Supercritical CO2 for efficient extraction of polymethoxyflavones in Kaempferia parviflora

Wongsrikaew, Natcha; Woo, Hyun Chul; Vichitphan, Kanit; Han, Jae Hong

doi:10.1007/bf03253194

Cited by 13 publications

(13 citation statements)

References 13 publications

(12 reference statements)

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“…The ethanol extract of krachaidum is known to contain 11 PMFs, for which TLC and HPLC analyses of the compositional changes were reported before. 11 The mixture of PMFs used herein for the reaction with fecal samples contained 5,7-DMF (10%), 5,7,4′-TMF (12%), and 3,5,7,3′,4′pentamethoxyflavone (3,5,7,3′,4′-PMF, 20%) as the major compounds. Along with these three compounds, 3,5,7,4′tetramethoxyflavone (3,5,7,4′-TMF, 6%) and 5-hydroxy-3,7,4′trimethoxyflavone (5-OH-3,7,4′-TMF, 6%) were also abundant.…”

Section: ■ Resultsmentioning

confidence: 99%

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Metabolism of Kaempferia parviflora Polymethoxyflavones by Human Intestinal Bacterium Bautia sp. MRG-PMF1

Kim

Han

2014

J. Agric. Food Chem.

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Poylmethoxyflavones (PMFs) are major bioactive flavonoids, which exhibit various biological activities, such as anticancer effects. The biotransformation of PMFs and characterization of a PMF-metabolizing human intestinal bacterium were studied herein for the first time. Hydrolysis of aryl methyl ether functional groups by human fecal samples was observed from the bioconversion of various PMFs. Activity-guided screening for PMF-metabolizing intestinal bacteria under anaerobic conditions resulted in the isolation of a strict anaerobic bacterium, which was identified as Blautia sp. MRG-PMF1. The isolated MRG-PMF1 was able to metabolize various PMFs to the corresponding demethylated flavones. The microbial conversion of bioactive 5,7-dimethoxyflavone (5,7-DMF) and 5,7,4'-trimethoxyflavone (5,7,4'-TMF) was studied in detail. 5,7-DMF and 5,7,4'-TMF were completely metabolized to 5,7-dihydroxyflavone (chrysin) and 5,7,4'-trihydroxyflavone (apigenin), respectively. From a kinetics study, the methoxy group on the flavone C-7 position was found to be preferentially hydrolyzed. 5-Methoxychrysin, the intermediate of 5,7-DMF metabolism by Blautia sp. MRG-PMF1, was isolated and characterized by nuclear magnetic resonance spectroscopy. Apigenin was produced from the sequential demethylation of 5,7,4'-TMF, via 5,4'-dimethoxy-7-hydroxyflavone and 7,4'-dihydroxy-5-methoxyflavone (thevetiaflavone). Not only demethylation activity but also deglycosylation activity was exhibited by Blautia sp. MRG-PMF1, and various flavonoids, including isoflavones, flavones, and flavanones, were found to be metabolized to the corresponding aglycones. The unprecedented PMF demethylation activity of Blautia sp. MRG-PMF1 will expand our understanding of flavonoid metabolism in the human intestine and lead to novel bioactive compounds.

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Section: ■ Resultsmentioning

confidence: 99%

“…5,7-DMF and 5,7,4′-TMF were isolated according to the published method. 11 Flavonoids used for the reactivity study were purchased from Indofine Chemical Company (Hillsborough, NJ). Gifu anaerobic medium (GAM) from Nissui Pharmaceutical Co. (Tokyo, Japan) was used for isolation and growth media.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Metabolism of Kaempferia parviflora Polymethoxyflavones by Human Intestinal Bacterium Bautia sp. MRG-PMF1

Kim

Han

2014

J. Agric. Food Chem.

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“…Twelve PMFs, 5,7-dimethoxyflavone (5,7-DMF), 3,5,7-trimethoxyflavone (3,5,7-TMF), 5,7,4′-trimethoxyflavone (5,7,4′-TMF), 3,5,7,4′-tetramethoxyflavone (3,5,7,4′-TMF), 5,7,3′,4′-tetramethoxyflavone (5,7,3′,4′-TMF), 3,5,7,3′,4′-pentamethoxyflavone (3,5,7,3′,4′-PMF), 5-hydroxy-7-methoxyflavone (5-OH-7-MF), 5-hydroxy-3,7-dimethoxyflavone (5-OH-3,7-DMF), 5-hydroxy-7,4′-dimethoxyflavone (5-OH-7,4′-DMF), 5-hydroxy-3,7,4′-trimethoxyflavone (5-OH-3,7,4′-TMF), 5,3′-dihydroxy-3,7,4′-trimethoxyflavone (5,3′-diOH-3,7,4′-TMF), and 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (5-OH-3,7,3′,4′-TMF), were isolated and purified from K. parvif lora. 24 Alkyl derivatives of PMF, 5,3′-dihydroxy-3,7,4′-triethylquercetin (5,3′-diOH-3,7,4′-TEF), 5-hydroxy-3,7,3′,4′-tetrapropylquercetin (5-OH-3,7,3′,4′-TPF), and 3,5,7,3′,4′-pentaethoxyflavone (3,5,7,3′,4′-PEF), were synthesized from quercetin, according to a published method (Figure 1). 25 Syringic acid and vanillic acid were purchased from Sigma-Aldrich Korea (Seoul, Korea spectrometry (98%) was purchased from Fluka (Buchs, Switzerland).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

