Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities

Timofey V Malyarenko; Olesya S Malyarenko Vishchuk; Natalia V Ivanchina; Anatoly I Kalinovsky; Roman S Popov; Alla A Kicha

doi:10.3390/md13074418

Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities

Mar Drugs. 2015 Jul 16;13(7):4418-35. doi: 10.3390/md13074418.

Authors

Timofey V Malyarenko¹, Olesya S Malyarenko Vishchuk², Natalia V Ivanchina³, Anatoly I Kalinovsky⁴, Roman S Popov⁵, Alla A Kicha⁶

Affiliations

¹ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia. [email protected].
² G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia. [email protected].
³ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia. [email protected].
⁴ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia. [email protected].
⁵ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia. [email protected].
⁶ G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia. [email protected].

Abstract

Three new sulfated steroid monoglycosides, leptaochotensosides A-C (1-3), and a new sulfated polyhydroxylated steroid (4) were isolated from the alcoholic extract of the Far Eastern starfish Leptasterias ochotensis. The structures of compounds 1-4 were established by extensive nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESIMS) analyses and chemical transformations. Although the isolated compounds did not show any apparent cytotoxicity against melanoma RPMI-7951 and breast cancer T-47D cell lines, leptaochotensoside A (1) demonstrated inhibition of T-47D cell colony formation in a soft agar clonogenic assay at nontoxic doses. In addition, this compound decreased the epidermal growth factor (EGF)-induced colony formation of mouse epidermal JB6 Cl41 cells. The cancer preventive action of 1 is realized through regulation of mitogen-activated protein kinase (MAPK) signaling pathway.

Keywords: Leptasterias ochotensis; MAPK; cytotoxicity; glycosides; neoplastic cell transformation; starfish; steroids; sulfated steroids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antineoplastic Agents / pharmacology
Breast Neoplasms / drug therapy
Cell Line, Tumor
Cell Proliferation / drug effects
Female
Magnetic Resonance Spectroscopy
Mice
Saponins / chemistry
Saponins / isolation & purification*
Saponins / pharmacology
Spectrometry, Mass, Electrospray Ionization
Starfish / chemistry*

Substances

Antineoplastic Agents
Saponins
leptaochotensoside A