A triterpenoid with diverse biological activities
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Toosendanin

Item No. 34042

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
[C(R),1α,3α,4β,5α,7α,12α,13α,14β,15β,17α]-3,12-bis(acetyloxy)-14,15:21,23-diepoxy-1,7,19-trihydroxy-4,8-dimethyl-11-oxo-cyclic 4,19-hemiacetal, 24-norchola-20,22-diene-4-carboxaldehyde
CAS Number
58812-37-6
Synonyms
  • Chuanliansu
  • 28-Deacetylsendanin
Molecular Formula
C30H38O11
Formula Weight
574.6
Purity
≥95% (mixture of isomers)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:6): 0.14 mg/mlEthanol: 5 mg/ml
SMILES
C[C@]12[C@]34[C@]([C@@](C5=COC=C5)([H])C[C@@]3([H])O4)([C@H](C([C@]1([H])[C@]67[C@@]([C@]([C@@H](C[C@@H]6O)OC(C)=O)([C@@H](OC7)O)C)([H])C[C@H]2O)=O)OC(C)=O)C
InChi Code
InChI=1S/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20+,21+,23-,24-,25+,26+,27+,28+,29+,30+/m0/s1
InChi Key
NAHTXVIXCMUDLF-RFNFAWMESA-N
Origin
Plant/Melia toosendan
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

    Toosendanin is a triterpenoid that has been found in M. toosendan and has diverse biological activities.1,2,3 It inhibits the proliferation of BEL-7404, U251, SH-SY5Y, HL-60, PC3, and U937 cancer cells (IC50s = <0.17 µM for all).1 Toosendanin is larvicidal against A. aegypti first instar larvae (LC50 = 60.8 µg/ml) and delays pupal development when used at concentrations ranging from 6.3 to 25 µg/ml.2 It decreases serum levels of TNF-α, IL-1β, and IL-6 in a mouse model of ulcerative colitis induced by dextran sulfate (sodium salt) (DSS; Item No. 23250) when administered at doses of 0.5 and 1 mg/kg.3 Toosendanin (9 mg/kg) increases survival in a mouse model of botulism induced by botulinum neurotoxin serotype A (BoNT/A).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shi, Y.-L., and Li, M.-F. Biological effects of toosendanin, a triterpenoid extracted from Chinese traditional medicine. Prog. Neurobiol. 82(1), 1-10 (2007).

    2. Ma, Z., Gulia-Nuss, M., Zhang, X., et al. Effects of the botanical insecticide, toosendanin, on blood digestion and egg production by female Aedes aegypti (Diptera: Culicidae): Topical application and ingestion. J. Med. Entomol. 50(1), 112-121 (2013).

    3. Fan, H., Chen, W., Zhu, J., et al. Toosendanin alleviates dextran sulfate sodium-induced colitis by inhibiting M1 macrophage polarization and regulating NLRP3 inflammasome and Nrf2/HO-1 signaling. Int. Immunopharmacol. 76, 105909 (2019).