Petroselinic acid

Peripheral serum metabolomic profiles inform central cognitive impairment.[Pubmed:32820198]

Sci Rep. 2020 Aug 20;10(1):14059.

The incidence of Alzheimer's disease (AD) increases with age and is becoming a significant cause of worldwide morbidity and mortality. However, the metabolic perturbation behind the onset of AD remains unclear. In this study, we performed metabolite profiling in both brain (n = 109) and matching serum samples (n = 566) to identify differentially expressed metabolites and metabolic pathways associated with neuropathology and cognitive performance and to identify individuals at high risk of developing cognitive impairment. The abundances of 6 metabolites, glycolithocholate (GLCA), Petroselinic acid, linoleic acid, myristic acid, palmitic acid, palmitoleic acid and the deoxycholate/cholate (DCA/CA) ratio, along with the dysregulation scores of 3 metabolic pathways, primary bile acid biosynthesis, fatty acid biosynthesis, and biosynthesis of unsaturated fatty acids showed significant differences across both brain and serum diagnostic groups (P-value < 0.05). Significant associations were observed between the levels of differential metabolites/pathways and cognitive performance, neurofibrillary tangles, and neuritic plaque burden. Metabolites abundances and personalized metabolic pathways scores were used to derive machine learning models, respectively, that could be used to differentiate cognitively impaired persons from those without cognitive impairment (median area under the receiver operating characteristic curve (AUC) = 0.772 for the metabolite level model; median AUC = 0.731 for the pathway level model). Utilizing these two models on the entire baseline control group, we identified those who experienced cognitive decline in the later years (AUC = 0.804, sensitivity = 0.722, specificity = 0.749 for the metabolite level model; AUC = 0.778, sensitivity = 0.633, specificity = 0.825 for the pathway level model) and demonstrated their pre-AD onset prediction potentials. Our study provides a proof-of-concept that it is possible to discriminate antecedent cognitive impairment in older adults before the onset of overt clinical symptoms using metabolomics. Our findings, if validated in future studies, could enable the earlier detection and intervention of cognitive impairment that may halt its progression.

[Extraction technology, composition analysis and antioxidant and antimicrobial activities of volatile oil from fenugreek leaves].[Pubmed:32726025]

Zhongguo Zhong Yao Za Zhi. 2020 Jul;45(13):3161-3168.

To define the extraction process, main components and antioxidative and antimicrobial activities of volatile oil from fenugreek(Trigonella foenum-graecum) leaves and its active substance basis. Response surface methodology was used for optimum supercritical CO_2 extraction conditions of essential oil from fenugreek leaves. The main components of volatile oil were analyzed by GC-MS, its antioxidant activity was evaluated by measuring the scavenging ability of 1,1-diphenyl-2-picrylhydrazyl(DPPH) and 2, 2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid, ABTS) free radical, and the antimicrobial effect of volatile oil was evaluated by K-B paper AGAR diffusion method. The results showed that the optimal extraction temperature was 50 , the extraction time was 89 min, and the extraction pressure was 35 MPa. Under the conditions, the optimum extracting yield of volatile oil was 1.72%,which was about 1.5 times higher than that of the conventional steam distillation. A total of 52 compounds were found based on reference substance retention time and GC-MS fragmentation information or the existing literatures, and the major compounds were oleic acid(9.65%), carveol(9.41%), n-hexadecanoic acid(9.1%), linoleic acid(6.95%), methyl linolenate(5.4%), Petroselinic acid(5.3%), testosterone(3.4%), sotolon(1.75%). The volatile oil of fenugreek showed moderate antioxidant activities in DPPH assay(IC_(50) value of 0.473 mg.mL~(-1)) and ABTS test(IC_(50) value of 0.107 mg.mL~(-1)). The oil had a stronger antimicrobial activity in vitro. MIC of the volatile oil ranged from 0.375 to 1.5 mg.mL~(-1). The results showed that the optimized volatile oil extraction process was stable, and the extraction yield was high. Fenugreek leaves contained a variety of volatile components, with obvious antioxidant and antibacterial activities. This study provides a certain theoretical basis for the comprehensive development and utilization of fenugreek.

