Comparison of fascaplysin and related alkaloids: a study of structures, cytotoxicities, and sources.
The fascaplysin class of compounds have been further investigated from six organisms consisting of four sponge collections (Fascaplysinopsis reticulata) and two tunicate collections (Didemnum sp.). This work is an extension of an earlier communication and reports the isolation of 12 new fascaplysin derivatives: 10-bromofascaplysin (7), 3,10-dibromofascaplysin (8), homofascaplysate A (9), homofascaplysin B-1 (11), 3-bromohomofascaplysins B (12), B-1 (13), and C (15), 7,14-dibromoreticulatine (17), reticulatol (20), 14-bromoreticulatol (21), and 3-bromosecofascaplysins A (22) and B (23), along with known compounds: fascaplysin (1), reticulatine (4), 3-bromofascaplysin (6), and homofascaplysin C (14). Selected compounds were screened in a cell-based cytotoxicity assay with compounds 1, 6, and fascaplysin A (24) also screened in the NCI 60 cell line panel. A biogenetic pathway for the brominated fascaplysins and brominated related alkaloids is proposed and discussed.
Segraves
Nathaniel L
NL
Department of Chemistry and Biochemistry and Institute for Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Robinson
Sarah J
SJ
Garcia
Daniel
D
Said
Sadri A
SA
Fu
Xiong
X
Schmitz
Francis J
FJ
Pietraszkiewicz
Halina
H
Valeriote
Frederick A
FA
Crews
Phillip
P
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D004354:Drug Screening Assays, Antitumor; D005367:Fiji; D006801:Humans; D006842:Hydrocarbons, Brominated / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D007214:Indonesia; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D014407:Tumor Cells, Cultured; D014561:Urochordata / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds; D002243:Carbolines; D007212:Indolizines
D000470:Alkaloids; D006842:Hydrocarbons, Brominated; D007211:Indoles; C069346:fascaplysine; D000644:Quaternary Ammonium Compounds; D002243:Carbolines; D007212:Indolizines