Abstract
To find good antifungal substances by the bioactivity-guided isolation method, we tracked down the effective antifungal substances in the bark and leaves of Zanthoxylum avicennae, and isolated three antifungal compounds 1, 2, and 3. The structures were identified as xanthyletin, luvangetin, and avicennin by 1H-NMR, 13C-NMR, and HRMS spectra. Particularly, compound 2 had several isomers, and the 1H-NMR spectra of 2 in different solvents showed a significant difference. To determine the stereo structure of 2, a single crystal was prepared and identified by X-ray diffraction as Luvangetin. Moreover, the difference of 1H-NMR data of 2 between in solvent dimethyl sulfoxide-d6 (DMSO-d6) and deuterated chloroform (CDCl3), and other reported isomers were discussed for the first time. The bioassay results indicated that the three compounds 1, 2, and 3 displayed low to high antifungal activities against tested phytopathogenic fungi. In particular, all compounds 1, 2, and 3 showed excellent antifungal activities against Pyricularia oryzae and Z. avicennae, with the values of half maximal effective concentration (EC50) ranging from 31 to 61 mg/L, and compound 3 was also identified as a more potent inhibitor against Fusaium graminearum (EC50 = 43.26 ± 1.76 mg/L) compared with fungicide PCA (phenazine-1-carboxylic acid) (EC50 = 52.34 ± 1.53 mg/L). The results revealed that compounds 1, 2, and 3 were the main antifungal substances of Z. avicennae, and can be used as lead compounds of a fungicide, which has good development value and prospect.
Highlights
Zanthoxylum avicennae belongs to Rutaceae, and is mainly distributed around southern coastal area of China and parts of Southeast Asia, such as Hainan, Fujian, Guangxi, the Philippines, and Vietnam [1]
Fractions A, B, and C were separated and purified by silica gel (200–300 mesh) column chromatography again, and gained three purified compounds 1, 2, and 3, which were identified as xanthyletin, luvangetin, and avicennin by 1 H-NMR, 13 C-NMR, and HRMS spectra
The results showed that the antifungal activities of xanthyletin (1) and lcuvangetin (2) against P. oryae were slightly lower than PCA (29.30 ± 1.89 mg/L), with EC50 values of 31.56 ± 1.86 and 35.89 ± 1.64 mg/L, respectively
Summary
Zanthoxylum avicennae belongs to Rutaceae, and is mainly distributed around southern coastal area of China and parts of Southeast Asia, such as Hainan, Fujian, Guangxi, the Philippines, and Vietnam [1]. Z. avicennae has often been used to treat and relieve many illnesses, such as multi-phlegm, rheumatism, sore throat, jaundice, insect and snake bites, vomiting and diarrhea, repel Ascaris, and digestive system diseases in clinical and in traditional Chinese medicine [2,3,4,5,6,7,8]. Compounds triterpenes, steroids, alkaloids, amides, coumarins, flavonoids, volatile oils, Z. avicennae deserves great research value and the bioactive substances from Z. avicennae and fatty acids [6,9,10,11,12], and many compounds have been proven to have various bioactivities, such have attracted researchers’ attention. Further studies have shown that Z. avicennae mainly contains as anti-cancer, antibacterial [13], antimildew activities [14], inhibitory activities against. Oils, and fatty acids [6,9,10,11,12], and many compounds have been proven to have various bioactivities, such asZ.anti-cancer, antibacterial [13], antimildew activities [14], inhibitory activities against
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