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MedKoo Cat#: 540188 | Name: Guggulsterone
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Description:

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

Guggulsterone is a FXR antagonist found in myrrh. It displays a wide variety of biological activities, including disrupting cytoskeletal organization, inhibiting doxorubicin-induced toxicity in cardiomyoc

Chemical Structure

Guggulsterone
Guggulsterone
CAS# 95975-55-6

Theoretical Analysis

MedKoo Cat#: 540188

Name: Guggulsterone

CAS#: 95975-55-6

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
Guggulsterone; Z/E-Guggulsterone
IUPAC/Chemical Name
(8R,9S,10R,13S,14S,Z)-17-ethylidene-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,17-dodecahydro-3H-cyclopenta[a]phenanthrene-3,16(2H)-dione
InChi Key
WDXRGPWQVHZTQJ-OSJVMJFVSA-N
InChi Code
InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1
SMILES Code
O=C(C=C1CC[C@@]2([H])[C@]3([H])CC/4=O)CC[C@]1(C)[C@@]2([H])CC[C@]3(C)C4=C\C
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
>2 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Guggulsterone, a farnesoid X receptor (FXR) antagonist, decreases CDCA-induced FXR activation with IC50s of 17 and 15 μM for Z- and E-Guggulsterone, respectively.
In vitro activity:
The results revealed that Z-guggulsterone dose-dependently inhibited the colony-forming potential of Huh7 cells (Figure 8a). This study observed that Z-guggulsterone at IC30 reduced the growth of colonies by more than 20%, while the treatment with Z-guggulsterone at IC40 decreased the colony formation by more than 47%, in comparison with the control group. When the cells were treated with IC50, the population density dropped to 19% of that of control cells (Figure 8b). These results for the cell cycle analysis showed that Z-guggulsterone dose-dependently modulated Huh7 cell cycle progression through a G0/G1 phase increase combined with G2/M depletion (Figure 9). Reference: Molecules. 2022 Aug 11;27(16):5104. https://pubmed.ncbi.nlm.nih.gov/36014345/
In vivo activity:
Z-guggulsterone can relieve neurological pain in CCI mice, which may be related to the inhibition of astrocytes and proinflammatory cytokines in the spinal dorsal horn. Reference: J Pain Res. 2022 May 5;15:1315-1324. https://pubmed.ncbi.nlm.nih.gov/35546904/
Solvent mg/mL mM
Solubility
DMSO 41.4 132.55
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 312.45 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.

