Seeking faster, alternative methods for glycolipid biosurfactant characterization and purification.

Biosurfactants have been investigated as potential alternatives for synthetic surfactants in several areas, for example, in environmental and pharmaceutical fields. In that regard, extensive research has been carried out with sophorolipids and rhamnolipids that also present various biological properties with therapeutic significance. These biosurfactants are obtained as complex mixtures of slightly different molecules, and thus when studying these microbial glycolipids, the ability to identify and purify the produced compounds is of extreme importance. This study aimed to develop improved methodologies for the identification, separation, and purification of sophorolipids and rhamnolipids. Therefore, an ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method was modified to ensure faster characterization of both sophorolipids and rhamnolipids, enabling the identification and fragmentation pattern description of 10 and 13 congeners, respectively. The separation and purification of these biosurfactants was achieved with novel reversed-phase solid-phase extraction methods guaranteeing the isolation of different glycolipids, including those considered for their significant biological activity (e.g. antimicrobial, anticancer). It was possible to isolate sophorolipids and rhamnolipids with purity of 94% and 99%, respectively. The methods presented herein can be easily implemented and are expected to make purification of these biosurfactants easier, facilitating the study of their individual properties in further works.

Exploring the potential of chitosan-based particles as delivery-carriers for promising antimicrobial glycolipid biosurfactants.

Driven by the need to find alternatives to control Staphylococcus aureus infections, this work describes the development of chitosan-based particulate systems as carriers for antimicrobial glycolipids. By using a simple ionic gelation method stable nanoparticles were obtained showing an encapsulation efficiency of 41.1 ± 8.8 % and 74.2 ± 1.3 % and an average size of 210.0 ± 15.7 nm and 329.6 ± 8.0 nm for sophorolipids and rhamnolipids chitosan-nanoparticles, respectively. Glycolipids incorporation and particle size was correspondingly corroborated by FTIR-ATR and TEM analysis. Rhamnolipids chitosan nanoparticles (RLs-CSp) presented the highest antimicrobial effect towards S. aureus (ATCC 25923) exhibiting a minimal inhibitory concentration of 130 µg/mL and a biofilm inhibition ability of 99 %. Additionally, RLs-CSp did not interfere with human dermal fibroblasts (AG22719) viability and proliferation under the tested conditions. The results revealed that the RLs-CSp were able to inhibit bacterial growth showing adequate cytocompatibility and might become, after additional studies, a valuable approach to prevent S. aureus related infections.

Oleamide in Ipomoea and Dillenia Species and Inflammatory Activity Investigated through Ion Channel Inhibition.

BACKGROUND: Oleamide is an essential substance for human health. So, the plants with high oleamide content are great sources for health care products. OBJECTIVE: This study is conducted to investigate the quality of oleamide in plants and test the bioactivity in the selected two studied species. METHODS: The three Ipomoea and five Dillenia species including Ipomoea alba, Ipomoea aquatica and Ipomoea pes-caprae, and Dillenia indica, Dillenia obovata, Dillenia ovata, Dillenia parviflora and Dillenia pentagyna were investigated for the quantity of oleamide by high-performance liquid chromatography. The biological activity test was conducted on the powder formulation of the chosen plants, Dillenia ovata and Dillenia parviflora at a ratio of 30:70, for anti-inflammatory activity ex vivo on a panel of molecular targets through ion channel inhibition including voltage-gated sodium channel, voltage-gated potassium channel, and the cardiac ion as human ether-a-go-go related gene. RESULTS: The results showed that the leaf extracts of I. aquatica and D. ovata gave the highest and subsequent oleamide quantity i.e. 7.52 and 5.17 mg/g, respectively. Out of the Dillenia formulation which contained various compounds, oleamide showed the highest percentages of inhibition at 8.0-20.0%, and 6.2-14.2% in voltage-gated sodium channel, and voltage-gated potassium channel which had slightly lower values than the oleamide standard, and no effect as 0.0% value inhibition in the cardiac ion channel. CONCLUSION: The Dillenia formulation exhibits anti-inflammatory activity without affecting the heart. Accordingly, the three studied Ipomoea and three studied Dillenia species may be used for the same activity as a single component or formulation with effective solvent for disease treatments.

