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Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (10 March 2021) | Viewed by 37852

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Dr. Pavel S. Dmitrenok

E-Mail Website
Guest Editor
G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far East Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia
Interests: marine natural products; mass spectrometry; chemical structures; metabolomics; proteomics
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Recently, the G.B. Elyakov Pacific Institute of Bioorganic Chemistry (PIBOC) celebrated its 55th anniversary. Over many years, we have been carrying out studies on the natural products of a both marine and terrestrial origin. In collaboration with many Russian and Foreign scientists, we have investigated diverse biomolecules, including steroids and terpenoids, quinoid compounds and alkaloids, polysaccharides and lipids, enzymes and lectins, proteins, and peptides. Many living creatures such as higher plants, algae, marine invertebrates, marine bacteria, and fungi have been examined as sources of biologically active compounds, and numerous new species have been described, predominantly marine microorganisms. The biological activities of natural compounds were also studied. Long-term research at PIBOC have covered the fields of bioorganic chemistry, biochemistry, molecular immunology, organic synthesis of natural compounds, marine microbiology, genetic engineering, botany, and biotechnology. The conference, dedicated to the 55th anniversary of the G.B. Elyakov Pacific Institute of Bioorganic Chemistry, was held in Vladivostok on 11–15 September 2019, with the participation of scientists from other Scientific Institutions and Universities of our country. In accordance with the decision and sponsor support of the International scientific journal of Molecules, a Special Issue of Molecules will be submitted. We invite all participants of this conference, as well as all collaborators and friends of our institute take a part in preparing this Issue.

We hope that new scientific articles about the isolation, structures, properties, and biogenesis of biomolecules; new methods and approaches to their study, which should be prepared on the basis of lectures presented at the conference; and the studies of the scientific teams collaborating with us will be of interest for readers of Molecules.

Dr. Pavel S. Dmitrenok
Guest Editor

Manuscript Submission Information

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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. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). 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

  • bioorganic chemistry
  • biochemistry
  • molecular immunology
  • organic synthesis
  • marine microbiology
  • genetic engineering
  • botany
  • biotechnology
  • natural products
  • biomolecules
  • higher plants
  • algae
  • marine invertebrates
  • marine bacteria
  • fungi
  • marine microorganisms
  • steroids
  • terpenoids
  • quinoid compounds
  • alkaloids
  • polysaccharides
  • lipids

Published Papers (15 papers)

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Editorial

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3 pages, 182 KiB  
Editorial
Editorial to the Special Issue: “Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences”
by Pavel S. Dmitrenok
Molecules 2021, 26(16), 4971; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26164971 - 17 Aug 2021
Cited by 1 | Viewed by 1361
Abstract
The G [...] Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)

