Prenylated alkylbisphenols from Grevillea whiteana.
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.
Wang
Hao
H
Centre for Phytochemistry and Pharmacology, Southern Cross University, Lismore, NSW 2480, Australia. hwang13@scu.edu.au
Leach
David N
DN
Thomas
Michael C
MC
Blanksby
Stephen J
SJ
Forster
Paul I
PI
Waterman
Peter G
PG
D000107:Acetylation; D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010126:Ozone / Q000737:chemistry; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D054876:Prenylation; D039105:Proteaceae / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D010636:Phenols; D010936:Plant Extracts; D010126:Ozone