(-)-DEGUELIN

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.

Molecular Weight: 394.42. Empirical Formula: C₂₃H₂₂O₆. 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. Storage Class Code: 11 - Combustible Solids. WGK: WGK 3. Flash Point(F): Not applicable. Flash Point(C): Not applicable. Personal Protective Equipment: Eyeshields, Gloves, type N95 (US).