PHENOLS, ACETYLENES, AND SESQUITERPENE LACTONES FROM INULANTHERA-NUDA

Five new compounds, the sesquiterpene lactones 1 and 2, the 2H-pyran-2 -one 9, the flavone glycoside 10, and the organic diacid 11 were isola ted from the CH2Cl2 extract (1 and 2) and from the BuOH parr of the Me OH extract (9-11) of the aerial parts of Inulanthera nuda KALLERSJO (A steraceae). The structures were established by spectroscopic methods, including UV, IR, EI-MS, D/CI-MS and TSP-MS, H-1- and C-13-NMR as well as two-dimensional NMR techniques. The sesquiterpene lactones were id entified as 1 alpha,4 beta,10 beta-trihydroxyguaia-2,11(13)-dieno-12,6 alpha-lactone (1) and 4 beta,10 beta-dihydroxy-1 alpha-methoxyguaia-2 ,11(13)-dieno-12,6 alpha-lactone (2), while 9 was found to be beta-D-g lucopyranosyloxy)-6-methyl-2H-pyran-2-one, 10 was determined as luteol in 7-(2 ''-O-acetyl-beta-D-glucuronoside) and 11 as (Z)-2-(4-hydroxybe nzyl)butenedioic acid. The new compounds were accompanied by six more compounds (3-8) from the CH2Cl2 extract and ten compounds from the BuO H extract (including 12-16). Compounds 3 and 4 were identified as (E)- and (Z)-O-acetyldendranthemenol, while the structures of 5-8 were elu cidated as the flavones salvigenin, 5-hydroxy-3',4',6,7-tetramethoxyfl avone, eupatorin, and cirsilineol, respectively, from their spectrosco pic data (EI- and D/CI-MS, UV, 1H- and C-13-NMR). Compounds 12-16 were determined as scopolin, maltol 3-glucoside, and the flavone glycoside s luteolin 7-glucuronide, apigenin 7-glucuronide, and scutellarein 7-g lucuronide based on spectral evidences (DI CI- and TSP-MS, UV,H-1- and C-13-NMR). The additional five compounds from the BuOH extract were i dentified on-line by HPLC-MS as chlorogenic acid, 3,4-dicaffeoylisoqui nic acid, 1,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, and 3, 4-dicaffeoylisoquinic acid. The identification was based on comparison of retention times and Wand mass spectra with authentic samples.