Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro

Iris Djordjević, Vlatka Vajs, Vanja Bulatović, Nebojša Menković, Vele Tešević, Slobodan Macura, Pedja Janaćković, Slobodan Milosavljević

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Quantitative 1H NMR measurements revealed Δ 11(13) sesquiterpene γ-lactones as the main constituents (≥ 1% per weight of dried plant material) in the crude extracts of the aerial parts of Amphoricarpos neumayeri ssp. neumayeri and ssp. murbeckii from mountains Orjen and Visitor (Montenegro), respectively. Preparative silica gel chromatography afforded thirteen guai-11(13)-en-12,6α-olides, named amphoricarpolides (1-13), with the same relative (1αH,4βH,5αH, 7βH) configuration of the basic skeleton. The common structural feature of lactones 2-13 was 3β,15-dioxygenation pattern. The only exception was 1 (3-deoxyamphoricarpolide), containing a single oxygen substituent (15-OH). Eight of them exhibited an additional oxygen substituent, 9β-OH (5 and 6), 2α-OH (8-12), or 2α-OAc (13). Compound 7 was epoxydated at 10α(14)-position, whereas the remaining lactones contained a 10(14) double bond.

Original languageEnglish (US)
Pages (from-to)2337-2345
Number of pages9
JournalPhytochemistry
Volume65
Issue number16
DOIs
StatePublished - Aug 2004

Keywords

  • Amphoricarpolides
  • Amphoricarpos neumayeri
  • Asteraceae
  • Guaianolides
  • Sesquiterpene lactones

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

Fingerprint Dive into the research topics of 'Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro'. Together they form a unique fingerprint.

  • Cite this

    Djordjević, I., Vajs, V., Bulatović, V., Menković, N., Tešević, V., Macura, S., Janaćković, P., & Milosavljević, S. (2004). Guaianolides from two subspecies of Amphoricarpos neumayeri from Montenegro. Phytochemistry, 65(16), 2337-2345. https://doi.org/10.1016/j.phytochem.2004.07.014