Biotransformation of geniposide by Synechocystis sp. PCC 6803 into genipin and its inhibitory effects on BEL-7402, Escherichia coli, and cyanobacteria

详细信息    查看全文

• 作者：Zhi Wang ; Lu Zhang ; Xiao-Dong Cui ; Tai-Sen Hao ; Chun-Mei Wang…
• 关键词：Genipin ; Synechocystis sp. PCC 6803 ; Biotransformation ; Cytotoxicity ; Microcystis sp. PCC 7806
• 刊名：Annals of Microbiology
• 出版年：2015
• 出版时间：September 2015
• 年：2015
• 卷：65
• 期：3
• 页码：1303-1311
• 全文大小：649 KB
• 参考文献：Akao T, Kobashi K, Aburada M (1994) Enzymic studies on the animal and intestinal bacterial metabolism of geniposide. Biol Pharm Bull 17:1573-576. doi:10.-248/?bpb.-7.-573 PubMed View Article
  Alexova R, Fujii M, Birch D, Cheng J, David-Waite T, Ferrari BC, Neilan BA (2011) Iron uptake and toxin synthesis in the bloom-forming Microcystis aeruginosa under iron limitation. Environ Microbiol 13:1064-077. doi:10.-111/?j.-462-2920.-010.-2412.?x PubMed View Article
  Deng Y, Guan M, Xie X, Yang X, Xiang H, Li H, Zou L, Wei J, Wang D, Deng X (2013) Geniposide inhibits airway inflammation and hyperresponsiveness in a mouse model of asthma. Int Immunopharmacol 17:561-67. doi:10.-016/?j.?intimp.-013.-6.-28 PubMed View Article
  Faramarzi MA, Adrangi S, Yazdi MT (2008) Microalagal biotransformation of steroids. J Phycol 44:27-7. doi:10.-111/?j.-529-8817.-007.-0446.?x View Article
  Fu Y, Liu B, Liu J, Liu Z, Liang D, Li F, Li D, Cao Y, Zhang X, Zhang N, Yang Z (2012) Geniposide, from Gardenia jasminoides Ellis, inhibits the inflammatory response in the primary mouse macrophages and mouse models. Int Immunopharmacol 14:792-98. doi:10.-016/?j.?intimp.-012.-7.-06 PubMed View Article
  Ghasemi Y, Rasoul Amini S, Fotooh Abadi E (2011) The biotransformation, biodegradation, and bioremediation of organic compounds by microalgae. J Phycol 47:969-80. doi:10.-111/?j.-529-8817.-011.-1051.?x View Article
  Hsu HY, Yang JJ, Lin SY, Lin CC (1997) Comparisons of geniposidic acid and geniposide on antitumor and radioprotection after sublethal irradiation. Cancer Lett 113:31-7. doi:10.-016/?s0304-3835(96)04572-7 PubMed View Article
  Humbert JF, Barbe V, Latifi A, Gugger M, Calteau A, Coursin T, Lajus A, Castelli V, Oztas S, Samson G, Longin C, Medigue C, Marsac NT (2013) A tribute to disorder in the genome of the bloom-forming freshwater cyanobacterium Microcystis aeruginosa. PLoS One 8:e70747. doi:10.-371/?journal.?pone.-070747 PubMed Central PubMed View Article
  Kang MJ, Khanal T, Kim HG, Lee DH, Yeo HK, Lee YS, Ahn YT, Kim DH, Jeong HG, Jeong TC (2012) Role of metabolism by human intestinal microflora in geniposide-induced toxicity in HepG2 cells. Arch Pharm Res 35:733-38. doi:10.-007/?s12272-012-0418-y PubMed View Article
  Khanal T, Kim HG, Choi JH, Do MT, Kong MJ, Kang MJ, Noh K, Yeod HK, Ahn YT, Kang W, Kim DH, Jeong TC, Jeong HG (2012) Biotransformation of geniposide by human intestinal microflora on cytotoxicity against HepG2 cells. Toxicol Lett 209:246-54. doi:10.-016/?j.?toxlet.-011.-2.-17 PubMed View Article
  Kim BC, Kim HG, Lee SA, Lim S, Park EH, Kim SJ, Lim CJ (2005) Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Biochem Pharmacol 70:1398-407. doi:10.-016/?j.?bcp.-005.-7.-25 PubMed View Article
  Kim CY, Kim J (2007) Preparative isolation and purification of geniposide from gardenia fruits by centrifugal partition chromatography. Phytochem Anal 18:115-17. doi:10.-002/?pca.-58 PubMed View Article
  Kim HW, Vannela R, Rittmann BE (2013) Responses of Synechocystis sp. PCC 6803 to total dissolved solids in long-term continuous operation of a photobioreactor. Bioresour Technol 128:378-84. doi:10.-016/?j.?biortech.-012.-0.-46 PubMed View Article
  Koo HJ, Lim KH, Jung HJ, Park EH (2006) Anti-inflammatory evaluation of gardenia extract, geniposide and genipin. J Ethnopharmacol 103:496-00. doi:10.-016/?j.?jep.-005.-8.-11 PubMed View Article
  Lelono RAA, Tachibana S, Itoh K (2009) Isolation of antifungal compounds from Gardenia jasminoides. Pak J Biol Sci 12:949-56. doi:10.-923/?pjbs.-009.-49.-56 PubMed View Article
  Li Y, Jin W, Jing W, Yao M, Tang Y, Lu F (2014) Enzymolysis and Microbial Transformation of Geniposide in Gardenia Jasminoides into Genipin by Aspergillus niger, p 981-992. In Zhang TC, Ouyang P, Kaplan S, Skarnes B (ed), Proceedings of the 2012 International Conference on Applied Biotechnology (ICAB 2012), Springer Berlin Heidelberg. doi:10.-007/-78-3-642-37922-2_-05
  Liu Y, Chen W, Kim HI (2012) Mechanical and antimicrobial properties of genipin-crosslinked chitosan/poly (ethylene glycol) IPN. J Macromol ScI, Part B, Phys 51:1069-079. doi:10.-080/-0222348.-011.-25889 View Article
  Lu M, Qiao Q, Pang C, Wang Y (2002) Effect of macroporous resin in separation of gardenoside. Zhong Cao Yao. 33:794-795. doi: 10.3321/j.issn:0253-2670.2002.09.014
  Ma T, Huang C, Zong G, Zha D, Meng X, Li J, Tang W (2011) Hepatoprotective effects of geniposide in a rat model of nonalcoholic steatohepatitis. J Pharm Pharmacol 63:587-93. doi:10.-111/?j.-042-7158.-011.-1256.?x PubMed View Article
  Nam KN, Choi YS, Jung HJ, Park GH, Park JM, Moon SK, Cho KH, Kang C, Kang I, Oh MS, Lee EH (2010) Genipin inhibits the inflammatory response of rat brain microglial cells. Int Immunopharmacol 10:493-99. doi:10.-016/?j.
• 作者单位：Zhi Wang (1)
  Lu Zhang (1)
  Xiao-Dong Cui (1)
  Tai-Sen Hao (1)
  Chun-Mei Wang (1)
  Xiang-Xiang Gu (1)
  Yong-Gang Liu (1)
  Jun-Gui Dai (2)
  Agaru Bao (1)
  
