The Experts below are selected from a list of 1179 Experts worldwide ranked by ideXlab platform
Vladimir I Kalinin - One of the best experts on this subject based on the ideXlab platform.
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progress in the studies of Triterpene Glycosides from sea cucumbers holothuroidea echinodermata between 2017 and 2021
Natural Product Communications, 2021Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Structural diversity of Triterpene Glycosides produced by sea cucumbers or holothurians (Holothuroidea, Echinodermata) is extremely high, although all of them are either lanostane derivatives or, r...
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Non-holostane aglycones of sea cucumber Triterpene Glycosides. Structure, biosynthesis, evolution.
Steroids, 2018Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Abstract Triterpene Glycosides are known as characteristic metabolites of sea cucumbers (class Holothuroidea, phylum Echinodermata). The most of them have lanostane aglycones containing 18(20)-lactone, i.e. belongs to so-called holostane series. However non-holostane Glycosides having no lactone (with the both normal and shortened side chains) or containing 18(16)-lactone function were also found in these invertebrates last a few decades. In addition, some very rare findings of the Glycosides containing rearranged lanostane skeleton systems were reported. Probably, these natural products are formed in result of intramolecular aldol condensation of 1,6-diketo precursors as well as by Meinwald rearrangement of 1,2-epoxy precursor or pinacol-pinacolone rearrangement of fully substituted 1,2-diol precursor. Structures, biosynthesis and evolution of non-holostane aglycones of sea cucumber Triterpene Glycosides are discussed. Biological properties of the Glycosides with hon-holostane aglycones are also discussed.
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metabolite profiling of Triterpene Glycosides of the far eastern sea cucumber eupentacta fraudatrix and their distribution in various body components using lc esi qtof ms
Marine Drugs, 2017Co-Authors: Roman S Popov, Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Valentin A Stonik, Natalia V. Ivanchina, Igor Yu Dolmatov, Pavel S DmitrenokAbstract:The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of Triterpene Glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of Triterpene Glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of Triterpene Glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated Glycosides were detected and described. Triterpene Glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new Glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the Triterpene Glycosides contents from the five different body components revealed that the profiles of Triterpene Glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.
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fallaxosides b1 and d3 Triterpene Glycosides with novel skeleton types of aglycones from the sea cucumber cucumaria fallax
Tetrahedron, 2017Co-Authors: Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Anatoly I Kalinovsky, Pelageya V Andryjaschenko, Dmitrii V Berdyshev, Ekaterina A Chingizova, Pavel S Dmitrenok, Kirill V MininAbstract:Abstract Two unprecedented Triterpene Glycosides, fallaxosides B 1 and D 3 with aglycones of new skeletal types were isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The first of these aglycones is formed as result of intramolecular aldol condensation of a precursor having 1,6-diketone functionality, while the second one by pinacol-pinacolone-like rearrangement of another precursor, probably containing 7,8,9-trihydroxy fragment (or its 8,9-epoxy-7-hydroxy analog). The structures of these compounds were established by analysis of 1D, 2D NMR, ESI MS and CD data with using the quantum-chemical calculations.
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structures and biogenesis of fallaxosides d4 d5 d6 and d7 trisulfated non holostane Triterpene Glycosides from the sea cucumber cucumaria fallax
Molecules, 2016Co-Authors: Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Anatoly I Kalinovsky, Pelageya V Andryjaschenko, Ekaterina A Chingizova, Pavel S Dmitrenok, Kirill V MininAbstract:Four new trisulfated Triterpene Glycosides, fallaxosides D4 (1), D5 (2), D6 (3) and D7 (4) have been isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The structures of the Glycosides have been elucidated by 2D NMR spectroscopy and HRESIMS. All the Glycosides have the lanostane aglycones of a rare non-holostane type with 7(8)-, 8(9)- or 9(11)-double bonds, one or two hydroxyl groups occupying unusual positions in the polycyclic nucleus and shortened or normal side chains. The pentasaccharide carbohydrate moieties of 1–4 have three sulfate groups. The cytotoxic activity of Glycosides 1–4 against the ascite form of mouse Ehrlich carcinoma cells and mouse spleen lymphocytes and hemolytic activity against mouse erythrocytes have been studied.
