ECB-ART-45817
Mar Drugs
2017 Oct 17;1510:. doi: 10.3390/md15100317.
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Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties.
Mondol MAM
,
Shin HJ
,
Rahman MA
,
Islam MT
.
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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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Genes referenced: LOC100887844 sars1
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Figure 1. Structures of lanostane, holostane and holostanol. |
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Figure 2. Common sugar units present in sea cucumber glycosides. |
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Figure 3. Some common carbohydrate architectures found in sea cucumber glycosides. |
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Figure 4. Pentacyclic triterpene and alkane side chain skeletons are commonly found in holostane type glycosides. (a) Pentacylic triterpene skeletons. Substitution by selective functional groups and unsaturation generally take place in the alkane side chain (2-methylpentane) attached to C-20 of the E-ring of aglycone; (b) Alkane side chain architectures. |
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Figure 5. Chemical structures of holostane glycosides with 3β-hydroxyholost-7(8)-ene and six sugar units. |
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Figure 6. Chemical structures of holostane glycosides with 3β-hydroxyholost-7(8)-ene and five sugar units. |
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Figure 7. Chemical structures of holostane glycosides with 3β-hydroxyholost-7(8)-ene and four sugar units. |
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Figure 8. Chemical structures of holostane glycosides with 3β-hydroxyholost-7(8)-ene and 1–3 sugar units. |
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Figure 9. Chemical structures of holostane glycosides with 3β-hydroxyholost-9(11)-ene and six sugar units. |
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Figure 10. Chemical structures of holostane glycosides with 3β-hydroxyholost-9(11)-ene and five sugar units. |
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Figure 11. Chemical structures of holostane glycosides with 3β-hydroxyholost-9(11)-ene and fours ugar units. |
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Figure 12. Chemical structure of holostane glycosides with 3β-hydroxyholost-9(11)-ene and 1–3 sugar units. |
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Figure 13. Chemical structures of holostane glycosides with 3β-hydroxyholost-8(9)-ene skeleton. |
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Figure 14. D- and E-ring structural architectures present in nonholotane glycosides. |
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Figure 15. Chemical structures of nonholostane glycosides. |
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