Terpenoid metabolites from the aerial part of Artemisia lagocephala

A Novel 3,9-(1,2,3-Trioxocine)-Type Steroid of Rauia nodosa (Rutaceae)

“…A few natural ozonides (structures containing the 1,2,3-trioxocine group) as precursors in ozonolysis of olefins, have been discovered in higher plant species [16,17,18]. However, plant ozonides could be formed from cuticle olefins with ozone from the air, or alternatively inside cells, as ozone may enter the mesophyll of the plants [19,20] causing necrosis of the leaves.…”

Natural Products with Heteroatom-Rich Ring Systems

“…Trioxolane 16 failed to exhibit antimalarial activity against Plasmodium falciparum (NF 54) in vitro at 5 μg mL –1 . In 2012, triterpene trioxolane 17 was isolated as a 1:1 mixture of diastereomers from rabbit-head wormwood, Artemisea lagocephala , collected in South Sikhote-Alin, Primorsky Territory, Russia . The mixture of trioxolane diastereomers 17 was found to exhibit moderate antifungal activity against Aspergillus niger , Fusarium oxysporum , and Cercospora sojina with inhibition zones of ∼2 mm at 100 μg/hole …”

Composition of hexane extract of Artemisia lagocephala

“…The aqueous extract of A. lagocephala contained the sesquiterpenoid lactone achillin [7]. The establishment of the structures of new cycloartane derivatives from A. lagocephala was reported [8]. Herein we communicate information on the composition of the hexane extract of A. lagocephala and the biological activity of its components.…”

“…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].…”