42 results on '"Stonik, Valentin A."'
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2. New diterpenes from the marine sponge Spongionella sp. overcome drug resistance in prostate cancer by inhibition of P-glycoprotein.
- Author
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Dyshlovoy SA, Shubina LK, Makarieva TN, Hauschild J, Strewinsky N, Guzii AG, Menshov AS, Popov RS, Grebnev BB, Busenbender T, Oh-Hohenhorst SJ, Maurer T, Tilki D, Graefen M, Bokemeyer C, Stonik VA, and von Amsberg G
- Subjects
- ATP Binding Cassette Transporter, Subfamily B metabolism, ATP Binding Cassette Transporter, Subfamily B, Member 1 metabolism, Animals, Docetaxel pharmacology, Drug Resistance, Humans, Male, Molecular Structure, Diterpenes chemistry, Porifera metabolism, Prostatic Neoplasms drug therapy
- Abstract
Spongian diterpenes are a group of marine natural compounds possessing various biological activities. However, their anticancer activity is still poorly studied and understood. We isolated six spongian diterpenes from the marine sponge Spongionella sp., including one new spongionellol A and five previously known molecules. The structures were elucidated using a detailed analysis MS and NMR spectra as well as by comparison with previously reported data. Two of them, namely, spongionellol A and 15,16-dideoxy-15α,17β-dihydroxy-15,17-oxidospongian-16-carboxylate-15,17-diacetate exhibited high activity and selectivity in human prostate cancer cells, including cells resistant to hormonal therapy and docetaxel. The mechanism of action has been identified as caspase-dependent apoptosis. Remarkably, both compounds were able to suppress expression of androgen receptor (AR) and AR-splice variant 7, as well as AR-dependent signaling. The isolated diterpenes effectively inhibited drug efflux mediated by multidrug-resistance protein 1 (MDR1; p-glycoprotein). Of note, a synergistic effect of the compounds with docetaxel, a substrate of p-glycoprotein, suggests resensitization of p-glycoprotein overexpressing cells to standard chemotherapy. In conclusion, the isolated spongian diterpenes possess high activity and selectivity towards prostate cancer cells combined with the ability to inhibit one of the main drug-resistance mechanism. This makes them promising candidates for combinational anticancer therapy., (© 2022. The Author(s).)
- Published
- 2022
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3. 1- O -Alkylglycerol Ethers from the Marine Sponge Guitarra abbotti and Their Cytotoxic Activity.
- Author
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Dyshlovoy SA, Fedorov SN, Svetashev VI, Makarieva TN, Kalinovsky AI, Moiseenko OP, Krasokhin VB, Shubina LK, Guzii AG, von Amsberg G, and Stonik VA
- Subjects
- Animals, Gas Chromatography-Mass Spectrometry, Glycerol pharmacology, Glyceryl Ethers pharmacology, Humans, Ethers pharmacology, Porifera
- 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, 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
1 H and13 C 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.- Published
- 2022
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4. Toporosides A and B, Cyclopentenyl-Containing ω-Glycosylated Fatty Acid Amides, and Toporosides C and D from the Northwestern Pacific Marine Sponge Stelodoryx toporoki .
- Author
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Guzii AG, Makarieva TN, Fedorov SN, Menshov AS, Denisenko VA, Popov RS, Yurchenko EA, Menchinskaya ES, Grebnev BB, Iarotsckaia VV, Kim NY, and Stonik VA
- Subjects
- Animals, Fatty Acids chemistry, Magnetic Resonance Spectroscopy, Molecular Structure, Amides chemistry, Porifera chemistry
- Abstract
Toporosides A-D ( 1 - 4 ), new ω-glycosylated fatty acid amides, were isolated from the sponge Stelodoryx toporoki . The structures of these compounds, including absolute configurations of stereogenic centers, were established using analysis of 1D and 2D NMR, ECD, and HR mass spectra as well as chemical transformations. Toporosides A ( 1 ) and B ( 2 ) are the first lipids containing a cyclopentenyl α,β-unsaturated carbonyl moiety in the polymethylene chain. Toporoside C ( 3 ) is likely a precursor, which undergoes intramolecular aldol condensation to produce 1 and 2 . Toporosides A, C, and D showed protective effects against TNF-α-induced injury in H9c2 cardiomyocytes.
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- 2022
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5. Oceanalin B, a Hybrid α,ω-Bifunctionalized Sphingoid Tetrahydroisoquinoline β-Glycoside from the Marine Sponge Oceanapia sp.
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Makarieva TN, Ivanchina NV, Dmitrenok PS, Guzii AG, Stonik VA, Dalisay DS, and Molinski TF
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- Animals, Antifungal Agents chemistry, Aquatic Organisms, Glycosides chemistry, Microbial Sensitivity Tests, Tetrahydroisoquinolines chemistry, Antifungal Agents pharmacology, Candida drug effects, Glycosides pharmacology, Porifera, Tetrahydroisoquinolines pharmacology
- Abstract
Oceanalin B ( 1 ), an α,ω-bipolar natural product belonging to a rare family of sphingoid tetrahydoisoquinoline β-glycosides, was isolated from the EtOH extract of the lyophilized marine sponge Oceanapia sp. as the second member of the series after oceanalin A ( 2 ) from the same animal. The compounds are of particular interest due to their biogenetically unexpected structures as well as their biological activities. The structure and absolute stereochemistry of 1 as a α,ω-bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside was elucidated using NMR, CD and MS spectral analysis and chemical degradation. Oceanalin B exhibited in vitro antifungal activity against Candida with a MIC of 25 μg/mL.glabrata with a MIC of 25 μg/mL.
- Published
- 2021
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6. New Isomalabaricane-Derived Metabolites from a Stelletta sp. Marine Sponge.
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Kolesnikova SA, Lyakhova EG, Kozhushnaya AB, Kalinovsky AI, Berdyshev DV, Popov RS, and Stonik VA
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- Alkynes chemistry, Animals, Porifera chemistry, Porifera metabolism, Terpenes chemistry, Triterpenes chemistry
- 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 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, 15 R ,23 S for globostelletin M and 15 S ,23 R for globostelletin N.
- Published
- 2021
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7. Urupocidin C: a new marine guanidine alkaloid which selectively kills prostate cancer cells via mitochondria targeting.
