A new sulfated triterpene glycoside from the sea cucumber Colochirus quadrangularis, and evaluation of its antifungal, antitumor and immunomodulatory activities

Progress in the Studies of Triterpene Glycosides From Sea Cucumbers (Holothuroidea, Echinodermata) Between 2017 and 2021

“…The glycoside has a trivial holostane aglycone with 7(8)- and 25(26)-double bonds and a 16β-acetoxy group. 18 Еarlier, the structure of philinopside B was published by Chinese authors as a disulfated glycoside having a structure almost identical to that of 16 , but with an additional sulfate group attached to С-2 of the third monosaccharide residue (xylose) 19 . In the Chinese paper, thorough analysis of the NMR data showed the absence of the second sulfate group in the carbohydrate chain of philinopside B.…”

“…The activities of monosulfated quadrangularisosides of group A (3,4) against Neuro 2a and JB-6 cells, and erythrocytes were relatively low due to the presence of the hydroperoxy group, whereas trisulfated quadrangularisosides D 3 (13) and D 4 (14), with the same aglycones as in 3 and 4, were the least active substances among the tested compounds due to the combination of their structural peculiarities. Erythrocytes were more sensitive to the glycosides than either Neuro 2a or JB-6 cells, but Six new monosulfated triterpene tetra-, penta-and hexaosides, namely, kurilosides A 1 (17), A 2 (18), C 1 (19), D (20), E (21) and F (22), along with the known kuriloside A, having unusual non-holostane aglycones without a lactone, have been isolated from the sea cucumber Thyonidium (=Duasmodactyla) kurilensis (Levin) (Cucumariidae, Dendrochirotida) (Figure 5), collected in the Sea of Okhotsk near Onekotan Island. Their structures were elucidated by 2D NMR spectroscopy and HR-ESI-MS. Kurilosides, belonging to groups A and E, contain carbohydrate chains of rare architecture (a pentasaccharide branched by C-4 Xyl1), and differ from each other in the second sugar (quinovose or glucose, correspondingly).…”

In Vivo and Clinical Studies of Sea Cucumber-Derived Bioactives for Human Health and Nutrition From 2012-2021

“…Coloquadranoside A of sea cucumber Colochirus quadrangularis showed effective immunomodulation activity. Coloquadranoside A at the dose of 50 and 500 mg/kg intragastrically administrated for 14 days increased the clearance index, adjusted phagocytosis index, reversed the lower thymus and spleen index and hemolysin level in the immunosuppressed mouse model which was induced by cyclophosphamide (Yang et al, 2021b)…”

“…Intragastrical administration of coloquadranoside A at the dose of 5 mg/kg and 50mg/kg inhibited (~35%) the weight gaining of tumors in the homograft mouse models, which was same ability as the positive drug, 5-FU. For the xenograft model of human hepatocarcinoma BEL7402, all three doses (5, 50 and 500mg/kg) intragastrically administrated for 25 days significantly lower the average tumor volume weight with the tumor growth inhibition rate > 50% and the relative tumor proliferation rate < 60% (Yang et al, 2021b).…”

Marine natural products

“…The latter glycoside exhibited weak cytotoxicity. Metabolites reported from sea cucumbers included one example of a cerebroside, holospiniferoside 1493 isolated from a Red Sea collection of Holothuria spinifera , 701 and a diverse array of glycosides: HSEA-P1 1494 and HSEA-P2 1495 , from Thai specimens of Holothuria scabra , 702 coloquandranoside A 1496 from a South China Sea collection of Colochirus quandrangularis , 703 echinoside B methyl ether 1497 from Holothuria atra , 704 chitonoidosides A, A 1 , B, C, D, E, E 1 , F, G and H 1498–1507 from Far Eastern specimens of Psolus chitonoides 705,706 and kurilosides A 3 , D 1 , G, H, I, I 1 , J, K and K 1 1508–1516 , isolated from Thyonidium kurilensis (Far Eastern Kurile Islands). 707 HSEA-P1 and HSEA-P2 exhibited weak inhibition of α-synuclein aggregation and in a C. elegans model, rescued α-synuclein-mediated dopaminergic neurodegeneration.…”