-epoxy-3α,12β,20(S),24(R),25-pentahydroxydammar-3-yl hydrogen propanedioate. The structures were elucidated by MS, 1H-NMR, 13C-NMR, 1H-1H-COSY, DEPT, 1H-13C-NMR (HMQC, HMBC) experiments.

Key words

Betula pendula - Betulaceae - saponins - triterpenes - dammarane esters