Frondoside A. A novel triterpene glycoside from the holothurian Cucumariafrondosa

Abstract

1 (1990).The isolation and characterization of a novel triterpene glycoside from the sea cucumber Cucumariaji-ondosa, collected from the Gulf of St. Lawrence, are described. Physico-chemical data obtained on the underivatized saponin are presented in support of structure 1 for frondoside A. The structure is characterized by the presence of a branched oligosaccharidic chain composed of five units. The holostane-type aglycone features an endocyclic double bond at position C-7,8 and a P-acetoxy group at C-16. On dCcrit l'isolation et 1'Clucidation structurale d'un nouveau triterpkne-glycoside, obtenu de l'holothurie Cucumaria ji-ondosa provenant du golfe du St-Laurent. En se basant sur les donnCes physico-chimiques du produit intact, on propose la structure 1 pour le frondoside A. Le composC est caractCrisC par la presence d'une chaine oligosaccharidique branchke, de cinq unites. L'aglycone de type holostane posskde une insaturation en position C-7,8 et un groupement acCtoxy-P en C-16.

Discovery of Novel Saponins from the Viscera of the Sea Cucumber Holothuria lessoni

“…They are reported primarily as typical metabolites of terrestrial plants [25]. A few marine species belonging to the phylum Echinodermata [26] namely holothuroids (sea cucumbers) [7,10,13,27,28,29,30,31,32,33] and asteroids, and sponges from the phylum Porifera [13,34,35] produce saponins.…”

Structural Elucidation of Novel Saponins in the Sea Cucumber Holothuria lessoni

“…Saponins are produced by a limited number of marine species which belong to the phylum Echinodermata [34], namely holothuroids (sea cucumbers) [14,17,20,35,36,37,38,39,40,41], asteroids, and sponges from the phylum Porifera [20,42,43]. They are amphipathic compounds that generally possess a triterpene or steroid backbone or aglycone which in sea cucumbers is of the holostane type [44,45].…”

Relationships between chemical structures and functions of triterpene glycosides isolated from sea cucumbers

“…Last 20 years more than 100 new triterpene glycosides were isolated. Really, only by Russian group from Pacific Institute of Bioorganic Chemistry (PIBOC) at Vladivostok, about 30 new glycosides were isolated from Eupentacta (Cucumaria) fraudatrix (Silchenko et al, 2011, 2012a,b,c,d, 2013b,c), 14 new glycosides from Cucumaria frondosa (Girard et al, 1990; Silchenko et al, 2005a,b, 2007b), 7 from Stuarocucumis liouvillei (Antonov et al, 2008, 2011), 6 from Cladolabes schmeltzi (Silchenko et al, 2013d), 6 from Cucumaria okhotensis (Silchenko et al, 2007a, 2008), 5 from Synallactes nozawai (Silchenko et al, 2002), 5 from Actinocucumis typica (Silchenko et al, 2013a), 4 from Cucumaria conicospermium (Avilov et al, 2003), 3 from Mediterranean species (Silchenko et al, 2005c), 3 from Pentamera calcigera (Avilov et al, 2000a,b), 3 from Australostichopus (Stichopus) mollis (Moraes et al, 2005), 3 from Achlionice violaecuspidata (Antonov et al, 2009), 2 from Synapta maculata (Avilov et al, 2008), 1 from Cucumaria koriaiensis (Avilov et al, 1997), 1 from Psolus eximus (Kalinin et al, 1997), and so on. Several series of structures were also reviewed (Kalinin et al, 2012; Kim and Himaya, 2012).…”

“…Frondoside A has a sulfate, an acetoxy group at C-16 of the aglycone, penta-saccharide chain with xylose as the third monosaccharide residue, and 3- O -methylglucose as the terminal monosaccharide residue (Girard et al, 1990). Cucumarioside A 4 -2 has a 16-keto group in the aglycone and a glucose residue as the third monosaccharide unit in the carbohydrate chain (Kalinin et al, 1992, 1996).…”

“…The structural differences between STC and STD are a sugar residue; STC has quinovose, while STD has glucose as the second monosaccharide unit (indicated as the asterisk in compound 1 and 2). Frondoside A (compound 3) and cucumariosides are derived from the edible sea cucumbers Cucumaria frondosa and C. japonica , respectively (Girard et al, 1990; Stonik et al, 1999) (Figure 2). C. japonica is a source of several different cucumariosides such as cucumarioside A 2 -2 (compound 4), A 4 -2 (compound 5), and A 7 -1 (compound 6) (Figure 2) (Avilov et al, 1990; Drozdova et al, 1993, 1997; Stonik et al, 1999).…”