A pyranocoumarin with diverse biological activities
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Decursinol angelate

Item No. 25212

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2Z)-2-methyl-2-butenoic acid, (7S)-7,8-dihydro-8,8-dimethyl-2-oxo-2H,6H-benzo[1,2-b:5,4-b']dipyran-7-yl ester
CAS Number
130848-06-5
Molecular Formula
C19H20O5
Formula Weight
328.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 2 mg/mlEthanol: 1 mg/ml
λmax
220, 329 nm
SMILES
O=C1C=CC(C=C(C[C@H](OC(/C(C)=C\C)=O)C(C)(C)O2)C2=C3)=C3O1
InChi Code
InChI=1S/C19H20O5/c1-5-11(2)18(21)23-16-9-13-8-12-6-7-17(20)22-14(12)10-15(13)24-19(16,3)4/h5-8,10,16H,9H2,1-4H3/b11-5-/t16-/m0/s1
InChi Key
AGABNGOXUSXQDD-XKGFZTIGSA-N
Origin
Plant/Angelicae sinensis Radix
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

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    10 mg

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    25 mg

    $762

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    Cayman Chemical
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    Product Description

    Decursinol angelate is a pyranocoumarin that has been found in the Korean medicinal herb A. gigas and has diverse biological activities.1,2,3,4,5 It inhibits the growth of K562, HL-60, KG-1, SK-BR-3, AGS, A549, HeLa, HepG2, and G-361 cancer cells (ED50s = 24-56 μM) and decreases estrogen-stimulated growth of MCF-7 breast cancer cells in a concentration-dependent manner via decreased estrogen receptor α (ERα) protein levels and signaling activity.1,2 Decursinol angelate (30 μM) activates PKC purified from rat brain.1 It selectively inhibits the cytochrome P450 (CYP) isoform CYP1A1/2 over CYP2D15 and CYP3A12 in canine liver microsomes (Kis = 67.56, 872.5, and 853.9 μM, respectively).3 Decursinol angelate (0.01-10 μM) reduces cytotoxicity and malondialdehyde (MDA) production induced by amyloid-β (23-35) (Aβ25-35) and increases superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities in PC12 cells.4 In mice, decursinol angelate (200 mg/kg) has antinociceptive activity in the tail flick and hot plate tests and reduces acetic acid-induced writhing as well as decreases production of the pro-inflammatory cytokines TNF-α and IL-1β.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ahn, K.-S., Sim, W.-S., Lee, I.-K., et al. Decursinol angelate: A cytotoxic and protein kinase C activating agent from the root of Angelica gigas. Planta Med. 63(4), 360-361 (1997).

    2. Jiang, C., Guo, J., Wang, Z., et al. Decursin and decursinol angelate inhibit estrogen-stimulated and estrogen-independent growth and survival of breast cancer cells. Breast Cancer Res. 9(6), R77 (2007).

    3. Abd El-Aty, A.M., Shah, S.S., Kim, B.M., et al. In vitro inhibitory potential of decursin and decursinol angelate on the catalytic activity of cytochrome P-450 1A1/2, 2D15, and 3A12 isoforms in canine hepatic microsomes. Arch. Pharm. Res. 31(11), 1425-1435 (2008).

    4. Li, L., Li, W., Jung, S.-W., et al. Protective effects of decursin and decursinol angelate against amyloid β-protein-induced oxidative stress in the PC12 cell line: The role of Nrf2 and antioxidant enzymes. Biosci. Biotech. Biochem. 75(3), 343-342 (2011).

    5. Choi, S.-S., Han, K.-J., Lee, J.-K., et al. Antinociceptive mechanisms of orally administered decursinol in the mouse. Life Sci. 73(4), 471-485 (2003).