- Author
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Dyshlovoy SA, Kudryashova EK, Kaune M, Makarieva TN, Shubina LK, Busenbender T, Denisenko VA, Popov RS, Hauschild J, Fedorov SN, Bokemeyer C, Graefen M, Stonik VA, and von Amsberg G
- Subjects
- Animals, Cell Cycle Checkpoints, Cell Death, Male, Mitochondria pathology, Prostatic Neoplasms drug therapy, Tumor Cells, Cultured, Alkaloids pharmacology, Antineoplastic Agents pharmacology, Apoptosis, Guanidines pharmacology, Mitochondria drug effects, Porifera chemistry, Prostatic Neoplasms pathology
- Abstract
New bicyclic guanidine alkaloid, urupocidin C (Ur-C) along with the previously known urupocidin A (Ur-A) were isolated from the rare deep-sea marine sponge Monanchora pulchra, harvested in Northwestern Pacific waters. The unique structure of Ur-C was elucidated using 1D and 2D NMR spectroscopy as well as mass spectra. We discovered a promising selectivity of both alkaloids for human prostate cancer (PCa) cells, including highly drug-resistant lines, compared to non-malignant cells. In cancer cells, marine derived compounds were able to induce G1- and S-cell cycle arrest as well as caspase-mediated cell death. For the first time we have identified mitochondrial targeting as a central mechanism of anticancer action for these and similar molecules. Thus, treatment with the isolated alkaloids resulted in mitochondrial membrane permeabilization consequently leading to the release of cytotoxic mitochondrial proteins to cellular cytoplasm, ROS upregulation, consequent activation of caspase-9 and -3, followed by PARP cleavage, DNA fragmentation, and apoptosis. Moreover, synergistic effects were observed when Ur-A and Ur-C were combined with clinically approved PARP inhibitor olaparib. Finally, these alkaloids exhibited additive effects in combination with docetaxel and androgen receptor inhibitor enzalutamide, both applied in PCa therapy. In conclusion, urupocidin-like compounds are promising lead molecules for the development of new drugs for the treatment of advanced PCa.
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- 2020
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8. Cyclobutastellettolides A and B, C 19 Norterpenoids from a Stelletta sp. Marine Sponge.
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Kolesnikova SA, Lyakhova EG, Kalinovsky AI, Berdyshev DV, Pislyagin EA, Popov RS, Grebnev BB, Makarieva TN, Minh CV, and Stonik VA
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- Animals, Macrophages, Peritoneal drug effects, Macrophages, Peritoneal metabolism, Mice, Molecular Structure, Porifera metabolism, Reactive Oxygen Species metabolism, Porifera chemistry, Terpenes chemistry, Terpenes pharmacology
- Abstract
Two novel C
19 terpenoids ( 1 , 2 ) with an unprecedented carbon skeleton ( A ) were isolated from a Stelletta sp. sponge collected from Vietnamese waters. Their structures and absolute configurations were established by extensive NMR, MS, and ECD analyses together with quantum chemical modeling and biogenetic considerations. The probable pathways of biogenesis of 1 and 2 from isomalabaricane triterpenoids are discussed. Compounds 1 and 2 significantly increase the production of reactive oxygen species in murine peritoneal macrophages.- Published
- 2019
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9. Guitarrins A-E and Aluminumguitarrin A: 5-Azaindoles from the Northwestern Pacific Marine Sponge Guitarra fimbriata.
- Author
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Guzii AG, Makarieva TN, Denisenko VA, Gerasimenko AV, Udovenko AA, Popov RS, Dmitrenok PS, Golotin VA, Fedorov SN, Grebnev BB, and Stonik VA
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- Aluminum Compounds chemistry, Aluminum Compounds isolation & purification, Animals, Aza Compounds chemistry, Aza Compounds isolation & purification, Indoles chemistry, Indoles isolation & purification, Magnetic Resonance Spectroscopy, Mass Spectrometry, Molecular Structure, Aluminum Compounds pharmacology, Aza Compounds pharmacology, Indoles pharmacology, Porifera chemistry
- Abstract
Guitarrins A-E (1-5), the first natural 5-azaindoles, and aluminumguitarrin A (1a), the first aluminum-containing compound from marine invertebrates, were isolated from the sponge Guitarra fimbriata. The structures of these compounds were established using detailed analysis of 1D and 2D NMR data, mass spectra, and X-ray analysis of 1 and 1a. Compound 3 was proved to be a natural inhibitor of alkaline phosphatase.
- Published
- 2019
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10. Melonoside B and Melonosins A and B, Lipids Containing Multifunctionalized ω-Hydroxy Fatty Acid Amides from the Far Eastern Marine Sponge Melonanchora kobjakovae.
- Author
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Guzii AG, Makarieva TN, Denisenko VA, Dmitrenok PS, Popov RS, Kuzmich AS, Fedorov SN, Krasokhin VB, Kim NY, and Stonik VA
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- Animals, Cell Line, Fatty Acids chemistry, Fatty Acids pharmacology, Magnetic Resonance Spectroscopy, Molecular Structure, NF-kappa B antagonists & inhibitors, Fatty Acids isolation & purification, Porifera chemistry
- Abstract
Melonoside B (1) and melonosins B (2) and A (3), new lipids based on polyoxygenated fatty acid amides, and known melonoside A (4) were isolated from two different collections of the marine sponge Melonanchora kobjakovae. The structures of these compounds, including their absolute configurations, were established using detailed analysis of 1D and 2D NMR, ECD, and mass spectra as well as chemical transformations. Melonosins 2 and 3 inhibit AP-1- and NF-kB-dependent transcriptional activities in JB6 Cl41 cells at noncytotoxic concentrations, demonstrating potential cancer preventive activity.
- Published
- 2018
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11. Oxysterols from a Marine Sponge Inflatella sp. and Their Action in 6-Hydroxydopamine-Induced Cell Model of Parkinson's Disease.
- Author
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Kolesnikova SA, Lyakhova EG, Kalinovsky AI, Popov RS, Yurchenko EA, and Stonik VA
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- Animals, Antiparkinson Agents chemistry, Antiparkinson Agents isolation & purification, Antiparkinson Agents pharmacology, Cell Line, Tumor, Cell Survival drug effects, Mice, Oxidopamine, Oxysterols isolation & purification, Parkinsonian Disorders chemically induced, Parkinsonian Disorders metabolism, Reactive Oxygen Species metabolism, Neuroprotective Agents chemistry, Neuroprotective Agents pharmacology, Oxysterols chemistry, Oxysterols pharmacology, Parkinsonian Disorders drug therapy, Porifera chemistry
- Abstract
Four new oxysterols 1 ⁻ 4 along with previously known oxygenated sterols 5 ⁻ 14 were isolated from the sponge Inflatella sp., collected from the Sea of Okhotsk. Structures of 1 ⁻ 4 were elucidated by the detailed NMR spectroscopic and mass-spectrometric analyses as well as by comparison of the corresponding experimental data with those reported in literature. The influence of compounds 1 ⁻ 14 on the viability of neuronal Neuro2a cells treated by 6-hydroxydopamine and reactive oxygen species (ROS) formation in these cells was investigated.
- Published
- 2018
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12. Erylosides F 8 , V 1 -V 3 , and W-W 2 - New triterpene oligoglycosides from the Carribean sponge Erylus goffrilleri.
