Prenylated alkylbisphenols from Grevillea whiteana

Nat Prod Commun. 2009 Jul;4(7):951-8.

Abstract

Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl)grebustol-B (10a), 4'-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4'-(4-hydroxy-3-methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)-resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5'-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5'-(8(Z)-hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Chromatography, High Pressure Liquid
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Ozone / chemistry
  • Phenols / chemistry*
  • Phenols / isolation & purification
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Plant Stems / chemistry
  • Prenylation
  • Proteaceae / chemistry*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Phenols
  • Plant Extracts
  • Ozone