Skip header and navigation

Refine By

7 records – page 1 of 1.

Kolgaosides A and B, two new triterpene glycosides from the Arctic deep water sea cucumber Kolga hyalina (Elasipodida: Elpidiidae).

https://arctichealth.org/en/permalink/ahliterature262303
Source
Nat Prod Commun. 2014 Sep;9(9):1259-64
Publication Type
Article
Date
Sep-2014
Author
Alexandra S Silchenko
Anatoly I Kalinovsky
Sergey A Avilov
Pelageya V Andryjashchenko
Sergey N Fedorov
Pavel S Dmitrenok
Ekaterina A Yurchenko
Vladimir I Kalinin
Antonina V Rogacheva
Andrey V Gebruk
Source
Nat Prod Commun. 2014 Sep;9(9):1259-64
Date
Sep-2014
Language
English
Publication Type
Article
Abstract
Two novel triterpene holostane nonsulfated pentaosides, kolgaosides A (1) and B (2), and one known, holothurinoside B (3), were isolated from the Arctic sea cucumber Kolga hyalina, the second representative of the family Elpidiidae, order Elasipodida, from which triterpene glycosides have been obtained. The structures of 1 and 2 were elucidated using 1H and 13C NMR and 2D NMR procedures (HSQC, HMBC, COSY, ROESY, TOCSY) and HRESI mass-spectrometry. Kolgaosides A (1) and B (2) demonstrate low cytotoxic activity against the cells of the ascite form of mouse Ehrlich carcinoma and moderate hemolytic activity against mouse erythrocytes, despite the presence of hydroxy groups in the side chains of the aglycones. The glycosides of K. hyalina are similar to those of the Antarctic sea cucumber Rhipidothuria racowitzai H?rouard, 1901 (=Achlionice violaescupidata) (Elasipodida: Elpidiidae); this may have chemotaxonomic significance.
PubMed ID
25918787 View in PubMed
Less detail

Kurilosides A1, A2, C1, D, E and F-Triterpene Glycosides from the Far Eastern Sea Cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin): Structures with Unusual Non-Holostane Aglycones and Cytotoxicities.

https://arctichealth.org/en/permalink/ahliterature304236
Source
Mar Drugs. 2020 Nov 06; 18(11):
Publication Type
Journal Article
Date
Nov-06-2020
Author
Alexandra S Silchenko
Anatoly I Kalinovsky
Sergey A Avilov
Pelageya V Andrijaschenko
Roman S Popov
Pavel S Dmitrenok
Ekaterina A Chingizova
Vladimir I Kalinin
Author Affiliation
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia.
Source
Mar Drugs. 2020 Nov 06; 18(11):
Date
Nov-06-2020
Language
English
Publication Type
Journal Article
Abstract
Six new monosulfated triterpene tetra-, penta- and hexaosides, namely, the kurilosides A1 (1), A2 (2), C1 (3), D (4), E (5) and F (6), as well as the known earlier kuriloside A (7), having unusual non-holostane aglycones without lactone, have been isolated from the sea cucumber Thyonidium (= Duasmodactyla) kurilensis (Levin) (Cucumariidae, Dendrochirotida), collected in the Sea of Okhotsk near Onekotan Island from a depth of 100 m. Structures of the glycosides were established by 2D NMR spectroscopy and HR-ESI mass spectrometry. Kurilosides of the groups A and E contain carbohydrate moieties with a rare architecture (a pentasaccharide branched by C(4) Xyl1), differing from each other in the second monosaccharide residue (quinovose or glucose, correspondingly); kurilosides of the group C are characterized by a unique tetrasaccharide branched by a C(4) Xyl1 sugar chain; and kurilosides of the groups D and F are hexaosides differing from each other in the presence of an O-methyl group in the fourth (terminal) sugar unit. All these glycosides contain a sulfate group at C-6 of the glucose residue attached to C-4 Xyl1 and the non-holostane aglycones have a 9(11) double bond and lack ?-lactone. The cytotoxic activities of compounds 1-7 against mouse neuroblastoma Neuro 2a, normal epithelial JB-6 cells and erythrocytes were studied. Kuriloside A1 (1) was the most active compound in the series, demonstrating strong cytotoxicity against the erythrocytes and JB-6 cells and a moderate effect against Neuro 2a cells.
PubMed ID
33172125 View in PubMed
Less detail

