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Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution...
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Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday

A special issue of Marine Drugs (ISSN 1660-3397).

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 31998

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

Special Issue Editors

Dr. Vladimir I. Kalinin

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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 product chemistry; secondary metabolites; sea cucumber triterpene glycosides; biological activities; evolution of biosynthesis; chemotaxonomy
Special Issues, Collections and Topics in MDPI journals
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
Dr. Natalia V. Ivanchina

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 product chemistry; secondary metabolites; starfish polar steroids and lipids; biological activities; metabolomics; biosynthesis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Intensive studies of marine natural products began in the 1960s. Marine metabolites show a great structural diversity, which indicates their unusual biosynthesis pathways. In addition, these compounds are fascinating to study as modulators of chemical–ecological interactions and possible active ingredients in medicinal and other useful preparations, such as taxonomic and food markers.

Professor, Dr.Sc. Valentin A. Stonik is one of the pioneers in this field, and began his impressive research career in marine natural products in the early 1970s, sometimes studying higher terrestrial plants and has continued his research activities ever since. He was born in Vladivostok, Russia on December 4, 1942 and graduated from the Department of Chemistry of the Far Eastern State University (Vladivostok) in 1965. Valentin A. Stonik received his PhD degree in Organic Chemistry in 1969 and Dr.Sc. degree in Bioorganic Chemistry: Chemistry of Natural and Physiologically Active Compounds in 1988. He became a Corresponding Member of the Russian Academy of Sciences in 1997 and a Full Member of the Russian Academy of Sciences (Academician) in 2003. He started his scientific activities from the synthesis of hydroacrydines and relative compounds. Since 1970, he has worked in the G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences. Prof. Stonik became Head of the Laboratory of Biosynthesis in 1976, Head of the Laboratory of Chemistry of Marine Natural Products in 1985, Deputy Director of the Institute from 1990 to 2002 and Director from 2002 to 2017. Since 2018, he has been the Scientific Advisor of the Institute.

His general interests in this research field are the structure and properties of biological active natural compounds from marine invertebrates, especially echinoderms and sponges, and his specific interests include the regulation of secondary metabolism, structural studies of alkaloids, unusual lipids, isoprenoids, polyhydroxysteroids, glycosides of polyhydroxysteroids, steroid and triterpenoid oligoglycosides, carbohydrates and other groups of natural products, as well as the investigation of the biological activities, biosynthesis, chemotaxonomy and chemical evolution of secondary metabolites. From the 1970s to 1990s he led numerous scientific expeditions on the research vessels “Kallisto”, “Professor Bogorov”, and “Akademic Oparin” in different regions of the Pacific and Indian Oceans. He is author and co-author of around 500 scientific articles in Russian and international journals, 3 monographs, 1 textbook and 20 patents. He is a member of the editorial boards of the journals: Marine Drugs, Natural Product Communications, Natural Product Letters, Russian Journal of Bioorganic Chemistry, and others.

On the occasion of Professor Valentin Stonik’s 80th birthday in December 2022, Dr. Vladimir I. Kalinin, Dr. Natalia V. Ivanchina, and Dr. Pavel S. Dmitrenok are editing a Themed Issue entitled “Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday”, in order to congratulate their scientific mentor.

Contributions to this Themed Issue may be submitted as original research or review articles and cover every aspect of marine natural products chemistry, from studying the chemical structures of new metabolites of marine macro- and microorganisms to the investigation of their biological activities, chemo-ecological issues, biosynthesis, genetic research, applications of spectral methods, including NMR spectroscopy and mass-spectrometry, and the synthesis of biological active natural products and their analogs.

This Themed Issue is intended as a gift to Professor Valentin A. Stonik from colleagues, friends, and world experts in marine natural products chemistry and other related disciplines that are thriving in the G.B. Elyakov Pacific Institute of Bioorganic Chemistry under his supervision.

Dr. Vladimir I. Kalinin
Dr. Pavel S. Dmitrenok
Dr. Natalia V. Ivanchina
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. Marine Drugs is an international peer-reviewed open access monthly 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 2900 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.

