Chemistry and evolution of the Piperaceae

The chemistry of members of the family Piperaceae is of great interest owing to the variety of biological properties displayed. A survey of structural diversity and bioactivity reveals that groups of species specialize in the production of amides, phenylpropanoids, lignans and neolignans, benzoic acids and chromenes, alkaloids, polyketides, and a plethora of compounds of mixed biosynthetic origin. Bioassays against Cladosporium cladosporioides and C. sphaerospermun have resulted in the characterization of various amides, prenylated phenolic compounds, and polyketides as potential classes of antifungal agents. Studies on the developmental process in seedlings of Piper solmsianum have shown that phenylpropanoid are produced instead of the tetrahydrofuran lignans found in adult plants. In suspension cultures of P. cernuum and P crassinervium, phenylethylamines and alkamides predominate, whereas in the adult plants prenylpropanoids and prenylated benzoic acids are the respective major compound classes. Knowledge of the chemistry, bioactivity, and ecology of Piperaceae species provides preliminary clues for an overall interpretation of the possible role and occurrence of major classes of compounds.

Antifungal polysulphides from Petiveria alliacea L.

Bioactivity-directed fractionation of the CH2Cl2/MeOH (2:1, v/v) extract of the roots of Petiveria alliacea, using mutant yeast strains of Saccharomyces cerevisiae and fungi Cladosporium cladosporioides and C. sphaerospermum led to the isolation of dipropyl disulphide (1), dibenzyl sulphide (2), dibenzyl disulphide (3), dibenzyl trisulphide (4), dibenzyl tetrasulphide (5), benzylhydroxymethyl sulphide (6) and di(benzyltrithio) methane (7). of these, 5-7 are new compounds and this is the first report of the natural occurrence of 2 and 3. (C) 2001 Elsevier B.V. Ltd. All rights reserved.

Antifungal amide from leaves of Piper hispidum

Bioactivity-guided fractionation of a CH2Cl2 extract from leaves of Piper hispidum (Piperaceae) yielded a new pyrrolidine amide, N-[7-(3',4'-methylenedioxyphenyl)-2(Z),4(Z)-heptadienoyl] pyrrolidine 1, in addition to two known amides N-[5-(3',4'-methylenedioxyphenyl)-2(E)-pentadienoyl]pyrrolidine and N-[2-(3',4'-methylenedioxy-6'-methoxyphenyl)-2(Z)-propenoyl]pyrrolidine. The structure of compound 1 was elucidated by interpretation of spectral data, including ES-MS. Compound 1 showed antifungal activity against Cladosporium sphaerospermum.

Antifungal amides from Piper arboreum and Piper tuberculatum

In continuation of our study of the Piperaceae we have isolated several amides, mainly those bearing isobutyl, pyrrolidine, dihydropyridone and piperidine moieties. Bioactivity-guided fractionation of extracts from leaves of Piper arboreum yielded two new amides, N-[10-(13,14-methylenedioxyphenyl)-7(E),9(Z)-pentadienoyl]-pyrrolidine (1), arboreumine (2) together with the known compounds N-[10-(13,14-methylenedioxyphenyl)-7(E)-pentaenoyl]-pyrrolidine (3) and N-[10-(13,14-methylenedioxyphenyl)-7(L, 9(E)-pentadienoyl]-pyrrolidine (4). Catalytic hydrogenation of 3 yielded the amide iV-[10-(13,14-methylenedioxyphenyl)-pentanoyl]-pyrrolidine (5). We also have isolated six amides (6-11) and two antifungal cinnamoyl derivatives (12, 13) from seeds and leaves of Piper tuberculatum. Compounds 1-11 showed antifungal activity as determined by direct bioautography against Cladosporium sphaerospermum while compounds 3-4 and 6-13 also showed antifungal activity against C. cladosporioides. (C) 2002 Published by Elsevier B.V. Ltd.