Direct Observation of Sophorolipid Micelle Docking in Model Membranes and Cells by Single Particle Studies Reveals Optimal Fusion Conditions.

Sophorolipids (SLs) are naturally produced glycolipids that acts as drug delivery for a spectrum of biomedical applications, including as an antibacterial antifungal and anticancer agent, where they induce apoptosis selectively in cancerous cells. Despite their utility, the mechanisms underlying their membrane interactions, and consequently cell entry, remains unknown. Here, we combined a single liposome assay to observe directly and quantify the kinetics of interaction of SL micelles with model membrane systems, and single particle studies on live cells to record their interaction with cell membranes and their cytotoxicity. Our single particle readouts revealed several repetitive docking events on individual liposomes and quantified how pH and membrane charges, which are known to vary in cancer cells, affect the docking of SL micelles on model membranes. Docking of sophorolipids micelles was found to be optimal at pH 6.5 and for membranes with -5% negatively charge lipids. Single particle studies on mammalian cells reveled a two-fold increased interaction on Hela cells as compared to HEK-293 cells. This is in line with our cell viability readouts recording an approximate two-fold increased cytotoxicity by SLs interactions for Hela cells as compared to HEK-293 cells. The combined in vitro and cell assays thus support the increased cytotoxicity of SLs on cancer cells to originate from optimal charge and pH interactions between membranes and SL assemblies. We anticipate studies combining quantitative single particle studies on model membranes and live cell may reveal hitherto unknown molecular insights on the interactions of sophorolipid and additional nanocarriers mechanism.

Evaluation of Antioxidant and Antibacterial Activities, Cytotoxicity of Acacia seyal Del Bark Extracts and Isolated Compounds.

Water extract of Acacia seyal bark is used traditionally by the population in Djibouti for its anti-infectious activity. The evaluation of in vitro antibacterial, antioxidant activities and cytotoxicity as well as chemical characterization of Acacia seyal bark water and methanolic extracts were presented. The water extract has a toxicity against the MRC-5 cells at 256 µg/mL while the methanolic extract has a weak toxicity at the same concentration. The methanolic extract has a strong antioxidant activity with half maximal inhibitory concentration (IC50) of 150 ± 2.2 µg/mL using 1-diphenyl-2-picrylhydrazyl (DPPH) and IC50 of 27 ± 1.3 µg/mL using 2,2'-azino-bis 3-ethylbenzthiazoline-6-sulphonic acid (ABTS) radical methods. For ferric reducing/antioxidant power (FRAP) assay, the result is 45.74 ± 5.96 µg Vitamin C Equivalent (VCE)/g of dry weight (DW). The precipitation of tannins from methanol crude extract decreases the MIC from 64 µg/mL to 32 µg/mL against Staphylococcus aureus and Corynebacterium urealyticum. However, the antioxidant activity is higher before tannins precipitation than after (IC50 = 150 µg/mL for methanolic crude extract and 250 µg/mL after tannins precipitation determined by DPPH method). By matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analysis, the results showed that the condensed tannins consist of two types of catechin and gallocatechin-based oligomers. The fractionation led to the identification of three pure compounds: two flavanols catechin and epicatechin; one triterpene as lupeol; and a mixture of three steroids and one fatty acid: campesterol, stigmasterol, clionasterol, and oleamide.

Oral shea nut oil triterpene concentrate supplement ameliorates pain and histological assessment of articular cartilage deterioration in an ACLT injured rat knee osteoarthritis model.

