New Ophiuroid-Type Steroids from the Starfish <i>Pteraster </i><i>tesselatus</i>

Levina, E. V.; Andriyaschenko, P.V.; Kalinovsky, and Anatoly I.; Stonik, Valentin A.

doi:10.1021/np9801864

Cited by 21 publications

(23 citation statements)

References 15 publications

(40 reference statements)

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“…A study of the starfish Diplopteraster multipes afforded a series of sterol sulfates including compound 4 [4]. The starfish Pteraster tesselatus contained three similar sterol disulfates 5 -7, an observation that has interesting chemotaxonomic implications [5]. Several hemolytic steroid disulfates, including 8 and 9, were reported from the starfish Pteraster pulvillus collected in the Sea of Okhotsk, Far East [6].…”

Section: Review Chemical Constituents and Bioactivities Of Starfishmentioning

confidence: 99%

Chemical Constituents and Bioactivities of Starfish

Dong

Tian

Yang

et al. 2011

Chemistry & Biodiversity

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Starfish have been the research topic in many chemical and pharmacological laboratories due to their complex secondary metabolites and diverse bioactivities. The aim of this review is to provide an up-to-date review on the chemistry and bioactivity of compounds isolated from all kinds of starfish to illustrate the chemodiversity and biological significance of these constituents, along with their geographical distribution where it is discernible.

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Section: Review Chemical Constituents and Bioactivities Of Starfishmentioning

confidence: 99%

Chemical Constituents and Bioactivities of Starfish

Dong

Tian

Yang

et al. 2011

Chemistry & Biodiversity

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“…In addition, there are numerous highly ac tive polar steroids with 24(28) methylene side chain, in particular, brassinolide dolichosterones and doli cholides from higher plants, some asterosaponins and poly hydroxysteroids from starfishes, 10 and steroid disulfates of brittle stars. 11 Mechanisms of their biosyntheses can be established by using labeled sterol as the biosyn thetic precursors. …”

Section: Resultsmentioning

confidence: 99%

Preparation of 13C-24-methylcholesta-5,24(28)-dien-3β-ol by cultivation of the Baikal diatom Synedra acus in NaH13CO3

et al. 2010

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A method for preparing 13 C 24 methylcholesta 5,24(28) dien 3β ol (24 methylenecho lesterol) with 13 C enrichment degree of up to 55% was proposed. The method is based on cultivation of the freshwater diatom alga Synedra acus in a medium containing sodium 13 C bicarbonate as the carbon source. 13 C 24 Methylenecholesterol isolated for the first time was studied by 13 C NMR spectroscopy and mass spectrometry.Key words: diatom microalga Synedra acus, sodium 13 C bicarbonate, steroids, 13 C 24 me thylcholesta 5,24(28) dien 3β ol, 13 C NMR spectroscopy, mass spectrometry.Biomolecules labeled by stable isotopes find extensive use in biomedical studies. Chemical and enzymatic meth ods for their preparation are complicated and expensive. An alternative approach is cultivation of microorganisms in the media containing labeled precursors followed by isolation of the target biosynthesis products. The cost of labeled compounds obtained by the biotechnological tech nique is usually lower than the cost of the products of organic synthesis. 1Diatom algae are of considerable practical interest for the biotechnology of organic compounds with a unique structure. This is due to the fact that the total structure of their genome has been decoded (the marine species Thalas siosira pseudonana and Pheodactylum tricprnutum) and more than 11000 genes were identified, 2 and also various methods for diatom cultivation in photobioreactors under controlled conditions were developed. 3,4 The diatom al gae produce a variety of steroids, which can be represented by 3-10 compounds in isolated sterol fractions. 5 How ever, 13 C cholesterol is the only sterol present in the market of 13 C labeled compounds. In this work we propose a method for preparing 13 C 24 methylenecholesterol based on cultivation of the freshwater diatom alga Synedra acus in a medium with sodium 13 C bicarbonate.Experimental 13 C NMR spectra were recorded on a Bruker DRX 500 spec trometer in CDCl 3 with internal SiMe 4 . Column chromatogra phy was carried out on silica gel (50-160 μm, Sorbpolymer, Russia). TLC was carried out on Sorbfil plates (Sorbpolymer, Russia), the spots were visualized by a H 2 SO 4 -EtOH mixture (1 : 4, v/v) followed by heating. GLC/MS analysis was performed on a HP6890 HP5973 GC MS System chromatograph (Hewlett Packard) with an HP 5MS capillary column at 270 °C using He as the carrier gas and an ionizing voltage of 70 eV. EI mass spectrum of a 13 C 24 methylcholesta 5,24(28) dien 3β ol ace tate sample with maximum 13 C inclusion was recorded on an AMD 604S double focusing magnetic sector mass spectrometer (AMD Intectra, Germany), electron energy 70 eV, accelerating voltage 8 kV. The 13 C isotope enrichment factor (IEF) was de termined by mass spectrometry and calculated from the follow ing equation: 6 , where M, M + 1 and so on are the numerical m/z values for molecular peaks of different isotopomers; I M , I M+1 and so on are the integral intensities of the signals corresponding to the ions of these masses, n is the number of C atoms in the molecule...

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“…The disulfated steroid ( 60 ) containing three functional groups in the ring A was isolated from the Antarctic brittle star Ophiosparte gigas [ 17 ], and the same steroid also was found in Astroclades exiguus and Amphiophiura ponderosa [ 94 ]. Rare sulfated steroid ( 62 ), containing sulfate groups in 2β- and 21α-positions, was detected in extracts from the starfish of the starfish Pteraster tesselatus [ 95 ].…”

Section: Di- and Poly-sulfated Steroids Derived From Marine Sourcesmentioning

confidence: 99%

Sulfated and Sulfur-Containing Steroids and Their Pharmacological Profile

et al. 2021

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The review focuses on sulfated steroids that have been isolated from seaweeds, marine sponges, soft corals, ascidians, starfish, and other marine invertebrates. Sulfur-containing steroids and triterpenoids are sourced from sedentary marine coelenterates, plants, marine sediments, crude oil, and other geological deposits. The review presents the pharmacological profile of sulfated steroids, sulfur-containing steroids, and triterpenoids, which is based on data obtained using the PASS program. In addition, several semi-synthetic and synthetic epithio steroids, which represent a rare group of bioactive lipids that have not yet been found in nature, but possess a high level of antitumor activity, were included in this review for the comparative pharmacological characterization of this class of compounds. About 140 steroids and triterpenoids are presented in this review, which demonstrate a wide range of biological activities. Therefore, out of 71 sulfated steroids, thirteen show strong antitumor activity with a confidence level of more than 90%, out of 50 sulfur-containing steroids, only four show strong antitumor activity with a confidence level of more than 93%, and out of eighteen epithio steroids, thirteen steroids show strong antitumor activity with a confidence level of 91% to 97.4%.

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New Ophiuroid-Type Steroids from the Starfish Pteraster tesselatus

Cited by 21 publications

References 15 publications

Chemical Constituents and Bioactivities of Starfish

Chemical Constituents and Bioactivities of Starfish

Preparation of 13C-24-methylcholesta-5,24(28)-dien-3β-ol by cultivation of the Baikal diatom Synedra acus in NaH13CO3

Sulfated and Sulfur-Containing Steroids and Their Pharmacological Profile

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