Triterpene Esters Research Articles

Triterpene esters of cirsium setosum and their anti-inflammatory activity

Two new triterpene fatty acid esters, 3β-palmityloxy-12,27-cyclofriedoolean-14-en-11α-ol (1) and 3β-palmityloxy-19α-hydroxyursane (2), together with 3β-hydroxy-11-oxo-olean-12-enyl palmitate (3) were isolated from the potent anti-inflammatory active fraction of the petroleum ether-soluble part of Cirsium setosum ethanol extract. Compound 1 was found to be a rare 12,27-cyclopropane triterpenoid. Their structures were determined through spectral data analysis combined with literature reports. Furthermore, in vitro experiment, compounds 1-3 exhibited significant inhibitory effects on nitric oxide production in lipopolysaccharide-activated mouse RAW264.7 macrophages.

Effect of Ethanol Solution Concentration in the Extraction Process of Centella asiatica L. Bioactive Components Using Microwave-Assisted Extraction (MAE) Method

The Pegagan plant has a scientific name in the form of Centella asiatica L. which is included in the Centella genus, Apiaceae family, and kingdom Plantae. Pegagan (Centella asiatica L.) has distinctive bioactive components, namely triterpene ester glycoside compounds in the form of asiaticoside and madecassoside, and triterpene group compounds in the form of Asiatic acid and madecassic acid. In this study, the extraction of bioactive components from pegagan was carried out using the Microwave-Assisted Extraction (MAE) method and will study the effect of ethanol solvent concentration in the extraction of bioactive compounds. Analysis of the extracted bioactive content was carried out by analyzing the total phenol content using the Folin-Ciocalteau reagent and ANOVA analysis. The results obtained from the study were in the form of total phenol content as an indication of the presence of bioactive compounds, namely at operating conditions of 450 watts of power, 50% ethanol concentration with a radiation time of 15 minutes which resulted in a total phenol content of 21.9244 mg AGE/g sample. In the ANOVA analysis with ethanol solvent, variables that gave a significant response to the total phenol content were microwave power, radiation time, and ethanol concentration with an R-square value of 95.31%. The effect of ethanol concentration on the total phenol content produced, namely the concentration of pure ethanol solvent will produce extracts with the smallest total phenol content, the effect of extraction time on total phenol content, namely the longer extraction time will increase the total phenol content. Maximum total phenol content using ethanol solvent that is, at operating conditions of 450 watts of power, 10% ethanol concentration with a radiation time of 15 minutes which resulted in a total phenol content of 520 mg AGE/g sample.

Triterpene hexahydroxydiphenoyl ester and phenol glucosides from the leaves of Castanopsis eyrie (Champ. ex Benth.) Hutch

As a part of our systematic study on Castanopsis genus (Fagaceae), one new triterpene hydrolysable tannin (1) and two new phenol glucosides (2 and 3) were isolated from the leaves of Castanopsis eyrei (Champ. ex Benth.) Hutch. Compound 1 was identified as a triterpene hexahydroxydiphenoyl (HHDP) ester. This type of compounds has only been isolated from Castanopsis genus. The structures of 1-3 were elucidated by the combination of spectroscopic analysis (MS, 1 D and 2 D NMR) and chemical evidence.

Comparison of Pegagan (Centella asiatica (L.)) Extraction with Ultrasound-Assisted Extraction and Microwave-Assisted Extraction Methods Using Response Surface Methodology