Osteoarthritis (OA) is a multifactorial joint disease and a common disabling condition in the elderly population. The associated pain and pathohistological changes in cartilage are common features of OA in both humans and animal models. Shea nut oil extract (SheaFlex75) contains a high triterpenoid concentration and has demonstrated anti-inflammatory and antiarthritic effects in both human and animal studies. In this study, we aim to investigate the potential of SheaFlex75 to prevent articular cartilage deterioration in a rat model of chronic OA progression. By employing anterior cruciate ligament transection (ACLT) with medial meniscectomy (MMx)-induced OA, we found attenuation of both early and chronic onset OA pain and cartilage degeneration in ACLT+MMx rats receiving SheaFlex75 dietary supplementation. Under long-term oral administration, the rats with induced OA presented sustained protection of both pain and OA cartilage integrity compared to the OA-control rats. Moreover, rats subjected to long-term SheaFlex75 ingestion showed normal biochemical profiles (AST, BUN and total cholesterol) and presented relatively lower triglycerides (TGs) and body weights than the OA-control rats, which suggested the safety of prolonged use of this oil extract. Based on the present evidence, preventive management is advised to delay/prevent onset and progression in OA patients. Therefore, we suggest that SheaFlex75 may be an effective management strategy for symptom relief and cartilage protection in patients with both acute and chronic OA.

A novel microbial technique for producing high-quality sophorolipids from horse oil suitable for cosmetic applications.

Horse oil contains linoleic, palmitoleic and unsaturated fatty acids that are similar to those in human skin, and may therefore be an ideal substance from which to isolate biosurfactants for cosmetic products to improve human skin quality. Herein, an innovative approach was developed to synthesise sophorolipids from horse oil by hydrolysis, followed by fermentation using the yeast Candida bombicola. The yield of sophorolipids from direct fermentation of horse oil and hydrolysed horse oil was 40.6 ± 1.3 g l-1 and 58.4 ± 1.8 g l-1 respectively. To further increase the yield, 30-40 g l-1 glucose was added in a fed-batch fermentation process to maintain the pH between 4.0 and 4.5, resulting in a conversion yield of 71.7 ± 0.8 g l-1 . The purity and structure of the synthesised sophorolipids were analysed by ultra-performance liquid chromatography-mass spectrometry and nuclear magnetic resonance. An in vitro human dermal fibroblast model was used as a surrogate for human skin to measure elastase inhibition activity. Antiwrinkle properties of isolated sophorolipids were better than those of horse oil or hydrolysed horse oil in several in vitro assays. Furthermore, no cytotoxicity was observed at a concentration of 50 µg ml-1 , and wound-healing capacity was evident in a cell culture model. Additionally, the synthesised sophorolipids attenuated lipopolysaccharide-induced expression of inflammatory cytokines in macrophages, and efficiently inhibited several strains of bacteria and yeast. In conclusion, fed-batch fermentation of hydrolysed horse oil is a novel and efficient approach for producing high-quality and high-yield sophorolipids that exhibit great potential as cosmetic ingredients.

The Effect of Solvent Type and Roasting Processes on Physico-Chemical Properties of Tigernut (Cyperus esculentus L.) Tuber Oil.

In this study, physico-chemical properties of raw and roasted tigernut oils extracted by two different solvents were determined. Peroxide values of raw and roasted tigernut oils extracted by petroleum ether and n-hexane solvents changed between 0.83 and 0.91 meqO2/100g to 1.57 and 1.63 meqO2/100g, respectively. While oleic acid contents of raw tigernut oils extracted by petroleum ether and n-hexane are determined as 66.83 and 67.47%, oleic acid contents of roasted tigernut oils extracted by petroleum ether and n-hexane were determined as 67.08 and 68.16%, respectively. The highest δ-tocopherol content was found in raw tigernut oil extracted by petroleum ether (54.91 mg/100g), while the lowest level is determined in roasted tigernut oil by n-hexane (50.77 mg/100g). As a result, the fatty acid profiles of roasted tigernut oil extracted by n-hexane were higher compared to results of raw tigernut oils extracted by petroleum ether (p < 0.05).

Multi-objective Optimization of Molecular Distillation Conditions for Oleic Acid from a Rich-in-Fatty Acid Model Mixture.