Fatty acid composition and oil content during coriander fruit development.[Pubmed:32438233]

Food Chem. 2020 Oct 1;326:127034.

Coriander contains Petroselinic acid, an isomer fatty acid of oleic acid. Coriander seed oil has been proposed as novel food ingredient in the European Union. Field experiments were performed at Auch (France) during two seasons (2010 and 2011). From flowering to maturity, fruits were harvested weekly and oil content and fatty acid (FA) compositions were determined. Fruits presented 2% more oil in 2010 than in 2011. Petroselinic acid (PA) contents was higher in 2011 than in 2010. Oil accumulation began earlier after flowering (2 DAF) in 2011. A first step in accumulation was identified between two and 21 DAF characterized by high SFA and PUFA, which decreased 21 DAF. Subsequently, PA increased to its highest concentration (30-55 DAF) and SFA and PUFA reached their lowest. These results suggest that higher concentrations of PA can be achieved by collecting fruits before full maturity.

Transcriptome Analysis Reveals Candidate Genes for Petroselinic Acid Biosynthesis in Fruits of Coriandrum sativum L.[Pubmed:32320606]

J Agric Food Chem. 2020 May 13;68(19):5507-5520.

Petroselinic acid (18:1Delta(6)), a monounsaturated cis Delta-6 fatty acid, has many prospective applications in functional foods and for the nutraceutical and pharmaceutical industries. Up to 80% of Petroselinic acid has been found in the oil from fruits of coriander (Coriandrum sativum L.), which make it an ideal source for investigating the biosynthesis of Petroselinic acid. A coriander acyl-acyl carrier protein desaturase was identified to be involved in its biosynthesis more than two decades ago, but since then little further progress in this area has been reported. In this study, the fatty acid profiles of coriander fruits at six developmental stages were analyzed. Fruit samples from three developmental stages with rapid accumulation of Petroselinic acid were used for RNA sequencing using the Illumina Hiseq4000 platform. The transcriptome analysis presented 93323 nonredundant unigenes and 8545 differentially expressed genes. Functional annotation and combined gene expression data revealed candidate genes potentially involved in Petroselinic acid biosynthesis and its incorporation into triacylglycerols. Tissue-specific examination of q-PCR validation further suggested that ACPD1/3, KAS I-1, FATB-1/3, and DGAT2 may be highly involved. Bioinformatic analysis of CsFATB and CsDGAT2 identified their putative key amino acids or functional motifs. These results provide a molecular foundation for Petroselinic acid biosynthesis in coriander fruit and facilitate its genetic engineering in other hosts.

Lipid-Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.[Pubmed:31081279]

ChemSusChem. 2019 Aug 8;12(15):3642-3653.

Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and Petroselinic acid-based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram-negative and Gram-positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self-assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long-chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long-chained quaternary ammonium sophorolipids.

Optimization of ultrasound-assisted solvent extraction (UASE) based on oil yield, antioxidant activity and evaluation of fatty acid composition and thermal stability of Coriandrum sativum L. seed oil.[Pubmed:30956849]

Food Sci Biotechnol. 2018 Sep 17;28(2):377-386.

Ultrasound is one of emerging technique's which is being investigated extremely on food applications and extraction process. In this study, ultrasound-assisted solvent extraction was employed to extract vegetable oil from coriander (Coriandrum sativum L.) seeds. A response surface model was applied to determine the best condition of extraction concerning the independent factors (COY % and DPPH %). In addition, ultrasound variables were the sample solvent ratio, amplitude level, temperature and time. The best condition of extraction was obtained for sample solvent ratio of 1:13 (g/mL), amplitude level of 82 (%), temperature of 45 ( degrees C) and extraction time of 9 (min), being the maximum point of oil yield and antioxidant activity (30.74-72.05%), respectively. Fatty acid profile of oil has been shown as a rich source of Petroselinic acid (C18:1)-12, making up 76% of all fatty acids. TGA analyses revealed that 82% (by weight) of oil is thermally stable up to 224 degrees C.

