Optimization of Technical Parameters for Chemical Synthesis of Theasinensin A by PBD and RSM

ZHANG Jianyong; CHEN Lin; CUI Hongchun; WANG Weiwei; XUE Jinjin; XIONG Chunhua; JIANG Heyuan

doi:10.13305/j.cnki.jts.20200117.002

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Journal of Tea Science ›› 2020, Vol. 40 ›› Issue (1) : 51-62. DOI: 10.13305/j.cnki.jts.20200117.002

Optimization of Technical Parameters for Chemical Synthesis of Theasinensin A by PBD and RSM

ZHANG Jianyong^1,2, CHEN Lin², CUI Hongchun³, WANG Weiwei², XUE Jinjin², XIONG Chunhua^1,*, JIANG Heyuan^2,*

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Abstract

The effect of chemical synthesis conditions on the yield of theasinensin A was studied. Key factors for chemical synthesis of theasinensin A (TSA) were determined by single factor test and Plackett-Burman Design (PBD). The response surface methodology (RSM) was employed to optimize the technical parameters for the chemical synthesis. The experiment results indicate that the effects of copper oxide content, methanol content and temperature on the yield were extremely significant. The main factors were methanol content, next copper oxide content, and then temperature. The optimal conditions were as follows: copper chloride content 43%, methanol content 26%, and temperature 15℃. Under these conditions, the yield of TSA was 59.12%, which was close to the predicted value of 59.34%. The combination of PBD and RSM to optimize the chemical synthesis of TSA achieved ideal result, which could provide reference and theoretical basis for the efficient chemical synthesis of other catechin oxidation polymers.

Key words

chemical synthesis / EGCG / optimization / PBD / RSM / theasinensin A (TSA)

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ZHANG Jianyong, CHEN Lin, CUI Hongchun, WANG Weiwei, XUE Jinjin, XIONG Chunhua, JIANG Heyuan. Optimization of Technical Parameters for Chemical Synthesis of Theasinensin A by PBD and RSM[J]. Journal of Tea Science. 2020, 40(1): 51-62 https://doi.org/10.13305/j.cnki.jts.20200117.002

