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Steroid compounds from pacific starfish Mithrodia clavigera and their toxicity to human melanoma cells

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Abstract

A new sulfated polyoxide steroid (20S)-3β,6α,20-trihydroxi-5α-cholest-9(11)-ene 3-sulfate (sodium salt) named mithrotriol was isolated from the Pacific starfish Mithrodia clavigera. Additionally, six previously known compounds were isolated and identified including glycosides echinasteroside B, granulatoside A, linckoside K, and forbeside L, as well as sulfates of thornasterol A and cholesterol. The structure of mithrotriol was elucidated by NMR (1H, 13C, DEPT, COSY-45, NOESY, HSQC, and HMBC) and massspectrometry. Minimal inhibitory concentrations were determined for the isolated compounds that demonstrated cytotoxic activity in human melanoma cells SK-MEL-28, SK-MEL-5, and RPMI-7951.

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Abbreviations

COSY:

correlation spectroscopy, two dimensional shift correlations via spin-spin interaction

DEPT:

the method of 13C NMR spectra recording allowing us to distinguish C, CH, CH2, CH3 fragments

HMBC:

heteronuclear CH-correlation within multiple bonds

HSQC:

heteronuclear single quantum correlation of XH interactions within one bond

NOE:

Nuclear Overhauser effect spectroscopy

FBS:

fetal bovine serum

DMEM medium:

Dulbecco’s Modifies Eagle Medium

IC50 :

concentration causing 50% cell death

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Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, pr. 100-Letiya Vladivostoka 159, Vladivostok, 690022, Russia

    E. V. Levina, A. I. Kalinovskii, S. P. Ermakova & P. S. Dmitrenok

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  1. E. V. Levina
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  2. A. I. Kalinovskii
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  3. S. P. Ermakova
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  4. P. S. Dmitrenok
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Correspondence to E. V. Levina.

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Original Russian Text © E.V. Levina, A.I. Kalinovskii, S.P. Ermakova, P.S. Dmitrenok, 2012, published in Bioorganicheskaya Khimiya, 2012, Vol. 38, No. 5, pp. 591–596.

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Levina, E.V., Kalinovskii, A.I., Ermakova, S.P. et al. Steroid compounds from pacific starfish Mithrodia clavigera and their toxicity to human melanoma cells. Russ J Bioorg Chem 38, 520–525 (2012). https://doi.org/10.1134/S1068162012050093

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  • DOI: https://doi.org/10.1134/S1068162012050093

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