Triterpenoids from Azorella trifurcata (Gaertn.) Pers and their effect against the enzyme acetylcholinesterase

The inhibition of the enzyme acetylcholinesterase is considered as a strategy for the treatment of Alzheimer's disease, senile dementia, ataxia, and myasthenia gravis. Three lanostane- and two cycloartane-type triterpenes, together with two mulinane-type diterpenes were isolated from petroleum ether extract of the whole shrub of Azorella trifurcata (Gaertn.) Pers. Their effect on the enzyme acetylcholinesterase was assessed as well. In addition, this is the first report of these triterpenes in the genus Azorella.

Studies on the isolation and characterization of flavones and triterpenoids from a few plants

In the present scenario, there is an increasing demand for natural products in food industry, pharmaceuticals, cosmetics and agricultural sectors. In this context phytochemical study to identify newer chemicals has got great relevance. Phytochemical studies have become more reliable and encouraging with the development of modern analytical techniques.In the present work the leaves of Piper colubrinum (Piperaceae), aerial parts of Mussaenda fiondosa (Rubiaceae) and Humboldtia vahliana (Leguminosae) and the pericarp of fruits of Artocarpus heterophyllus (Moraceae) were investigated for their secondary metabolites. The major compounds isolated belong to the groups of flavonoids and triterpenoids.Naturally occurring flavonoids have been used widely in chemotaxonomic studies of plants. Flavones and flavonols constitute a group of biosynthetically related natural products. No universal function has been established for flavones and flavonols in plants. However, many functions in individual plants have been demonstrated. These include protection of plants from ultraviolet light, insects and pests; pollinator attractants; antioxidants; plant hormone controllers; enzyme inhibitors and allelopathic agents. Flavonoids are attracting the attention of medical scientists in recent years because of their anticarcinogenic, antiallergic and antiinflammatory properties. The recent discovery that flavonoids are involved in the process of nitrogen fixation in plants also opens the way for agricultural application of these constituents.Triterpenoids are another class of compounds that are ubiquitous in plants. Some triterpenoids present in the latex and resins of plants are believed to be involved in chemical defence against pathogens and herbivores. Triterpenoids possess various biological properties including anti-inflammatory, antifeedant, pesticidal, fungitoxic and antimicrobial activities. Triterpenoids with cytotoxic activity and inhibitory effect on seed germination are also known.

Triterpenoids as Biomarkers of Mangrove Organic Matter in Cochin Estuarine System

This thesis entitled triterpenoids as biomarkers of mangrove organic matter in cochin estuarine system.Mangrove forests, known as rainforests of the sea are one of the most important coastal ecosystems in the world in terms of primary production and coastal protection.Estuaries, the important areas of world’s coastal zones link the carbon cycle of the oceans to the continents.Three mangrove ecosystems and three estuarine stations around Cochin region, southwest coast of India were selected for the present study. The thesis is divided into five chapters. Chapter 1 is the Introduction and it deals with the aim and scope of the present study. Chapter 2 is Materials and Methods. This chapter deals with the nature and general geographical features of the study area. It also contains the details of the sampling and analytical methodology.the present study. Chapter 3 is Geochemistry and it includes the seasonal and spatial variations of the geochemical parameters in the surface sediments.Chapter 4 is Biochemical Composition. It covers the biochemical composition of organic matter in the surface sediments to examine the quality and quantity of organic matter.Chapter 5, Triterpenoid Biomarkers in Sediments, characterize the organic matter in the sediments of the mangrove and estuarine ecosystems under study, to assess the possible sources with the help of triterpenoid biomarkers along with other lipid biomarkers.

Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells

Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption. Maslinic acid, oleanolic acid, erythrodiol, and uvaol are pentacyclic triterpenes, found in the non-glyceride fraction of orujo oil, which have previously been reported to have anti-inflammatory properties. In the present work, we investigated the effect of these minor components on pro-inflammatory cytokine production by human peripheral blood mononuclear cells in six different samples. Uvaol, erythrodiol, and oleanolic acid significantly decreased IL-1 beta and IL-6 production in a dose-dependent manner. All three compounds significantly reduced TNF-alpha production at 100 mu M; however, at 10 mu M, uvaol and oleanolic acid enhanced the generation of TNF-alpha. In contrast, maslinic acid did not significantly alter the concentration of those cytokines, with the exception of a slight inhibitory effect at 100 mu M. All four triterpenes inhibited production of I-309, at 50 mu M and 100 mu M. However, uvaol enhanced I-309 production at 10 mu M. The triterpenic dialcohols had a similar effect on MIG production. In conclusion, this study demonstrates that pentacyclic triterpenes in orujo oil exhibit pro- and anti-inflammatory properties depending on chemical structure and dose, and may be useful in modulating the immune response. (c) 2006 Elsevier Ltd. All rights reserved.

