We had previously reported the isolation and characterization of an he
rbicidal metabolite, cyanobacterin, from the freshwater cyanobacterium
(cyanophyte), Scytonema hofmanni UTEX 2349. This compound was identif
ied as a chlorine-containing, diaryl-substituted, gamma-lactone. The n
atural product inhibits electron transport in photosystem II and is to
xic to a number of algae and higher plants. Crude cell extracts of Scy
tonema contain other chlorinated metabolites with biological activity.
We have isolated and characterized a more hydrophilic analog of cyano
bacterin in which an hydroxyl group replaces the methylene dioxy group
on the chlorine-containing aromatic ring. Although it is an effective
inhibitor of photosynthetic electron transport in isolated thylakoid
membranes, the analog has little effect on the growth of intact algal
cells. It readily dehydrates in air at 25 degrees C. The hydroxy analo
g is present in very small quantities in Scytonema cells and is probab
ly a metabolic precursor of cyanobacterin.