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The Structures and Biologic Activity of Marine Natural Products
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The Structures and Biologic Activity of Marine Natural Products

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: 15 May 2024 | Viewed by 4308

Special Issue Editors

Dr. Alexanra S. Silchenko

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Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Interests: natural products chemistry; sea cucumbers; triterpene glycosides; biological activities; chemotaxonomy; biosynthesis; NMR spectroscopy
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Vladimir Kalinin

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Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 690022 Vladivostok, Russia
Interests: marine natural products; triterpenoids, echinoderms; biologic activity; structure-activity relationships; biosynthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine natural products are physiologically and ecologically active compounds of diverse structural classes including biopolymers and low molecular weight substances. These metabolites originate from different biological sources such as invertebrates, algae, fungi and bacteria, inhabiting the marine environment. Changeable and hostile living conditions force marine organisms to adapt by driving chemical evolution. As result, plenty of new molecules with unique chemical structures and biological activities have arisen.

The discovery of some hundreds of thousands of new natural products from marine sources is explained by the considerable differences in the biochemistry of marine and terrestrial organisms, especially in secondary metabolism. The huge chemical and functional diversity are inherent to marine low molecular weight bioregulators (secondary metabolites) belonging to such classes as: isoprenoids, phenolic and quinoid compounds, polyketides, polyether’s, alkaloids and glycosides. The products of primary metabolism, including marine carbohydrates (fucoidans, chitosan’s etc.), proteins (enzymes and peptides with diverse functionality) and lipids (ceramides, cerebrosides, gangliosides) also differ from the compounds of terrestrial origin. Their uncommon structures cause various biological action that, in turn, triggered the investigations in the field of Research and Drug development resulting in the designing of naturally based medicines and therapeutics. Since the drug design should be based on the precise and comprehensive knowledge of chemical structures of the active ingredients, the development of the related scientific and applied fields including HPLC technologies for the separation of complex mixtures of natural products, NMR spectroscopy and mass-spectrometry resulted from this demand. Another fast-developing direction related to the natural products research is metabolomics that allows to obtain chemical “fingerprints” of different cell types, tissues, organs or the whole organism. Metabolomic approaches are successfully applied for analysis of distribution of tracking metabolites in different tissues and organs, investigation of the influence of different factors on their qualitative and quantitative content, for help to clearly understanding the physiologic and ecologic functions of natural products.

The modern approaches make possible thorough studying of marine natural products including the isolation of minor compounds expanding and deepening fundamental understanding of their biodiversity, functions and biosynthesis.

All the original research and reviews concerning structure elucidation, biologic activity and structure-activity relationships studying, metabolic profiling and biosynthetic peculiarities analysis of marine natural products are welcomed in this special issue.

Dr. Alexanra S. Silchenko
Prof. Dr. Vladimir Kalinin
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. There is an Article Processing Charge (APC) for publication in this open access journal. For details about the APC please see here. Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • marine natural products
  • secondary metabolites
  • structure elucidation
  • biologic activity
  • structure-activity relationships
  • taxonomic distribution
  • biosynthesis
  • functions

Published Papers (3 papers)

