Improved <i>in Vitro</i> Assays of Superoxide Anion and 1,1-Diphenyl- 2-picrylhydrazyl (DPPH) Radical-Scavenging Activity of Isoflavones and Isoflavone Metabolites

Liang, Xiaolin; Wang, Xiuling; Li, Zhuang; Hao, Qing‐Hong; Wang, Shiying

doi:10.1021/jf102372t

Cited by 51 publications

(35 citation statements)

References 25 publications

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“…Equol [7-hydroxy-3-(4 0 -hydroxyphenyl)-chroman], one metabolite of the isoflavone daidzein, is known to be the most estrogenic compound among all of the isoflavone metabolites. From the recent studies in our laboratory and from related studies, it is clear that equol is a strong antioxidant compound [7][8][9] and can exert significant anticancer activities [10][11].…”

Section: Introductionmentioning

confidence: 99%

Equol induces apoptosis in human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway

Liang

et al. 2014

Anti-Cancer Drugs

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Equol, a microbial metabolite of the isoflavone daidzein, is currently receiving much attention because of its strong antiproliferative effect on hormone-related human breast cancer cells; however, in our previous study, we observed that racemic equol [(±)-equol] shows the highest antiproliferative effect on human hepatocellular carcinoma SMMC-7721 cells compared with other cells, including human breast cancer MCF-7 and MDA-MB-231 cell lines. In the present study, we use the SMMC-7721 cancer cell line to investigate the mechanisms of (±)-equol-induced, R-(+)-equol-induced, and S-(-)-equol-induced apoptosis. Our purpose was to provide some guidelines to introduce equol into a clinical situation. R-(+)-equol and S-(-)-equol were prepared from (±)-equol by chiral stationary phase high performance liquid chromatography. The antiproliferative effect of equol on SMMC-7721 cells was investigated by crystal violet staining. Equol-induced apoptosis was detected by acridine orange/ethidium bromide staining and by flow cytometry. Western blotting was performed to study the molecular mechanisms of equol-induced apoptosis. The results showed that (±)-equol, R-(+)-equol, and S-(-)-equol inhibited the proliferation of SMMC-7721 cells in a concentration-dependent manner. Exposure of SMMC-7721 cells to equol caused significant cell cycle arrest in the S-phase. In addition, equol was shown to induce endoplasmic reticulum stress-mediated apoptosis by activating caspase-12 and caspase-8, and by upregulating Chop and Bip. Mitochondrion-mediated apoptosis was caused by upregulation of Bax and downregulation of Bcl-2, followed by activation of caspase-9, caspase-3, and cleaved poly (ADP-ribose) polymerase, respectively. This is the first report that shows that R-(+)-equol, S-(-)-equol, and (±)-equol can induce apoptosis of human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway.

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Section: Introductionmentioning

confidence: 99%

Equol induces apoptosis in human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway

Liang

et al. 2014

Anti-Cancer Drugs

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“…Oxidative stress is an early and prominent symptom of AD, which plays an important role in AD 20 . All the synthesised compounds were evaluated for their antioxidant activities in the way of scavenging DPPH 25 . The 3-arylbenzofuranone compounds exhibit good antioxidant capacity.…”

Section: Biologymentioning

confidence: 99%

Synthesis and biological evaluation of 3-arylbenzofuranone derivatives as potential anti-Alzheimer’s disease agents

Yang,

Yun,

Miao

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Multi-target drugs can better address the cascade of events involved in oxidative stress and the reduction in cholinergic transmission that occur in Alzheimer's disease than cholinesterase inhibitors alone. We synthesised a series of 3-arylbenzofuranone derivatives and evaluated their antioxidant activity, cholinesterase inhibitory activity, and monoamine oxidase inhibitory activity. 3-Arylbenzofuranone compounds exhibit good antioxidant activity as well as selective acetylcholinesterase inhibitory activity. The IC 50 value of anti-acetylcholinesterase inhibition of Compound 20 (0.089 ± 0.01 lM) is similar to the positive drug donepezil (0.059 ± 0.003 lM). According to the experimental results, Compounds 7, 13 show a certain effect in the in vitro evaluation performed and have the potential as drug candidates for the treatment of Alzheimer's disease. ARTICLE HISTORY

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“…Superoxide effects are involved in many pathological processes, such as inflammation, cancer and aging [37]. The enzymatic superoxide anion radical was generated by the xanthine/xanthine oxidase reaction system [38].…”

Section: Antioxidant Activitymentioning

confidence: 99%

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: A structure–activity relationship study

Prashanth

Madaiah

Revanasiddappa

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Improved in Vitro Assays of Superoxide Anion and 1,1-Diphenyl- 2-picrylhydrazyl (DPPH) Radical-Scavenging Activity of Isoflavones and Isoflavone Metabolites

Cited by 51 publications

References 25 publications

Equol induces apoptosis in human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway

Equol induces apoptosis in human hepatocellular carcinoma SMMC-7721 cells through the intrinsic pathway and the endoplasmic reticulum stress pathway

Synthesis and biological evaluation of 3-arylbenzofuranone derivatives as potential anti-Alzheimer’s disease agents

Synthesis, anticonvulsant, antioxidant and binding interaction of novel N-substituted methylquinazoline-2,4(1H,3H)-dione derivatives to bovine serum albumin: A structure–activity relationship study

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