- Author
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Antonov AS, Kalinovsky AI, Afiyatullov SS, Leshchenko EV, Dmitrenok PS, Yurchenko EA, Kalinin VI, and Stonik VA
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- Animals, Glycosides chemistry, Porifera chemistry, Steroids chemistry, Triterpenes chemistry
- Abstract
Seven new triterpene glycosides, erylosides F
8 (1), V1 (2), V2 (3), V3 (4), W (5), W1 (6) and W2 (7), were isolated from a Carribean sponge Erylus goffrilleri collected from the Carribean Sea near the Arrecife-Seco reef (Cuba). Structures of the glycosides were determined using1 H and13 C NMR spectroscopy, including 2D NMR procedures (1 H-1 H COSY,1 H-13 С HMBC,1 H-13 С HSQC and NOESY) and HR ESI mass spectrometry. Erylosides 1 and 4 have 14-carboxy-24,25-dimethyllanost-8(9)-en-3β,25-diol as aglycone whereas glycosides 2, 3, 5, 6 and 7 are 14-carboxy-24-acetoxy-24-methyllanost-8(9)-en-3β-ol glycoconjugates. Cytotoxic activities of the isolated compounds against Ehrlich carcinoma cells and hemolysis were examined and their dependence on eryloside structure was evaluated., (Copyright © 2017. Published by Elsevier Ltd.)- Published
- 2017
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13. Monanchoxymycalins A and B, New Hybrid Pentacyclic Guanidine Alkaloids from the Far-Eastern Marine Sponge Monanchora pulchra.
- Author
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Tabakmakher KM, Makarieva TN, Shubina LK, Denisenko VA, Popov RS, Kuzmich AS, Lee HS, Lee YJ, and Stonik VA
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- Alkaloids chemistry, Alkaloids pharmacology, Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Cell Line, Tumor, Cell Survival drug effects, Guanidines chemistry, Guanidines pharmacology, Humans, Alkaloids isolation & purification, Antineoplastic Agents isolation & purification, Guanidines isolation & purification, Porifera chemistry
- Abstract
The new pentacyclic guanidine alkaloids, monanchoxymycalin A (1) and monanchoxymycalin B (2) were isolated from the Far-Eastern marine sponge Monanchora pulchra. Their structures were assigned on the basis of detailed analysis of lD- and 2D-NMR spectroscopic and mass spectrometric data. Compounds 1 and 2 exhibited potent cytotoxic activities against cervical epithelioid carcinoma HeLa cells and breast adenocarcinoma MDA-MB231 cells.
- Published
- 2016
14. Melonoside A: An ω-Glycosylated Fatty Acid Amide from the Far Eastern Marine Sponge Melonanchora kobjakovae.
- Author
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Guzii AG, Makarieva TN, Denisenko VA, Dmitrenok PS, Kuzmich AS, Dyshlovoy SA, von Amsberg G, Krasokhin VB, and Stonik VA
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- Amides isolation & purification, Amides pharmacology, Animals, Antineoplastic Agents isolation & purification, Antineoplastic Agents pharmacology, Autophagy drug effects, Cell Line, Tumor, Drug Screening Assays, Antitumor, Fatty Acids isolation & purification, Fatty Acids pharmacology, Glucuronates isolation & purification, Glucuronates pharmacology, Humans, Magnetic Resonance Spectroscopy, Molecular Structure, Amides chemistry, Antineoplastic Agents chemistry, Fatty Acids chemistry, Glucuronates chemistry, Porifera chemistry
- Abstract
Melonoside A (1), the first representative of a new class of ω-glycosylated fatty acid amides, was isolated from the Far Eastern marine sponge Melonanchora kobjakovae. The structure of 1, including absolute configuration, was established using detailed analysis of 1D and 2D NMR, CD, and mass spectra as well as chemical transformations. Compound 1 induces autophagy of human cisplatin-resistant germinal tumor cells NCCIT-R.
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- 2016
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15. Guanidine Alkaloids from the Marine Sponge Monanchora pulchra Show Cytotoxic Properties and Prevent EGF-Induced Neoplastic Transformation in Vitro.
- Author
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Dyshlovoy SA, Tabakmakher KM, Hauschild J, Shchekaleva RK, Otte K, Guzii AG, Makarieva TN, Kudryashova EK, Fedorov SN, Shubina LK, Bokemeyer C, Honecker F, Stonik VA, and von Amsberg G
- Subjects
- Alkaloids chemistry, Animals, Cell Cycle Checkpoints drug effects, Cell Death drug effects, Cell Line, Cell Line, Tumor, Cell Transformation, Neoplastic metabolism, Guanidine analogs & derivatives, Guanidine chemistry, Guanidine pharmacology, Guanidines chemistry, HeLa Cells, Humans, MAP Kinase Signaling System drug effects, Mice, Transcription Factor AP-1 metabolism, Tumor Suppressor Protein p53 metabolism, Alkaloids pharmacology, Cell Transformation, Neoplastic drug effects, Epidermal Growth Factor metabolism, Guanidines pharmacology, Porifera chemistry
- Abstract
Guanidine alkaloids from sponges Monanchora spp. represent diverse bioactive compounds, however, the mechanisms underlying bioactivity are very poorly understood. Here, we report results of studies on cytotoxic action, the ability to inhibit EGF-induced neoplastic transformation, and the effects on MAPK/AP-1 signaling of eight rare guanidine alkaloids, recently isolated from the marine sponge Monanchora pulchra, namely: monanchocidin A (1), monanchocidin B (2), monanchomycalin C (3), ptilomycalin A (4), monanchomycalin B (5), normonanchocidin D (6), urupocidin A (7), and pulchranin A (8). All of the compounds induced cell cycle arrest (apart from 8) and programmed death of cancer cells. Ptilomycalin A-like compounds 1-6 activated JNK1/2 and ERK1/2, following AP-1 activation and caused p53-independent programmed cell death. Compound 7 induced p53-independent cell death without activation of AP-1 or caspase-3/7, and the observed JNK1/2 activation did not contribute to the cytotoxic effect of the compound. Alkaloid 8 induced JNK1/2 (but not ERK1/2) activation leading to p53-independent cell death and strong suppression of AP-1 activity. Alkaloids 1-4, 7, and 8 were able to inhibit the EGF-induced neoplastic transformation of JB6 P⁺ Cl41 cells. Our results suggest that investigated guanidine marine alkaloids hold potential to eliminate human cancer cells and prevent cancer cell formation and spreading.
- Published
- 2016
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16. New Derivatives of Natural Acyclic Guanidine Alkaloids with TRPV Receptor-Regulating Properties.