Pegagan (Centella asiatica (L.)) is one of the herbaceous plants that grow, and flowers throughout the year. Pegagan has been used for hundreds of years, especially in the dermatology, and cosmetology industries. Pegagan (Centella asiatica (L.)) has distinctive bioactive components, namely triterpene ester glycoside compounds in the form of asiaticoside, and madecoside as well as triterpene group compounds in the form of asiatic acid, and madecasic acid. There are various extraction methods to produce the following compounds namely, conventional extraction methods, and modern extraction methods. The two methods have differences in the results obtained. Therefore, the difference in the extraction method will determine the result of the difference in the levels of a compound. So that this research was carried out on the effect of Pegagan (Centella asiatica (L.)) extraction using a comparison of the Microwave-Assisted Extraction (MAE), and Ultrasound-Assisted Extraction (UAE) methods on the total phenol content in the Pegagan (Centella asiatica (L.)) extracted. Analysis of the extracteded bioactive content was carried out by analyzing the total phenol content using the Folin-Ciocalteau reagent method and analyzing the data through the Analysis of Response Surface Design expert 11 to see the significance of the research variables. The results obtained from the study are in the form of a comparison of the optimal conditions for the total phenol content, namely, the comparison between the UAE, and MAE methods for Centella asiatica (L.). extracted with ethanol solvent which is more optimal by using the MAE method because in a short time it can produce 1130.7882 mg.

Hibiscus syriacus L.: A Critical Review of Medicinal Utility & Phytopharmacology with Mechanistic Approach

Herbal medicine is an ancient form of medicine that has been used by humans for thousands of years. The vital systems of primordial medicines include Ayurveda, Siddha, Unani, and folk medicine and, the most developed and widely practiced medicinal system in India is Ayurveda. Hibiscus species are commonly shrubs, herbs or trees with many useful properties, of which H. syriacus is one of the prime species of the genus. It is endowed as the national flower of South Korea, commonly known as ‘Rose of Sharon’ and is found along valleys, open slopes, roadsides and sea cliffs. The plant species is used as a medicine in many diseases such as amoebic colitis, hemorrhoids, hemorrhoidal bleeding, migraine, headache, cold, cough, nausea, vomiting, abdominal pain, ascariasis, colitis, diarrhea, dysentery, dyspepsia, gas, stomach ache, hematochezia, ascariasis etc. Several biological activities of the plant are attributed to the presence of various active compounds like botulin, coumarins, fumaric acid, hydroquinone, is vitexin, linoleic acid, nonanoic acid, naringenin acid, Para hydroxybenzaldehyde, palmitic acid, Syracusans A-C, triterpenoids and vanillic acid. Some phytochemicals, including linolenic acid, palmitic acid, hydroxyhibiscone A, hibiscuses D, Syracusans A, pentacyclic triterpene esters, triterpenoid, nonanoic acid, anthocyanins, and others, are responsible for its biological importance like anti-cancer, anti-aging, anti-depressant, anti-fungal, anti-melanogenic, anti-oxidant, cytoprotective, neuroprotective, etc., Detailed information extracted by reviewing the medicinal utilities & Phytopharmacological properties, provide elaborated evidences for the application of H. syriacus in many ailments.

Abubidentin A, New Oleanane-type Triterpene Ester from Abutilon bidentatum and its antioxidant, cholinesterase and antimicrobial activities.

BackgroundThis work describes the phytochemical and biological investigation of aerial parts of Abutilon bidentatum Hochst. Of Saudi origin.MethodologyPetroleum ether fraction of ethanolic extract A. bidentatum was fractionated on a silica gel column and further purified with different chromatographic procedures for the isolation of chemical compounds. The chemical structures of all the pure isolated compounds were elucidated by the interpretation of their spectral data using IR, UV, 1H, 13C NMR, and MS spectroscopy and chemical methods (alkaline hydrolysis) as well as comparison with data reported in the literature. The extract and isolated compounds were evaluated for antioxidant, cholinesterase inhibitory, and antimicrobial activities.ResultsA new oleanane-type triterpene ester, namely abubidentin A (3) (α, 3β, 30-trihydroxy-29-carboxy-olean-9(11), 12-diene-3-dotriacontanoate), along with two known compounds: 2-hydroxydocosanoic acid (1) and stigmasta-22-ene-3-β-ol (2) were isolated from the aerial parts of Abutilon bidentatum Hochst. (Malvaceae). Concerning the biological potential, the abubidentinA displayed antioxidant, cholinesterase inhibitory and antimicrobial activities. AbubidentinA possessed strong antioxidant activity against DPPH and ABTS+ radical scavenging assays. This new triterpene exhibited high inhibition against acetylcholinesterase (IC50 38.13 ± 0.07 µgmL−1) and butyrylcholinesterase (IC50 32.68 ± 0.37 µgmL−1). Abubidentin A displayed promising antimicrobial activity against Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus (125–150 µgmL−1).ConclusionThese findings suggest A. bidentatum can contribute as a source of new biologically active compounds, especially antioxidants and antimicrobial agents.