Biological activity of Gomphrena elegans Mart. Var. Elegans (Amaranthaceae)

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Triterpenes and saponins from Rudgea viburnioides

A novel triterpene; viburgenin (1), has been isolated from an extract of the ripe fruit rinds of Rudgea viburnioides, together with the known saponins, arjunglucoside I and trachelosperosides B-1 and E-l, and the triterpenes trachelosperogenin B (2) and arjungenin. Compound 2 was previously obtained as a product from enzymatic hydrolysis, and it is reported for the first time as a natural product. The structure of compound 1 was determined as 2α,3β,19α,23,24-pentahydroxyurs-12-ene by extensive use of 1D and 2D NMR spectroscopic methods. Compound 1 exhibited moderate antifungal activity against Cladosporium cladosporioides.

Influence of different drying temperatures on the amount of essential oils and citral content in Cymbopogon citratus (DC) Stapf. - Poaceae

Studies were conducted to show the effect of different temperatures in the drying process on the amount and quality of essential oils of Cymbopogon citratus (DC) Stapf. Leaves were harvested in the experimental field of the Agronomical Sciences College, UNESP, Botucatu, SP, Brazil in September, 1996. Blades of the leaves were cut in small parts (about 1-1,5 cm length), dried for several days at 30°, 50°, 70° and 90°C, until establishment of the weights. In the following process a hydrodistillation, during 2.5 hours, by Clevenger apparatus, was subsidized to extract the essential oils. A higher amount of oil could clearly be collected with the lower drying temperatures, except at 30°C, affected by fungus growing. Aspergillus sp., Penicillium sp., Rhyzopus sp., Cladosporium sp., Trichoderma sp. and Alternaria sp. were observed in the leaves. The analysis of the oil by GC-MS showed the variation of citral concentration of the treatments (86,1 to 95,2%). The results proved it is worthwhile to spend more time and effort in the production process using longer times of careful drying.

nor-Lignans from the leaves of Styrax ferrugineus (Styracaceae) with antibacterial and antifungal activity

Chemical examination of the leaves of Styrax ferrugineus yielded 5-[3'-(β-D-glucopyranosyloxy)propyl]-7-methoxy-2-(3',4'-dime-thoxyphenyl) benzofuran, along with the known nor-lignans 5-(3'-hydroxypropyl)-7-methoxy-2-(3',4'-methylenedioxyphenyl) benzofuran, 5-(3'-hydroxypropyl)-7-methoxy-2-(3',4'-dimethoxyphenyl)benzofuran, 5-[3'-(β-D-glucopyranosyloxy)propyl]-7-methoxy-2-(3', 4'-methylenedioxyphenyl)benzofuran and the lignan, dihydrodehydrodiconiferyl alcohol. All arylpropanoids isolated showed antibacterial and antifungal activities. The structures of the isolates were established by spectroscopic analysis. (C) 2000 Elsevier Science Ltd.

Microbiota fúngica de um prédio com laboratórios da região de Araraquara-SP

From September 2000 to January 2001, airborne fungi were isolated from the building of the Clinical Analyses laboratories, including its didactic and research rooms, in Araraquara São Paulo State, Brazil, by using Andersen, MAS-100® (MERCK) machine, with Sabouraud chloramphenicol medium. After 5 days of incubation at 25°C, the colonies of the fungi were counted, resulting in the identification of 21 taxa. Cladophialophora spp. was the most isolated in internal and external environments as well, followed by Penicillium spp. and Mycelia spp. In accordance with the resolution n° 9, January 2003 (ANVISA), fungi considered unacceptable were found in nine internal environments and one of these presented the amount of fungi above of the acceptable limit. Among the obtained fungi, at least 16 taxa were reported as opportunistic, nine were related to plant diseases and seven were associated to allergy problems.

