Bruceine A | CAS#25514-31-2 | Lipolysis inducer

MedKoo Cat#: 112197 | Name: Bruceine A

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Description:

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

Bruceine A is a natural quassinoid compound extracted from the fruit of the Traditional Chinese Medicine Brucea javanica (L.) Merr. that has various types of various biological activities and induces lipolysis in 3T3-L1 adipocytes.

Chemical Structure

Bruceine A

CAS#25514-31-2

Theoretical Analysis

MedKoo Cat#: 112197

Name: Bruceine A

CAS#: 25514-31-2

Chemical Formula: C26H34O11

Exact Mass: 522.2101

Molecular Weight: 522.55

Elemental Analysis: C, 59.76; H, 6.56; O, 33.68

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Bruceine A; Dihydrobrusatol; NSC 310616; NSC310616; NSC-310616

IUPAC/Chemical Name

methyl (1R,2S,3S,3aS,3a1R,4R,6aR,7aR,11aS,11bR)-1,2,9-trihydroxy-8,11a-dimethyl-4-((3-methylbutanoyl)oxy)-5,10-dioxo-1,4,5,6a,7,7a,10,11,11a,11b-decahydro-2H-3,3a1-(epoxymethano)dibenzo[de,g]chromene-3(3aH)-carboxylate

InChi Key

LPZSTPCYWWRQFU-VILODJCFSA-N

InChi Code

InChI=1S/C26H34O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h10,12,14,17-21,29-31H,6-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1

SMILES Code

O=C([C@]12[C@]([H])([C@H]3OC(CC(C)C)=O)[C@](CO2)([C@@]([H])(C[C@@]([H])(C(C)=C4O)[C@@]5(CC4=O)C)OC3=O)[C@@]5([C@H]([C@@H]1O)O)[H])OC