Recalculate based on batch purity %
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. Gupta M, Ghufran SM, Kausar T, Ali R, Biswas S, Nayeem SM, Ishrat R, Ali S, Ahmad A, Rather IA, Sarwat M. Z-Guggulsterone Is a Potential Lead Molecule of Dawa-ul-Kurkum against Hepatocellular Carcinoma. Molecules. 2022 Aug 11;27(16):5104. doi: 10.3390/molecules27165104. PMID: 36014345; PMCID: PMC9413334. 2. Lv R, Zhu M, Chen K, Xie H, Bai H, Chen Q. Z-Guggulsterone Induces Apoptosis in Gastric Cancer Cells through the Intrinsic Mitochondria-Dependent Pathway. ScientificWorldJournal. 2021 Jan 4;2021:3152304. doi: 10.1155/2021/3152304. PMID: 33488300; PMCID: PMC7801056. 3. Dang SJ, Wei WB, Li RL, Song CX, Xu J. Z-Guggulsterone Relieves Neuropathic Pain by Inhibiting the Expression of Astrocytes and Proinflammatory Cytokines in the Spinal Dorsal Horn. J Pain Res. 2022 May 5;15:1315-1324. doi: 10.2147/JPR.S360126. PMID: 35546904; PMCID: PMC9084390. 4. Khera R, Mehan S, Bhalla S, Kumar S, Alshammari A, Alharbi M, Sadhu SS. Guggulsterone Mediated JAK/STAT and PPAR-Gamma Modulation Prevents Neurobehavioral and Neurochemical Abnormalities in Propionic Acid-Induced Experimental Model of Autism. Molecules. 2022 Jan 28;27(3):889. doi: 10.3390/molecules27030889. PMID: 35164154; PMCID: PMC8839522.
In vitro protocol:
1. Gupta M, Ghufran SM, Kausar T, Ali R, Biswas S, Nayeem SM, Ishrat R, Ali S, Ahmad A, Rather IA, Sarwat M. Z-Guggulsterone Is a Potential Lead Molecule of Dawa-ul-Kurkum against Hepatocellular Carcinoma. Molecules. 2022 Aug 11;27(16):5104. doi: 10.3390/molecules27165104. PMID: 36014345; PMCID: PMC9413334. 2. Lv R, Zhu M, Chen K, Xie H, Bai H, Chen Q. Z-Guggulsterone Induces Apoptosis in Gastric Cancer Cells through the Intrinsic Mitochondria-Dependent Pathway. ScientificWorldJournal. 2021 Jan 4;2021:3152304. doi: 10.1155/2021/3152304. PMID: 33488300; PMCID: PMC7801056.
In vivo protocol:
1. Dang SJ, Wei WB, Li RL, Song CX, Xu J. Z-Guggulsterone Relieves Neuropathic Pain by Inhibiting the Expression of Astrocytes and Proinflammatory Cytokines in the Spinal Dorsal Horn. J Pain Res. 2022 May 5;15:1315-1324. doi: 10.2147/JPR.S360126. PMID: 35546904; PMCID: PMC9084390. 2. Khera R, Mehan S, Bhalla S, Kumar S, Alshammari A, Alharbi M, Sadhu SS. Guggulsterone Mediated JAK/STAT and PPAR-Gamma Modulation Prevents Neurobehavioral and Neurochemical Abnormalities in Propionic Acid-Induced Experimental Model of Autism. Molecules. 2022 Jan 28;27(3):889. doi: 10.3390/molecules27030889. PMID: 35164154; PMCID: PMC8839522.
1: Shi JJ, Jia XL, Li M, Yang N, Li YP, Zhang X, Gao N, Dang SS. Guggulsterone induces apoptosis of human hepatocellular carcinoma cells through intrinsic mitochondrial pathway. World J Gastroenterol. 2015 Dec 21;21(47):13277-87. doi: 10.3748/wjg.v21.i47.13277. PubMed PMID: 26715810; PubMed Central PMCID: PMC4679759. 2: Zhong F, Yang J, Tong ZT, Chen LL, Fan LL, Wang F, Zha XL, Li J. Guggulsterone inhibits human cholangiocarcinoma Sk-ChA-1 and Mz-ChA-1 cell growth by inducing caspase-dependent apoptosis and downregulation of survivin and Bcl-2 expression. Oncol Lett. 2015 Sep;10(3):1416-1422. Epub 2015 Jun 19. PubMed PMID: 26622683; PubMed Central PMCID: PMC4533301. 3: Shishodia S, Azu N, Rosenzweig JA, Jackson DA. Guggulsterone for Chemoprevention of Cancer. Curr Pharm Des. 2016;22(3):294-306. Review. PubMed PMID: 26561056. 4: Kulhari A, Sheorayan A, Chaudhury A, Sarkar S, Kalia RK. Quantitative determination of guggulsterone in existing natural populations of Commiphora wightii (Arn.) Bhandari for identification of germplasm having higher guggulsterone content. Physiol Mol Biol Plants. 2015 Jan;21(1):71-81. doi: 10.1007/s12298-014-0271-1. Epub 2014 Nov 22. PubMed PMID: 25648764; PubMed Central PMCID: PMC4312330. 5: Xu HB, Xu LZ, Mao XP, Fu J. Guggulsterone of Commiphora mukul resin reverses drug resistance in imatinib-resistant leukemic cells by inhibiting cyclooxygenase-2 and P-glycoprotein. Phytomedicine. 2014 Jun 15;21(7):1004-9. doi: 10.1016/j.phymed.2014.02.014. Epub 2014 Mar 26. PubMed PMID: 24680616. 6: Yamada T, Sugimoto K. Guggulsterone and Its Role in Chronic Diseases. Adv Exp Med Biol. 2016;929:329-361. PubMed PMID: 27771932. 