Isosteviol | CAS#27975-19-5 | ERK inhibitor

MedKoo Cat#: 330143 | Name: Isosteviol

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Description:

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

Isosteviol is an antihyperglycemic agent; obtained by acid hydrolysis of stevioside. Isosteviol ameliorates diabetic cardiomyopathy in rats by inhibiting ERK and NF-κB signaling pathways. Isosteviol Inhibits Astrogliosis after Cerebral Ischemia/Reperfusion Injury in Rats.

Chemical Structure

Isosteviol

CAS#27975-19-5 (free acid)

Theoretical Analysis

MedKoo Cat#: 330143

Name: Isosteviol

CAS#: 27975-19-5 (free acid)

Chemical Formula: C20H30O3

Exact Mass: 318.2195

Molecular Weight: 318.46

Elemental Analysis: C, 75.43; H, 9.50; O, 15.07

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 285.00

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Related CAS #

27975-19-5 (free acid) 1160958-41-7 (sodium)

Synonym

Isosteviol, NSC 231875; NSC-231875; NSC231875; (−)-Isosteviol.

IUPAC/Chemical Name

(4R,4aS,6aS,9S,11aR,11bR)-4,9,11b-trimethyl-8-oxotetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid

InChi Key

KFVUFODCZDRVSS-LLTUXKBDSA-N

InChi Code

InChI=1S/C20H30O3/c1-17-9-5-14-18(2)7-4-8-19(3,16(22)23)13(18)6-10-20(14,12-17)11-15(17)21/h13-14H,4-12H2,1-3H3,(H,22,23)/t13-,14-,17-,18-,19+,20+/m0/s1

SMILES Code

C[C@]1(C2)C(C[C@@]2(CC[C@H]3[C@]4(C)CCC[C@]3(C(O)=O)C)[C@H]4CC1)=O

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Isosteviol inhibits DNA polymerase and DNA topoisomerase and has antibacterial, anticancer and anti-tuberculosis effects.

In vitro activity:

Indeed, this study could detect a trend towards reduced IL-6 expression in our murine microvascular cerebellar endothelial cells cerebEND upon administration of STVNA (isosteviol sodium) post-OGD in comparison to the control. The same effect was shown by 100 nmol dexamethasone, a known potent anti-inflammatory therapeutic agent. Likewise, the combination of 10/20/30 mg/L STVNA + 100 nmol dexamethasone exhibited a decreased IL-6 level (Figure 1). Reference: Pharmaceutics. 2022 Aug 23;14(9):1753. https://pubmed.ncbi.nlm.nih.gov/36145501/

In vivo activity:

STVNa (isosteviol sodium) attenuated abnormal BW gain and decreased the ratio of LW:BW in HFD-fed rats, indicating that STVNa could be used to treat NAFLD (Fig. 2A,B). With respect to the changes in lipid metabolism, the high contents of TC and TG were decreased by STVNa in HFD-fed rats (Fig. 2G). Similarly, the high levels of AST and ALT were attenuated by STVNa treatment (Fig. 2F). In addition, STVNa treatment obviously decreased the areas of NAFLD as well as the numbers of infiltrating inflammatory cell clusters and ballooning hepatocytes, thus partially reversing the morphological alterations in the liver tissues of NAFLD rats (Fig. 2C–E). Reference: Sci Rep. 2022 Jul 27;12(1):12857. https://pubmed.ncbi.nlm.nih.gov/35896572/

	Solvent	mg/mL	mM
Solubility
	DMSO	81.5	255.92

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 318.46 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. Reschke M, Salvador E, Schlegel N, Burek M, Karnati S, Wunder C, Förster CY. Isosteviol Sodium (STVNA) Reduces Pro-Inflammatory Cytokine IL-6 and GM-CSF in an In Vitro Murine Stroke Model of the Blood-Brain Barrier (BBB). Pharmaceutics. 2022 Aug 23;14(9):1753. doi: 10.3390/pharmaceutics14091753. PMID: 36145501; PMCID: PMC9505783. 2. Rösing N, Salvador E, Güntzel P, Kempe C, Burek M, Holzgrabe U, Soukhoroukov V, Wunder C, Förster C. Neuroprotective Effects of Isosteviol Sodium in Murine Brain Capillary Cerebellar Endothelial Cells (cerebEND) After Hypoxia. Front Cell Neurosci. 2020 Oct 28;14:573950. doi: 10.3389/fncel.2020.573950. PMID: 33192319; PMCID: PMC7655651. 3. Mei Y, Hu H, Deng L, Sun X, Tan W. Therapeutic effects of isosteviol sodium on non-alcoholic fatty liver disease by regulating autophagy via Sirt1/AMPK pathway. Sci Rep. 2022 Jul 27;12(1):12857. doi: 10.1038/s41598-022-16119-0. PMID: 35896572; PMCID: PMC9329321. 4. Wang S, Huang J, Tan KS, Deng L, Liu F, Tan W. Isosteviol Sodium Ameliorates Dextran Sodium Sulfate-Induced Chronic Colitis through the Regulation of Metabolic Profiling, Macrophage Polarization, and NF-κB Pathway. Oxid Med Cell Longev. 2022 Jan 27;2022:4636618. doi: 10.1155/2022/4636618. PMID: 35126813; PMCID: PMC8813272.

