Abstract
In order to elucidate the metabolism of chlorogenic acid by environmental microbes, a strain of Sphingomonas sp. isolated from tobacco leaves was cultured under various conditions, and chlorogenic acid degradation and its metabolites were investigated. The strain converting chlorogenic acid was newly isolated and identified as a Sphingomonas sp. strain by 16S rRNA sequencing. The optimal conditions for growth and chlorogenic acid degradation were 37 °C and pH 7.0 with supplementation of 1.5 g/l (NH4)2SO4 as the nitrogen source and 2 g/l chlorogenic acid as the sole carbon source. The maximum chlorogenic acid tolerating capability for the strain was 5 g/l. The main metabolites were identified as caffeic acid, shikimic acid, and 3,4-dihydroxybenzoic acid based on gas chromatography-mass spectrometry analysis. The analysis reveals the biotransformation mechanism of chlorogenic acid in microbial cells isolated from the environment.
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References
Whiting, G. C., & Carr, J. G. (1957). Chlorogenic acid metabolism in cider fermentation. Nature, 180, 1479–1479.
Plumb, G. W., Garcia-Conesa, M. T., Kroon, P. A., Rhodes, M., Ridley, S., & Williamson, G. (1999). Metabolism of chlorogenic acid by human plasma, liver, intestine and gut microflora. Journal of the Science of Food and Agriculture, 79, 390–392.
Morton, L. W., Caccetta, R. A.-A., Puddey, I. B., & Croft, K. D. (2000). Chemistry and biological effects of dietary phenolic compounds: relevance to cardiovascular disease. Clinical and Experimental Pharmacol and Physiology, 27, 152–159.
Chu, Y.-F., Chen, Y., Black, R. M., Brown, P. H., Lyle, B. J., Liu, R. H., & Ou, B. (2011). Type 2 diabetes-related bioactivities of coffee: assessment of antioxidant activity, NF-κB inhibition, and stimulation of glucose uptake. Food Chemistry, 124, 914–920.
Pietraforte, D., Castelli, M., Metere, A., Scorza, G., Samoggia, P., Menditto, A., & Minetti, M. (2006). Salivary uric acid at the acidic pH of the stomach is the principal defense against nitrite-derived reactive species: sparing effects of chlorogenic acid and serum albumin. Free Radical Biology and Medicine, 41, 1753–1763.
Van Dam, R. M., & Hu, F. B. (2005). Coffee consumption and risk of type 2 diabetes: a systematic review. JAMA, 294, 97–104.
Huang, M.-T., Smart, R. C., Wong, C.-Q., & Conney, A. H. (1988). Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate. Cancer Research, 48, 5941–5946.
Feng, R., Lu, Y., Bowman, L. L., Qian, Y., Castranova, V., & Ding, M. (2005). Inhibition of activator protein-1, NF-κB, and MAPKs and induction of phase 2 detoxifying enzyme activity by chlorogenic acid. Journal of Biological Chemistry, 280, 27888–27895.
Kasai, H., Fukada, S., Yamaizumi, Z., Sugie, S., & Mori, H. (2000). Action of chlorogenic acid in vegetables and fruits as an inhibitor of 8-hydroxydeoxyguanosine formation in vitro and in a rat carcinogenesis model. Food and Chemical Toxicology, 38, 467–471.
Chlopčíková, Š., Psotová, J., Miketová, P., Soušek, J., Lichnovský, V., & Šimánek, V. (2004). Chemoprotective effect of plant phenolics against anthracycline-induced toxicity on rat cardiomyocytes part II. caffeic, chlorogenic and rosmarinic acids. Phytotherapy Research, 18, 408–413.
Bravo, L. (1998). Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutrition Reviews, 56, 317–333.
Azuma, K., Ippoushi, K., Nakayama, M., Ito, H., Higashio, H., & Terao, J. (2000). Absorption of chlorogenic acid and caffeic acid in rats after oral administration. Journal of Agricultural and Food Chemistry, 48, 5496–5500.
Olthof, M. R., Hollman, P. C. H., Buijsman, M. N. C. P., Van Amelsvoort, J. M. M., & Katan, M. B. (2003). Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. The Journal of Nutrition, 133, 1806–1814.
