Algicidal Sesquiterpene Hydroquinones from the Brown AlgaDictyopteris undulata

Abstract

Bioassay-guided fractionation of a methanol extract of the brown alga, Dictyopteris undulata, led to the isolation of a novel sesquiterpene hydroquinone named zonarenone, together with seven known sesquiterpene hydroquinones, zonarol, isozonarol, yahazunol, zonaroic acid, chromazonarol, isochromazonarol, and 2-(3,7,11-trimethyl-2,6,10-dodecatrienyl)hydroquinone. The structure of zonarenone was elucidated on the basis of spectroscopic information. The isolated compounds, excepting zonaroic acid, showed moderate to high cell lysis activity against the red tide microalgal species, Heterosigma akashiwo and Heterocapsa circularisquama, at a concentration of 1 g/mL.

Bioactivities of algicidal C18 hydroxy unsaturated fatty acid isolated from the red alga Tricleocarpa jejuensis and its synthesized propargylic derivative

“…In fact, diverse chemical compounds with growth inhibitory effects on HAB species have been found in several marine macroalgal species. Such compounds discovered so far are polyunsaturated fatty acid related compounds (PUFAs) [14][15][16][17], glycerolipids [18][19][20], terpenoids [8,[21][22][23][24], and phenolics [8,24].…”

Marine Hydroquinone Zonarol Prevents Inflammation and Apoptosis in Dextran Sulfate Sodium-Induced Mice Ulcerative Colitis

“…The absolute chemical structure of the sesquiterpene was elucidated in 1986 [16] . Other pharmacological actions of zonarol have been reported, such as antioxidant effects [17] , phospholipase inhibition [18] , feeding deterrents against abalone [19] and algicidal effects [20] . To the best of our knowledge, there are no data regarding the in vivo effects of the marine hydroquinone, zonarol, especially with regard to its anti-inflammatory effects.…”

Natural sesquiterpene quinone/quinols: chemistry, biological activity, and synthesis

“…52 Cell lysisguided chromatographic fractionation of the extract from Dictyopteris undulata has led to the identication of zonarenone (30) and isozonaroic acid (31). 53,54 The absolute conguration of 31 was established to be 5R, 9R, and 10R on comparing its optical rotation with that of its methyl ester, which was synthesized via the triation of one hydroxy group in isozonarol, followed by palladium-catalyzed alkoxycarbonylation. Dysidphenol C (32) and highly polar siphonodictyal A sulfate (33) were identied from the marine sponges Dysidea sp.…”