In vitro protocol:

In vivo protocol:

1. Mei Y, Hu H, Deng L, Sun X, Tan W. Therapeutic effects of isosteviol sodium on non-alcoholic fatty liver disease by regulating autophagy via Sirt1/AMPK pathway. Sci Rep. 2022 Jul 27;12(1):12857. doi: 10.1038/s41598-022-16119-0. PMID: 35896572; PMCID: PMC9329321. 2. Wang S, Huang J, Tan KS, Deng L, Liu F, Tan W. Isosteviol Sodium Ameliorates Dextran Sodium Sulfate-Induced Chronic Colitis through the Regulation of Metabolic Profiling, Macrophage Polarization, and NF-κB Pathway. Oxid Med Cell Longev. 2022 Jan 27;2022:4636618. doi: 10.1155/2022/4636618. PMID: 35126813; PMCID: PMC8813272.

1: Zhang H, Zan J, Zhong K, Lu M, Sun X, Tan W. Neuroprotective Effects of Isosteviol Sodium through Increasing CYLD by the Downregulation miRNA-181b. Brain Res Bull. 2018 May 25. pii: S0361-9230(18)30108-4. doi: 10.1016/j.brainresbull.2018.05.015. [Epub ahead of print] PubMed PMID: 29807144. 2: Yang Y, Zhong Q, Zhang H, Mo C, Yao J, Huang T, Zhou T, Tan W. Lipidomics study of the protective effects of isosteviol sodium on stroke rats using ultra high-performance supercritical fluid chromatography coupling with ion-trap and time-of-flight tandem mass spectrometry. J Pharm Biomed Anal. 2018 Aug 5;157:145-155. doi: 10.1016/j.jpba.2018.05.022. Epub 2018 May 17. PubMed PMID: 29800902. 3: Tang SG, Liu XY, Ye JM, Hu TT, Yang YY, Han T, Tan W. Isosteviol ameliorates diabetic cardiomyopathy in rats by inhibiting ERK and NF-κB signaling pathways. J Endocrinol. 2018 Jul;238(1):47-60. doi: 10.1530/JOE-17-0681. Epub 2018 May 2. PubMed PMID: 29720537. 4: Kachingwe BH, Wang LH, Uang YS, Huang TJ, Lin SJ. Dose-dependent pharmacokinetics and tentative identification of urine metabolites from an isosteviol derivative with anti-hepatitis B activity in rats. Biomed Chromatogr. 2018 Apr 24:e4266. doi: 10.1002/bmc.4266. [Epub ahead of print] PubMed PMID: 29689637. 5: Zan J, Zhang H, Lu MY, Beng HM, Zhong KL, Sun XO, Tan W. Isosteviol sodium injection improves outcomes by modulating TLRs/NF-κB-dependent inflammatory responses following experimental traumatic brain injury in rats. Neuroreport. 2018 Jul 4;29(10):794-803. doi: 10.1097/WNR.0000000000001033. PubMed PMID: 29683870; PubMed Central PMCID: PMC5999382. 6: Zhang H, Sun X, Xie Y, Tian F, Hu H, Tan W. Isosteviol Sodium Inhibits Astrogliosis after Cerebral Ischemia/Reperfusion Injury in Rats. Biol Pharm Bull. 2018;41(4):575-584. doi: 10.1248/bpb.b17-00921. PubMed PMID: 29607930. 7: Sun X, Yang Y, Xie Y, Shi X, Huang L, Tan W. Protective role of STVNa in myocardial ischemia reperfusion injury by inhibiting mitochondrial fission. Oncotarget. 2017 Dec 5;9(2):1898-1905. doi: 10.18632/oncotarget.22969. eCollection 2018 Jan 5. PubMed PMID: 29416739; PubMed Central PMCID: PMC5788607. 8: Kachingwe BH, Uang YS, Huang TJ, Wang LH, Lin SJ. Development and validation of an LC-MS/MS method for quantification of NC-8 in rat plasma and its application to pharmacokinetic studies. J Food Drug Anal. 2018 Jan;26(1):401-408. doi: 10.1016/j.jfda.2017.09.003. Epub 2017 Nov 11. PubMed PMID: 29389580. 9: Gu W, Rebsdorf A, Hermansen K, Gregersen S, Jeppesen PB. The Dynamic Effects of Isosteviol on Insulin Secretion and Its Inability to Counteract the Impaired β-Cell Function during Gluco-, Lipo-, and Aminoacidotoxicity: Studies In Vitro. Nutrients. 2018 Jan 26;10(2). pii: E127. doi: 10.3390/nu10020127. PubMed PMID: 29373526; PubMed Central PMCID: PMC5852703. 