Research

Jump to: Editorial, Review, Other

14 pages, 2239 KiB  
Article
Differential Expression of Yersinia pseudotuberculosis General Porin Genes during Short- and Long-Term Antibiotic Stresses
by Evgeniya Bystritskaya, Nadezhda Chernysheva, Anna Stenkova, Konstantin Guzev, Alexander Rakin and Marina Isaeva
Molecules 2021, 26(13), 3956; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133956 - 28 Jun 2021
Cited by 4 | Viewed by 1950
Abstract
Here, we investigated general porin regulation in Yersinia pseudotuberculosis 488, the causative agent of Far Eastern scarlet-like fever, in response to sublethal concentrations of antibiotics. We chose four antibiotics of different classes and measured gene expression using qRT-PCR and GFP reporter systems. Our [...] Read more.
Here, we investigated general porin regulation in Yersinia pseudotuberculosis 488, the causative agent of Far Eastern scarlet-like fever, in response to sublethal concentrations of antibiotics. We chose four antibiotics of different classes and measured gene expression using qRT-PCR and GFP reporter systems. Our data showed temporal regulation of the general porin genes ompF and ompC caused by antibiotic stress. The porin transcription initially decreased, providing early defensive response of the bacterium, while it returned to that of the untreated cells on prolonged antibiotic exposure. Unlike the major porin genes, the transcription of the alternative porin genes ompX and lamB was increased. Moreover, a short-term ompR- and marA-mediated porin regulation was observed. The main finding was a phenotypic heterogeneity of Y. pseudotuberculosis population manifested in variable porin gene expression under carbenicillin exposure. This may offer adaptive fitness advantages for a particular bacterial subpopulation. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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22 pages, 4308 KiB  
Article
Studies on the Structure and Properties of Membrane Phospholipase A1 Inclusion Bodies Formed at Low Growth Temperatures Using GFP Fusion Strategy
by Svetlana I. Bakholdina, Anna M. Stenkova, Evgenia P. Bystritskaya, Evgeniy V. Sidorin, Natalya Yu. Kim, Ekaterina S. Menchinskaya, Tatiana Yu. Gorpenchenko, Dmitry L. Aminin, Nikita A. Shved and Tamara F. Solov’eva
Molecules 2021, 26(13), 3936; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26133936 - 28 Jun 2021
Cited by 10 | Viewed by 3007
Abstract
The effect of cultivation temperatures (37, 26, and 18 °C) on the conformational quality of Yersinia pseudotuberculosis phospholipase A1 (PldA) in inclusion bodies (IBs) was studied using green fluorescent protein (GFP) as a folding reporter. GFP was fused to the C-terminus of [...] Read more.
The effect of cultivation temperatures (37, 26, and 18 °C) on the conformational quality of Yersinia pseudotuberculosis phospholipase A1 (PldA) in inclusion bodies (IBs) was studied using green fluorescent protein (GFP) as a folding reporter. GFP was fused to the C-terminus of PldA to form the PldA-GFP chimeric protein. It was found that the maximum level of fluorescence and expression of the chimeric protein is observed in cells grown at 18 °C, while at 37 °C no formation of fluorescently active forms of PldA-GFP occurs. The size, stability in denaturant solutions, and enzymatic and biological activity of PldA-GFP IBs expressed at 18 °C, as well as the secondary structure and arrangement of protein molecules inside the IBs, were studied. Solubilization of the chimeric protein from IBs in urea and SDS is accompanied by its denaturation. The obtained data show the structural heterogeneity of PldA-GFP IBs. It can be assumed that compactly packed, properly folded, proteolytic resistant, and structurally less organized, susceptible to proteolysis polypeptides can coexist in PldA-GFP IBs. The use of GFP as a fusion partner improves the conformational quality of PldA, but negatively affects its enzymatic activity. The PldA-GFP IBs are not toxic to eukaryotic cells and have the property to penetrate neuroblastoma cells. Data presented in the work show that the GFP-marker can be useful not only as target protein folding indicator, but also as a tool for studying the molecular organization of IBs, their morphology, and localization in E. coli, as well as for visualization of IBs interactions with eukaryotic cells. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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12 pages, 5020 KiB  
Article
Genome-Wide Analysis of PL7 Alginate Lyases in the Genus Zobellia
by Nadezhda Chernysheva, Evgeniya Bystritskaya, Galina Likhatskaya, Olga Nedashkovskaya and Marina Isaeva
