Chemical fingerprinting and phylogenetic mapping of saponin congeners from three tropical holothurian sea cucumbers

Karen Grace V Bondoc, Hyeyoung Lee, Lourdes J. Cruz, Carlito B Lebrilla, Marie Antonette Juinio-Meñez

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

Holothurians are sedentary marine organisms known to produce saponins (triterpene glycosides), secondary metabolites exhibiting a wide range of biological activities. In this paper, we investigated the saponin contents of semi-purified and membranolytic HPLC fractionated extracts from the body wall of three species of Holothuriidae as an attempt to examine its chemical diversity in relation to phylogenetic data. MALDI-FTICR MS and nano-HPLC-chip Q-TOF MS were used for mass profiling and isomer separation, respectively giving a unique chemical saponin fingerprint. Moreover, the methods used yield the highest number of congeners. However, saponin concentration, bioactivity and chemical diversity had no apparent relationship. MS fingerprint showed the presence of holothurinosides, which was observed for the first time in other Holothuria genera besides the basally positioned Holothuria forskali. This congener is proposed to be a primitive character that could be used for taxonomic purposes. The phylogenetic mapping also showed that the glycone part of the compound evolved from non-sulfated hexaosides to sulfated tetraosides, which have higher membranolytic activity and hydrophilicity, the two factors affecting the total ecological activity (i.e. chemical defense) of these compounds. This might be an adaptation to increase the fitness of the organism.

Original languageEnglish (US)
Pages (from-to)182-193
Number of pages12
JournalComparative Biochemistry and Physiology - B Biochemistry and Molecular Biology
Volume166
Issue number3-4
DOIs
StatePublished - Nov 2013

Keywords

  • Chemical taxonomy
  • Holothuriidae
  • Mass spectrometry
  • Phylogenetics
  • Saponin

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Physiology

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