31 resultados para Sesquiterpene
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The essential oils of leaves of the Pothomorphe peltata (L.) Miq., collected in vegetative and reproductive periods, showed yields of 0.10-0.20%. Analysis of the oil by GC/MS revealed that the predominant components were those of the sesquiterpene class. The major constituents were beta-caryophyllene (39.5-68.0%), germacrene D (6.2-13.3%), (E)-nerolidol (4.8-11.1%) and alpha-humulene (2.1-6.5%).
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The composition of the essential oil from leaves of Cryptocarya mandioccana has been determined by chromatographic fractionation and GC-FID, GC-MS and C-13 NMR analyses, yielding the identification of 64 compounds with predominance of isomeric sesquiterpenes with molecular weights of 204. The main components of the oil obtained by hydrodistillation were beta-caryophyllene, spathulenol, caryophyllene oxide, delta-cadinene, germacrene D, benzaldehyde and bicyclogermacrene. However, the oil obtained by steam distillation contained higher levels of sesquiterpene hydrocarbons, with predominance of P-caryophyllene (C), germacrene D (G) and bicyclogermacrene (B), and was considered to be more representative of the composition of the oil in its natural state. The intraspecific chemical variability of the essential oil obtained by steam distillation was evaluated within populations of trees growing at three separate locations in the state of São Paulo, Brazil. Three distinct chemical groups could be characterised due to differences in the relative percentages of the three main sesquiterpenes from essential oil: CGB [relative contents of C (14-34%), G (5-28%), B (8-15%)], BCG [B (17-34%), C (9-24%), G (12-25%)] and GCB [G (22-42%), C (4-17%), B (7-15%)]. Individuals from groups CGB and BCG were found to be more frequent at south locations while group GCB is predominant in north location. (c) 2006 Elsevier Ltd. All rights reserved.
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Bioactivity-guided fractionation of several bioactive extracts obtained from Cerrado and Atlantic Forest plant species led to the isolation of potent DNA-damaging piperidine 1-5 and guanidine alkaloids 6-9 from Cassia leptophylla and Pterogyne nitens respectively, two common Leguminosae from Atlantic Forest. By means of biotechnological approach on Maytenus aquifolium, a species from Cerrado, moderate DNA-damaging sesquiterpene pyridine alkaloid 10-11 was isolated. Bioassay-guided fractionation on Casearia sylvestris, a medicinal plant species found in Cerrado and Atlantic Forest, led to the isolation of clerodane diterpenes 12-13 which showed effect on DNA. In addition, we have reported several interesting potent antifungal iridoids: 1β-hydroxy-dihydrocornin (14), 1α-hydroxy-dihydrocornin (15), α-gardiol (16), β-gardiol (17), plumericin (18), isoplumericin (19), 11-O-trans-caffeoylteucrein (20); ester derivative: 2-methyl-4-hydroxy-butyl-caffeoate (21), amide N-[7-(3'.4'-methylenedioxyphenyl)-2Z, 4Z-heptadienoyl] pyrrolidine (22) and triterpene viburgenin (23).
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The hexane extract of the stems of Raulinoa echinata afforded the sesquiterpenes germacrene D (6), 1β,6α-dihydroxy-4-(15)-eudesmene (4) and oplopanone (5); the triterpenes squalene, isomultiflorenol (7), isobauerenol (8) and friedelin (9); the protolimonoids melianone (2) and melianodiol (3); and the pyranocoumarin 3-(1′-1′-dimethylallyl)-lomatin (1), which has not been reported previously as a natural product; together with β-sitosterol. The hexane extract and some of these compounds were assayed in vitro against trypomastigote forms of Trypanosoma cruzi. Brine shrimp lethality and antimicrobial activities of the crude extract and pure compounds were also evaluated.