References

[1] Shii T, Tanaka T, Watarumi S, et al.Polyphenol composition of a functional fermented tea obtained by tea-rolling processing of green tea and loquat leaves[J]. Journal of Agricultural and Food Chemistry, 2011, 59(13): 7253-7260.
[2] Roberts E A H, Cartwright R A, Oldschool M. The phenolic substance of manufactured tea.Ⅰ.—Fractionation and paper chromatography of water-soluble substances[J]. Journal of the Science of Food and Agriculture, 1957, 8(2): 72-80.
[3] Roberts E A H, Williams D M. The phenolic substance of manufactured tea.Ⅳ.—Enzymic oxidations of individual substrates[J]. Journal of the Science of Food and Agriculture, 1959, 10(3): 167-172.
[4] Nonaka G, Kawahara O, Nishioka I.Tannins and related compounds XV. A new class of dimeric flavan-3-ol gallates, theasinensin A and theasinensin B, and proanthocyanidin gallates from green tea leaf[J]. Chemical and Pharmaceutical Bulletin, 1983, 31(11): 3906-3914.
[5] Hashimoto F, Nonaka G, Nishioka I.Tannins and related compounds. LXIX. Isolation and structure elucidation of B,B’-linked bisflavanoids, theasinensin D-G and oolongtheanin from oolong tea[J]. Chemical and Pharmaceutical Bulletin, 1988, 36(5): 1676-1684.
[6] Shibamoto T, Terao J, Osawa T, et al.Functional foods for disease prevention I[C]. Washington: American Chemical Society, 1998: 209-216.
[7] Morello M J, Shahidi F, Ho C T.Free radicals in food[C]. Washington: American Chemical Society, 2002: 213-223.
[8] Hashimoto F, Ono M, Masuoka C, et al.Evaluation of the anti-oxidative effect (in vitro) of tea polyphones[J]. Journal of the Agricultural Chemical Society of Japan, 2003, 67(2): 396-401.
[9] Pan M, Lai C, Wang H, et al.Black tea in chemo-prevention of cancer and other human diseases[J]. Food Science and Human Wellness, 2013, 2(1): 12-21.
[10] Shibu, M A, Kuo C H, Chen B C, et al. Oolong tea prevents cardiomyocyte loss against hypoxia by attenuating p-JNK mediated hypertrophy and enhancing P-IGF1R, p-akt, and p-Badser136 activity and by fortifying NRF2 antioxidation system[J]. Environmental Toxicology, 2018, 33(2): 220-233.
[11] Saeki K, Sano M, Miyase T, et al.Apoptosis-inducing activity of polyphenol compounds derived from tea catechins in human histiolytic lymphoma U937 cell[J]. Bioscience, Biotechnology, and Biochemistry, 1999, 63(3): 585-587.
[12] Pan M H, Liang Y C, Lin-Shiau S Y, et al. Induction of apoptosis by the oolong tea polyphenol theasinensin A through cytochrome c release and activation of caspase-9 and caspase-3 in human U937 cells[J]. Journal of Agricultural and Food Chemistry, 2000, 48(12): 6337-6346.
[13] Shahidi F, Ho C T, Watanabe S, et al.Food factors in health promotion and disease prevention[C]. Washington: American Chemical Society, 2003: 50-71.
[14] Hou D X, Masuzaki S, Tanigawa S, et al.Oolong ea theasinensins attenuate cyclooxygenase-2 expression in lipopolysaccharide (LPS)-activated mouse macrophages: structure-activity relationship and molecular mechanisms[J]. Journal of Agricultural and Food Chemistry, 2010, 58(24): 12735-12743.
[15] Chen J H, Qin S, Xiao J P, et al.A genome-wide microarray highlights the antiinflammatory genes targeted by Oolong tea theasinensin A in macrophages[J]. Nutrition and Cancer, 2001, 63(7): 1064-1073.
[16] Hatano T, Kusuda1 M, Hori M, et al. Theasinensin A, a tea polyphenol formed from (-)-epigallocatechin gallate, suppresses antibiotic resistance of methicillin-resistant staphylococcus aureus[J]. Planta Medica, 2003, 69(11): 984-989.
[17] Taylor P W, Hamilton-Miller J, Stapleton P D.Antimicrobial properties of green tea catechins[J]. Food Science & Technology Bulletin, 2005, 16(2): 71-81.
[18] Isaacs C E, Xu W, Merz G, et al.Digallate dimers of (-)-epigallocatechin gallate inactivateb herpes simplex virus[J]. Antimicrobial Agents and Chemotherapy, 2011, 55(12): 5646-5653.
[19] 施莉婷, 江和源, 张建勇, 等. 茶叶中聚酯型儿茶素酶促合成机制和生物学活性研究进展[J]. 食品安全质量检测学报,2018, 9(2): 223-228.
Shi L T, Jiang H Y, Zhang J Y, et al.Review on enzymatic synthesis mechanism and functional activity of theasinensins[J]. Journal of Food Safety & Quality, 2018, 9(2): 223-228.
