Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

Sang, Shengmin; Lambert, Joshua D.; Tian, Shiying; Hong, Jungil; Hou, Zhe; Ryu, Jae He; Stark, Ruth E.; Rosén, Robert; Huang, Mou Tuan; Yang, Chung S.; Ho, Chi Tang

doi:10.1016/j.bmc.2003.10.024

Cited by 128 publications

(85 citation statements)

References 36 publications

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“…Although both extracts are rich sources of catechins, they can constitute up to 30% of the dry tea leaf weight [29,31]. In an incubation system utilizing Tea leaf extract as starting material, the theaflavin synthesis capacity of the homogenates were in decreasing order ; Incubation of fresh green tea leaves and Lipton® Green tea extract using the other sources of polyphenol oxidase enzymes investigated in this study, gave similar results.…”

Section: Resultssupporting

confidence: 67%

“…Furthermore, theaflavins have been implicated to have antiviral- [7], anticancer- [20], antimutagenic-, anticlastogenic- [13], antibacterial activity [25], antiobesity and lipid lowering effects [17] and even inhibit HIV-1 infection [42]. Despite their potential clinical significance in various fields, research on theaflavins has been hampered due to their unavailability, to such an extent that most previous research was focused on the use of theaflavins mixtures [29].…”

Section: Introductionmentioning

confidence: 99%

“…From the 15-30% dry weight of catechins present in green tea shoots, only 0.4-1.9% dry weight of theaflavins are formed during black tea manufacture [29,31]. For this reason, various approaches have been employed for the synthesis of theaflavins from substrate materials, including fresh tea leaves [34], tea leaf juice, processed green tea leaves, green tea slurry [11], liquid green tea extract [16] and in vitro modelling of fermentation with purified catechins [27].…”

Section: Introductionmentioning

confidence: 99%

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Alternative pathway implicated as an influencing factor in the synthesis of theaflavin

Westhuizen

Steenkamp

et al. 2015

Biocatalysis and Biotransformation

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The principal pigments present in black tea, theaflavins, have been indicated to be of potential clinical significance in various fields of research which has been hampered by the very low levels of theaflavins from black tea extractions, being the original method employed to acquire theaflavins. Forelle pear (44 µM Theaflavin/g dry weight/hr) and Yacon leaf (65 µM Theaflavin/g dry weight/hr) homogenates were tested for their theaflavin synthesis capacity and found to have a larger theaflavin synthesis capacity than a green tea leaf homogenate (26 µM Theaflavin/g dry weight/hr) based upon the flavognost method. In an incubation system of green tea leaf extract utilizing endogenous enzymes present in Forelle pear and Yacon homogenates to synthesise theaflavin, the formation of an unknown peak (m/z 563.1349; (23.95) 5 ; C 26 H 28 O 14 ) was detected by mass spectrometry with a molecular mass similar to theaflavin. This is in contrast to theaflavin being solely synthesised in an in vitro model incubation system using isolated catechins and purified Forelle pear polyphenol oxidase. The preferential formation of the unknown compound could explain the low levels of theaflavins in black tea.

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Section: Resultssupporting

confidence: 67%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Alternative pathway implicated as an influencing factor in the synthesis of theaflavin

Westhuizen

Steenkamp

et al. 2015

Biocatalysis and Biotransformation

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“…The ability of EGCG and AcEGCG to inhibit the release of arachidonic acid and production of NO by lipopolysaccharide (LPS)-stimulated murine macrophages was determined using previously described methods (Sang et al, 2004). In brief, to determine arachidonic acid release, RAW264.7 cells were incubated overnight with 0.1 Ci/ml [5,6,8,9,11,12,14,15-3 H](N)-arachidonic acid to allow membrane incorporation.…”

Section: Methodsmentioning

confidence: 99%

Peracetylation as a Means of Enhancing in Vitro Bioactivity and Bioavailability of Epigallocatechin-3-Gallate

et al. 2006

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ABSTRACT:(؊)-Epigallocatechin-3-gallate (EGCG) is the widely studied catechin in green tea (Camellia sinensis). Previously, we have reported the low bioavailability of EGCG in rats and mice. As a means of improving the bioavailability of EGCG, we have prepared a peracetylated EGCG derivative (AcEGCG) and herein report its growth inhibitory activity and cellular uptake in vitro, as well as bioavailability in mice. AcEGCG exhibited enhanced growth inhibitory activity relative to EGCG in both KYSE150 human esophageal (IC 50

