Oxidation products of hyperforin from Hypericum perforatum

Snežana Trifunović, Vlatka Vajs, Slobodan Macura, Nenad Juranić, Zoltan Djarmati, Ratko Jankov, Slobodan Milosavljević

Research output: Contribution to journalArticle

57 Scopus citations

Abstract

The isolation of two oxidation products of hyperforin from the aerial parts of Hypericum perforatum and their structure determination by means of 2D NMR methods is reported. The products had the same 1-(2-methyl-1- oxopropyl)-2,12-dioxo-3,10β-bis(3-methyl-2-butenyl)-11β-methyl-11α-(4- methyl-3-pentenyl)-5-oxatricyclo[6.3.1.0 4,8 ]-3-dodecene skeleton. In addition, one of them, with the same number of carbons as hyperforin (C 35 H 52 O 5 ), contained a 1-methyl-1-hydroxyethyl group in the 6β- position, whereas the other compound (a hemiacetal, C 32 H 46 O 5 ), presumably a degradation product of hyperforin, exhibited a 6-hydroxy function. The latter was an inseparable mixture of 6α- and 6β-hydroxy epimers undergoing (according to phase sensitive NOESY) mutual interconversion.

Original languageEnglish (US)
Pages (from-to)1305-1310
Number of pages6
JournalPhytochemistry
Volume49
Issue number5
DOIs
StatePublished - Nov 5 1998

Keywords

  • Hypericaceae
  • Hypericum perforatum
  • Oxidized hyperforins
  • Supercritical CO fractionation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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  • Cite this

    Trifunović, S., Vajs, V., Macura, S., Juranić, N., Djarmati, Z., Jankov, R., & Milosavljević, S. (1998). Oxidation products of hyperforin from Hypericum perforatum. Phytochemistry, 49(5), 1305-1310. https://doi.org/10.1016/S0031-9422(97)00903-5