植物病原黄单胞菌菌黄素化学结构、生物学功能和生物合成机制研究进展
Research Progress of Xanthomonadin Chemical Structure, Biological Function and Biosynthesis Mechanism in Phytopathogen Xanthomonas
DOI: 10.12677/AMB.2018.74019, PDF,    国家自然科学基金支持
作者: 曹雪强, 何亚文：上海交通大学生命科学技术学院，上海；上海交通大学微生物代谢国家重点实验室，上海；上海交通大学教育部代谢与发育科学国际合作联合实验室，上海
关键词: 黄单胞菌；菌黄素；芳香基多烯链；生物合成途径；Xanthomonas； Xanthomonadin； Aryl-Polyene； Biosynthesis Pathway
摘要: 菌黄素是由植物病原黄单胞菌产生的一类附膜溴化芳香基多烯类黄色素，在溴取代、芳香环甲基化及多烯链链长方面存在结构多样性。菌黄素不仅作为黄单胞菌属的分类和诊断标记，还能保护细菌抵抗光氧化伤害，促进细菌在寄主植物表层的附生，在黄单胞菌致病性和环境适应性方面发挥重要作用。黄单胞菌基因组上一段pig基因簇负责菌黄素的生物合成，该基因簇介导了以3-羟基苯甲酸为前体物新型的II型聚酮合酶生物合成途径。本文将系统综述菌黄素结构、生物学功能和生物合成机制的研究进展。
Abstract: Xanthomonadins are yellow, membrane-bound, brominated, aryl-polyene pigments produced by Xanthomonas bacteria. Xanthomonadins from different Xanthomonas spp. differ in bromination and methylation patterns and the polyene chain length. Xanthomonadin have become useful chemotaxonomic and diagnostic markers for Xanthomonas. Moreover, xanthomonadins play an important role in maintaining the ecological fitness of Xanthomonas species by protecting bacterial cells against photooxidative and peroxidative stress. A pig cluster has been isolated to be responsible for xanthomonadin biosynthesis. Function analysis of the pig cluster showed xanthomonadins are biosynthesized via an unusual type II polyketide synthase pathway, which utilize 3-hydroxybenzoic acid as precursor. This review discusses the chemical structure, biological function and biosynthesis mechanism of xanthomonadin.
文章引用：曹雪强, 何亚文. 植物病原黄单胞菌菌黄素化学结构、生物学功能和生物合成机制研究进展[J]. 微生物前沿, 2018, 7(4): 156-164. https://doi.org/10.12677/AMB.2018.74019

参考文献

[1] Narsing Rao, M.P., Xiao, M. and Li, W.-J. (2017) Fungal and Bacterial Pigments: Secondary Metabolites with Wide Applications. Frontiers in Microbiology, 8, 1113. [Google Scholar] [CrossRef] [PubMed]
[2] Tuli, H.S., Chaudhary, P., Beniwal, V., et al. (2015) Microbial Pigments as Natural Color Sources: Current Trends and Future Perspectives. Journal of Food Science and Technology. 52, 4669-4678. [Google Scholar] [CrossRef] [PubMed]
[3] Leyns, F., Marcel De, C., Jean-Guy, S., et al. (1984) The Host Range of the Genus Xanthomonas. Botanical Review, 50, 308-356. [Google Scholar] [CrossRef] 
[4] Buttner, D. and Bonas, U. (2010) Regulation and Secretion of Xanthomonas Virulence Factors. FEMS Microbiology Review, 34, 107-133. [Google Scholar] [CrossRef] [PubMed]
[5] Starr, M.P. and Stephens, W.L. (1964) Pigmentation and Taxonomy of the Genus Xanthomonas. Journal of Bacteriology, 87, 293-302.
[6] Andrewes, A.G., Jenkins, C.L., Starr, M.P., et al. (1976) Structure of Xanthomonadin I, a Novel Dibrominated Aryl-Polyene Pigment Produced by the Bacterium Xanthomonas juglandis. Tetrahedron Letters, 17, 4023-4024. [Google Scholar] [CrossRef] 
[7] Stephens, W.L. and Starr, M.P. (1963) Localization of Carotenoid Pigment in the Cytoplasmic Membrane of Xanthomonas juglandis. Journal of Bacteriology, 86, 1070-1074.
