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MedKoo Cat#: 596272 | Name: Jolkinolide B

Description:

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

Jolkinolide B is a diterpenoid extracted from the roots of Euphorbia fischeriana Steud.

Chemical Structure

Jolkinolide B
Jolkinolide B
CAS#37905-08-1

Theoretical Analysis

MedKoo Cat#: 596272

Name: Jolkinolide B

CAS#: 37905-08-1

Chemical Formula: C20H26O4

Exact Mass: 330.1831

Molecular Weight: 330.42

Elemental Analysis: C, 72.70; H, 7.93; O, 19.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Jolkinolide B;
IUPAC/Chemical Name
(4aR,6aR,7aR,10aR,11aS,11bS,11cS)-4,4,8,11c-tetramethyl-1,2,3,4,4a,5,6,11a,11b,11c-decahydrobis(oxireno)[2',3':1,10a;2'',3'':3,4]phenanthro[3,2-b]furan-9(7aH)-one
InChi Key
SOVOCMGDFRGRKF-NURUDRBBSA-N
InChi Code
InChI=1S/C20H26O4/c1-10-12-14-19(22-14)9-6-11-17(2,3)7-5-8-18(11,4)13(19)15-20(12,23-15)24-16(10)21/h11,13-15H,5-9H2,1-4H3/t11-,13-,14-,15+,18+,19-,20-/m1/s1
SMILES Code
CC1=C([C@@H]2[C@@]3(O2)CC[C@@H]4C(C)(CCC[C@]4(C)[C@H]3[C@@H]5O6)C)[C@@]56OC1=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
>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

