Planta Med 2013; 79 - PI6
DOI: 10.1055/s-0033-1352096

Megastigmanes and phenolic compounds from Dioclea virgata (Rich.) Amsh. (Leguminosae)

CQ Alves 1, HN Brandão 2, JM David 3, JP David 4, A Kijjoa 5
  • 1Universidade Estadual de Feira de Santana, Departamento de Ciências Exatas, Feira de Santana (44036 – 900) – Bahia, Brasil
  • 2Universidade Estadual de Feira de Santana, Departamento de Saúde, Feira de Santana (44036 – 900) – Bahia, Brasil
  • 3Universidade Federal da Bahia, Instituto de Química, Salvador (40170 – 290) – Bahia, Brasil
  • 4Universidade Federal da Bahia, Faculdade de Farmácia, Salvador (40170 – 290) – Bahia, Brasil
  • 5Universidade do Porto, Chemistry, Largo do Prof. Abel salazar (2, 4099003), Porto, Portugal

Dioclea is a genus which embraces about 50 species and they are distributed in the tropics, especially in forests of Central and South America1. The interest in species of Dioclea is due the presence of lectins showing anticancer activity2. In the folk medicine they are employed in the treatment of different diseases3,4. Dioclea virgata (Rich.) Amsh is a climber plant popularly known in Brazil as “cipó de anauerá”, “cipó pixuma”, “feijão bravo”, “feijãorana” and “mucuna”. To date just D. grandiflora, D. lasiophylla and D. violacea present some phytochemical studies which permitted to isolate bioactive compounds5. Preliminary studies with the CHCl3 extract of the leaves of D. virgata showed antinociceptive activity6. The MeOH extract of leaves of D. virgata was diluted in H2O/MeOH (9:1) and partitioned between CHCl3, and successively with AcOEt:H2O. The CHCl3 extracts was submitted to different chromatographic techniques (CC over sílica gel, flash, Sephadex LH-20) that led to the isolation of (6S,7E,9R)-6,9-dihydroxy-megastigman-4,7-dien-3-one 9-O-β-glucopyranoside and (6S,7E,9R)-6,9-dihydroxy-megastigman-4,7-dien-3-one, besides other flavonoids and phenolic acid derivatives7. The structures of the isolated compounds were elucidated through data analysis of IR spectra, 1H and 13C NMR (BB and DEPT) and bidimensional techniques as well (COSY, HMBC and HMQC).

Acknowledgements: We wish to thank CNPq and FAPESB/PRONEM (Brazil) for financial support.

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[2] Pinto, V. P. T. et al. (2010), Journal of Cancer Research and Experimental Oncology, 2: 54 – 59

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[5] Alves, C. Q.; et al. (2009), 32a RASBQ, Fortaleza-CE

[6] Mota, V. G., et al. (2011), Journal of Biomedicine and Biotechnology, 1: 1 – 10

[7] Alves, C. Q. et al. (2010), Planta Medica, 76:P368