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- Title
Muricatetrocins A and B and Gigantetrocin B: Three New Cytotoxic Monotetrahydrofuran-Ring Acetogenins from Annona muricata.
- Authors
Rieser, Matthew J.; Fang, Xing-Ping; Anderson, Jon E.; Miesbauer, Laura R.; Smith, David L.; McLaughlin, Jerry L.
- Abstract
Extracts from the seeds of Annona muricata yielded three new Annonaceous acetogenins: muricatetrocin A (= (5 S)-3-{(2 R)-2-hydroxy-9-{(2 R,5 S)-tetrahydro-5-[(1 S,4 S,5 S)-1,4,5-trihydroxyheptadecyl]furan-2-yl}nonyl}-5-methylfuran-2(5 H)-one; 1), muricatetrocin B (= (5 S)-{(2 R)-2-hydroxy-9-{(2 S,5 S)-tetrahydro-5-[(1 S,4 S,5 S)-1,4,5-trihydroxyheptadecyl]furan-2-yl}nonyl}-5-methylfuran-2(5 H)-one; 2), and gigantetrocin B (= (5 S)-3-{(2 R)-2-hydroxy-7-{(2 S,5 S)-tetrahydro-5-[(1 S,4 R,5 R)-1,4,5-trihydroxynonadecyl]furan-2-yl}heptyl}-5-methyl-furan-2(5 H)-one; 3). Their C-skeletons were deduced by mass spectrometry. Configurations were determined by 1H-NMR of ketal derivatives and 2D-NMR experiments utilizing Mosher esters. A previously described compound, gigantetrocin A (= (5 S)-3-{(2 R)-2-hydroxy-7-{(2 S,5 S)-tetrahydro-5-[(1 S,4 S,5 S)-1,4,5-trihydroxynonadecyl]furan-2-yl}heptyl}-5-methylfuran-2-(5 H)one; 4), was also isolated and is new to this species. Compounds 1-4 were all selectively cytotoxic for the HT-29 human colon-tumor cell line with potencies at least 10 times that of adriamycin.
- Publication
Helvetica Chimica Acta, 1993, Vol 76, Issue 7, p2433
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19930760703