Formation of Diketopiperazines by Penicillium italicum Isolated from Oranges

Abstract

Prolyl-2-(1',1'-dimethylallyl)tryptophyldiketopiperazine and 12,13-dehydroprolyl-2-(1',1'-dimethylallyl)tryptophyldiketopiperazine, known metabolites of Aspergillus ustus, were produced in low yield by Penicillium italicum in liquid culture and on unsterilized orange peel.

Penicillium italicum: An Underexplored Postharvest Pathogen

“…Nevertheless, further analysis by did not add P. italicum among mycotoxigenic producers but reported secondary metabolites such as deoxybrevianamide E (1), xanthocyllin (3), and PI-3 (9) (Arai et al, 1989). Other studies developed by Faid and Tantaoui-Elaraki (1989), Scott et al (1974), and Arai et al (1989) and collaborators have also managed to identify some NPs produced by P. italicum (Table 4), such as 5,6-dihydroxy-4-methoxy-2Hpyran-2-one (5), which is classified as a mycotoxin according to the Human Metabolome Database 1 (HMDB) (Faid and Tantaoui-Elaraki, 1989), low amounts of deoxybrevianamide E (1) and dehydrodeoxybrevianamide E (2), common metabolites from Aspergillus ustus (Scott et al, 1974), and 4-methoxy-6-npropenyl-2-pyrone (6) as well as new compounds such as PI-1 (7) PI-2 (8), PI-3 (9), and PI-4 (10) (Arai et al, 1989). Whilst searching for NPs produced by species of Penicillium, listed the NPs already mentioned as well as other NPs, such as arabenoic acid (12), dehydrofulvic acid (11), formylxanthocillin X (4), 5-hydroxymethylfuric acid (13), and other metabolites, which could not be identified.…”

“…In this study, pointed out NPs that could be characterized as mycotoxins (5, 6, and 7), herbicides (1, 12, and 11) and those with potential antibiotic activity (2, 6, and 13). Although these metabolites have been detected in vitro in artificial culture Scott et al, 1974;Arai et al, 1989;Smedsgaard et al, 20042 Dehydrodeoxybrevianamide E Scott et al, 19743 Xanthocyllin X Frisvad et al, 20044 Formylxanthocillin X Frisvad et al, 2004 5 5,6-dihydroxy-4-methoxy-2H-pyran-2-one Faid and Tantaoui-Elaraki, 1989 6 4-methoxy-6-n-propenyl-2-pyrone Arai et al, 1989 7 PI-1 Arai et al, 19898 PI-2 Arai et al, 19899 PI-3 Arai et al, 198910 PI-4 Arai et al, 1989 (Continued) 12 Arabenoic acid 13 5-hydroxymethylfuric acid media, these metabolites have not been linked to infection yet and many other metabolites remain to be identified . In addition, there are no studies concerning the toxicity of these NPs against humans, plants, animals and bacteria (Faid and Tantaoui-Elaraki, 1989).…”

Chemical Synthesis of (+)-Brevianamide a Supports a Diels–Alderase-Free Biosynthesis

“…30 Our new biosynthetic hypothesis for (+)-brevianamide A (1) involves an alternative biosynthetic precursor, (+)-dehydrodeoxybrevianamide E (9), which is a known natural product isolated from various Penicillium and Aspergillus species (Figure 2, Pathway 3). [32][33][34] Crucially, the diketopiperazine ring in (+)-dehydrodeoxybrevianamide E ( 9) is already at the oxidation level required for a later Diels-Alder reaction. Our pathway involves a point-topoint chirality transfer via a sequential diastereoselective indole oxidation, stereospecific [1,2]-alkyl shift, and tautomerisation, to give enantiopure azadiene 10.…”