Gilsane Lino von Poser

The Antioxidant Activity of Coumarins and Flavonoids

Coumarins and flavonoids are heterocyclic molecules that have been associated with beneficial effects on human health, such as reducing the risk of cancer, diabetes, cardiovascular and brain diseases. These effects are thought to be related to the radical scavenging effect, due to their antioxidant activities, along with other possible mechanisms, such as anti-inflammatory properties and interaction with several enzymes. Over the past two decades, there have been an increasing number of publications on coumarins and flavonoids, which demonstrate the importance of understanding the chemistry behind the antioxidant activities of both natural and synthesized compounds, considering the benefits from their dietary ingestion as well as pharmacological use. This work aims to review the antioxidant effects of coumarin and flavonoid molecules in humans and the structural aspects that contribute to these effects.

The antidepressant-like effect of Hypericum caprifoliatum Cham & Schlecht (Guttiferae) on forced swimming test results from an inhibition of neuronal monoamine uptake

A crude (ECH) and a purified cyclohexane extract (HCP) of Hypericum caprifoliatum and their main phloroglucinol derivative (HC1) were evaluated regarding their action on monoaminergic systems, more precisely on dopamine. In rats and mice forced swimming test, ECH and HCP dose-dependently reduced the immobility time. The effect of the highest dose was prevented by a prior administration of either sulpiride or SCH 23390 (D(2) and D(1) dopamine receptor antagonist, respectively). HCP (360 mg/kg) decreased the locomotor activity of mice. ECH (90 mg/kg) caused hypothermia and potentiated apomorphine-induced (16 mg/kg) hypothermia in mice. HCP and HC1 inhibited, in a concentration-dependent and monophasic manner, the [(3)H]-DA, [(3)H]-NA and [(3)H]-5HT synaptosomal uptakes, but did not prevent the binding of specific ligands to the monoamine transporters. Moreover, when tested at the concentrations corresponding to its IC(50) on [(3)H]-DA uptake, HC1 did not induce a significant [(3)H]-DA release, while at a higher concentration (200 ng/ml) it enhanced significantly (by 12%) the synaptosomal DA release. These data suggest that the antidepressant-like effect of H. caprifoliatum on the forced swimming test is due to an increase in monoaminergic transmission, resulting from monoamine uptake inhibition, more potently of dopamine, which may be related to their phloroglucinol contents.

Acaricidal properties of the essential oil from Hesperozygis ringens (Lamiaceae) on the cattle tick Riphicephalus (Boophilus) microplus.

Hesperozygis ringens (Benth.) Epling (Lamiaceae) is a strongly aromatic plant employed popularly for its antiparasitic properties. The leaves afforded 4% of essential oil constituted mainly by pulegone (86%). Laboratory tests were carried out to determine the toxicity of the essential oil species on engorged females and larvae of the cattle tick Riphicephalus (Boophilus) microplus using the adult immersion test (AIT) and the larval immersion test (LIT). It was observed that the essential oil at the concentration of 50 microL/mL and 25 microL/mL inhibited the egg laying significatively in relation to the controls and the eggs from these treated females were affected by the oil; the hatching was inhibited in 95% and 30%, respectively. In the LIT it was verified that the LC(99.9), LC(50) and LC(1) was 0.541 microL/mL, 0.260 microL/mL and 0.015 microL/mL, respectively. Pulegone, isolated from the oil, showed similar effect on the females and on the larvae, indicating that it is responsible for the oil activity.

Monoamine oxidase inhibitory activity of some Hypericum species native to South Brazil.

The total methanol crude extracts and petroleum ether, chloroform, and methanol fractions obtained from Hypericum species, H. caprifoliatum, H. carinatum, H. connatum, H. cordatum, H. myrianthum, H. piriai, H. polyanthemum and H. brasiliense, all native to South Brazil, were assayed for monoamine oxidase A (MAO A) and MAO B inhibitory activity in rat brain mitochondrial preparations at concentrations ranging from 1 to 20 μg mL−1. Three benzo‐pyrans, HP1 (6‐isobutyryl‐5,7‐dimethoxy‐2,2‐dimethylbenzopyran), HP2 (7‐hydroxy‐6‐iso‐butyryl‐5‐methoxy‐2,2‐dimethylbenzopyran) and HP3 (5‐hydroxy‐6‐isobutyryl‐7‐methoxy‐2,2‐dimethylbenzopyran) isolated from H. polyanthemum were also tested at maximal concentrations of 150, 150 and 75 μ, respectively. The lipophilic extracts of H. polyanthemum, H. caprifoliatum and H. piriai displayed MAO A inhibitory activity greater than 50%. Among the benzopyrans, only HP3 showed significant activity, with an IC50 value of 22 μ. The total methanol crude extracts of aerial parts from H. carinatum, H. connatum, H. cordatum, H. polyanthemum and H. piriai were evaluated for antidepressant activity in the Porsolts forced swimming test in Wistar rats (270 mg kg−1 day−1; i.p); however, none of them showed activity.