Phytoconstituents from Moringa oleifera fruits target ACE2 and open spike glycoprotein to combat SARS-CoV-2: An integrative phytochemical and computational approach.

Therapeutic drugs based on natural products for the treatment of SARS-CoV-2 are currently unavailable. This study was conducted to develop an anti-SARS-CoV-2 herbal medicine to face the urgent need for COVID-19 treatment. The bioactive components from ethanolic extract of Moringa oleifera fruits (MOFs) were determined by gas chromatography-mass spectroscopy (GC-MS). Molecular-docking analyses elucidated the binding effects of identified phytocomponents against SARS-CoV-2 spike glycoprotein (PDB ID: 6VYB) and human ACE2 receptor (PDB ID: 1R42) through the Glide module of Maestro software. GC-MS analysis unveiled the presence of 33 phytocomponents. Eighteen phytocomponents exhibited good binding affinity toward ACE2 receptor, and thirteen phytocomponents had a high affinity with spike glycoprotein. This finding suggests that the top 11 hits (Docking score ≥ -3.0kcal/mol) could inhibit SARS-CoV-2 propagation. Intriguingly, most of the phytoconstituents displayed drug-likeness with no predicted toxicity. However, further studies are needed to validate their effects and mechanisms of action. PRACTICAL APPLICATIONS: Moringa oleifera (MO) also called "drumstick tree" has been used as an alternative food source to combat malnutrition and may act as an immune booster. GC-MS analysis unveiled that ethanolic extract of Moringa oleifera fruits (MOFs) possessed 33 active components of pyridine, aromatic fatty acid, oleic acid, tocopherol, methyl ester, diterpene alcohol, triterpene and fatty acid ester and their derivatives, which have various pharmacological and medicinal values. Virtual screening study of phytocomponents of MOF with human ACE2 receptor and SARS-CoV-2 spike glycoprotein exhibited good binding affinity. Based on molecular docking, the top 11 hits (Docking score ≥-3.0kcal/mol) might serve as potential lead molecules in antiviral drug development. Intriguingly, most of the phytoconstituents displayed drug-likeness with no predicted toxicity. Thus, MOF might be used as a valuable source for antiviral drug development to combat COVID-19, an ongoing pandemic.

Characterization of a Pentacyclic Triterpene Acetyltransferase Involved in the Biosynthesis of Taraxasterol and ψ-Taraxasterol Acetates in Lettuce.

Triterpenoids exist in a free state and/or in conjugated states, such as triterpene glycosides (saponins) or triterpene esters. There is no information on the enzyme participating in the production of triterpene esters from free triterpenes. Lettuce (Lactuca sativa) contains various pentacyclic triterpene acetates (taraxasterol acetates, ψ-taraxasterol acetates, taraxerol acetates, lupeol acetates, α-amyrin acetates, β-amyrin acetates, and germanicol acetate). In this study, we report a novel triterpene acetyltransferase (LsTAT1) in lettuce involved in the biosynthesis of pentacyclic triterpene acetates from free triterpenes. The deduced amino acid sequences of LsTAT1 showed a phylogenetic relationship (43% identity) with those of sterol O-acyltransferase (AtSAT1) of Arabidopsis thaliana and had catalytic amino acid residues (Asn and His) that are typically conserved in membrane-bound O-acyltransferase (MBOAT) family proteins. An analysis of LsTAT1 enzyme activity in a cell-free system revealed that the enzyme exhibited activity for the acetylation of taraxasterol, ψ-taraxasterol, β-amyrin, α-amyrin, lupeol, and taraxerol using acetyl-CoA as an acyl donor but no activity for triterpene acylation using a fatty acyl donor. Lettuce oxidosqualene cyclase (LsOSC1) is a triterpene synthase that produces ψ-taraxasterol, taraxasterol, β-amyrin and α-amyrin. The ectopic expression of both the LsOSC1 and LsTAT1 genes in yeast and tobacco could produce taraxasterol acetate, ψ-taraxasterol acetate, β-amyrin acetate, and α-amyrin acetate. However, expression of the LsTAT1 gene in tobacco was unable to induce the conversion of intrinsic sterols (campesterol, stigmasterol, and β-sitosterol) to sterol acetates. The results demonstrate that the LsTAT1 enzyme is a new class of acetyltransferase belong to the MBOAT family that have a particular role in the acetylation of pentacyclic triterpenes and are thus functionally different from sterol acyltransferase conjugating fatty acyl esters.

