Free accessResearch articleFirst published online 2015-6
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
New minor triterpene glycoside, cucumarioside E (1) has been isolated from the Far Eastern sea cucumber Cucumaria japonica. The structure of the glycoside was elucidated by 2D-NMR specroscopy and mass-spectrometry. The glycoside has glucose instead of quinovose as the second monosaccharide residue and xylose as third monosaccharide residue that is unique structural feature for triterpene glycosides carbohydrate chains from sea cucumbers belonging to the genus Cucumaria.
AvilovSA, KalininVI, SmirnovAV. (2004) Use of triterpene glycosides for resolving taxonomic problems in the sea cucumber genus Cucumaria (Holothorioidea, Echinodermata). Biochemical Systematics and Ecology, 32, 715–733.
2.
AvilovSA, StonikVA, KalinovskyAI. (1990) Structure of four new triterpene glycosides from the sea cucumber Cucumaria japonica. Khimya Prirodnykh Soedinenij, 6, 787–792.
3.
DrozdovaOA, AvilovSA, KalininVI, KalinovskyAI, StonikVA, RigueraR, JimenezC. (1997) Cytotoxic triterpene glycosides from Far-Eastern sea cucumbers belonging to the genus Cucumaria. Liebigs Annalen der Chemie, 2351–2356.
4.
DrozdovaOA, AvilovS.A., KalinovskyAI, StonikVA, MilgromYM, RashkesJW. (1993) Trisulfated glycosides from the sea cucumber Cucumaria japonica. Khimiya Prirodnykh Soedinenij, 3, 369–374.
5.
GirardM, BelangerJ, ApSimonJW, GarneauF-X, HarveyC, BrissonJ-R. (1990) Frondoside A. A novel triterpene glycoside from the holothurian Cucumaria frondosa. Canadian Journal of Chemistry, 68, 11–18.
6.
ShashkovAS, ChizhovOS. (1976) 13C NMR spectroscopy in chemistry of carbohydrates and relative compounds. Bioorganicheskaya Khimiya, 2, 437–497.
7.
SilchenkoAS, KalinovskyAI, AvilovSA, AndryjashenkoPV, DmitrenokPS, MartyyasEA, KalininVI. (2012) Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and biological actions of cucumariosides A1, A3, A4, A5, A6, A12 and A15, seven new minor non-sulfated tetraosides and unprecedented 25-keto,25-norholostane aglycone. Natural Product Communications, 7, 517–525.
8.
SilchenkoAS, KalinovskyAI, AvilovSA, AndryjaschenkoPV, DmitrenokPV, MartyyasEA, KalininVI. (2012) Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and cytotoxic action of cucumariosides A2, A7, A9, A10, A11, A13 and A14, seven new minor non-sulated tetraosides and an aglycone with an uncommon 18-hydroxy group. Natural Product Communications, 7, 845–852.
9.
SilchenkoAS, KalinonovskyAI, AvilovSA, AndryjashenkoPV, DmitrenokPS, KalininVI, StonikVA (2012) 3β-O-Glycosylated 16β-acetoxy-9β-H-lanosta-7,24-diene-3p,18,20β-triol, an intermediate metabolite from the sea cucumber Eupentacta fraudatrix and its biosynthetic significance. Biochemical Systematics and Ecology, 44, 53–60.
10.
StonikVA, KalininVI, AvilovSA. (1999) Toxins from the sea cucumbers (Holothuroids): Chemical structures, properties, taxonomic distribution, biosynthesis and evolution. Journal of Natural Toxins, 8, 235–248.
11.
ZhangS-Y, YiY-H, TangH-F, LiL, SunP, WuJ. (2006) Two new bioactive triterpene glycosides from the sea cucumber Pseudocolochirus violaceus. Journal of Asian Natural Products Research, 8, 1–8.
12.
ZhangS-L, LiL, YiY-H, SunP. (2006) Philinopsides E and F, two new sulfated triterpene glycosides from the sea cucumber Pentacta quadrangularis. Natural Product Research, 20, 399–407.
13.
ZhangSL., LiL, SunP, YiYH. (2008) Lecanorosides A and B, two new triterpene glycosides from the sea cucumber Actinopyga lecanora. Journal of Asian Natural Products Research, 10, 1097–1103.
14.
SilchenkoAS, AvilovSA, KalininVI, StonikVA, KalinovskyAI, DmitrenokPS, StepanovVG. (2007) Monosulfated triterpene glycosides of Cucumaria okhotensis Levin et Stepanov – new sea cucumber species from the Sea of Okhotsk. Bioorganicheskaya Khimiya, 33, 81–90.
15.
SilchenkoAS, AvilovSA, KalininVI, KalinovskyAI, DmitrenokPS, FedorovSN, StepanovVG, DongZ, StonikVA. (2008) Constituents of the sea cucumber Cucumaria okhotensis. Structures of okhotosides B1–B3 and cytotoxic activities of some glycosides from this species. Journal of Natural Products, 71, 351–356.
16.
LeonteinK, LindbergB, LonngrenJ. (1978) Assignment of absolute configuration of sugars by g.l.c. of their acetylated glycosides formed from chiral alcohols. Carbohydrate Research, 62, 359–362.
