Antifungal amides from Piper hispidum and Piper tuberculatum

Piper hispidum and Piper tuberculatum accumulate amides bearing isobutyl, pyrrolidine, dihydropyridone and piperidine moieties. The isolation and characterization of several representatives including two hitherto unreported amides were performed by chromatographic techniques and by analysis of spectroscopic data. The antifungal activity of each amide was determined by direct bioautography against Cladosporium sphaerospermum. (C) 2000 Elsevier B.V. Ltd. All rights reserved.

Optimisation of conditions for the extraction of casearins from Casearia sylvestris using response surface methodology

Optimal conditions for the extraction of casearins from Casearia sylvestris were determined using response surface methodology. The maceration and sonication extraction techniques were performed using a 3 x 3 x 3 full factorial design including three acidity conditions, three solvents of different polarities and three extraction times. The yields and selectivities of the extraction of casearins were significantly influenced by acidity conditions. Taking into account all variables tested, the optimal conditions for maceration extraction were estimated to involve treatment with dichloromethane saturated with ammonium hydroxide for 26 h. Similar yields and selectivities for casearins were determined for sonication extraction using the same solvent but for the much shorter time of I h. The best results for stabilisation of the fresh plant material were obtained using leaves that had been oven dried at 40 degrees C for 48 h. Copyright (c) 2006 John Wiley & Sons, Ltd.

Acyl lupeols from Cnidoscolus vitifolius

In addition to 3-acetyl aleuritolic acid, 3 beta-acetyl-, cinnamoyl-, dihydrocinnamoyl-lupeol, a new ester of lupeol has been isolated from the stems of Cnidoscolus vitifolius. Its structure was established to be 3 beta-hexanoyl lupeol by spectroscopic methods. (C) 1998 Elsevier B.V. Ltd. All rights reserved.

6-[omega-arylalkenyl]-5,6-dihydro-alpha-pyrones from Cryptocarya moschata (Lauraceae)

Eleven 6-[omega-arylalkenyl]-5,6-dihydro-alpha-pyrones, cryptomoscatones D2, E1, E2, E3 and F1 and cryptopyranmoscatones A1, A2, A3, B1, B2 and B4, in addition to goniothalamin and cryptofolione, were isolated from branch and stem bark of Cryotocarya moschata, Lauraceae. Their structures were established by spectroscopic methods. (C) 2000 Elsevier B.V. Ltd. All rights reserved.

Lignoids in seedlings of Virola sebifera

Quantitative analysis carried out by high performance liquid chromatography indicated the accumulation of a major secondary compound in seedlings of Virola sebifera which was isolated and identified as the lignan hydroxy-otobain. This lignan occurs only in trace amounts in the seeds, where cyclolignans (aryltetralones) are by far the major components. In addition to hydroxy-otobain, only hydroxy-aryltetralones were detected in the seedlings, indicating a selective process in the translocation of secondary compounds. Copyright (C) 2000 John Wiley & Sons, Ltd.

Composition and antifungal activity of essential oils from Piper aduncum, Piper arboreum and Piper tuberculatum

The composition of essential oils from leaves, stems and fruits of Piper aduncum, P arboreum and P. tuberculatum was examined by means of GC-MS and alltifungal assay. There was a predominance of monoterpenes in P aduncum and P tuberculatum and of sesquiterpenes in P arboreum. P aduncum showed the richest essential oil composition, including linalool. The essential oils from fruits of P. aduncum and R tuberculatum showed the highest antifungal activity with the MIC of 10 mu g as determined against Cladosporium cladosponoides and C. sphaerospermum, respectively. This is the first report of the composition of essential oils from P. tuberculatum.

A comparative analysis of the chemical nature of defensive secretions of Gonyleptidae (Arachnida : Opiliones : Laniatores)

The arachnids of the order Opiliones (harvestmen) produce substances used in defense. In the present paper, we analyzed 22 species of Gonyleptidae to explore the use of defensive substances in taxonomy and evolutionary biology. Thirty-seven different compounds were detected, 18 of which were preliminarily identified. These compounds were mapped onto a phylogenetic tree showing the relationships within the Gonyleptidae. Data from Cosmetidae were used as an outgroup. Five ketones and six alkyl phenols were reported for the first time in harvestmen. (c) 2005 Elsevier Ltd. All rights reserved.

seco-Irldoids from Calycophyllum spruceanum (Rubiaceae)

Three seco-iridoids 7-methoxydidcrrosidc, 6'-O-acetyldiderroside and 8-O-tigloyldiderroside, were isolated from the wood bark of Calycophyllum spruceanum together with the known iridoids loganetin, loganin and the seco-iridoids secoxyloganin, kingiside and diderroside. Their structures were elucidated by means of NMR and MS spectral data analysis. Using NOE correlations and coupling constants, the relative stereochernistry of the new derivatives was established. 7-Methoxydiderroside, 6'-O-acetyldiderroside and the known secoxyloganin and diderroside showed in vitro activity against trypomastigote forms of Trypanosonla Cruzi, with IC50 values of 59.0, 90.2, 74,2 and 84.9 mug/mL, respectively and were compared to the standard gentian violet (IC50 7.5 mug/ml). (C) 2003 Elsevier Ltd. All rights reserved.

Essential oil from leaves of Cryptocarya mandioccana Meisner (Lauraceae): Composition and intraspecific chemical variability

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.

Chemical composition of flavonoids and styrylpyrones and the genetic variability of isozymes in natural populations of Cryptocarya mandioccana Meisner (Lauraceae)

The chemical composition of leaves of 57 trees of Cryptocarya mandioccana from three populations of southeastern Brazil was investigated through HPLC, assaying six flavonoids, seven styrylpyrones, and seven unidentified compounds. From 51 of the former trees, genotypes were obtained from 40 polymorphic loci of 19 isozymes. Cluster analyses of the phytochemical and genetical variation revealed that trees exhibited four chemotypes and five clusters from isozymes, respectively. Discriminant analyses from selected variables of the isozymic and chemical data sets were performed, respectively, in relation to the four chemotypes and the five isozyme clusters. The classification of individuals presented respective error estimates of 9.16% and 13.57%, indicating that the genetic data could explain the clusters from chernotypes and vice versa at acceptable error levels. Linear regressions with Dummy variable showed significant association of locus Skdh-2 with quercetin-3-O-beta-D-glucopyranoside and cryptofolione, indicating that its alleles would be responsible for the chemotype variation between individuals. (c) 2006 Elsevier Ltd. All rights reserved.