10: Testai L, Strobykina I, Semenov VV, Semenova M, Pozzo ED, Martelli A, Citi V, Martini C, Breschi MC, Kataev VE, Calderone V. Mitochondriotropic and Cardioprotective Effects of Triphenylphosphonium-Conjugated Derivatives of the Diterpenoid Isosteviol. Int J Mol Sci. 2017 Sep 26;18(10). pii: E2060. doi: 10.3390/ijms18102060. PubMed PMID: 28954424; PubMed Central PMCID: PMC5666742. 11: Yin C, Chen Y, Wu H, Xu D, Tan W. Attenuation of ischemia/reperfusion-induced inhibition of the rapid component of delayed rectifier potassium current by Isosteviol through scavenging reactive oxygen species. Biochim Biophys Acta. 2017 Dec;1859(12):2447-2453. doi: 10.1016/j.bbamem.2017.09.003. Epub 2017 Sep 6. PubMed PMID: 28888367. 12: Yang Y, Zhong Q, Mo C, Zhang H, Zhou T, Tan W. Determination of endogenous inflammation-related lipid mediators in ischemic stroke rats using background subtracting calibration curves by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2017 Nov;409(28):6537-6547. doi: 10.1007/s00216-017-0600-7. Epub 2017 Sep 4. PubMed PMID: 28871447. 13: Zhang H, Sun X, Xie Y, Zan J, Tan W. Isosteviol Sodium Protects Against Permanent Cerebral Ischemia Injury in Mice via Inhibition of NF-κB-Mediated Inflammatory and Apoptotic Responses. J Stroke Cerebrovasc Dis. 2017 Nov;26(11):2603-2614. doi: 10.1016/j.jstrokecerebrovasdis.2017.06.023. Epub 2017 Aug 4. PubMed PMID: 28784277. 14: Wald JP, Morlock GE. Quantification of steviol glycosides in food products, Stevia leaves and formulations by planar chromatography, including proof of absence for steviol and isosteviol. J Chromatogr A. 2017 Jul 14;1506:109-119. doi: 10.1016/j.chroma.2017.05.026. Epub 2017 May 11. PubMed PMID: 28552425. 15: Fan Z, Lv N, Luo X, Tan W. Isosteviol prevents the prolongation of action potential in hypertrophied cardiomyoctyes by regulating transient outward potassium and L-type calcium channels. Biochim Biophys Acta. 2017 Oct;1859(10):1872-1879. doi: 10.1016/j.bbamem.2017.04.011. Epub 2017 Apr 18. PubMed PMID: 28428073. 16: Malki A, El-Sharkawy A, El Syaed M, Bergmeier S. Antitumor Activities of the Novel Isosteviol Derivative 10C Against Liver Cancer. Anticancer Res. 2017 Apr;37(4):1591-1601. PubMed PMID: 28373419. 17: Liu Y, Wang T, Ling Y, Bao N, Shi W, Chen L, Sun J. Design, synthesis and cytotoxic evaluation of nitric oxide-releasing derivatives of isosteviol. Chem Biol Drug Des. 2017 Sep;90(3):473-477. doi: 10.1111/cbdd.12956. Epub 2017 Feb 22. PubMed PMID: 28122177. 18: Liu CJ, Zhang T, Yu SL, Dai XJ, Wu Y, Tao JC. Synthesis, cytotoxic activity, and 2D- and 3D-QSAR studies of 19-carboxyl-modified novel isosteviol derivatives as potential anticancer agents. Chem Biol Drug Des. 2017 Jun;89(6):870-887. doi: 10.1111/cbdd.12910. Epub 2017 Feb 2. PubMed PMID: 27878967. 19: Momtazi-Borojeni AA, Esmaeili SA, Abdollahi E, Sahebkar A. A Review on the Pharmacology and Toxicology of Steviol Glycosides Extracted from Stevia rebaudiana. Curr Pharm Des. 2017;23(11):1616-1622. doi: 10.2174/1381612822666161021142835. Review. PubMed PMID: 27784241. 20: Liu CJ, Liu YP, Yu SL, Dai XJ, Zhang T, Tao JC. Syntheses, cytotoxic activity evaluation and HQSAR study of 1,2,3-triazole-linked isosteviol derivatives as potential anticancer agents. Bioorg Med Chem Lett. 2016 Nov 15;26(22):5455-5461. doi: 10.1016/j.bmcl.2016.10.028. Epub 2016 Oct 13. PubMed PMID: 27777008.