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Published Papers (13 papers)

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Editorial

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5 pages, 171 KiB  
Editorial
Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday
by Pavel S. Dmitrenok, Natalia V. Ivanchina and Vladimir I. Kalinin
Mar. Drugs 2024, 22(2), 56; https://doi.org/10.3390/md22020056 - 24 Jan 2024
Viewed by 1413
Abstract
Marine natural products are a very structurally diverse group of preferably low-weight organic molecules [...] Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)

Research

Jump to: Editorial, Review, Other

16 pages, 2384 KiB  
Article
Anticancer Activity of the Marine Triterpene Glycoside Cucumarioside A2-2 in Human Prostate Cancer Cells
by Ekaterina S. Menchinskaya, Sergey A. Dyshlovoy, Simone Venz, Christine Jacobsen, Jessica Hauschild, Tina Rohlfing, Aleksandra S. Silchenko, Sergey A. Avilov, Stefan Balabanov, Carsten Bokemeyer, Dmitry L. Aminin, Gunhild von Amsberg and Friedemann Honecker
Mar. Drugs 2024, 22(1), 20; https://doi.org/10.3390/md22010020 - 28 Dec 2023
Cited by 3 | Viewed by 2046
Abstract
Despite recent advances in the treatment of metastatic castration-resistant prostate cancer (CRPC), treatment is inevitably hampered by the development of drug resistance. Thus, new drugs are urgently needed. We investigated the efficacy, toxicity, and mechanism of action of the marine triterpene glycoside cucumarioside [...] Read more.
Despite recent advances in the treatment of metastatic castration-resistant prostate cancer (CRPC), treatment is inevitably hampered by the development of drug resistance. Thus, new drugs are urgently needed. We investigated the efficacy, toxicity, and mechanism of action of the marine triterpene glycoside cucumarioside A2-2 (CA2-2) using an in vitro CRPC model. CA2-2 induced a G2/M-phase cell cycle arrest in human prostate cancer PC-3 cells and caspase-dependent apoptosis executed via an intrinsic pathway. Additionally, the drug inhibited the formation and growth of CRPC cell colonies at low micromolar concentrations. A global proteome analysis performed using the 2D-PAGE technique, followed by MALDI-MS and bioinformatical evaluation, revealed alterations in the proteins involved in cellular processes such as metastatic potential, invasion, and apoptosis. Among others, the regulation of keratin 81, CrkII, IL-1β, and cathepsin B could be identified by our proteomics approach. The effects were validated on the protein level by a 2D Western blotting analysis. Our results demonstrate the promising anticancer activity of CA2-2 in a prostate cancer model and provide insights on the underlying mode of action. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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14 pages, 2159 KiB  
Article
Carotenoids from Starfish Patiria pectinifera: Therapeutic Activity in Models of Inflammatory Diseases
by Aleksandr M. Popov, Emma P. Kozlovskaya, Anna A. Klimovich, Tatyana A. Rutckova, Aleksey I. Vakhrushev, Dmitry M. Hushpulian, Irina G. Gazaryan, Vyacheslav V. Makhankov, Oksana M. Son and Liudmila A. Tekutyeva
Mar. Drugs 2023, 21(9), 470; https://doi.org/10.3390/md21090470 - 27 Aug 2023
Cited by 3 | Viewed by 1897
Abstract
The carotenoids mixture (MC) isolated from the starfish Patiria. pectinifera contains more than 50% astaxanthin, 4–6% each zeaxanthine and lutein, and less pharmacologically active components such as free fatty acids and their glycerides. Astaxanthin, the major component of MC, belongs to the xanthophyll [...] Read more.
The carotenoids mixture (MC) isolated from the starfish Patiria. pectinifera contains more than 50% astaxanthin, 4–6% each zeaxanthine and lutein, and less pharmacologically active components such as free fatty acids and their glycerides. Astaxanthin, the major component of MC, belongs to the xanthophyll class of carotenoids, and is well known for its antioxidant properties. In this work, in vitro and in vivo studies on the biological activity of MC were carried out. The complex was shown to exhibit anti-inflammatory, anti-allergic and cancer-preventive activity, without any toxicity at a dose of 500 mg/kg. MC effectively improves the clinical picture of the disease progressing, as well as normalizing the cytokine profile and the antioxidant defense system in the in vivo animal models of inflammatory diseases, namely: skin carcinogenesis, allergic contact dermatitis (ACD) and systemic inflammation (SI). In the skin carcinogenesis induced by 7,12-dimethylbenzanthracene, the incidence of papillomas was decreased 1.5 times; 1% MC ointment form in allergic contact dermatitis showed an 80% reduced severity of pathomorphological skin manifestations. Obtained results show that MC from starfish P. pectinifera is an effective remedy for the treatment and prevention of inflammatory processes. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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13 pages, 2768 KiB  
Article
Petrosamine Revisited. Experimental and Computational Investigation of Solvatochromism, Tautomerism and Free Energy Landscapes of a Pyridoacridinium Quaternary Salt
by Christopher J. Gartshore, Xiao Wang, Yongxuan Su and Tadeusz F. Molinski
Mar. Drugs 2023, 21(8), 446; https://doi.org/10.3390/md21080446 - 11 Aug 2023
Cited by 2 | Viewed by 1523
Abstract
Petrosamine (1)—a colored pyridoacridine alkaloid from the Belizean sponge, Petrosia sp., that is also a potent inhibitor of acetylcholine esterase (AChE)—was investigated by spectroscopic and computational methods. Analysis of the petrosamine-free energy landscapes, pKa and tautomerism, revealed an accurate [...] Read more.
