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Planta Med 1988; 54(4): 333-337
DOI: 10.1055/s-2006-962449
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© Georg Thieme Verlag Stuttgart · New York

Novel Cyclopentenoid Cyanohydrin Rhamnoglucosides from Flacourtiaceae1

Jerzy W. Jaroszewski, Dorthe Bruun, Vicki Clausen, Claus Cornett
  • Department of Chemistry BC, Royal Danish School of Pharmacy, Universitetsparken 2, DK-2100 Copenhagen, Denmark.
1 Part VII in the series “Cyclopentenoid Cyanohydrin Glycosides”. For part VI, see Jaroszewski, J. W., Jensen, P. S., Cornett, C., Byberg, J. R. (1987) Biochem. Syst. Ecol. 16, 23-28.
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1987

Publication Date:
24 January 2007 (online)

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Abstract

Two novel cyclopentenoid cyanohydrin glycosides, (1S,4R)-and (1R,4S)-1-[6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-4-hydroxy-2-cyclopentene-1-carbonitrile, were isolated from seeds of the Indian medicinal plant Hydnocarpus pentandra (F. Ham.) Oken (Flacourtiaceae) and characterized by optical rotations as well as 1H-and 13C-NMR spectra. The structural assignment is founded on these data and on degradation with α-L-rhamnosidase to the corresponding β-D-glucopyranosides, epivolkenin and taraktophyllin, also present in the seeds in small amounts. Earlier reports of cyclopentenoid rhamnoglucosides from Passifloraceae are rejected.