Rare Ophiuroid-Type Steroid 3β,21-, 3β,22-, and 3α,22-Disulfates from the Slime Sea Star Pteraster marsippus and Their Colony-Inhibiting Effects against Human Breast Cancer Cells
-
Published:2024-01-12
Issue:1
Volume:22
Page:43
-
ISSN:1660-3397
-
Container-title:Marine Drugs
-
language:en
-
Short-container-title:Marine Drugs
Author:
Kicha Alla A.1ORCID, Malyarenko Timofey V.12ORCID, Kuzmich Alexandra S.1, Malyarenko Olesya S.1ORCID, Kalinovsky Anatoly I.1, Popov Roman S.1, Tolkanov Dmitriy K.1, Ivanchina Natalia V.1ORCID
Affiliation:
1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia 2. Department of Bioorganic Chemistry and Biotechnology, School of Natural Sciences, Far Eastern Federal University, Russky Island, Ajax Bay, 10, 690922 Vladivostok, Russia
Abstract
Two new steroid 3β,21-disulfates (1, 2) and two new steroid 3β,22- and 3α,22-disulfates (3, 4), along with the previously known monoamine alkaloid tryptamine (5) were found in the ethanolic extract of the Far Eastern slime sea star Pteraster marsippus. Their structures were determined on the basis of detailed analysis of one-dimensional and two-dimensional NMR, HRESIMS, and HRESIMS/MS data. Compounds 1 and 2 have a Δ22-21-sulfoxy-24-norcholestane side chain. Compounds 3 and 4 contain a Δ24(28)-22-sulfoxy-24-methylcholestane side chain, which was first discovered in the polar steroids of starfish and brittle stars. The influence of substances 1–4 on cell viability, colony formation, and growth of human breast cancer T-47D, MCF-7, and MDA-MB-231 cells was investigated. It was shown that compounds 1 and 2 possess significant colony-inhibiting activity against T-47D cells, while compounds 3 and 4 were more effective against MDA-MB-231 cells.
Subject
Drug Discovery,Pharmacology, Toxicology and Pharmaceutics (miscellaneous),Pharmaceutical Science
Reference30 articles.
1. Steroid oligoglycosides and polyhydroxysteroids from Echinoderms;Minale;Fortschr. Chem. Org. Naturst.,1993 2. Steroidal oligoglycosides from the Asteroidea;Iorizzi;Curr. Org. Chem.,2001 3. Chemical constituents and bioactivities of starfish;Dong;Chem. Biodivers.,2011 4. Xia, J.M., Miao, Z., Xie, C.L., Zhang, J.W., and Yang, X.W. (2020). Chemical constituents and bioactivities of starfishes: An update. Chem. Biodivers., 17. 5. Chapter 1—Echinoderms: A Review of Bioactive Compounds with Potential Health Effects;Studies in Natural Products Chemistry,2016
|
|