3,4-Dihydroxyphenylacetic acid is a predominant biologically-active catabolite of quercetin glycosides

Tang, Yue; Nakashima, Sayaka; Saiki, Shunya; Myoi, Yui; Abe, Naomi; Kuwazuru, Shoko; Zhu, Beiwei; Ashida, Hitoshi; Murata, Yoshiyuki; Nakamura, Yoshimasa

doi:10.1016/j.foodres.2016.09.034

Cited by 56 publications

(56 citation statements)

References 37 publications

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“…Ferrous ion oxidation‐xylenol orange method was used to determine the change of hydrogen peroxide levels during the ACE activity assay. Different concentrations (0, 5, 10, 50, and 100 μM) of EGCg was incubated with recombinant human ACE at 37°C for 30 min.…”

Section: Methodssupporting

confidence: 90%

(−)-Epigallocatechin-3-gallate inhibits human angiotensin-converting enzyme activity through an autoxidation-dependent mechanism

Liu

Nakashima

Nakamura

et al. 2017

J Biochem Mol Toxicol

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We investigated the molecular mechanisms involved in the angiotensin-converting enzyme (ACE) inhibition by (-)-epigallocatechin-3-gallate (EGCg), a major tea catechin. EGCg inhibited both the ACE activity in the lysate of human colorectal cancer cells and human recombinant ACE (rh-ACE) in a dose-dependent manner. Co-incubation with zinc sulfate showed no influence on the rh-ACE inhibition by EGCg, whereas it completely counteracted the inhibitory effect of ethylenediaminetetraacetic acid, a chelating-type ACE inhibitor. Although hydrogen peroxide was produced by the autoxidation of EGCg, hydrogen peroxide itself had little effect on the ACE activity. Conversely, the co-incubation of EGCg with borate or ascorbic acid significantly diminished the EGCg inhibition. A redox-cycling staining experiment revealed that rh-ACE was covalently modified by EGCg. A Lineweaver-Burk plot analysis indicated that EGCg inhibited the ACE activity in a non-competitive manner. These results suggested that EGCg might allosterically inhibit the ACE activity through oxidative conversion into an electrophilic quinone.

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Section: Methodssupporting

confidence: 90%

(−)-Epigallocatechin-3-gallate inhibits human angiotensin-converting enzyme activity through an autoxidation-dependent mechanism

Liu

Nakashima

Nakamura

et al. 2017

J Biochem Mol Toxicol

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“…In O. basilicum, there were also antioxidant activities in leaf extracts, and this might be attributed to major identified polyphenols including rosmarinic acid, DOPAC and rutoside. DOPAC, has known antioxidant activities as revealed in previous studies [55]. Rutoside (rutin) is known also as potent antioxidant [56].…”

Section: Discussionmentioning

confidence: 81%

Saudi Rosmarinus officinalis and Ocimum basilicum L. Polyphenols and Biological Activities

et al. 2020

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Investigating the polyphenolic profile of natural Rosmarinus officinalis and Ocimum basilicum populations may reveal essential compounds that have biological activities. Natural populations of R. officinalis and O. basilicum in Northern Riyadh were investigated by HPLC-DAD analyses. Several polyphenols, including rosmarinic acid, gentisic acid, 3,4-dihydroxyphenylacetic acid, rutoside, and others, out of 38 screened were confirmed. Rosmarinic acid was the major polyphenol in both of R. officinalis and O. basilicum. R. officinalis methanolic leaf extracts contained other phenols such as gentisic acid while O. basilicum contained also 3,4-dihydroxyphenylacetic acid and rutoside as well as others. R. officinalis showed higher antioxidant activities than O. basilicum using 2,2-diphenyl-1-picrylhydrazyl (DPPH), ferric reducing antioxidant power (FRAP), and β-carotene bleaching assays. These higher activities are associated with a higher composition of rosmarinic acid in leaf extracts. The antioxidant activities of O. basilicum were attributed to identified phenols of rosmarinic acid, 3,4-dihydroxyphenylacetic acid, and rutoside. There were antiproliferative and cytotoxic activities of leaf extracts, as well as identified polyphenols, against several cancer cells. These activities were attributed to the accumulation of necrotic and apoptotic cells in treated cancer cells with leaf extracts as well as identified polyphenols. The antibacterial and antifungal activities of leaf extracts were mainly attributed to 3,4-dihydroxyphenylacetic acid and rutoside in O. basilicum and rosmarinic acid and caffeic acid in R. officinalis. This study proved that R. officinalis and O. basilicum natural populations might be considered as promising sources of natural polyphenols with biological activities.

