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MedKoo Cat#: 581006 | Name: Brevilin A
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Description:

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

Brevilin A, is a novel natural product, inhibits janus kinase activity and blocks STAT3 signaling in cancer cells. Brevilin A, which has anticancer activities against a range of cancers, is an abundant constituent of the medicinal herb Centipeda minima (L.) A. Braun & Asch, which has also been reported to have anticancer activity against breast cancer cells.

Chemical Structure

Brevilin A
Brevilin A
CAS#16503-32-5

Theoretical Analysis

MedKoo Cat#: 581006

Name: Brevilin A

CAS#: 16503-32-5

Chemical Formula: C20H26O5

Exact Mass: 346.1780

Molecular Weight: 346.42

Elemental Analysis: C, 69.34; H, 7.57; O, 23.09

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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Synonym
Brevilin A; Brevilin-A; 6-OAP; 6-O-Angeloylplenolin; 6-O-Angeloylplenolin.
IUPAC/Chemical Name
(3S,3aR,4S,4aR,7aR,8R,9aR)-3,4a,8-trimethyl-2,5-dioxo-3H,3aH,4H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl (2Z)-2-methylbut-2-enoate
InChi Key
KUPPZVXLWANEJJ-UXPPPGSFSA-N
InChi Code
InChI=1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1
SMILES Code
C/C=C(C)\C(O[C@@H]([C@@]([C@@H]1C)([H])[C@]2([H])OC1=O)[C@]3(C)C(C=C[C@@]3([H])[C@H](C)C2)=O)=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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Brevilin A is a selective inhibitor of JAK-STAT signal pathway by attenuating the JAKs activity and blocking STAT3 signaling (IC50 = 10.6 µM) in Cancer Cells.
In vitro activity:
Brevilin A reversed the TGF-β1-induced increase in protein and mRNA expression levels of α-SMA and collagen. STAT3 phosphorylation, increased by TGF-β1 treatment, was strongly inhibited by brevilin A; the expression levels of fibronectin and connective tissue growth factor were also significantly decreased by brevilin A. The present study indicated that brevilin A has a preventive and therapeutic potential against hepatic fibrosis. Reference: Bioorg Med Chem Lett. 2021 Jun 1;41:127989. https://pubmed.ncbi.nlm.nih.gov/33794317/
In vivo activity:
To investigate the in vivo anti-cancer effect of BA (brevilin A), this study employed an MDA-MB-231 orthotopic xenograft mouse model. Mice received oral treatment of BA at low (25 mg/kg) or high (50 mg/kg) doses, or i.p. injection of docetaxel as a positive control. After 22 days of treatment, mice were sacrificed. BA treatment suppressed tumor growth and endpoint tumor weight, without causing significant body weight loss (Figure 8A–D). Reference: Onco Targets Ther. 2020 Jun 10;13:5363-5373. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7293987/
Solvent mg/mL mM
Solubility
DMSO 100.0 288.67
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 346.42 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
Formulation protocol:
1. Park YJ, Jeon MS, Lee S, Kim JK, Jang TS, Chung KH, Kim KH. Anti-fibrotic effects of brevilin A in hepatic fibrosis via inhibiting the STAT3 signaling pathway. Bioorg Med Chem Lett. 2021 Jun 1;41:127989. doi: 10.1016/j.bmcl.2021.127989. Epub 2021 Mar 30. PMID: 33794317. 2. Khan M, Maryam A, Saleem MZ, Shakir HA, Qazi JI, Li Y, Ma T. Brevilin A induces ROS-dependent apoptosis and suppresses STAT3 activation by direct binding in human lung cancer cells. J Cancer. 2020 Apr 6;11(13):3725-3735. doi: 10.7150/jca.40983. PMID: 32328177; PMCID: PMC7171504. 3. Qin Q, Xu G, Zhan X, Wang Z, Wang Y, Liu H, Hou X, Shi W, Ma J, Bai Z, Xiao X. Brevilin A inhibits NLRP3 inflammasome activation in vivo and in vitro by acting on the upstream of NLRP3-induced ASC oligomerization. Mol Immunol. 2021 Jul;135:116-126. doi: 10.1016/j.molimm.2021.03.025. Epub 2021 Apr 20. PMID: 33892379. 4. Qu Z, Lin Y, Mok DK, Bian Q, Tai WC, Chen S. Brevilin A, a Natural Sesquiterpene Lactone Inhibited the Growth of Triple-Negative Breast Cancer Cells via Akt/mTOR and STAT3 Signaling Pathways. Onco Targets Ther. 2020 Jun 10;13:5363-5373. doi: 10.2147/OTT.S256833. PMID: 32606754; PMCID: PMC7293987.