Petrosamine (1)—a colored pyridoacridine alkaloid from the Belizean sponge, Petrosia sp., that is also a potent inhibitor of acetylcholine esterase (AChE)—was investigated by spectroscopic and computational methods. Analysis of the petrosamine-free energy landscapes, pKa and tautomerism, revealed an accurate electronic depiction of the molecular structure of 1 as the di-keto form, with a net charge of q = +1, rather than a dication (q = +2) under ambient conditions of isolation-purification. The pronounced solvatochromism (UV-vis) reported for 1, and related analogs were investigated in detail and is best explained by charge delocalization and stabilization of the ground state (HOMO) of 1 rather than an equilibrium of competing tautomers. Refinement of the molecular structure 1 by QM methods complements published computational docking studies to define the contact points in the enzyme active site that may improve the design of new AChE inhibitors based on the pyridoacridine alkaloid molecular skeleton. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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23 pages, 5612 KiB  
Article
Analogs of 6-Bromohypaphorine with Increased Agonist Potency for α7 Nicotinic Receptor as Anti-Inflammatory Analgesic Agents
by Igor A. Ivanov, Andrei E. Siniavin, Victor A. Palikov, Dmitry A. Senko, Irina V. Shelukhina, Lyubov A. Epifanova, Lucy O. Ojomoko, Svetlana Y. Belukhina, Nikita A. Prokopev, Mariia A. Landau, Yulia A. Palikova, Vitaly A. Kazakov, Natalia A. Borozdina, Arina V. Bervinova, Igor A. Dyachenko, Igor E. Kasheverov, Victor I. Tsetlin and Denis S. Kudryavtsev
Mar. Drugs 2023, 21(6), 368; https://doi.org/10.3390/md21060368 - 20 Jun 2023
Viewed by 2058
Abstract
Hypaphorines, tryptophan derivatives, have anti-inflammatory activity, but their mechanism of action was largely unknown. Marine alkaloid L-6-bromohypaphorine with EC50 of 80 μM acts as an agonist of α7 nicotinic acetylcholine receptor (nAChR) involved in anti-inflammatory regulation. We designed the 6-substituted hypaphorine analogs [...] Read more.
Hypaphorines, tryptophan derivatives, have anti-inflammatory activity, but their mechanism of action was largely unknown. Marine alkaloid L-6-bromohypaphorine with EC50 of 80 μM acts as an agonist of α7 nicotinic acetylcholine receptor (nAChR) involved in anti-inflammatory regulation. We designed the 6-substituted hypaphorine analogs with increased potency using virtual screening of their binding to the α7 nAChR molecular model. Fourteen designed analogs were synthesized and tested in vitro by calcium fluorescence assay on the α7 nAChR expressed in neuro 2a cells, methoxy ester of D-6-iodohypaphorine (6ID) showing the highest potency (EC50 610 nM), being almost inactive toward α9α10 nAChR. The macrophages cytometry revealed an anti-inflammatory activity, decreasing the expression of TLR4 and increasing CD86, similarly to the action of PNU282987, a selective α7 nAChR agonist. 6ID administration in doses 0.1 and 0.5 mg/kg decreased carrageenan-induced allodynia and hyperalgesia in rodents, in accord with its anti-inflammatory action. Methoxy ester of D-6-nitrohypaphorine demonstrated anti-oedemic and analgesic effects in arthritis rat model at i.p. doses 0.05–0.26 mg/kg. Tested compounds showed excellent tolerability with no acute in vivo toxicity in dosages up to 100 mg/kg i.p. Thus, combining molecular modelling and natural product-inspired drug design improved the desired activity of the chosen nAChR ligand. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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15 pages, 9316 KiB  
Article
Development of Novel Pharmaceutical Forms of the Marine Bioactive Pigment Echinochrome A Enabling Alternative Routes of Administration
by Stefanos Kikionis, Paraskevi Papakyriakopoulou, Panagiotis Mavrogiorgis, Elena A. Vasileva, Natalia P. Mishchenko, Sergey A. Fedoreyev, Georgia Valsami, Efstathia Ioannou and Vassilios Roussis
Mar. Drugs 2023, 21(4), 250; https://doi.org/10.3390/md21040250 - 18 Apr 2023
Cited by 2 | Viewed by 2967
Abstract
Echinochrome A (EchA), a marine bioactive pigment isolated from various sea urchin species, is the active agent of the clinically approved drug Histochrome®. EchA is currently only available in the form of an isotonic solution of its di- and tri-sodium salts [...] Read more.
Echinochrome A (EchA), a marine bioactive pigment isolated from various sea urchin species, is the active agent of the clinically approved drug Histochrome®. EchA is currently only available in the form of an isotonic solution of its di- and tri-sodium salts due to its poor water solubility and sensitivity to oxidation. Electrospun polymeric nanofibers have lately emerged as promising drug carriers capable of improving the dissolution and bioavailability of drugs with limited water solubility. In the current study, EchA isolated from sea urchins of the genus Diadema collected at the island of Kastellorizo was incorporated in electrospun micro-/nanofibrous matrices composed of polycaprolactone and polyvinylpyrrolidone in various combinations. The physicochemical properties of the micro-/nanofibers were characterized using SEM, FT-IR, TGA and DSC analyses. The fabricated matrices exhibited variable dissolution/release profiles of EchA, as evidenced in in vitro experiments using gastrointestinal-like fluids (pH 1.2, 4.5 and 6.8). Ex vivo permeability studies using the EchA-loaded micro-/nanofibrous matrices showed an increased permeation of EchA across the duodenum barrier. The results of our study clearly show that electrospun polymeric micro-/nanofibers represent promising carriers for the development of new pharmaceutical formulations with controlled release, as well as increased stability and solubility of EchA, suitable for oral administration, while offering the potential for targeted delivery. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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14 pages, 17383 KiB  
