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1.
Life Sci ; 271: 119182, 2021 Apr 15.
Article in English | MEDLINE | ID: mdl-33577851

ABSTRACT

Glitazones are synthetic derivatives of thiazolidinedione, and are designated as oral anti-diabetic agents, primarily acting on peroxisome proliferator-activated receptor-gamma (PPAR-γ) receptors and driving some crucial metabolic pathways linked to glucose and lipid metabolism at transcriptional level. Despite presenting adverse effects, including weight gain, fluid retention, prostate hyperplasia, hyperinsulinemia, and myocardial infarction, they are still preferred in clinical settings due to their utmost efficacy and selectivity. However, these complications kept glitazones restrained for long-term usage. The present review briefly highlights some important synthetic derivatives of thiazolidine2,4-dione and emphasizes the influence of various structural manipulations on their bio-efficacy.


Subject(s)
Hypoglycemic Agents/chemistry , Hypoglycemic Agents/metabolism , Thiazolidinediones/chemistry , Thiazolidinediones/metabolism , Animals , Diabetes Mellitus, Type 2/drug therapy , Diabetes Mellitus, Type 2/metabolism , Glucose/antagonists & inhibitors , Glucose/metabolism , Humans , Hypoglycemic Agents/therapeutic use , Insulin Resistance/physiology , PPAR gamma/metabolism , Protein Structure, Secondary , Protein Structure, Tertiary , Thiazolidinediones/therapeutic use
2.
Bioorg Med Chem ; 14(8): 2545-51, 2006 Apr 15.
Article in English | MEDLINE | ID: mdl-16337386

ABSTRACT

A series of four naturally occurring homoisoflavonoids and eight analogs have been synthesized starting from an appropriately substituted phenol through chroman-4-one, in four steps. The products were assigned as E-isomers based on NMR spectroscopic data. The E-isomers were converted into Z-isomers by photoisomerization. The E- and Z-isomers showed distinct chemical shifts and the differences between (E) and (Z)-homoisoflavonoids in the proton NMR spectra afford a useful method for ascertaining the stereochemistry. The antioxidant activity of homoisoflavonoids was determined by superoxide (NBT) and DPPH free radical scavenging methods. The analog 7-hydroxy-3-[(3,4,5-trihydroxyphenyl)methylene]chroman-4-one displayed excellent activity followed by sappanone A in both the methods and were several times potent than the commercial antioxidants like BHA, BHT, etc. These compounds were evaluated in vitro for their inhibitory activities against 5-lipoxygenase (5-LOX) enzyme. The analog 7-hydroxy-3-[(N,N-dimethylaminophenyl)methylene]chroman-4-one was found to possess potent inhibitory activity and was comparable to that of the standard, nordihydroguiaretic acid. These results suggest that these homoisoflavonoids, with their potent antioxidant and 5-LOX inhibitory activities, may have useful applications as antioxidants and lead compounds for asthma and inflammatory diseases.


Subject(s)
Antioxidants/chemical synthesis , Antioxidants/pharmacology , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Flavonoids/chemical synthesis , Flavonoids/pharmacology , Antioxidants/chemistry , Enzyme Inhibitors/chemistry , Flavonoids/chemistry , Lipoxygenase Inhibitors , Magnetic Resonance Spectroscopy , Stereoisomerism
3.
Chem Pharm Bull (Tokyo) ; 51(12): 1374-6, 2003 Dec.
Article in English | MEDLINE | ID: mdl-14646312

ABSTRACT

Phytochemical investigation of the whole plant of Andrographis viscosula has led to the isolation of three new 2'-oxygenated flavonoids, (2R)-5-hydroxy-7,2',3'-trimethoxyflavanone (1), 7,2',5'-trimethoxyflavone (2), 5,7,2',3'-tetramethoxyflavone (3), and eight known flavones, 5,7,2'-trimethoxyflavone (4), 5,7,2',4',5'-pentamethoxyflavone (5), echioidinin (6), 5,2',6'-trihydroxy-7-methoxyflavone (7), 5-hydroxy-7,2'-dimethoxyflavone (8), echioidin (9), echioidinin 5-O-glucoside (10), and 5,2',6'-trihydroxy-7-methoxyflavone 2'-O-glucoside (11). The structures of 1-11 were elucidated by physical and spectral methods, including extensive 2D NMR studies. The presence of 2'-oxygenated flavonoids is apparently restricted to Andrographis species in Acanthaceae. Therefore, 2'-oxygenated flavonoids are regarded as chemotaxonomic markers of Andrographis genus in the Acanthaceae family.


Subject(s)
Andrographis , Flavonoids/chemistry , Flavonoids/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Structures
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