In an attempt to explore the biosynthetic potential of endosymbiotic fungi, the secondary metabolite profiles of the endophytic fungus, Anteaglonium sp. FL0768, cultured under a variety of conditions were investigated. In potato dextrose broth (PDB) medium, Anteaglonium sp. FL0768 produced the heptaketides, herbaridine A (1), herbarin (2), 1-hydroxydehydroherbarin (3), scorpinone (4), and the methylated hexaketide 9S,11R-(+)-ascosalitoxin (5). Incorporation of commonly used epigenetic modifiers, 5-azacytidine and suberoylanilide hydroxamic acid, into the PDB culture medium of this fungus had no effect on its secondary metabolite profile. However, the histone acetyl transferase inhibitor, anacardic acid, slightly affected the metabolite profile affording scorpinone (4) as the major metabolite together with 1-hydroxydehydroherbarin (3) and a different methylated hexaketide, ascochitine (6). Intriguingly, incorporaion of Cu2+ into the PDB medium enhanced production of metabolites and drastically affected the biosynthetic pathway resulting in the production of pentaketide dimers, palmarumycin CE4 (7), palmarumycin CP4 (8), and palmarumycin CP1 (9), in addition to ascochitine (6). The structure of the new metabolite 7 was established with the help of spectroscopic data and by MnO2 oxidation to the known pentaketide dimer, palmarumycin CP3 (10). Biosynthetic pathways to some metabolites in Anteaglonium sp. FL0768 are presented and possible effects of AA and Cu2+ on these pathways are discussed.

中文翻译：

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内生真菌 Anteaglonium sp 聚酮化合物生物合成途径的调节。FL0768，由铜(II)和漆树酸组成。

为了探索内共生真菌的生物合成潜力，内生真菌 Anteaglonium sp 的次生代谢产物谱。对FL0768在多种条件下培养进行了研究。在马铃薯葡萄糖肉汤 (PDB) 培养基中，Anteaglonium sp。FL0768 产生七肽、除草素 A (1)、除草素 (2)、1-羟基脱氢除草素 (3)、蝎酮 (4) 和甲基化六酮化合物 9S,11R-(+)-ascosalitoxin (5)。将常用的表观遗传修饰剂 5-氮杂胞苷和辛二酰苯胺异羟肟酸掺入该真菌的 PDB 培养基中对其次级代谢产物谱没有影响。然而，组蛋白乙酰转移酶抑制剂漆树酸轻微影响代谢物谱，使蝎子酮 (4) 作为主要代谢物，与 1-羟基脱氢马酚素 (3) 和不同的甲基化六酮化合物壳甲壳碱 (6) 一起。有趣的是，将 Cu2+ 掺入 PDB 培养基中可增强代谢物的产生，并极大地影响生物合成途径，从而产生五肽二聚体、棕榈霉素 CE4 (7)、棕榈霉素 CP4 (8) 和棕榈霉素 CP1 (9)，以及壳壳碱（6）。借助光谱数据并通过 MnO2 氧化成已知的五肽二聚体棕榈霉素 CP3，建立了新代谢物 7 的结构 (10)。Anteaglonium sp 中某些代谢物的生物合成途径。介绍了 FL0768，并讨论了 AA 和 Cu2+ 对这些途径的可能影响。