A Validated HPLC-PDA-HRMS Method to Investigate the Biological Stability and Metabolism of Antiparasitic Triterpenic Esters.

Pentacyclic triterpenes (PTs) are commonly found in medicinal plants with well-known antiparasitic effects. Previous research on C-3 and C-27 triterpenic esters showed effective and selective in vitro antiparasitic activities and in vivo effectiveness by parenteral routes. The aim of this study was to determine triterpenic esters’ stability in different biological-like media and the main microsomal degradation products. An HPLC-PDA method was developed and validated to simultaneously analyze and quantify bioactive triterpenic esters in methanol (LOQ: 2.5 and 1.25–100 µg/mL) and plasma (LOQ: 5–125 µg/mL). Overall, both triterpenic esters showed a stable profile in aqueous and buffered solutions as well as in entire plasma, suggesting gaining access to the ester function is difficult for plasma enzymes. Conversely, after 1 h, 30% esters degradation in acidic media was observed with potential different hydrolysis mechanisms. C-3 (15 and 150 µM) and C-27 esters (150 µM) showed a relatively low hepatic microsomal metabolism (<23%) after 1 h, which was significantly higher in the lowest concentration of C-27 esters (15 µM) (>40% degradation). Metabolic HPLC-PDA-HRMS studies suggested hydrolysis, hydroxylation, dehydration, O-methylation, hydroxylation and/or the reduction of hydrolyzed derivatives, depending on the concentration and the position of the ester link. Further permeability and absorption studies are required to better define triterpenic esters pharmacokinetic and specific formulations designed to increase their oral bioavailability.

Design, Synthesis and Biological Activity of C3 Hemisynthetic Triterpenic Esters as Novel Antitrypanosomal Hits

Research for innovative drugs is crucial to contribute to parasitic infections control and eradication. Inspired by natural antiprotozoal triterpenes, a library of 12 hemisynthetic 3‐O‐arylalkyl esters was derived from ursolic and oleanolic acids through one‐step synthesis. Compounds were tested on Trypanosoma, Leishmania and the WI38 cell line alongside with a set of triterpenic acids. Results showed that the triterpenic C3 esterification keeps the antitrypanosomal activity (IC50≈1.6–5.5 μm) while reducing the cytotoxicity compared to parent acids. Unsaturation of the ester alkyl chain leads to an activity loss interestingly kept when a sterically hindered group replaces the double bond or shields the ester group. An ursane/oleanane C3 hydroxylation was the only important feature for antileishmanial activity. Two candidates, dihydrocinnamoyl and 2‐fluorophenylpropionyl ursolic acids, were tested on an acute mouse model of African trypanosomiasis with significant parasitemia reduction at day 5 post‐infection for the dihydrocinnamoyl derivative. Further evaluation on other alkyl/protective groups should be investigated both in vitro and in vivo.

