title: Acetylated Triterpene Glycosides and Their Biological Activity from Holothuroidea Reported in the Past Six Decades.
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.
authors.affiliation: Medical Biotechnology, Flinders Medical Science and Technology, School of Medicine, Flinders University, Adelaide SA 5042, Australia. ybahrami@mbrc.ac.ir.|Centre for Marine Bioproducts Development, Flinders University, Adelaide SA 5042, Australia. ybahrami@mbrc.ac.ir.|Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah 6714415185, Iran. ybahrami@mbrc.ac.ir.
authors.forename: Yadollah
authors.initials: Y
authors.lastname: Bahrami
authors.affiliation: Medical Biotechnology, Flinders Medical Science and Technology, School of Medicine, Flinders University, Adelaide SA 5042, Australia. yadollah.bahrami@flinders.edu.au.|Centre for Marine Bioproducts Development, Flinders University, Adelaide SA 5042, Australia. yadollah.bahrami@flinders.edu.au.
authors.forename: Christopher M M
authors.initials: CM
authors.lastname: Franco
mesh_terms: D000107:Acetylation; D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000737:chemistry / Q000494:pharmacology*; D002462:Cell Membrane / Q000187:drug effects; D003603:Cytotoxins / Q000737:chemistry / Q000494:pharmacology; D007155:Immunologic Factors / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology*; D012616:Sea Cucumbers / Q000737:chemistry* / Q000145:classification; D013329:Structure-Activity Relationship; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000935:Antifungal Agents; D000970:Antineoplastic Agents; D001688:Biological Products; D003603:Cytotoxins; D007155:Immunologic Factors; D012503:Saponins; D014315:Triterpenes
keywords: Holothuroidea; acetylated triterpene glycosides; anticancer; antifungal; holothurians; holothurin; immunomodulatory; saponins; sea cucumbers