Comparative study on polyhydroxylated steroids from echinoderms

Shubina, Larisa K.; Fedorov, Sergey N.; Levina, E. V.; Andriyaschenko, P.V.; Kalinovsky, Anatoly I.; Stonik, Valentin A.; Смирнов, И. С.

doi:10.1016/s0305-0491(98)00011-x

Cited by 13 publications

(15 citation statements)

References 15 publications

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“…Such steroids have been described for instance in the leech H. medicinalis (Zipser et al 1998) and in echinoderms (Smith and Goad 1971;Shubina et al 1998). In insects, such molecules can occur together with true ecdysteroids-see for instance the bombycosterol produced by Bombyx ovaries (Fujimoto et al 1985).…”

Section: Protoecdysteroids?mentioning

confidence: 97%

“…These steroids are often considered as defense compounds against potential predators or pathogens. These cytotoxic properties give them a great interest in pharmacology, e.g., as antitumor molecules, and this research area is very active: just see the huge and continuously increasing number of described steroids (e.g., Shubina et al 1998;Aiello et al 1999;Wright et al 2003). A function for the animal itself cannot be excluded: some of these steroids might for instance represent modulators of hormones (Ikegami 1976) or growth factors; thus, a new class of steroids (linckosides, isolated from the starfish Linckia laevigata) which can stimulate neurite outgrowth by acting synergistically with neural growth factor (Qi et al 2002(Qi et al , 2004.…”

Section: Protoecdysteroids?mentioning

confidence: 99%

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Steroids in aquatic invertebrates

2007

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Steroid molecules are present in all invertebrates, and some of them have established hormonal roles: this is the case for ecdysteroids in arthropods and, to a lesser extent, for vertebrate-type steroids in molluscs. Steroids are not only hormones, they may also fulfill many other functions in chemical communication, chemical defense or even digestive physiology. The increasing occurrence of endocrine disruption problems caused by environmental pollutants, which interfere in particular with reproductive physiology of vertebrates but also of invertebrates has made necessary to better understand the endocrine physiology of the latter and the role of steroids in these processes. So many attempts are being made to better understand the endocrine roles of steroids in arthropods and molluscs, and to establish whether they also fulfill similar functions in other invertebrate phyla. At the moment, both the precise identification of these steroids, the determination of their origin (endogenous versus exogenous) and of their mechanism of action are under active investigation. This research takes profit of the development of genome sequencing programs on many invertebrate species, which allow the identification of receptors and/or biosynthetic enzymes, when related to their vertebrate counterparts, but the story is not so simple, as will be exemplified by estrogen receptors of molluscs.

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Section: Protoecdysteroids?mentioning

confidence: 97%

Section: Protoecdysteroids?mentioning

confidence: 99%

Steroids in aquatic invertebrates

2007

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“…According to chemical structure, steroidal glycosides are subdivided into three main groups: asterosaponins, cyclic glycosides, and polyhydroxysteroidal glycosides. Polyhydroxysteroidal glycosides from starfish is one of the predominant glycosides with unique structural characteristics [2,3], which consist of a polyhydroxylated steroidal aglycone linked to one or two (rarely three) sugar units and occur in both sulfated and nonsulfated form [4,5,6]. Steroidal metabolites from starfish, especially steroidal oligoglycosides, were reported to show a broad spectrum of biological activities, including cytotoxic, hemolytic, antiviral, antibacterial, antibiofouling, neuritogenic, and antifungal effects [1,7,8,9,10].…”

Section: Introductionmentioning

confidence: 99%

Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus

Kang

Han

2016

Marine Drugs

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Three new polyhydroxysteroidal glycosides, hesperuside A (1), B (2), and C (3), as well as a known novaeguinoside A (4), were isolated from the ethanol extract of starfish Craspidaster hesperus collected from the South China Sea. Their structures were elucidated by extensive spectroscopic methods and chemical evidence. The compounds 1–3 present unprecedented carbohydrate chain 3-O-methyl-β-d-galactopyranose, which differ from each other in the side chains. These compounds exhibited cytotoxicity against human tumor cells BEL-7402, MOLT-4, and A-549 in vitro.

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“…The steroid 4 was obtained by acetylation of 5. Structures of 1-7 were elucidated by analysis of their 1 H, 13 C and 2D NMR spectra and by comparison with spectra and physical constants of standard compounds isolated earlier [9,[11][12][13][14].…”

mentioning

confidence: 99%

Steroid Sulfates from Ophiuroids (Brittle Stars): Action on Some Factors of Innate and Adaptive Immunity

Гажа

Ivanushko

Levina

et al. 2016

Natural Product Communications

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The action of seven polyhydroxylated sterol mono-and disulfates (1-7), isolated from ophiuroids, on innate and adaptive immunity was examined in in vitro and in vivo experiments. At least, three of them (1, 2 and 4) increased the functional activities of neutrophils, including levels of oxygen-dependent metabolism, adhesive and phagocytic properties, and induced the expression of pro-inflammatory cytokines TNF- and IL-8. Compound 4 was the most active for enhancing the production of antibody forming cells in the mouse spleen.

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Comparative study on polyhydroxylated steroids from echinoderms

Cited by 13 publications

References 15 publications

Steroids in aquatic invertebrates

Steroids in aquatic invertebrates

Three New Cytotoxic Polyhydroxysteroidal Glycosides from Starfish Craspidaster hesperus

Steroid Sulfates from Ophiuroids (Brittle Stars): Action on Some Factors of Innate and Adaptive Immunity

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