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 isolated from the CH2Cl2 extract (1 and 2) and from the BuOH parr of the MeOH extract (9-11) of the aerial parts of Inulanthera nuda KALLERSJO (Asteraceae). 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 identified 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 4-(beta-D-glucopyranosyloxy)-6-methyl-2H-pyran-2-one, 10 was determined as luteolin 7-(2 "-O-acetyl-beta-D-glucuronoside) and 11 as (Z)-2-(4-hydroxybenzyl)butenedioic acid. The new compounds were accompanied by six more compounds (3-8) from the CH2Cl2 extract and ten compounds from the BuOH extract (including 12-16). Compounds 3 and 4 were identified as (E)- and (Z)-O-acetyldendranthemenol, while the structures of 5-8 were elucidated as the flavones salvigenin, 5-hydroxy-3',4',6,7-tetramethoxyflavone, eupatorin, and cirsilineol, respectively, from their spectroscopic 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 glycosides luteolin 7-glucuronide, apigenin 7-glucuronide, and scutellarein 7-glucuronide 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 identified on-line by HPLC-MS as chlorogenic acid, 3,4-dicaffeoylisoquinic 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.
Plants, flavonoids, constituents, athanasia, genera
Publication DOI: 10.1002/(SICI)1522-2675(19981111)81:11<2062::AID-HLCA2062>3.0.CO;2-8Journal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Institutions: Institut de Pharmacognosie et Phytochimie, Universite de Lausanne, Lausanne, Institut de Chimie, Université de Neuchâtel, Neuchâtel, National Herbarium and National Botanic Garden, Harare, Zimbabwe
Methods: 13C NMR, 1H NMR, gel filtration, TLC, UV, extraction, ROESY, hydrolysis, CC, HPLC-MS, centrifugal partition chromatography, MPLC, TSP-MS
Found