Antimicrobial and phytotoxic activities of secondary metabolites from Haplophyllum tuberculatum and Chrysanthemum coronarium
2020
Abdelgaleil, S.A.M. | Saad, M.M.G. | Ariefta, N.R. | Shiono, Y.
Phytochemical investigation led to the isolation of three alkaloids [skimmianine (1), vulcanine (2) and evoxine (3)] from the aerial parts of Haplophyllum tuberculatum, and two diacetylenic spiroketal enol ethers [spiroketalenolether polyyne (4) and [7-hexa-2,4-diynylidene-1,6-dioxaspiro[4.4]nona-2,8-dien-4-yl] acetate (5)] and a sesquiterpene lactone [8α acetoxy-11β,13dihydrokauniolide (6)] from the aerial parts of Chrysanthemum coronarium. The chemical structures of the isolated compounds were determined by using spectral data of ¹H NMR, ¹³C NMR, as well as by comparison with literature data. Compounds 4, 1 and 5 were the most potent inhibitors against plant pathogenic bacteria Rhizobium radiobacter, Ralstonia solanacerum and Pectobacterium carotovorum ss. carotovorum with minimum inhibitory concentration (MIC) values of 31.3, 62.5 and 31.3 µg/ml, respectively. In antifungal assay, compounds 1 (MIC 62.5 µg/ml), 2 (MIC 62.5 µg/ml) and 5 (MIC 125 µg/ml) caused the highest inhibitory effects against phytopathogenic fungi Verticillium dahliae, Fusarium oxysporum and Alternaria solani, respectively. Moreover, crude extract of H. tuberculatum and 4 were significantly the most potent inhibitors of seed germination, root and shoot growth of Echinochloa crus-galli.
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