Planta Med 2013; 79 - PI16
DOI: 10.1055/s-0033-1352106

Benzophenone glycosides from Hypericum humifusum ssp. austral

A Braca 1, Z Rouis 2, L Faiella 1, F Dal Piaz 3, N Abid 2, M Aouni 2, N De Tommasi 3
  • 1Dipartimento di Farmacia, Università di Pisa, Pisa, Italy
  • 2Laboratoire des Maladies Transmissibles et Substances Biologiquement Actives LR99ES27 Faculté de Pharmacie, Monastir, Tunisia
  • 3Dipartimento di Farmacia, Università di Salerno, Fisciano (SA), Italy

The genus Hypericum (Hypericaceae) comprises 484 species worldwide.1 Traditionally, Hypericum species and in particular H. perforatum have been used for the treatment of burns, rheumatism, hemorrhoids, neuralgia, gastroenteritis, ulcers, hysteria, and depression.2 In the last decade this genus has attracted the attention of phytochemists due to the many phloroglucinols, naphthodianthrones, flavonoids, benzophenones, xanthones, and phenolic acids that have been isolated.2 H. humifusum L. ssp. austral Rouy et Foue, is a glabrous plant, growing in Tunisia, whose length is between 10 and 40 cm.1 The species is known for its use in Spain folk medicine as an agent treating digestive disorders and skin diseases.3 Our previous studies reported the essential oil composition of H. humifusum;4 however no previous phytochemical investigation on this species was carried out to date. In this work, carried out in the frame of a project of the Tunisian Ministry of the Higher Education, Scientific and Technology, we described the isolation and structural identification of six new benzophenones: 2,3',4,5',6-pentahydroxybenzophenone 4-O-(6''-benzoyl)-β-D-glucopyranoside (1), 2,3',4,5',6-pentahydroxybenzophenone 4-O-β-D-glucopyranoside (2), 2,3',4,5',6-pentahydroxybenzophenone 2-O-(2''-benzoyl)-α-L-arabinopyranoside (3), 2,3',4,5',6-pentahydroxybenzophenone 2-O-α-L-arabinopyranoside (4), 2,3',4,5',6-pentahydroxybenzophenone 2-O-(4''-acetyl)-β-D-xylopyranoside (5), 2,3',4,5',6-pentahydroxybenzophenone 3-C-(4''-benzoyl)-β-D-glucopyranoside (6), and five known phenolic derivatives. The structures of all compounds were determined by detailed NMR and HRESIMS analyses.

References:

[1] Crockett, S. I.; Robson N. K. B. Plant Sci. Biotechn. 2011, 5,1 – 13.

[2] Borges, L. V. et al. In Recent Progress in Medicinal Plants; Singh V.K. Ed., 2008, 21, pp. 19 – 37.

[3] Gonzalez-Tejero, M. R. et al. J. Ethnopharmacol. 2008, 116, 341 – 357.

[4] Rouis, Z. et al. Chem. Biodivers. 2012, 9, 806 – 816.