Polycavernosides and gambierol: Chemistry, pharmacology, toxicology, and detection

M. Carmen Louzao Ojeda, Eva Cagide Otero, Mari Yamashita, Makoto Sasaki

Research output: Chapter in Book/Report/Conference proceedingChapter

1 Citation (Scopus)

Abstract

Polycavernoside A (PA, Figure 28.1) was isolated by Yasumoto and his colleagues with a minor analog polycavernoside B (PB) as the causative toxin of the human fatal poisoning occurred in Guam in 1991, resulting from ingestion of the red alga Gracilaria edulis.1,2 Out of 13 patients, 3 were killed. PA was also identi6 ed in the same alga that caused the poisoning, killing 8 out of 36 patients in Philippines in 2002-2003.3 The planar structures of PA2 and four minor analogs, polycavernoside A2 (PA2), A3 (PA3), B (PB), and B2 (PB2) (Figure 28.2) were determined.4 All these polycavernosides possess the same macrolide aglycon containing a 6 ve-member cyclohemiacetal adjacent to a ketone at C9. Structural variation among these analogs are in the conjugated diene (PB, PB2) or triene (PA, PA2, PA3) side chain at C15, and in O-methylated or O-acetylated l-fucosyl-d-xylose sugar unit at C5. Yotsu-Yamashita et al. also isolated other two minor analogs, polycavernoside C (PC) and polycavernoside C2 (PC2), from G. edulis collected in Guam in 1991-1992, and their structures were recently determined (Figure 28.1).5 PC and PC2 have a common aglycon structure, that is distinctly different from that of PA and other analogs.

Original languageEnglish
Title of host publicationSeafood and Freshwater Toxins
Subtitle of host publicationPharmacology, Physiology, and Detection, Second Edition
PublisherCRC Press
Pages597-628
Number of pages32
ISBN (Electronic)9781420007541
ISBN (Print)0849374375, 9780849374371
Publication statusPublished - 2008 Jan 1

ASJC Scopus subject areas

  • Engineering(all)
  • Agricultural and Biological Sciences(all)

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