Saikosaponin A | CAS#20736-09-8 | anti-inflammatory agent

MedKoo Cat#: 461707 | Name: Saikosaponin A

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Description:

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

Saikosaponin A is a bioactive triterpene saponin with anti-inflammatory effects.

Chemical Structure

Saikosaponin A

CAS#20736-09-8

Theoretical Analysis

MedKoo Cat#: 461707

Name: Saikosaponin A

CAS#: 20736-09-8

Chemical Formula: C42H68O13

Exact Mass: 780.4660

Molecular Weight: 780.99

Elemental Analysis: C, 64.59; H, 8.78; O, 26.63

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 270.00
10mg	USD 460.00
25mg	USD 850.00

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Related CAS #

20736-09-8

Synonym

Saikosaponin A;

IUPAC/Chemical Name

(2S,3R,4S,5S,6R)-2-(((2R,3R,4S,5R,6R)-3,5-dihydroxy-2-(((4R,4aR,6aR,6bS,8R,8aS,12aR,12bS,14aR,14bS)-8-hydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-2,3,4,4a,5,6,6a,6b,7,8,10,11,12,12a,14a,14b-hexadecahydro-1H,9H-12b,8a-(epoxymethano)picen-3-yl)oxy)-6-methyltetrahydro-2H-pyran-4-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

InChi Key

KYWSCMDFVARMPN-PKUQORSISA-N

InChi Code

InChI=1S/C42H68O13/c1-21-28(46)33(55-34-31(49)30(48)29(47)22(18-43)53-34)32(50)35(52-21)54-27-10-11-37(4)23(38(27,5)19-44)8-12-39(6)24(37)9-13-42-25-16-36(2,3)14-15-41(25,20-51-42)26(45)17-40(39,42)7/h9,13,21-35,43-50H,8,10-12,14-20H2,1-7H3/t21-,22-,23-,24-,25-,26-,27?,28-,29-,30+,31-,32-,33+,34+,35+,37+,38+,39-,40+,41-,42+/m1/s1

SMILES Code

O[C@H]([C@H]([C@@H]([C@@H](C)O1)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)[C@@H]1OC3CC[C@]4(C)[C@@]5([H])C=C[C@]67[C@]8([H])CC(C)(C)CC[C@@](CO7)8[C@H](O)C[C@](C)6[C@@](C)5CC[C@]([H])4[C@]3(C)CO

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, DMF, and ethanol

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Saikosaponin A has anti-inflammatory, antiallergic, anticonvulsive, antiproliferative, and antiviral properties. Saikosaponin A reduced expression of TNF-α, IL-6, and IL-1β in primary mouse macrophages stimulated by LPS and reduced the duration and frequency of epileptiform activity in rat hippocampal CA1 neurons. Saikosaponin A decreased viability in six HCC, H358 lung and MCF-7 breast cancer, as well as Jurkat and K582 leukemia cell lines. It also prolonged tumor growth inhibition in LoVo and SW480 HCC mouse xenograft models.

In vitro activity:

Saikosaponin A exerted inhibitory effects on pancreatic cancer cells. Increased concentration of Saikosaponin A increased the proportions of BxPC-3 and MIA PaCa-2 cells in the G0/G1 phase, the proportions of early and late apoptotic cells, and the apoptosis rate. Saikosaponin A promoted the activation of caspase 3 to induce apoptosis in pancreatic cancer cells. Saikosaponin A treatment significantly reduced the levels of phosphorylated EGFR, Akt, and PI3K in both cell lines. Reference: Curr Pharm Biotechnol. 2023;24(4):579-588. https://pubmed.ncbi.nlm.nih.gov/35692139/

In vivo activity:

In a murine model of post-stroke depression, Saikosaponin A improved depression-like behavior and inhibited hippocampal neuronal apoptosis after cerebral ischemia. Saikosaponin A significantly ameliorated depressive-like behavior; inhibited neuronal apoptosis; enhanced the levels of p-CREB, BDNF and Bcl-2; and reduced the level of Bax, Caspase-3 in the hippocampus of PSD rats. Reference: Behav Brain Res. 2021 Apr 9;403:113138. https://pubmed.ncbi.nlm.nih.gov/33493495/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	38.41
	DMSO	30.0	38.41
	Ethanol	30.0	38.41
	Ethanol:PBS (pH 7.2) (1:9)	0.1	0.13

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 780.99 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

Formulation protocol:

