Lychnophorinae (asteraceae): a survey of its chemical constituents and biological activities

This work reviews the current literature about the chemical constituents and the biological activities of the subtribe Lychnophorinae (Vernonieae, Asteraceae). The notable secondary metabolites are sesquiterpene lactones of furanoheliangolide (goyazensolide and eremantholide types) and flavonoids. Some of its most investigated activities include its anti-inflammatory, analgesic, antimicrobial and cytotoxic activities, specially for the Lychnophora and Eremanthus species. The data presented on this paper not only displayed the role played by the Lychnophorinae species as a source of bioactive compounds, but also reinforced the need of further studies involving the species of such subtribe.

Seasonal variation of the major secondary metabolites present in the extract of Eremanthus mattogrossensis Less (Asteraceae: Vernonieae) leaves

The species Eremanthus mattogrossensis, known as "veludo do cerrado" (cerrado velvet), is native to the Brazilian Cerrado. Because the amount of metabolites present in plants may be influenced by biological and environmental factors, here we conducted an HPLC-DAD-MS/MS investigation of the metabolite concentrations found in the MeOH/H2O extract of the leaves of this species. The main compounds were identified and quantified, and the metabolites were grouped by chemical class (caffeoylquinic acids, flavonoids, and sesquiterpene lactone). Statistical analysis indicated a straight correlation between the quantity of metabolites and seasonality, suggesting that environmental properties elicit important metabolic responses.

Complete ¹H and 13C NMR structural assignments for a group of four goyazensolide-type furanoheliangolides

Four goyazensolide-type sesquiterpene lactones - lychnofolide, centratherin, goyazensolide and goyazensolide acetate - were thoroughly studied by NMR experimental techniques. ¹H NMR, 13C NMR {¹H}, COSY, HMQC, HMBC, J-res. and NOE experiments were performed to provide the needed structural information. Complete and unequivocal assignment, including the determination of all multiplicities, was obtained for each structure and the data collections are presented in tables.

Constituintes químicos de Capraria biflora (Scrophulariaceae) e atividade larvicida de seu óleo essencial

Analysis of essential oil from fresh leaves of Capraria biflora allowed identification of fourteen essential oil constituents among which thirteen are sesquiterpene compounds, and α-humulene (43.0%) the major constituent. The essential oil was tested for larvicidal activity against Aedes aegypti showing good activity, with LC50 73.39 µg/mL (2.27 g/mL). Chromatographic studies of extracts from roots and stems allowed the isolation of five compounds: naphthoquinone biflorin, sesquiterpene caprariolide B, the steroid β-sitosterol, the carbohydrate D-mannitol and iridoid myopochlorin first reported in the species C. biflora. The structures of compounds were characterized by spectroscopic data, IR, MS, NMR13C, NMR¹H, NOE, HSQC and HMBC.

Flavonoides e terpenoides de Croton muscicarpa (Euphorbiaceae)

A new sesquiterpene and twelve known compounds comprising eight flavonoids and four terpenoids, were isolated from the leaves, stems, roots and exudate of Croton muscicarpa Müll. Arg.. Their structures were identified as the terpenoids 6α-methoxy-cyperene, dammaradienol, squalene, acetyl aleuritolic acid and spathulenol, and as the flavonoids retusin, 3,7,4'-trimethoxy kaempferol, ombuine, pachipodol, kaempferol, casticin, 5-hydroxy-3,6,7,4'-tetramethoxyflavone and artemetin. All isolated compounds were characterized based on IR, MS, ¹H and 13C NMR, including 2D analyses (COSY, HSQC, HMBC, NOESY) and comparison with data from the literature.

Sesquiterpenos de Ocotea lancifolia (Lauraceae)

Six new eremophilane sesquiterpenes, (rel)-4β,5β,7β-eremophil-9-en-12-oic acid (1), (rel)-4β,5β,7β-eremophil-1(10)-en-12-oic acid (2), (rel)-4β,5β,7β-eremophil-1(10)-en-2-oxo-12-oic acid (3), (rel)-4β,5β,7β-eremophil-9-en-12,8α-olide (4), (rel)-4β,5β,7β-eremophil-9-en-12,8β-olide (5) and (rel)-4β,5β,7β-eremophil-9α,10α-epoxy-12-oic acid (6), were isolated from the leaves of a specimen of Ocotea lancifolia (Lauraceae). Two other known sesquiterpenes, 4β,5β,7β-eremophil-11-en- 10α-ol (7) reported for the first time in the genus Ocotea, and the aromadendrene sesquiterpene, spathulenol (8), were also isolated. Their structures were determined on the basis of spectral data (MS, IR, UV and NMR-1D and 2D) and subsequent comparisons with the literature.