[20] Miyata Y, Tamaru S, Tanaka T, et al.Theaflavins and theasinensin A direved from fermented tea have antiyperglycemic and hypotricylglycerolemic effects in KK-Ay mice and sprague-dawley rats[J]. Journal of Agricultural and Food Chemistry, 2013, 61(39): 9366-9372.
[21] Tanaka Y, Kirita M, Miyata S, et al.O-Methylated theaflavins suppress the intracellular accumulation of triglycerides from terminally differentiated human visceral adipocytes[J]. Journal of Agricultural and Food Chemistry, 2013, 61(51): 12634-12639.
[22] Nakai M, Fukui Y, Asami S, et al.Inhibitory effects of Oolong tea polyphenols on pancreatic lipase in vitro[J]. Journal of Agricultural and Food Chemistry, 2005, 53(11): 4593-4598.
[23] Zhang H, Qi R, Mine Y.The impact of oolong and black tea polyphenols on human health[J]. Food Bioscience, 2019, 29: 55-61.
[24] Miyata Y, Tanaka T, Tamaya K, et al.Cholesterol-Lowering effect of black tea polyphenols, theaflavins, theasinensin A and thearubigins[J]. Food Science and Technology Research, 2011, 17(6): 585-588.
[25] Toshima A, Matsui T, Noguchi M, et al.Identification of α-glucosidase inhibitors from a new fermented tea obtained by tea-rolling processing of loquat (Eriobotrya japonica) and green tea leaves[J]. Journal of the Science of Food and Agriculture, 2010, 90(9): 1545-1550.
[26] Hung W L, Yang G, Wang Y C, et al.Protective effects of theasinensin A against carbon tetrachloride-induced liver injury in mice[J]. Food & Function, 2017, 8(9): 3276-3287.
[27] 徐斌, 薛金金, 江和源, 等. 茶叶中聚酯型儿茶素研究进展[J]. 茶叶科学, 2014, 34(4): 315-323.
Xu B, Xue J J, Jiang H Y, et al.Review on theasinensins in tea[J]. Journal of Tea Science, 2014, 34(4): 315-323.
[28] Tanaka T, Watarumi S, Matsuo Y, et al.Production of theasinensins A and D, epigallocatechin gallate dimers of black tea, by oxidation-reduction dismutation of dehydrotheasinensin A[J]. Tetrahedron, 2003, 59(40): 7939-7947.
[29] Tanaka T, Matsuo Y, Kouno I.A novel black tea pigment and two new oxidation products of epigallocatechin-3-O-gallate[J]. Journal of Agricultural and Food Chemistry, 2005, 53(19): 7571-7578.
[30] Matsuo Y, Tanaka T, Kouno I.A new mechanism for oxidation of epigallocatechin and production of benzotropolone pigments[J]. Tetrahedron, 2006, 62(20): 4774-4783.
[31] Li Y, Tanaka T, Kouno I.Oxidative coupling of the pyrogallol B-ring with a galloyl group during enzymatic oxidation of epigallocatechin 3-O-gallate[J]. Phytochemistry, 2007, 68(7): 1081-1088.
[32] 薛金金. 儿茶素转化形成聚酯型儿茶素和茶黄素变化规律的初步研究[D]. 北京: 中国农业科学院, 2014.
Xue J J.A preliminary study on the variation of theasinensins and theaflavins transformed from catechins [D]. Beijing: Chinese Academy of Agricultural Sciences, 2014.
[33] 徐斌, 江和源, 张建勇, 等. 不同pH条件下TSs的形成机理及其与TFs的竞争性形成研究[J]. 茶叶科学, 2015, 35(3): 281-289.
Xu B, Jiang H Y, Zhang J Y, et al.Formation mechanism of TSs and competitive formation between tss and TFs under various pH[J]. Journal of Tea Science, 2015, 35(3): 281-289.
[34] 施莉婷, 江和源, 张建勇, 等. EGCG与EC酶促氧化产物及其形成途径分析[J]. 食品科学, 2018, 39(22): 1-7.
Shi L T, Jiang H Y, Zhang J Y, et al.Enzymatic oxidation products of EGCG and EC and their formation routes[J]. Food Science, 2018, 39(22): 1-7.
[35] Takuya S, Makoto M, Yosuke M, et al.Biomimetic one-pot preparation of a black tea polyphenol theasinensin A from epigallocatechin gallate by treatment with copper (Ⅱ) chloride and ascorbic acid[J]. Chemical and Pharmaceutical Bulletin, 2011, 59(9): 1183-1185.
[36] 赵熙, 粟本文, 郑红发, 等. 响应面法优化超声波辅助提取绿茶总黄酮工艺的研究[J]. 茶叶科学, 2010, 30(4): 295-301.
Zhao X, Su B W, Zheng H F, et al.Study of optimization of ultrasound-assisted extraction technology of total flavonoids from green tea by response surface methodology[J]. Journal of Tea Science, 2010, 30(4): 295-301.
[37] Liu Y, Luo L Y, Liao C X, et al.Effects of brewing conditions on the phytochemical composition, sensory qualities and antioxidant activity of green tea infusion: A study using response surface methodology[J]. Food Chemistry, 2018, 269(15): 24-34.
[38] Guo L, Guo J C, Zhu W C, et al.Optimized synchronous extraction process of tea polyphenols and polysaccharides from Huaguoshan Yunwu tea and their antioxidant activities[J]. Food and Bioproducts Processing, 2016, 100: 303-310.