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...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-05, Vol.67 (5), p.783-792
Main Authors: Segraves, Nathaniel L, Robinson, Sarah J, Garcia, Daniel, Said, Sadri A, Fu, Xiong, Schmitz, Francis J, Pietraszkiewicz, Halina, Valeriote, Frederick A, Crews, Phillip
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Animals
Biological and medical sciences
Drug Screening Assays, Antitumor
Fiji
General pharmacology
Humans
Hydrocarbons, Brominated - chemistry
Hydrocarbons, Brominated - isolation & purification
Hydrocarbons, Brominated - pharmacology
Indoles - chemistry
Indoles - isolation & purification
Indoles - pharmacology
Indonesia
Inhibitory Concentration 50
Medical sciences
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera - chemistry
Tumor Cells, Cultured
Urochordata - chemistry
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/np049935+