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SMB00172

Sigma-Aldrich

Tephrosin

≥95% (LC/MS-ELSD)

Synonyme(s) :

Deguelinol I, Hydroxydeguelin

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About This Item

Formule empirique (notation de Hill):
C23H22O7
Numéro CAS:
76-80-2
Poids moléculaire :
410.42
Numéro MDL:
MFCD00238693
Code UNSPSC :
12352205
ID de substance PubChem :
329824838
Nomenclature NACRES :
NA.25

Pureté

≥95% (LC/MS-ELSD)

Forme

solid

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

COc1cc2OC[C@H]3Oc4c(ccc5OC(C)(C)C=Cc45)C(=O)[C@@]3(O)c2cc1OC

InChI

1S/C23H22O7/c1-22(2)8-7-12-15(30-22)6-5-13-20(12)29-19-11-28-16-10-18(27-4)17(26-3)9-14(16)23(19,25)21(13)24/h5-10,19,25H,11H2,1-4H3/t19-,23-/m1/s1

Clé InChI

AQBZCCQCDWNNJQ-AUSIDOKSSA-N

Catégories apparentées

Description générale

Natural product derived from plant source.

Actions biochimiques/physiologiques

Tephrosin is a plant-based rotenoid which has known anti-cancer properties. Tephrosin inhibited proliferation in A549 cancer cells in a dose-sependent manner. Tephrosin has been shown to induce capase-independent apoptosis, and internalization and degradation of inactivated EGFR and ErB2 in human colon cancer cells.

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H410

Conseils de prudence

P273 - P501

Classification des risques

Aquatic Acute 1 - Aquatic Chronic 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Sujin Choi et al.
Cancer letters, 293(1), 23-30 (2010-01-09)
Inactivation of epidermal growth factor receptor (EGFR) family members are prime targets for cancer therapy. Here, we show that tephrosin, a natural rotenoid which has potent antitumor activities, induced internalization of EGFR and ErbB2, and thereby induced degradation of the
Shugeng Cao et al.
Journal of natural products, 67(3), 454-456 (2004-03-27)
Bioassay-guided fractionation of methanolic extracts of Mundulea chapelieri resulted in the isolation of two new flavonoids, isomundulinol (1) and 3-deoxy-MS-II (2), in addition to the eight known flavonoids 8-(3,3-dimethylallyl)-5,7-dimethoxyflavanone, MS-II, mundulinol, mundulone, munetone, rotenolone, rotenone, and tephrosin, and one known
Yunjin Choi et al.
Cancer biology & therapy, 12(11), 989-996 (2011-11-30)
2-Deoxy-D-glucose (2-DG), a synthetic glucose analog that acts as a glycolytic inhibitor, is currently under clinical evaluation for targeting tumor cells. Tephrosin (TSN), a plant rotenoid, is known as an anticancer agent. In this study, we describe that the addition
Lu-Rong Xu et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 30(6), 660-662 (2007-10-09)
Five rotenoids named dehydrodeguelin, dehydrorotenone, 12a-hydroxy rotenone, tephrosin and 12alphabeta-hydroxyrot-2'-enonic acid were isolated from aerial parts of Derris trifoliata. All these compounds were isolated from this plant for the first time.
Abiy Yenesew et al.
Phytochemistry, 67(10), 988-991 (2006-02-18)
The crude methanol extract of the seeds of Derris trifoliata showed potent and dose dependent larvicidal activity against the 2nd instar larvae of Aedes aegypti. From this extract two unusual rotenoid derivatives, a rotenoloid (named 7a-O-methyl-12a-hydroxydeguelol) and a spirohomooxarotenoid (named
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