Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata.
The leaves of Annona muricata have yielded eight monotetrahydrofuran Annonaceous acetogenins. Two of them, annomuricins A [1] and B [2], whose chemical structures were deduced by ms, nmr, ir, and uv spectral and chemical methods, are novel and unusual. Compounds 1 and 2 each possess five hydroxyl groups; two hydroxyl groups are vicinal, with the vicinal group of 1 threo and that of 2 erythro. The absolute configurations of 1 and 2 were determined by Mosher ester methodology. Six monotetrahydrofuran acetogenins, previously described in the seeds, were found in the leaves; these are gigantetrocin A, annonacin-10-one, muricatetrocins A and B, annonacin, and goniothalamicin.
Wu
F E
FE
Department of Medicinal Chemistry and Pharmacognosy, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907, USA.
Gu
Z M
ZM
Zeng
L
L
Zhao
G X
GX
Zhang
Y
Y
McLaughlin
J L
JL
Sastrodihardjo
S
S
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000032:analysis / Q000302:isolation & purification; D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000302:isolation & purification*; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000032:analysis / Q000302:isolation & purification*; D006801:Humans; D007214:Indonesia; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; C095611:annomuricin A; D015107:4-Butyrolactone