Article
Physicochemical Properties and Antiherpetic Activity of κ-Carrageenan Complex with Chitosan
by Viktoriya N. Davydova, Natalya V. Krylova, Olga V. Iunikhina, Aleksandra V. Volod’ko, Evgeniya A. Pimenova, Mikhail Y. Shchelkanov and Irina M. Yermak
Mar. Drugs 2023, 21(4), 238; https://doi.org/10.3390/md21040238 - 13 Apr 2023
Cited by 4 | Viewed by 2199
Abstract
Nanoparticles formation is one of the ways to modulate the physicochemical properties and enhance the activity of original polysaccharides. For this purpose, based on the polysaccharide of red algae, κ-carrageenan (κ-CRG), it polyelectrolyte complex (PEC), with chitosan, were obtained. The complex formation was [...] Read more.
Nanoparticles formation is one of the ways to modulate the physicochemical properties and enhance the activity of original polysaccharides. For this purpose, based on the polysaccharide of red algae, κ-carrageenan (κ-CRG), it polyelectrolyte complex (PEC), with chitosan, were obtained. The complex formation was confirmed by ultracentrifugation in a Percoll gradient, with dynamic light scattering. According to electron microscopy and DLS, PEC is dense spherical particles with sizes in the range of 150–250 nm. A decrease in the polydispersity of the initial CRG was detected after the PEC formation. Simultaneous exposure of Vero cells with the studied compounds and herpes simplex virus type 1 (HSV-1) showed that the PEC exhibited significant antiviral activity, effectively inhibiting the early stages of virus–cell interaction. A two-fold increase in the antiherpetic activity (selective index) of PEC compared to κ-CRG was shown, which may be due to a change in the physicochemical characteristics of κ-CRG in PEC. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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14 pages, 869 KiB  
Article
Chilensosides E, F, and G—New Tetrasulfated Triterpene Glycosides from the Sea Cucumber Paracaudina chilensis (Caudinidae, Molpadida): Structures, Activity, and Biogenesis
by Alexandra S. Silchenko, Sergey A. Avilov, Roman S. Popov, Pavel S. Dmitrenok, Ekaterina A. Chingizova, Boris B. Grebnev, Anton B. Rasin and Vladimir I. Kalinin
Mar. Drugs 2023, 21(2), 114; https://doi.org/10.3390/md21020114 - 5 Feb 2023
Cited by 2 | Viewed by 2484
Abstract
Three new tetrasulfated triterpene glycosides, chilensosides E (1), F (2), and G (3), have been isolated from the Far-Eastern sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D [...] Read more.
Three new tetrasulfated triterpene glycosides, chilensosides E (1), F (2), and G (3), have been isolated from the Far-Eastern sea cucumber Paracaudina chilensis (Caudinidae, Molpadida). The structures were established based on extensive analysis of 1D and 2D NMR spectra and confirmed by HR-ESI-MS data. The compounds differ in their carbohydrate chains, namely in the number of monosaccharide residues (five or six) and in the positions of sulfate groups. Chilensosides E (1) and F (2) are tetrasulfated pentaosides with the position of one of the sulfate groups at C-3 Glc3, and chilensoside G (3) is a tetrasulfated hexaoside. The biogenetic analysis of the glycosides of P. chilensis has revealed that the structures form a network due to the attachment of sulfate groups to almost all possible positions. The upper semi-chain is sulfated earlier in the biosynthetic process than the lower one. Noticeably, the presence of a sulfate group at C-3 Glc3—a terminal monosaccharide residue in the bottom semi-chain of compounds 1 and 2—excludes the possibility of this sugar chain’s further elongation. Presumably, the processes of glycosylation and sulfation are concurrent biosynthetic stages. They can be shifted in time in relation to each other, which is a characteristic feature of the mosaic type of biosynthesis. The hemolytic action of compounds 1–3 against human erythrocytes and cytotoxic activities against five human cancer cell lines were tested. The compounds showed moderate hemolytic activity but were inactive against cancer cells, probably because of their structural peculiarities, such as the combination of positions of four sulfate groups. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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15 pages, 2183 KiB  
Article
New Guanidine Alkaloids Batzelladines O and P from the Marine Sponge Monanchora pulchra Induce Apoptosis and Autophagy in Prostate Cancer Cells
by Sergey A. Dyshlovoy, Larisa K. Shubina, Tatyana N. Makarieva, Alla G. Guzii, Jessica Hauschild, Nadja Strewinsky, Dmitrii V. Berdyshev, Ekaterina K. Kudryashova, Alexander S. Menshov, Roman S. Popov, Pavel S. Dmitrenok, Markus Graefen, Carsten Bokemeyer and Gunhild von Amsberg
Mar. Drugs 2022, 20(12), 738; https://doi.org/10.3390/md20120738 - 25 Nov 2022
Cited by 3 | Viewed by 2459
Abstract
Two new guanidine alkaloids, batzelladines O (1) and P (2), were isolated from the deep-water marine sponge Monanchora pulchra. The structures of these metabolites were determined by NMR spectroscopy, mass spectrometry, and ECD. The isolated compounds exhibited cytotoxic activity [...] Read more.
