Microbial Transformation of Licochalcones

Xiao, Yina; Han, Fubo; Lee, Ik‐Soo

doi:10.3390/molecules25010060

Cited by 7 publications

(6 citation statements)

References 32 publications

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“…Biocatalysis is considered to be green and eco-friendly technology, which has sustainable development prospects [17]. Since 2000, a variety of microorganisms have exhibited abilities to convert flavonoids, and some microorganisms were also found to naturally and directly synthesize flavonoids as a result of their own endogenous metabolism [18]. The biocatalytic production of flavonoids offers many advantages, such as fast production, low environmental pollution, and large-scale production.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Flavonoids Improves Antimicrobial and Anti-Breast Cancer Activities In Vitro

Hao

Wei

Wang

et al. 2021

Foods

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Coarse cereals are rich in flavonoids, which are bioactive substances with a wide range of functions. Biotransformation is considered an emerging approach to methylate flavonoids, displaying prominent regio- and stereoselectivity. In the current study, liquiritigenin, naringenin, and hesperidin flavonoids were biotransformed using O-methyltransferases that were heterologously expressed in Saccharomyces cerevisiae BJ5464-NpgA. Nuclear magnetic resonance (NMR) spectroscopy was used together with high-resolution mass spectroscopy analysis to determine the structures of the resulting methylated transformants, and their antimicrobial and antiproliferation activities were also characterized. Among the five methylated flavonoids obtained, 7-methoxy-liquiritigenin had the strongest inhibitory effect on Candida albicans SC5314 (C. albicans SC5314), Staphylococcus aureus ATCC6538 (S. aureus ATCC6538), and Escherichia coli ATCC25922 (E. coli ATCC25922), which increased 7.65-, 1.49-, and 0.54-fold in comparison to the values of their unmethylated counterparts at 200, 250, and 400 μM, respectively. The results suggest that 3’-methoxyhesperetin showed the best antiproliferative activity against MCF-7 cells with IC50 values of 10.45 ± 0.45 µM, which was an increase of more than 14.35-fold compared to that of hesperetin. These results indicate that methylation enhances the antimicrobial activities and antiproliferative effects of flavonoids. The current study provides an experimental basis for further research on flavonoids as well as flavonoid-containing crops in the development of antimicrobial and anti-breast cancer drugs in addition to supplementary and health foods. The biotransformation method is ideal, as it represents a means for the sustainable production of bioactive flavonoids.

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Section: Introductionmentioning

confidence: 99%

Biotransformation of Flavonoids Improves Antimicrobial and Anti-Breast Cancer Activities In Vitro

Hao

Wei

Wang

et al. 2021

Foods

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“…IR spectra characteristically revealed the existence of peaks for conjugated carbonyl groups at 1658 cm −1 . 1 H NMR spectra obviously showed two doublet signals corresponding to the vinyl protons CH = CH–CO with coupling constant 15.6–15.7 Hz indicating trans configuration 46 , 47 . Also, 13 C NMR spectra showed the presence of carbonyl carbon at δ 188.4–188.9 ppm along with trans olefinic carbons at δ 144.2–143.9 and δ 121.2–121.6 ppm.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of halogenated phenoxychalcones and their corresponding pyrazolines as cytotoxic agents in human breast cancer

Halim

Hassan

Mohamed

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Novel halogenated phenoxychalcones 2a–f and their corresponding N -acetylpyrazolines 3a–f were synthesised and evaluated for their anticancer activities against breast cancer cell line (MCF-7) and normal breast cell line (MCF-10a), compared with staurosporine. All compounds showed moderate to good cytotoxic activity when compared to control. Compound 2c was the most active, with IC 50 = 1.52 µM and selectivity index = 15.24. Also, chalcone 2f showed significant cytotoxic activity with IC 50 = 1.87 µM and selectivity index = 11.03. Compound 2c decreased both total mitogen activated protein kinase (p38α MAPK) and phosphorylated enzyme in MCF-7 cells, suggesting its ability to decrease cell proliferation and survival. It also showed the ability to induce ROS in MCF-7 treated cells. Compound 2c exhibited apoptotic behaviour in MCF-7 cells due to cell accumulation in G2/M phase and elevation in late apoptosis 57.78-fold more than control. Docking studies showed that compounds 2c and 2f interact with p38alpha MAPK active sites.

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“…During our previous study, it was observed that licochalcones B, C, H could be O-glucosylated by using the fungus M. hiemalis [27]. Here, the same process was performed with LCA and XN, which led to the isolation of a new compound licochalcone A 4-O-β-D-glucopyranoside (6) together with a known compound xanthohumol 4 -O-β-D-glucopyranoside [28].…”

Section: Microbial Transformation Of Licochalcone a And Xanthohumol By M Hiemalismentioning

confidence: 97%

“…To the best of our knowledge, no metabolism studies of licochalcones B-D and H were performed so far, except the study previously carried out in this lab [27]. Thus, in order to identify the conjugated metabolites of licochalcones, further studies need to be performed.…”

Section: Introductionmentioning

confidence: 99%

Microbial Conjugation Studies of Licochalcones and Xanthohumol

Han

Xiao

Lee

2021

IJMS

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Microbial conjugation studies of licochalcones (1–4) and xanthohumol (5) were performed by using the fungi Mucor hiemalis and Absidia coerulea. As a result, one new glucosylated metabolite was produced by M. hiemalis whereas four new and three known sulfated metabolites were obtained by transformation with A. coerulea. Chemical structures of all the metabolites were elucidated on the basis of 1D-, 2D-NMR and mass spectroscopic data analyses. These results could contribute to a better understanding of the metabolic fates of licochalcones and xanthohumol in mammalian systems. Although licochalcone A 4′-sulfate (7) showed less cytotoxic activity against human cancer cell lines compared to its substrate licochalcone A, its activity was fairly retained with the IC50 values in the range of 27.35–43.07 μM.

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Microbial Transformation of Licochalcones

Cited by 7 publications

References 32 publications

Biotransformation of Flavonoids Improves Antimicrobial and Anti-Breast Cancer Activities In Vitro

Biotransformation of Flavonoids Improves Antimicrobial and Anti-Breast Cancer Activities In Vitro

Synthesis and biological evaluation of halogenated phenoxychalcones and their corresponding pyrazolines as cytotoxic agents in human breast cancer

Microbial Conjugation Studies of Licochalcones and Xanthohumol

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