Mono-tetrahydrofuran acetogenins from Goniothalamus giganteus.
Goniotetracin and a mixture of (2,4-cis and trans)-gonioneninone, new, bioactive, mono-tetrahydrofuran (THF) gamma-lactone and ketolactone acetogenins, were isolated from the bark of Goniothalamus giganteus (Annonaceae) by activity-directed fractionation using the brine shrimp lethality test (BST). The structures were elucidated based on spectroscopic and chemical methods. Their absolute stereochemistries were determined by the advanced Mosher ester method. Both showed selective and significant cytotoxicities, comparable to the potency of adriamycin, to the human pancreatic tumour cell line (PACA-2), while goniotetracin and goniothalamicin were comparable to the activity of rotenone against yellow fever mosquito larvae.
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
F Q
FQ
Alali
Y
Y
Zhang
L
L
Rogers
J L
JL
McLaughlin
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001156:Artemia; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D010946:Plants, Medicinal / Q000737:chemistry*; D014407:Tumor Cells, Cultured
C115309:2,4-gonioneninone; D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; C115308:goniotetracin; D015107:4-Butyrolactone