Synthesis and biological evaluation of β-ionone oriented proapoptosis agents by enhancing the ROS generation

Yang, Jie; Mu, Wen-Wen; Cao, Yuxin; Liu, Guoyun

doi:10.1016/j.bioorg.2020.104273

Cited by 12 publications

(2 citation statements)

References 25 publications

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“…Ionone, a monoterpene found in natural products [ 4 ], is an important raw material widely used in the fields of medicine and perfume [ 5 ]. Experimental results have shown that the β-isomer of ionone has good biological activity [ 6 , 7 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antioxidant, and Antifungal Activities of β-Ionone Thiazolylhydrazone Derivatives and Their Application in Anti-Browning of Freshly Cut Potato

Huang,

Zhong,

Zeng

et al. 2023

Molecules

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In order to develop a new type of antioxidants with high efficiency, a series of β-ionone thiazolylhydrazone derivatives were designed and synthesized from β-ionone, and their structures were characterized by 1H-NMR, 13C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated that most of the target compounds had high biological activity. Among them, compound 1k exhibited very strong DPPH (1,1-diphenyl-2-picrylhydrazyl radical)-scavenging activity with a half-maximal effective concentration (IC50) of 86.525 μM. Furthermore, in the ABTS (2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) diammonium salt)-scavenging experiment, compound 1m exhibited excellent activity with an IC50 of 65.408 μM. Their biological activities were significantly better than those of the positive control Trolox. These two compounds, which have good free-radical-scavenging activity in vitro, were used as representative compounds in the anti-browning experiment of fresh-cut potatoes. The results showed that 1k and 1m had the same anti-browning ability as kojic acid, and they were effective browning inhibitors. In addition, it is well known that microbial infection is one of the reasons for food oxidation. Therefore, we investigated the antifungal activity of 25 target compounds against eight plant fungi at a concentration of 125 mg/L. The results indicated that these compounds all have some antifungal activity and may become new potential fungicides. Notably, compound 1u showed the best inhibitory effect against Poria vaporaria, with an inhibition rate as high as 77.71%; it is expected to become the dominant structure for the development of new antifungal agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antioxidant, and Antifungal Activities of β-Ionone Thiazolylhydrazone Derivatives and Their Application in Anti-Browning of Freshly Cut Potato

Huang,

Zhong,

Zeng

et al. 2023

Molecules

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“…β-Ionone is a terminal analog of β-carotene and is an important intermediate for many chemicals [6]. β-ionone is a natural flavor mainly found in fruits and grains, and numerous studies have confirmed that it has certain anti-inflammatory, antioxidant and anti-tumor effects [7][8][9]. It has been confirmed that the growth of tumor cells can be inhibited by βionone-mediated cell cycle arrest, anti-oxidation, and promotion of apoptosis in gastric cancer [10], liver cancer [11], breast cancer [12] and PCa [13].…”

Section: Introductionmentioning

confidence: 99%

β-ionone Inhibits Epithelial-Mesenchymal Transition (EMT) in Prostate Cancer Cells by Negatively Regulating the Wnt/β-Catenin Pathway

Fang

Que

Liu

et al. 2022

Front. Biosci. (Landmark Ed)

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Background: β-ionone is a terminal cyclic analog of beta-carotenoids widely found in plants. In recent years, accumulating evidence has shown that β-ionone exerts antitumor effects on various malignant tumors. However, limited studies have revealed the role of β-ionone in regulating the epithelial-mesenchymal transition (EMT) of prostate cancer (PCa) cells. This study aimed to investigate the effect of β-ionone on the EMT process of PCa, focusing on Wnt/β-catenin signaling pathway. Methods: After exposure to βionone, cell viability was determined by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and the Brdu proliferation assay. The Transwell and wounding healing were used to investigate the migration and invasion abilities of PCa cells. Expression of proteins involved in the EMT process (E-cadherin, N-cadherin, vimentin) and proteins in the Wnt/β-catenin pathway (βcatenin, GSK3-β, and p-GSK3-β) were explored by western blotting. The effects of β-ionone on β-catenin degradation were explored by cycloheximide tracking assay and in vitro ubiquitination assay. Nude mouse xenograft model was served as the model system in vivo. Results: The migration, invasion, and EMT process of PCa Human PC-3 prostate adenocarcinoma cells (PC3) and Human 22RV1 prostate adenocarcinoma cells (22RV1) cells were significantly inhibited after β-ionone treatment. In addition, β-ionone also inhibited the growth and EMT process of subcutaneous xenograft tumors in nude mice. The study also found that β-catenin, which promotes EMT, was downregulated after β-ionone treatment. Further mechanistic studies revealed that β-ionone inhibited the Wnt/β-catenin pathway by accelerating the ubiquitination and degradation of β-catenin in PCa, thus inhibiting the downstream migration, invasion, and EMT processes. Conclusions: These findings demonstrate that β-ionone may be a potential natural compound targeting the Wnt/β-catenin pathway for the treatment of PCa.

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Cinnamic acid/β-ionone hybrids: synthesis and in vitro anticancer activity evaluation

et al. 2021

Monatsh Chem

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Synthesis and biological evaluation of β-ionone oriented proapoptosis agents by enhancing the ROS generation

Cited by 12 publications

References 25 publications

Synthesis, Antioxidant, and Antifungal Activities of β-Ionone Thiazolylhydrazone Derivatives and Their Application in Anti-Browning of Freshly Cut Potato

Synthesis, Antioxidant, and Antifungal Activities of β-Ionone Thiazolylhydrazone Derivatives and Their Application in Anti-Browning of Freshly Cut Potato

β-ionone Inhibits Epithelial-Mesenchymal Transition (EMT) in Prostate Cancer Cells by Negatively Regulating the Wnt/β-Catenin Pathway

Cinnamic acid/β-ionone hybrids: synthesis and in vitro anticancer activity evaluation

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