Cucumarioside E from the Far Eastern Sea Cucumber <i>Cucumaria japonica</i> (Cucumariidae, Dendrochirotida), New Minor Monosulfated Holostane Triterpene Pentaoside with Glucose as the Second Monosaccharide Residue

Silchenko, Alexandra S.; Kalinovsky, Anatoly I.; Dmitrenok, Pavel S.; Kalinin, Vladimir I.; Mazeika, Andrey; Vorobieva, Natalia; Sanina, N. M.; Kostetsky, E. Ya.

doi:10.1177/1934578x1501000621

Cited by 4 publications

(5 citation statements)

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“…So, the aglycone of psolusoside H (5) is a positional isomer (by the double bond position in polycyclic nucleus) of the aglycone comprising psolusosides E (2), F (3), and G (4). This aglycone was found earlier in the glycosides of sea cucumbers belonging to different orders: Cucumaria japonica [20,21], Pseudocolochirus violaceus [22] (Cucumariidae, Dendrochirotida), and Australostichopus mollis [23] (Stichopodidae, Synallactida) [24]. Table 8.…”

Section: Structural Elucidation Of the Glycosidessupporting

confidence: 52%

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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

et al. 2019

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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).

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Section: Structural Elucidation Of the Glycosidessupporting

confidence: 52%

“…Table 7. 13 The molecular formula of psolusoside H (5) was determined to be C 47 H 71 O 21 Table 8, Figures S33 and S34). The characteristic signals at δ(C) 121.7 (C(7)), 143.9 (C(8)), and at δ(H) 5.63 (m, H (7)) in the 13 C and 1 H NMR spectra of 5 were assigned to 7(8)-double bond in the polycyclic system.…”

Section: Structural Elucidation Of the Glycosidesmentioning

confidence: 99%

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

et al. 2019

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“…A new carotenoid 1335 was reported from Plesiocolochirus minutus, with absolute conguration assigned by a combination of ECD and NOESY analysis, 971 while the structure of 3 0 -epigobiusxanthin (Crown-of-thorns Acanthaster planci) 972 has been corrected to that of 6 0 -epigobiusxanthin 1336 as a consequence of stereospecic synthesis of a series of stereoisomers. 973 The remaining metabolites reported from echinoderms were of saccharide or sterol/sterol glycoside origins and included 1337 (starsh Asterias rollestoni) 974 1338-1341 (starsh Leptasterias ochotensis), 975 1342 (sea cucumber Holothuria moebii), 976 1343-1347 (starsh Echinaster luzonicus), 977 1348-1352 (sea cucumber Cercodemas anceps), 978 1353 (starsh Culcita novaeguineae), 979 1354 (sea cucumber Cucumaria japonica), 980 and 1355-1362 (sea cucumber Cladolabes schmeltzii). 981 In addition to these MNPs, a further series of saponins (lessoniosides A-G) were reported from Holothuria lessoni.…”

Section: Echinodermsmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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“…Product ion mass spectra were recorded in auto MS/MS mode. Identification of compounds was carried out according to the Bruker library and literature data [ 11 , 16 , 17 ].…”

Section: Methodsmentioning

confidence: 99%

Features and Advantages of Supercritical CO2 Extraction of Sea Cucumber Cucumaria frondosa japonica Semper, 1868

et al. 2020

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Extraction process of Cucumaria frondosa japonica Semper, 1868, which are subspecies of Cucumaria frondosa (Gunnerus, 1767), were studied. It was shown that supercritical carbon dioxide extraction of holothuria was more effective than conventional solvent extraction. Step-by-step extraction with carbon dioxide followed by supercritical extraction with the addition of a co-solvent of ethanol can almost double the yields of extracts of triterpene glycosides, styrenes and carotenoids. Moreover, the fraction of triterpene glycosides practically does not contain colored impurities, in contrast to traditional ethanol extraction. The obtained extracts by HPLC in combination with tandem mass spectrometry (HPLC-MS/MS) identified 15 triterpene glycosides, 18 styrene compounds and 14 carotenoids. Supercritical extraction made it possible to obtain extracts with yields superior to conventional hexane and alcohol extracts. Moreover, such an approach with the use of supercritical fluid extraction (SFE) and subsequent profiling of metabolites can help with the study of holothuria species that are not as well studied.

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Cucumarioside E from the Far Eastern Sea Cucumber Cucumaria japonica (Cucumariidae, Dendrochirotida), New Minor Monosulfated Holostane Triterpene Pentaoside with Glucose as the Second Monosaccharide Residue

Cited by 4 publications

References 14 publications

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

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

Marine natural products

Features and Advantages of Supercritical CO2 Extraction of Sea Cucumber Cucumaria frondosa japonica Semper, 1868

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