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D0817

Sigma-Aldrich

(−)-Deguelin

>98% (HPLC), powder

Synonym(s):

(7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-3H-bis[1]benzopyrano[3,4-b:6′,5′-e]pyran-7(7aH)-one

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About This Item

Empirical Formula (Hill Notation):
C23H22O6
CAS Number:
522-17-8
Molecular Weight:
394.42
MDL number:
MFCD01740600
UNSPSC Code:
12352200
PubChem Substance ID:
329798641
NACRES:
NA.77

Quality Level

100

assay

>98% (HPLC)

form

powder

optical activity

[α]/D -70 to -80°, c = 0.2 in methanol

color

white to beige

mp

85-87 °C (lit.)

solubility

DMSO: 10 mg/mL, clear

storage temp.

−20°C

SMILES string

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

InChI

1S/C23H22O6/c1-23(2)8-7-12-15(29-23)6-5-13-21(24)20-14-9-17(25-3)18(26-4)10-16(14)27-11-19(20)28-22(12)13/h5-10,19-20H,11H2,1-4H3/t19-,20+/m1/s1

InChI key

ORDAZKGHSNRHTD-UXHICEINSA-N

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Application

(−)-Deguelin has been used as:
  • a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
  • an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
  • an analytical standard in high-performance liquid chromatography (HPLC)

Biochem/physiol Actions

Deguelin is a natural rotenoid compound present abundantly in barks, leaves, seeds, and roots of the plants belonging to the Leguminosae family. Deguelin has been studied as a therapeutic agent against the skin, lung cancer, and mammary tumorigenesis.
Inhibitor of activated Akt. Does not affect MAPK, ERK1/2, or JNK. Anticancer, chemoprotective agent.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Rahel Sarah Varughese et al.
Cancer, 125(11), 1789-1798 (2019-04-02)
Deguelin is a rotenoid compound that exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants. An analysis of evidence from both in vitro and in vivo studies suggests that deguelin displays potent anticancer
Bin-Chuan Ji et al.
Oncology reports, 27(4), 959-964 (2012-01-10)
It has been shown that deguelin, one of the compounds of rotenoids from flavonoid family, induced cytotoxic effects through induction of cell cycle arrest and apoptosis in many types of human cancer cell lines, but deguelin-affected DNA damage and repair
Zhao-hui Chu et al.
Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine, 9(5), 533-538 (2011-05-14)
To study the effects of deguelin on proliferation and apoptosis of human breast cancer cell line MCF-7 and on phosphatidylinositol 3-kinase/protein kinase B (PI3K/Akt) signaling pathway. After treatment with 0, 1, 5, 10, 15 and 20 μmol/L of deguelin for
Dong-Jo Chang et al.
Journal of medicinal chemistry, 55(24), 10863-10884 (2012-11-29)
Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers. Our initial studies confirmed that deguelin disrupts ATP binding
Vijayalakshmi Thamilselvan et al.
International journal of cancer, 129(12), 2916-2927 (2011-04-08)
Activation of survival pathways has been associated with chemoresistance and progression of androgen independence which places a major obstacle to successful treatment of metastatic prostate cancer. Deguelin, a rotenoid isolated from Mundulea sericea, has an anticancer effect against several types
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