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The sesquiterpenes cadina-4,10(15)-dien-3-one (1) and aromadendr-1(10)-en-9-one (squamulosone) (14) along with the triterpenoid methyl ursolate (21) were incubated with the fungus Mucor plumbeus ATCC 4740. Substrates 1, 14 and ursolic acid (20) were isolated from the plant Hyptis verticillata in large quantities. M. plumbeus hydroxylated 1 at C-12 and C-14. When the iron content of the medium was reduced, however, hydroxylation at these positions was also accompanied by epoxidation of the exocyclic double bond. In total nine new oxygenated cadinanes have been obtained. Sesquiterpene 14 was converted to the novel 2α,13-dihydroxy derivative along with four other metabolites. Methyl ursolate (21) was transformed to a new compound, methyl 3β,7β,21β-trihydroxyursa-9(11),12-dien-28-oate (22). Two other triterpenoids, 3β,28-dihydroxyurs-12-ene (uvaol) (23) and 3β,28-bis(dimethylcarbamoxy)urs-12-ene (24) were not transformed by the micro-organism, however. © 2002 Elsevier Science Ltd. All rights reserved.
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Adult leaves of Melissa officinalis L. (Lamiaceae) harvested during the time of budding had been used in the study of the leaf anatomy in the identification of the secretory structures. The material was fixed in FAA 50%, dehydrated in alcoholic series (ethyl), infiltrated in paraffin, sectioned at 13 mm, staining and later analyzed through optic microscopy. Also it was carried through a study in gaseous chromatography for attainment of the rude essential oil. Analyses of transversal sections of the leaf of Melissa officinalis, has identified the presence of two types of trichomes secretory: peltate and capitate, beyond the presence of trichome tector. Trichome capitate, identified in literature as (type I), presents variations in its morphology in relation to the cells number stalk and the head secretory cells number. The chromatographic analysis of the essential oil identified the presence of monoterpenes, in two major components, responsible for more than 87.8% of the relative composition in the rude oil, beyond sesquiterpenes in smaller proportions.
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In this study, the antiulcerogenic effect of essential oil from Baccharis dracunculifolia was evaluated using the model of acute gastric lesions induced by ethanol. The ulcerative lesion index (ULI) was significantly reduced by oral administration of the essential oil of B. dracunculifolia at doses of 50, 250 and 500 mg/kg which reduced the lesions by 42.79, 45.70 and 61.61%, respectively. The analysis of the chemical composition of the essential oil from B. dracunculifolia by GC showed that this was composed mainly of mono- and sesquiterpenes and the majority compound was nerolidol. Therefore, antiulcerogenic activity of nerolidol (50, 250 and 500 mg/kg) was investigated using ethanol-, indomethacin- and stress-induced ulcer models in rat. In the stress-induced ulcer model, a significant reduction of the ULI in animals treated with nerolidol (50, 250 and 500 mg/kg) and cimetidine (100 mg/kg) was observed, compared to the control group (p < 0.05). The percentage of inhibition of ulcer was 41.22, 51.31, 56.57 and 53.50% in groups treated with 50, 250, 500 mg/kg of nerolidol and 100 mg/kg of cimetidine (positive control), respectively. Regarding ethanol- and indomethacin-induced ulcer models, it was observed that the treatment with nerolidol (250 and 500 mg/kg) significantly reduced the ULI in comparison with the control group (p < 0.05). The dose of 50 mg/kg reduced the parameters analyzed but this was not statistically significant. In the ethanol-induced model percentage of inhibition of ulcer was 34.20, 52.63, 87.63 and 50.87% in groups treated with 50, 250, 500 mg/kg of nerolidol and 30 mg/kg of omeprazol (positive control), respectively. In indomethacin-ulcer the percentage of inhibition of ulcer was 34.69, 40.80, 51.02 and 46.93% in groups treated with 50, 250, 500 mg/kg of nerolidol and 100 mg/kg of cimetidine (positive control), respectively. The results of this study show that nerolidol displays antiulcer activity, as it significantly inhibited the formation of ulcers induced in different animal models. However, further pharmacological and toxicological investigations, to delineate the mechanism(s) of action and the toxic effects, are required to allow the use of nerolidol for the treatment of gastric ulcer. © 2007 Verlag der Zeitschrift für Naturforschung.