Molecules 2021, 26(8), 2387; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26082387 - 20 Apr 2021
Cited by 7 | Viewed by 2271
Abstract
We carried out a detailed investigation of PL7 alginate lyases across the Zobellia genus. The main findings were obtained using the methods of comparative genomics and spatial structure modeling, as well as a phylogenomic approach. Initially, in order to elucidate the alginolytic potential [...] Read more.
We carried out a detailed investigation of PL7 alginate lyases across the Zobellia genus. The main findings were obtained using the methods of comparative genomics and spatial structure modeling, as well as a phylogenomic approach. Initially, in order to elucidate the alginolytic potential of Zobellia, we calculated the content of polysaccharide lyase (PL) genes in each genome. The genus-specific PLs were PL1, PL6, PL7 (the most abundant), PL14, PL17, and PL40. We revealed that PL7 belongs to subfamilies 3, 5, and 6. They may be involved in local and horizontal gene transfer and gene duplication processes. Most likely, an individual evolution of PL7 genes promotes the genetic variability of the Alginate Utilization System across Zobellia. Apparently, the PL7 alginate lyases may acquire a sub-functionalization due to diversification between in-paralogs. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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12 pages, 1581 KiB  
Article
Human Lanosterol 14-Alpha Demethylase (CYP51A1) Is a Putative Target for Natural Flavonoid Luteolin 7,3′-Disulfate
by Leonid Kaluzhskiy, Pavel Ershov, Evgeniy Yablokov, Tatsiana Shkel, Irina Grabovec, Yuri Mezentsev, Oksana Gnedenko, Sergey Usanov, Polina Shabunya, Sviatlana Fatykhava, Alexander Popov, Aleksandr Artyukov, Olga Styshova, Andrei Gilep, Natallia Strushkevich and Alexis Ivanov
Molecules 2021, 26(8), 2237; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26082237 - 13 Apr 2021
Cited by 11 | Viewed by 3707
Abstract
Widespread pathologies such as atherosclerosis, metabolic syndrome and cancer are associated with dysregulation of sterol biosynthesis and metabolism. Cholesterol modulates the signaling pathways of neoplastic transformation and tumor progression. Lanosterol 14-alpha demethylase (cytochrome P450(51), CYP51A1) catalyzes one of the key steps in cholesterol [...] Read more.
Widespread pathologies such as atherosclerosis, metabolic syndrome and cancer are associated with dysregulation of sterol biosynthesis and metabolism. Cholesterol modulates the signaling pathways of neoplastic transformation and tumor progression. Lanosterol 14-alpha demethylase (cytochrome P450(51), CYP51A1) catalyzes one of the key steps in cholesterol biosynthesis. The fairly low somatic mutation frequency of CYP51A1, its druggability, as well as the possibility of interfering with cholesterol metabolism in cancer cells collectively suggest the clinical importance of CYP51A1. Here, we show that the natural flavonoid, luteolin 7,3′-disulfate, inhibits CYP51A1 activity. We also screened baicalein and luteolin, known to have antitumor activities and low toxicity, for their ability to interact with CYP51A1. The Kd values were estimated using both a surface plasmon resonance optical biosensor and spectral titration assays. Unexpectedly, in the enzymatic activity assays, only the water-soluble form of luteolin—luteolin 7,3′-disulfate—showed the ability to potently inhibit CYP51A1. Based on molecular docking, luteolin 7,3′-disulfate binding suggests blocking of the substrate access channel. However, an alternative site on the proximal surface where the redox partner binds cannot be excluded. Overall, flavonoids have the potential to inhibit the activity of human CYP51A1 and should be further explored for their cholesterol-lowering and anti-cancer activity. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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13 pages, 2784 KiB  
Article
New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge
by Sophia A. Kolesnikova, Ekaterina G. Lyakhova, Anastasia B. Kozhushnaya, Anatoly I. Kalinovsky, Dmitrii V. Berdyshev, Roman S. Popov and Valentin A. Stonik
Molecules 2021, 26(3), 678; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26030678 - 28 Jan 2021
Cited by 6 | Viewed by 2193
Abstract
In continuation of our studies on a Vietnamese collection of a Stelletta sp., sponge we have isolated two new isomalabaricane triterpenoids, stellettins Q and R (1 and 2), and four new isomalabaricane-derived nor-terpenoids, stellettins S-V 3–6, along [...] Read more.
