Journal of Applied Phycology

, Volume 18, Issue 2, pp 145–151 | Cite as

Antialgal Activity of Several Cyanobacterial Exometabolites

  • Rainer -B. Volk
Original Article


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 β-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 μg). For the β-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 β-carboline bases were in general lower than those of equimolar amounts of the corresponding hydrochlorides. The possible applicability of both β-carbolines and biphenyls as agents in antifouling systems is discussed.


4,4′-dihydroxybiphenyl β-carbolines Cytotoxicity Harmane Indole alkaloid Norharmalane Norharmane 


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Copyright information

© Springer Science+Business Media B.V. 2006

Authors and Affiliations

  1. 1.Pharmazeutisches Institut, Abteilung Pharmazeutische BiologieUniversität KielKielGermany

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