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Ogurtsova EK, Makarieva TN, Korolkova YV, Andreev YA, Mosharova IV, Denisenko VA, Dmitrenok PS, Lee YJ, Grishin EV, and Stonik VA
- Subjects
- Animals, CHO Cells, Cricetulus, Guanidine chemical synthesis, Humans, Rats, Alkaloids chemical synthesis, Guanidine analogs & derivatives, Guanidines chemical synthesis, Porifera chemistry, TRPV Cation Channels antagonists & inhibitors
- Abstract
The guanidine alkaloids, dihydropulchranin A (2), prepared from pulchranin A from the sponge Monanchora pulchra, and hexadecylguanidine (3), a synthetic analog of pulchranins, were studied for their TRPV channel-regulating activities. Compound 2 was active as an inhibitor of rTRPV1 and hTRPV3 receptors with EC50 values of 24.3 and 59.1 μM, respectively. Hexadecylguanidine (3) was not active against these receptors.
- Published
- 2015
17. Pyridine Nucleosides Neopetrosides A and B from a Marine Neopetrosia sp. Sponge. Synthesis of Neopetroside A and Its β-Riboside Analogue.
- Author
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Shubina LK, Makarieva TN, Yashunsky DV, Nifantiev NE, Denisenko VA, Dmitrenok PS, Dyshlovoy SA, Fedorov SN, Krasokhin VB, Jeong SH, Han J, and Stonik VA
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- Adenosine Triphosphate analysis, Animals, Marine Biology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Nucleosides chemical synthesis, Pyridines chemical synthesis, Nucleosides chemistry, Nucleosides isolation & purification, Porifera chemistry, Pyridines chemistry, Pyridines isolation & purification
- Abstract
Neopetrosides A (1) and B (2), new naturally occurring ribosides of nicotinic acid with extremely rare α-N-glycoside linkages and residues of p-hydroxybenzoic and pyrrole-2-carboxylic acids attached to C-5', were isolated from a marine Neopetrosia sp. sponge. Structures 1 and 2 were determined by NMR and MS methods and confirmed by the synthesis of 1 and its β-riboside analogue (3). Neopetroside A (1) upregulates mitochondrial functions in cardiomyocytes.
- Published
- 2015
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18. Normonanchocidins A, B and D, New Pentacyclic Guanidine Alkaloids from the Far-Eastern Marine Sponge Monanchora pulchra.
- Author
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Tabakmakher KM, Makarieva TN, Denisenko VA, Guzii AG, Dmitrenok PS, Kuzmich AS, and Stonik VA
- Subjects
- Alkaloids isolation & purification, Animals, Guanidine chemistry, Guanidines chemistry, Magnetic Resonance Spectroscopy, Molecular Structure, Alkaloids chemistry, Guanidine analogs & derivatives, Porifera chemistry
- Abstract
New pentacyclic guanidine alkaloids, normonanchocidins A, B and D (1-3) along with the earlier known monanchocidin A were isolated from the Far-Eastern marine sponge Monanchora pulchra. Structures of 1-3 were elucidated using ID- and 2D-NMR spectroscopic and mass spectrometric data. Compound 1 and a mixture of 2 and 3 (1:1) exhibited cytotoxic activities against human leukemia THP-1 cells with IC50 values of 2.1 μM and 3.7 μM, respectively, and against cervix epithelial carcinoma HeLa cells with IC50 of 3.8 μM and 6.8 μM, respectively.
- Published
- 2015
19. Further study on Penares sp. from Vietnamese waters: minor lanostane and nor-lanostane triterpenes.
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Lyakhova EG, Kolesnikova SA, Kalinovsky AI, Dmitrenok PS, Nam NH, and Stonik VA
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- Animals, Ethanol chemistry, Vietnam, Porifera chemistry, Triterpenes chemistry, Triterpenes isolation & purification, Water
- Abstract
Eight new oxidized lanostane and nor-lanostane derivatives (1-8) along with the previously known penasterol (9) and 24-ethylcholesta-4,24(28)-dien-3-one (10) were isolated from a sponge Penares sp. collected from the Vietnamese waters. Structures of these minor compounds were elucidated by the detailed NMR spectroscopic and mass-spectrometric analyses and by comparison with earlier reported spectroscopic data. A hypothetic scheme of metabolism of the lanostane derivatives in sponges belonging to Penares and Erylus genera was proposed and discussed., (Copyright © 2015 Elsevier Inc. All rights reserved.)
- Published
- 2015
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20. Cerebrosides from a Far-Eastern Glass Sponge Aulosaccus sp.
- Author
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Santalova ЕА, Denisenko VА, Dmitrenok PS, Drozdov АL, and Stonik VA
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- Animals, Fatty Acids analysis, Magnetic Resonance Spectroscopy, Mass Spectrometry, Sphingolipids analysis, Cerebrosides analysis, Porifera chemistry
- Abstract
Nine new cerebrosides 1a-d, 2a, 2b, 3a-c were found in the extract of a Far-Eastern glass sponge Aulosaccus sp. (class Hexactinellida). These β-D-glucopyranosyl-(1 → 1)-ceramides contain sphingoid bases (2S,3S,4R,11Z)-2-aminoeicos-11-ene-1,3,4-triol (in 1a-d), (2S,3S,4R,13Z)-2-aminoeicos-13-ene-1,3,4-triol (in 2a, b) and (2S,3S,4R,13S*,14R*)-2-amino-13,14-methylene-eicosane-1,3,4-triol (in 3a-c), which are N-acylated by (2R,15Z)-2-hydroxydocos-15-enoic (in 1a, 2a, 3a), (2R,16Z)-2-hydroxytricos-16-enoic (in 1b, 2b, 3b), (2R,17Z)-2-hydroxytetracos-17-enoic (in 1d) and (2R)-2-hydroxydocosanoic (in 1c, 3c) acids. The monoenoic and cyclopropane-containing sphingoid bases of compounds 1a-d, 2a, 2b, 3a-c have not been found previously in any sphingolipids. The structures of the cerebrosides were elucidated on the basis of (1)H-, (13)C-NMR spectroscopy, mass spectrometry, optical rotation data and chemical transformations. A simplified method for the assignment of the absolute configuration of 2-hydroxy fatty acids by GC analysis of their (2R)- and (2S)-oct-2-yl esters was proposed.
- Published
- 2015
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21. Urupocidin A: a new, inducing iNOS expression bicyclic guanidine alkaloid from the marine sponge Monanchora pulchra.
- Author
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Makarieva TN, Ogurtsova EK, Denisenko VA, Dmitrenok PS, Tabakmakher KM, Guzii AG, Pislyagin EA, Es'kov AA, Kozhemyako VB, Aminin DL, Wang YM, and Stonik VA
- Subjects
- Alkaloids chemistry, Animals, Hydroxylamines, Inhibitory Concentration 50, Marine Biology, Mice, Molecular Structure, Nitric Oxide, Nuclear Magnetic Resonance, Biomolecular, Alkaloids pharmacology, Guanidines chemistry, Guanidines pharmacology, Nitric Oxide Synthase Type II drug effects, Porifera chemistry
- Abstract
Urupocidins A and B (1 and 2), bisguanidine alkaloids with an unprecedented skeleton system, derived from polyketide precursors and containing an unusual N-alkyl-N-hydroxyguanidine moiety, have been isolated from the sponge Monanhora pulchra. The structures of 1 and 2, including absolute configuration, were established using the detailed analysis of 1D and 2D NMR, CD, and mass spectra as well as chemical transformations. Compound 1 increases nitric oxide production in murine macrophages via inducing iNOS expression.
