Mester T, Swarts H J, Romero i Sole S, de Bont J A, Field J A
Department of Food Science, Wageningen Agricultural University, The Netherlands.
Appl Environ Microbiol. 1997 May;63(5):1987-94. doi: 10.1128/aem.63.5.1987-1994.1997.
Aryl metabolites are known to have an important role in the ligninolytic system of white rot fungi. The addition of known precursors and aromatic acids representing lignin degradation products stimulated the production of aryl metabolites (veratryl alcohol, veratraldehyde, p-anisaldehyde, and 3-chloro-p-anisaldehyde) in the white rot fungus Bjerkandera sp. strain BOS55. The presence of manganese (Mn) is known to inhibit the biosynthesis of veratryl alcohol (T. Mester, E. de Jong, and J.A. Field, Appl. Environ. Microbiol. 61:1881-1887, 1995). A new finding of this study was that the production of the other aryl metabolites, p-anisaldehyde and 3-chloro-p-anisaldehyde, was also inhibited by Mn. We attempted to bypass the Mn-inhibited step in the biosynthesis of aryl metabolites by the addition of known and suspected precursors. Most of these compounds were not able to bypass the inhibiting effect of Mn. Only the fully methylated precursors (veratrate, p-anisate, and 3-chloro-p-anisate) provided similar concentrations of aryl metabolites in the presence and absence of Mn, indicating that Mn does not influence the reduction of the benzylic acid group. The addition of deuterated benzoate and 4-hydroxybenzoate resulted in the formation of deuterated aryl metabolites, indicating that these aromatic acids entered into the biosynthetic pathway and were common intermediates to all aryl metabolites. Only deuterated chlorinated anisyl metabolites were produced when the cultures were supplemented with deuterated 3-chloro-4-hydroxybenzoate. This observation combined with the fact that 3-chloro-4-hydroxybenzoate is a natural product of Bjerkandera spp. (H. J. Swarts, F. J. M. Verhagen, J. A. Field, and J. B. P. A. Wijnberg, Phytochemistry 42:1699-1701, 1996) suggest that it is a possible intermediate in chlorinated anisyl metabolite biosynthesis.
已知芳基代谢产物在白腐真菌的木质素降解系统中发挥重要作用。添加代表木质素降解产物的已知前体和芳香酸可刺激白腐真菌Bjerkandera sp.菌株BOS55中芳基代谢产物(藜芦醇、藜芦醛、对甲氧基苯甲醛和3-氯-对甲氧基苯甲醛)的产生。已知锰(Mn)的存在会抑制藜芦醇的生物合成(T. Mester、E. de Jong和J.A. Field,《应用与环境微生物学》61:1881 - 1887,1995年)。本研究的一个新发现是,其他芳基代谢产物对甲氧基苯甲醛和3-氯-对甲氧基苯甲醛的产生也受到锰的抑制。我们试图通过添加已知和可疑的前体来绕过芳基代谢产物生物合成中受锰抑制的步骤。这些化合物大多无法绕过锰的抑制作用。只有完全甲基化的前体(藜芦酸、对甲氧基苯甲酸和3-氯-对甲氧基苯甲酸)在有锰和无锰的情况下提供了相似浓度的芳基代谢产物,这表明锰不影响苄基酸基团的还原。添加氘代苯甲酸和4-羟基苯甲酸导致形成氘代芳基代谢产物,表明这些芳香酸进入了生物合成途径,并且是所有芳基代谢产物的共同中间体。当培养物补充氘代3-氯-4-羟基苯甲酸时,仅产生了氘代氯化茴香基代谢产物。这一观察结果与3-氯-4-羟基苯甲酸是Bjerkandera spp.的天然产物这一事实(H. J. Swarts、F. J. M. Verhagen、J. A. Field和J. B. P. A. Wijnberg,《植物化学》42:1699 - 1701,1996年)相结合,表明它可能是氯化茴香基代谢产物生物合成中的中间体。