In continuation of our studies on a Vietnamese collection of a Stelletta sp., sponge we have isolated two new isomalabaricane triterpenoids, stellettins Q and R (1 and 2), and four new isomalabaricane-derived nor-terpenoids, stellettins S-V 3–6, along with previously known globostelletin N. Among them, compound 3 contains an acetylenic fragment, unprecedented in the isomalabaricane family and extremely rare in other marine sponge terpenoids. The structures and absolute configurations of all new compounds were established by extensive NMR, MS, and ECD analyses together with quantum-chemical modeling. Additionally, according to obtained new data we report the correction in stereochemistry of two asymmetric centers in the structures of two known isomalabaricanes, 15R,23S for globostelletin M and 15S,23R for globostelletin N. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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26 pages, 5422 KiB  
Article
Structural Analysis of Oxidized Cerebrosides from the Extract of Deep-Sea Sponge Aulosaccus sp.: Occurrence of Amide-Linked Allylically Oxygenated Fatty Acids
by Elena A. Santalova, Vladimir A. Denisenko and Pavel S. Dmitrenok
Molecules 2020, 25(24), 6047; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25246047 - 21 Dec 2020
Cited by 4 | Viewed by 2245
Abstract
The structural elucidation of primary and secondary peroxidation products, formed from complex lipids, is a challenge in lipid analysis. In the present study, rare minor oxidized cerebrosides, isolated from the extract of a far eastern deep-sea glass sponge, Aulosaccus sp., were analyzed as [...] Read more.
The structural elucidation of primary and secondary peroxidation products, formed from complex lipids, is a challenge in lipid analysis. In the present study, rare minor oxidized cerebrosides, isolated from the extract of a far eastern deep-sea glass sponge, Aulosaccus sp., were analyzed as constituents of a multi-component RP-HPLC (high-performance liquid chromatography on reversed-phase column) fraction using NMR (nuclear magnetic resonance) spectroscopy, mass spectrometry, GC (gas chromatography), and chemical transformations (including hydrogenation or derivatization with dimethyl disulfide before hydrolysis). Eighteen previously unknown β-D-glucopyranosyl-(1→1)-ceramides (1a–a//, 1b–b//, 2a–a//, 2b–b//, 3c–c//, 3d–d//) were shown to contain phytosphingosine-type backbones (2S,3S,4R,11Z)-2-aminoeicos-11-ene-1,3,4-triol (in 1), (2S,3S,4R,13Z)-2-aminoeicos-13-ene-1,3,4-triol (in 2), and (13S*,14R*)-2-amino-13,14-methylene-eicosane-1,3,4-triol (in 3). These backbones were N-acylated with straight-chain monoenoic (2R)-2-hydroxy acids that had allylic hydroperoxy/hydroxy/keto groups on C-17/ in the 15/E-23:1 chain (a–a//), C-16/ in the 17/E-23:1 (b–b//) and 14/E-22:1 (c–c//) chains, and C-15/ in the 16/E-22:1 chain (d–d//). Utilizing complementary instrumental and chemical methods allowed for the first detailed structural analysis of a complex mixture of glycosphingolipids, containing allylically oxygenated monoenoic acyl chains. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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13 pages, 2484 KiB  
Article
Sea Anemone Heteractis crispa Actinoporin Demonstrates In Vitro Anticancer Activities and Prevents HT-29 Colorectal Cancer Cell Migration
by Aleksandra Kvetkina, Olesya Malyarenko, Aleksandra Pavlenko, Sergey Dyshlovoy, Gunhild von Amsberg, Svetlana Ermakova and Elena Leychenko
Molecules 2020, 25(24), 5979; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25245979 - 17 Dec 2020
Cited by 8 | Viewed by 2183
Abstract
Actinoporins are the most abundant group of sea anemone cytolytic toxins. Their membranolytic activity is of high interest for the development of novel anticancer drugs. However, to date the activity of actinoporins in malignant cells has been poorly studied. Here, we report on [...] Read more.
Actinoporins are the most abundant group of sea anemone cytolytic toxins. Their membranolytic activity is of high interest for the development of novel anticancer drugs. However, to date the activity of actinoporins in malignant cells has been poorly studied. Here, we report on recombinant analog of Hct-S3 (rHct-S3), belonging to the combinatory library of Heteractis crispa actinoporins. rHct-S3 exhibited cytotoxic activity against breast MDA-MB-231 (IC50 = 7.3 µM), colorectal HT-29 (IC50 = 6.8 µM), and melanoma SK-MEL-28 (IC50 = 8.3 µM) cancer cells. The actinoporin effectively prevented epidermal growth factor -induced neoplastic transformation of JB6 Cl41 cells by 34% ± 0.2 and decreased colony formation of HT-29 cells by 47% ± 0.9, MDA-MB-231 cells by 37% ± 1.2, and SK-MEL-28 cells by 34% ± 3.6. Moreover, rHct-S3 decreased proliferation and suppressed migration of colorectal carcinoma cells by 31% ± 5.0 and 99% ± 6.4, respectively. The potent anti-migratory activity was proposed to mediate by decreased matrix metalloproteinases-2 and -9 expression. In addition, rHct-S3 induced programmed cell death by cleavage of caspase-3 and poly (ADP-ribose) polymerase, as well as regulation of Bax and Bcl-2. Our results indicate rHct-S3 to be a promising anticancer drug with a high anti-migratory potential. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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17 pages, 2588 KiB  