7: Huang C, Wang J, Lu X, Hu W, Wu F, Jiang B, Ling Y, Yang R, Zhang W. Z-guggulsterone negatively controls microglia-mediated neuroinflammation via blocking IκB-α-NF-κB signals. Neurosci Lett. 2016 Apr 21;619:34-42. doi: 10.1016/j.neulet.2016.02.021. Epub 2016 Feb 12. PubMed PMID: 26879835. 8: Mithila MV, Khanum F. The appetite regulatory effect of guggulsterones in rats: a repertoire of plasma hormones and neurotransmitters. J Diet Suppl. 2014 Sep;11(3):262-71. doi: 10.3109/19390211.2014.937045. Epub 2014 Jul 15. PubMed PMID: 25025986. 9: Xu HB, Shen ZL, Fu J, Xu LZ. Reversal of doxorubicin resistance by guggulsterone of Commiphora mukul in vivo. Phytomedicine. 2014 Sep 25;21(11):1221-9. doi: 10.1016/j.phymed.2014.06.003. Epub 2014 Jul 25. PubMed PMID: 25172783. 10: Noh EM, Chung EY, Youn HJ, Jung SH, Hur H, Lee YR, Kim JS. Cis-guggulsterone inhibits the IKK/NF-κB pathway, whereas trans-guggulsterone inhibits MAPK/AP-1 in MCF 7 breast cancer cells: guggulsterone regulates MMP 9 expression in an isomer-specific manner. Int J Mol Med. 2013 Feb;31(2):393-9. doi: 10.3892/ijmm.2012.1214. Epub 2012 Dec 14. PubMed PMID: 23242121. 11: Chen XZ, Xu HB, Xu LZ, Mao XP, Li L. Guggulsterone regulates the function and expression of P-glycoprotein in rat brain microvessel endothelial cells. Eur J Pharmacol. 2013 Oct 15;718(1-3):24-9. doi: 10.1016/j.ejphar.2013.09.010. Epub 2013 Sep 13. PubMed PMID: 24041929. 12: Pal P, Kanaujiya JK, Lochab S, Tripathi SB, Sanyal S, Behre G, Trivedi AK. Proteomic analysis of rosiglitazone and guggulsterone treated 3T3-L1 preadipocytes. Mol Cell Biochem. 2013 Apr;376(1-2):81-93. doi: 10.1007/s11010-012-1551-0. Epub 2012 Dec 30. PubMed PMID: 23275126. 13: Zhong F, Tong ZT, Fan LL, Zha LX, Wang F, Yao MQ, Gu KS, Cao YX. Guggulsterone-induced apoptosis in cholangiocarcinoma cells through ROS/JNK signaling pathway. Am J Cancer Res. 2016 Jan 15;6(2):226-37. eCollection 2016. PubMed PMID: 27186398; PubMed Central PMCID: PMC4859655. 14: Kim BH, Yoon JH, Yang JI, Myung SJ, Lee JH, Jung EU, Yu SJ, Kim YJ, Lee HS, Kim CY. Guggulsterone attenuates activation and survival of hepatic stellate cell by inhibiting nuclear factor kappa B activation and inducing apoptosis. J Gastroenterol Hepatol. 2013 Dec;28(12):1859-68. doi: 10.1111/jgh.12314. PubMed PMID: 23808824. 15: Chen Z, Huang C, Ding W. Z-Guggulsterone Improves the Scopolamine-Induced Memory Impairments Through Enhancement of the BDNF Signal in C57BL/6J Mice. Neurochem Res. 2016 Dec;41(12):3322-3332. Epub 2016 Sep 28. PubMed PMID: 27677871. 16: Agrawal P, Vegda R, Laddha K. Simultaneous Estimation of Withaferin A and Z-Guggulsterone in Marketed Formulation by RP-HPLC. J Chromatogr Sci. 2015 Jul;53(6):940-4. doi: 10.1093/chromsci/bmu153. Epub 2015 Jan 8. PubMed PMID: 25572656. 17: Kong JN, He Q, Wang G, Dasgupta S, Dinkins MB, Zhu G, Kim A, Spassieva S, Bieberich E. Guggulsterone and bexarotene induce secretion of exosome-associated breast cancer resistance protein and reduce doxorubicin resistance in MDA-MB-231 cells. Int J Cancer. 2015 Oct 1;137(7):1610-20. doi: 10.1002/ijc.29542. Epub 2015 Apr 27. PubMed PMID: 25833198; PubMed Central PMCID: PMC4503537. 18: Xu HB, Yu J, Xu LZ, Fu J. Regulation of P-glycoprotein efflux activity by Z-guggulsterone of Commiphora mukul at the blood-brain barrier. J Neurol Sci. 2016 Apr 15;363:147-52. doi: 10.1016/j.jns.2016.02.046. Epub 2016 Feb 20. PubMed PMID: 27000241. 19: Dixit D, Ghildiyal R, Anto NP, Ghosh S, Sharma V, Sen E. Guggulsterone sensitizes glioblastoma cells to Sonic hedgehog inhibitor SANT-1 induced apoptosis in a Ras/NFκB dependent manner. Cancer Lett. 2013 Aug 19;336(2):347-58. doi: 10.1016/j.canlet.2013.03.025. Epub 2013 Mar 31. PubMed PMID: 23548480. 20: Kim DG, Bae GS, Choi SB, Jo IJ, Shin JY, Lee SK, Kim MJ, Kim MJ, Jeong HW, Choi CM, Seo SH, Choo GC, Seo SW, Song HJ, Park SJ. Guggulsterone attenuates cerulein-induced acute pancreatitis via inhibition of ERK and JNK activation. Int Immunopharmacol. 2015 May;26(1):194-202. doi: 10.1016/j.intimp.2015.03.030. Epub 2015 Apr 2. PubMed PMID: 25843255.