Biogenetic relationships between Annonaceous acetogenins: squamocin is not a precursor of chamuvarinin based on a semisynthetic study.
In the course of reactivity studies on squamocin (1), a highly cytotoxic acetogenin from the plant family Annonaceae, two diastereomers, 3 and 4, of chamuvarinin (2) were synthesized. Based on this, a plausible relative configuration was proposed for 2, demonstrating the absence of any biogenetic link between 1 and 2. The new analogues 3, 4, and 7 were also tested for their ability to induce apoptosis.
Derbré
Séverine
S
Laboratoire de Pharmacognosie Associé au CNRS (BioCIS, UMR 8076), Université Paris-Sud 11, Faculté de Pharmacie, 5 rue Jean-Baptiste Clément, 92296 Châtenay-Malabry Cedex, France.
Poupon
Erwan
E
Gleye
Christophe
C
Hocquemiller
Reynald
R
D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D005233:Fatty Alcohols / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005663:Furans / Q000737:chemistry* / Q000378:metabolism; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry* / Q000378:metabolism
D054378:Acetogenins; D000972:Antineoplastic Agents, Phytogenic; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; D011714:Pyrans; C488316:chamuvarinin; C059660:squamocin