A diterpene alkaloid with diverse biological activities
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Songorine

Item No. 34601

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,6S,6aR,6bR,9R,11R,11aR,12R,12aR,14R)-1-ethyldodecahydro-6,11-dihydroxy-3-methyl-10-methylene-12,3,6a-ethanylylidene-9,11a-methanoazuleno[2,1-b]azocin-8(9H)-one
CAS Number
509-24-0
Molecular Formula
C22H31NO3
Formula Weight
357.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:4): 0.20 mg/mlDMSO: 5 mg/mlEthanol: slightly soluble
SMILES
O[C@@H]1[C@@]23[C@@]4([H])[C@]5(C[C@H](C([C@H]5O)=C)C(C4)=O)[C@@H]6[C@@]2([H])N(C[C@@]([C@H]3C6)(CC1)C)CC
InChi Code
InChI=1S/C22H31NO3/c1-4-23-10-20(3)6-5-17(25)22-15(20)7-13(18(22)23)21-9-12(11(2)19(21)26)14(24)8-16(21)22/h12-13,15-19,25-26H,2,4-10H2,1,3H3/t12-,13+,15-,16-,17+,18-,19-,20+,21+,22-/m1/s1
InChi Key
CBOSLVQFGANWTL-OFDXIEKGSA-N
Origin
Plant/Aconitum sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Songorine is a diterpene alkaloid that has been found in Aconitum and has diverse biological activities.1,2,3,4 It is an antagonist of the GABAA receptor (IC50 = 7.06 µM in rat brain membranes).1 Songorine (20-80 µM) reduces the viability and migration of, and induces apoptosis in, SKOV3 and A2780 epithelial ovarian cancer cells.2 It also decreases the levels of β-catenin and phosphorylated GSK3β in the same cells and reduces tumor growth in a SKOV3 mouse xenograft model when administered at doses of 0.25 and 2.5 mg/kg. Songorine (0.025 mg/kg) prevents and inhibits paw edema in a mouse model of carrageenan-induced inflammation.3 It also has antinociceptive activity in the early phase of the formalin test in mice when administered at a dose of 46.4 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, X.-Y., Wang, Y., Li, Y., et al. Songorine, a diterpenoid alkaloid of the genus Aconitum, is a novel GABAA receptor antagonist in rat brain. Neurosci. Lett. 337(1), 33-36 (2003).

    2. Zhang, H., Dong, R., Zhang, P., et al. Songorine suppresses cell growth and metastasis in epithelial ovarian cancer via the Bcl‑2/Bax and GSK3β/β‑catenin signaling pathways. Oncol. Rep. 41(5), 3069-3079 (2019).

    3. Nesterova, Y.V., Povetieva, T.N., Suslov, N.I., et al. Anti-inflammatory activity of diterpene alkaloids from Aconitum baikalense. Bull. Exp. Biol. Med. 156(5), 665-668 (2014).

    4. Friese, J., Gleitz, J., Gutser, U.T., et al. Aconitum sp. alkaloids: The modulation of voltage-dependent Na+ channels, toxicity and antinociceptive properties. Eur. J. Pharmacol. 337(2-3), 165-174 (1997).