Two new guanidine alkaloids, batzelladines O (1) and P (2), were isolated from the deep-water marine sponge Monanchora pulchra. The structures of these metabolites were determined by NMR spectroscopy, mass spectrometry, and ECD. The isolated compounds exhibited cytotoxic activity in human prostate cancer cells PC3, PC3-DR, and 22Rv1 at low micromolar concentrations and inhibited colony formation and survival of the cancer cells. Batzelladines O (1) and P (2) induced apoptosis, which was detected by Western blotting as caspase-3 and PARP cleavage. Additionally, induction of pro-survival autophagy indicated as upregulation of LC3B-II and suppression of mTOR was observed in the treated cells. In line with this, the combination with autophagy inhibitor 3-methyladenine synergistically increased the cytotoxic activity of batzelladines O (1) and P (2). Both compounds were equally active in docetaxel-sensitive and docetaxel-resistant prostate cancer cells, despite exhibiting a slight p-glycoprotein substrate-like activity. In combination with docetaxel, an additive effect was observed. In conclusion, the isolated new guanidine alkaloids are promising drug candidates for the treatment of taxane-resistant prostate cancer. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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16 pages, 1135 KiB  
Article
New Ceramides and Cerebrosides from the Deep-Sea Far Eastern Starfish Ceramaster patagonicus
by Timofey V. Malyarenko, Viktor M. Zakharenko, Alla A. Kicha, Alexandra S. Kuzmich, Olesya S. Malyarenko, Anatoly I. Kalinovsky, Roman S. Popov, Vasily I. Svetashev and Natalia V. Ivanchina
Mar. Drugs 2022, 20(10), 641; https://doi.org/10.3390/md20100641 - 14 Oct 2022
Cited by 3 | Viewed by 2707
Abstract
Three new ceramides (1–3) and three new cerebrosides (4, 8, and 9), along with three previously known cerebrosides (ophidiocerebrosides C (5), D (6), and CE-3-2 (7)), were isolated from [...] Read more.
Three new ceramides (1–3) and three new cerebrosides (4, 8, and 9), along with three previously known cerebrosides (ophidiocerebrosides C (5), D (6), and CE-3-2 (7)), were isolated from a deep-sea starfish species, the orange cookie starfish Ceramaster patagonicus. The structures of 1−4, 8, and 9 were determined by the NMR and ESIMS techniques and also through chemical transformations. Ceramides 1–3 contain iso-C21 or C23 Δ9-phytosphingosine as a long-chain base and have C16 or C17 (2R)-2-hydroxy-fatty acids of the normal type. Cerebroside 4 contains C22 Δ9-sphingosine anteiso-type as a long-chain base and (2R)-2-hydroxyheptadecanoic acid of the normal type, while compounds 8 and 9 contain saturated C-17 phytosphingosine anteiso-type as a long-chain base and differ from each other in the length of the polymethylene chain of (2R)-2-hydroxy-fatty acids of the normal type: C23 in 8 and C24 in 9. All the new cerebrosides (4, 8, and 9) have β-D-glucopyranose as a monosaccharide residue. The composition of neutral sphingolipids from C. patagonicus was described for the first time. The investigated compounds 1–3, 5–7, and 9 exhibit slight to moderate cytotoxic activity against human cancer cells (HT-29, SK-MEL-28, and MDA-MB-231) and normal embryonic kidney cells HEK293. Compounds 2, 5, and 6 at a concentration of 20 µM inhibit colony formation of MDA-MB-231 cells by 68%, 54%, and 68%, respectively. The colony-inhibiting activity of compounds 2, 5, and 6 is comparable to the effect of doxorubicin, which reduces the number of colonies by 70% at the same concentration. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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15 pages, 776 KiB  
Communication
1-O-Alkylglycerol Ethers from the Marine Sponge Guitarra abbotti and Their Cytotoxic Activity
by Sergey A. Dyshlovoy, Sergey N. Fedorov, Vasily I. Svetashev, Tatiana N. Makarieva, Anatoliy I. Kalinovsky, Olga P. Moiseenko, Vladimir B. Krasokhin, Larisa K. Shubina, Alla G. Guzii, Gunhild von Amsberg and Valentin A. Stonik
Mar. Drugs 2022, 20(7), 409; https://doi.org/10.3390/md20070409 - 22 Jun 2022
Cited by 2 | Viewed by 2782
Abstract
The cytotoxicity-bioassay-guided fractionation of the ethanol extract from the marine sponge Guitarra abbotti, whose 1-O-alkyl-sn-glycerol ethers (AGEs) have not been investigated so far, led to the isolation of a complex lipid fraction containing, along with previously known compounds, [...] Read more.
The cytotoxicity-bioassay-guided fractionation of the ethanol extract from the marine sponge Guitarra abbotti, whose 1-O-alkyl-sn-glycerol ethers (AGEs) have not been investigated so far, led to the isolation of a complex lipid fraction containing, along with previously known compounds, six new lipids of the AGE type. The composition of the AGE fraction as well as the structures of 6 new and 22 previously known compounds were established using 1H and 13C NMR, GC/MS, and chemical conversion methods. The new AGEs were identified as: 1-O-(Z-docos-15-enyl)-sn-glycerol (1), 1-O-(Z-docos-17-enyl)-sn-glycerol (2), 1-O-(Z-tricos-15-enyl)-sn-glycerol (3), 1-O-(Z-tricos-16-enyl)-sn-glycerol (4), 1-O-(Z-tricos-17-enyl)-sn-glycerol (5), and 1-O-(Z-tetracos-15-enyl)-sn-glycerol (6). The isolated AGEs show weak cytotoxic activity in THP-1, HL-60, HeLa, DLD-1, SNU C4, SK-MEL-28, and MDA-MB-231 human cancer cells. A further cytotoxicity analysis in JB6 P+ Cl41 cells bearing mutated MAP kinase genes revealed that ERK2 and JNK1 play a cytoprotective role in the cellular response to the AGE-induced cytotoxic effects. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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Review