In vitro protocol:
1. Park YJ, Jeon MS, Lee S, Kim JK, Jang TS, Chung KH, Kim KH. Anti-fibrotic effects of brevilin A in hepatic fibrosis via inhibiting the STAT3 signaling pathway. Bioorg Med Chem Lett. 2021 Jun 1;41:127989. doi: 10.1016/j.bmcl.2021.127989. Epub 2021 Mar 30. PMID: 33794317. 2. Khan M, Maryam A, Saleem MZ, Shakir HA, Qazi JI, Li Y, Ma T. Brevilin A induces ROS-dependent apoptosis and suppresses STAT3 activation by direct binding in human lung cancer cells. J Cancer. 2020 Apr 6;11(13):3725-3735. doi: 10.7150/jca.40983. PMID: 32328177; PMCID: PMC7171504.
In vivo protocol:
1. Qin Q, Xu G, Zhan X, Wang Z, Wang Y, Liu H, Hou X, Shi W, Ma J, Bai Z, Xiao X. Brevilin A inhibits NLRP3 inflammasome activation in vivo and in vitro by acting on the upstream of NLRP3-induced ASC oligomerization. Mol Immunol. 2021 Jul;135:116-126. doi: 10.1016/j.molimm.2021.03.025. Epub 2021 Apr 20. PMID: 33892379. 2. Qu Z, Lin Y, Mok DK, Bian Q, Tai WC, Chen S. Brevilin A, a Natural Sesquiterpene Lactone Inhibited the Growth of Triple-Negative Breast Cancer Cells via Akt/mTOR and STAT3 Signaling Pathways. Onco Targets Ther. 2020 Jun 10;13:5363-5373. doi: 10.2147/OTT.S256833. PMID: 32606754; PMCID: PMC7293987.
1: Yen LJ, Yen CY, Li CL, Liao EC, Wang KC, Shih MC, Huang HS, Chen YC, Lu LY, Yu SJ. Brevilin A Ameliorates Imiquimod-Induced Psoriasis-like Dermatitis and Reduces Th17 Differentiation in Psoriasis Patients. J Pers Med. 2022 Nov 10;12(11):1888. doi: 10.3390/jpm12111888. PMID: 36579613; PMCID: PMC9693458. 2: Lee D, Kwak HJ, Kim BH, Kim DW, Kim HY, Kim SH, Kang KS. Brevilin A Isolated from Centipeda minima Induces Apoptosis in Human Gastric Cancer Cells via an Extrinsic Apoptotic Signaling Pathway. Plants (Basel). 2022 Jun 23;11(13):1658. doi: 10.3390/plants11131658. PMID: 35807611; PMCID: PMC9268799. 3: Zhu X, Liu F, Wu Q, Li S, Ruan G, Yang J, Yu C, Jiang N, Xiao Y, Liu Y. Brevilin A enhances innate immunity and the resistance of oxidative stress in Caenorhabditis elegans via p38 MAPK pathway. Int Immunopharmacol. 2022 Dec;113(Pt A):109385. doi: 10.1016/j.intimp.2022.109385. Epub 2022 Oct 30. PMID: 36330917. 4: Wei B, Hao Z, Zheng H, Qin Y, Zhao F, Shi L. Brevilin A Inhibits VEGF-Induced Angiogenesis through ROS-Dependent Mitochondrial Dysfunction. Oxid Med Cell Longev. 2022 Dec 14;2022:5888636. doi: 10.1155/2022/5888636. PMID: 36567856; PMCID: PMC9771652. 5: Park YJ, Jeon MS, Lee S, Kim JK, Jang TS, Chung KH, Kim KH. Anti-fibrotic effects of brevilin A in hepatic fibrosis via inhibiting the STAT3 signaling pathway. Bioorg Med Chem Lett. 2021 Jun 1;41:127989. doi: 10.1016/j.bmcl.2021.127989. Epub 2021 Mar 30. PMID: 33794317. 6: Liu L, Chen X, Jiang Y, Yuan Y, Yang L, Hu Q, Tang J, Meng X, Xie C, Shen X. Brevilin A Ameliorates Acute Lung Injury and Inflammation Through Inhibition of NF-κB Signaling via Targeting IKKα/β. Front Pharmacol. 2022 Jun 14;13:911157. doi: 10.3389/fphar.2022.911157. PMID: 35774606; PMCID: PMC9237443. 7: Fan X, Meng M, Li B, Chen H, Tan J, Xu K, Xiao S, Kwan HY, Liu Z, Su T. Brevilin A is a potent anti-metastatic CRC agent that targets the VEGF-IL6-STAT3 axis in the HSCs-CRC interplay. J Transl Med. 2023 Apr 16;21(1):260. doi: 10.1186/s12967-023-04087-6. PMID: 37062842; PMCID: PMC10105967. 