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MedKoo Cat#: 598308 | Name: Holothurin A

Description:

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

Holothurin A is a triterpene glycoside.

Chemical Structure

Holothurin A
Holothurin A
CAS#38-26-6

Theoretical Analysis

MedKoo Cat#: 598308

Name: Holothurin A

CAS#: 38-26-6

Chemical Formula: C54H85NaO27S

Exact Mass: 1220.4897

Molecular Weight: 1221.29

Elemental Analysis: C, 53.11; H, 7.02; Na, 1.88; O, 35.37; S, 2.63

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
Holothurin A;
IUPAC/Chemical Name
sodium (3R,4R,5R,6S)-5-(((2S,3R,4R,5S,6R)-5-(((2S,3R,4S,5R,6R)-4-(((2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxytetrahydro-2H-pyran-2-yl)oxy)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-(((3S,3aR,5aS,5bS,7aR,9S,11aS,13S,13aS)-3-((S)-5,5-dimethyltetrahydrofuran-2-yl)-3a,13-dihydroxy-3,5a,8,8,11a-pentamethyl-1-oxo-3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,13-tetradecahydro-1H,3H-naphtho[2',1':4,5]indeno[1,7a-c]furan-9-yl)oxy)-4-hydroxytetrahydro-2H-pyran-3-yl sulfate
InChi Key
KXDQPKMJSMCBEY-VOFJYVFSSA-M
InChi Code
InChI=1S/C54H86O27S.Na/c1-22-39(76-45-38(64)41(33(59)26(20-56)74-45)77-44-37(63)40(70-9)32(58)25(19-55)73-44)35(61)36(62)43(72-22)78-42-34(60)27(81-82(67,68)69)21-71-46(42)75-30-13-15-50(6)24-18-29(57)54-47(65)80-52(8,31-12-14-48(2,3)79-31)53(54,66)17-16-51(54,7)23(24)10-11-28(50)49(30,4)5;/h18,22-23,25-46,55-64,66H,10-17,19-21H2,1-9H3,(H,67,68,69);/q;+1/p-1/t22-,23-,25-,26-,27-,28+,29+,30+,31+,32-,33-,34+,35-,36-,37-,38-,39-,40+,41+,42-,43+,44+,45+,46+,50-,51+,52+,53+,54-;/m1./s1
SMILES Code
CO[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1O)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H]([C@H](OS(=O)([O-])=O)CO[C@H]4O[C@H]5CC[C@]6([C@H](C5(C)C)CC[C@@H]7C6=C[C@@H]([C@]89C(O[C@@]([C@@H]%10CCC(C)(O%10)C)([C@]8(CC[C@@]79C)O)C)=O)O)C)O)C)CO)O)CO)O.[Na+]
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 1,221.29 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: Wang Y, Wang J, Yanagita RC, Liu C, Hu X, Dong P, Xue C, Xue Y. Effects of two sulfated triterpene saponins echinoside A and holothurin A on the inhibition of dietary fat absorption and obesity reduction. Biosci Biotechnol Biochem. 2014;78(1):139-46. doi: 10.1080/09168451.2014.877830. Epub 2014 Apr 14. PubMed PMID: 25036496. 2: Likhatskaia GN, Iarovaia TP, Rudnev VS, Popov AM, Anisomov MM. [Formation of the complex of the triterpene glycoside holothurin A with cholesterol in liposomal membranes]. Biofizika. 1985 Mar-Apr;30(2):358-9. Russian. PubMed PMID: 3986241. 3: Zhao Q, Xue Y, Liu ZD, Li H, Wang JF, Li ZJ, Wang YM, Dong P, Xue CH. Differential effects of sulfated triterpene glycosides, holothurin A1, and 24-dehydroechinoside A, on antimetastasic activity via regulation of the MMP-9 signal pathway. J Food Sci. 2010 Nov-Dec;75(9):H280-8. doi: 10.1111/j.1750-3841.2010.01837.x. Epub 2010 Oct 15. PubMed PMID: 21535601. 4: FRIESS SL, STANDAERT FG, WHITCOMB ER, NIGRELLI RF, CHANLEY JD, SOBOTKA H. Some pharmacologic properties of holothurin A, a glycosidic mixture from the sea cucumber. Ann N Y Acad Sci. 1960 Nov 17;90:893-901. PubMed PMID: 13702086. 