Chamuvarinin, an acetogenin bearing a tetrahydropyran ring from the roots of Uvaria chamae.
A new cytotoxic acetogenin, chamuvarinin (1), containing a tetrahydropyran ring with an adjacent bis-tetrahydrofuran ring, which corresponds to a novel carbon skeleton in this series, was isolated from the roots of Uvaria chamae, together with the previously reported acetogenins squamocin (2), desacetyluvaricin (3), and neoannonin (4). The structure determination of chamuvarinin (1) was based on extensive NMR studies and high-resolution mass spectral measurements. This new compound shows significant cytotoxicity toward the KB 3-1 cell line (IC50 = 8 x 10(-10) M). In addition, a biosynthetic relationship between 1 and 2 is briefly discussed.
Fall
Djibril
D
Laboratoire de Pharmacognosie, UMR 8076 CNRS (BioCIS), Faculté de Pharmacie, Université Paris XI, 92296 Châtenay-Malabry, France.
Duval
Romain A
RA
Gleye
Christophe
C
Laurens
Alain
A
Hocquemiller
Reynald
R
D054378:Acetogenins; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D007624:KB Cells; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012675:Senegal; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D031046:Uvaria / Q000737:chemistry*
D054378:Acetogenins; D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D011714:Pyrans; C488316:chamuvarinin