Article
Isolation and Structure Determination of Echinochrome A Oxidative Degradation Products
by Natalia P. Mishchenko, Elena A. Vasileva, Andrey V. Gerasimenko, Valeriya P. Grigorchuk, Pavel S. Dmitrenok and Sergey A. Fedoreyev
Molecules 2020, 25(20), 4778; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25204778 - 18 Oct 2020
Cited by 9 | Viewed by 2592
Abstract
Echinochrome A (Ech A, 1) is one of the main pigments of several sea urchin species and is registered in the Russian pharmacopeia as an active drug substance (Histochrome®), used in the fields of cardiology and ophthalmology. In this study, [...] Read more.
Echinochrome A (Ech A, 1) is one of the main pigments of several sea urchin species and is registered in the Russian pharmacopeia as an active drug substance (Histochrome®), used in the fields of cardiology and ophthalmology. In this study, Ech A degradation products formed during oxidation by O2 in air-equilibrated aqueous solutions were identified, isolated, and structurally characterized. An HPLC method coupled with diode-array detection (DAD) and mass spectrometry (MS) was developed and validated to monitor the Ech A degradation process and identify the appearing compounds. Five primary oxidation products were detected and their structures were proposed on the basis of high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) as 7-ethyl-2,2,3,3,5,7,8-heptahydroxy-2,3-dihydro-1,4-naphthoquinone (2), 6-ethyl-5,7,8-trihydroxy-1,2,3,4-tetrahydronaphthalene-1,2,3,4-tetraone (3), 2,3-epoxy-7-ethyl-2,3-dihydro-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone (4), 2,3,4,5,7-pentahydroxy-6-ethylinden-1-one (5), and 2,2,4,5,7-pentahydroxy-6-ethylindane-1,3-dione (6). Three novel oxidation products were isolated, and NMR and HR-ESI-MS methods were used to establish their structures as 4-ethyl-3,5,6-trihydroxy-2-oxalobenzoic acid (7), 4-ethyl-2-formyl-3,5,6-trihydroxybenzoic acid (8), and 4-ethyl-2,3,5-trihydroxybenzoic acid (9). The known compound 3-ethyl-2,5-dihydroxy-1,4-benzoquinone (10) was isolated along with products 7–9. Compound 7 turned out to be unstable; its anhydro derivative 11 was obtained in two crystal forms, the structure of which was elucidated using X-ray crystallography as 7-ethyl-5,6-dihydroxy-2,3-dioxo-2,3-dihydrobenzofuran-4-carboxylic acid and named echinolactone. The chemical mechanism of Ech A oxidative degradation is proposed. The in silico toxicity of Ech A and its degradation products 2 and 7–10 were predicted using the ProTox-II webserver. The predicted median lethal dose (LD50) value for product 2 was 221 mg/kg, and, for products 7–10, it appeared to be much lower (≥2000 mg/kg). For Ech A, the predicted toxicity and mutagenicity differed from our experimental data. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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19 pages, 1269 KiB  
Article
Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones
by Yuri E. Sabutski, Ekaterina S. Menchinskaya, Ludmila S. Shevchenko, Ekaterina A. Chingizova, Artur R. Chingizov, Roman S. Popov, Vladimir A. Denisenko, Valery V. Mikhailov, Dmitry L. Aminin and Sergey G. Polonik
Molecules 2020, 25(16), 3577; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25163577 - 06 Aug 2020
Cited by 8 | Viewed by 2422
Abstract
A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-O-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic [...] Read more.
A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-O-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC50 values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (Staphylococcus aureus, Bacillus cereus), Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), and fungus Candida albicans by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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7 pages, 1126 KiB  
Communication
In Vitro Anticancer and Radiosensitizing Activities of Phlorethols from the Brown Alga Costaria costata
by Olesya S. Malyarenko, Tatiana I. Imbs and Svetlana P. Ermakova
Molecules 2020, 25(14), 3208; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25143208 - 14 Jul 2020
Cited by 5 | Viewed by 1908
Abstract
