Allelopathic, cytotoxic and antifungic activities of new dihydrophenanthrenes and other constituents of leaves and roots extracts of Banisteriopsis anisandra (Malpighiaceae)

Three new 9,10-dihydrophenanthrenes (2-hydroxy-6-methoxy-7-methyl-9,10-dihydrophenanthrene-1-carbaldehyde, 6, 2-hydroxy-6,8-dimethoxy-7-methyl-9,10-dihydrophenanthrene-1-carbaldehyde, 7, and 2,8-dihydroxy-6-methoxy-7-methyl-9,10-dihydrophenanthrene-1-carbaldehyde, 10), as well eleven known compounds were isolated, for the first time in this species, from ethyl acetate and ethanol extracts from roots and leaves of Banisteriopsis anisandra (Malpighiaceae). Their structures were elucidated on the basis of spectroscopic analysis (IR, 1D and 2D NMR, ESI-MS) and by comparison with authentic samples. New compounds 6 and 10, together with some of the known compounds, had their antitumor (cytotoxic), antifungal and allelopathic activities evaluated. Phenanthrene 10 was active against three cancer cell lines, with IC50 between 5 and 8 mu g/mL and against four Candida species, presenting higher activity than fluconazol against Candida tropicalis; compound 10 also showed good allelopathic activity on germination of Lactucca sativa, and on shoot and radicle growth of Allium cepa. Phenanthrene 6 presented good allelopathic activity in most evaluations made. Published by Elsevier Ireland Ltd on behalf of Phytochemical Society of Europe.