Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Alla A Kicha; Dinh T Ha; Timofey V Malyarenko; Anatoly I Kalinovsky; Roman S Popov; Olesya S Malyarenko; Tran T T Thuy; Pham Q Long; Nguyen T T Ha; Natalia V Ivanchina

doi:10.3390/molecules25061440

Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam

Molecules. 2020 Mar 23;25(6):1440. doi: 10.3390/molecules25061440.

Authors

Affiliations

¹ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia.
² Institute of Natural Products Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
³ Graduate University of Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
⁴ School of Natural Sciences, Far Eastern Federal University, Sukhanova Str. 8, 690000 Vladivostok, Russia.
⁵ Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.

Abstract

Four new polyhydroxylated steroids 1-4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells.

Keywords: Anthenoides laevigatus; NMR spectra; cytotoxicity; polyhydroxylated steroids; soft agar assay; starfish.

MeSH terms

Animals
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / isolation & purification
Antineoplastic Agents* / pharmacology
Cell Proliferation / drug effects*
HT29 Cells
Humans
Molecular Structure
Neoplasms / drug therapy*
Neoplasms / metabolism
Neoplasms / pathology
Nuclear Magnetic Resonance, Biomolecular
Starfish / chemistry*
Steroids* / chemistry
Steroids* / isolation & purification
Steroids* / pharmacology
Vietnam

Substances

Antineoplastic Agents
Steroids

Abstract

MeSH terms

Substances

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