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The fat body (FB) consists of two types of cells: throphocytes and oenocytes. Throphocytes are related to intermediary metabolism storing lipids, carbohydrates, and proteins while oenocytes play role in the lipids and lipoproteins production. The vitellogenin is the precursor of egg yolk (vitelline) and is synthesized on FB. The aim of this work was to analyze the effects of hormones acting in bee reproduction, as juvenile hormone (JH) and ecdisteroids (20 HE) on FB cells, where vitellogenin is synthesized. For the study were chose nurse workers that in Melipona quadrifasciata anthidioides present activated ovaries and produce eggs, and virgin queens whose ovaries are not yet activated, presenting only previtellogenic follicles. FB trophocytes from these classes of bees were cultivated in media containing different amounts of JH and 20-HE. The effects on trophocytes cytoplasm reserves of lipids, proteins, and activity of acid phosphatase were compared by observing preparations from cultured FB, treated and control, by transmission electron microscopy (TEM). The results showed that the hormones effects are related to the bee's caste and functional ovary stage. The role of acid phosphatase on mobilization of the trophocyte reserves was also determined. © 2012 Wiley Periodicals, Inc.
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Ethnopharmacological relevance: In Brazilian traditional medicine, Arctium lappa (Asteraceae), has been reported to relieve gastrointestinal symptoms. Aim of the study: In the present study, we investigated the effects of the lactone sesquiterpene onopordopicrin enriched fraction (ONP fraction) from Arctium lappa in an experimental colitis model induced by 2,4,6 trinitrobenzene sulfonic acid and performed experiments to elucidate the underlying action mechanisms involved in that effect. Materials and methods: ONP fraction (25 and 50 mg/kg/day) was orally administered 48, 24 and 1 h prior to the induction of colitis and 24 h after. The inflammatory response was assessed by gross appearance, myeloperoxidase (MPO) activity, tumor necrosis factor alpha (TNF-α) levels and a histological study of the lesions. We determined cyclooxygenase (COX)-1 and -2 protein expressions by western blotting and immunohistochemistry assays. Results: TNBS group was characterized by increased colonic wall thickness, edema, diffuse inflammatory cell infiltration, increased MPO activity and TNF-α levels. On the contrary, ONP fraction (25 and 50 mg/kg) treatment significantly reduced the macroscopic inflammation scores (p<0.05 and p<0.01, respectively) and morphological alterations associated with an increase in the mucus secretion. Similarly, the degree of neutrophil infiltration and the cytokine levels were significantly ameliorated. Moreover, COX-2 expression was up regulated in TNBS-treated rats. In contrast, ONP fraction (50 mg/kg) administration reduced COX-2 overexpression. Conclusions: We have shown that the ONP fraction obtained from Arctium lappa exert marked protective effects in acute experimental colitis, confirming and justifying, at least in part, the popular use of this plant to treat gastrointestinal diseases. © 2013 Elsevier B.V. All rights reserved.
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Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Dry and wet seasons set the phytochemical profile of the Copaifera langsdorffii Desf. essential oils
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Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
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Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
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Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
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Pós-graduação em Agronomia (Horticultura) - FCA
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Many people who live in the cerrado regions use plant species for therapeutic purposes. However, due to intensive extraction of some species, native botanical populations are at risk of disappearing or suffering a dramatic decrease, such as, for instance, individuals of the Lychnophora genus. This has 24 species distributed into the categories vulnerable, endangered, critically endangered, and possibly extinct. These individuals are known in folk medicine as “arnica” and their leaves and flowers are commonly used as anti-inflammatory, analgesic, and healing agents. The chemical profile of the genus is characterized by the presence of sesquiterpene lactones, sesquiterpenes, diterpenes, triterpenes, flavonoids, steroids, polyacetylenes, and caryophyllene derivatives which also have lignans with analgesic activity. Studies with Lychnophora species show significant results with regard to their biological activities against Leishmania amazonensis, Staphylococcus aureus, and Tripanosoma cruzi. Therefore, this study aimed to perform a survey of the morphology, chemical composition, and biological activity, as well as the use and current conservation status of the Lychnophora genus in Brazil.