Oleic acid is a commercially valuable compound and has many positive health effects. Determining optimum conditions in a physical separation process is an industrially significant point due to environmental and health related concerns. Molecular distillation avoids the use of chemicals and adverse effects of high temperature application. The objective of this study was to determine the molecular distillation conditions for oleic acid to increase its purity and distillation yield in a model fatty acid mixture. For this purpose, a short-path evaporator column was used. Evaporation temperature ranged from 110 to 190℃, while absolute pressure was from 0.05 to 5 mmHg. Results showed that elevating temperature generally increased distillation yield until a maximum evaporation temperature. Vacuum application also affected the yield at a given temperature, and amount of distillate increased at higher vacuums except the case applied at 190℃. A multi-objective optimization procedure was then used for maximizing both yield and oleic acid amounts in distillate simultaneously, and an optimum point of 177.36℃ and 0.051 mmHg was determined for this purpose. Results also demonstrated that evaporation of oleic acid was also suppressed by a secondary dominant fatty acid of olive oil - palmitic acid, which tended to evaporate easier than oleic acid at lower evaporation temperatures, and increasing temperature achieved to transfer more oleic acid to distillate. At 110℃ and 0.05 mmHg, oleic and palmitic acid concentrations in distillate were 63.67% and 24.32%, respectively. Outcomes of this study are expected to be useful for industrial process conditions.

Fast Biodegradation of Diesel Hydrocarbons at High Concentration by the Sophorolipid-Producing Yeast Candida catenulata KP324968.

In the last decades, biodegradation as an environmentally friendly approach has raised interest in connection with the removal of hydrocarbon pollutants. Its capacity for removing pollutants strongly depends on the type of living cell and environmental conditions. The degradative activity of a new sophorolipid-producing yeast, Candida catenulata KP324968, in the removal of high concentrations of diesel from effluents was statistically evaluated considering the initial pH, the agitation speed, and the initial diesel concentration. The optimal setting of the operational variables at an initial pH of 4.7, an agitation speed of 204 rpm, and an initial diesel concentration of 93.4 g L-1 resulted in the highest total petroleum hydrocarbon removal efficiency: about 82.1% after 6 days (biodegradation rate: 0.378 g gcell-1 h-1). During the cell growth phase, the emulsification index in the medium increased and reached its highest level at 64.6% after 48 h. Further tests indicated that the emulsification capacity was obtained by in situ production of two sophorolipid molecules with an m/z of 533 and 583. In summary, its effective diesel removal and high emulsification capacity makes C. catenulata KP324968 an attractive candidate yeast for the degradation of hydrocarbons from aqueous environments.

Antiallergic Activity of Ethanol Extracts of Arctium lappa L. Undried Roots and Its Active Compound, Oleamide, in Regulating FcεRI-Mediated and MAPK Signaling in RBL-2H3 Cells.

The antiallergic potential of Arctium lappa L. was investigated in Sprague-Dawley rats, ICR mice, and RBL-2H3 cells. Ethanol extract (90%) of A. lappa (ALE, 100 µg/mL) inhibited the degranulation rate by 52.9%, determined by the level of ß-hexosaminidase. ALE suppressed passive cutaneous anaphylaxis (PCA) in rats and attenuated anaphylaxis and histamine release in mice. To identify the active compound of ALE, we subsequently fractionated and determined the level of ß-hexosaminidase in all subfractions. Oleamide was identified as an active compound of ALE, which attenuated the secretion of histamine and the production of tumor necrosis factor (TNF)-α and interleukin-4 (IL-4) in cells treated with compound 48/80 or A23187/phorbol myristate acetate (PMA). Oleamide suppressed FcεRI-tyrosine kinase Lyn-mediated pathway, c-Jun N-terminal kinases (JNK/SAPK), and p38 mitogen-activated protein kinases (p38-MAPKs). These results showed that ALE and oleamide attenuated allergic reactions and should serve as a platform to search for compounds with antiallergic activity.