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Research

20 pages, 2823 KiB  
Article
Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi Penicillium sajarovii KMM 4718 and Aspergillus protuberus KMM 4747
by Elena V. Leshchenko, Dmitrii V. Berdyshev, Ekaterina A. Yurchenko, Alexandr S. Antonov, Gleb V. Borkunov, Natalya N. Kirichuk, Viktoria E. Chausova, Anatoly I. Kalinovskiy, Roman S. Popov, Yuliya V. Khudyakova, Ekaterina A. Chingizova, Artur R. Chingizov, Marina P. Isaeva and Anton N. Yurchenko
Int. J. Mol. Sci. 2023, 24(23), 16568; https://doi.org/10.3390/ijms242316568 - 21 Nov 2023
Viewed by 878
Abstract
The marine-derived fungal strains KMM 4718 and KMM 4747 isolated from sea urchin Scaphechinus mirabilis as a natural fungal complex were identified as Penicillium sajarovii and Aspergillus protuberus based on Internal Transcribed Spacer (ITS), partial β-tubulin (BenA), and calmodulin [...] Read more.
The marine-derived fungal strains KMM 4718 and KMM 4747 isolated from sea urchin Scaphechinus mirabilis as a natural fungal complex were identified as Penicillium sajarovii and Aspergillus protuberus based on Internal Transcribed Spacer (ITS), partial β-tubulin (BenA), and calmodulin (CaM) molecular markers as well as an ribosomal polymerase two, subunit two (RPB2) region for KMM 4747. From the ethyl acetate extract of the co-culture, two new polyketides, sajaroketides A (1) and B (2), together with (2′S)-7-hydroxy-2-(2′-hydroxypropyl)-5-methylchromone (3), altechromone A (4), norlichexanthone (5), griseoxanthone C (6), 1,3,5,6-tetrahydroxy-8-methylxanthone (7), griseofulvin (8), 6-O-desmethylgriseofulvin (9), dechlorogriseofulvin (10), and 5,6-dihydro-4-methyl-2H-pyran-2-one (11) were identified. The structures of the compounds were elucidated using spectroscopic analyses. The absolute configurations of the chiral centers of sajaroketides A and B were determined using time-dependent density functional theory (TDDFT)-based calculations of the Electronic Circular Dichroism (ECD) spectra. The inhibitory effects of these compounds on urease activity and the growth of Staphylococcus aureus, Escherichia coli, and Candida albicans were observed. Sajaroketide A, altechromone A, and griseofulvin showed significant cardioprotective effects in an in vitro model of S. aureus-induced infectious myocarditis. Full article
(This article belongs to the Special Issue The Structures and Biologic Activity of Marine Natural Products)
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24 pages, 2432 KiB  
Article
Djakonoviosides A, A1, A2, B1–B4 — Triterpene Monosulfated Tetra- and Pentaosides from the Sea Cucumber Cucumaria djakonovi: The First Finding of a Hemiketal Fragment in the Aglycones; Activity against Human Breast Cancer Cell Lines
by Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Roman S. Popov, Pavel S. Dmitrenok, Ekaterina A. Chingizova, Ekaterina S. Menchinskaya, Elena G. Panina, Vadim G. Stepanov, Vladimir I. Kalinin and Valentin A. Stonik
Int. J. Mol. Sci. 2023, 24(13), 11128; https://doi.org/10.3390/ijms241311128 - 05 Jul 2023
Cited by 2 | Viewed by 1021
Abstract
Seven new monosulfated triterpene glycosides, djakonoviosides A (1), A1 (2), A2 (3), and B1–B4 (4–7), along with three known glycosides found earlier in the other Cucumaria species, namely [...] Read more.
Seven new monosulfated triterpene glycosides, djakonoviosides A (1), A1 (2), A2 (3), and B1–B4 (4–7), along with three known glycosides found earlier in the other Cucumaria species, namely okhotoside A1-1, cucumarioside A0-1, and frondoside D, have been isolated from the far eastern sea cucumber Cucumaria djakonovi (Cucumariidae, Dendrochirotida). The structures were established on the basis of extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds of groups A and B differ from each other in their carbohydrate chains, namely monosulfated tetrasaccharide chains are inherent to group A and pentasaccharide chains with one sulfate group, branched by C-2 Qui2, are characteristic of group B. The aglycones of djakonoviosides A2 (3), B2 (5), and B4 (7) are characterized by a unique structural feature, a 23,16-hemiketal fragment found first in the sea cucumbers’ glycosides. The