Silchenko AS et al. (2023), Chilensosides E, F, and G-New Tetrasulfated Tri...

ECB-ART-51593

Mar Drugs 2023 Feb 05;212:. doi: 10.3390/md21020114.

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Chilensosides E, F, and G-New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis.

Silchenko AS , Avilov SA , Popov RS , Dmitrenok PS , Chingizova EA , Grebnev BB , Rasin AB , Kalinin VI .

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Three new tetrasulfated triterpene glycosides, chilensosides E (1), F (2), and G (3), have been isolated from the Far-Eastern sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds differ in their carbohydrate chains, namely in the number of monosaccharide residues (five or six) and in the positions of sulfate groups. Chilensosides E (1) and F (2) are tetrasulfated pentaosides with the position of one of the sulfate groups at C-3 Glc3, and chilensoside G (3) is a tetrasulfated hexaoside. The biogenetic analysis of the glycosides of P. chilensis has revealed that the structures form a network due to the attachment of sulfate groups to almost all possible positions. The upper semi-chain is sulfated earlier in the biosynthetic process than the lower one. Noticeably, the presence of a sulfate group at C-3 Glc3-a terminal monosaccharide residue in the bottom semi-chain of compounds 1 and 2-excludes the possibility of this sugar chain's further elongation. Presumably, the processes of glycosylation and sulfation are concurrent biosynthetic stages. They can be shifted in time in relation to each other, which is a characteristic feature of the mosaic type of biosynthesis. The hemolytic action of compounds 1-3 against human erythrocytes and cytotoxic activities against five human cancer cell lines were tested. The compounds showed moderate hemolytic activity but were inactive against cancer cells, probably because of their structural peculiarities, such as the combination of positions of four sulfate groups.

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References [+] :

Honey-Escandón, Biological and taxonomic perspective of triterpenoid glycosides of sea cucumbers of the family Holothuriidae (Echinodermata, Holothuroidea). 2015, Pubmed, Echinobase

	Figure 1. Chemical structures of glycosides isolated from Paracaudina chilensis: 1—chilensoside E; 2—chilensoside F; 3—chilensoside G.
	Figure 2. Key ROE- (A), HMBC and COSY (B) correlations of chilensoside E. The oxygen atoms have marked with red color.
	Figure 3. The directions of sulfation in the process of biosynthesis of the glycosides of P. chilensis. Uncombined biogenetic rows are highlighted by blue and red colors.