Two new peroxy fatty acids with antibacterial activity from Ophioglossum thermale Kom.

Two new peroxy fatty acids, thermalic acids A (1) and B (2), together with eight known compounds, (3ß)-methyl-3-hydroxy-urs-11-en-28 oate (3), luteolin (4), quercetin (5), 3-methoxyquercetin (6), ophioglonol (7), ophioglonol 4'-O-α-D-glucopyranoside (8), pedunculosumoside B (9), syringol (10), were isolated from the herba of Ophioglossum thermale Kom. The structures of 1 and 2 were identified by HRESIMS, EIMS, 1D and 2D NMR, and electronic circular dichroism (ECD) spectra. Both two acids exhibited potential antibacterial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli. This is the first report of peroxy fatty acids isolated from herbaceous plants of Ophioglossaceae.

Structure and Potential Cellular Targets of HAMLET-like Anti-Cancer Compounds made from Milk Components.

The HAMLET family of compounds (Human Alpha-lactalbumin Made Lethal to Tumours) was discovered during studies on the properties of human milk, and is a class of protein-lipid complexes having broad spectrum anti-cancer, and some specific anti-bacterial properties. The structure of HAMLET-like compounds consists of an aggregation of partially unfolded protein making up the majority of the compound's mass, with fatty acid molecules bound in the hydrophobic core. This is a novel protein-lipid structure and has only recently been derived by small-angle X-ray scattering analysis. The structure is the basis of a novel cytotoxicity mechanism responsible for anti-cancer activity to all of the around 50 different cancer cell types for which the HAMLET family has been trialled. Multiple cytotoxic mechanisms have been hypothesised for the HAMLET-like compounds, but it is not yet clear which of those are the initiating cytotoxic mechanism(s) and which are subsequent activities triggered by the initiating mechanism(s). In addition to the studies into the structure of these compounds, this review presents the state of knowledge of the anti-cancer aspects of HAMLET-like compounds, the HAMLET-induced cytotoxic activities to cancer and non-cancer cells, and the several prospective cell membrane and intracellular targets of the HAMLET family. The emerging picture is that HAMLET-like compounds initiate their cytotoxic effects on what may be a cancer-specific target in the cell membrane that has yet to be identified. This article is open to POST-PUBLICATION REVIEW. Registered readers (see "For Readers") may comment by clicking on ABSTRACT on the issue's contents page.

Chiral phase-HPLC separation of hydroperoxyoctadecenoic acids and their biosynthesis by fatty acid dioxygenases.

Fatty acid oxygenases are often characterized by steric analysis of their hydroxy or hydroperoxy metabolites. Chiral phase-HPLC (CP-HPLC) can be used to separate enantiomeric hydroperoxyoctadecenoic acids. This method is based on analysis of seven octadecenoic fatty acids with double bonds at positions 6Z to 13Z, which were oxidized to hydroperoxides by photooxidation. A stationary phase, Reprosil Chiral NR, was found to resolve these hydroperoxy fatty acids with 1-hydroperoxy-2-propene and with 3-hydroperoxy-1-propene elements so that the S hydroperoxy fatty acids consistently eluted before the R stereoisomers. The chiral selector has not been disclosed, but it is described as an aromatic chiral phase with π-donor and π-acceptor groups of Pirkle type. The MS(3) spectra of the hydroperoxides showed characteristic fragments, which were influenced by the distance between the hydroperoxy and the carboxyl groups and the relative position of the double bond. Octadecenoic fatty acids can be oxidized by fungal and bacterial dioxygenases to hydroperoxides with cis or trans double bond configuration. Steric analysis of the hydroperoxy metabolites can be performed by this method, and it can also be used for preparative purposes.

Androgenic effect of honeybee drone milk in castrated rats: roles of methyl palmitate and methyl oleate.

