化学
木脂素
内生真菌在植物防御中的应用
酪醇
松脂醇
亚硝酸盐
立体化学
青霉属
食品科学
有机化学
植物
生物
酚类
硝酸盐
作者
Pragya Paramita Pal,Sajeli Ahil Begum,Ameer Basha S,Hiroshi Araya,Yoshinori Fujimoto
标识
DOI:10.1002/cbdv.202200840
摘要
Abstract Inhibiting nitric oxide (NO) or its production is found to be of therapeutic benefit. To discover natural small molecule inhibitors of NO production, a bioassay‐ and LC/MS‐guided chemical investigation was done on the metabolites of endophytic fungus isolated from fresh Piper nigrum fruits. The isolated pure strain was identified as Penicillium polonicum by 16S rDNA sequence comparison. The culture broth extract of P. polonicum (EEPP) exhibited a significant reduction of NO production (Griess method) in LPS‐stimulated RAW 264.7 cells ( P <0.0001). To understand the chemical constituents of bioactive EEPP, column chromatography and p‐TLC studies were carried out, which yielded eight pure compounds. They were characterised as botryosphaeridione ( 1 ), 3‐(3,5‐di‐ tert ‐butyl‐4‐hydroxy)phenylpropionic acid ( 2 ), variabilone ( 3 ), 2,4‐di‐ tert ‐butylphenol ( 4 ), indole‐3‐carboxylic acid ( 5 ), tyrosol ( 6 ), ethyl ferulate ( 7 ) and a new lignan ( 8 ) based on the spectral analysis. The structure elucidation of the new lignan, named polonilignan ( 8 ), was based on HR‐MS, 1 H‐ & 13 C‐NMR, H−H COSY, HSQC and HMBC spectra. Compounds 2 , 4 , 5 and 6 showed a significant decrease ( P <0.0001) in the production of NO in LPS‐induced RAW 264.7 cells. Tyrosol ( 6 ) and indole‐3‐carboxylic acid ( 5 ) controlled nitrite release with IC 50 values of 22.84 and 55.01 μM, respectively. This is the first report of (i) P. polonicum as an endophytic fungus of pepper fruits, (ii) isolation of compounds 1 – 8 except 6 from P. polonicum culture broth extract and (iii) NO inhibition effect of 2 , 4 , 5 and 6 .
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