Novel naphthoquinones from Conospermum incurvum.
During the reisolation of the trimeric naphthoquinone derivative conocurvone [1] from an extract of the Australian shrub Conospermum incurvum, six monomeric naphthoquinones were isolated. These include three novel 1,4-naphthoquinone derivatives: 3-methyl-14,15-dihydro-15-hydroxyteretifolione B [3], 3-methyl-14,15-dihydro-15-hydroxyteretifolione B methyl ether [4], and 2,3-dimethyl-6-hydroxy-7-methoxy-1,4-naphthoquinone [5]. In addition, the previously reported compounds 3-methylteretifolione B [6], 3-methylteretifolione B methyl ether [7], and 8-geranyl-2,7-dihydroxy-3-methyl-1,4-naphthoquinone [8] were isolated and identified. The structures of the novel 1,4-naphthoquinones were elucidated by spectral methods. While conocurvone [1] is a potent inhibitor of HIV-1-induced cell killing, all of the monomeric naphthoquinone derivatives were inactive against HIV-1.
Dai
J R
JR
Laboratory of Drug Discovery Research and Development, National Cancer Institute, Frederick, Maryland 21702-1201.
Decosterd
L A
LA
Gustafson
K R
KR
Cardellina
J H
JH
Gray
G N
GN
Boyd
M R
MR
D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001315:Australia; D002470:Cell Survival / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects* / Q000472:pathogenicity; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots; D010944:Plants / Q000737:chemistry*
D000998:Antiviral Agents; D009285:Naphthoquinones; C091977:conocurvone