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

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 reson...

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Main Authors:	Timofey V. Malyarenko, Olesya S. Malyarenko (Vishchuk), Natalia V. Ivanchina, Anatoly I. Kalinovsky, Roman S. Popov, Alla A. Kicha
Format:	Article
Language:	English
Published:	MDPI AG 2015-07-01
Series:	Marine Drugs
Subjects:	steroids sulfated steroids glycosides starfish Leptasterias ochotensis cytotoxicity neoplastic cell transformation MAPK
Online Access:	http://www.mdpi.com/1660-3397/13/7/4418

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spelling	doaj-d8a97f981a92487ea1c990be31f3c42b2020-11-24T23:31:16ZengMDPI AGMarine Drugs1660-33972015-07-011374418443510.3390/md13074418md13074418Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and ActivitiesTimofey V. Malyarenko0Olesya S. Malyarenko (Vishchuk)1Natalia V. Ivanchina2Anatoly I. Kalinovsky3Roman S. Popov4Alla A. Kicha5G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, RussiaThree 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.http://www.mdpi.com/1660-3397/13/7/4418steroidssulfated steroidsglycosidesstarfishLeptasterias ochotensiscytotoxicityneoplastic cell transformationMAPK
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Timofey V. Malyarenko Olesya S. Malyarenko (Vishchuk) Natalia V. Ivanchina Anatoly I. Kalinovsky Roman S. Popov Alla A. Kicha
spellingShingle	Timofey V. Malyarenko Olesya S. Malyarenko (Vishchuk) Natalia V. Ivanchina Anatoly I. Kalinovsky Roman S. Popov Alla A. Kicha Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities Marine Drugs steroids sulfated steroids glycosides starfish Leptasterias ochotensis cytotoxicity neoplastic cell transformation MAPK
author_facet	Timofey V. Malyarenko Olesya S. Malyarenko (Vishchuk) Natalia V. Ivanchina Anatoly I. Kalinovsky Roman S. Popov Alla A. Kicha
author_sort	Timofey V. Malyarenko
title	Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities
title_short	Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities
title_full	Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities
title_fullStr	Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities
title_full_unstemmed	Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities
title_sort	four new sulfated polar steroids from the far eastern starfish leptasterias ochotensis: structures and activities
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2015-07-01
description	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.
topic	steroids sulfated steroids glycosides starfish Leptasterias ochotensis cytotoxicity neoplastic cell transformation MAPK
url	http://www.mdpi.com/1660-3397/13/7/4418
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Four New Sulfated Polar Steroids from the Far Eastern Starfish Leptasterias ochotensis: Structures and Activities

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