Synthesis and Anti‐Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs

Ketabforoosh, Shima H. M. E.; Kheirollahi, Asma; Safavi, Maliheh; Esmati, Nasim; Ardestani, Sussan K.; Emami, Saeed; Firoozpour, Loghman; Shafiee, Abbas; Foroumadi, Alireza

doi:10.1002/ardp.201400215

Cited by 29 publications

(10 citation statements)

References 27 publications

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“…Ketabforoosh et al found that chalcones with a 3,4-dimethoxyphenyl moiety in their structure and their derivatives with an additional chloride atom or methoxy group at carbon C-5 are much more potent inhibitors of cell growth than corresponding flavanones as observed in three different cancer cell lines—neuroblastoma cell line SK-N-MC and breast cancer cell lines: MDA-MB-231 and MCF-7. 40 In contrast, the attachment of a pyrrolidinylmethoxy group at position C-7 of a flavanone structure increased the cytotoxicity of flavanones when compared to their parent chalcone.…”

Section: Discussionmentioning

confidence: 99%

Cyclization of flavokawain B reduces its activity against human colon cancer cells

et al. 2019

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Chalcones are naturally occurring compounds exhibiting biological activity through multiple mechanisms. Flavokawain B is one of chalcones found in kava plant. In our studies, we focused on the anticancer activity of flavokawain B in colorectal cancer cells LoVo and its resistant to doxorubicin subline—LoVo/Dx. Strong cytotoxic activity of flavokawain B and its ability to inhibit the proliferation in both cell lines was detected. These effects accompanied with induction cell cycle arrest in G2/M phase and the presence of SubG1 fraction. Flavokawain B at low concentration led to increase of caspase-3 activity. The chalcone-induced apoptosis was also confirmed by DNA fragmentation. In our work, the conversion of flavokawain B to corresponding flavanone—5,7-dimetoxyflavanone—was shown to be more extensive in cancer than in non-cancer cells. We found that the cyclization of the chalcone was related to the significant decrease in the cytotoxicity. Cell proliferation and cell cycle progression were not impaired significantly in the studied cancer cells incubated with 5,7-dimethoxyflavanone. We did not observe apoptosis in the cells incubated with flavanone. The results from biological studies agreed with the theoretical activity that emerges from structural parameters.

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Section: Discussionmentioning

confidence: 99%

Cyclization of flavokawain B reduces its activity against human colon cancer cells

et al. 2019

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“…Flavanones, including naringenin, pinocembrin and eriodictyol, are the first flavonoid products in flavonoids biosynthetic pathway. They are generally present in citrus fruits, such as grapefruit (Peterson et al, 2006), oranges (Khan et al, 2010), and lemons (Peterson et al, 2006) and have anti-inflammatory (Bano et al, 2013), antioxidant (Miranda et al, 2000), anticancer (Ketabforoosh et al, 2014), and other important pharmacological activities. The basic skeleton of flavanones is 2-phenylchromogen, which is characterized by the saturation of the C2-C3 double bond.…”

Section: Flavanonesmentioning

confidence: 99%

Metabolic Engineering of Microorganisms for the Production of Flavonoids

Sheng

Sun

Yan

et al. 2020

Front. Bioeng. Biotechnol.

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Flavonoids are a class of secondary metabolites found in plant and fungus. They have been widely used in food, pharmaceutical, and nutraceutical industries owing to their significant biological activities, such as antiaging, antioxidant, anti-inflammatory, and anticancer. However, the traditional approaches for the production of flavonoids including chemical synthesis and plant extraction involved hazardous materials and complicated processes and also suffered from low product titer and yield. Microbial synthesis of flavonoids from renewable biomass such as glucose and xylose has been considered as a sustainable and environmentally friendly method for large-scale production of flavonoids. Recently, construction of microbial cell factories for efficient biosynthesis of flavonoids has gained much attention. In this article, we summarize the recent advances in microbial synthesis of flavonoids including flavanones, flavones, isoflavones, flavonols, flavanols, and anthocyanins. We put emphasis on developing pathway construction and optimization strategies to biosynthesize flavonoids and to improve their titer and yield. Then, we discuss the current challenges and future perspectives on successful strain development for large-scale production of flavonoids in an industrial level.

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“…They were synthesized as described with some modifications (Ketabforoosh et al, 2014). To a stirred solution of chalcone (1 equiv.)…”

Section: General Procedures For the Synthesis Of Flavanones 3 4 Andmentioning

confidence: 99%

“…The reaction mixtures were heated under reflux for 6 h. and then allowed cooling to room temperature. After work-up the flavanone mixtures were purified by column chromatography using hexanes-ethyl acetate mixtures of increasing polarity (Ketabforoosh et al, 2014). The OMOM groups were hydrolyzed with 1N HCl in methanol under reflux for 15 min longer hydrolysis times lowered yield.…”

Section: General Procedures For the Synthesis Of Flavanones 3 4 Andmentioning

confidence: 99%

Biological Properties and Absolute Configuration of Flavanones From Calceolariathyrsiflora Graham

et al. 2020

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Flavanones (-)-(2S)-5,4'-dihydroxy-7-methoxyflavanone (1) and (-)-(2S)-5,3',4'trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillinresistant strain S. aureus MRSA 97-77 (MIC value of 50 µg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 µM) but 4.6and 17-fold lesser activity than etoposide and taxol.

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Synthesis and Anti‐Cancer Activity Evaluation of New Dimethoxylated Chalcone and Flavanone Analogs

Cited by 29 publications

References 27 publications

Cyclization of flavokawain B reduces its activity against human colon cancer cells

Cyclization of flavokawain B reduces its activity against human colon cancer cells

Metabolic Engineering of Microorganisms for the Production of Flavonoids

Biological Properties and Absolute Configuration of Flavanones From Calceolariathyrsiflora Graham

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