Qualitative determination of indole alkaloids, triterpenoids and steroid of Tabernaemontana hilariana

This paper reports the separation and identification of indole alkaloids, steroids and triterpenoids from the ethanolic extracts of Tabernaemontana hilariana (Apocynaceae). The alkaloidal fractions from the ethanolic extracts obtained (root barks, green fruits, ripe fruits and seeds) were fractionated and analysed by thin-layer chromatography, capillary gas chromatography-flame ionization detection (cGC-FID) as well as by high-resolution gas chromatography-mass spectrometry (HRGC-MS). 3-Hydroxycoronaridine, ibogamine, coronaridine pseudoindoxyl, coronaridine, catharanthine, voacangine hydroxyindolenine, voacangine pseudoindoxyl, tabernanthine, tetraphyllicine, 3-hydroxyvoacangine, voacangine, isovoacangine and 3-oxocoronaridine were identified. The insoluble fraction of ethanolic extracts obtained from the root barks and green fruits were analysed and ten aliphatic constituents were also identified by cGC-FID and HRGC-MS. (C) 1998 Elsevier B.V. B.V. All rights reserved.

Biosynthesis of friedelane and quinonemethide triterpenoids is compartmentalized in Maytenus aquifolium and Salacia campestris

Maytenus aquifolium (Celastraceae) and Salacia campestris (Hippocrateaceae) species accumulate friedelane and quinonemethide triterpenoids in their leaves and root bark, respectively. Enzymatic extracts obtained from leaves displayed cyclase activity with conversion of the substrate oxidosqualene to the triterpenes, 3 beta -friedelanol and friedelin. In addition, administration of (+/-)5-H-3 mevalonolactone in leaves of M. aquifolium seedlings produced radio labelled friedelin in the leaves, twigs and stems, while the root bark accumulated labelled maytenin and pristimerin. These experiments indicated that the triterpenes once biosynthesized in the leaves are translocated to the root bark and further transformed to the antitumoral quinonemethide triterpenoids. (C) 2000 Elsevier B.V. Ltd. All rights reserved.

Biflavones and triterpenoids isolated from Ouratea castaneifolia (DC.) Engl., Ochnaceae

Trata da investigação química das folhas e caule da espécie Ouratea castaneifolia (DC.) Engl., sobre a qual não há registros de estudos químicos ou farmacológicos anteriores. O estudo fitoquímico clássico dos extratos orgânicos do caule e das folhas de O. castaneifolia foi aliado à técnica da cromatografia líquida de alta eficiência (CLAE) e resultou na identificação de dezessete metabólitos: sete triperpenos (friedelina, 3β-friedelinol, α-amirina, β-amirina, lupeol, taraxerol e germanicol), quatro esteróides (sitosterol, estigmasterol e os glucosídeos sitosteril 3-O-β-D-glicopiranosídeo e estigmasteril 3-O-β-D-glicopiranosídeo), uma isoflavona (5,7,4´-trimetoxiisoflavona), uma flavona (5,4´-diidroxi-7,3´,5´-trimetoxiflavona), quatro biflavonas (amentoflavona, 7,7”-O-dimetil-amentoflavona, heveaflavona e tetrametilamentoflavona). A identificação das substâncias foi feita com base na análise de espectros de RMN de 1H, 13C e técnicas bidimensionais. As classes dos metabólitos identificados estão de acordo com aquelas citadas em estudos químicos do gênero Ouratea.

Cell cultures of Maytenus ilicifolia Mart. are richer sources of quinone-methide triterpenoids than plant roots in natura

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

A pentacyclic reaction intermediate of riboflavin synthase

The S41A mutant of riboflavin synthase from Escherichia coli catalyzes the formation of riboflavin from 6,7-dimethyl-8-ribityllumazine at a very low rate. Quenching of presteady-state reaction mixtures with trifluoroacetic acid afforded a compound with an absorption maximum at 412 nm (pH 1.0) that can be converted to a mixture of riboflavin and 6,7-dimethyl-8-ribityllumazine by treatment with wild-type riboflavin synthase. The compound was shown to qualify as a kinetically competent intermediate of the riboflavin synthase-catalyzed reaction. Multinuclear NMR spectroscopy, using various 13C- and 15N-labeled samples, revealed a pentacyclic structure arising by dimerization of 6,7-dimethyl-8-ribityllumazine. Enzyme-catalyzed fragmentation of this compound under formation of riboflavin can occur easily by a sequence of two elimination reactions.

Photochemical alteration of 3-oxygenated triterpenoids: Implications for the origin of 3,4-seco-triterpenoids in sediments

The reactivity of higher plant derived 3-oxy-triterpenoids to sunlight was investigated using a series of pure reference standards both under simulated and real solar exposure. The majority of the exposed compounds showed reactivity to light, particularly to simulated sunlight and among others generated seco-derivatives. While photochemical processes have been suggested for the formation of such compounds, their abundances in some sediments have often been assumed to be the result of diagenetic reworking of parent triterpenoids. Analyses of mangrove leaf waxes, an important known source of taraxerol in coastal ecosystems, showed the presence of the 3,4-seco-derivative dihydrolacunosic acid, which could represent an important biotic source for des-A-triterpenoid precursors to such sediments, and is unrelated to aquatic organic matter diagenesis.