Anti-borreliae efficacy of selected organic oils and fatty acids.[Pubmed:30717726]

BMC Complement Altern Med. 2019 Feb 4;19(1):40.

BACKGROUND: Borrelia sp. is a causative pathogen of Lyme disease which has become a worldwide health concern. Non-toxic approaches especially directed toward latent persistent forms of this pathogen are desired. Lipids in the form of volatile and non-volatile oils, and fatty acids with proven anti-borreliae efficacy could become an additional support or an alternative for consideration in treatment approaches. METHODS: In this study we investigated 47 lipids (30 volatile and non-volatile oils, and 17 fatty acids) of plant and animal origin against typical motile, knob/round-shaped persisters, and biofilm-like aggregates of Borrelia burgdorferi s.s. and Borrelia garinii, which are identified as pathogenic factors of Lyme disease in the USA and Europe, using direct microscopic counting and spectrofluorometric measurements. RESULTS: Out of all examined lipids, 5 oils (Bay leaf oil, Birch oil, Cassia oil, Chamomile oil German, and Thyme oil) at or below 0.25%, and 3 fatty acids (13Z,16Z Docosadienoic acid, erucic acid, and Petroselinic acid) at or below 0.75 mg/ml, showed bactericidal activity against typical motile spirochetes and knob/round-shaped persisters. Only Bay leaf oil and Cassia oil, including their major constituents, eugenol and cinnamaldehyde, showed to target biofilm-like aggregates of both tested Borrelia spp. at the same concentration, although with 20-30% eradication mark. CONCLUSION: Based on obtained results, volatile oils were more potent than non-volatile oils, and unsaturated fatty acids were more effective than saturated fatty acids. Among all tested oils, Bay leaf oil and Cassia oil, with their major components eugenol and cinnamaldehyde, seem to have the highest anti-borreliae efficacy.

Inhibition of quorum sensing-dependent biofilm and virulence genes expression in environmental pathogen Serratia marcescens by petroselinic acid.[Pubmed:29101490]

Antonie Van Leeuwenhoek. 2018 Apr;111(4):501-515.

The aim of this study was to evaluate the anti-biofilm and anti-virulence properties of Petroselinic acid (PSA) against the environmental pathogen Serratia marcescens. PSA significantly inhibited the quorum sensing (QS)-dependent virulence factors such as prodigiosin, protease productions, and biofilm formation in S. marcescens. The antibiofilm potential of PSA was also confirmed through light, confocal laser scanning, and scanning electron microscopic analyses. Furthermore, PSA effectively inhibited the biofilm-related phenomena such as exopolysaccharide production, hydrophobicity production, swimming, and swarming motility without affecting the bacterial growth. In FT-IR analysis, the PSA treated S. marcescens cells displayed a reduction in cellular components compared to the untreated controls. The real-time analysis revealed the downregulation of QS-controlled virulence genes such as bsmB, fimA, fimC, and flhD in S. marcescens on treatment with PSA. The obtained results strongly suggested that PSA could be further explored as an antipathogenic drug to treat QS-mediated infections caused by S. marcescens.

Fatty Acid Methyl Ester Composition of Some Turkish Apiaceae Seed Oils: New Sources for Petroselinic Acid.[Pubmed:30475510]

Nat Prod Commun. 2016 Nov;11(11):1697-1700.

The seed oils of twenty-six species of Apiaceae belonging to the genera Bunium, Cnidium, Ferula, Ferulago, Heracleum, Hippomarathrum, Malabaila, Myrrhoides, Olymposciadium, Pimpinella, Prangos, Szovitsia, Trigonasciadium, Trinia and Zosima, collected in Turkey, were investigated for their oil content, and amount of Petroselinic acid (PA), as well as for the composition of their fatty acid methyl esters (FAMEs) by GC-MS. Seed oil content ranged from 7.1% in Szovitsia callicarpa to 29.3% in Ferda haussknechtii. The results showed that the seed oils of the studied species contained high amounts of PA (1.2-72.2%), followed by significant amounts of linoleic (LA, 13.8-50.8%) and oleic (OA, 4.2-61.6%) acids. PA was found in all the analyzed species, except for Olymposciadium caespitosum, which belongs to a monotypic endemic genus of the family. According to data from our study, PA was found to be predominantly in the seed oils of Hippomarathrum cristatum (72.2%), Trinia glauca (64.9%) and Bunium microcarpum (59.7%) and, therefore these species might be considered as new sources of PA, and represent a potential oleochemical raw material. This is the first extensive study of the composition ofTurkish Apiaceae species. The high amounts of PA may also have chemotaxonomic significance.