8: Zhang X, Xia Y, Yang L, He J, Li Y, Xia C. Brevilin A, a Sesquiterpene Lactone, Inhibits the Replication of Influenza A Virus In Vitro and In Vivo. Viruses. 2019 Sep 8;11(9):835. doi: 10.3390/v11090835. PMID: 31500389; PMCID: PMC6783993. 9: Qu Z, Lin Y, Mok DK, Bian Q, Tai WC, Chen S. Brevilin A, a Natural Sesquiterpene Lactone Inhibited the Growth of Triple-Negative Breast Cancer Cells via Akt/mTOR and STAT3 Signaling Pathways. Onco Targets Ther. 2020 Jun 10;13:5363-5373. doi: 10.2147/OTT.S256833. PMID: 32606754; PMCID: PMC7293987. 10: Muscianese M, Magri F, Leoncini P, Fortuna MC, Caro G, Rossi A. Alopecia areata treated with topical and systemic brevilin A: A case series. Dermatol Ther. 2021 Mar;34(2):e14778. doi: 10.1111/dth.14778. Epub 2021 Feb 10. PMID: 33438308. 11: Liu R, Qu Z, Lin Y, Lee CS, Tai WC, Chen S. Brevilin A Induces Cell Cycle Arrest and Apoptosis in Nasopharyngeal Carcinoma. Front Pharmacol. 2019 May 24;10:594. doi: 10.3389/fphar.2019.00594. PMID: 31178739; PMCID: PMC6544084. 12: Qin Q, Xu G, Zhan X, Wang Z, Wang Y, Liu H, Hou X, Shi W, Ma J, Bai Z, Xiao X. Brevilin A inhibits NLRP3 inflammasome activation in vivo and in vitro by acting on the upstream of NLRP3-induced ASC oligomerization. Mol Immunol. 2021 Jul;135:116-126. doi: 10.1016/j.molimm.2021.03.025. Epub 2021 Apr 20. PMID: 33892379. 13: Wang J, Li M, Cui X, Lv D, Jin L, Khan M, Ma T. Brevilin A promotes oxidative stress and induces mitochondrial apoptosis in U87 glioblastoma cells. Onco Targets Ther. 2018 Oct 16;11:7031-7040. doi: 10.2147/OTT.S179730. PMID: 30410360; PMCID: PMC6198872. 14: Su T, Wang YP, Wang XN, Li CY, Zhu PL, Huang YM, Yang ZY, Chen SB, Yu ZL. The JAK2/STAT3 pathway is involved in the anti-melanoma effects of brevilin A. Life Sci. 2020 Jan 15;241:117169. doi: 10.1016/j.lfs.2019.117169. Epub 2019 Dec 14. PMID: 31843524. 15: Khan M, Maryam A, Saleem MZ, Shakir HA, Qazi JI, Li Y, Ma T. Brevilin A induces ROS-dependent apoptosis and suppresses STAT3 activation by direct binding in human lung cancer cells. J Cancer. 2020 Apr 6;11(13):3725-3735. doi: 10.7150/jca.40983. PMID: 32328177; PMCID: PMC7171504. 16: Saleem MZ, Nisar MA, Alshwmi M, Din SRU, Gamallat Y, Khan M, Ma T. Brevilin A Inhibits STAT3 Signaling and Induces ROS-Dependent Apoptosis, Mitochondrial Stress and Endoplasmic Reticulum Stress in MCF-7 Breast Cancer Cells. Onco Targets Ther. 2020 Jan 15;13:435-450. doi: 10.2147/OTT.S228702. PMID: 32021288; PMCID: PMC6970270. 17: You P, Tang L, Zhu Y, Tian Y. Brevilin A shows an anti-tumor role in prostate cancer via the lncRNA H19/miR-194/E2F3 signaling pathway. Aging (Albany NY). 2023 May 30;15(10):4411-4428. doi: 10.18632/aging.204744. Epub 2023 May 30. PMID: 37253635; PMCID: PMC10258005. 18: Chen X, Du Y, Nan J, Zhang X, Qin X, Wang Y, Hou J, Wang Q, Yang J. Brevilin A, a novel natural product, inhibits janus kinase activity and blocks STAT3 signaling in cancer cells. PLoS One. 2013 May 21;8(5):e63697. doi: 10.1371/journal.pone.0063697. PMID: 23704931; PMCID: PMC3660600. 19: You P, Wu H, Deng M, Peng J, Li F, Yang Y. Brevilin A induces apoptosis and autophagy of colon adenocarcinoma cell CT26 via mitochondrial pathway and PI3K/AKT/mTOR inactivation. Biomed Pharmacother. 2018 Feb;98:619-625. doi: 10.1016/j.biopha.2017.12.057. Epub 2017 Dec 29. PMID: 29289836. 20: Qin Y, Lu H. In vitro evaluation of anti-hepatoma activity of brevilin A: involvement of Stat3/Snail and Wnt/β-catenin pathways. RSC Adv. 2019 Feb 5;9(8):4390-4396. doi: 10.1039/c8ra08574a. PMID: 35547606; PMCID: PMC9088035.