Phenolics compounds produced by Camarops sp. an endophytic fungus from Alibertia macrophylla (Rubiaceae)

In our search for bioactive compounds from endophytic fungi from brazilian flora, Camarops sp, an endophyte in Alibertia macrophylla (Rubiaceae) showed new and bioactive eremophilane sesquiterpenes when cultivated in corn. These observations led us to grow Camarops sp. in Czapek (semisynthetic medium for cultivation of fungi and composed by sucrose and inorganic salts) in order to investigate the influence of culture medium in the metabolic production. The fungus was cultivated for 28 days on Czapek and then subsequently extracted with ethyl acetate furnishing the crude extract. The ethyl acetate extract was fractioned by flash chromatography column on reversed-phase C-18 silica, followed by reversed-phase HPLC, to yield nine phenolic compounds namely 4-hydroxyphenyllactic acid (1), phenyllactic acid (2), 4-hydroxybenzaldehyde (3), 4-hydroxybenzoic acid (4), 2,4-dihydroxyisobutylbenzoate (5), 2,4-dihydroxypentylbenzoate (6), 2,4-dihydroxyhexylbenzoate (7), 2,4-dihydroxyoctylbenzoate (8) 2,4-dihydroxynonylbenzoate (9). The compounds 5-8 were identified in mixture by using HREIMS, ¹H, ¹³C NMR, 2D NMR (HMQC, HMBC, COSY and NOESY). The structure elucidation of 1 – 9 was achieved by 1D and 2D NMR and mass spectroscopic data. Compounds 4-9 have been isolated from Camarops sp. for the first time and may be involved in antioxidant activities¹ observed in crude extract produced by Camarops sp.. No eremophilane sesquiterpenes were observed in Czapek medium. The isolated phenolic compounds are under biological investigation.

Reference:

[1] Habec, T. R. Prospecção Química e Biológica do Fungo Endofítico Camarops sp. Isolado de Alibertia macrophylla. MSc. Degree, IQ/UNESP, Araraquara, SP, Brazil, 2012.

Acknowledgements: FAPESP, CAPES and CNPq