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 522.55 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: Li H, Zhao X, Zheng L, Wang X, Lin S, Shen J, Ren H, Li Y, Qiu Q, Wang Z. Bruceine A protects against diabetic kidney disease via inhibiting galectin-1. Kidney Int. 2022 Sep;102(3):521-535. doi: 10.1016/j.kint.2022.04.020. Epub 2022 May 19. PMID: 35598813. 2: Feng XH, Zhang YN, He WZ, Zhang L, Jiang HY. Bruceine a. Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 17;66(Pt 4):o854-5. doi: 10.1107/S1600536810007646. PMID: 21580678; PMCID: PMC2983995. 3: Lu C, Fan L, Zhang PF, Tao WW, Yang CB, Shang EX, Chen FY, Che CT, Cheng HB, Duan JA, Zhao M. A novel P38α MAPK activator Bruceine A exhibits potent anti- pancreatic cancer activity. Comput Struct Biotechnol J. 2021 Jun 6;19:3437-3450. doi: 10.1016/j.csbj.2021.06.011. PMID: 34194669; PMCID: PMC8220105. 4: Zhang P, Tao W, Lu C, Fan L, Jiang Q, Yang C, Shang E, Cheng H, Che C, Duan J, Zhao M. Bruceine A induces cell growth inhibition and apoptosis through PFKFB4/GSK3β signaling in pancreatic cancer. Pharmacol Res. 2021 Jul;169:105658. doi: 10.1016/j.phrs.2021.105658. Epub 2021 May 14. PMID: 33992797. 5: Zhang C, Cao Y, Zuo Y, Cheng H, Liu C, Xia X, Ren B, Deng Y, Wang M, Lu J. Bruceine a exerts antitumor effect against colon cancer by accumulating ROS and suppressing PI3K/Akt pathway. Front Pharmacol. 2023 Mar 28;14:1149478. doi: 10.3389/fphar.2023.1149478. PMID: 37056992; PMCID: PMC10086190. 6: Nakao R, Mizukami C, Kawamura Y, Subeki, Bawm S, Yamasaki M, Maede Y, Matsuura H, Nabeta K, Nonaka N, Oku Y, Katakura K. Evaluation of efficacy of bruceine A, a natural quassinoid compound extracted from a medicinal plant, Brucea javanica, for canine babesiosis. J Vet Med Sci. 2009 Jan;71(1):33-41. doi: 10.1292/jvms.71.33. PMID: 19194074. 7: Knetzger N, Bachtin V, Lehmann S, Hensel A, Liebau E, Herrmann F. The Anthelmintic Quassinoids Ailanthone and Bruceine a Induce Infertility in the Model Organism Caenorhabditis elegans by an Apoptosis-like Mechanism Induced in Gonadal and Spermathecal Tissues. Molecules. 2021 Dec 3;26(23):7354. doi: 10.3390/molecules26237354. PMID: 34885936; PMCID: PMC8659173. 8: 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. PMID: 21196080. 9: Bawm S, Matsuura H, Elkhateeb A, Nabeta K, Subeki, Nonaka N, Oku Y, Katakura K. In vitro antitrypanosomal activities of quassinoid compounds from the fruits of a medicinal plant, Brucea javanica. Vet Parasitol. 2008 Dec 20;158(4):288-94. doi: 10.1016/j.vetpar.2008.09.021. Epub 2008 Sep 26. PMID: 18986767. 10: Yang J, Xiao Y, Lidsky PV, Wu CT, Bonser LR, Peng S, Garcia-Knight MA, Tassetto M, Chung CI, Li X, Nakayama T, Lee IT, Nayak JV, Ghias K, Hargett KL, Shoichet BK, Erle DJ, Jackson PK, Andino R, Shu X. Fluorogenic reporter enables identification of compounds that inhibit SARS-CoV-2. Nat Microbiol. 2023 Jan;8(1):121-134. doi: 10.1038/s41564-022-01288-5. Epub 2023 Jan 5. PMID: 36604514; PMCID: PMC9831272. 11: Elkhateeb A, Tosa Y, Matsuura H, Nabeta K, Katakura K. Antitrypanosomal activities of acetylated bruceines A and C; a structure-activity relationship study. J Nat Med. 2012 Jan;66(1):233-40. doi: 10.1007/s11418-011-0571-5. Epub 2011 Aug 6. PMID: 21822605. 12: Kim JA, Lau EK, Pan L, De Blanco EJ. NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species. Anticancer Res. 2010 Sep;30(9):3295-300. PMID: 20944100; PMCID: PMC3013507. 13: Subeki, Matsuura H, Takahashi K, Nabeta K, Yamasaki M, Maede Y, Katakura K. Screening of Indonesian medicinal plant extracts for antibabesial activity and isolation of new quassinoids from Brucea javanica. J Nat Prod. 2007 Oct;70(10):1654-7. doi: 10.1021/np070236h. Epub 2007 Sep 27. PMID: 17896817. 14: Lahrita L, Moriai K, Iwata R, Itoh K, Kato E. Quassinoids in Brucea javanica are potent stimulators of lipolysis in adipocytes. Fitoterapia. 2019 Sep;137:104250. doi: 10.1016/j.fitote.2019.104250. Epub 2019 Jul 2. PMID: 31271784. 15: Pan L, Chin YW, Chai HB, Ninh TN, Soejarto DD, Kinghorn AD. Bioactivity- guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam. Bioorg Med Chem. 2009 Mar 15;17(6):2219-24. doi: 10.1016/j.bmc.2008.10.076. Epub 2008 Nov 5. Erratum in: Bioorg Med Chem. 2011 Feb 15;19(4):1562. PMID: 19026551; PMCID: PMC2683946. 16: Pierré A, Robert-Géro M, Tempête C, Polonsky J. Structural requirements of quassinoids for the inhibition of cell transformation. Biochem Biophys Res Commun. 1980 Apr 14;93(3):675-86. doi: 10.1016/0006-291x(80)91131-6. PMID: 6155912. 17: Klocke JA, Arisawa M, Handa SS, Kinghorn AD, Cordell GA, Farnsworth NR. Growth inhibitory, insecticidal and antifeedant effects of some antileukemic and cytotoxic quassinoids on two species of agricultural pests. Experientia. 1985 Mar 15;41(3):379-82. doi: 10.1007/BF02004516. PMID: 3972085.