Eudesmane and rearranged eudesmane sesquiterpenes from Nectandra cissiflora

Abstract

Recebido em 12/2/10; aceito em 6/5/10; publicado na web em 24/8/10Four eudesmane-type sesquiterpenes, costic acid (1), 12-carboxyeudesman-3,11(13)-diene (2), viscic acid (3), 3-oxo-g-costic acid (4) and two rearranged eudesmane derivatives, 3a-hydroxyisoiphion-11(13)-en-12-oic acid (5) and 5b-hydroxy-4-oxo-11(13)-dehydroiphionan-12-oic acid (6), in addition to (-)-epicatechin, have been isolated from the trunk bark of Nectandra cissiflora. This is the first reported occurrence in the Lauraceae of 3-6. The structures of the isolated compounds have been established on the basis of 1D and 2D NMR spectroscopic techniques. The 13 C NMR assignments of 3, 5 and 6 are given here for the first time, as well as some corrections to the previously reported chemical shift assignments of 4.Keywords: Nectandra cissiflora; Lauraceae; eudesmanes. INTRODUCTIONNectandra Rol. ex Rottb. is the second largest genus of the Lauraceae in the New World, being restricted to the tropical and subtropical Americas, where most of the species occurs between the tropics of Cancer and Capricorn.1 Forty-three species of this genus can be found in Brazil, mostly in the Atlantic Forest and Amazonia.2 On the other hand, Nectandra cissiflora Nees is a tree widely distributed in Brazil, where it is popularly known as "canela-fedida". To date, no phytochemical studies on Nectandra cissiflora have been reported, although this genus has been the subject of several chemical investigations, being mostly characterized by the presence of neolignans, lignans and aporphine alkaloids and also by terpenoids found in essential oils.3-5 Addingly, phenylpropanoids, sesquiterpenes and butanolides have also been shown to occur as nonvolatile constituents in a few members of Nectandra. 4,6,7 Thus, as part of our ongoing study of Brazilian Lauraceae representatives growing in the "Cerrado" of the central-western region of Brazil, we have investigated the chemical composition of the trunk bark of N. cissiflora. Herein we report the isolation of four eudesmane-and two rearranged eudesmanetype sesquiterpene acids from this plant, in addition to (-)-epicatechin. EXPERIMENTAL General experimental procedures1 H and 13 C 1D and 2D NMR spectra were recorded at 300 MHz ( 1 H) and 75 MHz ( 13 C) on a Bruker DPX-300 spectrometer. Standard pulse sequences were used for homo -and heteronuclear correlation experiments. Column chromatography procedures were performed on silica gel 70-230 and 230-400 mesh, RP-18 silica gel 230-400 mesh and Sephadex LH-20. Reversed phase semi-preparative HPLC separations were performed with a Shimadzu LC-6AD pump, using 21.6 x 250 mm, 5 mm particle size, Phenomenex Luna column, with a flow rate of 10 mL min -1 and monitoring at 210 nm. Plant materialThe trunk bark of N. cissiflora was collected in Campo Grande, Mato Grosso do Sul, Brazil in August 2005 and identified by MSc. Extraction and isolation of chemical constituentsThe air-dried and powdered trunk bark (1.5 kg) of N. cissiflora was exhaustively extracted with ethanol at room temperature and t...

Use of costic acid, a natural extract from Dittrichia viscosa, for the control of Varroa destructor, a parasite of the European honey bee

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Anti-inflammatory, antiallergic and COVID-19 protease inhibitory activities of phytochemicals from the Jordanian hawksbeard: identification, structure–activity relationships, molecular modeling and impact on its folk medicinal uses

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