Influence Of The Stage Of Ripeness On The Composition Of Iridoids And Phenolic Compounds In Genipap (genipa Americana L.).

Genipap fruits, native to the Amazon region, were classified in relation to their stage of ripeness according to firmness and peel color. The influence of the part of the genipap fruit and ripeness stage on the iridoid and phenolic compound profiles was evaluated by HPLC-DAD-MS(n), and a total of 17 compounds were identified. Geniposide was the major compound in both parts of the unripe genipap fruits, representing >70% of the total iridoids, whereas 5-caffeoylquinic acid was the major phenolic compound. In ripe fruits, genipin gentiobioside was the major compound in the endocarp (38%) and no phenolic compounds were detected. During ripening, the total iridoid content decreased by >90%, which could explain the absence of blue pigment formation in the ripe fruits after their injury. This is the first time that the phenolic compound composition and iridoid contents of genipap fruits have been reported in the literature.

Quantitative determination by HPLC of iridoids in the bark and latex of himatanthus sucuuba

The main iridoids from the bark and latex of Himatanthus sucuuba were isolated and characterised by spectroscopic methods. HPLC was used for the quantitative analyses of these iridoids and the chromatograms of bark and latex showed a similar iridoid composition. Both parts of the plant are used in folk medicine for the treatment of various ailments.

Antifungal iridoids, triterpenes and phenol compounds from Alibertia myrciifolia Sprunge Ex. Schum

The new iridoid glucoside 10-O-vanilloyl-geniposidic acid has been isolated from the aerial parts of Alibertia myrciifolia along with hydroxyhopanone, 3α,22-dihydroxyhopane, ursolic acid, luteolin-3´,4´-dimethyl ether, caffeic acid and geniposidic acid. The structures of the isolated compounds were determined by means of mass spectrometry and nuclear magnetic resonance spectral analyses. The antifungal activities of the iridoids 10-O-vanilloyl-geniposidic acid and geniposidic acid were evaluated against the phytopathogenic fungi strains Colletotrichum gloeosporioides, Fusarium solani and Aspergillus niger.

Antifungal iridoids from the stems of Tocoyena formosa

A new antifungal iridoid compound, together with three active known iridoids, galioside, galioside aglucone, and apodanthoside, as well as 3-O-beta-D-glucopyranosyl-28-O-beta-D-glucopyranosyl quinovic acid and quercetin-3-O-methyl-3-O-beta-D-rhamnopyranoside, were isolated from the stems of Tocoyena formosa. This new compound was characterized by spectral data as 11-O-trans-feruloylteucrein.

Iridoids from the aerial parts of Verbena littoralis (Verbenaceae)

The iridoids, 6S-hydroxy-8S-methyl-4-methylene-hexahydro-cyclopenta[c]pyran-3-one and 6S,9S-dihydroxy-8S-methyl-4methylene-hexahydro-cyclopenta[c]pyran-3-one, were isolated from the aerial parts of Verbena littoralis. Their structures and stereochemistry were elucidated by means of NMR spectral data analysis. Both compounds showed moderate in vitro activity against gram positive and negative bacteria as well as moderate in vivo intestinal peristaltic action in mouse. The iridoids also showed moderate free radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) as well as antioxidant activity, the latter being evidenced by redox properties measured using EICD-HPLC. (C) 2004 Elsevier Ltd. All rights reserved.

Iridoids from Tocoyena formosa

The leaves of Tocoyena formosa afforded two antifungal iridoids α- and β-gardiol, and the new iridoids, mollugoside methyl ester and formosinoside. Formosinoside was characterized as its hexaacetyl derivative.

A new antifungal phenolic glycoside derivative and iridoids and lignans from Alibertia sessilis (Vell.) K. Schum. (Rubiaceae)

A new antifungal phenolic glycoside, 3,4,5-trimethoxyphenyl-1-O-β-D- (5-O-syringoyl)-apiofuranosyl-(1→6)-β-D-glucopyranoside (1), together with four known iridoids, geniposidic acid (2), geniposide (3), 6α-hydroxygeniposide (4) and 6β-hydroxygeniposide (5); two lignans, (+)-lyoniresinol-3α-O-β-D-glucopyranoside (6), (-)-lyoniresinol- 3α-O-β-D-glucopyranoside (7); and two phenolic acids, chlorogenic (8) and salicylic acids (9) and D-manitol (10), were isolated from the ethanolic extract of the stems of Alibertia sessilis. Structures of 1 and of the known compounds were determined by spectroscopic analysis. All compounds isolated were evaluated for their antifungal activities against two phytopathogenic fungi strains Cladosporium cladosporioides and C. sphaerospermum by direct bioautography. ©2007 Sociedade Brasileira de Química.

