Compounds identified on hexane and dichloromethane extracts of Salicornia ramosissima

3rd Portuguese Meeting on Medicinal Chemistry and 1st Portuguese-Spanish-Brazilian Meeting on Medicinal Chemistry, Aveiro, 28-30 Novembro 2012.

Some aromatic compounds from dichloromethane extract of Salicornia ramosissima.

6th Spanish-Portuguese-Japanese Organic Chemistry Symposium, Lisboa, de 18 a 20 de Julho de 2012 (Poster Communication).

Constituintes químicos do caule de Protium hebetatuml (Burseraceae)

Protium é um gênero que se destaca na família Burceraceae, compreende cerca de 146 espécies, das quais um pequeno número tem sido estudada do ponto de vista fitoquímico. Neste trabalho, foram isolados os terpenoides α- e β-amirina, os esteroides campesterol, estigmasterol e sitosterol e a cumarina escopoletina, a partir do tronco de Protium hebetatuml. As estruturas destas substâncias foram identificadas por RMN, MS, IV e por comparação com dados espectrais obtidos naa literatura e com amostras autênticas.

Metabólitos secundários de Protium heptaphyllum march

Phytochemical investigation of the resin, fruits, leaves, and trunk of Protium heptaphyllum led to the isolation of the monoterpene p-menth-3-ene-1,2,8-triol, alpha and beta amyrin, quercetin, brein, quercetin-3-O-rhamnosyl, (-) catechin and scopoletin. Their structures were established by 1D and 2D NMR spectroscopy and comparison with published data.

Constituintes químicos de Ipomoea subincana Meisn. (Convolvulaceae)

The chloroform extract of aerial parts of Ipomoea subincana was submitted to different chromatographic procedures which afforded methyl caffeate, ethyl caffeate, methyl 3,4-dimethoxycinnamate, lupeol, alpha-amyrin, beta-amyrin, 3-beta-O-beta-D-glycopiranosyl-sitosterol, beta-sitosterol, stigmasterol, scopoletin, aromadendrane-4beta,10alpha-diol, n-docosyl-cis-p-coumarate and n-icosyl-trans-p-coumarate, vanilin, cinamic acid and vanillic acid. However, from the ethyl acetate extract besides quercetin and 3-O-beta-D-glycopiranosyl-quercetin were isolated methyl 4-O-E-feruloyl-5-O-E-caffeoyl-quinate, methyl 3,5-di-O-E-caffeoyl-quinate and methyl 4-O-E-caffeoyl-quinate. The structures of the compounds were established on the basis of spectral data.

Constituintes químicos de Sebastiania macrocarpa Muell. Arg. (Euphorbiaceae)

The chemical investigation of the methanolic extract of the aerial part of Sebastiania macrocarpa allowed the isolation of the mixture of steroids β-sitosterol and stigmasterol, gallic acid, and scopoletin. The hexane extract of the roots allowed the isolation of the triterpene lupeol and of the macrociclic diterpene (+)-tonantzitlolone. The structures of all compounds isolated were identified on the basis of their spectral data and by comparison of their spectral data with values described in the literature. This is the first report involving the chemical investigation of this species.

Constituintes químicos e atividade inseticida dos extratos de frutos de Trichilia elegans E T. catigua (Meliaceae)

Phytochemical investigation of the fruits extracts of Trichilia elegans and Trichilia catigua (Meliaceae) has led to the identification of the limonoids 11β-acetoxyobacunone, cedrelone, methylangolensate and epimeric mixture of photogedunin besides known coumarins (scoparone, scopoletin, umbeliferone) and the steroids stigmasterol, β-sitosterol, sitostenone and campesterol. The structures of the compounds were proposed by spectroscopic analysis and comparison with literature data. An evaluation of the insecticidal activity of the fruits extracts of Trichilia ssp. was carried out and the extracts of T. elegans revealed to have strong insecticidal activity and the extracts of T. catigua showed moderate larval mortality on Spodoptera frugiperda.

Fitoquímica e quimiossistemática de Conchocarpus marginatus e C. inopinatus (Rutaceae)

Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methyl-arborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus.

Other compounds isolated from Simira glaziovii and the ¹H and 13C NMR chemical shift assignments of new 1-epi-castanopsol

A new triterpene, 1-epi-castanopsol, besides eleven known compounds: sitosterol, stigmasterol, campesterol, lupeol, lupenone, simirane B, syringaresinol, scopoletin, isofraxidin, 6,7,8-trimethoxycoumarin and harman, were isolated from the wood of Simira glaziovii. The structures of the known compounds were defined by 1D, 2D ¹H, 13C NMR spectra data analyses and comparison with literature data. The detailed spectral data analyses allowed the definition of the structure of the new 1-epi isomer of castanopsol and performance of ¹H and 13C NMR chemical shift assignments.

