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MedKoo Cat#: 598364 | Name: Cucumarioside C2

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cucumarioside C2 is a sea cucumber glycoside.

Chemical Structure

Cucumarioside C2
Cucumarioside C2
CAS#114129-89-4

Theoretical Analysis

MedKoo Cat#: 598364

Name: Cucumarioside C2

CAS#: 114129-89-4

Chemical Formula: C60H92O26

Exact Mass: 1228.5877

Molecular Weight: 1229.37

Elemental Analysis: C, 58.62; H, 7.54; O, 33.84

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Cucumarioside C2;
IUPAC/Chemical Name
(3R,3aR,4S,5aS,7aS,9R,11aR,11bS,13aS)-9-(((2S,3S,4S,5R)-3-(((2S,3S,4S,5R,6R)-5-(((2R,3R,4R,5R,6S)-4-(((2S,3S,4S,5S)-3,5-dihydroxy-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-6-methyl-3-(((2S,3S,4R,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-3,5a,8,8,11a-pentamethyl-3-((E)-4-methylpenta-1,3-dien-1-yl)-1-oxo-3a,4,5,5a,7,7a,8,9,10,11,11a,11b,12,13-tetradecahydro-1H,3H-naphtho[2',1':4,5]indeno[1,7a-c]furan-4-yl acetate
InChi Key
CGCFPNINLAZUDH-YHGALKRXSA-N
InChi Code
InChI=1S/C60H92O26/c1-25(2)12-11-17-59(9)49-33(79-27(4)62)20-58(8)29-13-14-35-56(5,6)36(16-18-57(35,7)28(29)15-19-60(49,58)55(73)86-59)81-53-47(38(67)31(64)23-77-53)85-54-48(84-50-40(69)37(66)30(63)22-75-50)41(70)44(26(3)78-54)82-52-43(72)46(39(68)34(21-61)80-52)83-51-42(71)45(74-10)32(65)24-76-51/h11-13,17,26,28,30-54,61,63-72H,14-16,18-24H2,1-10H3/b17-11+/t26-,28-,30-,31-,32+,33+,34+,35-,36-,37-,38+,39-,40+,41+,42+,43-,44+,45+,46-,47+,48+,49-,50+,51+,52-,53+,54+,57-,58+,59-,60-/m1/s1
SMILES Code
O[C@@H]1CO[C@H]([C@H]([C@@H]1O)O)O[C@@H]2[C@H](O[C@@H]3[C@H](O[C@@H]4CC[C@]5(C)[C@@H]6CC[C@@]78[C@@](C)(C[C@H](OC(C)=O)[C@@H]7[C@@](C)(/C=C/C=C(C)/C)OC8=O)C6=CC[C@@H]5C4(C)C)OC[C@H]([C@@H]3O)O)O[C@H](C)[C@H](O[C@@H]9[C@H](O)[C@H](O[C@@H]%10OC[C@H](O)[C@H](OC)[C@@H]%10O)[C@H](O)[C@H](CO)O9)[C@@H]2O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,229.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Menchinskaya ES, Pislyagin EA, Kovalchyk SN, Davydova VN, Silchenko AS, Avilov SA, Kalinin VI, Aminin DL. Antitumor activity of cucumarioside A2-2. Chemotherapy. 2013;59(3):181-91. doi: 10.1159/000354156. Epub 2013 Nov 8. PubMed PMID: 24217558. 2: Silchenko AS, Kalinovsky AI, Dmitrenok PS, Kalinin VI, Mazeika AN, Vorobieva NS, Sanina NM, Kostetsky EY. 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. Nat Prod Commun. 2015 Jun;10(6):877-80. PubMed PMID: 26197506. 3: Pislyagin EA, Dmitrenok PS, Gorpenchenko TY, Avilov SA, Silchenko AS, Aminin DL. Determination of cucumarioside A₂-2 in mouse spleen by radiospectroscopy, MALDI-MS and MALDI-IMS. Eur J Pharm Sci. 2013 Jul 16;49(4):461-7. doi: 10.1016/j.ejps.2013.05.017. Epub 2013 May 30. PubMed PMID: 23727465. 4: Reunov AA, Reunov AV, Pimenova EA, Reunova YA, Menchinskaya ES, Lapshina LA, Aminin DL. Cucumarioside A2-2 stimulates apoptotic necrosis in Ehrlich ascites carcinoma cells. Dokl Biol Sci. 2015;462:161-3. doi: 10.1134/S0012496615020040. Epub 2015 Jul 12. PubMed PMID: 26164340. 5: Silchenko AS, Kalinovsky AI, Avilov SA, Andryjaschenko PV, Dmitrenok PS, Menchinskaya ES, Aminin DL, Kalinin VI. Structure of cucumarioside I2 from the sea cucumber Eupentacta fraudatrix (Djakonov et Baranova) and cytotoxic and immunostimulatory activities of this saponin and relative compounds. Nat Prod Res. 2013;27(19):1776-83. doi: 10.1080/14786419.2013.778851. Epub 2013 Apr 11. PubMed PMID: 23574459. 6: Aminin DL, Gorpenchenko TY, Bulgakov VP, Andryjashchenko PV, Avilov SA, Kalinin VI. Triterpene glycoside cucumarioside A(2)-2 from sea cucumber stimulates mouse immune cell adhesion, spreading, and motility. J Med Food. 2011 Jun;14(6):594-600. doi: 10.1089/jmf.2010.1274. Epub 2011 May 9. PubMed PMID: 21554137. 7: Menchinskaya ES, Aminin DL, Avilov SA, Silchenko AS, Andryjashchenko PV, Kalinin VI, Stonik VA. Inhibition of tumor cells multidrug resistance by cucumarioside A2-2, frondoside A and their complexes with cholesterol. Nat Prod Commun. 