First secondary metabolites from Herissantia crispa L (Brizicky) and the toxicity activity against Artemia salina Leach

The phytochemical investigation of Herissantia crispa led to the isolation of seven compounds, identified as: sitosterol 3-O-β-D-glucopyranoside, stigmasterol 3-O-β-D-glucopyranoside, 3,5,7,4'-tetrahydroxyflavone (kaempferol), 3,5,7,3',4'-pentahydroxyflavone (quercetin), unpublished in the genus Herissantia, besides β-sitosterol, kaempferol 3-O-β-D-(6''-E-p-coumaroil) (tiliroside) glucopyranoside and kaempferol 3,7-di-O-α-L-ramnopyranoside (lespedin), described for the first time in the species. The structural determination of the compounds was made by means of spectroscopy methods such as Infrared Spectroscopy, ¹H and 13C Nuclear Magnetic Resonance, with the aid of two dimensional techniques, and by comparison with literature data. The toxicity activity of the MeOH extract and lespedin on Artemia salina Leach. was also carried out.

Tropical biodiversity: has it been a potential source of secondary metabolites useful for medicinal chemistry?

The use of natural products has definitely been the most successful strategy in the discovery of novel medicines. Secondary metabolites from terrestrial and marine organisms have found considerable use in the treatment of numerous diseases and have been considered lead molecules both in their natural form and as templates for medicinal chemistry. This paper seeks to show the great value of secondary metabolites and emphasize the rich chemical diversity of Brazilian biodiversity. This natural chemical library remains understudied, but can be a useful source of new secondary metabolites with potential application as templates for drug discovery.

Defence of Agaricus bisporus against toxic secondary metabolites from Trichoderma aggressivum.

Trichoderma spp are effective competitors against other fungi because they are mycoparasitic and produce hydrolytic enzymes and secondary metabolites that inhibit the growth of their competitors. Inhibitory compounds produced by Trichoderma aggressivum, the causative agent of green mold disease, are more toxic to the hybrid off-white strains of Agaricus bisporus than the commercial brown strains, consistent with the commercial brown strain’s increased resistance to the disease. This project looked at the response of hybrid off-white and commercial brown strains of A. bisporus to the presence of T. aggressivum metabolites with regard to three A. bisporus genes: laccase 1, laccase 2, and manganese peroxidase. The addition of T. aggressivum toxic metabolites had no significant effect on MnP or lcc1 transcript abundance. Alternatively, laccase 2 appears to be involved in resistance to T. aggressivum because the presence of T. aggressivum metabolites results in higher lcc2 transcript abundance and laccase activity, especially in the commercial brown strain. The difference in laccase expression and activity between A. bisporus strains was not a result of regulatory or coding sequence differences. Alteration of laccase transcription by RNAi resulted in transformants with variable levels of laccase transcript abundance. Transformants with a low number of lcc transcripts were very sensitive to T. aggressivum toxins, while those with a high number of lcc transcripts had increased resistance. These results indicated that laccase activity, in particular that encoded by lcc2, serves as a defense response of A. bisporus to T. aggressivum toxins and contributes to green mold disease resistance in commercial brown strains.

Development of plant tissue culture of Plumbago rosea Linn. for enhanced production of secondary metabolites

P rosea syn. Indica belong to the family of plumbaginaceae, is an important medicinal plant, cultivated widely in India. The roots of these plant are generally used for medicinal purposes mainly as diuretic, germicidal, vessicant, and abortifacient. It is also used for anaemia, diarrhea, leprosy and common wart. The bark of the root contains orange yellow pigment named plumbagin, a crystalline substance, belongs to the class of naphthoquinone. Its chemical structure is 5-hydroxy 2-methyl 1,4naphthoquinone. Apart from P rosea, P zeylanica, P europea, Drosera and Drosophyllum also contains plumbagin. The most exploited source of plumbagin is, of course, P. rosea roots. The roots contain O.9mg/ g D.Wt. of plumbagin in the roots. These plants grow very slowly and the roots suitable for plumbagin extraction can be obtained only after several years of growth. The productivity of the plant is also rather poor. The focus of the present study was to develop alternative strategies to obtain plumbagin. The tissue culture of P rosea for micropropagation has been studied

An evaluation of the costs of making specific secondary metabolites: does the yield penalty incurred by host plant resistance to insects due to competition for resources?

The presumption that the synthesis of 'defence' compounds in plants must incur some 'trade-off' or penalty in terms of annual crop yields has been used to explain observed inverse correlations between resistance to herbivores and rates of growth or photosynthesis. An analysis of the cost of making secondary compounds suggests that this accounts for only a small part of the overall carbon budget of annual crop plants. Even the highest reported amounts of secondary metabolites found in different crop species (flavonoids, allylisothiocyanates, hydroxamic acids, 2-tridecanone) represent a carbon demand that can be satisfied by less than an hour's photosynthesis. Similar considerations apply to secondary compounds containing nitrogen or sulphur, which are unlikely to represent a major investment compared to the cost of making proteins, the major demand for these elements. Decreases in growth and photosynthesis in response to stress are more likely the result of programmed down-regulation. Observed correlations between yield and low contents of unpalatable or toxic compounds may be the result of parallel selection during the refinement of crop species by humans.

Use of Experimental Design for the Optimization of the Production of New Secondary Metabolites by Two Penicillium Species

A fractional factorial design approach has been used to enhance secondary metabolite production by two Penicillium strains. The method was initially used to improve the production of bioactive extracts as a whole and subsequently to optimize the production of particular bioactive metabolites. Enhancements of over 500% in secondary metabolite production were observed for both P. oxalicum and P. citrinum. Two new alkaloids, citrinalins A (5) and B (6), were isolated and identified from P. citrinum cultures optimized for production of minor metabolites.