Fungitoxic non-glycosidic iridoids from Alibertia macrophylla

The aqueous alcohol extract of the leaves of Alibertia macrophylla afforded two epimeric pairs of iridoid aglycones and one of them showed high inhibitory activity against Aspergillus niger, Cladosporium sphaerospermum, C. cladosporioides and Colletotrichum gloesporioides. Three of the compounds are reported for the first time from natural sources. Their structures were established on the basis of spectroscopic studies, mainly through 13C NMR analysis. © 1992.

Ipolamiide and fulvoipolarniide from Stachytarpheta glabra (Verbenaceae): A structural and spectroscopic characterization

The phenylethanoid glycoside acteoside and the iridoids ipolamiide and 4-methoxycarbonyl-7-methylcyclopenta[c]pyran (fulvoipolamiide) were isolated from the leaves of Stachytarpheta glabra. The solid state structure of fulvoipolamiide was confirmed by X-ray diffraction studies. The molecules of fulvoipolamiide are displayed in layers parallel to the crystallographic axis a. This molecule is planar with electron delocalization in the fused ring system and the pyran rings of adjacent layers in the solid state structure are involved in a pi-pi stacking interaction. Raman spectroscopy has also been used to characterize the most important bands present in the spectra of fulvoipolamiide and ipolamiide, and comparison made with literature allows the assignment of some key markers, specially the bands in the 1600-1700 cm(-1) range. (C) 2007 Elsevier B.V. All rights reserved.

Superordem corniflorae: química, etnofarmacologia e farmacologia

Corniflorae (sensu Dahlgren, 1980) is a superorder of the Angiospermae formed by the orders Fouquieriales, Ericales, Eucommiales, Sarraceniales, Cornales and Dipsacales, comprising 50 families with more than 7000 cosmopolitan species. Many of these species are used in tradicional medicine and some of them had their pharmacological activities confirmed. The chemistry of these plants is very diversified. Iridoids, triterpenoids and flavonoids were used as taxonomic markers.

Ésteres triterpênicos de Himatanthus sucuuba (Spruce) Woodson

Bioactivity-guided fractionation from hexane extract of Himatanthus sucuuba barks utilizing Cladosporium sphaerospermum led to the isolation of iridoids plumericin and isoplumericin, which showed higher inhibition against C. sphaerospermum than the antibiotic nistatin. Besides bioactive iridoids were isolated the inactive triterpenes lupeol cinnamate, alpha-amyrin cinnamate and lupeol acetate.

Ácido 15-desmetilisoplumierídeo, um novo iridóide isolado das cascas de Plumeria rubra e do látex de Himatanthus sucuuba

Himatanthus sucuuba and Plumeria rubra are used in folk medicine in Brazil to treat various ailments. The isolation of the new iridoid 15-demethylisoplumieride from the bark of Plumeria rubra L. var. acutifolia (Ait) Woodson and latex of Himatanthus sucuuba (Spruce) Woodson is reported. Other iridoid glycosides were obtained from both plants. The structures of these substances were elucidated by spectral analysis and comparison with data already reported.

Novos constituintes químicos das cascas do caule de Tabebuia heptaphylla

A new triterpene, 3beta,6beta,21beta-trihydroxyolean-12-ene and a new iridoid, 8alpha-methyl-8beta-hydroxy-6beta-(3',4'-dimethoxy)benzoyloxy-1 alpha,3alpha-dimethoxy-octahydro-cyclopenta[c]pyran were isolated from the trunk bark of a specimen of Tabebuia heptaphylla (Bignoniaceae) collected in the "Pantanal" of Mato Grosso do Sul, Brazil. Twelve known compounds were also obtained in this work, comprising four iridoids, 6-O-p-hydroxybenzoylajugol, 6-O-p-methoxybenzoylajugol, 6-O-3",4"-dimethoxybenzoylajugol, 8alpha-methyl-8beta-hydroxy-6beta-(4'-hydroxy)benzoyloxy-1alpha,3 alpha-dimethoxy-octahydro-cyclopenta[c]pyran, a cyclopentene dialdehyde, 2-formyl-5-(3',4'-dimethoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetaldehyde, a phenylethanoid glycoside, verbascoside and three benzoic acid derivatives, p-hydroxybenzoic, p-methoxybenzoic and 3,4-dimethoxybenzoic acids, in addition to squalene, sitostenone and sitosterol. The antioxidant properties of the isolated compounds were also evaluated in this work.

Utilização de detecção por espalhamento de luz evaporativo para a análise de produtos naturais

The interest in the use of evaporative light scattering detector (ELSD) for the analysis of different classes of natural products has grown over the years. This is because this detector has become an excellent alternative compared to other types of detectors, such as the refractive index detector and the ultraviolet (UV) detector. This review describes the basic principles of ELSD functioning and discusses the advantages and disadvantages in using an ELSD for the analysis of organic compounds. Additionaly, an overview, covering the last 23 years, of ELSD applications in natural products analysis (saponins, terpenes, carbohydrates, glycosides, alkaloids, steroids, flavonoids, peptides, polyketides, coumarins and iridoids) is presented and discussed.

Antiplasmodial Natural Products

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