  1. Department of Biological Pharmaceutics, School of Materia Medica, Beijing University of Chinese Medicine, Beijing, China, 100102
  2. Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing, China
  
• 刊物主题：Microbiology; Microbial Genetics and Genomics; Microbial Ecology; Fungus Genetics; Medical Microbiology; Applied Microbiology;
• 出版者：Springer Berlin Heidelberg
• ISSN：1869-2044

文摘

Synechocystis sp. PCC 6803, a freshwater cyanobacterium that is widely distributed in nature, was chosen for the transformation of geniposide extracted from the Chinese traditional medicine plant Gardenia jasminoides. After a period of 25?days, two converted products were obtained according to the TLC and HPLC results. NMR was used to identify the products. One was genipin (A), an iridoid compound that possesses various pharmacological effects, and its in vitro anti-tumor and anti-bacterial activity were measured. This compound showed a concentration-dependent and time-dependent inhibitory effect against BEL-7402. The IC50 of genipin after incubation with BEL-7402 for 72?h was 16.0?μg?mL-1. The diameter of the inhibition zone of genipin at a concentration of 10?μg?mL-1 on a culture of Escherichia coli was 24.2?mm. This manuscript provides the first demonstration of the strong in vitro anti-bacterial activity of genipin. Geniposide also showed inhibitory ability on the growth of BEL-7402 and bacterial cells, but its effects were weaker than that of genipin. In addition, the cytotoxicity of genipin against Synechocystis sp. PCC 6803 or another bloom-forming cyanobacterium, Microcystis sp. PCC 7806, was evaluated. Genipin exhibited a high level of cytotoxicity against Synechocystis sp. PCC 6803 and Microcystis sp. PCC 7806 with IC50 values of 1.33?μg?mL-1 and 66.27?μg?mL-1, respectively. In conclusion, the results indicate Synechocystis sp. PCC 6803 as a potential biocatalyst for the transformation of geniposide into genipin, which not only has valuable pharmacological activities (determined in this study and by other research groups), but also shows potential for water-bloom control (based on the results of assays on two cyanobacteria reported herein).