Aromatic compounds from three Brazilian Lauraceae species

Abstract

INTRODUCTIONThe Lauraceae family comprises 52 genera and approximately 3000 species, mostly from tropical and warm subtropical regions of the world.1 Lauraceae species present several groups of secondary metabolites, most of them aromatic, which seem to be relevant for chemotaxonomic classification in Lauraceae. 2The genus Ocotea comprises ca. 350 species. Previous phytochemical studies have revealed the presence of neolignans, benzylisoquinoline alkaloids, phenylpropanoids, flavonoids and sesquiterpenes, 3 besides a variety of volatile components from its essential oils.1 Ocotea elegans is known as canela de ferro or canela preta in Brazil where it is widespread. Despite its huge distribution, the only study performed on O. elegans reports the isolation of neolignans from the stems by using countercurrent chromatography. 4 Ocotea corymbosa is popularly known as canela de corvo or canela fedorenta in Brazil and its wood is employed in the civil construction industry. 5 Only two studies were performed on O. corymbosa; monoterpenes and sesquiterpenes as well as phytosterols were isolated from the unripe fruits 3 and sesquiterpenes with calamenene skeleton were characterized from its bark. Persea is a genus that comprises ca. 200 species, the most well studied of these being P. americana Mill, known as "avocado fruit". Previous phytochemical studies on avocado seeds identified various classes of natural products such as phytosterols, triterpenes, 7 fatty acids with olefinic and acetylenic bonds, 8 alkylfurans, 9 dimers of flavanols, 10 oligomeric proanthocyanidins 11 and glucosylated abscisic acids. 12 Persea pyrifolia is popularly known as maçaranduba and it is frequently employed in the furniture manufacturing industry. 13 The only study carried out on P. pyrifolia dealt with volatile compounds from the leaves. 14 As part of our on-going program devoted to phytochemical investigations on Brazilian Lauraceae species, in this work we report the isolation of an ester of the 4-O-E-caffeoylquinic acid (1) and three flavonoids (2-4) from O. corymbosa, an aromatic sesquiterpene (5) and a flavonoid (6) from O. elegans as well as four furofuran lignans (7-10) from P. pyrifolia. This is the first chemical study on the leaves of O. elegans and O. corymbosa as well as the first report of nonvolatile compounds from P. pyrifolia. EXPERIMENTAL GeneralAnalytical and preparative HPLC separations were performed by using stainless-steel Phenomenex Luna phenyl-hexyl (250 x 4.6 mm and 250 x 22 mm, 5 and 10 mm particle size, respectively) and Phenomenex Luna C-18 (250 x 4.6 mm and 250 x 22 mm, 5 and 10 mm particle size, respectively). Mobile phases for chromatography were prepared from HPLC grade solvents. Methanol and acetonitrile were obtained from J.T. Baker (Phillipsburg, NJ, USA) and Tedia (Fairfield, OH, USA), respectively. Water was purified in-house with a Millipore Milli-Q system (Billerica, MA, USA). The analytical HPLC separations were carried out using a Shimadzu (Kyoto, Japan) LC-10Ai pump system, a Shimadzu SIL-10Ai aut...

Antimycobacterial and Nitric Oxide Production Inhibitory Activities ofOcotea notatafrom Brazilian Restinga

“…There is only one report on the isolation of the flavonoid isoquercitrin from O. notata , in addition to a proanthocyanidin trimer and flavonoids quercitrin and reynoutrin [ 8 ]. There are reports about isoquercitrin isolation also from O. corymbosa [ 29 ]. No data describing the antimicrobial activity of isoquercitrin were found.…”

Eudesmin attenuates Helicobacter�pylori-induced epithelial autophagy and apoptosis and leads to eradication of H. pylori infection

“…It has previously been demonstrated that eudesmin can be isolated from a number of different plants, including Apiaceae , Rutaceae , Ochnaceae and Magnoliaceae ( 17 , 18 ). The present study, to the best of our knowledge, is the first to describe the isolation of eudesmin from Fatsia polycarpa Hayata.…”

“…Air-dried leaves of F. polycarpa Hayata (7 kg total) were extracted with methanol over three times, following standard extraction procedures ( 17 ). The isolated compound was identified by 1 H NMR and 13 C NMR spectroscopy using a Varian Inova 600 (Bruker Daltonics Inc., Billerica, MA, USA) and electrospray ionisation mass spectrometry using a Bruker Daltonics Esquire HCT (Bruker Daltonics Inc.,) as (+)-eudesmin, through comparison of spectra data in previously reported literature ( 18 ). Eudesmin was dissolved in 0.1% of dimethyl sulfoxide (DMSO) for cell culture experiments.…”

Phenolic constituents of leaves from Persea caerulea Ruiz & Pav; Mez (Lauraceae)

“…These include: flavonoids from Persea gratissima Gaertn (Kruthiventi and Krishnaswamy, 2000), Persea americana (Ding et al, 2007), P. palustris, P. borbonia, Persea littoralis Small, Persea humilis Nash (Wofford, 1974), terpenes from P. indica (Gonz alez-Coloma et al, 1992), lignans from Persea obovatifolia Ksot (Tsai et al, 1996), Persea pyrifolia Nees & Mart. (Batista et al, 2010), Persea japonica Sieb (Wang et al, 1996), P. lingue (Sepulveda-Boza et al, 1990), Persea kurzii Kosterm (Prasitpan et al, 1996), alkaloids from P. japonica (Wang et al, 1996), abscisic acid derivates from P. americana (Ramos et al, 2004), alkylfurans from P. americana (Cesar Rodriguez-Saona et al, 1998a), P. indica (Gonz alez-Coloma et al, 1996, and polyhydroxylated compounds (also sometimes termed "aliphatic acetogenins" and "alkanols") from P. americana (Oberlies et al, 1998;C Rodriguez-Saona et al, 1998b). There are just three reports containing phytochemical data for P. caerulea; two of them focused on the essential oil chemical constituents of leaves and its biological potential against Trypanosoma cruzi Setzer et al, 2007), and the third, described the isolation of catechin, epicatechin, proanthocyanidins B1 and B2 and besitosterol (Cuca, 1978).…”