Analysis of Tobacco for the Alternaria Toxins, Alternariol and Alternariol Monomethyl Ether

A new method for detection of five alternaria toxins in food matrices based on LC–APCI-MS

“…Alternaria is able to produce several toxic secondary metabolites, called alternaria mycotoxins (ATs), which include alternariol (AOH), alternariol monomethyl ether (AME), altenuene (ALT), tentoxin (TEN), and tenuazonic acid (TeA) (Scott & Kanhere, 2001). Recent studies reported the presence of these toxins in sorghum, sunflower seeds (Combina, Dalcero, Varsavsky, & Chulze, 1999), cereals (Webley, Jackson, Mullins, Hocking, & Pitt, 1997;Patriarca, Azcarate, Terminiello, & Pinto, 2007), tomatoes (Da Motta & Soares 2000;Asam, Liu, Konitzer, & Rychlik 2011), tobacco (Lucas, Pero, Snow, & Harvan, 1971), wine (Asam, Konitzer, Schieberle, & Rychlik, 2009), carrots (Solfrizzo, De Girolamo, Vitti, & Visconti, 2004), apple juices and beverages (Scott et al, 2001), olives (Visconti, Logrieco, & Bottalico, 1986), and beers (Siegel, Feist, Proske, Koch, & Nehls, 2010). From a toxicological point of view, there is strong evidence that AOH and AME could be mutagenic (An et al, 1989, Brugger et al, 2006.…”

Natural occurrence of alternariols in discolored pecans

“…The natural occurrence of the Alternaría compounds AME and AOH has been established in tobacco (Lucas et al, 1971) and in grain sorghum (Seitz et al, 1975). This report of their occurrence in pecans suggests that they could be present in many other seed crops.…”

“…Freeman (1965) reported the isolation of these compounds from A. dauci (Kuhn) Groves and Skolko. Lucas et al (1971) T h i s c o n t e n t i s isolated both compounds from tobacco. Seitz et al (1975) reported the natural occurrence of the toxins in weathered grain sorghum.…”

Isocoumarin Derivatives from the Sponge‐Associated Fungus Peyronellaea glomerata with Antioxidant Activities

“…Thus, the structure of 5 was determined to be a C(12) epimer of citreoisocoumarinol, namely isocitreoisocoumarinol. In addition, the remaining known isocoumarinrelated derivatives were identical to mucorisocoumarin A (8) [13], citreoisocoumarinol (9) [16], mucorisocoumarin B (10) [13], orthosporin (11) [21], diaportinol (12) [19], LL-Z 1640-7 (13) [20], demethylcitreoviranol (14) [22], citreoviranol (15) [22], alternariol (16) [23], alternariol monomethyl ether (17) [23], and alutenusin (18) [24], based on the spectroscopic analyses and comparison of their NMR, MS, and specific rotation data with those reported in literature. Compound 6 was determined to be (+)citreoisocoumarin [16][17] based on the 1D-and 2D-NMR data analyses and the comparable specific rotations of 6 (½a 25 D = +38.6) and that of citreoisocoumarin (½a 25 D = +46.4) in literature [17].…”

“…This is the first report of (10R)configuration of 7 on the basis of the modified Mosher's method. In addition, the remaining known isocoumarinrelated derivatives were identical to mucorisocoumarin A (8) [13], citreoisocoumarinol (9) [16], mucorisocoumarin B (10) [13], orthosporin (11) [21], diaportinol (12) [19], LL-Z 1640-7 (13) [20], demethylcitreoviranol (14) [22], citreoviranol (15) [22], alternariol (16) [23], alternariol monomethyl ether (17) [23], and alutenusin (18) [24], based on the spectroscopic analyses and comparison of their NMR, MS, and specific rotation data with those reported in literature. Mucorisocoumarins A (8) and B (10) were previously isolated as the enantiomeric mixture [14], while the similar specific rotation between 8 (½a 25 D = +4.9) and mucorisocoumarin A and between 10 (½a 25 D = À5.4) and mucorisocoumarin B [13] suggested 8 and 10 were also isolated as the enantiomeric mixture.…”