Three new pseudodistomins, piperidine alkaloids from the ascidian Pseudodistoma megalarva.
Bioassay-guided fractionation of the MeOH-CH2Cl2 extract of the Micronesian ascidian Pseudodistoma megalarva yielded three new piperidine alkaloids, pseudodistomins D-F (3-5) and the previously reported pseudodistomins B and C (1 and 2). The structure and stereochemistry of these compounds were established by interpretation of spectral data. Pseudodistomins B-F were found to be active in a cell-based assay for DNA damage induction, but the activity was due to an alternative mechanism.
Freyer
A J
AJ
Department of Biomolecular Discovery, SmithKline Beecham Pharmaceuticals, R & D, King of Prussia, Pennsylvania 19406-0939, USA. Alan_J_Freyer@sbphrd.com
Patil
A D
AD
Killmer
L
L
Troupe
N
N
Mentzer
M
M
Carte
B
B
Faucette
L
L
Johnson
R K
RK
D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D002855:Chromatography, Thin Layer; D004260:DNA Repair / Q000187:drug effects; D004271:DNA, Fungal / Q000096:biosynthesis; D009682:Magnetic Resonance Spectroscopy; D009152:Mutagenicity Tests; D009153:Mutagens / Q000302:isolation & purification* / Q000494:pharmacology; D010880:Piperidines / Q000302:isolation & purification* / Q000494:pharmacology; D014561:Urochordata / Q000737:chemistry*; D015003:Yeasts / Q000187:drug effects / Q000235:genetics
D000470:Alkaloids; D004271:DNA, Fungal; D009153:Mutagens; D010880:Piperidines; C109385:pseudodistomin D; C109386:pseudodistomin E; C109387:pseudodistomin F