A flavolignan with diverse biological activities
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Deoxypodophyllotoxin

Item No. 36434

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5R,5aR,8aR)-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
CAS Number
19186-35-7
Synonyms
  • Anthricin
  • (–)-Deoxypodophyllotoxin
  • 4-Deoxypodophyllotoxin
  • DPT
  • RD4-6266
Molecular Formula
C22H22O7
Formula Weight
398.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly soluble (warm)Methanol: Slightly soluble (warm)
SMILES
O=C1[C@]2([H])[C@@](C3=CC(OC)=C(C(OC)=C3)OC)([H])C4=CC(OCO5)=C5C=C4C[C@@]2([H])CO1
InChi Code
InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+,20-/m0/s1
InChi Key
ZGLXUQQMLLIKAN-SVIJTADQSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    Cayman Chemical
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    Product Description

    Deoxypodophyllotoxin (DPT) is a flavolignan that has been found in J. sabina and has diverse biological activities.1,2,3,4,5 It inhibits tubulin polymerization in a cell-free assay when used at a concentration of 50 nM.1 DPT in also inhibits COX-2 and 5-lipoxygenase (5-LO) in isolated mouse bone marrow-derived mast cells stimulated with KL, IL-10, and LPS (IC50s = 1.89 and 0.37 µM, respectively).2 It reduces viral yield in the supernatant of MRC-5 cells infected with herpes simplex virus 1 (HSV-1) or HSV-2 when used at a concentration of 0.02 µg/ml.3 DPT inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in a concentration-dependent manner.4 It induces mortality in P. rapae fifth instar larvae (LC50 = 0.02 g/L).5 DPT (70 µg/kg) reduces tumor growth in a CT26 murine colon cancer model.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gamage, C.D.B., Park, S.-Y., Yang, Y., et al. Deoxypodophyllotoxin exerts anti-cancer effects on colorectal cancer cells through induction of apoptosis and suppression of tumorigenesis. Int. J. Mol. Sci. 20(11), 2612 (2019).

    2. Lee, S.H., Son, M.J., Ju, H.K., et al. Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells. Biol. Pharm. Bull. 27(6), 786-788 (2004).

    3. Sudo, K., Konno, K., Shigeta, S., et al. Inhibitory effects of podophyllotoxin derivatives on herpes simplex virus replication. Antivir. Chem. Chemother. 9(3), 263-267 (1998).

    4. Chen, J.-J., Chang, Y.-L., Teng, C.-M., et al. Anti-platelet aggregation alkaloids and lignans from Hernandia nymphaeifolia. Planta Med. 66(3), 251-256 (1999).

    5. Gao, R., Gao, C., Tian, X., et al. Insecticidal activity of deoxypodophyllotoxin, isolated from Juniperus sabina L, and related lignans against larvae of Pieris rapae L. Pest Manag. Sci. 60(11), 1131-1136 (2004).