- Published
- 2014
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22. Isolation, structures, and biological activities of triterpenoids from a Penares sp. marine sponge.
- Author
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Kolesnikova SA, Lyakhova EG, Kalinovsky AI, Pushilin MA, Afiyatullov SSh, Yurchenko EA, Dyshlovoy SA, Minh CV, and Stonik VA
- Subjects
- Animals, Antineoplastic Agents chemistry, Crystallography, X-Ray, Drug Screening Assays, Antitumor, HL-60 Cells, Humans, Lanosterol analogs & derivatives, Marine Biology, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Triterpenes chemistry, Vietnam, Antineoplastic Agents isolation & purification, Antineoplastic Agents pharmacology, Porifera chemistry, Triterpenes isolation & purification, Triterpenes pharmacology
- Abstract
Six new triterpenoids (1-6) and the previously known penasterone, acetylpenasterol, and ergosta-4,24(28)-dien-3-one were isolated from a Penares sp. sponge collected from Vietnamese waters. Structures of the obtained compounds were established by extensive 1D and 2D NMR spectroscopy and mass spectrometry. Configurations of the triterpene epoxy lactones (1-4) were determined on the basis of NOESY and CD data and calculation of spin coupling constants and confirmed by X-ray crystallographic analysis of compound 2. The isolated triterpenoid 6 was cytotoxic against human leukemia HL-60 cells (IC₅₀ = 9.7 μM).
- Published
- 2013
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23. Pulchranins B and C, new acyclic guanidine alkaloids from the Far-Eastern marine sponge Monanchora pulchra.
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Makarieva TN, Ogurtsova EK, Korolkova YV, Andreev YA, Mosharova IV, Tabakmakher KM, Guzii AG, Denisenko VA, Dmitrenok PS, Lee HS, Grishin EV, and Stonik VA
- Subjects
- Alkaloids chemistry, Animals, Guanidines chemistry, Molecular Structure, Pacific Ocean, Alkaloids isolation & purification, Guanidines isolation & purification, Porifera chemistry, TRPV Cation Channels antagonists & inhibitors
- Abstract
New marine natural products, pulchranins B and C (2 and 3), were isolated from the marine sponge Monanchora pulchra and their structures were established using NMR and MS analysis. Compounds 2 and 3 were moderately active as inhibitors of TRPV1 (EC50 value of 95 and 183 microM, respectively) and less potent against TRPV3 and TRPA1 receptors.
- Published
- 2013
24. Glycosides from marine sponges (Porifera, Demospongiae): structures, taxonomical distribution, biological activities and biological roles.
- Author
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Kalinin VI, Ivanchina NV, Krasokhin VB, Makarieva TN, and Stonik VA
- Subjects
- Animals, Biological Products chemistry, Biological Products pharmacology, Glycosides chemistry, Glycosides pharmacology, Humans, Biological Products isolation & purification, Glycosides isolation & purification, Porifera chemistry
- Abstract
Literature data about glycosides from sponges (Porifera, Demospongiae) are reviewed. Structural diversity, biological activities, taxonomic distribution and biological functions of these natural products are discussed.
- Published
- 2012
- Full Text
- View/download PDF
25. New meroterpenoids from the marine sponge Aka coralliphaga.
- Author
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Shubina LK, Kalinovsky AI, Makarieva TN, Fedorov SN, Dyshlovoy SA, Dmitrenok PS, Kapustina II, Mollo E, Utkina NK, Krasokhin VB, Denisenko VA, and Stonik VA
- Subjects
- Animals, Free Radical Scavengers analysis, Molecular Structure, Terpenes chemistry, Porifera chemistry, Terpenes isolation & purification
- Abstract
Three new sulfated meroterpenoids containing sesquiterpene and hydroquinone moieties, namely siphonodictyal A sulfate (1), akadisulfate A (2) and akadisulfate B (3), along with the known siphonodictyal B3 and bis(sulfato)-cyclosiphonodictyol A were isolated from the sponge Aka coralliphaga. Their structures were elucidated on the basis of spectroscopic data. Akadisulfate B and siphonodictyal B3 showed a radical-scavenging activity comparable with that of the known lipophylic antioxidant BHT.
- Published
- 2012
26. New triterpene oligoglycosides from the Caribbean sponge Erylus formosus.
- Author
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Antonov AS, Kalinovsky AI, Dmitrenok PS, Kalinin VI, Stonik VA, Mollo E, and Cimino G
- Subjects
- Animals, Glycosides biosynthesis, Glycosides isolation & purification, Glycosylation, Porifera metabolism, Glycosides chemistry, Porifera chemistry, Triterpenes chemistry
- Abstract
Seven new triterpene glycosides, erylosides R(1) (1), T(1) (3), T(2) (4), T(3) (5), T(4) (6), T(5) (7), and T(6) (8) along with the known formoside (2) were isolated from the sponge Erylus formosus collected along the Caribbean coast of Mexico. Glycoside 1 was determined as a trisaccharide, glycoside 2 as a tetrasaccharide while glycosides 3-8 were hexasaccharide. Their carbohydrate chains were unprecedented and have never been found in oligosaccharides from other biological sources, except Erylus spp. Three carbohydrate chains in the glycosides 3 and 6, 4 and 7, 5 and 8 correspondingly are new. The glycosides 1-5 have penasterol as aglycone while glycosides 6-8 proved to be glycoconjugates of 24-methylene-14-carboxy-lanost-8(9)-en-3β-ol., (Copyright © 2011 Elsevier Ltd. All rights reserved.)
- Published
- 2011
- Full Text
- View/download PDF
27. Monanchocidins B-E: polycyclic guanidine alkaloids with potent antileukemic activities from the sponge Monanchora pulchra.
- Author
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Makarieva TN, Tabakmaher KM, Guzii AG, Denisenko VA, Dmitrenok PS, Shubina LK, Kuzmich AS, Lee HS, and Stonik VA
- Subjects
- Alkaloids chemistry, Animals, Antineoplastic Agents chemistry, Drug Screening Assays, Antitumor, Guanidines chemistry, HL-60 Cells, Humans, Inhibitory Concentration 50, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Alkaloids isolation & purification, Alkaloids pharmacology, Antineoplastic Agents isolation & purification, Antineoplastic Agents pharmacology, Guanidines isolation & purification, Guanidines pharmacology, Porifera chemistry
- Abstract
New unusual polycyclic guanidine alkaloids monanchocidins B-E (2-5) along with monanchocidin A (1), which we recently described, were isolated from the Far-Eastern marine sponge Monanchora pulchra. Their structures were established using spectroscopic data and chemical transformations. Compounds 1-5 show potent cytotoxic activities against HL-60 human leukemia cells with IC50 values of 540, 200, 110, 830, and 650 nM, respectively.