Benzopyrans from Curvularia sp., an endophytic fungus associated with Ocotea corymbosa (Lauraceae)

An isolate of Curvularia sp. was obtained from the leaves of Ocotea corymbosa, a native plant of the Brazilian Cerrado. The ethyl acetate extract from culture of this fungus afforded two benzopyran derivatives: (2′S)-2-(propan-2′-ol)-5-hydroxy-benzopyran-4-one (2) and 2,3-dihydro-2-methyl-benzopyran-4,5-diol (4); and two known benzopyrans: 2-methyl-5-methoxy-benzopyran-4-one (1) and (2R)-2,3-dihydro-2-methyl-5-methoxy- benzopyran-4-one (3). The structures of 2 and 4 were established on the basis of comprehensive spectroscopic analysis, mainly using 1D and 2D NMR experiments. The benzopyrans 1 and 2 showed weak in vitro antifungal activity against Cladosporium sphaerospermum and C. cladosporioides. Analyses of the biological activities were also carried out on HeLa (human cervix tumor) and CHO (Chinese hamster ovary) cells, aiming to evaluate their potential effects on mammalian cell line proliferation. Results from both cell lines indicated that compound 2 was able to induce cell proliferation: 70% on HeLa cells and 25% on CHO cells. © 2005 Elsevier Ltd. All rights reserved.

New bioactive metabolites produced by Phomopsis cassiae, an endophytic fungus in Cassia spectabilis

Two new metabolites, ethyl 2,4-dihydroxy-5,6-dimethylbenzoate (1) and phomopsilactone (2) were isolated from Phomopsis cassiae, an endophytic fungus in Cassia spectabilis. Their structures were elucidated by 1D and 2D NMR, MS and IR spectral data. Compounds 1 and 2 displayed strong antifungal activity against the phytopatogenic fungi Cladosporium cladosporioides and C. sphaerospermum, as well as cytotoxicity against human cervical tumor cell line (HeLa), in in vitro assays. ©2005 Sociedade Brasileira de Química.

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.

Environmental isolation of black yeast-like fungi involved in human infection

The present study focuses on potential agents of chromoblastomycosis and other endemic diseases in the state of Paraná, Southern Brazil. Using a highly selective protocol for chaetothyrialean black yeasts and relatives, environmental samples from the living area of symptomatic patients were analysed. Additional strains were isolated from creosote-treated wood and hydrocarbon-polluted environments, as such polluted sites have been supposed to enhance black yeast prevalence. Isolates showed morphologies compatible with the traditional etiological agents of chromoblastomycosis, e.g. Fonsecaea pedrosoi and Phialophora verrucosa, and of agents of subcutaneous or systemic infections like Cladophialophora bantiana and Exophiala jeanselmei. Some agents of mild disease were indeed encountered. However, molecular analysis proved that most environmental strains differed from known etiologic agents of pronounced disease syndromes: they belonged to the same order, but mostly were undescribed species. Agents of chromoblastomycosis and systemic disease thus far are prevalent on the human host. The hydrocarbon-polluted environments yielded yet another spectrum of chaetothyrialean fungi. These observations are of great relevance because they allow us to distinguish between categories of opportunists, indicating possible differences in pathogenicity and virulence.

Qualidade fisiológica e sanitária de sementes de mamona submetidas a diferentes tratamentos químicos

The use of fungicides for treating seeds has become an essential measure in the control of pathogens. However, the effectiveness of many products is not well-known to some crops. The objective of this research was to evaluate the effect of different doses of carbendazin and carboxin + thiram fungicides for controlling pathogens and their interference on the physiologic quality of castor bean seeds. The test consisted of the following treatments (g i.a./100 kg of seeds): carbendazin (15, 30, and 60), carboxin + thiram (25 + 25, 50 + 50, and 100 + 100), formol 0.15% (v/v), and control (distilled water). The physiologic quality of the seeds was determined by germination, first counting, field emergence, speed emergence index, length, fresh and dry weight of the aerial part, and electrical conductivity. There were no statistical differences for germination and fresh and dry matter index. The treatment with formol provided lower values for first counting and field emergence. Seeds treated with fungicides presented higher values for electrical conductivity, but did not differ, statistically, among themselves. The fungi Cladosporium spp.; Bipolaris spp.; Curvularia spp.; Aspergillus flavus; Aspergillus niger; Rhizopus sp.; Penicillium sp.; Rhizoctonia sp.; Verticillium sp.; Fusarium sp.;Arthrobotrys sp.; and Epicocum sp. were identified. All tested products, independently of the dose, provided efficient control for pathogens.

Descrição da diversidade de fungos associados a formigas Attini por método independente de cultivo

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