Fuzhuanins A and B: The B‑ring Fission Lactones of Flavan-3-ols from Fuzhuan Brick-Tea

Fuzhuan brick-tea is a special dark tea prepared from the leaves of Camellia sinensis var. sinensis. Its production involves a fungal fermentation stage, which forms the unique flavors and functions by a series of biochemical reactions. Our phytochemical research of the material led to the isolation...

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Veröffentlicht in:Journal of agricultural and food chemistry 2013-07, Vol.61 (28), p.6982-6990
Hauptverfasser: Luo, Zhen-Mei, Du, Hai-Xia, Li, Li-Xiang, An, Mao-Qiang, Zhang, Zheng-Zhu, Wan, Xiao-Chun, Bao, Guan-Hu, Zhang, Liang, Ling, Tie-Jun
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container_end_page 6990
container_issue 28
container_start_page 6982
container_title Journal of agricultural and food chemistry
container_volume 61
creator Luo, Zhen-Mei
Du, Hai-Xia
Li, Li-Xiang
An, Mao-Qiang
Zhang, Zheng-Zhu
Wan, Xiao-Chun
Bao, Guan-Hu
Zhang, Liang
Ling, Tie-Jun
description Fuzhuan brick-tea is a special dark tea prepared from the leaves of Camellia sinensis var. sinensis. Its production involves a fungal fermentation stage, which forms the unique flavors and functions by a series of biochemical reactions. Our phytochemical research of the material led to the isolation of two new B-ring fission lactones of flavan-3-ols, fuzhuanins A (1) and B (2). In addition, three other flavan-3-ol derivatives (3–5), three flavone C-glycosides (6–8), eight flavonoid O-glycosides (10–17), five simple phenolics (19–23), two norisoprenoid glycosides (24, 25), two sesquiterpenoids (26, 27), and theobromine (28), as well as two flavonoid anions (9 and 18), were also identified. The structures of these compounds were determined by spectroscopic methods. Compounds 4, 19, 20, 22–24, 26, and 27 were reported for the first time in Camellia spp. and tea. Furthermore, HPLC analysis method was performed to compare the chemical constituents of the before/after fungal fermentation Fuzhuan brick-teas. Compound 1 was indicated as one of the major characteristic constituents generated in the fungal fermentation process. The IC50 value of the antiproliferative activity of 2 on HeLa cells was assayed as 4.48 μM. None of the isolated compounds showed any inhibition activity against the enteric pathogenic microbes at 800 μg/mL by the hole plate diffusion method.
doi_str_mv 10.1021/jf401724w
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Compound 1 was indicated as one of the major characteristic constituents generated in the fungal fermentation process. The IC50 value of the antiproliferative activity of 2 on HeLa cells was assayed as 4.48 μM. None of the isolated compounds showed any inhibition activity against the enteric pathogenic microbes at 800 μg/mL by the hole plate diffusion method.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf401724w</identifier><identifier>PMID: 23837839</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Agronomy. 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Agric. Food Chem</addtitle><description>Fuzhuan brick-tea is a special dark tea prepared from the leaves of Camellia sinensis var. sinensis. Its production involves a fungal fermentation stage, which forms the unique flavors and functions by a series of biochemical reactions. Our phytochemical research of the material led to the isolation of two new B-ring fission lactones of flavan-3-ols, fuzhuanins A (1) and B (2). In addition, three other flavan-3-ol derivatives (3–5), three flavone C-glycosides (6–8), eight flavonoid O-glycosides (10–17), five simple phenolics (19–23), two norisoprenoid glycosides (24, 25), two sesquiterpenoids (26, 27), and theobromine (28), as well as two flavonoid anions (9 and 18), were also identified. The structures of these compounds were determined by spectroscopic methods. Compounds 4, 19, 20, 22–24, 26, and 27 were reported for the first time in Camellia spp. and tea. 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subjects Agronomy. Soil science and plant productions
Anti-Bacterial Agents - pharmacology
Antineoplastic Agents, Phytogenic - pharmacology
Benzopyrans - isolation & purification
Benzopyrans - pharmacology
Biological and medical sciences
Camellia sinensis - chemistry
Cell Proliferation - drug effects
Chromatography, High Pressure Liquid
Coffee, tea and other stimulative beverage industries
Fermentation
Flavonoids - analysis
Food industries
Fundamental and applied biological sciences. Psychology
HeLa Cells
Humans
Lactones - analysis
Lactones - isolation & purification
Lactones - pharmacology
Plant Leaves - chemistry
Tea - chemistry
title Fuzhuanins A and B: The B‑ring Fission Lactones of Flavan-3-ols from Fuzhuan Brick-Tea
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