The anticancer and radiosensitizing effects of high-molecular-weight phlorethols CcPh (Mw = 2520 Da) isolated from the brown algae of Costaria costata on human colorectal carcinoma HCT 116 and HT-29 cells were investigated. Phlorethols CcPh possessed cytotoxic activity against HT-29 (IC50 = 92 [...] Read more.
The anticancer and radiosensitizing effects of high-molecular-weight phlorethols CcPh (Mw = 2520 Da) isolated from the brown algae of Costaria costata on human colorectal carcinoma HCT 116 and HT-29 cells were investigated. Phlorethols CcPh possessed cytotoxic activity against HT-29 (IC50 = 92 μg/mL) and HCT 116 (IC50 = 94 μg/mL) cells. CcPh at non-toxic concentrations inhibited the colony formation in colon cancer cells and significantly enhanced their sensitivity to low non-toxic X-ray irradiation. The combinatory effect of radiation and CcPh was synergistic (Combination index < 0.7). Algal phlorethols might be prospective candidates as radiosensitizers to improve the scheme of radiotherapy. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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21 pages, 1214 KiB  
Article
Porin from Marine Bacterium Marinomonas primoryensis KMM 3633T: Isolation, Physico-Chemical Properties, and Functional Activity
by Olga D. Novikova, Valentina A. Khomenko, Natalia Yu. Kim, Galina N. Likhatskaya, Lyudmila A. Romanenko, Ekaterina I. Aksenova, Marina S. Kunda, Natalia N. Ryzhova, Olga Yu. Portnyagina, Tamara F. Solov’eva and Olga L. Voronina
Molecules 2020, 25(14), 3131; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25143131 - 08 Jul 2020
Cited by 6 | Viewed by 2524
Abstract
Marinomonas primoryensis KMM 3633T, extreme living marine bacterium was isolated from a sample of coastal sea ice in the Amursky Bay near Vladivostok, Russia. The goal of our investigation is to study outer membrane channels determining cell permeability. Porin from M. [...] Read more.
Marinomonas primoryensis KMM 3633T, extreme living marine bacterium was isolated from a sample of coastal sea ice in the Amursky Bay near Vladivostok, Russia. The goal of our investigation is to study outer membrane channels determining cell permeability. Porin from M. primoryensis KMM 3633T (MpOmp) has been isolated and characterized. Amino acid analysis and whole genome sequencing were the sources of amino acid data of porin, identified as Porin_4 according to the conservative domain searching. The amino acid composition of MpOmp distinguished by high content of acidic amino acids and low content of sulfur-containing amino acids, but there are no tryptophan residues in its molecule. The native MpOmp existed as a trimer. The reconstitution of MpOmp into black lipid membranes demonstrated its ability to form ion channels whose conductivity depends on the electrolyte concentration. The spatial structure of MpOmp had features typical for the classical gram-negative porins. However, the oligomeric structure of isolated MpOmp was distinguished by very low stability: heat-modified monomer was already observed at 30 °C. The data obtained suggest the stabilizing role of lipids in the natural membrane of marine bacteria in the formation of the oligomeric structure of porin. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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12 pages, 1779 KiB  
Article
Unusual Polyhydroxylated Steroids from the Starfish Anthenoides laevigatus, Collected off the Coastal Waters of Vietnam
by Alla A. Kicha, Dinh T. Ha, Timofey V. Malyarenko, Anatoly I. Kalinovsky, Roman S. Popov, Olesya S. Malyarenko, Tran T. T. Thuy, Pham Q. Long, Nguyen T. T. Ha and Natalia V. Ivanchina
Molecules 2020, 25(6), 1440; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25061440 - 23 Mar 2020
Cited by 3 | Viewed by 2791
Abstract
Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by [...] Read more.
Four new polyhydroxylated steroids 1–4 were isolated along with two previously known related steroids 5 and 6 from the methanolic extract of the starfish Anthenoides laevigatus collected off the coastal waters of Vietnam. Structures of new compounds were substantially elucidated by one-dimensional (1D) and two-dimensional (2D) NMR spectroscopy and HRESIMS techniques. Heptaol 1 and hexaol 2 contain the common 5α-cholestane skeleton, while hexaol 3 and heptaol 4 have the rare among starfish steroid compounds 5β-cholestane skeleton. Compounds 1, 5, and 6 do not show cytotoxic effects against normal JB6 Cl41 and cancer HT-29 and MDA-MB-231 cells, however they inhibit cell proliferation and colony formation of cancer HT-29 and MDA-MB-231 cells. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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Review

