Abstract
The phytochemical investigation of Fraxinus hupehensis led to the isolation and characterization of ten compounds which were identified as fraxin (1), fraxetin (2), esculetin (3), cichoriin (4), euphorbetin (5), kaempferol-3-O-β-rutinoside (6), oleuropein (7), linoleic acid (8), methyl linoleate (9), and β-sitosterol (10). Structures of the isolated constituents were characterized by 1H NMR, 13C NMR and HRMS. All the compounds, except compounds 3 and 4, were isolated for the first time from this plant. Further, this was the first report for the occurrence of compound 5 in the Fraxinus species. Antifungal activity evaluation showed that compound 2 exhibited significant inhibitory effects against Bipolaris maydis, Sclerotium rolfsii, and Alternaria solani with EC50 values of 0.31 ± 0.01 mmol/L, 10.50 ± 0.02 mmol/L, and 0.40 ± 0.02 mmol/L respectively, compared to the positive control, Carbendazim, with its EC50 values of 0.74 ± 0.01 mmol/L, 1.78 ± 0.01 mmol/L and 1.41 ± 0.00 mmol/L. Herbicidal activity tests showed that compounds 8–10 had strong inhibitory effects against the roots of Echinochloa crus-galli with EC50 values of 1.16 ± 0.23 mmol/L, 1.28 ± 0.58 mmol/L and 1.33 ± 0.35 mmol/L respectively, more potently active than that of the positive control, Cyanazine, with its EC50 values of 1.56 ± 0.44 mmol/L. However, none of the compounds proved to be active against the tested bacteria (Erwinia carotovora, Pseudomonas syringae, and Ralstonia solanacearum).
Highlights
The genus Fraxinus includes more than 60 species in the world and 30 native species in China, many of which commonly used in Traditional Chinese Medicines
Compounds 2, 3, and 4 have moderate inhibitory effects against all tested fungi, and compound 2 was the best, with the inhibitory effect of against Sclerotium rolfsii reaching 30.34 ± 8.43%, which was higher than positive control, Carbendazim, a broad-spectrum fungicide, whose inhibitory rate was
Comparing the bioassay results of compounds 1–5 belonging to the same skeleton of coumarin [27], the occurence of hydroxyl at C-8 could enhance the activity against Sclerotium rolfsii and the structure-activity relationship of these coumarin derivatives need be further studied later
Summary
The genus Fraxinus includes more than 60 species in the world and 30 native species in China, many of which commonly used in Traditional Chinese Medicines. F. hupehensis, a member of Oleaceae family, is only distributed in Zhongxiang and Jingshan counties, Hubei province of China [1]. It grows slowly, lives long and often forms spines in pairs on their branches. Due to its beautiful tree shape and twisted roots, it is considered to be an ideal bonsai and landscape greening plant which has been called Living fossil or King of bonsai [2] In folk applications, it is very popular because of its delicate appearance and its lack of pests [3]. In traditional Chinese medicine, some species of the genus Fraxinus have been used and the barks of them called Cortex Fraxini [5], commonly known as ‘Qin-Pi’ in Chinese. Based on the above information, it is necessary to systematically study its phytochemistry and examine its fungicidal, herbicidal and bactericidal activities
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