Pavel S Dmitrenok - One of the best experts on this subject based on the ideXlab platform.
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new Triterpene Glycosides from the far eastern starfish solaster pacificus and their biological activity
Biomolecules, 2021Co-Authors: Valentin A Stonik, Anatoly I Kalinovsky, Pavel S Dmitrenok, Timofey V Malyarenko, Alla A Kicha, Olesya S Malyarenko, Alexandra S Kuzmich, Natalia V. IvanchinaAbstract:Three new Triterpene Glycosides, pacificusosides A-C (1-3), and three previously known Triterpene Glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1-3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. Compound 1 has a novel, unique structure, containing an aldehyde group of side chains in its Triterpene aglycon. This structural fragment has not previously been found in the sea cucumber Triterpene Glycosides or starfish steroidal Glycosides. Probably, pacificusoside A (1) is a product of the metabolism of the glycoside obtained through dietary means from a sea cucumber in the starfish. Another two new Triterpene Glycosides (2, 3) have closely related characteristics to sea cucumber Glycosides. The cytotoxicity of compounds 1-6 was tested against human embryonic kidney HEK 293 cells, colorectal carcinoma HT-29 cells, melanoma RPMI-7951 cells, and breast cancer MDA-MB-231 cells using MTS assay. Compounds 4-6 revealed the highest cytotoxic activity against the tested cell lines, while the other investigated compounds had moderate or slight cytotoxicity. The cytotoxic effects of 2-6 were reduced by cholesterol like the similar effects of the previously investigated individual Triterpene Glycosides. Compounds 3, 4, and 5 almost completely suppressed the colony formation of the HT-29, RPMI-7951, and MDA-MB-231 cells at a nontoxic concentration of 0.5 µM.
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Triterpene Glycosides from the Vietnamese sea cucumber Holothuria edulis
Natural product research, 2019Co-Authors: Le Hoang, Vien Le Thi, Hanh Tran Thi Hong, Thanh Nguyen Van, Cuong Nguyen Xuan, Nam Nguyen Hoai, Thung Do Cong, Natalia V. Ivanchina, Thao Do Thi, Pavel S DmitrenokAbstract:From the MeOH extract of the Vietnamese sea cucumber Holothuria edulis, eight Triterpene Glycosides (1–8), including one new compound namely holothurin A5 (1), were isolated by using various chroma...
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Triterpene Glycosides from the Vietnamese sea cucumber Holothuria edulis
2019Co-Authors: Le Hoang, Hanh Tran Thi Hong, Thanh Nguyen Van, Cuong Nguyen Xuan, Nam Nguyen Hoai, Thung Do Cong, Natalia V. Ivanchina, Thao Do Thi, Vien Le Thi, Pavel S DmitrenokAbstract:From the MeOH extract of the Vietnamese sea cucumber Holothuria edulis, eight Triterpene Glycosides (1–8), including one new compound namely holothurin A5 (1), were isolated by using various chromatographic separations. Their structures were established by spectroscopic experiments including 1D, 2D NMR and HR-ESI-MS. Holothurin A5 (1) has a hydroperoxy group at C-25. To the best of our knowledge, this is the first report of this group in Triterpene saponins obtained from sea cucumbers to date. In addition, the in vitro cytotoxicity against five human cancer cell lines (HepG2, KB, LNCaP, MCF7 and SK-Mel2) of all isolated compounds was also evaluated using SRB assays.
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metabolite profiling of Triterpene Glycosides of the far eastern sea cucumber eupentacta fraudatrix and their distribution in various body components using lc esi qtof ms
Marine Drugs, 2017Co-Authors: Roman S Popov, Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Valentin A Stonik, Natalia V. Ivanchina, Igor Yu Dolmatov, Pavel S DmitrenokAbstract:The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of Triterpene Glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of Triterpene Glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of Triterpene Glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated Glycosides were detected and described. Triterpene Glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new Glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the Triterpene Glycosides contents from the five different body components revealed that the profiles of Triterpene Glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.