5: THRON CD. HEMOLYSIS BY HOLOTHURIN A, DIGITONIN, AND QUILLAIA SAPONIN: ESTIMATES OF THE REQUIRED CELLULAR LYSIN UPTAKES AND FREE LYSIN CONCENTRATIONS. J Pharmacol Exp Ther. 1964 Aug;145:194-202. PubMed PMID: 14214417. 6: THRON CD, PATTERSON RN, FRIESS SL. Further biological properties of the sea cucumber toxin holothurin A. Toxicol Appl Pharmacol. 1963 Jan;5:1-11. PubMed PMID: 13981290. 7: THRON CD, DURANT RC, FRIESS SL. NEUROMUSCULAR AND CYTOTOXIC EFFECTS OF HOLOTHURIN A AND RELATED SAPONINS AT LOW CONCENTRATION LEVELS. III. Ther Ggw. 1964 Mar;103:182-96. PubMed PMID: 14129991. 8: Sukharev SI, Chernomordik LV, Abidor IG. [Reversible electrical breakdown of cholesterol-containing lipid bilayer membranes modified with holothurin A]. Biofizika. 1983 May-Jun;28(3):423-6. Russian. PubMed PMID: 6871264. 9: NIGRELLI RF, JAKOWSKA S. Effects of holothurin, a steroid saponin from the Bahamian sea cucumber (Actinopyga agassizi), on various biological systems. Ann N Y Acad Sci. 1960 Nov 17;90:884-92. PubMed PMID: 13729021. 10: Mats MN, Korkhov VV, Stepanov VR, Kupera EV, Oleĭnikova GK, Anisimov MM. [The contraceptive activity of triterpene glycosides--the total sum of holotoxins A1 and B1 and holothurin A in an experiment]. Farmakol Toksikol. 1990 Mar-Apr;53(2):45-7. Russian. PubMed PMID: 2369955. 11: Sen DK, Lankaranifard G, Narain NK. Effect of holothurin on Trypanosoma musculi infection in three strains of mice. J Protozool. 1981 May;28(2):167-70. PubMed PMID: 7277255. 12: Yamasaki Y, Ito K, Enomoto Y, Sutko JL. Alterations by saponins of passive Ca2+ permeability and Na+-Ca2+ exchange activity of canine cardiac sarcolemmal vesicles. Biochim Biophys Acta. 1987 Mar 12;897(3):481-7. PubMed PMID: 3814597. 13: Popov AM, Rovin IuG, Anisimov MM, Likhatskaia GN, Strigina LI. [Effect of triterpene glycosides on the stability of bilayer lipid membranes, containing different sterols]. Biofizika. 1982 Sep-Oct;27(5):827-31. Russian. PubMed PMID: 7138933. 14: Bahrami Y, Zhang W, Franco C. Discovery of novel saponins from the viscera of the sea cucumber Holothuria lessoni. Mar Drugs. 2014 May 9;12(5):2633-67. doi: 10.3390/md12052633. PubMed PMID: 24821624; PubMed Central PMCID: PMC4052309. 15: Song S, Zhang L, Cao J, Xiang G, Cong P, Dong P, Li Z, Xue C, Xue Y, Wang Y. Characterization of Metabolic Pathways and Absorption of Sea Cucumber Saponins, Holothurin A and Echinoside A, in Vitro and in Vivo. J Food Sci. 2017 Aug;82(8):1961-1967. doi: 10.1111/1750-3841.13759. Epub 2017 Jul 21. PubMed PMID: 28732111. 16: Yu BS, Jo IH. Interaction of sea cucumber saponins with multilamellar liposomes. Chem Biol Interact. 1984 Dec;52(2):185-202. PubMed PMID: 6509686. 17: Enomoto Y, Ito K, Kawagoe Y, Morio Y, Yamasaki Y. Positive inotropic action of saponins on isolated atrial and papillary muscles from the guinea-pig. Br J Pharmacol. 1986 May;88(1):259-67. PubMed PMID: 3708218; PubMed Central PMCID: PMC1917120. 18: Popov AM, Anisimov MM, Ivanov AS, Korepanova EA, Antonov VF. [Characteristics of membrane activity of triterpene glycosides]. Antibiotiki. 1982 Apr;27(4):276-80. Russian. PubMed PMID: 7092199.

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