2013 Oct;8(10):1377-80. PubMed PMID: 24354179. 8: Pislyagin EA, Manzhulo IV, Dmitrenok PS, Aminin DL. Cucumarioside A2-2 causes changes in the morphology and proliferative activity in mouse spleen. Acta Histochem. 2016 May;118(4):387-92. doi: 10.1016/j.acthis.2016.03.009. Epub 2016 Apr 11. PubMed PMID: 27079859. 9: Kostetsky EY, Sanina NM, Mazeika AN, Tsybulsky AV, Vorobyeva NS, Shnyrov VL. Tubular immunostimulating complex based on cucumarioside A2-2 and monogalactosyldiacylglycerol from marine macrophytes. J Nanobiotechnology. 2011 Sep 2;9:35. doi: 10.1186/1477-3155-9-35. PubMed PMID: 21888630; PubMed Central PMCID: PMC3175152. 10: Jin JO, Shastina VV, Shin SW, Xu Q, Park JI, Rasskazov VA, Avilov SA, Fedorov SN, Stonik VA, Kwak JY. Differential effects of triterpene glycosides, frondoside A and cucumarioside A2-2 isolated from sea cucumbers on caspase activation and apoptosis of human leukemia cells. FEBS Lett. 2009 Feb 18;583(4):697-702. doi: 10.1016/j.febslet.2009.01.010. Epub 2009 Jan 20. PubMed PMID: 19162021. 11: Sharova LV, Sedov AM, Stonik VA. [A preclinical study of the embryotoxic properties of cucumarioside and its effect on adult generative function]. Farmakol Toksikol. 1991 Jan-Feb;54(1):60-1. Russian. PubMed PMID: 1860504. 12: Pislyagin EA, Gladkikh RV, Kapustina II, Kim NY, Shevchenko VP, Nagaev IY, Avilov SA, Aminin DL. Interaction of holothurian triterpene glycoside with biomembranes of mouse immune cells. Int Immunopharmacol. 2012 Sep;14(1):1-8. doi: 10.1016/j.intimp.2012.05.020. Epub 2012 Jun 6. PubMed PMID: 22683181. 13: Avilov SA, Kalinin VI, Makarieva TN, Stonik VA, Kalinovsky AI, Rashkes YW, Milgrom YM. Structure of cucumarioside G2, a novel nonholostane glycoside from the sea cucumber Eupentacta fraudatrix. J Nat Prod. 1994 Aug;57(8):1166-71. PubMed PMID: 7964798. 14: Silchenko AS, Kalinovsky AI, Avilov SA, Andryjaschenko PV, Dmitrenok PS, Martyyas EA, Kalinin VI. Triterpene glycosides from the sea cucumber Eupentacta fraudatrix. Structure and cytotoxic action of cucumariosides A2, A7, A9, A10, an, A13 and A14, seven new minor non-sulfated tetraosides and an aglycone with an uncommon 18-hydroxy group. Nat Prod Commun. 2012 Jul;7(7):845-52. PubMed PMID: 22908562. 15: Polikarpova SI, Volkova ON, Sedov AM, Stonik VA, Likhoded VG. [Cytogenetic study of the mutagenicity of cucumarioside]. Genetika. 1990 Sep;26(9):1682-5. Russian. PubMed PMID: 2079212. 16: Sedov AM, Shepeleva IB, Zakharova NS, Sakandelidze OG, Sergeev VV. [Effect of cucumarioside (a triterpene glycoside from the holothurian Cucumaria japonica) on the development of an immune response in mice to corpuscular pertussis vaccine]. Zh Mikrobiol Epidemiol Immunobiol. 1984 Sep;(9):100-4. Russian. PubMed PMID: 6506936. 17: Aminin DL, Silchenko AS, Avilov SA, Stepanov VG, Kalinin VI. Cytotoxic action of triterpene glycosides from sea cucumbers from the genus Cucumaria on mouse spleen lymphocytes. Inhibition of nonspecific esterase. Nat Prod Commun. 2009 Jun;4(6):773-6. PubMed PMID: 19634320. 18: Anisimov MM, Shcheglov VV, Stonik VA, Fronert EB, Elyakov GB. The toxic effect of cucumarioside C from Cucumaria fraudatrix on early embryogenesis of the sea urchin. Toxicon. 1974 May;12(3):327-9. PubMed PMID: 4156431. 19: Agafonova IG, Aminin DL, Avilov SA, Stonik VA. Influence of cucumariosides upon intracellular [Ca2+]i and lysosomal activity of macrophages. J Agric Food Chem. 2003 Nov 19;51(24):6982-6. PubMed PMID: 14611158. 20: Li IA, Popov AM, Tsybul'skiĭ AV, Sanina NM, Kostetskiĭ EIa, Novikova OD, Portniagina OIu, Mazeĭka AV. [Immunostimulatory characteristics of a novel carrier on the basis of cucumarioside A2-2 and monogalactosyldiacylgycerol]. Prikl Biokhim Mikrobiol. 2008 Nov-Dec;44(6):694-700. Russian. PubMed PMID: 19145978.

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