8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity

Wang, Weinan; Liang, Zhang; Wang, Shu; Shi, She‐Po; Jiang, Yong; Li, Ning; Tu, Peng‐Fei

doi:10.1016/j.foodchem.2013.10.117

Cited by 110 publications

(129 citation statements)

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“…At the A‐ring of flavan‐3‐ols, C 6 and C 8 are reactive carbons that can react with electron accepting compounds and produce many kinds of C 6 or C 8 substituted catechins. A series of N ‐ethyl‐pyrrolidinone substituted flavan‐3‐ols (EPSFs) has been isolated and identified from black, postfermented (dark tea), white, and yellow teas (Dai et al., ; Tanaka, Watarumi, Fujieda, & Kouno, ; Wang et al., ; Zhou et al., ). It is hypothesized that the Strecker degradation product of theanine is involved in the formation of N ‐ethyl‐pyrrolidinone substituted flavan‐3‐ols.…”

Section: Tea Chemistrymentioning

confidence: 99%

“…Recently, EPSFs were also identified from white and ripened pu‐erh teas, the substitution of N ‐ethyl‐2‐pyrrolidinone could be placed at the C 6 or C 8 of EGCG, EC, EGC, and ECG (Cheng et al., ; Wang et al., ; Zhou et al., ). These findings indicated that C 6 and C 8 are very reactive carbons, and then many other types of flavan‐3‐ols derivatives were also found.…”

Section: Tea Chemistrymentioning

confidence: 99%

“…Novel compounds from dark teas have been detected, some of which have been confirmed to be formed during the postfermentation step. 8‐C N ‐ethyl‐2‐pyrrolidinone substituted flavan‐3‐ols isolated from ripened pu‐erh tea are formed during the solid‐state fermentation of unfermented tea leaves (raw pu‐erh tea) (Wang et al., ). Furthermore, carboxymethyl‐ and carboxyl‐catechins, puerins A and B, teadenol A and B have also been identified in ripened pu‐erh tea (Ishimaru et al., ; Wulandari et al., ; Zhou et al., ), but whether these compounds are formed during the postfermentation step have not been clearly uncovered.…”

Section: Tea Chemistrymentioning

confidence: 99%

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Chemistry and Biological Activities of Processed Camellia sinensis Teas: A Comprehensive Review

Liang

Zhou

et al. 2019

Comp Rev Food Sci Food Safe

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360

237

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Tea is a typical processed beverage from the fresh leaves of Camellia sinensis [Camellia sinensis (L.) O. Kuntze] or Camellia assamica [Camellia sinensis var. assamica (Mast.) Kitamura] through different manufacturing techniques. The secondary metabolites of fresh tea leaves are mainly flavan‐3‐ols, phenolic acids, purine alkaloids, condensed tannins, hydrolysable tannins, saponins, flavonols, and their glycoside forms. During the processing, tea leaves go through several steps, such as withering, rolling, fermentation, postfermentation, and roasting (drying) to produce different types of tea. After processing, theaflavins, thearubigins, and flavan‐3‐ols derivatives emerge as the newly formed compounds with a corresponding decrease in concentrations of catechins. Each type of tea has its own critical process and presents unique chemical composition and flavor. The components among different teas also cause significant changes in their biological activities both in vitro and in vivo. In the present review, the progress of tea chemistry and the effects of individual unit operation on components were comprehensively described. The health benefits of tea were also reviewed based on the human epidemiological and clinical studies. Although there have been multiple studies about the tea chemistry and biological activities, most of existing results are related to tea polyphenols, especially (‐)‐epigallocatechin gallate. Other compounds, including the novel compounds, as well as isomers of amino acids and catechins, have not been explored in depth.

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Section: Tea Chemistrymentioning

confidence: 99%

Section: Tea Chemistrymentioning

confidence: 99%

Section: Tea Chemistrymentioning

confidence: 99%

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Chemistry and Biological Activities of Processed Camellia sinensis Teas: A Comprehensive Review

Liang

Zhou

et al. 2019

Comp Rev Food Sci Food Safe

Self Cite

360

237

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“…But after post-fermentation, these compounds were highly decreased compared with unfermented tea. Therefore, it was suggested the catechins’ metabolite formed in post-fermentation may contribute to the health benefits of post-fermented tea [13]. …”

Section: Introductionmentioning

confidence: 99%

Aqueous extract of post-fermented tea reverts the hepatic steatosis of hyperlipidemia rat by regulating the lipogenic genes expression and hepatic fatty acid composition

