Cargando…

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

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 da...

Descripción completa

Detalles Bibliográficos
Autores principales: Silchenko, Alexandra S., Avilov, Sergey A., Popov, Roman S., Dmitrenok, Pavel S., Chingizova, Ekaterina A., Grebnev, Boris B., Rasin, Anton B., Kalinin, Vladimir I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9964569/
https://www.ncbi.nlm.nih.gov/pubmed/36827155
http://dx.doi.org/10.3390/md21020114
_version_ 1784896538940538880
author Silchenko, Alexandra S.
Avilov, Sergey A.
Popov, Roman S.
Dmitrenok, Pavel S.
Chingizova, Ekaterina A.
Grebnev, Boris B.
Rasin, Anton B.
Kalinin, Vladimir I.
author_facet Silchenko, Alexandra S.
Avilov, Sergey A.
Popov, Roman S.
Dmitrenok, Pavel S.
Chingizova, Ekaterina A.
Grebnev, Boris B.
Rasin, Anton B.
Kalinin, Vladimir I.
author_sort Silchenko, Alexandra S.
collection PubMed
description 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.
format Online
Article
Text
id pubmed-9964569
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-99645692023-02-26 Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis Silchenko, Alexandra S. Avilov, Sergey A. Popov, Roman S. Dmitrenok, Pavel S. Chingizova, Ekaterina A. Grebnev, Boris B. Rasin, Anton B. Kalinin, Vladimir I. Mar Drugs Article 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. MDPI 2023-02-05 /pmc/articles/PMC9964569/ /pubmed/36827155 http://dx.doi.org/10.3390/md21020114 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Silchenko, Alexandra S.
Avilov, Sergey A.
Popov, Roman S.
Dmitrenok, Pavel S.
Chingizova, Ekaterina A.
Grebnev, Boris B.
Rasin, Anton B.
Kalinin, Vladimir I.
Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
title Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
title_full Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
title_fullStr Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
title_full_unstemmed Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
title_short Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
title_sort chilensosides e, f, and g—new tetrasulfated triterpene glycosides from the sea cucumber paracaudina chilensis (caudinidae, molpadida): structures, activity, and biogenesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9964569/
https://www.ncbi.nlm.nih.gov/pubmed/36827155
http://dx.doi.org/10.3390/md21020114
work_keys_str_mv AT silchenkoalexandras chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT avilovsergeya chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT popovromans chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT dmitrenokpavels chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT chingizovaekaterinaa chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT grebnevborisb chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT rasinantonb chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis
AT kalininvladimiri chilensosidesefandgnewtetrasulfatedtriterpeneglycosidesfromtheseacucumberparacaudinachilensiscaudinidaemolpadidastructuresactivityandbiogenesis