Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

Abstract

The volatile oil and the hexane extract from the leaves of Porcelia macrocarpa (Warm.) R.E. Fries, Annonaceae, were submitted to chromatographic separations. Nine sesquiterpenes (alpha-cubebene, alpha-copaene, germacrene-D, bicyclogermacrene, gamma-cadinene, delta-cadinene, spathulenol, globulol and cis-cubenol) and one diterpene (phytol) were identified in the volatile oil (83.1 % in weight). Two sesquiterpenes (spathulenol and macrocarp-11(15)-en-8-ol), the latter with a novel skeleton, one diterpene (phytol) and two steroids (sistosta-5,25-dien-3beta-ol and sitosta-5,22,25-trien-3beta-ol) were isolated from the hexane extract. These compounds were characterized by ¹H and 13C NMR spectroscopy, including bidimensional analysis and mass spectrometry.

Keywords

• macrocarpane
• spathulenol
• steroids
• sesquiterpenes
• Porcelia macrocarpa