1. Shi C, Sun L, Fang R, Zheng S, Yu M, Li Q. Saikosaponin-A Exhibits Antipancreatic Cancer Activity by Targeting the EGFR/PI3K/Akt Pathway. Curr Pharm Biotechnol. 2023;24(4):579-588. doi: 10.2174/1389201023666220610113514. PMID: 35692139. 2. Lim SH, Lee HS, Han HK, Choi CI. Saikosaponin A and D Inhibit Adipogenesis via the AMPK and MAPK Signaling Pathways in 3T3-L1 Adipocytes. Int J Mol Sci. 2021 Oct 22;22(21):11409. doi: 10.3390/ijms222111409. PMID: 34768840; PMCID: PMC8583978. 3. Wang AR, Mi LF, Zhang ZL, Hu MZ, Zhao ZY, Liu B, Li YB, Zheng S. Saikosaponin A improved depression-like behavior and inhibited hippocampal neuronal apoptosis after cerebral ischemia through p-CREB/BDNF pathway. Behav Brain Res. 2021 Apr 9;403:113138. doi: 10.1016/j.bbr.2021.113138. Epub 2021 Jan 22. Erratum in: Behav Brain Res. 2023 Aug 24;452:114596. PMID: 33493495. 4. Song Y, Sun H, Gao S, Tang K, Zhao Y, Xie G, Gao H. Saikosaponin a attenuates lead-induced kidney injury through activating Nrf2 signaling pathway. Comp Biochem Physiol C Toxicol Pharmacol. 2021 Apr;242:108945. doi: 10.1016/j.cbpc.2020.108945. Epub 2020 Dec 3. PMID: 33278595.

In vitro protocol:

In vivo protocol:

1. Wang AR, Mi LF, Zhang ZL, Hu MZ, Zhao ZY, Liu B, Li YB, Zheng S. Saikosaponin A improved depression-like behavior and inhibited hippocampal neuronal apoptosis after cerebral ischemia through p-CREB/BDNF pathway. Behav Brain Res. 2021 Apr 9;403:113138. doi: 10.1016/j.bbr.2021.113138. Epub 2021 Jan 22. Erratum in: Behav Brain Res. 2023 Aug 24;452:114596. PMID: 33493495. 2. Song Y, Sun H, Gao S, Tang K, Zhao Y, Xie G, Gao H. Saikosaponin a attenuates lead-induced kidney injury through activating Nrf2 signaling pathway. Comp Biochem Physiol C Toxicol Pharmacol. 2021 Apr;242:108945. doi: 10.1016/j.cbpc.2020.108945. Epub 2020 Dec 3. PMID: 33278595.

