Chemical Constituents Of Phryma Leptostachya L.

To search for the insecticidal constituents of Phryma leptostachya L., the chemical constituents of the whole plant were investigated systematically.The dried material was extacted with95%EtOH by percolation, and the percolate was suspended in H2O and then partitioned by extraction with petroleum ether, AcOEt and n-BuOH, in turn.20compounds were isolated from the ethanol extract of Phryma leptostachya by using various chromatographic and other methods, such as column chromatography with silica gel, polyamide, and sephadex LH-20, semipreparative HPLC, preparative TLC, recrystallisation, et al. The structures of the20compounds were determined to be13lignans,2flavones,2triterpenes, and3other compounds on the basis of analyzing their physicochemical properties and spectroscopic data (HR-MS,1H-NMR,13C-NMR, HSQC, HMBC, NOESY, et al.). Among the13lignans,5were new and were named as haedoxan J, haedoxancoside, Phrymarolin Ⅲ, Phrymarolin IV, and Phrymarolin V, respectively. The other known compounds were haedoxan A,1-(4,6-dimethoxy-1,3-benzodioxol-5-yl)dihydro-4-(6-methoxy-1,3-benzodioxol-5-yl)-1H,3H-furo[3,4-c]furan-3a(4H)-yl acetate, leptostachyol acetate,4-(4,6-dimethoxy-1,3-benzo-dioxol-5-yl)dihydro-1-(4-methoxy-1,3-benzodioxol-5-yl)-1H,3H-furo[3,4-c] furan-3a(4H)-yl acetate,2,6-dimethoxyl-phrymarolin Ⅱ, Leptostachyol Acetate C,4-(4,6-dimethoxy-1,3-benzodioxol-5-yl)dihydro-1-(6-methoxy-1,3-benzodioxol-5-yl)-1H,3H-furo[3,4-c]furan-3a(4H)-yl acetate, phrymarolin Ⅱ, apigenin, quercetin, ursolic acid, oleanolic acid, isovanillic acid,p-hydroxybenzoic acid, and adenine arabinoside, respectively.Besides the5new compounds,9among the20compounds, such as4-(4,6-dimethoxy-1,3-benzo-dioxol-5-yl)dihydro-1-(4-methoxy-1,3-benzodioxol-5-yl)-1H,3H-furo[3,4-c]furan-3a(4H)-yl acetate,2,6-dimethoxyl-phrymarolin Ⅱ,4-(4,6-dimethoxy-1,3-benzodioxol-5-yl)dihydro-1-(6-methoxy-1,3-benzodioxol-5-yl)-1H,3H-furo [3,4-c] furan-3a(4H)-yl acetate, apigenin, quercetin, oleanolic acid, isovanillic acid, p-hydroxybenzoic acid, and adenine arabinoside, were isolated from this plant for the first time. The results of our studies were in accordance with the reports on chemical constituents of Phryma leptostachya which indicated that lignans were the main constituents of the title plant.