Lissodendoric Acids A and B, Manzamine-Related Alkaloids from the Far Eastern Sponge Lissodendoryx florida.

https://arctichealth.org/en/permalink/ahliterature294829
Source
Org Lett. 2017 10 06; 19(19):5320-5323
Publication Type
Journal Article
Research Support, Non-U.S. Gov't
Date
10-06-2017
Author
Ekaterina G Lyakhova
Sophia A Kolesnikova
Anatoly I Kalinovsky
Dmitrii V Berdyshev
Evgeny A Pislyagin
Aleksandra S Kuzmich
Roman S Popov
Pavel S Dmitrenok
Tatyana N Makarieva
Valentin A Stonik
Author Affiliation
G. B. Elyakov Pacific Institute of Bioorganic Chemistry, The Far East Branch of the Russian Academy of Sciences , Prospect 100-let Vladivostoku 159, Vladivostok-22, Russia.
Source
Org Lett. 2017 10 06; 19(19):5320-5323
Date
10-06-2017
Language
English
Publication Type
Journal Article
Research Support, Non-U.S. Gov't
Keywords
Alkaloids - chemistry
Animals
Molecular Structure
Porifera
Abstract
The first representatives of a new group of manzamine-related alkaloids with a previously unknown skeletal systems, namely, lissodendoric acids A (1) and B (2), were isolated from the sponge Lissodendoryx florida collected from the Sea of Okhotsk. The structures and absolute configurations have been elucidated by extensive spectroscopic analysis together with chemical transformations and quantum-chemical modeling. The lissodendoric acids show a potent capability to decrease the production of reactive oxygen species in neuroblastoma Neuro 2a and somewhat increase the survival of these cells upon treatment with 6-hydroxydopamine (an in vitro antiparkinson biotest).
PubMed ID
28933163 View in PubMed
Less detail

Lissodendoric Acids A and B, Manzamine-Related Alkaloids from the Far Eastern Sponge Lissodendoryx florida.

https://arctichealth.org/en/permalink/ahliterature285792
Source
Org Lett. 2017 Oct 06;19(19):5320-5323
Publication Type
Article
Date
Oct-06-2017
Author
Ekaterina G Lyakhova
Sophia A Kolesnikova
Anatoly I Kalinovsky
Dmitrii V Berdyshev
Evgeny A Pislyagin
Aleksandra S Kuzmich
Roman S Popov
Pavel S Dmitrenok
Tatyana N Makarieva
Valentin A Stonik
Source
Org Lett. 2017 Oct 06;19(19):5320-5323
Date
Oct-06-2017
Language
English
Publication Type
Article
Abstract
The first representatives of a new group of manzamine-related alkaloids with a previously unknown skeletal systems, namely, lissodendoric acids A (1) and B (2), were isolated from the sponge Lissodendoryx florida collected from the Sea of Okhotsk. The structures and absolute configurations have been elucidated by extensive spectroscopic analysis together with chemical transformations and quantum-chemical modeling. The lissodendoric acids show a potent capability to decrease the production of reactive oxygen species in neuroblastoma Neuro 2a and somewhat increase the survival of these cells upon treatment with 6-hydroxydopamine (an in vitro antiparkinson biotest).
PubMed ID
28933163 View in PubMed
Less detail

Structural Analysis of the Minor Cerebrosides from a Glass Sponge Aulosaccus sp.