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fallaxosides b1 and d3 Triterpene Glycosides with novel skeleton types of aglycones from the sea cucumber cucumaria fallax
Tetrahedron, 2017Co-Authors: Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Anatoly I Kalinovsky, Pelageya V Andryjaschenko, Dmitrii V Berdyshev, Ekaterina A Chingizova, Pavel S Dmitrenok, Kirill V MininAbstract:Abstract Two unprecedented Triterpene Glycosides, fallaxosides B 1 and D 3 with aglycones of new skeletal types were isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The first of these aglycones is formed as result of intramolecular aldol condensation of a precursor having 1,6-diketone functionality, while the second one by pinacol-pinacolone-like rearrangement of another precursor, probably containing 7,8,9-trihydroxy fragment (or its 8,9-epoxy-7-hydroxy analog). The structures of these compounds were established by analysis of 1D, 2D NMR, ESI MS and CD data with using the quantum-chemical calculations.
Alexandra S Silchenko - One of the best experts on this subject based on the ideXlab platform.
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progress in the studies of Triterpene Glycosides from sea cucumbers holothuroidea echinodermata between 2017 and 2021
Natural Product Communications, 2021Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Structural diversity of Triterpene Glycosides produced by sea cucumbers or holothurians (Holothuroidea, Echinodermata) is extremely high, although all of them are either lanostane derivatives or, r...
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Non-holostane aglycones of sea cucumber Triterpene Glycosides. Structure, biosynthesis, evolution.
Steroids, 2018Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Abstract Triterpene Glycosides are known as characteristic metabolites of sea cucumbers (class Holothuroidea, phylum Echinodermata). The most of them have lanostane aglycones containing 18(20)-lactone, i.e. belongs to so-called holostane series. However non-holostane Glycosides having no lactone (with the both normal and shortened side chains) or containing 18(16)-lactone function were also found in these invertebrates last a few decades. In addition, some very rare findings of the Glycosides containing rearranged lanostane skeleton systems were reported. Probably, these natural products are formed in result of intramolecular aldol condensation of 1,6-diketo precursors as well as by Meinwald rearrangement of 1,2-epoxy precursor or pinacol-pinacolone rearrangement of fully substituted 1,2-diol precursor. Structures, biosynthesis and evolution of non-holostane aglycones of sea cucumber Triterpene Glycosides are discussed. Biological properties of the Glycosides with hon-holostane aglycones are also discussed.
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metabolite profiling of Triterpene Glycosides of the far eastern sea cucumber eupentacta fraudatrix and their distribution in various body components using lc esi qtof ms
Marine Drugs, 2017Co-Authors: Roman S Popov, Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Valentin A Stonik, Natalia V. Ivanchina, Igor Yu Dolmatov, Pavel S DmitrenokAbstract:The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of Triterpene Glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of Triterpene Glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of Triterpene Glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated Glycosides were detected and described. Triterpene Glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new Glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the Triterpene Glycosides contents from the five different body components revealed that the profiles of Triterpene Glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.
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fallaxosides b1 and d3 Triterpene Glycosides with novel skeleton types of aglycones from the sea cucumber cucumaria fallax
Tetrahedron, 2017Co-Authors: Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Anatoly I Kalinovsky, Pelageya V Andryjaschenko, Dmitrii V Berdyshev, Ekaterina A Chingizova, Pavel S Dmitrenok, Kirill V MininAbstract:Abstract Two unprecedented Triterpene Glycosides, fallaxosides B 1 and D 3 with aglycones of new skeletal types were isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The first of these aglycones is formed as result of intramolecular aldol condensation of a precursor having 1,6-diketone functionality, while the second one by pinacol-pinacolone-like rearrangement of another precursor, probably containing 7,8,9-trihydroxy fragment (or its 8,9-epoxy-7-hydroxy analog). The structures of these compounds were established by analysis of 1D, 2D NMR, ESI MS and CD data with using the quantum-chemical calculations.
