Antimicrobial and phytotoxic activities of secondary metabolites from Haplophyllum tuberculatum and Chrysanthemum coronarium

摘要

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 [8 alpha acetoxy-11 beta,13dihydrokauniolide (6)] from the aerial parts of Chrysanthemum coronarium. The chemical structures of the isolated compounds were determined by using spectral data of H-1 NMR, C-13 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 mu g/ml, respectively. In antifungal assay, compounds 1 (MIC 62.5 mu g/ml), 2 (MIC 62.5 mu g/ml) and 5 (MIC 125 mu g/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 cnts-galli. (C) 2019 SAAB. Published by Elsevier B.V. All rights reserved.