https://arctichealth.org/en/permalink/ahliterature276160
Source
Lipids. 2015 Dec;50(12):1209-18
Publication Type
Article
Date
Dec-2015
Author
Elena A Santalova
Vladimir A Denisenko
Pavel S Dmitrenok
Source
Lipids. 2015 Dec;50(12):1209-18
Date
Dec-2015
Language
English
Publication Type
Article
Keywords
Acylation
Animals
Cerebrosides - chemistry - isolation & purification
Chromatography, High Pressure Liquid
Chromatography, Reverse-Phase
Complex Mixtures - chemistry - isolation & purification
Ethanol - chemistry
Lipoylation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Optical Rotation
Pacific Islands
Pacific Ocean
Porifera - chemistry - growth & development
Russia
Solvents - chemistry
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
Tandem Mass Spectrometry
Abstract
The minor cerebrosides from a Far-Eastern glass sponge Aulosaccus sp. were analyzed as constituents of some multi-component RP-HPLC fractions. The structures of eighteen new and one known cerebrosides were elucidated on the basis of NMR spectroscopy, mass spectrometry, optical rotation data and chemical transformations. These ß-D-glucopyranosyl-(1?1)-ceramides contain sphingoid bases N-acylated with straight-chain (2R)-2-hydroxy fatty acids, namely, (2S,3S,4R,11Z)-2-aminoeicos-11-ene-1,3,4-triol, acylated with 15E-22:1, 16Z-21:1, 15Z-21:1, 15Z-20:1, 15E-20:1, 19:0, 18:0 acids, (2S,3S,4R)-2-amino-13-methyltetradecane-1,3,4-triol--with 19Z-26:1, 16Z-23:1, 23:0, 22:0 acids, (2S,3S,4R)-2-amino-14-methylpentadecane-1,3,4-triol--with 16Z-23:1, 16E-23:1, 15Z-22:1, 22:0 acids, (2S,3S,4R)-2-amino-14-methylhexadecane-1,3,4-triol, linked to 16Z-23:1, 15Z-22:1 acids, (2S,3S,4R)-2-amino-9-methylhexadecane-1,3,4-triol--to 16Z-23:1 acid, and (2S,3S,4R)-2-aminohexadecane-1,3,4-triol, attached to 15Z-22:1 acid. The 13-methyl and 9-methyl-branched trihydroxy sphingoid base backbones (C15 and C17, respectively) have not been found previously in sphingolipids. The ceramide parts, containing other backbones, present new variants of N-acylation of the marine sphingoid bases with the 2-hydroxy fatty acids. The combination of the instrumental and chemical methods used in this study improved the efficiency of the structural analysis of such complex cerebroside mixtures that gave more detailed information on glycosphingolipid metabolism of the organism.
PubMed ID
26475294 View in PubMed
Less detail

Structures and Bioactivities of Psolusosides B1, B2, J, K, L, M, N, O, P, and Q from the Sea Cucumber Psolus fabricii. The First Finding of Tetrasulfated Marine Low Molecular Weight Metabolites.

https://arctichealth.org/en/permalink/ahliterature308283
Source
Mar Drugs. 2019 Nov 06; 17(11):
Publication Type
Journal Article
Date
Nov-06-2019
Author
Alexandra S Silchenko
Anatoly I Kalinovsky
Sergey A Avilov
Vladimir I Kalinin
Pelageya V Andrijaschenko
Pavel S Dmitrenok
Roman S Popov
Ekaterina A Chingizova
Author Affiliation
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, 690022 Vladivostok, Russia.
Source
Mar Drugs. 2019 Nov 06; 17(11):
Date
Nov-06-2019
Language
English
Publication Type
Journal Article
Keywords
Animals
Antineoplastic Agents - chemistry - isolation & purification - pharmacology
Cell Line, Tumor
Glycosides - chemistry - isolation & purification - pharmacology
Magnetic Resonance Spectroscopy
Mice
Molecular Weight
Neoplasms - drug therapy - pathology
Sea Cucumbers - chemistry
Spectrometry, Mass, Electrospray Ionization
Structure-Activity Relationship
Triterpenes - chemistry - isolation & purification - pharmacology
Abstract
Ten new di-, tri- and tetrasulfated triterpene glycosides, psolusosides B1 (1), B2 (2), J (3), K (4), L (5), M (6), N (7), O (8), P (9), and Q (10), were isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk near the Kurile Islands. Structures of these glycosides were established by two-dimensional (2D) NMR spectroscopy and HR-ESI mass-spectrometry. It is particularly interesting that highly polar compounds 9 and 10 contain four sulfate groups in their carbohydrate moieties, including two sulfates in the same terminal glucose residue. Glycoside 2 has an unusual non-holostane aglycone with 18(16)-lactone and a unique 7,8-epoxy fragment. Cytotoxic activities of compounds 1-10 against several mouse cell lines such as Ehrlich ascites carcinoma cells, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes were quite different depending both on structural peculiarities of these glycosides and the type of cells subjected to their actions. Psolusoside L (5), pentaoside, with three sulfate groups at C-6 of two glucose and one 3-O-methylglucose residue and holostane aglycone, is the most active compound in the series. The presence of a sulfate group at C-2 of the terminal glucose residue attached to C-4 of the first (xylose) residue significantly decreases activities of the corresponding glycosides. Psolusosides of group B (1, 2, and known psolusoside B) are inactive in all tests due to the presence of non-holostane aglycones and tetrasaccharide-branched sugar chains sulfated by C-2 of Glc4.
PubMed ID
31698820 View in PubMed
Less detail

