Pyridine Nucleosides Neopetrosides A and B from a Marine <i>Neopetrosia</i> sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

Shubina, Larisa K.; Makarieva, Tatyana N.; Yashunsky, Dmitry V.; Nifantiev, Nikolay E.; Денисенко, В. А.; Dmitrenok, Pavel S.; Dyshlovoy, Sergey A.; Fedorov, Sergey N.; Krasokhin, Vladimir B.; Jeong, Sang Hoon; Han, Jin; Stonik, Valentin A.

doi:10.1021/acs.jnatprod.5b00256

Cited by 27 publications

(23 citation statements)

References 37 publications

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“…also yielded two nucleosides 913 and 914, one of which was also synthesised. 624 628 A Biemna sp. was the source of two pyridoacridines N-hydroxymethylisocystodamine 924 and neolabuanine 925.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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“…For instance, a sample of a new sponge species of the genus Neopetrosia was collected in Van Phong Bay, and two new naturally occurring pyridine nucleosides were isolated. [71] The strong dependence of the metabolism of invertebrate animals and microfilamentous fungi from the live conditions is a well-known fact. [75,76] The study of samples collected in the new locations often leads to the isolation of new bioactive compounds.…”

Section: Discussionmentioning

confidence: 99%

“…These were the first representatives of a new class of pyridine α-ribosides of nicotinic acid (Figure 12) containing extremely rare N-glycosidic bonds and the residues of p-hydroxybenzoic and pyrrole-2-carboxylic acids. [71] Neopetroside A (242) did not show any toxic effect toward mouse C2B12 myoblasts at concentrations up to 100 μM and increased the mitochondrial function (cell oxygen consumption and mitochondrial ATP level) of myoblasts at a concentration of 10 μM.…”

Section: Spongesmentioning

confidence: 94%

Achievements in the Study of Marine Low‐Molecular Weight Biologically Active Metabolites from the Vietnamese Territorial Waters as a Result of Expeditions aboard the Research Vessel ‘Akademik Oparin’ (2004–2017)

Yurchenko

Minh

et al. 2019

Chemistry & Biodiversity

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Until 2004, the secondary metabolites of marine organisms of the Vietnamese territorial waters had been studied very poorly. Only four new compounds were isolated from 1977 to 2003. Joint Russian‐Vietnamese expeditions aboard the research vessel ‘Akademik Oparin’ made it possible to study in detail the chemical diversity of marine micro‐ and macroorganisms. As a result of five expeditions, more than 250 low‐molecular weight natural compounds, including 117 new metabolites, were isolated from marine invertebrates and microfilamentous fungi. Their biological activities, such as cytotoxic, cytoprotective, and antioxidant activities, were investigated. Information about the structure and biological activity of the compounds, the source for their isolation and the geographical location of the objects is summarized in this review.

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“…All these characteristics have attracted attention to this species. In the course of our ongoing research on bioactive secondary metabolites from marine invertebrates [19,20], a new guanidine alkaloid was isolated from C. variopedatus. Here we report the complete structural characterization of the isolated compound, including assignment of absolute configuration and distribution of 1 and 2 in different body parts.…”

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confidence: 99%

Absolute Configuration and Body Part Distribution of the Alkaloid 6-epi-Monanchorin from the Marine Polychaete Chaetopterus variopedatus

Shubina

Makarieva

Denisenko

et al. 2016

Natural Product Communications

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As a result of the first study on secondary metabolites from the cosmopolitan bioluminescent marine tube polychaete Chaetopterus variopedatus, a new bicyclic guanidine alkaloid, 6-epi-monanchorin (1), along with the previously known monanchorin (2) were isolated. The structure of 1 was elucidated by spectroscopic and chemical methods, including a cleavage of the C 1-O 7 bond to obtain a secondary alcohol (3), which was used to determine the absolute configurations by Mosher's method. It was found that 1 and 2 were mainly accumulated in a secreted mucus special organ of the worm (food net), where green and blue-green microalgae were detected. A biosynthetic pathway to 6-epi-monanchorin and monanchorin from dietary polyenic fatty acid precursors was proposed.

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Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue

Cited by 27 publications

References 37 publications

Marine natural products

Marine natural products

Achievements in the Study of Marine Low‐Molecular Weight Biologically Active Metabolites from the Vietnamese Territorial Waters as a Result of Expeditions aboard the Research Vessel ‘Akademik Oparin’ (2004–2017)

Absolute Configuration and Body Part Distribution of the Alkaloid 6-epi-Monanchorin from the Marine Polychaete Chaetopterus variopedatus

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