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SMB00172

Sigma-Aldrich

Tephrosin

≥95% (LC/MS-ELSD)

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
MDL number:
MFCD00238693
UNSPSC Code:
12352205
PubChem Substance ID:
329824838
NACRES:
NA.25

Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

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

InChI key

AQBZCCQCDWNNJQ-AUSIDOKSSA-N

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

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Xueling Qu et al.
African journal of traditional, complementary, and alternative medicines : AJTCAM, 10(3), 458-468 (2013-10-23)
As the traditional Chinese medicine, the fresh fruits of Amorpha fruticosa L. were applied for the treatment of carbuncle, eczema and burn (Das et al., 2007). However, little is known about the functional roles of the fruits of Amorpha fruticosa
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
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
Nguyen Tien Dat et al.
Journal of natural products, 71(10), 1696-1700 (2008-10-10)
NF-kappaB is known to play a crucial role in the regulation of genes controlling the immune system, apoptosis, tumor cell growth, and tissue differentiation. Bioassay-guided fractionation of the n-hexane-soluble fraction of a methanol extract of Amorpha fruticosa afforded four new
Concise modular asymmetric synthesis of deguelin, tephrosin and investigation into their mode of action.
José Garcia et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 16(32), 9767-9771 (2010-06-24)
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