Gonthier, M. P., Remesy, C., Scalbert, A., Cheynier, V., Souquet, J. M., Poutanen, K., & Aura, A. M. (2006). Microbial metabolism of caffeic acid and its esters chlorogenic and caftaric acids by human faecal microbiota in vitro. Biomedicine and Pharmacotherapy, 60, 536–540.
Farrell, T. L., Dew, T. P., Poquet, L., Hanson, P., & Williamson, G. (2011). Absorption and metabolism of chlorogenic acids in cultured gastric epithelial monolayers. Drug Metabolism and Disposition, 39, 2338–2346.
Couteau, D., Mccartney, A. L., Gibson, G. R., Williamson, G., & Faulds, C. B. (2001). Isolation and characterization of human colonic bacteria able to hydrolyse chlorogenic acid. Journal of Applied Microbiology, 90, 873–881.
Peppercorn, M. A., & Goldman, P. (1971). Caffeic acid metabolism by bacteria of the human gastrointestinal tract. Journal of Bacteriology, 108, 996–1000.
Tomas-Barberan, F., García-Villalba, R., Quartieri, A., Raimondi, S., Amaretti, A., Leonardi, A., & Rossi, M. (2014). In vitro transformation of chlorogenic acid by human gut microbiota. Molecular Nutrition & Food Research, 58, 1122–1131.
Parkar, S. G., Trower, T. M., & Stevenson, D. E. (2013). Fecal microbial metabolism of polyphenols and its effects on human gut microbiota. Anaerobe, 23, 12–19.
Raimondi, S., Anighoro, A., Quartieri, A., Amaretti, A., Tomás-Barberán, F. A., Rastelli, G., & Rossi, M. (2015). Role of bifidobacteria in the hydrolysis of chlorogenic acid. MicrobiologyOpen, 4, 41–52.
Stolz, A. (2008). Molecular characteristics of xenobiotic-degrading sphingomonads. Applied Microbiology and Biotechnology, 81, 793–811.
White, D. C., Sutton, S. D., & Ringelberg, D. B. (1996). The genus Sphingomonas: physiology and ecology. Current Opinion in Biotechnology, 7, 301–306.
Lou, Z., Wang, H., Zhu, S., Ma, C., & Wang, Z. (2011). Antibacterial activity and mechanism of action of chlorogenic acid. Journal of Food Science, 76, M398–M403.
Karunanidhi, A., Thomas, R., Van Belkum, A., & Neela, V. (2013). In vitro antibacterial and antibiofilm activities of chlorogenic acid against clinical isolates of Stenotrophomonas maltophilia including the trimethoprim/sulfamethoxazole resistant strain. BioMed Research International, 2013, 7.
Gauthier, L., Bonnin-Verdal, M.-N., Marchegay, G., Pinson-Gadais, L., Ducos, C., Richard-Forget, F., & Atanasova-Penichon, V. (2016). Fungal biotransformation of chlorogenic and caffeic acids by Fusarium graminearum: new insights in the contribution of phenolic acids to resistance to deoxynivalenol accumulation in cereals. International Journal of Food Microbiology, 221, 61–68.
Ludwig, I. A., Paz De Peña, M., Concepción, C., & Alan, C. (2013). Catabolism of coffee chlorogenic acids by human colonic microbiota. BioFactors, 39, 623–632.
Sánchez‐Maldonado, A., Schieber, A., & Gänzle, M. (2011). Structure–function relationships of the antibacterial activity of phenolic acids and their metabolism by lactic acid bacteria. Journal of Applied Microbiology, 111, 1176–1184.
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This work was supported in part by grants from the Chinese National Science Foundation for Excellent Young Scholars (31422004), the Chinese National Natural Science Foundation (31270154).
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Yuping Ma and Xiaoyu Wang contributed equally to this work.
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Ma, Y., Wang, X., Nie, X. et al. Microbial Degradation of Chlorogenic Acid by a Sphingomonas sp. Strain. Appl Biochem Biotechnol 179, 1381–1392 (2016). https://doi.org/10.1007/s12010-016-2071-2
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DOI: https://doi.org/10.1007/s12010-016-2071-2