Phytochemical investigation of Azorella madreporica led to the isolation of four known compounds and an unknown chalcone. The structure of the new compound was identified by spectroscopy, including two-dimensional NMR techniques and comparison with published spectral data. The antioxidant activity of chalcone (compound 1) was measured using the 1,2-diphenyl-2-picryl-hydrazyl (DPPH) free radical scavenging assay, and the bioactivity was evaluated against five bacteria (Mycobacterium smegmatis ATCC 14468, clinical isolates of Staphylococcus aureus, Klebsiella granulomatis, Morganella morganii and Escherichia coli) and four cancer cell lines. Docking studies with the tested cancer related proteins revealed nearby values of energy between doxorubicin and compound 1. Besides, protein-ligand interactions correlate with these energy values.
The antibacterial activity of two natural diterpenoids isolated from Azorella compacta together with six semisynthetic derivatives, were evaluated against three bacteria: Staphylococcus aureus, Escherichia coli and Mycobacterium smegmatis. The synthesis of the semisynthetic derivatives 3-5 and 8 have not been previously reported with the methods described in this research. The structures of all diterpenoids were elucidated by NMR 1 H, 13 C and IR spectroscopy. The natural diterpenoids, mulinolic ácid (1) and azorellanol (2) did not present antibacterial activity, but the six derivatives: 12-oxo-11,13-α,α-dihydroxymulin-20-oic ácid (3), 11-oxo-12,13-α,α-dihydroxymulin-20-oic ácid (4) 11,12-dioxo-13-α-hydroxymulin-20-oic ácid (5), 7-acetoxymulin-9,12-diene (6), mulin-9,12-dien-7-ol (7) and 7-acetoxy-12,13-dihydroxymulin-9-en (8) were active against three tested bacteria. The antibacterial activity reported for six semisynthetic diterpenoids may not be comparable with positive control ampicillin but demonstrate the possibility of modification of the biological activity of diterpenoids.
Phytochemical analysis of Azorella compacta resulted in the isolation of six known diterpenes and one unknown norditerpene using chromatographic methods. The structure of this new compound was established by spectroscopic analysis. The bioactivity of the new compound was assessed against six oral bacteria using a drop test method. A high level of growth inhibition was observed against F. nucleatum and P. gingivalis; however, other species such as V. parvula and A. actinomycetemcomitans were not affected.
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