Antialgal activity of several cyanobacterial exometabolites

The isolation of norharmalane (3,4-dihydro-9H-pyrido(3,4-b)indole) from culture media of the cyanobacterium Nodularia harveyana is described. The minimum toxic quantities against selected cyanobacteria of this compound, of the two known cyanobacterial exometabolites 4,4'-dihydroxybiphenyl and norharmane (9H-pyrido(3,4-b)indole) and in addition of harmane (1-methyl-9H-pyrido(3,4-b)indole) were determined using a special TLC plate assay. The three beta-carbolines harmane, norharmane and norharmalane were tested both as bases and as hydrochlorides. All four test compounds were found to be cytotoxic against the cyanobacterial test organisms in low quantities (0.5 to 18.0 mu g). For the beta-carbolines the following structure-response relationships were revealed: the double bond in position 3-4 and possibly the 1-methyl-group increased the cytotoxic effect of these indole alkaloids. Minimum toxic quantities detected for beta-carboline bases were in general lower than those of equimolar amounts of the corresponding hydrochlorides. The possible applicability of both beta-carbolines and biphenyls as agents in antifouling systems is discussed.