Structural variations in root and stem wood of Styrax (Styracaceae) from Brazilian forest and cerrado

The genus Styrax L. (Styracaceae) has a wide distribution in Brazil, occurring in diverse ecosystems. To get a better insight into the ecological adaptations of wood structure, we studied two species, S. camporum and S.ferrugineus from the cerrado, and three species, S. latifolium, S. martii and S. leprosus from the Atlantic forest. For each species, the wood of root and stem was analyzed separately and observations included qualitative as well as quantitative wood characteristics. The results show that there were significant anatomical differences between the forest and cerrado species as well as between the root and stem wood within single species. Quantitatively, the most informative features in the root wood that separated the forest from the cerrado, species were diameter, length and number of vessels, length of fibres, and width and frequency of rays. In the stem wood, length and frequency of vessels, length of fibres, and width and frequency of rays were the most informative features. In contrast to the forest species, which had larger vessel diameters in their stem wood, the cerrado species had larger vessel diameters in their root wood. The calculated vulnerability index indicates that all Sryrax species have adaptations to mesic conditions. The cerrado species had the smallest index values, which could be related to the seasonally dry condition of this environment.

Evaluating methods for the isolation of marine-derived fungal strains and production of bioactive secondary metabolites

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

Vochysiaceae: secondary metabolites, ethnopharmacology and pharmacological potential

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

Secondary Metabolites of Miconia rubiginosa

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

Tropical biodiversity: has it been a potential source of secondary metabolites useful for medicinal chemistry?

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

Variations in tree community composition and structure in a fragment of tropical semideciduous forest in southeastern Brazil related to different human disturbance histories

In an area of tropical seasonal semideciduous forest, the soil characteristics, floristic composition, physiognomic structure, and the distribution of three regeneration and three dispersal guilds were studied for four stands within the forest that had documented histories of varying degrees of human disturbance. The aim was to study forest regeneration in areas of preserved forest and secondary forest, with parts of both types of forest experiencing either 'intensive' or 'occasional' cattle trampling. The study was carried out in the Sebastiao Aleixo da Silva Ecological Station, Bauru, São Paulo State, Brazil. Two stands were called 'secondary' because they corresponded to forest tracts that were felled and occupied by crops and pastures in the past and then abandoned to forest regeneration ca. 40 years before this study. The other two stands, called 'preserved', corresponded to areas of the fragment where the forest has been maintained with only minor human impacts. The arboreal component of the tree community (diameter at breast height or dbh greater than or equal to 5 cm) was sampled in 20 plots of 40 m x 40 m, and the subarboreal component (diameter at the base of the stem or dbs < 5 cm and height greater than or equal to 0.5 m) in subplots of 40 m x 2 m. Physiognomic features, such as canopy height and density of climbing plants, were registered all over a 5 m x 5 m gridline laid on the sample plots. Soil bulk samples were collected for chemical and textural analyses. Most detected differences contrasted the secondary to the preserved forest stands. The soils of the secondary stands showed higher proportions of sand and lower levels of mineral nutrients and organic matter than those of the preserved stands, probably due to higher losses by leaching and erosion. Compared to the secondary stands, the preserved ones had higher proportions of tall trees, higher mean canopy height, lower species diversity, higher abundance of autochorous and shade-tolerant climax species, and lower abundance of pioneer and light-demanding climax species. Despite the high proportion of species shared by the preserved and secondary stands (108 out of 139), they differed consistently in terms of density of the most abundant species. on the other hand, the secondary and preserved stands held similar values for tree density and basal area, suggesting that 40 years were enough to restore these features. Effects of cattle trampling on the vegetation were detected for the frequency of trees of anemochorous and zoochorous species, which were higher in the stands under occasional and intensive cattle trampling, respectively. The density of thin climbers was lower in the stands with intensive trampling. (C) 2004 Elsevier B.V. All rights reserved.

HPLC-EICD: An Useful Tool for the Pursuit of Novel Analytical Strategies for the Detection of Antioxidant Secondary Metabolites

Living cells are continuously exposed to a variety of challenges that exert oxidative stress and are directly related with senescence and the onset of various pathological conditions such as coronary heart disease, rheumatoid arthritis and cancer. Nevertheless, living organisms have developed a complex antioxidant network to counteract reactive species that are detrimental to life. With the aim of bio-prospecting plant species from the Brazilian Cerrado and Atlantic Forest, we have established a methodology to detect secondary antioxidant metabolites in crude extracts and fractions obtained from plant species. Combining HPLC with an electrochemical detector allowed us to detect micromolecules that showed antioxidant activities in Chimarrhis turbinata (DC) leaf extracts. Comparison with purified flavonoid standards led us to identify the compounds in their natural matrices giving valuable information on their antioxidant capacity.

Chrysobalanaceae: Secondary metabolites, ethnopharmacology and pharmacological potential

Many Chrysobalanaceae species, in special Licania and Parinari, are widely used in folk medicine to treat several diseases. This review describes some aspects of their ethnopharmacology potential, biological activities and the secondary metabolites reported so far for Chrysobalanaceae. The chemical constituents of this family include triterpenoids, diterpenoids, steroids and phenylpropanoids like flavonoids as well as chromones derivatives. © 2012 Springer Science+Business Media Dordrecht.

Bioactive Secondary Metabolites from Phomopsis sp., an Endophytic Fungus from Senna spectabilis

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