Bruceine D | CAS#21499-66-1 | carcinoma growth inhibitor

MedKoo Cat#: 562173 | Name: Bruceine D

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Description:

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

Bruceine D is an inhibitor of hepatocellular carcinoma growth. It acts by targeting β-catenin/jagged1 pathways.

Chemical Structure

Bruceine D

CAS#21499-66-1

Theoretical Analysis

MedKoo Cat#: 562173

Name: Bruceine D

CAS#: 21499-66-1

Chemical Formula: C20H26O9

Exact Mass: 410.1577

Molecular Weight: 410.41

Elemental Analysis: C, 58.53; H, 6.39; O, 35.08

Price and Availability

Size	Price	Availability
10mg	USD 450.00	2 Weeks
25mg	USD 850.00	2 Weeks
50g	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Bruceine D; Bruceine-D;

IUPAC/Chemical Name

(1R,2S,3R,3aR,3a1R,4R,6aR,7aS,11S,11aS)-1,2,3a,4,11-pentahydroxy-3,8,11a-trimethyl-1,2,3,3a,4,7,7a,11,11a,11b-decahydro-5H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-5,10(6aH)-dione

InChi Key

JBDMZGKDLMGOFR-CXKYBQEYSA-N

InChi Code

InChI=1S/C20H26O9/c1-7-4-9(21)13(23)17(2)8(7)5-10-19-6-28-18(3,14(24)11(22)12(17)19)20(19,27)15(25)16(26)29-10/h4,8,10-15,22-25,27H,5-6H2,1-3H3/t8-,10+,11+,12?,13+,14-,15-,17-,18+,19+,20+/m0/s1

