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Citation
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HERO ID
2880199
Reference Type
Journal Article
Title
New antiinfective and human 5-HT2 receptor binding natural and semisynthetic compounds from the Jamaican sponge Smenospongia aurea
Author(s)
Hu, JF; Schetz, JA; Kelly, M; Peng, JN; Ang, KKH; Flotow, H; Leong, CY; Ng, SB; Buss, AD; Wilkins, SP; Hamann, MT
Year
2002
Is Peer Reviewed?
Yes
Journal
Journal of Natural Products
ISSN:
0163-3864
EISSN:
1520-6025
Volume
65
Issue
4
Page Numbers
476-480
Language
English
PMID
11975483
DOI
10.1021/np010471e
Web of Science Id
WOS:000175327700009
Abstract
In addition to the sesquiterpene-phenol aureols (1), 6'-chloroaureol (2), and aureol acetate (3), eight indole alkaloids including the new N-3'-ethylaplysinopsin (9) have been isolated from the Jamaican sponge Smenospongia aurea. Makaluvamine O (10), a new member of the pyrroloiminoquinone class, was also isolated. The structures were characterized by spectroscopic methods, and two new derivatives of aureol were prepared to optimize the biological activity. Aureol N,N-dimethyl thiocarbamate (1a) and 6-bromoaplysinopsin (7) exhibit significant antimalarial and antimycobacterial activity in vitro. Compound 6 showed activity against the Plasmodium enzyme plasmepsin II. The 6-bromo-2'-de-N-methylaplysinopsin (6), 6-bromoaplysinopsin (7), and N-3'-ethylaplysinopsin (9) displaced high-affinity [(3)H]antagonist ligands from cloned human serotonin 5-HT(2) receptor subtypes, whereas the other compounds tested did not. Remarkably, the 6-bromo-2'-de-N-methylaplysinopsin (6) showed a > 40-fold selectivity for the 5-HT(2C) subtype over the 5-HT(2A) subtype.
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