Withanone | CAS#27570-38-3 | anticancer

MedKoo Cat#: 585432 | Name: Withanone

Description:

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

Withanone combined with Cucurbitacin B has selective toxicity to cancer cells.

Chemical Structure

Withanone

CAS#27570-38-3

Theoretical Analysis

MedKoo Cat#: 585432

Name: Withanone

CAS#: 27570-38-3

Chemical Formula: C28H38O6

Exact Mass: 470.2668

Molecular Weight: 470.61

Elemental Analysis: C, 71.46; H, 8.14; O, 20.40

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Synonym

Withanone; NSC 179884; NSC-179884; NSC179884;

IUPAC/Chemical Name

(1S,2S,4S,5R,10R,11S,14S,15S,18S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-5,15-dihydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadec-7-en-9-one

InChi Key

FAZIYUIDUNHZRG-PCTWTJKKSA-N

InChi Code

InChI=1S/C28H38O6/c1-14-13-19(33-24(30)15(14)2)16(3)27(31)12-9-17-21-18(8-11-25(17,27)4)26(5)20(29)7-6-10-28(26,32)23-22(21)34-23/h6-7,16-19,21-23,31-32H,8-13H2,1-5H3/t16-,17+,18+,19-,21+,22+,23+,25+,26+,27+,28+/m1/s1

SMILES Code

O=C1C=CC[C@]2(O)[C@@]3([H])O[C@@]3([H])[C@@]4([H])[C@]5([H])CC[C@](O)([C@@H]([C@H]6CC(C)=C(C)C(O6)=O)C)[C@@]5(C)CC[C@]4([H])[C@@]12C