A comprehensive review of pharmacological and toxicological properties of Cheilocostus speciosus (J.Koenig) C.D.Specht

Cheilocostus speciosus (J.Koenig) C.D.Specht has been commonly used in many indigenous clinical complications to healing various ailments. A list of phytochemicals has been extracted and identified with multiple pharmacological and therapeutic properties from the different parts of C. speciosus (J.Koenig): sterioidal and furostanol saponins, sterioidal and furostanol glycosides, triterpene, phytoserol, sesquiterpenes, benziquinone, and fatty acid esters. Compared with other parts of the C. speciosus (J.Koenig), rhizomes are most extensively studied for their anthelmintic, aphrodisiac, astringent, depurative, expectorant, febrifuge, purgative, and toxin neutralizing properties. Generally, this plant has been reported to have a range of pharmacological activities, including antibacterial, anti-hyperglycemic, anti-inflammatory, anti-pyretic and anti-diuretic, anti-larvicidal, anti-stress, and estrogenic. These findings are highly promising and indicate that the plant needs to be carefully investigated for its diverse therapeutic benefit and associated toxicities and tolerance level. The present review will discuss geographical mapping, morphology, traditional, phytochemistry, and pharmacological prospects of C. speciosus (J.Koenig).

Lipid Fractions, Fatty Acid Profiles, and Bioactive Compounds of Lithospermum officinale L. Seeds

AbstractSeeds of Lithospermum officinale L. from different climatic zones were analyzed for new sources of γ‐linolenic acid (GLA, 18:3n‐6) and stearidonic acid (SDA, 18:4n‐3). Cultured Borago officinalis was also analyzed for comparative purposes. Analyses were conducted for fatty acid (FA) profiles of the glyceride oils from the seeds and in the neutral and polar lipids by gas chromatography (GC); lipid classes by open column chromatography and preparative thin layer chromatography (TLC); and tocopherols, sterols, and phenolic compounds by high‐performance liquid chromatography with diode array detection (HPLC‐DAD), and the later compounds were confirmed by liquid‐chromatography‐mass spectrometry (LC–MS). L. officinale from St. Petersburg Botanical Garden showed the highest percentage of GLA (17.9% of total FA), while wild‐growing L. officinale from the Rostov region contained the highest percentage of SDA (17.2% of total FA). Total FA content ranged from 11.3 to 20.8% of seed weight. Neutral and polar lipids accounted for ~98 and 2.27%, respectively, of total lipids. Five neutral lipid classes were identified (% of NL): triterpene esters (1.3), triacylglycerols (93.1), free FA (1.8), diacylglycerols (1.4), and monoacylglycerols (2.4). The highest tocopherol content was found in samples from Chechen Republic (35.7 mg/100 g), in which the δ isomer was the main component. Samples from the Rostov region had the highest amounts of sterols (83.8 mg/100 g), and Δ5‐avenasterol was the predominant compound in all samples. L. officinale seeds contain high amounts of phenolic compounds (389.9 mg/100 g as upper limit), in which rosmarinic acid is highlighted. Overall, all data suggest the possibility of using L. officinale seed oil in pharmaceutical and cosmetic formulae and as functional food.

Antiprotozoal activities of Triterpenic Acids and Ester Derivatives Isolated from the Leaves of Vitellaria paradoxa

AbstractLeaves of Vitellaria paradoxa, also called “Shea butter tree”, are used in traditional medicine to treat various symptoms including malaria fever, dysentery, or skin infections. Composition of the dichloromethane extract of V. paradoxa leaves possessing antiparasitic activities was investigated. Five pentacyclic triterpenic acids together with 6 ester derivatives were isolated and identified by standards comparison, MS and 1H-NMR analysis. Corosolic, maslinic, and tormentic coumaroyl esters and their corresponding triterpenic acids were isolated from this plant for the first time. The antiparasitic activities of the 11 isolated compounds were evaluated in vitro on Plasmodium falciparum, Trypanosoma brucei brucei, and Leishmania mexicana mexicana and their selectivity determined by cytotoxicity evaluation on WI38 cells. None of the isolated compounds showed good antiplasmodial activity. The antitrypanosomal activity of individual compounds was in general higher than their antileishmanial one. One isolated triterpenic ester mixture in equilibrium, 3-O-p-E/Z-coumaroyltormentic acids, showed an attractive promising antitrypanosomal activity (IC50 = 0.7 µM) with low cytotoxicity (IC50= 44.5 µM) compared to the corresponding acid. Acute toxicity test on this ester did not show any toxicity at the maximal cumulative dose of 100 mg/kg intraperitoneally on mice. In vivo efficacy evaluation of this compound, at 50 mg/kg by intraperitoneal route on a T. b. brucei-infected mice model, showed a significant parasitemia reduction on day 4 post-infection together with 33.3% survival improvement. Further bioavailability and PK studies are needed along with mode of action investigations to further assess the potential of this molecule.