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“…19 In the human setting, we have demonstrated that fetuses exposed to a maternal diet rich in polyphenols in the third trimester show higher ductal velocities and lower pulsatility indexes (PIs), as well as larger right ventricles, than those exposed to minimal amounts of these substances. 15,16 The rationale for understanding the behavior of fetal ductal arteriosus flow dynamics after maternal ingestion of PRF in late pregnancy is that these substances have definite anti-inflammatory and antioxidant effects, largely reported in the literature, [20][21][22][23][24][25][26][27][28][29] based on the inhibition of cyclooxygenase-2 or other components of the metabolic cascade resulting in prostaglandins biosynthesis. These actions are similar to that involved in prostaglandin inhibition caused by NSAID.…”

Section: Introductionmentioning

confidence: 99%

Reversal of fetal ductal constriction after maternal restriction of polyphenol-rich foods: an open clinical trial

et al. 2011

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Objective: To test the hypothesis that maternal restriction of polyphenolrich foods (PRF), which, like non-steroidal anti-inflammatory drugs (NSAID), inhibit prostaglandin synthesis in the third trimester, reverse fetal ductal constriction (DC). Study Design:An open clinical trial of 51 third trimester fetuses with DC with no history of NSAID intake was designed. All mothers were submitted to a food frequency questionnaire and were oriented to withdrawl PRF, being reassessed after 3 weeks. Doppler parameters were assessed before and after discontinuation of these substances. A control group of 26 third trimester normal fetuses, with no ductus arteriosus (DA) constriction, in which no dietary intervention was offered, was reviewed after 3 weeks. Student's t-test and Wilcoxon's test were used.Result: Mean gestational age was 32±3 weeks (28 to 37 weeks). After discontinuation of PRF (X3 weeks), 48/51 fetuses (96%) showed complete reversal of DC, with decrease in mean ductal systolic velocity (1.74 ± 0.20 m s À1 to 1.31 ± 0.34 m s À1 , P<0.001), mean diastolic velocity (0.33±0.09 m s À1 to 0.21±0.07 m s À1 , P<0.001) and mean right to left ventricular dimension ratio (1.37 ± 0.26 to 1.12 ± 0.17, P<0.001) and increase in mean ductal pulsatility index (PI) (1.98 ± 0.36 to 2.46±0.23, P<0.001). Median daily maternal consumption of PRF was 286 mg per day and decreased after orientation to 0 mg per day, P<0.001. In the control group, with GA of 32±4 w (29-37 w), there was no significant differences in median daily maternal consumption of PRF, mean ductal systolic velocitiy, diastolic velocity, PI and right ventricular to left ventricular diameter ratio (RV/LV) ratio. Keywords: fetal ductal constriction; prostaglandins; pulmonary hypertension; polyphenol-rich foods Introduction Ductal constriction (DC) has long been related to inhibition of the prostaglandin synthesis pathway, mainly as a result of maternal intake of non-steroidal anti-inflammatory drugs (NSAID) in the third trimester of pregnancy. 1-5 Constriction of fetal ductus arteriosus (DA) is a risk factor for pulmonary hypertension in the newborn period, with its known severe consequences. [6][7][8][9][10][11] For several years, many reports have been discussing the high prevalence of DC in the absence of a known trigger effect. 11 It has been discussed that other extrinsic factors, in addition to NSAID, could be involved in the genesis of this important clinical situation. 1,12,13 We and others have already suggested that maternal ingestion of polyphenol-rich foods (PRF) in late pregnancy, such as herbal teas, grape juice, dark chocolate and others, could be associated to fetal DC. [14][15][16][17][18] Experimental studies in fetal lambs have supported this hypothesis, showing a cause and effect relationship of maternal consumption of green tea and other polyphenol-rich substances with constriction of fetal DA in the animal model. 19 In the human setting, we have demonstrated that fetuses exposed to a maternal diet rich in polyphenols in the third trimester show h...

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Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities

Cited by 128 publications

References 36 publications

Alternative pathway implicated as an influencing factor in the synthesis of theaflavin

Alternative pathway implicated as an influencing factor in the synthesis of theaflavin

Peracetylation as a Means of Enhancing in Vitro Bioactivity and Bioavailability of Epigallocatechin-3-Gallate

Reversal of fetal ductal constriction after maternal restriction of polyphenol-rich foods: an open clinical trial

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