- Published
- 2011
- Full Text
- View/download PDF
28. Three new aaptamines from the marine sponge Aaptos sp. and their proapoptotic properties.
- Author
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Shubina LK, Makarieva TN, Dyshlovoy SA, Fedorov SN, Dmitrenok PS, and Stonik VA
- Subjects
- Alkaloids pharmacology, Animals, Cell Line, Humans, Magnetic Resonance Spectroscopy, Naphthyridines chemistry, Naphthyridines pharmacology, Alkaloids isolation & purification, Apoptosis drug effects, Naphthyridines isolation & purification, Porifera chemistry
- Abstract
Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6-(N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.
- Published
- 2010
29. Monanchocidin: a new apoptosis-inducing polycyclic guanidine alkaloid from the marine sponge Monanchora pulchra.
- Author
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Guzii AG, Makarieva TN, Denisenko VA, Dmitrenok PS, Kuzmich AS, Dyshlovoy SA, Krasokhin VB, and Stonik VA
- Subjects
- Animals, Cell Line, Guanidine chemistry, Guanidine pharmacology, Humans, Mice, Molecular Structure, Oxidation-Reduction, Apoptosis drug effects, Guanidine analogs & derivatives, Porifera chemistry
- Abstract
Monanchocidin (1), a guanidine alkaloid with an unprecedented skeleton system derived from a polyketide precursor, (ω-3)-hydroxy fatty acid, and containing a 2-aminoethyl- and 3-aminopropyl-substituted morpholine hemiketal ring, has been isolated from the sponge Monanhora pulchra. The structure of 1 was assigned on the basis of detailed analysis of 1D and 2D NMR spectra, mass spectrometry, and results of chemical transformations. Compound 1 shows pro-apoptotic and cytoxic activities.
- Published
- 2010
- Full Text
- View/download PDF
30. Dibromotyrosine and histamine derivatives from the tropical marine sponge Aplysina sp.
- Author
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Santalova EA, Denisenko VA, and Stonik VA
- Subjects
- Animals, Carbamates isolation & purification, Chromatography, Thin Layer, Histamine isolation & purification, Imidazoles isolation & purification, Indicators and Reagents, Magnetic Resonance Spectroscopy, Mass Spectrometry, Pyrimidinones isolation & purification, Spectrometry, Mass, Electrospray Ionization, Spectrophotometry, Infrared, Tyrosine isolation & purification, Carbamates chemistry, Histamine analogs & derivatives, Histamine chemistry, Imidazoles chemistry, Porifera chemistry, Pyrimidinones chemistry, Tyrosine analogs & derivatives, Tyrosine chemistry
- Abstract
Two new compounds, 3-amino-7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one (1) and ethyl 3-(2-amino-1H-imidazol-4-yl)propylcarbamate (2), along with the previously known 7,8-dihydroimidazo-[1,5-c]-pyrimidin-5(6H)-one (3), aeroplysinin-1 (4), dibromoverongiaquinol (5), bisoxazolidinone derivative (6), aerophobins-1 (7) and -2 (8), purealidins J (9) and L, have been isolated from Aplysina sp. from the South China Sea. The structures were elucidated on the basis of 1H, 13C NMR, MS and IR analyses. The histamine-derived alkaloids 1-3 may be unknown bioconversion products of purealidin J (9), aerophobin-2 (8) and aerophobin-1 (7), respectively, when 7-9 are cleaved at C-8-C-9 in reactions of activated chemical defense in Aplysina sponge.
- Published
- 2010
31. Isorhizochalin: a minor unprecedented bipolar sphingolipid of stereodivergent biogenesis from the Rhizochalina incrustata.
- Author
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Makarieva TN, Zakharenko AM, Dmitrenok PS, Guzii AG, Denisenko VA, Savina AS, Dalisay DS, Molinski TF, and Stonik VA
- Subjects
- Animals, Antineoplastic Agents isolation & purification, Antineoplastic Agents pharmacology, Cell Line, Tumor, Cell Proliferation drug effects, Circular Dichroism, Fatty Alcohols isolation & purification, Galactosides isolation & purification, Galactosides pharmacology, HL-60 Cells, Humans, Inhibitory Concentration 50, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Sphingolipids pharmacology, Stereoisomerism, Antineoplastic Agents chemistry, Fatty Alcohols chemistry, Fatty Alcohols pharmacology, Galactosides chemistry, Porifera chemistry, Sphingolipids chemistry
- Abstract
Isorhizochalin (1) was isolated as its peracetate from the EtOH extract of the sponge Rhizochalina incrustata. Its structure and absolute stereochemistry were elucidated as (2S,3R,26R,27R)-2,27-diamino-3-O-beta-D: -galactopyranosyl-oxy-26-hydroxyoctacosan-18-one by extensive NMR, MS studies, chemical transformations, including micromolar-scale Baeyer-Villiger oxidation, and by analysis of CD spectra of isorhizochalinin perbenzoate (2b). Isorhizochalin is an unprecedented C-2 epimer of rhizochalin having an erythro configuration at the glycosylated 2-amino-3-alkanol alpha-terminus in contrast with a canonical threo configuration for other representatives of this structural group. Probable biogenesis of 1 is discussed in the context of known sphingolipid biosynthesis beginning with condensation of alanine with a fatty acyl CoA thioester. The aglycone, isorhizochalinin (2a), shows cytotoxicity against human leukemia HL-60 and THP-1 cells with IC(50) values of 2.90 and 2.20 microM, respectively.
- Published
- 2009
- Full Text
- View/download PDF
32. Marine two-headed sphingolipid-like compound rhizochalin inhibits EGF-induced transformation of JB6 P+ Cl41 cells.
- Author
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Fedorov SN, Makarieva TN, Guzii AG, Shubina LK, Kwak JY, and Stonik VA
- Subjects
- Animals, Anticarcinogenic Agents isolation & purification, Cell Line, Tumor, Fatty Alcohols isolation & purification, Glycosides isolation & purification, Humans, Leukemia drug therapy, Mice, Tumor Suppressor Protein p53 metabolism, Anticarcinogenic Agents pharmacology, Apoptosis drug effects, Cell Transformation, Neoplastic drug effects, Fatty Alcohols pharmacology, Glycosides pharmacology, Porifera chemistry
- Abstract
Rhizochalin [(2R,3R,26R,27R)-2,27-diamino-3-hydroxy-26-[(2R,3R,4S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy]octacosan-11-one], an antimicrobial and cytotoxic marine two-headed sphingolipid-like natural product, isolated from the sponge Rhizochalina incrustata, and some related compounds were studied as anticarcinogenic and proapoptotic agents. The corresponding effects were tested on the mouse skin epidermal JB6 P(+) Cl 41 cell line, its stable transfectants, THP-1, HeLa, and SNU-C4 human tumor cells using a variety of assessments, including cell viability (MTS), flow cytometry, anchorage-independent soft agar, and luciferase assays. At 5-10 muM concentrations, rhizochalin was effective as an inhibitor of the malignant transformation of JB6 P(+) Cl 41 cells or colony formation of human tumor cells, which exerted its action, at least in part, through the induction of p53-dependent apoptosis. Structure-activity relationship study showed aglycon of rhizochalin to be the most active while peracetylated aglycon was the least active among the compounds studied.