Abelmoschus esculentus subfractions attenuate A\u03b2 and tau by regulating DPP-4 and insulin resistance signals

BackgroundInsulin resistance could be associated with the development of Alzheimer disease (AD). The neuropathological hallmarks of AD are beta amyloid (Aβ) produced from sequential cleavage initiated by β-secretase and degraded by insulin degradation enzyme (IDE), as well as hyperphosphorylation of tau (p-tau). Insulin action involves the cascades of insulin receptor substrates (IRS) and phosphatidylinositol 3-kinase (PI3K), while phosphorylation of IRS-1 at ser307 (p-ser307IRS-1) hinders the response. Our previous report suggested dipeptidyl peptidase-4 (DPP-4) is crucial to insulin resistance, and the subfractions of Abelmoschus esculentus (AE), F1 and F2, attenuate the signaling. Here we aim to investigate whether AE works to reduce Aβ generation via regulating DPP4 and insulin resistance.MethodsThe subfractions F1 and F2 were prepared according to a succession of procedures. F1 was composed by quercetin glycosides and triterpene ester, and F2 contained a large amount of polysaccharides. The in vitro insulin resistance model was established by SK-N-MC cell line treated with palmitate. MTT was used to define the dose range, and thereby Western blot, ELISA, and the activity assay were used to detect the putative markers. One-way ANOVA was performed for the statistical analysis.ResultsTreatment of palmitate induced the level of p-ser307IRS-1. Both F1 and F2 effectively decrease p-ser307IRS-1, and recover the expression of p-PI3K. However, the expression of total IRS plunged with 25 μg/mL of F1, while descended steadily with 5 μg/mL of F2. As palmitate increased the levels of Aβ40 and Aβ42, both AE subfractions were effective to reduce Aβ generation of and β-secretase activity, but IDE was not altered in any treatment conditions. The expression of DPP4 was also accompanied with insulin resistance signals. Inhibition of DPP4 attenuated the activity of β-secretase and production of Aβ. Moreover, the present data revealed that both AE subfractions significantly decrease the level of p-Tau.ConclusionsIn conclusion, we demonstrated that AE would be a potential adjuvant to prevent insulin resistance and the associated pathogenesis of AD, and F2 seems more feasible to be developed.

Identification of triterpenes and functional characterization of oxidosqualene cyclases involved in triterpene biosynthesis in lettuce (Lactuca sativa)

Lettuce (Lactuca sativa) is a member of the family Asteraceae and is most often used for green salads. Triterpenes are the largest class of natural compounds in plants and have beneficial health effects. Here, we identified various triterpene esters (taraxasterol acetates, ψ-taraxasterol acetates, taraxerol acetates, lupeol acetates, α-amyrin acetates, β-amyrin acetates, and germanicol acetate) and free triterpenes (α-amyrin, β-amyrin, taraxerol, and taraxasterol) in both the leaves and roots of lettuce. Triterpene biosynthesis occurs through the action of oxidosqualene cyclase (OSC), which generates various types of triterpenes from 2,3-oxidosqualene. None of the OSC genes involved in triterpene biosynthesis in lettuce have been characterized. Five putative lettuce OSC genes (LsOSC1, LsOSC2, LsOSC3, LsOSC4, and LsOSC5) were selected from a transcriptome database. These five genes were functionally characterized via heterologous expression in yeast. The first two enzymes were multifunctional triterpene synthase and the last three genes were monofunctional. Transgenic yeast expressing LsOSC1 produced five triterpenes, namely, taraxasterol, Ψ-taraxasterol, α-amyrin, β-amyrin, and dammarenediol-II. Yeast expressing LsOSC2 produced baurenol and Ψ-taraxasterol. LsOSC3, LsOSC4, and LsOSC5 expression led to β-amyrin, taraxerol, and lupeol production, respectively. Transcriptional activity assessment of the five genes revealed that all the OSC genes were more actively transcribed in roots than in leaves, and LsOSC5 among the five OSC genes showed the highest expression in both the leaves and the roots. In conclusion, we identified structurally diverse free triterpenes and triterpene esters in lettuce plants and characterized five OSC genes, which are key enzymes involved in the biosynthesis of diverse triterpenes in lettuce.

