Symphyocladins A-G: Bromophenol adducts from a Chinese marine red alga, Symphyocladia latiuscula

Xiuli Xu, Andrew M. Piggott, Liyuan Yin, Robert J. Capon*, Fuhang Song

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

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 10 μg/mL) against Candida albicans.

Original languageEnglish
Pages (from-to)2103-2106
Number of pages4
JournalTetrahedron Letters
Volume53
Issue number16
DOIs
Publication statusPublished - 18 Apr 2012
Externally publishedYes

Keywords

  • Bromophenols
  • Marine red algae
  • Natural products chemistry
  • Symphyocladia latiuscula

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