[8] Andrewes, A.G., Hertzberg, S., Liaaen-Jensen, S., et al. (1973) The Xanthomonas “Carotenoids”—Non-Carotenoid Brominated Aryl-Polyene Esters. Acta Chemical Scandinavica, 27, 2383-2395. [Google Scholar] [CrossRef] [PubMed]
[9] Aririatu, L.E. and Kester, A.S. (1985) Isolation and Characterization of the Pigment Esters of Xanthomonas juglandis (Campestris). Microbiology, 131, 2047-2052. [Google Scholar] [CrossRef] 
[10] Dianese, J.C. and Schaad, N.W. (1982) Isolation and Characterization of Inner and Outer Membranes of Xanthomonas campestris pv. Campestris. Phytopathology, 72, 1284-1289. [Google Scholar] [CrossRef] 
[11] Moser, R., Aktas, M. and Narberhaus, F. (2014) Phosphatidylcholine Biosynthesis in Xanthomonas campestris via a Yeast-Like Acylation Pathway. Molecular Microbiology, 91, 736-750. [Google Scholar] [CrossRef] [PubMed]
[12] Cao, X.Q., Wang, J.Y., Zhou, L., et al. (2018) Biosynthesis of the Yellow Xanthomonadin Pigments Involves an ATP-Dependent 3-Hydroxybenzoic acid:acyl Carrier Protein Ligase and an Unusual Type II Polyketide Synthase Pathway. Molecular Microbiology, 110, 16-32. [Google Scholar] [CrossRef] [PubMed]
[13] Jenkins, C.L. and Starr, M.P. (1982) The Brominated aryl-polyene (Xanthomonadin) Pigments of Xanthomonas juglandis Protect against Photobiological Damage. Current Microbiology, 7, 323-326. [Google Scholar] [CrossRef] 
[14] Rajagopal, L., Sundari, C.S., Balasubramanian, D., et al. (1997) The Bacterial Pigment Xanthomonadin Offers Protection against Photodamage. FEBS Letter, 415, 125-128. [Google Scholar] [CrossRef] 
[15] 邹华松, 陈功友, 赖志兵, 等. 水稻黄单胞菌黄色素合成相关基因的克隆与鉴定[J]. 微生物学报, 2003, 43(2): 180-188.
[16] Poplawsky, A.R., Urban, S.C. and Chun, W. (2000) Biological Role of Xanthomonadin Pigments in Xanthomonas campestris pv. campestris. Applied Environmental Microbiology, 66, 5123-5127. [Google Scholar] [CrossRef] 
[17] Wang, Y., Qian, G., Li, Y., et al. (2013) Biosynthetic Mechanism for Sunscreens of the Biocontrol Agent Lysobacter enzymogenes. PLoS ONE, 8, e66633. [Google Scholar] [CrossRef] [PubMed]
[18] He, Y.W., Wu, J., Zhou, L., et al. (2011) Xanthomonas campestris Diffusible Factor Is 3-Hydroxybenzoic Acid and Is Associated with Xanthomonadin Biosynthesis, Cell Viability, Antioxidant Activity, and Systemic Invasion. Molecular Plant-Microbe Interaction, 24, 948-957. [Google Scholar] [CrossRef] 
[19] Goel, A.K., Rajagopal, L. and Sonti, R.V. (2001) Pigment and Virulence Deficiencies Associated with Mutations in the aroE Gene of Xanthomonas oryzae pv. oryzae. Applied Environmental Microbiology, 67, 245-250. [Google Scholar] [CrossRef] 
[20] Poplawsky, A.R., Kawalek, M.D. and Schaad, N.W. (1993) A Xanthomonadin-Encoding Gene Cluster for the Identification of Pathovars of Xanthomonas campestris. Molecular Plant-Microbe Interactions, 6, 545-552. [Google Scholar] [CrossRef] 
[21] Poplawsky, A.R. and Chun, W. (1997) pigB Determines a Diffusible Factor Needed for Extracellular Polysaccharide Slime and Xanthomonadin Production in Xanthomonas campestris pv. campestris. Journal of Bacteriology, 179, 439-444. [Google Scholar] [CrossRef] [PubMed]
[22] Goel, A.K., Rajagopal, L., Nagesh, N., et al. (2002) Genetic Locus Encoding Functions Involved in Biosynthesis and Outer Membrane Localization of Xanthomonadin in Xanthomonas oryzae pv. oryzae. Journal of Bacteriology, 184, 3539-3548. [Google Scholar] [CrossRef] 
