The Volatile Profiles and DNA Barcodes of Lauraceae Species from the Ocotea Complex with Occurrence in the Brazilian Amazon.

The Ocotea complex accommodates most of the taxonomic diversity of Neotropical Lauraceae with economic importance and biological potential attributed to their essential oils (EOs) and extracts. However, the botanical taxonomy has had limitations due to the difficulty of identifying and delimiting species and genera. The chemical and molecular markers of Ocotea complex species in Pará state, Brazil, were assessed according to their EO compositions and DNA sequences of matK, trnL-trnF, and ITS regions. The multivariate analysis of EOs constituents has classified them into two main clusters characterized by oils rich in (I) terpenoids and phenylpropanoids and (II) sesquiterpenes. We conducted a phylogenetic analysis of species based on DNA barcode sequences on the Bayesian Inference (PP: 0.70-1,0) and Maximum Likelihood (BS: 72-100 %). The comparison between the volatile profiles and phylogenetic data indicates two main groups for these species collected from the Ocotea complex.

Chemical Diversity and Therapeutic Effects of Essential Oils of Aniba Species from the Amazon: A Review.

Lauraceae families have great diversity in the world's tropical regions and are represented mainly by aromatic shrubs and trees with significant production of essential oils (EOs). This work presents a review of the EO chemical profiles from specimens of Aniba, including their seasonal variations, geographical distributions, and biological activities in the Amazon biome. Based on the survey, 15 species were reviewed, representing 167 oil samples extracted from leaves, twig barks, and woods. Brazilian Amazon was the most representative geographic area in the number of specimens, highlighting the locations Belém, (Pará state, PA) (3 spp., 37 samples), Santarém (PA) (3 spp., 10 samples), Carajás (PA) (3 spp., 7 samples), and Manaus (Amazonas state, AM) (3 spp., 16 samples). The main compound classes identified in oils were benzenoids and phenylpropanoids, represented by 1-nitro-2-phenylethane, benzyl salicylate, benzyl benzoate and methyleugenol, along with terpenoids, especially monoterpenes and sesquiterpenes, such as linalool, α-phellandrene, ß-phellandrene, ß-selinene, and spathulenol. The EOs from Aniba showed considerable variation in the chemical profiles according to season and collection site. The hierarchical cluster analysis classified the samples into two main groups according to chemical composition. This review highlights its comprehensive and up-to-date information on history, conservation, traditional uses, chemosystematics, pharmacological potential of Aniba species.

Arbuscular Mycorrhizal Fungi Colonization Promotes Changes in the Volatile Compounds and Enzymatic Activity of Lipoxygenase and Phenylalanine Ammonia Lyase in Piper nigrum L. 'Bragantina'.

Arbuscular mycorrhizal fungi (AMF) have been used to promote numerous benefits to plants. In this study, we evaluated the symbiosis between AMF species (Rhizophagus clarus, Claroideoglomus etunicatum) and Piper nigrum L. 'Bragantina'. Volatile compounds, lipoxygenase (LOX) and phenylalanine ammonia-lyase (PAL) activities, and total phenolic content were monitored from 1 to 60 days post-inoculation (dpi). Hyphae, arbuscles, and vesicles were observed during the root colonization. In the leaves, AMF induced an increase of sesquiterpene hydrocarbons (54.0%-79.0%) and a decrease of oxygenated sesquiterpenes (41.3%-14.5%) at 7 dpi and 60 dpi (41.8%-21.5%), respectively. Cubenol, the main volatile compound of leaves, showed a significant decrease at 7 dpi (21.5%-0.28%) and 45 dpi (20.4%-18.42%). ß-caryophyllene, the major volatile compound of the roots, displayed a significant reduction at 45 dpi (30.0%-20.0%). LOX increased in the roots at 21, 30, and 60 dpi. PAL was higher in leaves during all periods, except at 60 dpi, and increased at 21 and 45 dpi in the roots. The total phenolic content showed a significant increase only in the roots at 30 dpi. The results suggested that AMF provided changes in the secondary metabolism of P. nigrum, inducing its resistance.

Copaifera of the Neotropics: A Review of the Phytochemistry and Pharmacology.