- Published
- 2009
- Full Text
- View/download PDF
33. Aaptamine alkaloids from the Vietnamese sponge Aaptos sp.
- Author
-
Shubina LK, Kalinovsky AI, Fedorov SN, Radchenko OS, Denisenko VA, Dmitrenok PS, Dyshlovoy SA, Krasokhin VB, and Stonik VA
- Subjects
- Alkaloids chemistry, Animals, Magnetic Resonance Spectroscopy, Mass Spectrometry, Models, Molecular, Naphthyridines chemistry, Seawater, Vietnam, Alkaloids isolation & purification, Naphthyridines isolation & purification, Porifera chemistry
- Abstract
A series of aaptamines, including one new alkaloid (1), were isolated from the marine sponge Aaptos sp. collected in Vietnamese waters. The structure of 1 was elucidated using NMR and HRESIMS, as well as by chemical transformation of 1 to the previously known aaptamine and established as 3-N-morpholinyl-9-demethyl(oxy)aaptamine. The isolated compounds showed a potential cancer preventive activity.
- Published
- 2009
34. Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in alpha,omega-bifunctionalized ketosphingolipids.
- Author
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Makarieva TN, Dmitrenok PS, Zakharenko AM, Denisenko VA, Guzii AG, Li R, Skepper CK, Molinski TF, and Stonik VA
- Subjects
- Animals, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Glycolipids chemistry, Glycosphingolipids chemistry, Glycosphingolipids isolation & purification, Porifera chemistry
- Abstract
Rhizochalins C and D ( 1, 2), new representatives of two-headed glycosphingolipids, were isolated from the sponge Rhizochalina incrustata. Rhizochalin D is an unexpected C 29 homologue of the canonical C 28 dimeric sphingolipid structures. Their structures including absolute configurations were established using spectroscopic data, micromolar-scale Baeyer-Villiger oxidation, and LCMS interpretation of the products. Application of the latter method leads to a revision of the structure of oceanapiside and placement of the keto group at C-18 rather than C-11.
- Published
- 2007
- Full Text
- View/download PDF
35. Spongian diterpenoids from the sponge Spongia (Heterofibria) sp.
- Author
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Ponomarenko LP, Kalinovsky AI, Afiyatullov SSh, Pushilin MA, Gerasimenko AV, Krasokhin VB, and Stonik VA
- Subjects
- Animals, Crystallography, X-Ray, Molecular Conformation, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Diterpenes chemistry, Diterpenes isolation & purification, Porifera chemistry
- Abstract
Five new (1, 2, 4-6) and one known (3) diterpenoid were isolated from the keratose sponge Spongia (Heterofibria) sp. Structures of these compounds and their absolute configurations were proposed on the basis of X-ray analysis of 1, its CD spectrum, and NMR and MS spectroscopic studies of 1-6. One of the new diterpenoids was shown to be 2(R),3(S),4(S)-3,18-methylene-2-acetoxyspongia-13(16),14-diene (6), possessing a novel carbon skeleton system.
- Published
- 2007
- Full Text
- View/download PDF
36. Isolation and structures of erylosides from the Caribbean sponge Erylus formosus.
- Author
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Antonov AS, Kalinovsky AI, Stonik VA, Afiyatullov SS, Aminin DL, Dmitrenok PS, Mollo E, and Cimino G
- Subjects
- Animals, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Apoptosis drug effects, Carcinoma, Ehrlich Tumor metabolism, Caribbean Region, Drug Screening Assays, Antitumor, Glycosides chemistry, Glycosides pharmacology, Mice, Molecular Structure, Saponins chemistry, Saponins pharmacology, Spleen cytology, Spleen drug effects, Triterpenes pharmacology, Antineoplastic Agents isolation & purification, Glycosides isolation & purification, Porifera chemistry, Saponins isolation & purification, Triterpenes chemistry, Triterpenes isolation & purification
- Abstract
Nine new triterpene glycosides, erylosides F1-F4 (1-4), M (5), N (6), O (7), P (8), and Q (9), along with previously known erylosides F (10) and H (11) were isolated from the sponge Erylus formosus collected from the Mexican Gulf (Puerto Morelos, Mexico). Structures of 1-4 were determined as the corresponding biosides having aglycons related to penasterol with additional oxidation patterns in their side chains. Erylosides 5-9 contain new variants of carbohydrate chains with three (5, 6), four (7), and six (8, 9) sugar units, respectively. Erylosides 5, 7, 8, and 6, 9 contain 14-carboxy-24-methylenelanost-8(9)-en-3beta-ol and penasterol as aglycons, respectively. In contrast with its epimer 2, the compound 3 induced the early apoptosis of Ehrlich carcinoma cells at a concentration of 100 microg/mL, while 1 and 10 activated the Ca2+ influx into mouse spleenocytes (130% of the control) at the same doses.
- Published
- 2007
- Full Text
- View/download PDF
37. 5alpha-Ergost-24(28)-ene-3,6-dione - new steroid from the Pacific sponge Geodinella robusta.
- Author
-
Shubina LK, Makarieva TN, Denisenko VA, Dmitrenok AS, Guzii AG, Dmitrenok PS, and Stonik VA
- Subjects
- Animals, Circular Dichroism, Ergosterol chemistry, Ergosterol isolation & purification, Mass Spectrometry, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Optical Rotation, Spectroscopy, Fourier Transform Infrared, Ergosterol analogs & derivatives, Porifera chemistry
- Abstract
A new diketosteroid, 5alpha-ergost-24(28)-ene-3,6-dione (1), has been isolated from the sponge Geodinella robusta. Its structure was determined by combined spectroscopic methods and chemical evidence.
- Published
- 2006
- Full Text
- View/download PDF
38. Oceanalin A, a hybrid alpha,omega-bifunctionalized sphingoid tetrahydroisoquinoline beta-glycoside from the marine sponge Oceanapia sp.
- Author
-
Makarieva TN, Denisenko VA, Dmitrenok PS, Guzii AG, Santalova EA, Stonik VA, Macmillan JB, and Molinski TF
- Subjects
- Animals, Antifungal Agents chemistry, Antifungal Agents pharmacology, Candida glabrata drug effects, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Antifungal Agents isolation & purification, Glycosides isolation & purification, Porifera chemistry, Tetrahydroisoquinolines isolation & purification
- Abstract
[reaction: see text] The novel antifungal compound oceanalin A, an unprecedented "hybrid sphingolipid", was isolated from the marine sponge Oceanapia sp. The structure was elucidated using NMR and MS spectral analysis and chemical degradation. Oceanalin A exhibits in vitro antifungal activity against Candida glabrata with an MIC of 30 mug/mL.
