Application of metabolomics approaches for the analysis of secondary metabolites of starfish and sea cucumbers at the G.B. Elyakov Pacific Institute of Bioorganic Chemistry, FEB RAS

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Abstract

Polar steroidal compounds of starfish and triterpene glycosides of sea cucumbers are unique biologically active secondary metabolites with unusual chemical structures and diverse biological effects. The application of metabolomic approaches involving mass spectrometry techniques to the investigation of marine invertebrate extracts makes it possible to detect many previously unstudied, including minor, compounds, to rapidly characterize a complete set of metabolites, to identify known compounds and to infer structures or to obtain information on the structure of specific parts of molecules for new compounds. The article briefly discusses key achievements in the study of secondary metabolites of starfish and sea cucumbers using metabolomic approaches at the G.B. Elyakov Pacific Institute of Bioorganic Chemistry, FEB RAS. The use of mass spectrometry-based approaches to investigate total fractions of polar steroidal compounds from the Far Eastern starfish Aphelasterias japonica (class Asteroidea, order Forcipulatida, family Asteriidae), Patiria pectinifera (class Asteroidea, order Valvatida, family Asterinidae) and Lethasterias fusca (class Asteroidea, order Forcipulatida, family Asteriidae) allowed the detection and structural characterization of a large number of both known and novel steroidal compounds, including asterosaponins, polyhydroxysteroid glycosides and polyhydroxysteroids. In addition, the effect of different stress factors on the steroid metabolome of P. pectinifera and the distribution of detected compounds in different organs of L. fusca were studied. The data obtained allowed us to draw conclusions about the biosynthesis and the biological functions of these metabolites. The application of metabolomic profiling allowed us to characterize the composition of triterpene glycosides of the Far Eastern sea cucumber Eupentacta fraudatrix (class Holothuroidea, order Dendrochirotida, family Sclerodactylidae) and to propose a scheme of their biosynthesis. Based on the data obtained, a spectral library was created for a large number of previously isolated triterpene glycosides.

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About the authors

Roman S. Popov

Elyakov Pacific Institute of Bioorganic Chemistry of FEB RAS

Author for correspondence.
Email: rs.popov@outlook.com
ORCID iD: 0000-0002-1727-6164

Candidate of Sciences in Chemistry, Senior Researcher

Russian Federation, Vladivostok

Natalia V. Ivanchina

Elyakov Pacific Institute of Bioorganic Chemistry of FEB RAS

Email: ivanchina@piboc.dvo.ru
ORCID iD: 0000-0001-9075-8584

Candidate of Sciences in Chemistry, Head of Laboratory

Russian Federation, Vladivostok

Pavel S. Dmitrenok

Elyakov Pacific Institute of Bioorganic Chemistry of FEB RAS

Email: paveldmt@piboc.dvo.ru
ORCID iD: 0000-0002-8191-6170

Doctor of Sciences in Chemistry, Director

Russian Federation, Vladivostok

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Supplementary files

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2. Fig. 1. MS/MS spectrum of the [M - Na]- ion at m / z 1213.5 of the asterosaponin ophidianoside F

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3. Fig. 2. Ion current chromatogram of steroidal compounds detected in P. pectinifera extract obtained in the negative ion registration mode

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4. Fig. 3. Ion current chromatogram of steroidal compounds detected in L. fusca extract obtained in negative ion registration mode

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5. Fig. 4. MS/MS spectrum of the [M + Na]+ ion at m / z 1251.58 of the triterpene glycoside cucumarioside C2

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6. Fig. 5. Results of molecular network analysis with subsequent identification and annotation of triterpene glycosides detected in the extract of E. fraudatrix holothuria using the created database

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