The oleoresin of Copaifera trees has been widely used as a traditional medicine in Neotropical regions for thousands of years and remains a popular treatment for a variety of ailments. The copaiba resins are generally composed of a volatile oil made up largely of sesquiterpene hydrocarbons, such as ß-caryophyllene, α-copaene, ß-elemene, α-humulene, and germacrene D. In addition, the oleoresin is also made up of several biologically active diterpene acids, including copalic acid, kaurenoic acid, alepterolic acid, and polyalthic acid. This review presents a summary of the ecology and distribution of Copaifera species, the traditional uses, the biological activities, and the phytochemistry of copaiba oleoresins. In addition, several biomolecular targets relevant to the bioactivities have been implicated by molecular docking methods.

Essential Oils from Neotropical Piper Species and Their Biological Activities.

The Piper genus is the most representative of the Piperaceae reaching around 2000 species distributed in the pantropical region. In the Neotropics, its species are represented by herbs, shrubs, and lianas, which are used in traditional medicine to prepare teas and infusions. Its essential oils (EOs) present high yield and are chemically constituted by complex mixtures or the predominance of main volatile constituents. The chemical composition of Piper EOs displays interspecific or intraspecific variations, according to the site of collection or seasonality. The main volatile compounds identified in Piper EOs are monoterpenes hydrocarbons, oxygenated monoterpenoids, sesquiterpene hydrocarbons, oxygenated sesquiterpenoids and large amounts of phenylpropanoids. In this review, we are reporting the biological potential of Piper EOs from the Neotropical region. There are many reports of Piper EOs as antimicrobial agents (fungi and bacteria), antiprotozoal (Leishmania spp., Plasmodium spp., and Trypanosoma spp.), acetylcholinesterase inhibitor, antinociceptive, anti-inflammatory and cytotoxic activity against different tumor cells lines (breast, leukemia, melanoma, gastric, among others). These studies can contribute to the rational and economic exploration of Piper species, once they have been identified as potent natural and alternative sources to treat human diseases.

Chemical Diversity, Biological Activity, and Genetic Aspects of Three Ocotea Species from the Amazon.

Ocotea species present economic importance and biological activities attributed to their essential oils (EOs) and extracts. For this reason, various strategies have been developed for their conservation. The chemical compositions of the essential oils and matK DNA sequences of O. caudata, O. cujumary, and O. caniculata were subjected to comparison with data from O. floribunda, O. veraguensis, and O. whitei, previously reported. The multivariate analysis of chemical composition classified the EOs into two main clusters. Group I was characterized by the presence of α-pinene (9.8-22.5%) and ß-pinene (9.7-21.3%) and it includes O. caudata, O. whitei, and O. floribunda. In group II, the oils of O. cujumary and O. caniculata showed high similarity due amounts of ß-caryophyllene (22.2% and 18.9%, respectively). The EO of O. veraguensis, rich in p-cymene (19.8%), showed minor similarity among all samples. The oils displayed promising antimicrobial and cytotoxic activities against Escherichia coli (minimum inhibitory concentration (MIC) < 19.5 µg·mL-1) and MCF-7 cells (median inhibitory concentration (IC50) ≅ 65.0 µg·mL-1), respectively. The analysis of matK gene displayed a good correlation with the main class of chemical compounds present in the EOs. However, the matK gene data did not show correlation with specific compounds.

Chemical Composition, Antioxidant, and Antimicrobial Activities of Essential Oils of Endlicheria arenosa (Lauraceae) from the Amazon.

The essential oils (EOs) of leaves and twigs of Endlicheria arenosa Chanderb. were obtained by hydrodistillation using a Clevenger-type apparatus and the chemical composition was determined by GC and GC-MS. In total, 47 constituents were identified and sesquiterpene hydrocarbons (77.6%) were the main compounds found in the leaf EO, such as bicyclogermacrene (42.2%), germacrene D (12.5%) and ß-caryophyllene (10.1%). Limonene (33.2%), terpinen-4-ol (15.6%) and δ-cadinol (6.9%) were the predominant constituents in the EO of the twigs. Using the DPPH radical-scavenging method, the EO of the leaves showed the greater radical-scavenging activity (216.5 ± 11.6 mg Trolox equivalents (TE)/mL compared to the EO of the twigs (122.6 ± 6.8 mg TE/mL). Also, the EO of leaves displayed promising antimicrobial activity against Escherichia coli (MIC 19.5 µg x mL(-1)). The present study is the first report about evaluation of volatile oils for this species.