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功能化对位取代苯作为内生节菱孢菌中 1,8-桉叶素生产调节剂。

Functionalized para-substituted benzenes as 1,8-cineole production modulators in an endophytic Nodulisporium species.

机构信息

Department of Plant Sciences, Montana State University, and Endophytics LLC, Suite 201, 920 Technology Blvd, Bozeman, MT 59717, USA.

Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.

出版信息

Microbiology (Reading). 2014 Aug;160(Pt 8):1772-1782. doi: 10.1099/mic.0.079756-0. Epub 2014 May 16.

DOI:10.1099/mic.0.079756-0
PMID:24836622
Abstract

A Nodulisporium species (designated Ti-13) was isolated as an endophyte from Cassia fistula. The fungus produces a spectrum of volatile organic compounds (VOCs) that includes ethanol, acetaldehyde and 1,8-cineole as major components. Initial observations of the fungal isolate suggested that reversible attenuation of the organism via removal from the host and successive transfers in pure culture resulted in a 50 % decrease in cineole production unrelated to an overall alteration in fungal growth. A compound (CPM1) was obtained from Betula pendula (silver birch) that increases the production of 1,8-cineole by an attenuated Ti-13 strain to its original level, as measured by a novel bioassay method employing a 1,8-cineole-sensitive fungus (Sclerotinia sclerotiorum). The host plant produces similar compounds possessing this activity. Bioactivity assays with structurally similar compounds such as ferulic acid and gallic acid suggested that the CPM1 does not act as a simple precursor to the biosynthesis of 1,8-cineole. NMR spectroscopy and HPLC-ES-MS indicated that the CPM1 is a para-substituted benzene with alkyl and carboxyl substituents. The VOCs of Ti-13, especially 1,8-cineole, have potential applications in the industrial, fuel and medical fields.

摘要

一种名为 Nodulisporium sp.(命名为 Ti-13)的真菌被分离为葫芦科植物决明的内生真菌。该真菌产生包括乙醇、乙醛和 1,8-桉叶油醇在内的多种挥发性有机化合物(VOCs),其中乙醇、乙醛和 1,8-桉叶油醇为主要成分。对真菌分离株的初步观察表明,通过从宿主中去除并在纯培养中连续转移,可使生物体可逆性衰减,从而导致桉叶油醇产量降低 50%,与真菌生长的整体变化无关。从银桦(Betula pendula)中获得了一种化合物(CPM1),该化合物可使被削弱的 Ti-13 菌株的 1,8-桉叶油醇产量增加到原始水平,如通过使用对 1,8-桉叶油醇敏感的真菌(核盘菌)的新型生物测定方法所测量的那样。宿主植物也产生具有这种活性的类似化合物。用结构类似的化合物(如阿魏酸和没食子酸)进行的生物活性测定表明,CPM1 不作为 1,8-桉叶油醇生物合成的简单前体。NMR 光谱和 HPLC-ES-MS 表明 CPM1 是一种具有烷基和羧基取代基的对位取代苯。Ti-13 的 VOCs,特别是 1,8-桉叶油醇,在工业、燃料和医疗领域具有潜在的应用。

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