Triterpene Glycosides from the Deep-Water North-Pacific Sea Cucumber Synallactes nozawai Mitsukuri

Abstract

Five non-sulfated triterpene glycosides, synallactosides A(1) (1), A(2) (2), B(1) (3), B(2) (4), and C (5), have been isolated from the sea cucumber Synallactes nozawai. Their structures have been deduced by extensive analysis of NMR and mass spectra. The glycosides 2-5 are new glycosides. Glycosides 2-4 have carbohydrate chains without precedent in the glycosides from sea cucumbers. This is the first time glycosides are found in members of the family Synallactidae.

New Bacterial Species Isolated from Malaysian Sea Cucumbers with Optimized Secreted Antibacterial Activity

“…Cucumarioside, from C. frondosa was effective against both Gram positive and negative bacteria [3,14] . Other isolates also had varied efficacy [15][16][17][18][19][20][21] . Comparatively, the test samples in this research were more effective against the Gram negative test pathogens (S. typhimurium and K. pneumoniae).…”

“…The assumption here is the test samples may have a terpenoid structure as well, which would explain nominal efficacy against Gram positive bacteria. Most of the triterpene antibacterial agents have large polysaccharide groups and also some sulfates [15][16][17][18][19][20][21] , thus hindering transport across the thicker cell membranes of Gram positive bacteria. High efficacy against Gram negative bacteria could be due to the effectiveness of the terpenoids against the lipopolysaccharide layer of the Gram negative pathogens [25] .…”

“…To date, all isolated antibacterial agents belong to the triterpene glycoside structural configuration. Several subtypes have been determined, namely synallactosides (non-sulfated triterpene glycosides) from Synallactes nozawai [15] , hemoiedemosides (trisulfated triterpene glycosides) from Hemoiedema spectabilis [16] , liouvillosides (trisulfated triterpene glycosides) from Staurocucumis liouvillei [17] , calcigerosides from Pentamera calcigera [18] , eximisoside from Psolus eximius [19] , koreoside from Cucumaria koraiensis [20] and DS-penaustrosides from Pentacta australis [21] .…”

Sea Cucumber Glycosides: Chemical Structures, Producing Species and Important Biological Properties

“…The presence of diverse types of monosaccharide units and their repetitions in the carbohydrate chain can be established by acid hydrolysis followed by GC-MS analysis of the corresponding aldononitrile peracetates [16]. The site of attachment of sulfate group at monosaccharide units can be determined by observing chemical shift of esterification carbon atoms.…”

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).…”