Symphyocladins A–G: bromophenol adducts from a Chinese marine red alga, Symphyocladia latiuscula

Abstract: Chemical analysis of a Chinese collection of the marine red alga Symphyocladia latiuscula yielded five unprecedented bromophenol–aconitic acid adducts, symphyocladins A–E, together with a new example of a bromophenol–pyroglutamic acid adduct, symphyocladin F, a new example of a bromophenol–urea adduct, symphyocladin G, and the known methyl ester of cis-aconitic acid. The structures were assigned on the basis of detailed spectroscopic analysis, and were consistent with a plausible biosynthetic pathway linking these bromophenol natural products with a putative quinone methide intermediate. Symphyocladins A/B and C/D were isolated as inseparable 1:1 mixtures of E/Z isomers. A plausible mechanism for their facile equilibration during handling and storage is presented. The bromophenol–urea exhibits antifungal activity (MIC 10μg/mL) against Candida albicans. [Copyright &y& Elsevier]