[23] Zhou, L., Wang, J.-Y., Wang, J., et al. (2013) The Diffusible Factor Synthase xanB2 Is a Bifunctional Chorismatase That Links the Shikimate Pathway to Ubiquinone and Xanthomonadins Biosynthetic Pathways. Molecular Microbiology, 87, 80-93. [Google Scholar] [CrossRef] [PubMed]
[24] Poplawsky, A.R., Walters, D.M., Rouviere, P.E., et al. (2005) A Gene for a Dioxygenase-Like Protein Determines the Production of the df Signal in Xanthomonas campestris pv. campestris. Molecular Plant Pathology, 6, 653-657. [Google Scholar] [CrossRef] [PubMed]
[25] Chun, W., Cui, J. and Poplawsky, A. (1997) Purification, Characterization and Biological Role of a Pheromone Produced by Xanthomonas campestris pv. campestris. Physiological and Molecular Plant Pathology, 51, 1-14. [Google Scholar] [CrossRef] 
[26] Yajima, A., Imai, N., Poplawsky, A.R., et al. (2010) Synthesis of a Proposed Structure for the Diffusible Extracellular Factor of Xanthomonas campestris pv. campestris. Tetrahedron Letters, 51, 2074-2077. [Google Scholar] [CrossRef] 
[27] Zhou, L., Huang, T.W., Wang, J.Y., et al. (2013) The Rice Bacterial Pathogen Xanthomonas oryzae pv. oryzae Produces 3-Hydroxybenzoic Acid and 4-Hydroxybenzoic Acid via XanB2 for Use in Xanthomonadin, Ubiquinone, and Exopolysaccharide Biosynthesis. Molecular Plant-Microbe Interaction, 26, 1239-1248. [Google Scholar] [CrossRef] 
[28] Schöner, T.A., Fuchs, S.W., Reinhold-Hurek, B., et al. (2014) Identification and Biosynthesis of a Novel Xanthomonadin-Dialkylresorcinol-Hybrid from Azoarcus sp. BH72. PLoS ONE, 9, e90922. [Google Scholar] [CrossRef] [PubMed]
[29] Poplawsky, A.R., Chun, W., Slater, H., et al. (1998) Synthesis of Extracellular Polysaccharide, Extracellular Enzymes, and Xanthomonadin in Xanthomonas campestris: Evidence for the Involvement of Two Intercellular Regulatory Signals. Molecular Plant-Microbe Interactions, 11, 68-70. [Google Scholar] [CrossRef] 
[30] Wang, X.Y., Zhou, L., Yang, J., et al. (2016) The rpfB-Dependent Quorum Sensing Signal Turnover System Is Required for Adaptation and Virulence in Rice Bacterial Blight Pathogen Xanthomonas oryzae pv. oryzae. Molecular Plant-Microbe Interaction, 29, 220-230. [Google Scholar] [CrossRef] 
[31] Zhou, L., Yu, Y., Chen, X., et al. (2015) The Multiple DSF-Family QS Signals Are Synthesized from Carbohydrate and Branched-Chain Amino Acids via the FAS Elongation Cycle. Scientific Reports, 5, Article No. 13294. [Google Scholar] [CrossRef] [PubMed]
[32] Schoner, T.A., Gassel, S., Osawa, A., et al. (2016) Aryl Polyenes, a Highly Abundant Class of Bacterial Natural Products, Are Functionally Related to Antioxidative Carotenoids. ChemBioChem, 17, 247-253. [Google Scholar] [CrossRef] [PubMed]
[33] Achenbach, H., Kohl, W., Wachter, W., et al. (1978) Investigations of the Pigments from Cytophaga johnsonae Cyj1. Archives of Microbiology, 117, 253-257. [Google Scholar] [CrossRef] 
[34] Cimermancic, P., Medema, M.H., Claesen, J., et al. (2014) Insights into Secondary Metabolism from a Global Analysis of Prokaryotic Biosynthetic Gene Clusters. Cell, 158, 412-421. [Google Scholar] [CrossRef] [PubMed]
[35] Wang, J.-Y., Zhou, L., Chen, B., et al. (2015) A Functional 4-Hydroxybenzoate Degradation Pathway in the Phytopathogen Xanthomonas campestris Is Required for Full Pathogenicity. Scientific Reports, 5, Article No. 18456. [Google Scholar] [CrossRef] [PubMed]

为你推荐