The distribution of iridoids in Bignoniaceae

The distribution of iridoids among the tribes of Bignoniaceae is shown. In the present work, 18 species from the tribes Bignonieae and Tecomeae as well as one from Eccremocarpeae have been investigated. These data combined with those obtained through a literature review were analysed and showed that iridoids occur predominantly in the tribe Tecomeae. In this tribe, a chemical distintion between the genera Tabebuia and Tecoma was observed: The iridoids in Tabebuia are decarboxylated whereas in Tecoma they are C-4 formylated. The species from Bignonieae are poorly investigated and only few reports have been published, however, the iridoids found are mainly C-4 carboxylated. The only exception, Dolichandra cynanchoides (=Macfadyena cynanchoides), with decarboxylated iridoids, is also morphologically abnormal in Bignonieae.

Benzopyrans from Hypericum polyanthemum

From the aerial parts of Hypericum polyanthemum Klotzsch ex Reichardt (Guttiferae), three chromenes, 6-isobutyryl-5,7-dimethoxy-2,2-dimethyl-benzopyran; 7-hydroxy-6-isobutyryl-5-methoxy-2,2-dimethyl-benzopyran and 5-hydroxy-6-isobutyryl-7-methoxy-2,2-dimethyl-benzopyran were isolated. Their structures were determined by NMR spectroscopic analyses.

Terpenóides com atividade sobre o Sistema Nervoso Central (SNC)

The terpenoids are a large group of secondary metabolites which display many activities in the CNS, such as sedative, ansiolytic, antinociceptive, anticonvulsant, pro-convulsant and hallucinogenic. In this work we performed a research on terpenoids that exert effects on the CNS, focusing molecules and neurotransmitter systems related to their actions. The substances approached were classified as mono, sesqui, di, tri and meroterpenoids and include isolated compounds and plants which exert activities mainly on GABAergic, glutamatergic, dopaminergic and opioid neurotransmitter systems.

Acaricidal activity of limonene, limonene oxide and β-amino alcohol derivatives on Rhipicephalus (Boophilus) microplus

Limonene, limonene oxide and eight beta-amino alcohol derivatives obtained by synthesis were investigated for the effect on egg hatchability and mortality rates of newly hatched larvae of the cattle tick Rhipicephalus (Boophilus) microplus. At the doses between 10 microg/ml and 2.5 microg/ml all the compounds were highly lethal to the larvae and some of them showed activity at lower concentrations. The effect on the eggs hatchability was observed in all the treatments.

Screening for the Presence of Hypericins in Southern Brazilian Species of Hypericum

Eight species of Hypericum (H. brasiliense, H. caprifoliatum, H. carinatum, H. connatum, H. cordatum, H. myrianthum, H. piriai and H. polyanthemum) growing in southern Brazil were analyzed by TLC and HPLC for the presence of hypericin and pseudohypericin. Although these polycyclic quinones have been identified in some Hypericum species, they were not detectable in the presently assessed samples. The chemotaxonomy of the taxon is briefly discussed.

Chemical composition and toxicity of the essential oils from Cunila species (Lamiaceae) on the cattle tick Rhipicephalus (Boophilus) microplus.

The essential oils obtained from the aerial parts of five species of Cunila (Lamiaceae) native to Southern Brazil were analyzed by GC and GC/MS. The oil of Cunila angustifolia was characterized by sabinene; Cunila incana is rich in α-pinene and β-pinene, Cunila spicata and Cunila microcephala presented menthofuran as the main component, and in the essential oil of Cunila incisa, the major component was 1,8-cineole. Laboratory tests were carried out to determine the effect of the essential oils of the above cited plants on larvae of the cattle tick Riphicephalus (Boophilus) microplus. C. angustifolia, C. incana, and C. spicata were the most active samples killing almost the totality of the larvae. C. incisa and C. microcephala showed low acaricidal effect.