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in vitro anticancer activities of some Triterpene Glycosides from holothurians of cucumariidae stichopodidae psolidae holothuriidae and synaptidae families
Natural Product Communications, 2016Co-Authors: Sergey N Fedorov, Alexandra S Silchenko, Sergey A Avilov, Alexandra S Kuzmich, Sergey A Dyshlovoy, Larisa K Shubina, Ann M Bode, Zigang Dong, Valentin A StonikAbstract:Triterpene Glycosides isolated from holothurians are natural products known to possess cytotoxic properties against cancer cells. However, their anticancer prophylactic activity has not been studied sufficiently. The anticancer prophylactic; cytotoxic, and pro-apoptotic properties of 18 Triterpene Glycosides, as well as their effects on the transcriptional activities of activator protein-I (AP-1) and nuclear factor-KB (NF-KB), were examined using methods that included EGF-induced JB6 C141 P' cell transformation in soft agar, flow cytometry, MTS assessment of cell viability, and a luciferase activity assay. The compounds inhibited EGF-induced neoplastic JB6 C141 P' cell transformation in soft agar and caused apoptosis and necrosis of human HL-60 and THP-I leukemia cells. AP- and NF-KB were involved in the cellular response to the treatment by the compounds. Conclusion: Glycosides isolated from holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families have potential for development as new antitumor agents and as instruments to study AP-I and NF-kB.
Sergey A Avilov - One of the best experts on this subject based on the ideXlab platform.
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progress in the studies of Triterpene Glycosides from sea cucumbers holothuroidea echinodermata between 2017 and 2021
Natural Product Communications, 2021Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Structural diversity of Triterpene Glycosides produced by sea cucumbers or holothurians (Holothuroidea, Echinodermata) is extremely high, although all of them are either lanostane derivatives or, r...
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Non-holostane aglycones of sea cucumber Triterpene Glycosides. Structure, biosynthesis, evolution.
Steroids, 2018Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Abstract Triterpene Glycosides are known as characteristic metabolites of sea cucumbers (class Holothuroidea, phylum Echinodermata). The most of them have lanostane aglycones containing 18(20)-lactone, i.e. belongs to so-called holostane series. However non-holostane Glycosides having no lactone (with the both normal and shortened side chains) or containing 18(16)-lactone function were also found in these invertebrates last a few decades. In addition, some very rare findings of the Glycosides containing rearranged lanostane skeleton systems were reported. Probably, these natural products are formed in result of intramolecular aldol condensation of 1,6-diketo precursors as well as by Meinwald rearrangement of 1,2-epoxy precursor or pinacol-pinacolone rearrangement of fully substituted 1,2-diol precursor. Structures, biosynthesis and evolution of non-holostane aglycones of sea cucumber Triterpene Glycosides are discussed. Biological properties of the Glycosides with hon-holostane aglycones are also discussed.
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metabolite profiling of Triterpene Glycosides of the far eastern sea cucumber eupentacta fraudatrix and their distribution in various body components using lc esi qtof ms
Marine Drugs, 2017Co-Authors: Roman S Popov, Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Valentin A Stonik, Natalia V. Ivanchina, Igor Yu Dolmatov, Pavel S DmitrenokAbstract:The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of Triterpene Glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of Triterpene Glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of Triterpene Glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated Glycosides were detected and described. Triterpene Glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new Glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the Triterpene Glycosides contents from the five different body components revealed that the profiles of Triterpene Glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.