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“…Ring-fission catabolism has been observed in the case of tea catechins, the primary class of flavonoids in green tea; γ-valerolactones have been identified in human urine after green tea ingestion ( Figure 2 targets of covalent modification by DOPAC in mouse hepatoma cells [77]. Thus, even though DOPAC shows relatively weaker biological activities than quercetin aglycon [72,76], DOPAC is quite plausibly a main component that facilitates the health-promoting potential of quercetin glycosides. DOPAC also has advantages for application as a food chemical because it has lower cytotoxicity than quercetin.…”

Section: Ring-fission Products Of Polyphenolsmentioning

confidence: 99%

“…DOPAC has recently been identified as the most active phenolic acid derived from quercetin glycosides, in terms of free radical scavenging and induction of drug metabolic enzymes [72]. In addition to its free radical scavenging activity, DOPAC inhibits the secretion of pro-inflammatory cytokines in mononuclear cells [73] and the expression of P-selectin in platelets [74].…”

Section: Metabolic Pathways Of Isoflavone Metabolitesmentioning

confidence: 99%

“…DOPAC, as well as OPAC and 3′-methoxy-4′-hydroxyphenylacetic acid, inhibit the formation of advanced glycation end-products and oxidative stress-induced neuronal cell death [75]. Furthermore, DOPAC significantly inhibits hydrogen peroxide-induced cytotoxicity in rat normal hepatocytes, dependent on the expression of phase 2 cytoprotective enzymes, such as hemeoxynegese-1 and glutathione S-transferase, and independent of its free radical scavenging potential [72]. DOPAC also enhances not only total aldehyde dehydrogenase (ALDH) activity, but also gene and protein expression of ALDH isozymes in mouse hepatoma Hepa1c1c7 cells [76].…”

Section: Metabolic Pathways Of Isoflavone Metabolitesmentioning

confidence: 99%

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Flavonoid metabolism: the interaction of metabolites and gut microbiota

Murota

Nakamura

Uehara

2018

Bioscience, Biotechnology, and Biochemistry

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Several dietary flavonoids exhibit anti-oxidative, anti-inflammatory, and anti-osteoporotic activities relevant to prevention of chronic diseases, including lifestyle-related diseases. Dietary flavonoids (glycoside forms) are enzymatically hydrolyzed and absorbed in the intestine, and are conjugated to their glucuronide/sulfate forms by phase II enzymes in epithelial cells and the liver. The intestinal microbiota plays an important role in the metabolism of flavonoids found in foods. Some specific products of bacterial transformation, such as ring-fission products and reduced metabolites, exhibit enhanced properties. Studies on the metabolism of flavonoids by the intestinal microbiota are crucial for understanding the role of these compounds and their impact on our health. This review focused on the metabolic pathways, bioavailability, and physiological role of flavonoids, especially metabolites of quercetin and isoflavone produced by the intestinal microbiota.

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3,4-Dihydroxyphenylacetic acid is a predominant biologically-active catabolite of quercetin glycosides

Cited by 56 publications

References 37 publications

(−)-Epigallocatechin-3-gallate inhibits human angiotensin-converting enzyme activity through an autoxidation-dependent mechanism

(−)-Epigallocatechin-3-gallate inhibits human angiotensin-converting enzyme activity through an autoxidation-dependent mechanism

Saudi Rosmarinus officinalis and Ocimum basilicum L. Polyphenols and Biological Activities

Flavonoid metabolism: the interaction of metabolites and gut microbiota

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