Preparing Stock Solutions

The following data is based on the product molecular weight 330.42 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
1: Mangisa M, Tembu VJ, Fouche G, Nthambeleni R, Peter X, Langat MK. Ent-abietane diterpenoids from Suregada zanzibariensis Baill. (Euphorbiaceae), their cytotoxic and anticancer properties. Nat Prod Res. 2018 May 9:1-8. doi: 10.1080/14786419.2018.1470628. [Epub ahead of print] PubMed PMID: 29741101. 2: Ma YL, Tang XH, Yuan WJ, Ding X, Di YT, Hao XJ. Abietane Diterpernoids from the Roots of Euphorbia ebracteolata. Nat Prod Bioprospect. 2018 Apr;8(2):131-135. doi: 10.1007/s13659-018-0159-9. Epub 2018 Mar 20. PubMed PMID: 29557523; PubMed Central PMCID: PMC5913052. 3: Dai CY, Tsai YS, Chou WW, Liu T, Huang CF, Wang SC, Tsai PC, Yeh ML, Hsieh MY, Huang CI, Vanson Liu SY, Huang JF, Chuang WL, Yu ML. The IL-6/STAT3 pathway upregulates microRNA-125b expression in hepatitis C virus infection. Oncotarget. 2018 Jan 10;9(13):11291-11302. doi: 10.18632/oncotarget.24129. eCollection 2018 Feb 16. PubMed PMID: 29541414; PubMed Central PMCID: PMC5834265. 4: Gao X, Han H. Jolkinolide B inhibits glycolysis by downregulating hexokinase 2 expression through inactivating the Akt/mTOR pathway in non-small cell lung cancer cells. J Cell Biochem. 2018 Jun;119(6):4967-4974. doi: 10.1002/jcb.26742. Epub 2018 Mar 9. PubMed PMID: 29384225. 5: Zhang J, Wang Y, Zhou Y, He QY. Jolkinolide B induces apoptosis of colorectal carcinoma through ROS-ER stress-Ca(2+)-mitochondria dependent pathway. Oncotarget. 2017 Aug 9;8(53):91223-91237. doi: 10.18632/oncotarget.20077. eCollection 2017 Oct 31. PubMed PMID: 29207638; PubMed Central PMCID: PMC5710918. 6: Cai D, Zhai W, Zhang Q, Liu J, Sun Y, Liu L, Liu J. Development of matrix solid-phase dispersion coupled with high-performance liquid chromatography for determination of jolkinolide A and jolkinolide B in Euphorbia fischeriana Steud. Nat Prod Res. 2017 Aug;31(15):1805-1811. doi: 10.1080/14786419.2017.1297993. Epub 2017 Mar 24. PubMed PMID: 28338342. 7: Shen L, Zhang SQ, Liu L, Sun Y, Wu YX, Xie LP, Liu JC. Jolkinolide A and Jolkinolide B Inhibit Proliferation of A549 Cells and Activity of Human Umbilical Vein Endothelial Cells. Med Sci Monit. 2017 Jan 14;23:223-237. PubMed PMID: 28087861; PubMed Central PMCID: PMC5256368. 8: Gao C, Yan X, Wang B, Yu L, Han J, Li D, Zheng Q. Jolkinolide B induces apoptosis and inhibits tumor growth in mouse melanoma B16F10 cells by altering glycolysis. Sci Rep. 2016 Oct 31;6:36114. doi: 10.1038/srep36114. PubMed PMID: 27796318; PubMed Central PMCID: PMC5086858. 9: Lai JZ, Zhang MH, Wu YC, Zhang DY, Wu XM, Hua WY. ent-Abietane Lactones from Euphorbia. Mini Rev Med Chem. 2017;17(4):380-397. Review. PubMed PMID: 27670580. 10: Liu YX, Lu Y, Chen DF. [UPLC Fingerprints of Euphorbiae Ebracteolatae Radix and Its Vinegar-Processed Slices]. Zhong Yao Cai. 2015 Oct;38(10):2060-4. Chinese. PubMed PMID: 27254916. 11: Xu X, Liu N, Zhang YX, Cao J, Wu D, Peng Q, Wang HB, Sun WC. The Protective Effects of HJB-1, a Derivative of 17-Hydroxy-Jolkinolide B, on LPS-Induced Acute Distress Respiratory Syndrome Mice. Molecules. 2016 Jan 11;21(1):77. doi: 10.3390/molecules21010077. PubMed PMID: 26760995. 12: Sun C, Cui H, Yang H, DU X, Yue L, Liu J, Lin YU. Anti-metastatic effect of jolkinolide B and the mechanism of activity in breast cancer MDA-MB-231 cells. Oncol Lett. 2015 Aug;10(2):1117-1122. Epub 2015 Jun 2. PubMed PMID: 26622636; PubMed Central PMCID: PMC4509074. 13: Yang H, Li Y, Huo P, Li XO, Kong D, Mu W, Fang W, Li L, Liu N, Fang L, Li H, He C. Protective effect of Jolkinolide B on LPS-induced mouse acute lung injury. Int Immunopharmacol. 2015 May;26(1):119-24. doi: 10.1016/j.intimp.2015.03.021. Epub 2015 Mar 27. PubMed PMID: 25819665. 14: Pan LC, Xu XH, Zhang NN, Liu N, Wu DL, Wang Y, Peng QS, Vandenplas M, Wang HB, Sun WC. HJB-1, a 17-hydroxy-jolkinolide B derivative, inhibits LPS-induced inflammation in mouse peritoneal macrophages. Int Immunopharmacol. 2014 Aug;21(2):474-80. doi: 10.1016/j.intimp.2014.06.002. Epub 2014 Jun 13. PubMed PMID: 24933588. 15: Ma X, Liu Y, Zhang Y, Yu X, Wang W, Zhao D. Jolkinolide B inhibits RANKL-induced osteoclastogenesis by suppressing the activation NF-κB and MAPK signaling pathways. Biochem Biophys Res Commun. 2014 Mar 7;445(2):282-8. doi: 10.1016/j.bbrc.2014.01.145. Epub 2014 Jan 31. PubMed PMID: 24491533. 16: Zhuang G, Li JS, Cai BC. [Study on HPLC chromatograms of different processed Euphorbia ebracteolata products and content change of three chemical components]. Zhongguo Zhong Yao Za Zhi. 2013 May;38(10):1526-30. Chinese. PubMed PMID: 23947130. 17: Li Y, Liu XL, Cai ZG, Zhang SX. LC-ESI-MS/MS analysis and pharmacokinetics of jolkinolide B, a potential antitumor active component isolated from Euphorbia fischeriana, in rat plasma. Biomed Chromatogr. 2014 Feb;28(2):193-6. doi: 10.1002/bmc.3000. Epub 2013 Jul 19. PubMed PMID: 23868721. 18: Wang JH, Zhang K, Niu HY, Shu LH, Yue DM, Li D, He P. Jolkinolide B from Euphorbia fischeriana Steud induces in human leukemic cells apoptosis via JAK2/STAT3 pathways. Int J Clin Pharmacol Ther. 2013 Mar;51(3):170-8. doi: 10.5414/CP201807. PubMed PMID: 23253949. 19: Zhuang G, Wang L, Zhang Y, Peng W, Li J, Cai B. [Variation regularity of chemical constituents contained in Euphorbia ebracteolata before and after roasting with vinegar]. Zhongguo Zhong Yao Za Zhi. 2012 Aug;37(16):2392-5. Chinese. PubMed PMID: 23234136. 20: Xu HY, Chen ZW, Hou JC, Du FX, Liu JC. Jolkinolide B induces apoptosis in MCF-7 cells through inhibition of the PI3K/Akt/mTOR signaling pathway. Oncol Rep. 2013 Jan;29(1):212-8. doi: 10.3892/or.2012.2113. Epub 2012 Oct 31. PubMed PMID: 23129237.