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fallaxosides b1 and d3 Triterpene Glycosides with novel skeleton types of aglycones from the sea cucumber cucumaria fallax
Tetrahedron, 2017Co-Authors: Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Anatoly I Kalinovsky, Pelageya V Andryjaschenko, Dmitrii V Berdyshev, Ekaterina A Chingizova, Pavel S Dmitrenok, Kirill V MininAbstract:Abstract Two unprecedented Triterpene Glycosides, fallaxosides B 1 and D 3 with aglycones of new skeletal types were isolated from the sea cucumber Cucumaria fallax (Cucumariidae, Dendrochirotida). The first of these aglycones is formed as result of intramolecular aldol condensation of a precursor having 1,6-diketone functionality, while the second one by pinacol-pinacolone-like rearrangement of another precursor, probably containing 7,8,9-trihydroxy fragment (or its 8,9-epoxy-7-hydroxy analog). The structures of these compounds were established by analysis of 1D, 2D NMR, ESI MS and CD data with using the quantum-chemical calculations.
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in vitro anticancer activities of some Triterpene Glycosides from holothurians of cucumariidae stichopodidae psolidae holothuriidae and synaptidae families
Natural Product Communications, 2016Co-Authors: Sergey N Fedorov, Alexandra S Silchenko, Sergey A Avilov, Alexandra S Kuzmich, Sergey A Dyshlovoy, Larisa K Shubina, Ann M Bode, Zigang Dong, Valentin A StonikAbstract:Triterpene Glycosides isolated from holothurians are natural products known to possess cytotoxic properties against cancer cells. However, their anticancer prophylactic activity has not been studied sufficiently. The anticancer prophylactic; cytotoxic, and pro-apoptotic properties of 18 Triterpene Glycosides, as well as their effects on the transcriptional activities of activator protein-I (AP-1) and nuclear factor-KB (NF-KB), were examined using methods that included EGF-induced JB6 C141 P' cell transformation in soft agar, flow cytometry, MTS assessment of cell viability, and a luciferase activity assay. The compounds inhibited EGF-induced neoplastic JB6 C141 P' cell transformation in soft agar and caused apoptosis and necrosis of human HL-60 and THP-I leukemia cells. AP- and NF-KB were involved in the cellular response to the treatment by the compounds. Conclusion: Glycosides isolated from holothurians of Cucumariidae, Stichopodidae, Psolidae, Holothuriidae and Synaptidae families have potential for development as new antitumor agents and as instruments to study AP-I and NF-kB.
Valentin A Stonik - One of the best experts on this subject based on the ideXlab platform.
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progress in the studies of Triterpene Glycosides from sea cucumbers holothuroidea echinodermata between 2017 and 2021
Natural Product Communications, 2021Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Structural diversity of Triterpene Glycosides produced by sea cucumbers or holothurians (Holothuroidea, Echinodermata) is extremely high, although all of them are either lanostane derivatives or, r...
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new Triterpene Glycosides from the far eastern starfish solaster pacificus and their biological activity
Biomolecules, 2021Co-Authors: Valentin A Stonik, Anatoly I Kalinovsky, Pavel S Dmitrenok, Timofey V Malyarenko, Alla A Kicha, Olesya S Malyarenko, Alexandra S Kuzmich, Natalia V. IvanchinaAbstract:Three new Triterpene Glycosides, pacificusosides A-C (1-3), and three previously known Triterpene Glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1-3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. Compound 1 has a novel, unique structure, containing an aldehyde group of side chains in its Triterpene aglycon. This structural fragment has not previously been found in the sea cucumber Triterpene Glycosides or starfish steroidal Glycosides. Probably, pacificusoside A (1) is a product of the metabolism of the glycoside obtained through dietary means from a sea cucumber in the starfish. Another two new Triterpene Glycosides (2, 3) have closely related characteristics to sea cucumber Glycosides. The cytotoxicity of compounds 1-6 was tested against human embryonic kidney HEK 293 cells, colorectal carcinoma HT-29 cells, melanoma RPMI-7951 cells, and breast cancer MDA-MB-231 cells using MTS assay. Compounds 4-6 revealed the highest cytotoxic activity against the tested cell lines, while the other investigated compounds had moderate or slight cytotoxicity. The cytotoxic effects of 2-6 were reduced by cholesterol like the similar effects of the previously investigated individual Triterpene Glycosides. Compounds 3, 4, and 5 almost completely suppressed the colony formation of the HT-29, RPMI-7951, and MDA-MB-231 cells at a nontoxic concentration of 0.5 µM.
