Planta Med 2008; 74 - PB34
DOI: 10.1055/s-0028-1084379

Anti-infective pyrroloiminoquinone alkaloids from a deep-water Alaskan sponge of the genus Latrunculia

MK Na 1, RF Schinazi 2, M Kelly 3, R Stone 4, MT Hamann 5
  • 1College of Pharmacy, Yeungnam University, Gyeongsan, Gyeongbuk 712–749, South Korea
  • 2Department of Pediatrics, Emory University/VA Medical Center, Decatur, GA 30033, USA
  • 3National Centre for Aquatic Biodiversity and Biosecurity, National Institute of Water and Atmospheric Research (NIWA), Private Bag 109695, Auckland, New Zealand
  • 4NOAA Fisheries, Alaska Fisheries Science Center, Auke Bay Lab, 11305 Glacier Highway, Juneau, AK 99801, USA
  • 5Department of Pharmacognosy & The National Center for Natural Products Research, The University of Mississippi, University, MS 38677, USA

Bioassay- and LC-MS-guided fractionation of a methanol extract from a new deep-water Alaskan sponge species of the genus Latrunculia (Class Demospongiae: Order Poecilosclerida: Family Latrunculiidae), resulted in the isolation of two new brominated pyrroloiminoquinones, discorhabdins X (3) and Y (6), along with six known pyrroloiminoquinone alkaloids, discorhabdins A (1), C (4), E (5), L (8), 3-dihydrodiscorhabdin C (2), and a benzene derivative (7). The anti-infective properties of major isolates 1, 2, and 4 were evaluated using some selected in vitro assays. Compounds 1, 2, and 4 displayed anti-HCV activity with EC50 values less than 10µM, and showed antimalarial activity against both the chloroquine-susceptible (D6) and -resistant (W2) clones of Plasmodium falciparum, with IC50 values ranging from 22 to 1300ng/ml, as well as exhibited selective antimicrobial activity against AIDS opportunistic pathogens, Methicillin Resistance Staphylococcus aureus (MRSA), Mycobacterium intracellulare, and M. tuberculosis. Although compounds 1 and 2 displayed potent and selective in vitro antiprotozoal activity, P. berghei infected mice did not respond to these metabolites due to their toxicity.

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