A sesquiterpene lactone with anticancer activity
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Brevilin A

Item No. 33993

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2Z)-2-methyl-2-butenoic acid, 2,3S,3aR,4S,4aR,5,7aR,8R,9,9aR-decahydro-3,4a,8-trimethyl-2,5-dioxoazuleno[6,5-b]furan-4-yl ester
CAS Number
16503-32-5
Synonyms
  • 6-O-Angeloylprenolin
  • Brevelin A
Molecular Formula
C20H26O5
Formula Weight
346.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 100 mg/ml
λmax
223 nm
SMILES
C/C=C(C)\C(O[C@H]1[C@@]2([H])[C@@](OC([C@H]2C)=O)([H])C[C@H]([C@@]3([H])[C@]1(C(C=C3)=O)C)C)=O
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
InChi Key
KUPPZVXLWANEJJ-UXPPPGSFSA-N
Origin
Plant/Centipeda minima
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $98

    Add

    5 mg

    $294

    Add

    10 mg

    $490

    Add

    25 mg

    $857

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Brevilin A is a sesquiterpene lactone that has been found in C. minima and has anticancer activity.1 It is an inhibitor of STAT3 signaling (IC50 = 10.6 µM in A549R cells) that inhibits the tyrosine kinase activity of the JAK1, JAK2, JAK3, and JAK4 JH1 subunit (IC50s = 11.2, 8.4, 10.2, and 11.9 µM, respectively).2 It inhibits proliferation of a variety of cancer cells, including A549 lung, HepG2 liver, HeLa cervical, A875 melanoma, and CT26 mouse colon carcinoma cells in a concentration-dependent manner.1 Brevilin A (1-4 µg/ml) decreases the mitochondrial membrane potential, induces apoptosis, and increases the level of reactive oxygen species (ROS) in CT26 cells. It also induces autophagosome formation in CT26 cells, an effect that can be blocked by the PI3K inhibitor 3-methyladenine (Item No. 13242). Brevilin A (5 mg/kg per day) increases intratumor expression of the autophagy marker LC3-II and reduces tumor growth in a murine CT26 colon cancer model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. You, P., Wu, H., Deng, M., et al. Brevilin A induces apoptosis and autophagy of colon adenocarcinoma cell CT26 via mitochondrial pathway and PI3K/AKT/mTOR inactivation. Biomed. Pharmacother. 98, 619-625 (2018).

    2. Chen, X., Du, Y., Nan, J.X., et al. Brevilin A, a novel natural product, inhibits janus kinase activity and blocks STAT3 signaling in cancer cells. PLoS One 8(5), e63697 (2013).