3.1.1. Azaphilones from *Aspergillus* Genus

*Aspergillus* genus is one of the three largest genera where azaphilones can be found. Recently, 23 azaphilones (**1–23**) were isolated from three species (Figure 2 and Table 1). Sassafrin E (**1**), sassafrin F (**2**), and sassafrinamine A (**3**) were isolated from the filamentous fungus *Aspergillus neoglaber* 3020 [33]. Two pigments (Sassafrin E (**1**) and Sassafrin F (**2**)) were yellow and display the azaphilone core fused to the same angular lactone ring with different substituents. The third pigment (sassafrinamine A) (**3**) is purple and displays a nitrogen into the isochromene system substituted with ethyl-1-ol group (Figure 2). The fungus *Aspergillus cavenicola* afforded the nitrogenated azaphilones *trans*-cavernamine (**4**), *cis*cavernamine (**5**), amino acid derivatives of *cis-*cavernamines (**6–10**), hydroxy-cavernamine (**11**), amino acid derivatives of hydroxy-cavernamines (**12–16**), and two oxygenated derivatives *cis* and *trans*-cavernines (**17–18**) [34]. The marine-derived fungus *Aspergillus falconensis* yielded five mitorubrins derivative azaphilones with different benzoyl moieties: two new chlorinated azaphilones, falconensins O and P (**19** and **20**) when the fungus was cultivated in a solid rice medium containing 3.5% NaCl and three additional new azaphilone derivatives (**21–23**) when NaCl was replaced by 3.5% NaBr [35]. From the endophytic *Aspergillus terreus* of *Pinellia ternate,* the undescribed dimer of citrinin penicitrinol Q (**24**) was isolated displaying accentuated Gram-positive antibacterial activity [36].

**Figure 2.** Chemical structures of *Aspergillus* azaphilones **1–2**: sassafrin E-F; **3**: sassafrinamine A; **4**: *trans*-cavernamine; **5**: *cis*-cavernamine; **6–10**: Leu, His, Val, Arg, Trp-cavernamine derivatives; **11**: hydroxy-cavernamines; **12–16**: Leu, His, Val, Arg and Trp-hydroxy-cavernamines.; **17**: *cis*cavernine; **18**: *trans*-cavernine; **19–20**: falconensins O and P; **21–23**: falconensins Q, R, and S; **24**: penicitrinol Q [33–36].