- Published
- 2005
- Full Text
- View/download PDF
39. Rhizochalin A, a novel two-headed sphingolipid from the sponge Rhizochalina incrustata.
- Author
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Makarieva TN, Guzii AG, Denisenko VA, Dmitrenok PS, Santalova EA, Pokanevich EV, Molinski TF, and Stonik VA
- Subjects
- Animals, Anti-Bacterial Agents chemistry, Anti-Bacterial Agents pharmacology, Antifungal Agents chemistry, Antifungal Agents pharmacology, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Candida glabrata drug effects, Glycolipids chemistry, Glycolipids pharmacology, Glycosphingolipids chemistry, Glycosphingolipids pharmacology, Mice, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Russia, Staphylococcus aureus drug effects, Anti-Bacterial Agents isolation & purification, Antifungal Agents isolation & purification, Antineoplastic Agents isolation & purification, Glycosphingolipids isolation & purification, Porifera chemistry
- Abstract
Rhizochalin A (4), the fourth representative of two-headed glycosphingolipids, was isolated as its peracetate from the sponge Rhizochalina incrustata. Its structure has been established as the 2-ethyl carbamoate of rhizochalin on the basis of spectroscopic data and chemical transformations.
- Published
- 2005
- Full Text
- View/download PDF
40. New scalarane-based sesterterpenes from the sponge Phyllospongia madagascarensis.
- Author
-
Ponomarenko LP, Kalinovsky AI, and Stonik VA
- Subjects
- Animals, Madagascar, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Sesterterpenes, Structure-Activity Relationship, Porifera chemistry, Terpenes chemistry, Terpenes isolation & purification
- Abstract
Two new natural scalaranes, 16beta-acetoxy-20,24-dimethyl-12,24-dioxo-25-norscalarane and 12beta-hydroxy-20,24-dimethyl-13,18-oxa-25-norscalarane, were isolated from the Madagascaran sponge Phyllospongiamadagascarensis, together with three previously decribed tetracyclic sesterterpenoids, phyllofolactones F, G, and B, and a new artifactual ethyl ether of scalaradisin B. Structure determinations were based on NMR and other spectral data. Compounds 1 and 2 represent new examples of 20,24-dimethyl-25-norscalarane sesterterpenes, and compound 2 has a seven-membered oxacycle that makes its skeletal system unique.
- Published
- 2004
- Full Text
- View/download PDF
41. Mycalosides B-I, eight new spermostatic steroid oligoglycosides from the sponge Mycale laxissima.
- Author
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Antonov AS, Afiyatullov SSh, Kalinovsky AI, Ponomarenko LP, Dmitrenok PS, Aminin DL, Agafonova IG, and Stonik VA
- Subjects
- Animals, Cuba, Glycosides chemistry, Glycosides pharmacology, Male, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Sea Urchins drug effects, Spermatozoa drug effects, Stereoisomerism, Steroids chemistry, Steroids pharmacology, Fertilization drug effects, Glycosides isolation & purification, Porifera chemistry, Steroids isolation & purification
- Abstract
New steroidal oligoglycosides mycalosides B-I (2-9) have been isolated from the polar extract of the Caribbean sponge Mycale laxissima, and their structures have been elucidated by 1D and 2D NMR ((1)H, (13)C, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra) and MALDI-TOF mass spectrometry. Mycalosides B (2) and C (3) were shown to be 27- and 28-nor derivatives of the previously known tetraoside mycaloside A (1). Mycaloside D (4) differs from 1 only in the presence of an additional acetyl group in the carbohydrate moiety. Mycaloside E (5) was structurally identified as a 28-nor-4-dehydroxy derivative of 1. Mycalosides F-H (6-8), differing from each other by the structures of their side chains and nonacetylated (7, 8) or acetylated (6) tetrasaccharide carbohydrate moieties, have new 5(6)-unsaturated 3 beta,4 beta,21-trihydroxy-15-keto-steroidal aglycons. Mycaloside I (9) is a tetraoside of a new 7,24(28)-diunsaturated 3beta,15 beta,29-trihydroxystigmastane aglycon. It was established that the total fraction of the mycalosides as well as mycalosides A (1) and G (7) inhibit the fertilization of eggs by sperm of the sea urchin Strongylocentrotus nudus preincubated with these compounds.
- Published
- 2003
- Full Text
- View/download PDF
42. A new cytotoxic fatty acid (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid and the sterols from the far eastern sponge Geodinella robusta.
- Author
-
Makarieva TN, Santalova EA, Gorshkova IA, Dmitrenok AS, Guzii AG, Gorbach VI, Svetashev VI, and Stonik VA
- Subjects
- Animals, Carcinoma, Ehrlich Tumor drug therapy, Chromatography, High Pressure Liquid, Erythrocytes drug effects, Gas Chromatography-Mass Spectrometry, Hemolysis drug effects, In Vitro Techniques, Magnetic Resonance Spectroscopy, Mice, Cytotoxins isolation & purification, Cytotoxins pharmacology, Fatty Acids, Unsaturated isolation & purification, Fatty Acids, Unsaturated pharmacology, Porifera chemistry, Sterols chemistry
- Abstract
A new fatty acid, (5Z,9Z)-22-methyl-5,9-tetracosadienoic acid (1a), and a rare fatty acid, (5Z,9Z)-23-methyl-5,9-tetracosadienoic acid (2a), the predominant constituents of the free fatty acid fraction from the lipids of the sponge Geodinella robusta, were isolated and partly separated by reversed phase high-performance liquid chromatography, followed by multifold crystallization from MeOH to give 1a and 2a in 70% and 60% purity, respectively. These fatty acids were identified as (5Z,9Z)-22- and (5Z,9Z)-23-methyl-5,9-tetracosadienoic acids by nuclear magnetic resonance techniques, including distortionless enhancement by polarization transfer, heteronuclear multiple quantum connectivity, and correlation spectroscopy experiments, as well as from mass-spectrometric data for their methyl esters, the methyl esters of their perhydro derivatives, and their pyrrolidides. Mixtures of 1a and 2a showed cytotoxic activity against mouse Ehrlich carcinoma cells and a hemolytic effect on mouse erythrocytes. The sterol fraction from the same sponge was analyzed by gas-liquid chromatography-mass spectrometry, and 24-methylenecholesterol was identified as a main constituent of this fraction. The implications of the co-occurrence of membranolytic long-chain fatty acids and 24-methylenecholesterol as a main membrane sterol are discussed in terms of the phenomenon of biochemical coordination.
- Published
- 2002
- Full Text
- View/download PDF
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