1: Chen J, Duan M, Zhao Y, Ling F, Xiao K, Li Q, Li B, Lu C, Qi W, Zeng Z, Liao M, Liu Y, Chen W. Saikosaponin A inhibits influenza A virus replication and lung immunopathology. Oncotarget. 2015 Dec 15;6(40):42541-56. doi: 10.18632/oncotarget.6448. PubMed PMID: 26637810; PubMed Central PMCID: PMC4767451. 2: Zhou X, Cheng H, Xu D, Yin Q, Cheng L, Wang L, Song S, Zhang M. Attenuation of neuropathic pain by saikosaponin a in a rat model of chronic constriction injury. Neurochem Res. 2014 Nov;39(11):2136-42. doi: 10.1007/s11064-014-1407-y. Epub 2014 Aug 9. PubMed PMID: 25107300. 3: Zhou C, Liu W, He W, Wang H, Chen Q, Song H. Saikosaponin a inhibits RANKL-induced osteoclastogenesis by suppressing NF-κB and MAPK pathways. Int Immunopharmacol. 2015 Mar;25(1):49-54. doi: 10.1016/j.intimp.2015.01.010. Epub 2015 Jan 20. PubMed PMID: 25617149. 4: Meng J, Chen XF, Yang WY, Li ZF, Zhang Y, Song JH, Yang XW. [Effect of combined application of zinc, boron and molybdenum on yield and saikosaponin a, saikosaponin d contents of Bupleurum chinense]. Zhongguo Zhong Yao Za Zhi. 2014 Nov;39(22):4297-303. Chinese. PubMed PMID: 25850256. 5: Zhang GS, Hu PY, Li DX, He MZ, Rao XY, Luo XJ, Wang YS, Wang YR. Formulations, hemolytic and pharmacokinetic studies on saikosaponin a and saikosaponin d compound liposomes. Molecules. 2015 Apr 3;20(4):5889-907. doi: 10.3390/molecules20045889. PubMed PMID: 25854754. 6: Chao Z, Cui Q, Tian E, Zeng W, Cai X, Li X, Tanaka H, Shoyama Y, Wu Y. Ultrasensitive Time-Resolved Fluoroimmunoassay for Saikosaponin a in Chaihu (Bupleuri Radix). PLoS One. 2016 Mar 11;11(3):e0151032. doi: 10.1371/journal.pone.0151032. eCollection 2016. PubMed PMID: 26968034; PubMed Central PMCID: PMC4788217. 7: Zhao H, Li S, Zhang H, Wang G, Xu G, Zhang H. Saikosaponin A protects against experimental sepsis via inhibition of NOD2-mediated NF-κB activation. Exp Ther Med. 2015 Aug;10(2):823-827. Epub 2015 Jun 10. PubMed PMID: 26622400; PubMed Central PMCID: PMC4509026. 8: Chen MF, Huang CC, Liu PS, Chen CH, Shiu LY. Saikosaponin a and saikosaponin d inhibit proliferation and migratory activity of rat HSC-T6 cells. J Med Food. 2013 Sep;16(9):793-800. doi: 10.1089/jmf.2013.2762. PubMed PMID: 24044489; PubMed Central PMCID: PMC3778952. 9: Yoon SS, Seo JW, Ann SH, Kim HY, Kim HS, Cho HY, Yun J, Chung EY, Koo JS, Yang CH. Effects of saikosaponin A on cocaine self-administration in rats. Neurosci Lett. 2013 Oct 25;555:198-202. doi: 10.1016/j.neulet.2013.09.029. Epub 2013 Sep 26. PubMed PMID: 24076136. 10: Kim SO, Park JY, Jeon SY, Yang CH, Kim MR. Saikosaponin a, an active compound of Radix Bupleuri, attenuates inflammation in hypertrophied 3T3-L1 adipocytes via ERK/NF-κB signaling pathways. Int J Mol Med. 2015 Apr;35(4):1126-32. doi: 10.3892/ijmm.2015.2093. Epub 2015 Feb 6. PubMed PMID: 25672367. 11: Fu Y, Hu X, Cao Y, Zhang Z, Zhang N. Saikosaponin a inhibits lipopolysaccharide-oxidative stress and inflammation in Human umbilical vein endothelial cells via preventing TLR4 translocation into lipid rafts. Free Radic Biol Med. 2015 Dec;89:777-85. doi: 10.1016/j.freeradbiomed.2015.10.407. Epub 2015 Oct 22. PubMed PMID: 26475038. 12: Wu Z, Du M, Shi X, Xu B, Qiao Y. Robust PLS Prediction Model for Saikosaponin A in Bupleurum chinense DC. Coupled with Granularity-Hybrid Calibration Set. J Anal Methods Chem. 2015;2015:583841. doi: 10.1155/2015/583841. Epub 2015 Mar 2. PubMed PMID: 25821634; PubMed Central PMCID: PMC4363675. 13: Liu G, Tian Y, Li G, Xu L, Song R, Zhang Z. Metabolism of saikosaponin a in rats: diverse oxidations on the aglycone moiety in liver and intestine in addition to hydrolysis of glycosidic bonds. Drug Metab Dispos. 2013 Mar;41(3):622-33. doi: 10.1124/dmd.112.048975. Epub 2012 Dec 31. PubMed PMID: 23277344. 14: Wang X, Wang Q, Burczynski FJ, Kong W, Gong Y. Saikosaponin A of Bupleurum chinense (Chaihu) elevates bone morphogenetic protein 4 (BMP-4) during hepatic stellate cell activation. Phytomedicine. 2013 Nov 15;20(14):1330-5. doi: 10.1016/j.phymed.2013.07.010. Epub 2013 Aug 19. PubMed PMID: 23969230. 15: Li J, Xu Q, Jiang H. Identification and Characterization of Two New Degradation Products of Saikosaponin A under Acid Hydrolytic Conditions. Molecules. 2016 Sep 14;21(9). pii: E1232. doi: 10.3390/molecules21091232. PubMed PMID: 27649123. 16: Wu SJ, Tam KW, Tsai YH, Chang CC, Chao JC. Curcumin and saikosaponin a inhibit chemical-induced liver inflammation and fibrosis in rats. Am J Chin Med. 2010;38(1):99-111. PubMed PMID: 20128048. 17: Lee TH, Park S, You MH, Lim JH, Min SH, Kim BM. A potential therapeutic effect of saikosaponin C as a novel dual-target anti-Alzheimer agent. J Neurochem. 2016 Mar;136(6):1232-1245. doi: 10.1111/jnc.13515. Epub 2016 Jan 21. PubMed PMID: 26710244. 18: Lin LT, Chung CY, Hsu WC, Chang SP, Hung TC, Shields J, Russell RS, Lin CC, Li CF, Yen MH, Tyrrell DL, Lin CC, Richardson CD. Saikosaponin b2 is a naturally occurring terpenoid that efficiently inhibits hepatitis C virus entry. J Hepatol. 2015 Mar;62(3):541-8. doi: 10.1016/j.jhep.2014.10.040. Epub 2014 Nov 4. Erratum in: J Hepatol. 2015 Jul;63(1):292. PubMed PMID: 25450204. 19: Li ZY, Jiang YM, Liu YM, Guo Z, Shen SN, Liu XM, Pan RL. Saikosaponin D acts against corticosterone-induced apoptosis via regulation of mitochondrial GR translocation and a GR-dependent pathway. Prog Neuropsychopharmacol Biol Psychiatry. 2014 Aug 4;53:80-9. doi: 10.1016/j.pnpbp.2014.02.010. Epub 2014 Mar 15. PubMed PMID: 24636912. 20: Zhu J, Luo C, Wang P, He Q, Zhou J, Peng H. Saikosaponin A mediates the inflammatory response by inhibiting the MAPK and NF-κB pathways in LPS-stimulated RAW 264.7 cells. Exp Ther Med. 2013 May;5(5):1345-1350. Epub 2013 Mar 4. PubMed PMID: 23737876; PubMed Central PMCID: PMC3671791.