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 470.61 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: Chaudhary A, Kalra RS, Malik V, Katiyar SP, Sundar D, Kaul SC, Wadhwa R. 2, 3-Dihydro-3β-methoxy Withaferin-A Lacks Anti-Metastasis Potency: Bioinformatics and Experimental Evidences. Sci Rep. 2019 Nov 22;9(1):17344. doi: 10.1038/s41598-019-53568-6. PubMed PMID: 31757995; PubMed Central PMCID: PMC6874665. 2: Tomar V, Beuerle T, Sircar D. A validated HPTLC method for the simultaneous quantifications of three phenolic acids and three withanolides from Withania somnifera plants and its herbal products. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Aug 15;1124:154-160. doi: 10.1016/j.jchromb.2019.06.009. Epub 2019 Jun 6. PubMed PMID: 31200247. 3: Garg S, Huifu H, Kumari A, Sundar D, Kaul SC, Wadhwa R. Induction of Senescence in Cancer Cells by a Novel Combination of Cucurbitacin B and Withanone: Molecular Mechanism and Therapeutic Potential. J Gerontol A Biol Sci Med Sci. 2019 May 21. pii: glz077. doi: 10.1093/gerona/glz077. [Epub ahead of print] PubMed PMID: 31112603. 4: Garg S, Kaul SC, Wadhwa R. Anti-Stress and Glial Differentiation Effects of a Novel Combination of Cucurbitacin B and Withanone (CucWi-N): Experimental Evidence. Ann Neurosci. 2018 Dec;25(4):201-209. doi: 10.1159/000490693. Epub 2018 Jul 5. PubMed PMID: 31000958; PubMed Central PMCID: PMC6470339. 5: Rath SN, Jena L, Patri M. Understanding ligands driven mechanism of wild and mutant aryl hydrocarbon receptor in presence of phytochemicals combating Parkinson's disease: an in silico and in vivo study. J Biomol Struct Dyn. 2019 Mar 5:1-20. doi: 10.1080/07391102.2019.1590240. [Epub ahead of print] PubMed PMID: 30836878. 6: Sundar D, Yu Y, Katiyar SP, Putri JF, Dhanjal JK, Wang J, Sari AN, Kolettas E, Kaul SC, Wadhwa R. Wild type p53 function in p53(Y220C) mutant harboring cells by treatment with Ashwagandha derived anticancer withanolides: bioinformatics and experimental evidence. J Exp Clin Cancer Res. 2019 Feb 26;38(1):103. doi: 10.1186/s13046-019-1099-x. PubMed PMID: 30808373; PubMed Central PMCID: PMC6390572. 7: Kim S, Yu JS, Lee JY, Choi SU, Lee J, Kim KH. Cytotoxic Withanolides from the Roots of Indian Ginseng ( Withania somnifera). J Nat Prod. 2019 Apr 26;82(4):765-773. doi: 10.1021/acs.jnatprod.8b00665. Epub 2019 Feb 18. PubMed PMID: 30776236. 8: Borah K, Sharma S, Silla Y. Structural bioinformatics-based identification of putative plant based lead compounds for Alzheimer Disease Therapy. Comput Biol Chem. 2019 Feb;78:359-366. doi: 10.1016/j.compbiolchem.2018.12.012. Epub 2019 Jan 8. PubMed PMID: 30677568. 9: Kaur A, Singh B, Ohri P, Wang J, Wadhwa R, Kaul SC, Pati PK, Kaur A. Organic cultivation of Ashwagandha with improved biomass and high content of active Withanolides: Use of Vermicompost. PLoS One. 2018 Apr 16;13(4):e0194314. doi: 10.1371/journal.pone.0194314. eCollection 2018. PubMed PMID: 29659590; PubMed Central PMCID: PMC5901777. 10: Pandey A, Bani S, Dutt P, Kumar Satti N, Avtar Suri K, Nabi Qazi G. Multifunctional neuroprotective effect of Withanone, a compound from Withania somnifera roots in alleviating cognitive dysfunction. Cytokine. 2018 Feb;102:211-221. doi: 10.1016/j.cyto.2017.10.019. Epub 2017 Nov 3. PubMed PMID: 29108796. 11: Yaseen Malik M, Taneja I, Raju KSR, Rahaman Gayen J, Singh SP, Sangwand NS, Wahajuddin M. RP-HPLC Separation of Isomeric Withanolides: Method Development, Validation and Application to In situ Rat Permeability Determination. J Chromatogr Sci. 2017 Aug 1;55(7):729-735. doi: 10.1093/chromsci/bmx027. Review. PubMed PMID: 28407087. 12: Ahlawat S, Saxena P, Ali A, Khan S, Abdin MZ. Comparative study of withanolide production and the related transcriptional responses of biosynthetic genes in fungi elicited cell suspension culture of Withania somnifera in shake flask and bioreactor. Plant Physiol Biochem. 2017 May;114:19-28. doi: 10.1016/j.plaphy.2017.02.013. Epub 2017 Feb 17. PubMed PMID: 28249222. 13: Kaul SC, Ishida Y, Tamura K, Wada T, Iitsuka T, Garg S, Kim M, Gao R, Nakai S, Okamoto Y, Terao K, Wadhwa R. Novel Methods to Generate Active Ingredients-Enriched Ashwagandha Leaves and Extracts. PLoS One. 2016 Dec 9;11(12):e0166945. doi: 10.1371/journal.pone.0166945. eCollection 2016. PubMed PMID: 27936030; PubMed Central PMCID: PMC5147857. 14: Purushotham PM, Kim JM, Jo EK, Senthil K. Withanolides against TLR4-Activated Innate Inflammatory Signalling Pathways: A Comparative Computational and Experimental Study. Phytother Res. 2017 Jan;31(1):152-163. doi: 10.1002/ptr.5746. Epub 2016 Nov 17. PubMed PMID: 27859734. 15: Singh V, Singh B, Sharma A, Kaur K, Gupta AP, Salar RK, Hallan V, Pati PK. Leaf spot disease adversely affects human health-promoting constituents and withanolide biosynthesis in Withania somnifera (L.) Dunal. J Appl Microbiol. 2017 Jan;122(1):153-165. doi: 10.1111/jam.13314. Epub 2016 Nov 15. PubMed PMID: 27709727. 16: Gupta M, Kaur G. Aqueous extract from the Withania somnifera leaves as a potential anti-neuroinflammatory agent: a mechanistic study. J Neuroinflammation. 2016 Aug 22;13(1):193. doi: 10.1186/s12974-016-0650-3. PubMed PMID: 27550017; PubMed Central PMCID: PMC4994385. 17: Dar NJ, Bhat JA, Satti NK, Sharma PR, Hamid A, Ahmad M. Withanone, an Active Constituent from Withania somnifera, Affords Protection Against NMDA-Induced Excitotoxicity in Neuron-Like Cells. Mol Neurobiol. 2017 Sep;54(7):5061-5073. doi: 10.1007/s12035-016-0044-7. Epub 2016 Aug 19. PubMed PMID: 27541286. 18: Devkar ST, Kandhare AD, Sloley BD, Jagtap SD, Lin J, Tam YK, Katyare SS, Bodhankar SL, Hegde MV. Evaluation of the bioavailability of major withanolides of Withania somnifera using an in vitro absorption model system. J Adv Pharm Technol Res. 2015 Oct-Dec;6(4):159-64. doi: 10.4103/2231-4040.165023. PubMed PMID: 26605156; PubMed Central PMCID: PMC4630722. 19: Saema S, Rahman LU, Singh R, Niranjan A, Ahmad IZ, Misra P. Ectopic overexpression of WsSGTL1, a sterol glucosyltransferase gene in Withania somnifera, promotes growth, enhances glycowithanolide and provides tolerance to abiotic and biotic stresses. Plant Cell Rep. 2016 Jan;35(1):195-211. doi: 10.1007/s00299-015-1879-5. Epub 2015 Oct 30. PubMed PMID: 26518426. 20: Kataria H, Gupta M, Lakhman S, Kaur G. Withania somnifera aqueous extract facilitates the expression and release of GnRH: In vitro and in vivo study. Neurochem Int. 2015 Oct;89:111-9. doi: 10.1016/j.neuint.2015.08.001. Epub 2015 Aug 6. PubMed PMID: 26257126.