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Merck
CN

SMB00172

Tephrosin

Synonym(s):

Deguelinol I, Hydroxydeguelin

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About This Item

Empirical Formula (Hill Notation):
C23H22O7
CAS Number:
76-80-2
Molecular Weight:
410.42
NACRES:
NA.25
PubChem Substance ID:
329824838
UNSPSC Code:
12352205
MDL number:
MFCD00238693

Key Documents

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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

SMILES string

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

InChI key

AQBZCCQCDWNNJQ-AUSIDOKSSA-N

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Related Categories

General description

Natural product derived from plant source.

Biochem/physiol Actions

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.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
122228336V
122228339V
122228339
122228224V
122228-224V

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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
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
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
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.
Pest management science, 59(10), 1159-1161 (2003-10-17)
A crude chloroform extract of seeds of Millettia dura Dunn (Leguminosae) showed high activity (LC50 = 3.5 microg ml(-1) at 24 h) against second-instar larvae of the mosquito, Aedes aegypti L (Diptera: Culicidae). The rotenoids, deguelin and tephrosin, isolated from
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