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Modulation of the biosynthesis of oxyprenylated coumarins in calli from Ferulago campestris elicited by ferulic acid
Biomass Conversion and Biorefinery ( IF 3.5 ) Pub Date : 2022-09-20 , DOI: 10.1007/s13399-022-03309-z
Serena Fiorito , Lucia Palumbo , Francesco Epifano , Daniele Fraternale , Chiara Collevecchio , Salvatore Genovese

Previous and recent literature acquisitions suggested that cultured calli are an efficient and meaningful model to investigate the extent and fate of prenylation of phenylpropanoid cores in plants belonging to the Rutaceae and Apiaceae families upon administration of putative biosynthetic precursors. To this concern, in the present manuscript, we investigated the effect of supplementation of ferulic acid and umbelliferone on the biosynthesis of their oxyprenylated counterparts in Ferulago campestris (Besser) Grecescu (Fam. Apiaceae) cultured calli. Dried plant biomass material has been extracted by an ultrasound-assisted extraction with EtOH. O-prenyl secondary metabolites, namely 3,3-dimethylallyloxy, geranyloxy, and farnesyloxy derivatives of both ferulic acid and umbelliferone, were identified and quantified by HPLC/DAD analyses. Supplementation with ferulic acid was the only treatment providing appreciable results. Quite surprisingly, its addition to cultured calli did not affect the formation of its oxyprenylated phytochemicals but boosted the biosynthesis of umbelliferone and its farnesyloxy-derivative umbrelliprenin. The findings reported herein enforce and underline the role of ferulic acid as an elicitor of selected classes of secondary metabolites in apiaceous species, as recently observed. In addition to these results, a novel hitherto unknown metabolite from F. campestris, namely 7-[[(2E)-7-hydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-2H-1-benzopyran-2-one, was characterized by NMR and LC–MS analyses.



中文翻译:

阿魏酸对阿魏酸愈伤组织中氧异戊二烯化香豆素生物合成的调控

以前和最近的文献资料表明,培养的愈伤组织是一种有效且有意义的模型,用于研究在施用推定的生物合成前体后属于芸香科和伞形科植物中苯丙素核心的异戊烯化程度和命运。为此,在本手稿中,我们研究了补充阿魏酸和伞形酮对Ferulago campestris (Besser) Grecescu (Fam. Apiaceae) 培养的愈伤组织中氧异戊二烯化对应物的生物合成的影响。干燥的植物生物质材料已通过使用 EtOH 的超声辅助提取来提取。-异戊二烯次级代谢物,即阿魏酸和伞形酮的 3,3-二甲基烯丙氧基、香叶氧基和法呢氧基衍生物,通过 HPLC/DAD 分析进行鉴定和量化。补充阿魏酸是唯一提供显着结果的治疗方法。相当令人惊讶的是,将其添加到培养的愈伤组织中并不会影响其氧异戊二烯化植物化学物质的形成,而是促进了伞形酮及其法呢氧基衍生物伞形普利宁的生物合成。正如最近观察到的,本文报告的研究结果强化并强调了阿魏酸作为蜜蜂科物种中选定类别的次级代谢物的引发剂的作用。除了这些结果,来自F. campestris的一种新的迄今为止未知的代谢物,即 7-[[(2 E)-7-hydroxy-3,7-dimethyl-2-octen-1-yl]oxy]-2 H -1-benzopyran-2-one,通过 NMR 和 LC-MS 分析表征。

更新日期:2022-09-20
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