Bromocatechol conjugates from a Chinese marine red alga, Symphyocladia latiuscula

Phytochemistry. 2019 Feb:158:20-25. doi: 10.1016/j.phytochem.2018.10.026. Epub 2018 Nov 15.

Abstract

This study describes an investigation into polybromocatechol conjugates isolated from a marine red alga, Symphyocladia latiuscula (Harvey) Yamada, collected from coastal waters off Qingdao, China. We report on the isolation and characterisation of eight undescribed aconitic acid conjugates, symphyocladins R-X, including a likely solvolysis artifact of symphyocladin S, and an undescribed furanoyl conjugate, symphyocladin Y. Structure elucidation was achieved by detailed spectroscopic analysis. A plausible biosynthetic pathway linking all these co-metabolites through a cascade of quinone methide additions is proposed.

Keywords: Bromocatechol; Bromophenol; Natural products; Quinone methide; Red alga; Symphyocladia latiuscula (Rhodomelaceae).

MeSH terms

  • Aconitic Acid / chemistry*
  • Aconitic Acid / pharmacology
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Catechols / chemistry*
  • Catechols / pharmacology
  • China
  • Furans / chemistry*
  • Furans / pharmacology
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Rhodophyta / chemistry*
  • Rhodophyta / metabolism
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Anti-Infective Agents
  • Catechols
  • Furans
  • Aconitic Acid