Demethylation of Polymethoxyflavones by Human Gut Bacterium, Blautia sp. MRG-PMF1

Burapan

Kim

Han

2017

J. Agric. Food Chem.

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Polymethoxyflavones (PMFs) were biotransformed to various demethylated metabolites in the human intestine by the PMF-metabolizing bacterium, Blautia sp. MRG-PMF1. Because the newly formed metabolites can have different biological activities, the pathways and regioselectivity of PMF bioconversion were investigated. Using an anaerobic in vitro study, 12 PMFs, 5,7-dimethoxyflavone (5,7-DMF), 5-hydroxy-7-methoxyflavone (5-OH-7-MF), 3,5,7-trimethoxyflavone (3,5,7-TMF), 5-hydroxy-3,7-dimethoxyflavone (5-OH-3,7-DMF), 5,7,4'-trimethoxyflavone (5,7,4'-TMF), 5-hydroxy-7,4'-dimethoxyflavone (5-OH-7,4'-DMF), 3,5,7,4'-tetramethoxyflavone (3,5,7,4'-TMF), 5-hydroxy-3,7,4'-trimethoxyflavone (5-OH-3,7,4'-TMF), 5,7,3',4'-tetramethoxyflavone (5,7,3',4'-TMF), 3,5,7,3',4'-pentamethoxyflavone (3,5,7,3',4'-PMF), 5-hydroxy-3,7,3',4'-tetramethoxyflavone (5-OH-3,7,3',4'-TMF), and 5,3'-dihydroxy-3,7,4'-trimethoxyflavone (5,3'-diOH-3,7,4'-TMF), were converted to chrysin, apigenin, galangin, kaempferol, luteolin, and quercetin after complete demethylation. The time-course monitoring of PMF biotransformations elucidated bioconversion pathways, including the identification of metabolic intermediates. As a robust flavonoid demethylase, regioselectivity of PMF demethylation generally followed the order C-7 > C-4' ≈ C-3' > C-5 > C-3. PMF demethylase in the MRG-PMF1 strain was suggested as a Co-corrinoid methyltransferase system, and this was supported by the experiments utilizing other methyl aryl ether substrates and inhibitors.

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“…5-Hydroxy-7-methoxyflavone (HMF) was isolated from Kaemperia parviflora by using the supercritical CO 2 fluid extraction method. Optimal conditions of 200 bar of CO 2 and 50°C were used for isolation of HMF, and structure was elucidated by UV-Vis and 1 H NMR spectroscopic data analysis [ 17 ]. HMF was dissolved in 5% DMSO, and a concentration range of 25–100 μM was used for experimental analysis.…”

Section: Methodsmentioning

confidence: 99%

5-Hydroxy-7-Methoxyflavone Triggers Mitochondrial-Associated Cell Death via Reactive Oxygen Species Signaling in Human Colon Carcinoma Cells

et al. 2016

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Plant-derived compounds are an important source of clinically useful anti-cancer agents. Chrysin, a biologically active flavone found in many plants, has limited usage for cancer chemotherapeutics due to its poor oral bioavailability. 5-Hydroxy-7-methoxyflavone (HMF), an active natural chrysin derivative found in various plant sources, is known to modulate several biological activities. However, the mechanism underlying HMF-induced apoptotic cell death in human colorectal carcinoma cells in vitro is still unknown. Herein, HMF was shown to be capable of inducing cytotoxicity in HCT-116 cells and induced cell death in a dose-dependent manner. Treatment of HCT-116 cells with HMF caused DNA damage and triggered mitochondrial membrane perturbation accompanied by Cyt c release, down-regulation of Bcl-2, activation of BID and Bax, and caspase-3-mediated apoptosis. These results show that ROS generation by HMF was the crucial mediator behind ER stress induction, resulting in intracellular Ca2+ release, JNK phosphorylation, and activation of the mitochondrial apoptosis pathway. Furthermore, time course study also reveals that HMF treatment leads to increase in mitochondrial and cytosolic ROS generation and decrease in antioxidant enzymes expression. Temporal upregulation of IRE1-α expression and JNK phosphorylation was noticed after HMF treatment. These results were further confirmed by pre-treatment with the ROS scavenger N-acetyl-l-cysteine (NAC), which completely reversed the effects of HMF treatment by preventing lipid peroxidation, followed by abolishment of JNK phosphorylation and attenuation of apoptogenic marker proteins. These results emphasize that ROS generation by HMF treatment regulates the mitochondrial-mediated apoptotic signaling pathway in HCT-116 cells, demonstrating HMF as a promising pro-oxidant therapeutic candidate for targeting colorectal cancer.

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Supercritical CO2 for efficient extraction of polymethoxyflavones in Kaempferia parviflora

Cited by 13 publications

References 13 publications

Metabolism of Kaempferia parviflora Polymethoxyflavones by Human Intestinal Bacterium Bautia sp. MRG-PMF1

Metabolism of Kaempferia parviflora Polymethoxyflavones by Human Intestinal Bacterium Bautia sp. MRG-PMF1

Demethylation of Polymethoxyflavones by Human Gut Bacterium, Blautia sp. MRG-PMF1

5-Hydroxy-7-Methoxyflavone Triggers Mitochondrial-Associated Cell Death via Reactive Oxygen Species Signaling in Human Colon Carcinoma Cells

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