Structures and Bioactivities of Six New Triterpene Glycosides, Psolusosides E, F, G, H, H1, and I and the Corrected Structure of Psolusoside B from the Sea Cucumber Psolus fabricii.

https://arctichealth.org/en/permalink/ahliterature301087
Source
Mar Drugs. 2019 Jun 14; 17(6):
Publication Type
Journal Article
Date
Jun-14-2019
Author
Alexandra S Silchenko
Anatoly I Kalinovsky
Sergey A Avilov
Vladimir I Kalinin
Pelageya V Andrijaschenko
Pavel S Dmitrenok
Roman S Popov
Ekaterina A Chingizova
Svetlana P Ermakova
Olesya S Malyarenko
Author Affiliation
G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Pr. 100-letya Vladivostoka 159, Vladivostok 690022, Russia. sialexandra@mail.ru.
Source
Mar Drugs. 2019 Jun 14; 17(6):
Date
Jun-14-2019
Language
English
Publication Type
Journal Article
Abstract
Seven sulfated triterpene glycosides, psolusosides B (1), E (2), F (3), G (4), H (5), H1 (6), and I (7), along with earlier known psolusoside A and colochiroside D have been isolated from the sea cucumber Psolus fabricii collected in the Sea of Okhotsk. Herein, the structure of psolusoside B (1), elucidated by us in 1989 as a monosulfated tetraoside, has been revised with application of modern NMR and particularly MS data and proved to be a disulfated tetraoside. The structures of other glycosides were elucidated by 2D NMR spectroscopy and HR-ESI mass-spectrometry. Psolusosides E (2), F (3), and G (4) contain holostane aglycones identical to each other and differ in their sugar compositions and the quantity and position of sulfate groups in linear tetrasaccharide carbohydrate moieties. Psolusosides H (5) and H1 (6) are characterized by an unusual sulfated trisaccharide carbohydrate moiety with the glucose as the second sugar unit. Psolusoside I (7) has an unprecedented branched tetrasaccharide disulfated carbohydrate moiety with the xylose unit in the second position of the chain. The cytotoxic activities of the compounds 2-7 against several mouse cell lines-ascite form of Ehrlich carcinoma, neuroblastoma Neuro 2A, normal epithelial JB-6 cells, and erythrocytes-were quite different, at that hemolytic effects of the tested compounds were higher than their cytotoxicity against other cells, especially against the ascites of Ehrlich carcinoma. Interestingly, psolusoside G (4) was not cytotoxic against normal JB-6 cells but demonstrated high activity against Neuro 2A cells. The cytotoxic activity against human colorectal adenocarcinoma HT-29 cells and the influence on the colony formation and growth of HT-29 cells of compounds 1-3, 5-7 and psolusoside A was checked. The highest inhibitory activities were demonstrated by psolusosides E (2) and F (3).
PubMed ID
31207953 View in PubMed
Less detail

7 records – page 1 of 1.