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ARS Home » Southeast Area » Oxford, Mississippi » Natural Products Utilization Research » Research » Publications at this Location » Publication #215109
Title: Synthesis of Water-soluble 9,10-Anthraquinone Analogues with Potent Cyanobactericidal Activity Toward the Musty-Odor Cyanobacterium Oscillatoria perornata

Author
item NANAYAKKARA, DHAMMIKA N.P. - UNIVERSITY OF MISSISSIPPI
item Schrader, Kevin

Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 11/30/2007
Publication Date: 1/19/2008
Citation: Nanayakkara, D., Schrader, K. 2008. Synthesis of Water-soluble 9,10-Anthraquinone Analogues with Potent Cyanobactericidal Activity Toward the Musty-Odor Cyanobacterium Oscillatoria perornata. Journal of Agricultural and Food Chemistry. 56:1002-1007.

Interpretive Summary: Water-soluble analogs were made of a natural compound found to have selective toxicity towards the blue-green alga which causes "musty" off-flavor in pond-raised channel catfish in Mississippi, Alabama, and Arkansas. The water-soluble forms of the natural compound were evaluated to determine which ones were most selectively toxic towards the musty blue-green alga and in relation to the chemical nature of the analog compound.

Technical Abstract: A series of water-soluble 9,10-anthraquinone analogs were prepared and evaluated for their selective toxicity towards Oscillatoria perornata which grows in catfish production ponds and causes “musty” off-flavor in channel catfish Ictalurus punctatus. Water-soluble mono- and dicationic salts were prepared by conjugating various small amines directly or through a methylene or ethylene bridge to the 9,10-anthraquinone nucleus. One of the dicationic salts, 2-[N-(1´-methyl-4´-N,N-diethylaminobutyl)aminometyl]anthraquinone diphosphate exhibited very high water solubility and potent selective toxicity towards O. perornata. However, the tendency of this compound to potentially bind to suspended sediments may be the reason for its limitations in controlling O. perornata in catfish production ponds. Monocationic salt, 2-[N-(1´-methylethyl)]aminomethyl]anthraquinone monophosphate, showed good solubility and high selective toxicity towards O. perornata. Neutral water-soluble analogs prepared by conjugating terta- or pentaethylene glycol directly or by a methylene bridge to the 9,10-anthraquinone nucleus had less activity than the parent compound.