Triterpene glycoside from sea cucumbers

BIOLOGICALLY ACTIVE TRITERPENE GLYCOSIDES FROM SEA CUCUMBERS (HOLOTHUROIDEA, ECHINODERMATA)... 

Table 3. The spectrum of antimicrobial action of triterpene glycosides from sea cucumbers of the family Stichopodidae and their derivatives...

The importance of a linear tetrasaccharide fragment and an 18(20)-lactone for biological activity, the absence of a significant contribution of 4-0-sulfate at first xylose to activities of tetraosides and, in contrast, its important role for activity of biosides were shown for hemolytic action of triterpene glycosides from sea cucumbers [33]. It confirmed a common mechanism of their activity against membranes of both erythrocytes and fungal cells. 

A strong membranotropic action and high solubility of most triterpene glycosides from sea cucumbers, associated with the presence of monosaccharide units, sulfate groups and functional... 

Bioactive Natural Products, Part I, ed. Atta-ur-Rahman, in Studies in Natural Products Chemistry, Vol. 28, Elsevier Science B.V., 2003 R 136 A. Braca, A.R. Bilia, J. Mendez, C. Pizza, I. Morelli and N. De Tommasi, Chemical and Biological Studies on Licania Genus , p. 35 R 137 H.D. Chludil, A.P. Murray, A.M. Seldes and M.S. Maier, Biologically Active Triterpene Glycosides from Sea Cucumbers (Holothuroidea, Echinodermata) , p. 587... 

Chludil, H.D., Murray, A.P., Seldes, A.M., and Maier, M.S. (2003b) Biologically active triterpene glycosides from sea cucumbers (Holothuoidea, Echinodermata). Stud. Nat. Prod. Chem., 28, 587-615. 

Kalinin, V.L, Avilov, SA., and Stonik, VA (2000) Triterpene glycosides from sea cucumbers (Holofhurioidea) structure, function and evolution, in Saponins in Food, Feed uffs and Medicinal Plants (eds W. Oleszek and A Marston), Wuwer Academic Publishers, Dordrecht, The Netherlands, pp. 155-162. 

Triterpene glycosides of sea cucumbers demonstrate a wide spectrum of biological effects antifungal, antitumor, hemolytic, cytostatic and immunomodulatory activities [12]. The application of many preparations from sea cucumbers in traditional oriental medicine has been reported [13]. The medicinal properties of these sea food preparations are attributed to triterpene glycosides [13]. 

The crude holothurins from Philippine sea cucumbers belonging to Holothuriidae family have indirect mutagenic and clastogenic activity. Although no activity was noted in vitro (Rec- assay and Ames test) after metabolic activation, these holothurins produced aberration scores in Swiss albino mice (micronuclear test) when administered intraperitoneally [29]. Nevertheless, at peroral injection, they exhibited a 35-fold reduction in activity, which indicates inactivation in the alimentary canal [29]. On the contrary, Polycarpova et al. showed the absence of mutagenic activity of cucumarioside - triterpene glycoside from the sea cucumber Cucumaria Japonica [27]. 

We have studied hemolytic action of a series of triterpene glycosides and their derivatives (3-15) from sea cucumbers belonging to the order Dendrochirotida [33]. 

To investigate the influence of quantity and position of sulfate groups in carbohydrate moieties, we have studied kinetic parameters of hemolysis and loss from erythocytes of another series of triterpene glycosides and their derivatives from sea cucumbers in the order Dendrochirotida [34]. 

Most of sea cucumber triterpene glycosides are tetra- or pentaglycosides. The majority of tetrasaccharides show a linear chain with the most common 3-0-Me-Glc-(l—>3)-Glc-(1 4)-Qui-(l—>2)-Xyl structure. The few disaccharides that have been isolated show a Qui-(1 2)-4-0S03Na-Xyl chain attached to C-3 of the triterpenoid aglycone. Some hexasaccharides have been isolated from sea cucumbers of the order Aspidochirota Stichopus japonica, Stichopus chloronotus, Parastichopus californius and Bohadschia bivittata [55]. They are non-sulfated glycosides with a linear 3-0-Me-Glc-(1 3)-Glc-(l- 4)-Xyl chain and a branching of a linear trisaccharide at C-2 of the xylose unit. 

Five non-sulfated triterpene glycosides, synallactosides Ai (52a), A2 (52b), Bi (52c), B2 (52d) and C (52e), Fig. (21) were isolated from the deep-water North Pacific sea cucumber Synallactes nozawai [73]. Synallactoside Ai is the 25,26-dehydro derivative of thelenotoside A, isolated from Thelenota ananas as a mixture with thelenotoside A [74]. Compounds 52b-52e are new compounds with interesting features in the carbohydrate chains of synallactosides A2, Bi, and B2. Synallactoside A2 (52b) is the first glycoside isolated from sea cucumbers with two terminal 3-(9-methylxylose residues in the oligosaccharide chain. On the other hand, the carbohydrate chains of synallactosides Bi (52c) and B2 (52d) have unprecedent structures among holothurins. 

In the last four years, five new sulfated and two new non sulfated triterpene glycosides containing the aglycone 3[3-hydroxyholst-9(l l)-en-16-one (Structure 57), Fig. (25) have been isolated from sea cucumbers. 

Avilov, S.A., Antonov, A.S., Drozdova, OA., Kalinin, V.I., Kalinovsky, A.I., Stonik, V.A., Riguera, R., and Jimenez, C. (2000a) Triterpene glycosides from the far-eastern sea cucumber Pentamera calcigera. 1. Monosulfrted glycosides and cytotoxicity of their imsidfated derivatives. J. Nat. Prod., 63, 65-71. 

Smirnov, A.V., Dmitrenok, P.S., Evtushenko, E.V., Fedorov, S.N., Savina, A.S., Shubina, LK., and Stonik, V.A. (2008) Synaptosides A and A], triterpene glycosides from the sea cucumber Synapta maculata containing 3-O-methylglucuronic add and iheir cytotoxic activity against tumor cells./. Nat. Prod., 71, 525-531. 

Kumar, R., Chaturvedi, A.K., Shukla, P.K., and Lakshmi, V. (2007) Antifungal activity in triterpene glycosides from the sea cucumber Actinopyga lecanora. Bioorg. Med. Chem. Lett., 17,4387—4391. 

---