WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 461704
CAS#: 5092-09-1
Description: Saikogenin A is an anti-inflammatory drug that is present in the crude extract of a Chinese herbal plant called Tsai-Fu.
MedKoo Cat#: 461704
Name: Saikogenin A
CAS#: 5092-09-1
Chemical Formula: C30H48O4
Exact Mass: 472.3553
Molecular Weight: 472.71
Elemental Analysis: C, 76.23; H, 10.24; O, 13.54
This product is not in stock, which may be available by custom synthesis.
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Synonym: Saikogenin A; Saikogenin D;
IUPAC/Chemical Name: (3S,4R,4aR,6aR,6bS,8S,8aS,14aR,14bS)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,14a,14b-octadecahydropicene-3,8-diol
InChi Key: QGNVMEXLLPGQEV-HSFRRAFJSA-N
InChi Code: InChI=1S/C30H48O4/c1-25(2)13-14-30(18-32)20(15-25)19-7-8-22-26(3)11-10-23(33)27(4,17-31)21(26)9-12-28(22,5)29(19,6)16-24(30)34/h7-8,21-24,31-34H,9-18H2,1-6H3/t21-,22-,23+,24+,26+,27+,28-,29-,30-/m1/s1
SMILES Code: C[C@@]1(CO)[C@@H](O)CC[C@]2(C)[C@@]3([H])C=CC4=C5CC(C)(C)CC[C@@](CO)5[C@@H](O)C[C@](C)4[C@@](C)3CC[C@@]12[H]
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
The following data is based on the product molecular weight 472.71 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 |
1: Cheng JT, Tsai CL. Anti-inflammatory effect of saikogenin A. Biochem Pharmacol. 1986 Aug 1;35(15):2483-7. PubMed PMID: 2427082.
2: Zeng B, Liu GD, Zhang BB, Wang SS, Ma R, Zhong BS, He BQ, Liang Y, Wu FH. A new triterpenoid saponin from Clinopodium chinense (Benth.) O. Kuntze. Nat Prod Res. 2016;30(9):1001-8. doi: 10.1080/14786419.2015.1095745. Epub 2015 Oct 29. PubMed PMID: 26511166.
3: Shibata S, Kitagawa I, Fujimoto H. The chemical studies on oriental plant drugs. XV. On the constituents of Bupleurum Spp. (2). The structure of saikogenin A, a sapogenin of Bupleurum falcatum L. Chem Pharm Bull (Tokyo). 1966 Sep;14(9):1023-33. PubMed PMID: 5976509.
4: Shibata S, Kitagawa I, Fujimoto H. The structure of saikogenin A, a sapogenin of Bupleurum species. Tetrahedron Lett. 1965 Oct;(42):3783-8. PubMed PMID: 5842888.
5: Kumazawa Y, Kawakita T, Takimoto H, Nomoto K. Protective effect of saikosaponin A, saikosaponin D and saikogenin D against Pseudomonas aeruginosa infection in mice. Int J Immunopharmacol. 1990;12(5):531-7. PubMed PMID: 2210914.
6: Nose M, Amagaya S, Ogihara Y. Effects of saikosaponin metabolites on the hemolysis of red blood cells and their adsorbability on the cell membrane. Chem Pharm Bull (Tokyo). 1989 Dec;37(12):3306-10. PubMed PMID: 2632076.
7: Toriniwa Y, Lv X, Kodama Y, Ohizumi Y, Yoshida M, Nakahata N. Participation of epoxygenase activation in saikogenin D-induced inhibition of prostaglandin E(2) synthesis. J Pharm Pharmacol. 2006 Jun;58(6):859-66. PubMed PMID: 16734988.
8: Shibata M, Yoshida R, Motoashi S, Fukushima M. [Pharmacological studies on Bupleurum falcatum L. IV. Some pharmacological effects of crude saikosides, saikogenin A and syrupy residue (author's transl)]. Yakugaku Zasshi. 1973 Dec;93(12):1660-7. Japanese. PubMed PMID: 4798800.
9: Shimizu K, Amagaya S, Ogihara Y. Structural transformation of saikosaponins by gastric juice and intestinal flora. J Pharmacobiodyn. 1985 Sep;8(9):718-25. PubMed PMID: 4087133.
10: Kodama Y, Xiaochuan L, Tsuchiya C, Ohizumi Y, Yoshida M, Nakahata N. Dual effect of saikogenin D: in vitro inhibition of prostaglandin E2 production and elevation of intracellular free Ca2+ concentration in C6 rat glioma cells. Planta Med. 2003 Aug;69(8):765-7. PubMed PMID: 14531029.
11: Nose M, Amagaya S, Ogihara Y. Corticosterone secretion-inducing activity of saikosaponin metabolites formed in the alimentary tract. Chem Pharm Bull (Tokyo). 1989 Oct;37(10):2736-40. PubMed PMID: 2611932.
12: Bao Y, Li C, Shen H, Nan F. Determination of saikosaponin derivatives in Radix bupleuri and in pharmaceuticals of the chinese multiherb remedy xiaochaihu-tang using liquid chromatographic tandem mass spectrometry. Anal Chem. 2004 Jul 15;76(14):4208-16. PubMed PMID: 15253665.
13: Jung HJ, Kim SG, Nam JH, Park KK, Chung WY, Kim WB, Lee KT, Won JH, Choi JW, Park HJ. Isolation of saponins with the inhibitory effect on nitric oxide, prostaglandin E2 and tumor necrosis factor-alpha production from Pleurospermum kamtschaticum. Biol Pharm Bull. 2005 Sep;28(9):1668-71. PubMed PMID: 16141537.
14: Kida H, Akao T, Meselhy MR, Hattori M. Metabolism and pharmacokinetics of orally administered saikosaponin b1 in conventional, germ-free and Eubacterium sp. A-44-infected gnotobiote rats. Biol Pharm Bull. 1998 Jun;21(6):588-93. PubMed PMID: 9657043.
15: Tundis R, Bonesi M, Deguin B, Loizzo MR, Menichini F, Conforti F, Tillequin F, Menichini F. Cytotoxic activity and inhibitory effect on nitric oxide production of triterpene saponins from the roots of Physospermum verticillatum (Waldst & Kit) (Apiaceae). Bioorg Med Chem. 2009 Jul 1;17(13):4542-7. doi: 10.1016/j.bmc.2009.05.006. Epub 2009 May 8. PubMed PMID: 19467877.
