Sesquiterpene lactones as allelochemicals

Six new sesquiterpene lactones, annuolide H ( 3), helivypolides F, H-J ( 4, 11-13), and helieudesmanolide A ( 6), together with known compounds, were isolated from polar bioactive fractions of Helianthus annuus cv. SH-222 and Stella fresh leaf water extracts. Spectroscopic analysis of the new data for 1,2-anhydroniveusin A and 1-methoxy-4,5-dihydroniveusin A corrects some previous assignments. The compounds were tested using the etiolated wheat coleoptile bioassay, and the most active compounds were assayed in standard target species ( STS) ( Lepidium sativum, Allium cepa, Lactuca sativa, Lycopersicon esculentum, and Triticum aestivum) from 5 x 10(-4) to 10(-5) M. The most phytotoxic compounds were helivypolide F and 15-hydroxy-3-dehydrodeoxyfruticin, both of which have a carbonyl group at C-3 conjugated with two double bonds.

Antiprotozoal Sesquiterpene Pyridine Alkaloids from Maytenus ilicifolia

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

4,5-Seco-Guaiane and a Nine-Membered Sesquiterpene Lactone from Holostylis reniformis

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

A DNA-damaging sesquiterpene and other constituents from Frullania nisquallensis

Bioassay-guided fractionation of an MeCOEt extract of Frullania nisquallensis Sull. has furnished a DNA-damaging sesquiterpene, costunolide (1), and two inactive compounds, a sesquiterpene (-)-frullanolide (2) and a tridepside tenuiorin (3). C-13-NMR data of 3 are reported.

Bioactive sesquiterpene pyridine alkaloids from Maytenus aquifolium

Two new sesquiterpene evoninate alkaloids, were isolated together with the known compounds syringaresinol and 4'-O-methyl-(-)-epigallocatechin from the root bark of Maytenus aquifolium. The structures of the two alkaloids were elucidated by interpretation of their spectral data, and both exhibited very weak activity in a mechanism-based DNA-modifying yeast assay. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

Further sesquiterpene pyridine alkaloids from Maytenus aquifolium

Two new sesquiterpene evoninate alkaloids, aquifoliunine E-III and aquifoliunine E-IV, were isolated from the root bark of Maytenus aquifolium. The structures of the new compounds were elucidated on the basis of spectroscopic methods, including ES-MS.

Helivypolide G. A novel dimeric bioactive sesquiterpene lactone

Helivypolide G was isolated from leaves of Helianthus annuus L. cv. Stella. In the course of our ongoing research for new allelochemicals from Helianthus annuus, a novel dimeric bioactive sesquiterpene lactone, helivypolide G has been isolated and characterized from the medium polar active fractions of the leaves of cultivar variety Stella. The monomers are connected through carbons C-15 of each unit and an oxygen bridge, forming an enolic oxane ring. © 2004 Elsevier Ltd. All rights reserved.

Quantitative HPLC analysis of sesquiterpene lactones and determination of chemotypes in Eremanthus seidelii MacLeish & Schumacher (Asteraceae)

Eremanthus seidelii MacLeish & Schumacher has a restricted occurrence to the Brazilian cerrado surrounding the Furnas (MG) reservoir, in environments that have been seriously damaged by human activity. The present phytochemical investigation reveals that the sesquiterpene lactones (SL) 4β,5-dihydro-2′,3′-dihydroxy-15-desoxy-goyazensolide (1) and 4β,5-dihydro-1′,2′-epoxy-eremantholide-C (2) are the major secondary metabolites in E. seidelii leaves, and an HPLC method was developed for their quantitative analysis. HPLC analysis showed no significant seasonal variation in the concentrations of both SL. No qualitative differences were found in the SL patterns of all individuals sampled. However, there is a different SL quantitative pattern among the plants analyzed, pointing to the existence of three quantitative chemotypes of this species, with differences possibly originating from the activity of the enzymes that cyclize the goyazensolide type SL (1) to a eremantholide type SL (2). ©2005 Sociedade Brasileira de Química.

Composition and acaricidal activity of the essential oil of Lychnophora ericoides Mart. to Tetranychus urticae Koch (Acari: Tetranychidae).

The essential oil of the leaves and branches obtained by hydrodistillation of Lychnophora ericoides, collected in the Reserve of Furnas - MG, Brazil, was analyzed by CG/EM (Shimadzu QP2010). The major parts of the volatile components identified in the essential oil of leaves were monoterpenes (44.02%) and the sesquiterpene [alpha]-bisabolol (2.05%). The major acaricidal activity of the essential oil from L. ericoides was observed at 48 (14.55 [mu]L/L of air) and 72 h (8.01 [mu]L/L of air) of exposition. The oviposition of T. urticae oviposition was influenced by the essential oil, but the eclosion of eggs was not affected.

