Three isoflavanones with cannabinoid-like moieties from Desmodium canum

B. Botta, E. Gács-Baitz, V. Vinciguerra, G. Delle Monache

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Three further derivatives of 5,7,2′,4′-tetrahydroxy-6-methyl isoflavanone have been isolated from the root extract of Desmodium canum and assigned the structures 2,3-dihydro-5,7-dihydroxy-6-methyl-3-(1a,2,3,3a,8b,8c-hexahydro-6-hydroxy-1,1, 3a-trimethyl-1H-4-oxabenzo[f]cyclobut[c,d]inden-7-yl)-4H-1-benzopyran-4-one (1) 2,3-dihydro-5,7-dihydroxy-6-methyl-3-(6a,7,8,10a-tetrahydro-3-hydroxy-6,6, 9-trimethyl-6H-dibenzo[b,d]pyran-2-yl)-4H-1-benzopyran-4-one (2) 2,3-dihydro-5,7-dihydroxy-6-methyl-3-(3-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d] pyran-2-yl) 4H-1-benzopyran-4-one (3). The three compounds and the previously isolated chromene 4 all derive from the geranylated precursor 5 by a series of cannabinoid-like oxidative rearrangements.

Original languageEnglish
Pages (from-to)599-602
Number of pages4
JournalPhytochemistry
Volume64
Issue number2
DOIs
Publication statusPublished - Sep 2003

Fingerprint

Desmodium incana
benzopyrans
cannabinoids
Cannabinoids
Pyrans
pyrans
Benzopyrans
chemical derivatives
Derivatives
extracts
benzopyran-4-one
isoflavanone

Keywords

  • Cannabinoid-like substitutions
  • Desmodium canum
  • Isoflavanones
  • Leguminosae

ASJC Scopus subject areas

  • Plant Science
  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery

Cite this

Three isoflavanones with cannabinoid-like moieties from Desmodium canum. / Botta, B.; Gács-Baitz, E.; Vinciguerra, V.; Delle Monache, G.

In: Phytochemistry, Vol. 64, No. 2, 09.2003, p. 599-602.

Research output: Contribution to journalArticle

Botta, B. ; Gács-Baitz, E. ; Vinciguerra, V. ; Delle Monache, G. / Three isoflavanones with cannabinoid-like moieties from Desmodium canum. In: Phytochemistry. 2003 ; Vol. 64, No. 2. pp. 599-602.
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