Glabracins A and B, two new acetogenins from Annona glabra.
Two new bioactive bis-THF Annonaceous acetogenins, glabracins A (1) and B (2), and two previously known acetogenins, javoricin (3) and bullatanocin (4), have been isolated from the leaves of Annona glabra by activity-directed fractionation using the brine shrimp lethality test (BST). The structures of 1 and 2 were elucidated based on spectroscopic and chemical methods, and the absolute stereochemistries were partially determined by the advanced Mosher ester method. 1 and 2 showed selective cytotoxicities to certain human tumor cell lines, and 1 was significantly more potent although 1 and 2 differ only in the stereochemistry of their vicinal diols at C-23/24.
Liu
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Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA.
Alali
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FQ
Hopp
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Rogers
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Pilarinou
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McLaughlin
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JL
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D001156:Artemia; D005591:Chemical Fractionation; D004354:Drug Screening Assays, Antitumor; D005431:Florida; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D006801:Humans; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology / Q000633:toxicity; D007928:Lethal Dose 50; D009682:Magnetic Resonance Spectroscopy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D013237:Stereoisomerism; D014197:Trees / Q000737:chemistry*; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D007783:Lactones; D010936:Plant Extracts; C115097:glabracin A