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首页> 外文期刊>Journal of natural products >Unexpected Metabolic Versatility in a Combined Fungal Fomannoxin/Vibralactone Biosynthesis
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Unexpected Metabolic Versatility in a Combined Fungal Fomannoxin/Vibralactone Biosynthesis

机译:真菌福曼毒素/ Vibralactone生物合成中的意外代谢多功能性

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The secondary metabolome of an undescribed stereaceous basidiomycete (BY1) was investigated for bioactive compounds. Along with a known fomannoxin derivative and two known vibralactones, we here describe three new compounds of these natural product families, whose structures were elucidated using 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. The new compound vibralactone S (4) shows a 3,6-substituted oxepin-2(7H)-one ring system, which is unprecedented for the vibralactone/fomannoxin class of compounds. Stable isotope labeling established a biosynthetic route that is dissimilar to the two published cascades of oxepinone formation. Another new compound, the antifungal methyl secofomannoxinate (6), features a 2-methylprop-1-enyl ether moiety, which is only rarely observed with natural products. The structure of 6 was confirmed by total synthesis. 13C-labeling experiments revealed that the unusual 2-methylprop-1-enyl ether residue derives from an isoprene unit. The diversity of BY1's combined fomannoxin/vibralactone metabolism is remarkable in that these compound families, although biosynthetically related, usually occur in different organisms.
机译:研究了未描述的立体担子菌(BY1)的次级代谢组中的生物活性化合物。连同已知的fomannoxin衍生物和两个已知的vibralactones,我们在这里描述了这些天然产物家族的三种新化合物,使用一维和二维核磁共振光谱和高分辨率质谱对它们的结构进行了阐明。新的化合物vibralactone S(4)显示3,6-取代的oxepin-2(7H)-一环系统,这对于vibralactone / fomannoxin类化合物而言是空前的。稳定的同位素标记建立了一条生物合成路线,该路线与两个已公开的环氧皮酮形成级联反应不同。另一种新化合物,抗真菌的癸二氧甘露糖苷酸甲酯(6)具有2-甲基丙-1-烯醚部分,在天然产物中很少见到。通过全合成确认了6的结构。 13C标记实验表明,异常的2-甲基丙-1-烯基醚残基来自异戊二烯单元。 BY1结合的福曼毒素/ vibralactone代谢的多样性是显着的,因为尽管这些化合物家族具有生物合成相关性,但它们通常发生在不同的生物体中。

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