An alkaloid with diverse biological activities
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.

(–)-Cryptopleurine

Item No. 31642

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11,12,13,14,14aR,15-hexahydro-2,3,6-trimethoxy-9H-phenanthro[9,10-b]quinolizine
CAS Number
482-22-4
Synonyms
  • (R)-Cryptopleurine
  • NSC 19912
Molecular Formula
C24H27NO3
Formula Weight
377.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: solubleMethanol: soluble
λmax
260, 287 nm
SMILES
COC1=CC2=C3C(CN4[C@@](CCCC4)([H])C3)=C5C(C=C(C=C5)OC)=C2C=C1OC
InChi Code
InChI=1S/C24H27NO3/c1-26-16-7-8-17-19(11-16)21-13-24(28-3)23(27-2)12-20(21)18-10-15-6-4-5-9-25(15)14-22(17)18/h7-8,11-13,15H,4-6,9-10,14H2,1-3H3/t15-/m1/s1
InChi Key
RSHYSOGXGSUUIJ-OAHLLOKOSA-N
Origin
Plant/Cryptocarya pleurosperma
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

    $294

    Add

    5 mg

    $1,025

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    (–)-Cryptopleurine is an alkaloid that has been found in Lauraceae and has diverse biological activities.1 It inhibits the growth of human A375 melanoma, A431 epidermoid carcinoma, A549 lung, MES-SA uterine sarcoma, and MCF-7 breast cancer cells (IC50 = 3 nM for all).2 (–)-Cryptopleurine inhibits hypoxia-induced gene expression in a hypoxia response element (HRE) reporter assay (IC50 = 8.7 nM).3 (–)-Cryptopleurine (500 µg/ml) prevents lesion formation in tobacco (N. tabacum) plants infected with tobacco mosaic virus (TMV).1 It also inhibits protein synthesis by yeast and mammalian ribosomes.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, Z., Feng, A., Cui, M., et al. First discovery and stucture-activity relationship study of phenanthroquinolizidines as novel antiviral agents against Tobacco Mosaic Virus (TMV). PLoS One 7(12), e52933 (2012).

    2. Banwell, M.G., Bezos, A., Burns, C., et al. C8c-C15 monoseco-analogues of the phenanthroquinolizidine alkaloids julandine and cryptopleurine exhibiting potent anti-angiogenic properties. Bioorg. Med. Chem. Lett. 16(1), 181-185 (2006).

    3. Cai, X.F., Jin, X., Lee, D., et al. Phenanthroquinolizidine alkaloids from the roots of Boehmeria pannosa potently inhibit hypoxia-inducible factor-1 in AGS human gastric cancer cells. J. Nat. Prod. 69(7), 1095-1097 (2006).

    4. Battaner, E., and Vazquez, D. Inhibitors of protein synthesis by ribosomes of the 80-S type. Biochim. Biophys. Acta 254(2), 316-330 (1971).

    5. Pestka, S., Rosenfeld, H., Harris, R., et al. Studies on transfer ribonucleic acid-ribosome complexes. XXI. Effect of antibiotics on peptidyl-puromycin synthesis by mammalian polyribosomes. The Journal of Biological Chemisty 247(21), 6895-6900 (1972).