SML3465

Toosendanin

Name: Toosendanin
Brand: SIGMA

≥90% (HPLC)

别名:

(1S,2aR,3aS,3bS,4R,5aR,6R,7S,9S,9aS,9bR,11R,11aR,14S)-1-(furan-3-yl)-4,9,14-trihydroxy-3b,6,11a-trimethyl-10-oxotetradecahydro-1H-6,9a-(methanooxymethano)naphtho[1′,2′:6,7]indeno[1,7a-b]oxirene-7,11-diyl diacetate, 28-Deacetylsendanin, Chuanliansu

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关于此项目

经验公式（希尔记法）:

C₃₀H₃₈O₁₁

化学文摘社编号:

58812-37-6

分子量:

574.62

MDL编号:

MFCD00210564

UNSPSC代码:

51111800

NACRES:

NA.77

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质量水平

100

方案

≥90% (HPLC)

表单

powder

颜色

white to beige

溶解性

DMSO: 2 mg/mL, clear

储存温度

-10 to -25°C

SMILES字符串

C[C@@]1([C@H]2OC(C)=O)[C@]3([C@]([H])(O3)C[C@H]1C4=COC=C4)[C@]5(C)[C@H](O)C[C@@]6([H])[C@@](C)([C@@H]7O)[C@H](OC(C)=O)C[C@H](O)[C@]6(CO7)[C@@]5([H])C2=O

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/

InChI key

NAHTXVIXCMUDLF-RFNFAWMESA-N

生化/生理作用

Botulinum neurotoxin inhibitor; Inhibitor of anthrax Lethal Toxin-induced cell death; exhibits potent antiviral activity against SARS-CoV-2, SFTSV, and bunyavirus.

Toosendanin is a natural occuring triterpenoid recently found to be an inhibitor of botulinum neurotoxin and also found to be an inhibitor of anthrax Lethal Toxin (LT)-induced cell death. Anthrax toxin is composed of three proteins: the toxin B subunit protective antigen (PA), a zinc metalloprotease lethal factor (LF), and an adenylate cyclase edema factor (EF). PA and EF combine to form edema toxin (ET) while PA and LF combine to form lethal toxin (LT), which induces rapid caspase-1 dependent cell death in macrophages. Toosendanin had an IC50 of 56 nM (32 ng/ml) against LT, likely by inhibiting endocytosis and endosomal acidification. Toosendanin has also been found to suppress proliferation and induce apoptosis in a variety of human cancer cells, possibly mediated through JNK signaling pathway.