Zhou

Zhang

et al. 2014

BMC Complement Altern Med

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BackgroundPost-fermented tea has been used for the prevention of metabolic syndrome in Western China. Present study reports the biochemical mechanism of lipid-lowering effects of Jing-wei fu tea (JWFT), a variety of post-fermented tea on high-fat diet-induced hyperglycemia and obesity in rats.MethodsAqueous extract of JWFT was prepared by putting them in boiling water, and then concentrated under reduced pressure. The major compounds of JWFT were determined by high performance liquid chromatography (HPLC). High-fat diet fed rats were orally administered different doses of JWFT aqueous extract (0.5, 1.0 and 2.0 g/kg) for four weeks. At the end of this experiment, hepatic lipids, serum leptin and lipids levels were determined using enzyme-linked immunosorbent assay (ELISA). The hepatic fatty acid composition was analyzed using gas chromatography mass (GC-MS). The relative expression of lipids metabolism genes was analyzed using reverse transcriptase-polymerase chain reaction (RT-PCR).ResultsThe results showed that JWFT inhibited the increase in the body weight, abdominal adipose weight, serum lipids and hepatic lipids, and decreased serum leptin levels of high-fat diet fed rats. JWFT normalized hepatic fatty acid composition of hyperlipidemia rats by up-regulating hepatic acetyl-CoA carboxylase (ACC), stearoyl-CoA desaturase 1 (SCD1) and fatty acid synthase (FAS) gene expression, and down-regulating carnitine palmitoyl transferase-1 (CPT1). Furthermore, the results showed that JWFT inhibited the absorption of lipids.ConclusionJWFT could mitigate the obesity-induced hepatic steatosis by regulating hepatic lipogenesis and lipolysis.

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“…Flavonoids [16], theabrownin (TB) [17,18], gallic acid (GA) [19], and statin [20] have anti-obesity/hypolipidemic effects and regulate lipid metabolism. Caffeine (CAF) [21] and polysaccharides [22,23] have blood glucose-lowering effects, and 8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols [24], ethanol-soluble pigment [25], polysaccharides [23,26], and phenolic compounds [27] (including GA, (+)-catechin, (-)-epicatechin, (-)-epicatechin-3-O-gallate, (-)-epigallocatechin-3-O-gallate (-)-epiafzelechin-3-O-gallate, kaempferol, and quercetin) have antioxidant properties. However, these components are generally present in other teas (e.g., CAF and catechins), and levels of polyphenols (catechins, theaflavin, thearubigin, myricetin, quercetin, kaempferol, and flavonol glycosides), amino acids, and soluble sugars decrease during SSF of PFPT [2].…”

Section: Introductionmentioning

confidence: 99%

Isolation, Identification, and Biotransformation of Teadenol A from Solid State Fermentation of Pu-erh Tea and In Vitro Antioxidant Activity

Zhang

et al. 2016

Applied Sciences

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Post-fermented Pu-erh tea (PFPT) has several health benefits, however, little is known about the bioactive compounds. In this study, a PFPT compound was isolated by column chromatography and identified as Teadenol A by spectroscopic data analyses, including mass spectrometry and 1D and 2D NMR spectroscopy. Teadenol A in tea leaves was biotransformed by Aspergillus niger and A. tamari at 28˝C for 14 d at concentrations ranging from 9.85˘1.17 to 12.93˘0.38 mg/g. Additionally, the compound was detected in 22 commercial PFPTs at concentrations ranging from 0.17˘0.1 to 8.15˘0.1 mg/g. Teadenol A promoted the secretion of adiponectin and inhibited the expression of protein tyrosine phosphatase-1B. Antioxidant assays (e.g., 1,1-diphenyl-2-picrylhydrazyl (DPPH) scavenging activity, total antioxidant capacity (T-AOC), hydrogen donating ability, and superoxide anion radical scavenging capacity) revealed that Teadenol A has antioxidant properties. Therefore, Teadenol A is an important bio-active component of PFPT.

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8-C N-ethyl-2-pyrrolidinone substituted flavan-3-ols as the marker compounds of Chinese dark teas formed in the post-fermentation process provide significant antioxidative activity

Cited by 110 publications

References 11 publications

Chemistry and Biological Activities of Processed Camellia sinensis Teas: A Comprehensive Review

Chemistry and Biological Activities of Processed Camellia sinensis Teas: A Comprehensive Review

Aqueous extract of post-fermented tea reverts the hepatic steatosis of hyperlipidemia rat by regulating the lipogenic genes expression and hepatic fatty acid composition

Isolation, Identification, and Biotransformation of Teadenol A from Solid State Fermentation of Pu-erh Tea and In Vitro Antioxidant Activity

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