Synonym
Laxogenin; 6-Oxotigogenin;
IUPAC/Chemical Name
(2aS,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-4-hydroxy-5',6a,8a,9-tetramethylicosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-2(1H)-one
InChi Key
WOJKRRDDERNLBU-BOYSPROGSA-N
InChi Code
InChI=1S/C27H42O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-21,23-24,28H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,23+,24+,25-,26+,27-/m1/s1
SMILES Code
C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)CC[C@H]5[C@H]4CC([C@@H]6[C@]5(C)CC[C@H](O)C6)=O)O2
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
430.62
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.
| 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 |
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2: AKAHORI A, YASUDA F. [Laxogenin, a new steroidal sapogenin isolated from Smilax sieboldi Miq]. Yakugaku Zasshi. 1963 May;83:557-8. Japanese. PubMed PMID: 14041495.
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6: Yu B, Tao H. Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and xiebai saponin I. J Org Chem. 2002 Dec 13;67(25):9099-102. PubMed PMID: 12467439.
7: Timité G, Mitaine-Offer AC, Miyamoto T, Tanaka C, Mirjolet JF, Duchamp O, Lacaille-Dubois MA. Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum. Phytochemistry. 2013 Apr;88:61-6. doi: 10.1016/j.phytochem.2012.12.001. Epub 2013 Jan 25. PubMed PMID: 23357597.
8: Zhang YW, Morita I, Zhang L, Shao G, Yao XS, Murota S. Screening of anti-hypoxia/reoxygenation agents by an in vitro method. Part 2: Inhibition of tyrosine kinase activation prevented hypoxia/reoxygenation-induced injury in endothelial gap junctional intercellular communication. Planta Med. 2000 Mar;66(2):119-23. PubMed PMID: 10763583.
9: Zhang YW, Morita I, Shao G, Yao XS, Murota S. Screening of anti-hypoxia/reoxygenation agents by an in vitro model. Part 1: Natural inhibitors for protein tyrosine kinase activated by hypoxia/reoxygenation in cultured human umbilical vein endothelial cells. Planta Med. 2000 Mar;66(2):114-8. PubMed PMID: 10763582.
10: Pérez-Labrada K, Brouard I, Estévez S, Marrero MT, Estévez F, Bermejo J, Rivera DG. New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides. Bioorg Med Chem. 2012 Apr 15;20(8):2690-700. doi: 10.1016/j.bmc.2012.02.026. Epub 2012 Feb 15. PubMed PMID: 22405922.