Constituintes químicos e avaliação das atividades antioxidante e anti-inflamatória das raízes de Sabicea brasiliensis wernh (Rubiaceae)

The phytochemical investigation of Sabicea brasiliensis roots led to the isolation of 5-O-caffeoylquinic acid, 3,5- and 4,5-O-dicaffeoylquinics acids, scopoletin, ursolic acid, a mixture of β-sitosterol, stigmasterol and campesterol, daucosterol and saccharose. The structures of the isolated compounds were assigned on the basis of one- and two-dimensional NMR spectroscopic methods and by comparison with literature data. The anti-inflammatory and antioxidant activities of the crude methanolic extract and its fractions were analyzed.

Coumarins and phenolic fingerprints of oak and Brazilian woods extracted by sugarcane spirit

A total of 25 sugarcane spirit extracts of six different Brazilian woods and oak, commonly used by cooperage industries for aging cachaca, were analyzed for the presence of 14 phenolic compounds (ellagic acid, gallic acid, vanillin, syringaldehyde, synapaldehyde, coniferaldehyde, vanillic acid, syringic acid, quercetin, trans-resveratrol, catechin, epicatechin, eugenol, and myricetin) and two coumarins (scopoletin and coumarin) by HPLC-DAD-fluorescence and HPLC-ESI-MS(n). Furthermore, an HPLC-DAD chromatographic fingerprint was build-up using chemometric analysis based on the chromatographic elution profiles of the extracts monitored at 280 nm. Major components identified and quantified in Brazilian wood extracts were coumarin, ellagic acid, and catechin, whereas oak extracts shown a major contribution of catechin, vanillic acid, and syringaldehyde. The main difference observed among oak and Brazilian woods remains in the concentration of coumarin, catechin, syringaldehyde, and coniferaldehyde. The chemometric analysis of the quantitative profile of the 14 phenolic compounds and two coumarins in the wood extracts provides a differentiation between the Brazilian wood and oak extracts. The chromatographic fingerprint treated by multivariate analysis revealed significant differences among Brazilian woods themselves and oak, clearly defining six groups of wood extracts: (i) oak extracts, (ii) jatoba extracts, (iii) cabreuva-parda extracts, (iv) amendoim extracts, (v) canela-sassafras extracts and (vi) pequi extracts.

A new imidazole alkaloid and other constituents from Pilocarpus grandiflorus and their antifungal activity

The stems of Pilocarpus grandiflorus have afforded the new imidazole alkaloid 4,6-dehydro-1,2,4,5-tetrahydro-2,5-dioxopilocarpine in addition to the 17 known compounds germanicol, β-amiryn, ocotillone, stigmast-4-en-3-one, 3β-hydroxy-stigmast-5-en-7-one, 6β-hydroxy-stigmast-4-en-3-one, β-sitosterol, scopoletin, 3-(1′,1′-dimethylallyl)-scopoletin, elisin, dictamine, 4-methoxy-2-quinolone, platydesmine, syringaresinol, syringaldehyde, syringic acid and vanillic acid. Their structures were elucidated on the basis of chemical and spectroscopic evidence. The phenolic compounds vanillic acid and syringaldehyde and the furoquinoline alkaloid platydesmine exhibited antifungal activity against Leucoagaricus gongylophorus, the symbiotic fungus of leaf-cutting ants (Atta sexdens rubropilosa). © 2005 Verlag der Zeitschrift für Naturforschung.

Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives

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

PHYTOCHEMICAL AND CHEMOSYSTEMATICS STUDIES OF Conchocarpus marginatus AND C. inopinatus (Rutaceae)

PHYTOCHEMICAL AND CHEMOSYSTEMATICS STUDIES OF Conchocarpus marginatus AND C. inopinatus (Rutaceae). Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methylarborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus.

Fitoquímica e quimiossistemática de Conchocarpus marginatus e C. inopinatus (Rutaceae)

Phytochemical studies of the leaves and stem have led to the identification of the known acridone alkaloids arborinine, methyl-arborinine, 1-hydroxy-3-methoxy-N-methyl acridone, xanthoxoline, 1,2,3,5-tetramethoxy-N-methylacridone, toddaliopsin C and the new seco acridone alkaloid inopinatin. The known quinoline alkaloids 2-phenyl-1-methyl-quinolin-4(1H)-one, 2-phenyl-1-methyl-7-methoxy-quinolin-4(1H)-one, dictamnine, and the coumarins scopoletin and marmesin were also isolated. The isolated compounds and the distribution of secondary metabolites, which are systematically important, obtained from literature, clearly confirmed that some species formerly described in the genera Angostura and Galipea in fact shall belong to the genus Conchocarpus.