ETHNOPHARMACOLOGICAL RELEVANCE: Numerous honeybee (Apis mellifera) products have been used in traditional medicine to treat infertility and to increase vitality in both men and women. Drone milk (DM) is a relatively little-known honeybee product with a putative sexual hormone effect. The oestrogenic effect of a fraction of DM has recently been reported in rats. However, no information is available on the androgenic effects of DM. The purpose of the present study was to determine the androgen-like effect of DM in male rats and to identify effective compounds. MATERIALS AND METHODS: A modified Hershberger assay was used to investigate the androgenic effect of crude DM, and the plasma level of testosterone was measured. The prostatic mRNA and protein expression of Spot14-like androgen-inducible protein (SLAP) were also examined with real-time PCR and Western blot techniques. GC-MS and NMR spectroscopic investigations were performed to identify the active components gained by bioactivity-guided fractionation. RESULTS: The crude DM increased the relative weights of the androgen-dependent organs and the plasma testosterone level in castrated rats and these actions were flutamide-sensitive. DM increased the tissue mRNA and protein level of SLAP, providing further evidence of its androgen-like character. After bioactivity-guided fractionation, two fatty acid esters, methyl palmitate (MP) and methyl oleate (MO), were identified as active compounds. MP alone showed an androgenic effect, whereas MO increased the weight of androgen-sensitive tissues and the plasma testosterone level only in combination. CONCLUSION: The experimental data of DM and its active compounds (MO and MP) show androgenic activity confirming the traditional usage of DM. DM or MP or/and MO treatments may project a natural mode for the therapy of male infertility.

Isolation and identification of new phytoconstituents from the fruit extract of Amomum subulatum Roxb.

The fruits of Amomum subulatum Roxb. (Zingiberaceae) (large cardamom), cultivated in the northern Himalayas, are used to treat stomach disorders, pulmonary diseases and liver complaints. Phytochemical investigation of the fruits led to the isolation of four new chemical compounds characterised as geranil-3(10)-en-9-olyl octadec-9-enoate, geranil-3(10)-en-9-carboxyl-ß-D-arabinopyranoside, geranilan-9-carboxy-α-L-arabinopyranoside and stigmast-5-en-3ß-ol-3ß-D-arabinopyranosyl-2'-(3″-methoxy) benzoate-3'-octadec-9‴,12‴,15‴-trienoate, along with the known compounds oleodilinolein and glyceryl trilinoleniate on the basis of spectral data analysis.

Antifungal lipids produced by lactobacilli and their structural identification by normal phase LC/atmospheric pressure photoionization−MS/MS.

Lactobacillus hammesii converts linoleic acid into an antifungal hydroxy fatty acid. High speed counter-current chromatography (HSCCC) using a hexane/ethyl acetate/methanol/water solvent system [3.5:1.5:3:2 (v/v/v/v)] allowed isolation of the antifungal hydroxy fatty acid. A method was developed for characterization of antifungal hydroxy fatty acids using normal phase liquid chromatography combined with atmospheric pressure photoionization-tandem mass spectrometry (LC/APPI-MS/MS). The position of unsaturations and hydroxyl groups was determined directly from crude lipid extracts and their hydroxylated derivatives. The antifungal compounds were identified as a racemic mixture of 10-hydroxy-cis-12-octadecenoic and 10-hydroxy-trans-12-octadecenoic acid. Additionally, HSCCC and LC/APPI-MS/MS methods were used to elucidate the pathway of conversion of linoleic acid by Lactobacillus sanfranciscensis , Lactobacillus plantarum , and L. hammesii to hydroxy fatty acids and conjugated linoleic acid. This study links previously reported 10-hydroxy-12-octadecenoic acid producing Lactobacillus strains to antifungal activities.

Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: a mechanistic and 3-D structure-activity study.