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20 pages, 5011 KiB  
Review
Marine Excitatory Amino Acids: Structure, Properties, Biosynthesis and Recent Approaches to Their Syntheses
by Valentin A. Stonik and Inna V. Stonik
Molecules 2020, 25(13), 3049; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25133049 - 03 Jul 2020
Cited by 5 | Viewed by 3454
Abstract
This review considers the results of recent studies on marine excitatory amino acids, including kainic acid, domoic acid, dysiherbaine, and neodysiherbaine A, known as potent agonists of one of subtypes of glutamate receptors, the so-called kainate receptors. Novel information, particularly concerning biosynthesis, environmental [...] Read more.
This review considers the results of recent studies on marine excitatory amino acids, including kainic acid, domoic acid, dysiherbaine, and neodysiherbaine A, known as potent agonists of one of subtypes of glutamate receptors, the so-called kainate receptors. Novel information, particularly concerning biosynthesis, environmental roles, biological action, and syntheses of these marine metabolites, obtained mainly in last 10–15 years, is summarized. The goal of the review was not only to discuss recently obtained data, but also to provide a brief introduction to the field of marine excitatory amino acid research. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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Other

10 pages, 826 KiB  
Brief Report
Are the Closely Related Cobetia Strains of Different Species?
by Yulia Noskova, Aleksandra Seitkalieva, Olga Nedashkovskaya, Liudmila Shevchenko, Liudmila Tekutyeva, Oksana Son and Larissa Balabanova
Molecules 2021, 26(3), 690; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26030690 - 28 Jan 2021
Cited by 6 | Viewed by 2074
Abstract
Marine bacteria of the genus Cobetia, which are promising sources of unique enzymes and secondary metabolites, were found to be complicatedly identified both by phenotypic indicators due to their ecophysiology diversity and 16S rRNA sequences because of their high homology. Therefore, searching for [...] Read more.
Marine bacteria of the genus Cobetia, which are promising sources of unique enzymes and secondary metabolites, were found to be complicatedly identified both by phenotypic indicators due to their ecophysiology diversity and 16S rRNA sequences because of their high homology. Therefore, searching for the additional methods for the species identification of Cobetia isolates is significant. The species-specific coding sequences for the enzymes of each functional category and different structural families were applied as additional molecular markers. The 13 closely related Cobetia isolates, collected in the Pacific Ocean from various habitats, were differentiated by the species-specific PCR patterns. An alkaline phosphatase PhoA seems to be a highly specific marker for C. amphilecti. However, the issue of C. amphilecti and C. litoralis, as well as C. marina and C. pacifica, belonging to the same or different species remains open. Full article
(This article belongs to the Special Issue Dedicated to the 55th Anniversary of G.B. Elyakov Pacific Institute of Bioorganic Chemistry of the Far Eastern Branch of the Russian Academy of Sciences)
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