Novel cytotoxic, alkylated hydroquinones from Lannea welwitschii.
Two novel natural products, lanneaquinol (1) and 2'(R)-hydroxylanneaquinol (2), were isolated from the organic extract of the plant Lannea welwitschii (Hiern) Engl. Their structures were solved by spectroanalytical methods and confirmed by comparison to synthetic models. The absolute configuration of 2 was determined by the modified Mosher method. Both compounds exhibited modest cytotoxicity against the NCI panel of 60 human tumor cell lines. The structures of two isomeric 4,5-dihydroxy-5-alkyl-2-cyclohexenones (7 and 8), which appear to be biogenetic precursors of 1 and 2, were also elucidated.
Groweiss
A
A
Laboratory of Drug Discovery Research and Development, National Cancer Institute-Frederick Cancer Research and Development Center, Maryland 21702-1201, USA.
Cardellina
J H
JH
Pannell
L K
LK
Uyakul
D
D
Kashman
Y
Y
Boyd
M R
MR
D000478:Alkylation; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002852:Chromatography, Ion Exchange; D006801:Humans; D006873:Hydroquinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured
C104800:2'-hydroxylanneaquinol; D000972:Antineoplastic Agents, Phytogenic; D006873:Hydroquinones; C104799:lanneaquinol