Anti-infective Discorhabdins from a Deep-Water Alaskan Sponge of the Genus Latrunculia

• Type of Material: Article
• Authors: MinKyun Na, University of Mississippi; Yuanqing Ding, University of Mississippi; Bin Wang, University of Mississippi; Babu L. Tekwani, University of Mississippi; Raymond F Schinazi, Emory University; Scott Franzblau, Univ Illinois; Michelle Kelly, Emory University; Robert Stone, NOAA Fisheries; Xing-Cong Li, University of Mississippi; Daneel Ferreira, University of Mississippi; Mark T. Hamann, University of Mississippi
• Language: English
• Date: 2010-03-26
• Publisher: American Chemical Society
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2010 American Chemical Society and American Society of Pharmacognosy.
• Final Published Version (URL): http://dx.doi.org/10.1021/np900281r
• Title of Journal or Parent Work: Journal of Natural Products
• ISSN: 0163-3864
• Volume: 73
• Issue: 3
• Start Page: 383
• End Page: 387
• Grant/Funding Information: Financial support for this project was provided by the NIH (NCRR P20 RR021929, C06 RR1450301, NIAID AI 27094, R-01 AI 36596-12), CDC (NCZVED U01/CI000211), and NSF (EPS-0556308).; R.F.S. is supported in part by a Center for AIDS research NIH grant 2P30-AI050409 and the Department of Veterans Affairs.; The antiprotozoal and antimicrobial assays at NCNPR are supported by the USDA-ARS Agricultural Research Service Specific Cooperative Agreement 58-6408-2-2-0009.
• Keywords: CHEMISTRY, MEDICINAL; PIGMENT; Chemistry, Medicinal; Science & Technology; Life Sciences & Biomedicine; SPECTRA; MARINE SPONGES; Pharmacology & Pharmacy; PLANT SCIENCES; CYTOTOXIC ALKALOIDS; Plant Sciences; ELECTRONIC CIRCULAR-DICHROISM; PHARMACOLOGY & PHARMACY; THEORETICAL CALCULATION
• Research Categories: Chemistry, Pharmaceutical; Health Sciences, Pharmacology

Abstract

Bioassay- and LC-MS-guided fractionation of a methanol extract from a new deep-water Alaskan sponge species of the genus Latrunculia resulted in the isolation of two new brominated pyrroloiminoquinones, dihydrodiscorhabdin B (1) and discorhabdin Y (2), along with six known pyrroloiminoquinone alkaloids, discorhabdins A (3), C (4), E (5), and L (6), dihydrodiscorhabdin C (7), and the benzene derivative 8. Compounds 3, 4, and 7 exhibited anti-HCV activity, antimalarial activity, and selective antimicrobial activity. Although compounds 3 and 7 displayed potent and selective in vitro antiprotozoal activity, Plasmodium berghei-infected mice did not respond to these metabolites due to their toxicity in vivo. © 2010 American Chemical Society and American Society of Pharmacognosy.