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Non-holostane aglycones of sea cucumber Triterpene Glycosides. Structure, biosynthesis, evolution.
Steroids, 2018Co-Authors: Vladimir I Kalinin, Alexandra S Silchenko, Sergey A Avilov, Valentin A StonikAbstract:Abstract Triterpene Glycosides are known as characteristic metabolites of sea cucumbers (class Holothuroidea, phylum Echinodermata). The most of them have lanostane aglycones containing 18(20)-lactone, i.e. belongs to so-called holostane series. However non-holostane Glycosides having no lactone (with the both normal and shortened side chains) or containing 18(16)-lactone function were also found in these invertebrates last a few decades. In addition, some very rare findings of the Glycosides containing rearranged lanostane skeleton systems were reported. Probably, these natural products are formed in result of intramolecular aldol condensation of 1,6-diketo precursors as well as by Meinwald rearrangement of 1,2-epoxy precursor or pinacol-pinacolone rearrangement of fully substituted 1,2-diol precursor. Structures, biosynthesis and evolution of non-holostane aglycones of sea cucumber Triterpene Glycosides are discussed. Biological properties of the Glycosides with hon-holostane aglycones are also discussed.
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metabolite profiling of Triterpene Glycosides of the far eastern sea cucumber eupentacta fraudatrix and their distribution in various body components using lc esi qtof ms
Marine Drugs, 2017Co-Authors: Roman S Popov, Alexandra S Silchenko, Sergey A Avilov, Vladimir I Kalinin, Valentin A Stonik, Natalia V. Ivanchina, Igor Yu Dolmatov, Pavel S DmitrenokAbstract:The Far Eastern sea cucumber Eupentacta fraudatrix is an inhabitant of shallow waters of the south part of the Sea of Japan. This animal is an interesting and rich source of Triterpene Glycosides with unique chemical structures and various biological activities. The objective of this study was to investigate composition and distribution in various body components of Triterpene Glycosides of the sea cucumber E. fraudatrix. We applied LC-ESI MS (liquid chromatography–electrospray mass spectrometry) of whole body extract and extracts of various body components for metabolic profiling and structure elucidation of Triterpene Glycosides from the E. fraudatrix. Totally, 54 compounds, including 26 sulfated, 18 non-sulfated and 10 disulfated Glycosides were detected and described. Triterpene Glycosides from the body walls, gonads, aquapharyngeal bulbs, guts and respiratory trees were extracted separately and the distributions of the detected compounds in various body components were analyzed. Series of new Glycosides with unusual structural features were described in E. fraudatrix, which allow clarifying the biosynthesis of these compounds. Comparison of the Triterpene Glycosides contents from the five different body components revealed that the profiles of Triterpene Glycosides were qualitatively similar, and only some quantitative variabilities for minor compounds were observed.
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Ceramide as a Target of Marine Triterpene Glycosides for Treatment of Human Myeloid Leukemia
Marine drugs, 2016Co-Authors: Seong Hoon Yun, Valentin A Stonik, Sung-won Shin, Joo In ParkAbstract:Acute myeloid leukemia (AML) is a heterogeneous myeloid clonal disorder exhibiting the accumulation of immature myeloid progenitors in the bone marrow and peripheral blood. Standard AML therapy requires intensive combination chemotherapy, which leads to significant treatment-related toxicity. The search for new, low toxic marine agents, inducing the generation of ceramide in leukemic cells is a new approach to improve the therapy of leukemia. This review focuses on the metabolism of sphingolipids, the role of ceramide in treating leukemia, and the antitumor activity, related to ceramide metabolism, of some marine metabolites, particularly stichoposides, Triterpene Glycosides extracted from sea cucumbers of the family Stichopodiidae.
