Popov RS et al. (2017), Metabolite Profiling of Triterpene Glycosides o...

ECB-ART-45789

Mar Drugs 2017 Oct 02;1510:. doi: 10.3390/md15100302.

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Metabolite Profiling of Triterpene Glycosides of the Far Eastern Sea Cucumber Eupentacta fraudatrix and Their Distribution in Various Body Components Using LC-ESI QTOF-MS.

Popov RS , Ivanchina NV , Silchenko AS , Avilov SA , Kalinin VI , Dolmatov IY , Stonik VA , Dmitrenok PS .

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The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of triterpene glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of triterpene glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography-electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of triterpene glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated glycosides were detected and described. Triterpene glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the triterpene glycosides contents from the five different body components revealed that the profiles of triterpene glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.

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Genes referenced: LOC100887844

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	Figure 1. LC-ESI MS (liquid chromatography–electrospray mass spectrometry) total compounds chromatogram of detected triterpene glycosides in negative ion mode (sulfated, disulfated and non-sulfated glycosides were detected as [M − Na]−, [M − 2Na]2− and [M − H]− ions) in ethanol extract of sea cucumber Eupentacta fraudatrix.
	Figure 2. Structures of triterpene glycosides identified (10, 11, 13, 14, 15, 16, 21, 23, 25, 26, 28, 29, 31, 32, 37, 38, 41, 43, 47, and 48) and proposed (12, 17, 18, 22, 27, 30, 33, 34, 35, 36, 39, 40, 42, 44, 45, 49, 50, 51, and 53) from the sea cucumber E. fraudatrix by LC–MS/MS method.
	Figure 3. ESI MS/MS spectrum of [M + Na]+ precursor ion at m/z 1251 identified as cucumarioside C2 (41).
	Figure 4. Hypothetic scheme of biosynthesis of oligosaccharide chains in E. fraudatrix.
	Figure 5. Relative quantities of triterpene glycosides cucumariosides G1 (32), C1 (37), F1 (38) and C2 (41), and compounds 39, 45, 12, 15, 17, 4, 9, and 40 in respiratory trees (RT), gonads (GN), aquapharyngeal bulbs (AB), guts (G) and body walls (BW) (bar plots represent the concentration in μg/g animal material of metabolites (mean ± SD) scaled by 100%).