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23 pages, 6544 KiB  
Review
Host Defense Proteins and Peptides with Lipopolysaccharide-Binding Activity from Marine Invertebrates and Their Therapeutic Potential in Gram-Negative Sepsis
by Tamara Fedorovna Solov’eva, Svetlana Ivanovna Bakholdina and Gennadii Alexandrovich Naberezhnykh
Mar. Drugs 2023, 21(11), 581; https://doi.org/10.3390/md21110581 - 7 Nov 2023
Viewed by 2420
Abstract
Sepsis is a life-threatening complication of an infectious process that results from the excessive and uncontrolled activation of the host’s pro-inflammatory immune response to a pathogen. Lipopolysaccharide (LPS), also known as endotoxin, which is a major component of Gram-negative bacteria’s outer membrane, plays [...] Read more.
Sepsis is a life-threatening complication of an infectious process that results from the excessive and uncontrolled activation of the host’s pro-inflammatory immune response to a pathogen. Lipopolysaccharide (LPS), also known as endotoxin, which is a major component of Gram-negative bacteria’s outer membrane, plays a key role in the development of Gram-negative sepsis and septic shock in humans. To date, no specific and effective drug against sepsis has been developed. This review summarizes data on LPS-binding proteins from marine invertebrates (ILBPs) that inhibit LPS toxic effects and are of interest as potential drugs for sepsis treatment. The structure, physicochemical properties, antimicrobial, and LPS-binding/neutralizing activity of these proteins and their synthetic analogs are considered in detail. Problems that arise during clinical trials of potential anti-endotoxic drugs are discussed. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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Other