biosynthetic pathway of its formation is discussed. The set of aglycones of C. djakonovi glycosides was species specific because of the presence of new aglycones. At the same time, the finding in C. djakonovi of the known glycosides isolated earlier from the other species of Cucumaria, as well as the set of carbohydrate chains characteristic of the glycosides of all investigated representatives of the genus Cucumaria, demonstrated the significance of these glycosides as chemotaxonomic markers. The membranolytic actions of compounds 1–7 and known glycosides okhotoside A1-1, cucumarioside A0-1, and frondoside D, isolated from C. djakonovi against human cell lines, including erythrocytes and breast cancer cells (MCF-7, T-47D, and triple negative MDA-MB-231), as well as leukemia HL-60 and the embryonic kidney HEK-293 cell line, have been studied. Okhotoside A1-1 was the most active compound from the series because of the presence of a tetrasaccharide linear chain and holostane aglycone with a 7(8)-double bond and 16β-O-acetoxy group, cucumarioside A0-1, having the same aglycone, was slightly less active because of the presence of branching xylose residue at C-2 Qui2. Generally, the activity of the djakonoviosides of group A was higher than that of the djakonoviosides of group B containing the same aglycones, indicating the significance of a linear chain containing four monosaccharide residues for the demonstration of membranolytic action by the glycosides. All the compounds containing hemiketal fragments, djakonovioside A2 (3), B2 (5), and B4 (7), were almost inactive. The most aggressive triple-negative MDA-MB-231 breast cancer cell line was the most sensitive to the glycosides action when compared with the other cancer cells. Okhotoside A1-1 and cucumarioside A0-1 demonstrated promising effects against MDA-MB-231 cells, significantly inhibiting the migration, as well as the formation and growth, of colonies. Full article
(This article belongs to the Special Issue The Structures and Biologic Activity of Marine Natural Products)
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25 pages, 6103 KiB  
Article
Absolute Stereochemistry and Cytotoxic Effects of Vismione E from Marine Sponge-Derived Fungus Aspergillus sp. 1901NT-1.2.2
by Elena V. Girich, Phan Thi Hoai Trinh, Liliana E. Nesterenko, Roman S. Popov, Natalya Yu. Kim, Anton B. Rasin, Ekaterina S. Menchinskaya, Aleksandra S. Kuzmich, Ekaterina A. Chingizova, Artem S. Minin, Ngo Thi Duy Ngoc, Tran Thi Thanh Van, Ekaterina A. Yurchenko, Anton N. Yurchenko and Dmitry V. Berdyshev
Int. J. Mol. Sci. 2023, 24(9), 8150; https://doi.org/10.3390/ijms24098150 - 02 May 2023
Cited by 2 | Viewed by 1710
Abstract
The metabolic profile of the Aspergillus sp. 1901NT-1.2.2 sponge-associated fungal strain was investigated using the HPLC MS technique, and more than 23 peaks in the HPLC MS chromatogram were detected. Only two minor peaks were identified as endocrocin and terpene derivative MS data [...] Read more.
The metabolic profile of the Aspergillus sp. 1901NT-1.2.2 sponge-associated fungal strain was investigated using the HPLC MS technique, and more than 23 peaks in the HPLC MS chromatogram were detected. Only two minor peaks were identified as endocrocin and terpene derivative MS data from the GNPS database. The main compound was isolated and identified as known anthraquinone derivative vismione E. The absolute stereochemistry of vismione E was established for the first time using ECD and quantum chemical methods. Vismione E showed high cytotoxic activity against human breast cancer MCF-7 cells, with an IC50 of 9.0 µM, in comparison with low toxicity for normal human breast MCF-10A cells, with an IC50 of 65.3 µM. It was found that vismione E inhibits MCF-7 cell proliferation and arrests the cell cycle in the G1 phase. Moreover, the negative influence of vismione E on MCF-7 cell migration was detected. Molecular docking of vismione E suggested the IMPDH2 enzyme as one of the molecular targets for this anthraquinone derivative. Full article
(This article belongs to the Special Issue The Structures and Biologic Activity of Marine Natural Products)
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