Sesquiterpenes and Flavonoid Aglycones from a Hungarian Taxon of the Achillea millefolium Group

Abstract

The investigation of a dichloromethane extract of flower heads of a Hungarian taxon of the Achillea millefolium group led to the isolation of three flavonoid aglycones, one triterpene, one germacranolide and five guaianolides. Their structures were elucidated by UV-VIS, EI- and CI-MS, 1H NMR and 13C NMR spectroscopic methods as well as by 2D-NMR studies and by selective 1D-NOE experiments. Besides apigenin, luteolin and centaureidin, β-sitosterol, 3β-hydroxy-11α,13-dihydro-costunolide, desacetylmatricarin, leucodin, achillin, 8α-angeloxy-leucodin and 8α-angeloxy-achillin were isolated. Both latter substances are reported here for the first time. Their NMR data were compared with those of the other guaianolides. The stereochemistry of 3β-hydroxy-11α,13-dihydro-costunolide was discussed and compared with data of the literature.

Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines

“…Centaureidin (1), casticin (2), artemetin (3) (Atta-urRahman et al., 1988;Barberá et al, 1986;Glasl et al, 2002;Markham and Geiger, 1994;Long et al, 2003), desacetylmatricarin (7) (Glasl et al, 2002) and sintenin (8) (Hatam et al, 1992) were identified on the basis of their spectroscopic data.…”

Évaluation de l'activité antivirale de cinq espèces végétales de la forêt boréale contre les virus influenza de type A et l'herpès simplex de type 1 /

“…On the other hand, some compounds previously isolated from these plants could explain the antiviral activity. Flavonoids and terpenes are the major groups of compounds isolated from A. millefolium Glasl et al, 2002;. Some flavonoids are known for their antiviral activity against HSV-1 ( Khan et al, 2005).…”

Composition of hexane extract of Artemisia lagocephala

“…Air-dried aerial part of A. lagocephala was extracted with hexane at room temperature. The extract was evaporated under vacuum and chromatographed (2u) over a column of silica gel using hexane:EtOAc (100:1, 50:1, 10:1, 2:1) to afford 3E-acetoxycycloartan-24-ozonide (1) [8] (7.2% of the mass of dry extract), 3E-acetoxycycloartan-24-al (2) [8] (6.2%), 25,26,27-trisnor-3E-acetoxycycloartan-24-ol (3) [8] (0.015%), 24,25,26,27-tetranor-3E-acetoxycycloartan-24-ol (4) [8] (0.01%), the sesquiterpene lactone achillin (5) [9] (8.3%), caryophyllene oxide (6) [10] (1.5%), (1R,4S)-p-menth-2-en-1-ol (7) [11] (0.2%), in addition to difficultly separated mixtures of unbranched paraffins (38% of the dry extract), ' 4 -3-ketosteroids (8-11) [12] (0.3%), and ' 5 -sterols [13] (0.2%).Pure compounds were identified based on PMR, 13 C NMR, and 2D spectra and a comparison of them with the literature [8][9][10][11]. Fractions of paraffins, ketosteroids, and sterols were studied using PMR and GC-MS and comparisons with authentic samples and the literature [12,13].…”

“…Pure compounds were identified based on PMR, 13 C NMR, and 2D spectra and a comparison of them with the literature [8][9][10][11]. Fractions of paraffins, ketosteroids, and sterols were studied using PMR and GC-MS and comparisons with authentic samples and the literature [12,13].…”