Comparison of the Antimicrobial and Cytotoxic Activities of Twenty Unsaturated Sesquiterpene Dialdehydes from Plants and Mushrooms

Abstract

Twenty unsaturated sesquiterpene dialdehydes were tested for antimicrobial, algaecidal, cytotoxic, and mutagenic activity. In addition to the known antifungal activity, polygodial (1) also exhibited antibacterial and cytotoxic activity; epipolygodial (2) was slightly less active. The most active compounds were: isovelleral (7), isoisovelleral (8), velleral (20), and methylmarasmate (6). With the exception of velleral (20), they also exhibited mutagenic activity in the Salmonella/microsome assay. Derivatization to less polar compounds usually increased the antimicrobial and cytotoxic effects and reduced mutagenicity, while the introduction of hydroxyl groups had the reverse effect.

Anti-Helicobactor pylori activity of some Jordanian medicinal plants

“…Sesquiterpenes were shown to possess antimicrobial activity against Gram positive bacteria such as Bacillus subtilis, Escherichia coli and S. aureus (Aljancic et al, 1999;Anke & Sterner, 1991;Fortuna et al, 2011;Lin et al, 2003). Additionally, sesquiterpenes lactones were reported to posses anti H. pylori activity (Konstantinopoulou et al, 2003).…”

Regioselective oxidative fragmentation of drimanic terpene alcohols: a short, easy and efficient access to natural and synthetic 11-nordrimane terpene derivatives

“…Melting points were determined in a Stuart Scientific Apparatus SMP3, and are uncorrected. Optical rotations were measured in CHCl 3 Preparation of (5S, 10S)-(9αH)-7-drimene-11,12-diol (9). To a magnetically well-stirred solution of polygodial (10, 3.4 g, 14.53 mmol) in methanol (50 ml), sodium borohydride (2.0 g, 53 mmol) was added in small portions and carefully.…”

“…[1][2][3][4][5][6] For that reason, many efforts have been devoted to the syntheses of drimanes, usually starting from abundant, naturally occurring compounds. 7 In marked contrast, there is hardly any natural product with an 11-nordrimane skeleton known to date, being most of them those shown in Figure 1: isonordrimenone (1), obtained in 1973 from several species of tobacco, as for instance, Greek tobacco, Nicotiana tabacum L., 8 isopolygonal (2) and polygonone (3), obtained in 1985 from the leaves of the folk medicinal plant Polygonum hydropiper L., 9 and polygonal (4), also isolated from Polygonum hydropiper L.…”

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“…1 B), a bicyclic sesquiterpene dialdehyde, was first isolated as a pungent principle from the sprout of Polygonum hydropiper L. (Polygonaceae), known as "tade", which is used as a food spice in Japan [7,8]. The biological activity of polygodial has been reported to include antifungal effects [9][10][11][12]. The biological mechanism of action of polygodial involves structural and functional damage to the plasma membrane, which is accompanied by the leakage of intracellular components.…”