Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades

Mar Drugs. 2016 Aug 4;14(8):147. doi: 10.3390/md14080147.

Abstract

Sea cucumbers have been valued for many centuries as a tonic and functional food, dietary delicacies and important ingredients of traditional medicine in many Asian countries. An assortment of bioactive compounds has been described in sea cucumbers. The most important and abundant secondary metabolites from sea cucumbers are triterpene glycosides (saponins). Due to the wide range of their potential biological activities, these natural compounds have gained attention and this has led to their emergence as high value compounds with extended application in nutraceutical, cosmeceutical, medicinal and pharmaceutical products. They are characterized by bearing a wide spectrum of structures, such as sulfated, non-sulfated and acetylated glycosides. Over 700 triterpene glycosides have been reported from the Holothuroidea in which more than 145 are decorated with an acetoxy group having 38 different aglycones. The majority of sea cucumber triterpene glycosides are of the holostane type containing a C18 (20) lactone group and either Δ(7(8)) or Δ(9(11)) double bond in their genins. The acetoxy group is mainly connected to the C-16, C-22, C-23 and/or C-25 of their aglycone. Apparently, the presence of an acetoxy group, particularly at C-16 of the aglycone, plays a significant role in the bioactivity; including induction of caspase, apoptosis, cytotoxicity, anticancer, antifungal and antibacterial activities of these compounds. This manuscript highlights the structure of acetylated saponins, their biological activity, and their structure-activity relationships.

Keywords: Holothuroidea; acetylated triterpene glycosides; anticancer; antifungal; holothurians; holothurin; immunomodulatory; saponins; sea cucumbers.

Publication types

  • Review

MeSH terms

  • Acetylation
  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Biological Products / chemistry
  • Biological Products / pharmacology*
  • Cell Membrane / drug effects
  • Cytotoxins / chemistry
  • Cytotoxins / pharmacology
  • Immunologic Factors / chemistry
  • Immunologic Factors / pharmacology
  • Molecular Structure
  • Saponins / chemistry*
  • Saponins / pharmacology*
  • Sea Cucumbers / chemistry*
  • Sea Cucumbers / classification
  • Structure-Activity Relationship
  • Triterpenes / chemistry*
  • Triterpenes / pharmacology*

Substances

  • Antifungal Agents
  • Antineoplastic Agents
  • Biological Products
  • Cytotoxins
  • Immunologic Factors
  • Saponins
  • Triterpenes