Glaucolides and guaianolides from Artemisia afra

In vitro antiplasmodial evaluation of medicinal plants from Zimbabwe

“…Highly oxygenated flavonoids are often mentioned for the genus Artemisia with its more than 350 species (Liu and Mabry, 1981;Yang et al, 1995). 3 was already isolated from this species in earlier investigations (Jakupovic et al, 1988;Nkunya et al, 1992), but compounds 6, 7 and 10-12 could be isolated for the first time from A. afra. Three of them, the methylated derivatives of apigenin 3, 6, and 7, revealed in vitro activity against P. falciparum (IC 50 values: 4.3, 5.5 and 5.5 mg/mL, PoW; 7.0, 12.6 and 8.1 mg/mL, Dd2, respectively).…”

“…Compounds 1, 2, 4, 5, 8, and 13-15 turned out to be sesquiterpene lactones (Fig. 4); for identification their 1 H-NMR and EI-MS spectra were compared with published data (Bohlmann and Zdero, 1978;Bohlmann et al, 1980;Greger et al, 1986;Jakupovic et al, 1988;Jakupovic et al, 1991;Singh et al, 1985). Whereas eudesmaafraglaucolide (15) proved to be inactive (IC 50 values >40 g/mL), the guaianolides 1-desoxy-1a-peroxyrupicolin A-8-O-acetate (1), rupicolin A-8-O-acetate (4) and 1a,4a-dihydroxybishopsolicepolide (13) revealed moderate in vitro antiplasmodial activities.…”

Inhibitors of the LPS-induced NF-?B activation from

“…An analysis of its 1 H and 13 C NMR spectral data (Table 1) suggested that compound 1 is a guaianolide (Ahmed et al, 2002;Bohlmann et al, 1981;Todorova et al, 1998). The 1 H NMR spectrum of 1 exhibited signals for an angeloyl group at d H 6.28 (d, J = 7.2 Hz, H-3 0 ), 2.05 (dd, J = 1.5, 7.2 Hz, H-4 0 ), and 1.94 (s, H-5 0 ) (Jakupovic et al, 1988), exomethylene protons at d H 5.58 (s, H-14a) and 5.05 (s, H-14b), an a-methylene proton signals of c-lactone moiety at d H 6.24 and 5.65 (both d, J = 3.0 Hz, H-13a and H-13b), as well as three methine protons at d H 3.98 (dd, J = 9.6, 11.0 Hz, H-6), d H 3.33 (m, H-7), and d H 5.08 (m, H-8). Identification of the protons attached to specific carbons was achieved by analysis of the HMQC and DEPT spectrum, which revealed 20 carbon signals in the 13 C NMR spectrum for three methyls, four methylenes, six methines, and seven quaternary carbons, including three nonprotonated olefinics and two carbonyls.…”

In vitro inhibition of Plasmodium falciparum early and late stage gametocyte viability by extracts from eight traditionally used South African plant species

“…However, A. annua (Asteraceae), that produces a sesquiterpene lactone, artemisinin, has gametocytocidal properties in vitro Lucantoni et al, 2013). The genus Artemisia is well known for the production of sesquiterpene lactones (Al-khathlan et al, 1992) and A. afra is no exception (Al-khathlan et al, 1992;Jakupovic et al, 1988) but there is no evidence for the presence of artemisinin in the latter specie (Van der Kooy et al, 2008;Liu et al, 2009). To our knowledge none of the sesquiterpene lactones (or any other natural compounds from A. afra)…”