Plant-derived non-essential fatty acids are important dietary nutrients, and some are purported to have chemopreventive properties against various cancers, including that of the prostate. In this study, we determined the ability of seven dietary C-18 fatty acids to cause cytotoxicity and induce apoptosis in various types of human prostate cancer cells. These fatty acids included jacaric and punicic acid found in jacaranda and pomegranate seed oil, respectively, three octadecatrienoic geometric isomers (alpha- and beta-calendic and catalpic acid) and two mono-unsaturated C-18 fatty acids (trans- and cis-vaccenic acid). Jacaric acid and four of its octadecatrienoic geoisomers selectively induced apoptosis in hormone-dependent (LNCaP) and -independent (PC-3) human prostate cancer cells, whilst not affecting the viability of normal human prostate epithelial cells (RWPE-1). Jacaric acid induced concentration- and time-depedent LNCaP cell death through activation of intrinsic and extrinsic apoptotic pathways resulting in cleavage of PARP-1, modulation of pro- and antiapoptotic Bcl-2 family of proteins and increased cleavage of caspase-3, -8 and -9. Moreover, activation of a cell death-inducing signalling cascade involving death receptor 5 was observed. Jacaric acid induced apoptosis in PC-3 cells by activation of the intrinsic pathway only. The spatial conformation cis, trans, cis of jacaric and punicic acid was shown to play a key role in the increased potency and efficacy of these two fatty acids in comparison to the five other C-18 fatty acids tested. Three-dimensional conformational analysis using the PubChem Database (http://pubchem.ncbi.nlm.nih.gov) showed that the cytotoxic potency of the C-18 fatty acids was related to their degree of conformational similarity to our cytotoxic reference compound, punicic acid, based on optimized shape (ST) and feature (CT) similarity scores, with jacaric acid being most 'biosimilar' (ST(ST-opt)=0.81; CT(CT-opt)=0.45). This 3-D analysis of structural similarity enabled us to rank geoisomeric fatty acids according to cytotoxic potency, whereas a 2-D positional assessment of cis/trans structure did not. Our findings provide mechanistic evidence that nutrition-derived non-essential fatty acids have chemopreventive biological activities and Exhibit 3-D structure-activity relationships that could be exploited to develop new strategies for the prevention or treatment of prostate cancer regardless of hormone dependency.

Hydroxyl octadecenoic acids biosynthesized by crown galls of Panax quinquefolium induced by artermisinic acid.

OBJECTIVE: To investigate the effect of artermisinic acid on the secondary metabolites production of Panax quinquefolium crown galls. METHODS: Artemisinic acid was added into the suspended cells of Panax quinquefolium crown galls and co-culture for two days. Products were isolated with chromatographic method. RESULTS: Three hydroxyl octadecenoic acids [9,12,13-trihydroxy-10-octadecenoic acid (1), 11,12,13-trihydroxy-9-octadecenoic acid (2) and 11-hydroxy-12,13-epoxy-9-octadecenoic acid (3)] were isolated from crown galls of Panax quinquefolium. CONCLUSION: Artermisinic acid as one of the new type of phytohormones that might induce the production of 13-lipoxygenases in crown galls of Panax quinquefolium.

Evaluation of antimicrobial activity of extracts of Tibouchina candolleana (melastomataceae), isolated compounds and semi-synthetic derivatives against endodontic bacteria

This work describes the phytochemical study of the extracts from aerial parts of Tibouchina candolleana as well as the evaluation of the antimicrobial activity of extracts, isolated compounds, and semi-synthetic derivatives of ursolic acid against endodontic bacteria. HRGC analysis of the n-hexane extract of T. candolleana allowed identification of b-amyrin, a-amyrin, and b-sitosterol as major constituents. The triterpenes ursolic acid and oleanolic acid were isolated from the methylene chloride extract and identified. In addition, the flavonoids luteolin and genistein were isolated from the ethanol extract and identified. The antimicrobial activity was investigated via determination of the minimum inhibitory concentration (MIC) using the broth microdilution method. Amongst the isolated compounds, ursolic acid was the most effective against the selected endodontic bacteria. As for the semi-synthetic ursolic acid derivatives, only the methyl ester derivative potentiated the activity against Bacteroides fragilis.