Antibacterial labdane diterpenoids of Ulva fasciata Delile from southwestern coast of the Indian Peninsula

Chromatographic purification of the dichloromethane-soluble fraction of alga, on neutral alumina, using increasing concentrations of ethylacetate/n-hexane as eluents, yielded seven labdane diterpenoids (1-7) as major constituents of green alga Ulva fasciata. Structures of these diterpenoids were established using extensive spectroscopic techniques. Antimicrobial assay showed that the compounds labda-14-ene-3 alpha,8 alpha-diol (2) and labda-14-ene-8 alpha-hydroxy-3-one (4) were inhibitory to the growth of Vibrio parahaemolyticus and Vibrio alginolyticus with minimum inhibitory concentrations of 30 mu g/ml by 2, and 40 mu g/ml by 4, respectively against the former and 30 mu g/ml by 2, and 80 mu g/ml by 4, respectively, against the latter. Structure-activity relationship analyses revealed that the compounds with electronegative hydroxyl or carbonyl group(s) exhibit greater activities, apparently by proton exchange reaction with the basic aminoacyl residue at the macromolecular receptor site of virulent enzymes of pathogenic bacteria. These might provide promising therapeutic agents against infections with multi-resistant Gram-negative fish pathogenic bacteria. (C) 2009 Elsevier Ltd. All rights reserved.