Biological effects of Ocimum gratissimum L. are due to synergic action among multiple compounds present in essential oil

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)

Classification of Aristolochia species based on GC-MS and chemometric analyses of essential oils

Essential oils were obtained from roots of 10 Aristolochia species by hydrodistillation and analysed by GC MS. A total of 75 compounds were identified in the analysed oils. Multivariate analyses of the chemical constituents of the roots enabled classification of the species into four morphological groups. These forms of analysis represent an aid in identification of further specimens belonging to these species. (C) 2007 Elsevier Ltd. All rights reserved.

Aromatic compounds from three Brazilian Lauraceae species

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

In vitro activity of Artemisia annua L (Asteraceae) extracts against Rhipicephalus (Boophilus) microplus

A atividade de extratos vegetais sobre parasitas pode indicar grupos de substâncias de uso potencial no controle de Rhipicephalus (Boophilus) microplus. O objetivo do presente estudo foi investigar a ação in vitro de extratos de Artemisia annua sobre esta espécie. A concentração das lactonas sesquiterpênicas artemisinina e deoxiartemisinina presentes nos extratos vegetais, foi quantificada via cromatografia líquida de alta eficiência. Quatro extratos produzidos a partir do extrato bruto concentrado (EBC) foram avaliados sobre larvas pela metodologia do papel impregnado, com leitura após 24 horas de incubação. As fêmeas ingurgitadas foram imersas por cinco minutos no EBC e nos seus quatro extratos derivados, e incubadas para posterior análise dos parâmetros biológicos. Os extratos não tiveram eficácia sobre as larvas nas concentrações avaliadas (de 3,1 a 50 mg.mL-1). O EBC apresentou melhor eficácia sobre as fêmeas ingurgitadas (CE 50 de 130,6 mg.mL-1 e CE 90 de 302,9 mg.mL-1) que os extratos derivados. Esses resultados tendem a confirmar que a ação da artemisinina sobre as fêmeas ingurgitadas de R. (B.) microplus estaria condicionada à sua ingestão através do sangue. Nesse caso, os métodos in vitro seriam inadequados para a efetiva avaliação da ação de A. annua R.(B.) microplus.

Composição química e produtividade dos principais componentes do óleo essencial de Baccharis dracunculifolia DC. em função da adubação orgânica

Objetivou-se avaliar a composição química e produtividade dos principais componentes do óleo essencial de Baccharis dracunculifolia DC. em função de doses de composto orgânico (0, 10, 20, 30, 40 e 50 t ha-1). Foi realizada uma colheita, aos 150 dias após o transplante das mudas. O óleo essencial, da massa seca útil da parte aérea, foi extraído por hidrodestilação e analisado em cromatógrafo a gás acoplado a espectrômetro de massas (Shimadzu, QP-5000). A identificação dos constituintes químicos foi realizada através da análise comparativa dos espectros de massas das substâncias com o banco de dados do sistema CG-EM (Nist 62.lib), literatura e índice de retenção. Os resultados foram submetidos à análise de variância pelo teste F, às médias obtidas foram submetidas à análise de regressão e o teste Tukey para o efeito das doses de composto orgânico. Os três componentes sesquiterpênicos, E-nerolidol, espatulenol e óxido de cariofileno, perfazem 58,44% da média relativa da composição química do óleo essencial de B. dracunculifolia, composto pela presença de 28 substâncias. Na produtividade dos componentes γ-muroleno, valenceno, δ-cadineno e E-nerolidol as dosagens estudadas influenciaram as plantas, que na dosagem 30 t ha-1 obtiveram os melhores resultados. Se o objetivo no cultivo de B. dracunculifolia for o componente espatulenol as dosagens 30 e 40 t ha-1 obtiveram os melhores resultados. Para a produtividade do componente óxido de cariofileno as dosagens estudadas influenciaram as plantas, que na dosagem 40 t ha-1 obtiveram os melhores resultados.

Antimalarial use of volatile oil from leaves of Virola surinamensis (Rol.) Warb. by Waiapi Amazon Indians

The Amazon Indians Waiapi living in the West of Amapa State of Brazil, treat malaria with an inhalation of vapor obtained from leaves of Viola surinamensis. The essential oil obtained from adult and plantlet leaves was analyzed by GC/MS and 11 monoterpenes, 11 sesquiterpenes and three phenylpropanoids were identified. Plantlet essential oil caused 100% of growth inhibition after 48 h in the development of the young trophozoite to schizont stage and the sesquiterpene nerolidol (100 mu g/ml) was identified as one of the active constituents (100% of growth inhibition was obtained). In addition, examination of [(UC)-C-14]-glucose incorporation showed that activity of nerolidol is related to the inhibition of glycoprotein biosynthesis. (C) 1999 Elsevier B.V. Ireland Ltd. All rights reserved.