Two New Cytotoxic Nonsulfated Pentasaccharide Holostane (=20‐Hydroxylanostan‐18‐oic Acid <i>γ</i>‐Lactone) Glycosides from the Sea Cucumber <i>Holothuria grisea</i>

Sun, Guo-Quan; Li, Ling; Yi, Yang‐Hua; Yuan, Weiping; Liu, Bao‐Shu; Weng, Yiyi; Zhang, Shilong; Sun, Peng; Wang, Zeng‐Lei

doi:10.1002/hlca.200890158

Cited by 28 publications

(24 citation statements)

References 10 publications

(12 reference statements)

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“…These glycosides showed a wide range of biological activities including cytotoxic, antifungal, antiviral, hemolytic, antiprotozoal and immunomodulatory activities. Sea cucumbers produce some major glycosides in sufficient amount to carry out a wide range of biological activity tests [37,94]. Besides major glycosides, they also produce minor glycosides insufficient to test a range of biological activities [66,67].…”

Section: The Important Biological Properties Of Sea Cucumber Glycomentioning

confidence: 99%

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

et al. 2017

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Sea cucumbers belonging to echinoderm are traditionally used as tonic food in China and other Asian countries. They produce abundant biologically active triterpene glycosides. More than 300 triterpene glycosides have been isolated and characterized from various species of sea cucumbers, which are classified as holostane and nonholostane depending on the presence or absence of a specific structural unit γ(18,20)-lactone in the aglycone. Triterpene glycosides contain a carbohydrate chain up to six monosaccharide units mainly consisting of d-xylose, 3-O-methy-d-xylose, d-glucose, 3-O-methyl-d-glucose, and d-quinovose. Cytotoxicity is the common biological property of triterpene glycosides isolated from sea cucumbers. Besides cytotoxicity, triterpene glycosides also exhibit antifungal, antiviral and hemolytic activities. This review updates and summarizes our understanding on diverse chemical structures of triterpene glycosides from various species of sea cucumbers and their important biological activities. Mechanisms of action and structural–activity relationships (SARs) of sea cucumber glycosides are also discussed briefly.

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Section: The Important Biological Properties Of Sea Cucumber Glycomentioning

confidence: 99%

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

et al. 2017

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“…For example, a sensational finding of sulfated tetraosides as the main glycosides in Bohadschia marmorata [28,29], a species studied earlier from different regions of the Indo-Pacific [1,30], that actually has non-sulfated hexaosides as the major components of its glycosidic fraction, may be caused by incorrect taxonomical identification. The clearest case of this is a description of glycosides from Holothuria grisea, a species endemic to the Caribbean and adjacent regions of the Atlantic, but reported as collected in the South China Sea [31]. It is possible that the authors obtained this sea cucumber from the market as dry material because this species is harvested and could be sold in China.…”

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confidence: 99%

Triterpene Glycosides of Sea Cucumbers (Holothuroidea, Echinodermata) as Taxonomic Markers

Kalinin

Avilov

Silchenko

et al. 2015

Natural Product Communications

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Triterpene glycosides are characteristic metabolites of sea cucumbers (Holothurioidea, Echinodermata). The majority of the glycosides belong to the holostane type {lanostane derivatives with an 18(20)-lactone}. Carbohydrate chains of these glycosides contain xylose, glucose, quinovose, 3-O-methylglucose, and, rarely, 3-O-methylxylose, 3-O-methylglucuronic acid, 3-O-methylquinovose, and 6-O-acetyl-glucose. The glycosides are specific for genera, groups of genera and even for species. The advantages and problems in the use of triterpene glycosides as taxonomic markers in the systematics of sea cucumbers are discussed.

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“…It is understood that a primary source tissue for these exogenous saponins is the body wall [ 22 ]. Saponin types can be shared by many species, such as the holothurins A and B [ 5 ], or be very specific, such as the Griseaside A that has so far, only been found in Holothuria grisea [ 45 ]. In our study, we had identified the biosynthesis pathway in the production of Acetyl-CoA (see Figure 3 ), which is a critical metabolite for production of saponins.…”

Section: Resultsmentioning

confidence: 99%

Evidence for a Saponin Biosynthesis Pathway in the Body Wall of the Commercially Significant Sea Cucumber Holothuria scabra

et al. 2017

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The sea cucumber (phylum Echinodermata) body wall is the first line of defense and is well known for its production of secondary metabolites; including vitamins and triterpenoid glycoside saponins that have important ecological functions and potential benefits to human health. The genes involved in the various biosynthetic pathways are unknown. To gain insight into these pathways in an echinoderm, we performed a comparative transcriptome analysis and functional annotation of the body wall and the radial nerve of the sea cucumber Holothuria scabra; to define genes associated with body wall metabolic functioning and secondary metabolite biosynthesis. We show that genes related to signal transduction mechanisms were more highly represented in the H. scabra body wall, including genes encoding enzymes involved in energy production. Eight of the core triterpenoid biosynthesis enzymes were found, however, the identity of the saponin specific biosynthetic pathway enzymes remains unknown. We confirm the body wall release of at least three different triterpenoid saponins using solid phase extraction followed by ultra-high-pressure liquid chromatography-quadrupole time of flight-mass spectrometry. The resource we have established will help to guide future research to explore secondary metabolite biosynthesis in the sea cucumber.

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Two New Cytotoxic Nonsulfated Pentasaccharide Holostane (=20‐Hydroxylanostan‐18‐oic Acid γ‐Lactone) Glycosides from the Sea Cucumber Holothuria grisea

Cited by 28 publications

References 10 publications

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

Triterpene Glycosides of Sea Cucumbers (Holothuroidea, Echinodermata) as Taxonomic Markers

Evidence for a Saponin Biosynthesis Pathway in the Body Wall of the Commercially Significant Sea Cucumber Holothuria scabra

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