Sesquiterpenos e outros constituintes das folhas de Pterodon pubescens Benth (Leguminosae)

In addition to β-sitosterol, stigmasterol, phaeophitin A, luteolin, kaempferol, quercetin, (+)-catechin, quercetin-3-O-α-L-rhamnopyranoside, rutin, and p-hydroxy-benzoic acid, six known sesquiterpenes, namely (rel)-2β,6β-epoxy-5β-hydroxy-isodaucane, oplopanone, 1β,6α-dihydroxy-4(15)-eudesmene, caryophyllene oxide, α-cadinol, and spathulenol, were isolated from the leaves of Pterodon pubescens (Leguminosae) growing in the Cerrado of Mato Grosso do Sul, Brazil. The (rel)-2β,6β-epoxy-5β-hydroxy-isodaucane corresponds to the correct structure of homalomenol D. The sesquiterpene oplopanone, which bears a modified cadinane skeleton, is being reported for the first time in this genus. The structures of the compounds were determined on the basis of spectral data (MS, IR, and NMR-1D and 2D) and subsequent comparison with data reported in the literature.

Variation of essential oil composition of Tapirira guianensis Aubl. (Anacardiaceae) from two sandbank forests, north of Brazil

Tapirira guianensis (Anacardiaceae) is used in traditional medicine and is important for the recovery of degraded areas and riparian forests because the T. guianensis fruits are highly consumed by wildlife. Volatile components from dried leaves and branches of five individual plants of T. guianensis were collected in two sandbank forests of the State of Pará (Extractive Reserve Maracanã and Area of Environmental Protection Algodoal/Maiandeua), extracted by hydrodistillation using a Clevenger-type apparatus, and analyzed by GC/MS. The ten oils obtained are comprised mostly of sesquiterpene hydrocarbons (58.49 to 100%), with (E)-caryophyllene, β-selinene, α-selinene, β-sesquiphellandrene, and α-zingiberene being the most prominent. The results of the oil compositions were processed by Hierarchical Component Analysis (HCA) allowing the establishment of three groups of essential oils for T. guianensis differentiated by the content of β-selinene/α-selinene (Type I), (E)-caryophyllene (Type II), and β-sesquiphellandrene/α-zingiberene (Type III).

Lychnophoric acid from Lychnophora pinaster: a complete and unequivocal assignment by NMR spectroscopy

The investigation of the hexane extract from aerial parts of Lychnophora pinaster provided, besides others substances, the E-isomer of lychnophoric acid, a sesquiterpene derivative previously isolated from L. affinis.

Foliar anatomy and histochemistry in seven species of Eucalyptus

This work aimed to describe the foliar anatomy of seven species of Eucalyptus, emphasizing the characterization of secretory structures and the chemical nature of the compounds secreted and /or present in the leaves. Anatomical characterization and histochemical evaluation to determine the nature and localization of the secondary compounds were carried out in fully expanded leaves, according to standard methodology. Anatomical differences were verified among the species studied, especially in E. pyrocarpa. Sub-epidermal cavities were the only secretory structures found in the seven species studied, with higher density in E. pellita and lower in E. pilularis. The following compounds were histochemically detected: lipophilic compounds, specifically lipids of the essential or resin-oil type and sesquiterpene lactones found in the lumen of the cavities of the seven species; and hydrophilic compounds, of the phenolic compound type found in the mesophyll of all the species studied and on the epidermis of some of them. The results confirmed the complexity of the product secreted by the cavities, stressing the homogeneous histochemistry nature of these compounds among the species. However, the phenolic compounds results may be an indication of important variations in adaptations and ecological relations, since they show differences among the species.