10 pages, 620 KiB  
Commentary
Fucoidans of Brown Algae: Comparison of Sulfated Polysaccharides from Fucus vesiculosus and Ascophyllum nodosum
by Anatolii I. Usov, Maria I. Bilan, Nadezhda E. Ustyuzhanina and Nikolay E. Nifantiev
Mar. Drugs 2022, 20(10), 638; https://doi.org/10.3390/md20100638 - 13 Oct 2022
Cited by 19 | Viewed by 3138
Abstract
Preparations of sulfated polysaccharides obtained from brown algae are known as fucoidans. These biopolymers have attracted considerable attention due to many biological activities which may find practical applications. Two Atlantic representatives of Phaeophyceae, namely, Fucus vesiculosus and Ascophyllum nodosum, belonging to the [...] Read more.
Preparations of sulfated polysaccharides obtained from brown algae are known as fucoidans. These biopolymers have attracted considerable attention due to many biological activities which may find practical applications. Two Atlantic representatives of Phaeophyceae, namely, Fucus vesiculosus and Ascophyllum nodosum, belonging to the same order Fucales, are popular sources of commercial fucoidans, which often regarded as very similar in chemical composition and biological actions. Nevertheless, these two fucoidan preparations are polysaccharide mixtures which differ considerably in amount and chemical nature of components, and hence, this circumstance should be taken into account in the investigation of their biological properties and structure–activity relationships. In spite of these differences, fractions with carefully characterized structures prepared from both fucoidans may have valuable applications in drug development. Full article
(This article belongs to the Special Issue Honoring Prof. Dr. Valentin A. Stonik for His Outstanding Contribution to Marine Natural Product Chemistry on the Occasion of His 80th Birthday)
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