Agro Residues of Dendranthema x grandiflorum as Raw Material for a Potential Larvicidal Product

Residues of the chrysanthemum agroindustry from different cultivars of Dendranthema x grandiflorum are sold in the Vitoria (Espirito Santo State, Brazil) marketplaces. Because of the large of varieties of this hybrid species, this study aimed to confirm the chemical similarity of the residual material collected in one year at the commercial places in neighborhoods of the city (Vitoria) for using it as an homogenous raw material to prepare larvicidal products. Dichloromethane and methanol extracts were produced from 27 samples. Medium infrared (MIR) spectra were obtained in triplicate for the 54 extracts. MIR data were analyzed by principal components analysis (PCA), which divided the samples into two groups (GA1 and GA2) for dichloromethane extracts and into four groups (GB1, GB2, GB3 and GB4) for methanol extracts. The methanol extracts, we could see clear separation among the groups based on their classes of substances. The dichloromethane ones, it was possible to identify separation between GA1 and GA2 by classes of triterpene esters and diacylglycerols based on their mass peak intensities. Mixtures obtained from dichloromethane extracts (FA) and methanol extracts (FB) were assayed on Aedes aegypti larvae at the concentration 15 ppm. FB mixtures no larval mortality was observed, but FA mixtures were 100% active, possibly by the presence of fatty acids, triterpenes, steroids and alkamides in the samples of this group. These results show that residues of different varieties of the hybrid Dendranthema x grandiflorum generate chemically similar extracts, particularly for the lipophilic ones (FA), which can be used as a homogeneous raw material to obtain biologically active products, notably larvicides products.

Abelmoschus esculentus subfractions attenuate beta amyloid-induced neuron apoptosis by regulating DPP-4 with improving insulin resistance signals.

The association of Alzheimer disease (AD) and Diabetes (DM) is less clear. Accumulation of beta amyloid (Aβ) and presence of hyperphosphorylated tau (p-tau) are hallmarks of AD, spreading in the region where insulin receptors are also found. Aβ exerts neuron toxicity, and could disturb insulin signaling of phosphatidylinositol 3-kinase (PI3K), glycogen synthase kinase (GSK)-3β and AMP-activated protein kinase (AMPK), but increase IRS-1-Ser307 phosphorylation which is viewed as insulin resistance marker. Previously we reported dipeptidyl peptidase-4 (DPP-4) mediate insulin resistance signals, and Abelmoschus esculentus (AE) subfractions F1 (rich in quercetin glucosides and triterpene ester) and F2 (containing large amount of polysaccharides) attenuate DPP-4-mediated apoptosis. In the present study, we aim to investigate if Aβ induce neuron death by regulating DPP-4 and insulin resistance signals, and the putative effect of F1 and F2. By MTT, microscopy, and Western blotting, we demonstrate treatment of appropriate doses of AE subfractions prevent Aβ-induced neuron apoptosis. F1 attenuate Aβ-induced caspase 3 expression especially at 25 μg/mL, while F2 attenuate caspase 3 activation even at the low dose of 1 μg/mL. Both AE subfractions decrease Aβ-enhanced DPP-4, but increase Aβ-reduced p-AMPK and p-PI3K. The activity analysis reveals that F2 is more valid than F1 to reduce DPP-4 activity. The inhibition of DPP-4 demonstrates it plays the pivotal role in Aβ-induced neuron apoptosis. Moreover, although both F1 and F2 are effective to inhibit p-IRS-1-Ser307, F2 takes advantage to reduce p-Tau while F1 is superior to enhance p-GSK-3β. This implies AE subfractions act on different targets, and could be developed respectively. In conclusion, we demonstrate AE is potential to prevent Aβ-induced neuron damage by regulating DPP-4 and the insulin resistance cascades. AE could be an adjuvant to protect neuron degenerative disease related to Aβ and insulin resistance.

