Four isoflavones, isolated from the whole plant of Azorella madreporica, were identified as angustone C (1), alpinumisoflavone (2), licoisoflavone A (3) and isolupalbigenin (4) by spectroscopic studies. The compounds were evaluated for antibacterial and gastroprotective activities. This is the first time that isoflavonoids have been reported in this genus.
Two new diterpenes,2-acetoxy-13-hydroxy-mulin-11-ene and 2-acetoxy-mulin-11, 13-diene,have been isolated from the aerial parts of Azorella spinosa and their structures determined by spectroscopic and conventional chemical methods. Furthermore, 2, 13-dihydroxy-mulin-11-ene was obtained using a basic hydrolysis of the first compound. Two diterpenes reported for other Azorella species have also been found, namely mulinolic acid and 13hydroxyazorellane, as well as the triterpene lactone of ursolic acid,quercetin, and 7-hydroxycoumarin. The compounds were evaluated using antibacterial, antioxidant and enzymatic assays; no significant activity was detected.
The title compound, (I) C28H24N4O4, is the trans diastereoisomer of the compound 1-[2-(4-nitrophenyl)-6-(5-phenyl-3-isoxazolyl)-1,2,3,4-tetrahydro-4-quinolinyl]-2-pyrrolidinone monohydrate, (II) [Gutierrez et al. (2011 ▶). Acta Cryst. E67, o175–o176]. The most obvious differences between the diastereoisomers are the dihedral angles between the isoxazole ring and the benzene and phenyl rings [47.0 (2); 56.4 (2) and 33.3 (2); 11.0 (2)°, respectively, for (II) 75.4 (2) and 5.8 (3), respectively, for (I)]. In the crystal of (I), the molecules are linked by N—H⋯O interactions into a chain along [001] with graph-set notation C(8).
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