SMILES Code

CC([C@H](C[C@@H](O1)[C@]23C4[C@@H](O)[C@H](O)[C@](OC3)(C)[C@]2(O)[C@@H](O)C1=O)[C@]4(C)[C@@H]5O)=CC5=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 410.41 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: Man F, Choo CY. Safety assessment of standardized aqueous Brucea javanica extract in rats. J Ethnopharmacol. 2018 Apr 6;215:21-26. doi: 10.1016/j.jep.2017.12.040. Epub 2017 Dec 27. PubMed PMID: 29288829. 2: Man F, Choo CY. HPLC-MS/MS method for bioavailability study of bruceines D & E in rat plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Sep 15;1063:183-188. doi: 10.1016/j.jchromb.2017.08.037. Epub 2017 Aug 30. PubMed PMID: 28869873. 3: Cheng Z, Yuan X, Qu Y, Li X, Wu G, Li C, Zu X, Yang N, Ke X, Zhou J, Xie N, Xu X, Liu S, Shen Y, Li H, Zhang W. Bruceine D inhibits hepatocellular carcinoma growth by targeting β-catenin/jagged1 pathways. Cancer Lett. 2017 Sep 10;403:195-205. doi: 10.1016/j.canlet.2017.06.014. Epub 2017 Jun 20. PubMed PMID: 28645563. 4: Ablat A, Halabi MF, Mohamad J, Hasnan MH, Hazni H, Teh SH, Shilpi JA, Mohamed Z, Awang K. Antidiabetic effects of Brucea javanica seeds in type 2 diabetic rats. BMC Complement Altern Med. 2017 Feb 6;17(1):94. doi: 10.1186/s12906-017-1610-x. PubMed PMID: 28166749; PubMed Central PMCID: PMC5294771. 5: Zhang JY, Lin MT, Tung HY, Tang SL, Yi T, Zhang YZ, Tang YN, Zhao ZZ, Chen HB. Bruceine D induces apoptosis in human chronic myeloid leukemia K562 cells via mitochondrial pathway. Am J Cancer Res. 2016 Mar 15;6(4):819-26. eCollection 2016. PubMed PMID: 27186433; PubMed Central PMCID: PMC4859886. 6: Zhang Y, Zhen Y, Zhang Y, Liu S. Development and validation of a sensitive LC-MS/MS assay for quantification of bruceine D in rat plasma. Biomed Chromatogr. 2016 Nov;30(11):1873-1876. doi: 10.1002/bmc.3724. Epub 2016 Apr 28. PubMed PMID: 27012305. 7: Li L, Leung PS. Use of herbal medicines and natural products: an alternative approach to overcoming the apoptotic resistance of pancreatic cancer. Int J Biochem Cell Biol. 2014 Aug;53:224-36. doi: 10.1016/j.biocel.2014.05.021. Epub 2014 May 27. Review. PubMed PMID: 24875648. 8: Xiao Z, Ching Chow S, Han Li C, Chun Tang S, Tsui SK, Lin Z, Chen Y. Role of microRNA-95 in the anticancer activity of Brucein D in hepatocellular carcinoma. Eur J Pharmacol. 2014 Apr 5;728:141-50. doi: 10.1016/j.ejphar.2014.02.002. Epub 2014 Feb 11. PubMed PMID: 24530415. 9: Liu L, Lin ZX, Leung PS, Chen LH, Zhao M, Liang J. Involvement of the mitochondrial pathway in bruceine D-induced apoptosis in Capan-2 human pancreatic adenocarcinoma cells. Int J Mol Med. 2012 Jul;30(1):93-9. doi: 10.3892/ijmm.2012.980. Epub 2012 Apr 23. PubMed PMID: 22552257. 10: Chen H, Bai J, Fang ZF, Yu SS, Ma SG, Xu S, Li Y, Qu J, Ren JH, Li L, Si YK, Chen XG. Indole alkaloids and quassinoids from the stems of Brucea mollis. J Nat Prod. 2011 Nov 28;74(11):2438-45. doi: 10.1021/np200712y. Epub 2011 Nov 9. PubMed PMID: 22070654. 11: Zhou Z, Shi R, Liu B, Zou J, Wang L, Xia J. [Quantitative determination of contents of three components in Brucea javanica by HPLC]. Zhongguo Zhong Yao Za Zhi. 2011 Jul;36(14):1979-81. Chinese. PubMed PMID: 22016972. 12: Liu JQ, Wang CF, Li XY, Chen JC, Li Y, Qiu MH. One new pregnane glycoside from the seeds of cultivated Brucea javanica. Arch Pharm Res. 2011 Aug;34(8):1297-300. doi: 10.1007/s12272-011-0809-5. Epub 2011 Sep 11. PubMed PMID: 21910051. 13: Zhao M, Lau ST, Leung PS, Che CT, Lin ZX. Seven quassinoids from Fructus Bruceae with cytotoxic effects on pancreatic adenocarcinoma cell lines. Phytother Res. 2011 Dec;25(12):1796-800. doi: 10.1002/ptr.3477. Epub 2011 Apr 8. PubMed PMID: 21480411. 14: Wang Y, Wu ZF, Wang GX, Wang F, Liu YT, Li FY, Han J. In vivo anthelmintic activity of bruceine A and bruceine D from Brucea javanica against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus). Vet Parasitol. 2011 Apr 19;177(1-2):127-33. doi: 10.1016/j.vetpar.2010.11.040. Epub 2010 Dec 3. PubMed PMID: 21196080. 15: Lau ST, Lin ZX, Leung PS. Role of reactive oxygen species in brucein D-mediated p38-mitogen-activated protein kinase and nuclear factor-kappaB signalling pathways in human pancreatic adenocarcinoma cells. Br J Cancer. 2010 Feb 2;102(3):583-93. doi: 10.1038/sj.bjc.6605487. Epub 2010 Jan 12. PubMed PMID: 20068565; PubMed Central PMCID: PMC2822930. 16: Yan XH, Chen J, Di YT, Fang X, Dong JH, Sang P, Wang YH, He HP, Zhang ZK, Hao XJ. Anti-tobacco mosaic virus (TMV) Quassinoids from Brucea javanica (L.) Merr. J Agric Food Chem. 2010 Feb 10;58(3):1572-7. doi: 10.1021/jf903434h. PubMed PMID: 20050684. 17: NoorShahida A, Wong TW, Choo CY. Hypoglycemic effect of quassinoids from Brucea javanica (L.) Merr (Simaroubaceae) seeds. J Ethnopharmacol. 2009 Jul 30;124(3):586-91. doi: 10.1016/j.jep.2009.04.058. Epub 2009 May 9. PubMed PMID: 19439174. 18: Lau ST, Lin ZX, Liao Y, Zhao M, Cheng CH, Leung PS. Bruceine D induces apoptosis in pancreatic adenocarcinoma cell line PANC-1 through the activation of p38-mitogen activated protein kinase. Cancer Lett. 2009 Aug 18;281(1):42-52. doi: 10.1016/j.canlet.2009.02.017. Epub 2009 Mar 14. PubMed PMID: 19286308. 19: Shen JG, Zhang ZK, Wu ZJ, Ouyang MA, Xie LH, Lin QY. Antiphytoviral activity of bruceine-D from Brucea javanica seeds. Pest Manag Sci. 2008 Feb;64(2):191-6. PubMed PMID: 17912689. 20: Xie H, Deng H, Huang S, Wu Z, Zhang M. [Studies on the chemical components of Brucea javanica]. Zhong Yao Cai. 1998 Aug;21(8):398-400. Chinese. PubMed PMID: 12569845.