Toxicity, cytotoxicity and biological activities of seeds of &lt;i&gt;Carapa procera&lt;/i&gt; (DC), a native oil tree

Carapa procera is a native tree which seeds are intensively used for oil extraction. So this study deals with the identification of secondary metabolites, the toxicity and cytotoxicity of C. procera hydroalcohol extracts and their estrogenic and androgenic activities. The chemical constituents of C. procera extracts were determined by Thin Layer Chromatography (TLC) methods. The toxicity and cytotoxicity were respectively evaluated by the OECD Guideline 425 “Up and Down procedure” (UDP) and the brine shrimp lethality test. Estrogenic and androgenic activities were evaluated by uterotrophic and Hershberger tests and also by in vitro tests, with the yeast assay and MVLN luceferase assay. The MeOH/H 2 O extracts of C. procera seeds revealed the presence of steroidal glycosides, triterpene, flavonoids and polyphenols. The DCM fraction revealed the presence of triterpene esters & steroid and carotenoids. The MeOH/H 2 O has, by in vivo tests, slight toxic effects with mice and shows a lethal effect against the crustacean larvae by in vitro test. The extracts of C. procera seeds also show, by in vivo and in vitro tests an estrogenic and anti-androgenic activities. The results show with the presence of flavonoids, polyphenols and glycosides steroids estrogenic and anti-androgenic activities. The seeds of C. procera contain some phytochemicals, which can disrupt or reinforce endocrine function. Keywords : Carapa procera , native oil tree, seeds, toxicity, estrogenic, antiandrogenic

Optimization and validation of extraction and quantification methods of antimalarial triterpenic esters in Keetia leucantha plant and plasma

The aim of this study is to develop validated methods for the extraction and quantification of antimalarial triterpene esters from Keetia leucantha and from plasma samples. These compounds, showing in vitro and in vivo antiplasmodial activities, were optimally extracted from Keetia leucantha twigs using ultrasounds with dichloromethane and from plasma using protein precipitation with acetonitrile. We then developed and validated HPLC-UV quantification methods, which proved to be selective, accurate, linear, true and precise, both in plant and plasma samples for the eight triterpenic esters in mixture. Based on the total error concept as decision criteria, the validated dosage ranges of the triterpene esters mixture were set between 14.68 and 73.37 μg/mL in plants and 15.90 and 106.01 μg/mL in plasma injected solutions, corresponding to 7.95 and 53.01 μg/mL in plasma. These reliable methods were used to determine effectively triterpene esters content in collected samples, that seems highly variable in plant extracts, and will be helpful to further investigate pharmacokinetics parameters of these interesting bioactive compounds.

Differential Partitioning of Triterpenes and Triterpene Esters in Apple Peel.

Apple peel is a rich source of secondary metabolites, and several studies have outlined the dietary health benefits of ursane-type triterpenes in apple. Changes in triterpene metabolism have also been associated with the development of superficial scald, a postharvest apple peel browning disorder, and postharvest applications of diphenylamine and 1-methylcyclopropene. Previously, studies have generated metabolite profiles for whole apple peel or apple wax. In this study, we report separate metabolic analyses of isolated wax fractions and peel epidermis to investigate the spatial distribution of secondary metabolites in peel. In addition to examining previously reported triterpenes, we identified several unreported fatty acid esters of ursane-type triterpenes (C14-C22). All free pentacyclic triterpenes and triterpenic acids, with the exception of β-amyrin, were localized in the wax layer, along with esters of ursolic acid and uvaol. All sterols, sterol derivatives and α-amyrin esters were localized in the dewaxed peel epidermis.