Characterization of French Coriander Oil as Source of Petroselinic Acid.[Pubmed:27617992]

Molecules. 2016 Sep 8;21(9). pii: molecules21091202.

Coriander vegetable oil was extracted from fruits of French origin in a 23% yield. The oil was of good quality, with a low amount of free fatty acids (1.8%) and a concurrently high amount of triacylglycerols (98%). It is a rich source of Petroselinic acid (C18:1n-12), an important renewable building block, making up 73% of all fatty acids, with also significant amounts of linoleic acid (14%), oleic acid (6%), and palmitic acid (3%). The oil was characterized by a high unsaponifiable fraction, comprising a substantial amount of phytosterols (6.70 g/kg). The main sterol markers were beta-sitosterol (35% of total sterols), stigmasterol (24%), and Delta(7)-stigmastenol (18%). Squalene was detected at an amount of 0.2 g/kg. A considerable amount of tocols were identified (500 mg/kg) and consisted mainly of tocotrienols, with gamma-tocotrienol as the major compound. The phospholipid content was low at 0.3%, of which the main phospholipid classes were phosphatidic acid (33%), phosphatidylcholine (25%), phosphatidylinositol (17%), and phosphatidylethanolamine (17%). About 50% of all phospholipids were non-hydratable. The beta-carotene content was low at 10 mg/kg, while a significant amount of chlorophyll was detected at about 11 mg/kg. An iron content of 1.4 mg/kg was determined through element analysis of the vegetable oil. The influence of fruit origin on the vegetable oil composition was shown to be very important, particularly in terms of the phospholipids, sterols, and tocols composition.

Fatty acids and sterols composition, and antioxidant activity of oils extracted from plant seeds.[Pubmed:27451203]

Food Chem. 2016 Dec 15;213:450-456.

This study determined and compared the contents of bioactive components in plant seed oils extracted with n-hexane (Soxhlet method) and chloroform/methanol (Folch method) from coriander, caraway, anise, nutmeg and white mustard seeds. Oleic acid dominated among unsaturated fatty acids in nutmeg and anise seed oils while Petroselinic acid was present in coriander and caraway oils. Concerning sterols, beta-sitosterol was the main component in seed oils extracted with both methods. The content of total phenolics in nutmeg, white mustard and coriander seed oils extracted with chloroform/methanol was higher than in their counterparts prepared with n-hexane. The seed oil samples extracted according to the Folch method exhibited a higher ability to scavenge DPPH radicals compared to the oil samples prepared with the Soxhlet method. DPPH values of the methanolic extracts derived from oils produced with the Folch method were also higher than in the oils extracted with n-hexane.

Petroselinic acid purification and its use for the fermentation of new sophorolipids.[Pubmed:27033544]

AMB Express. 2016 Mar;6(1):28.

Petroselinic acid, a positional isomer of oleic acid, was isolated from the vegetable oil of Coriandrum sativum fruits. This uncommon fatty acid was subsequently used as substrate for sophorolipid fermentation with a Starmerella bombicola lactone esterase overexpression (oe sble) strain. A Petroselinic acid based diacetylated sophorolipid lactone was obtained in high purity without incorporation of de novo synthesized fatty acids such as oleic acid. A total production of 40 g/L was obtained. The Petroselinic acid based sophorolipid lactone was subsequently hydrolyzed towards the Petroselinic acid based sophorolipid acid. For both compounds, their critical micelle concentration (CMC) and corresponding surface tension were compared to their oleic acid based counterparts. Both Petroselinic acid based sophorolipids displayed a much lower CMC value than their oleic acid based counterparts, although their minimal surface tension was the same. Besides, the sophorolipid fermentation product was chemically modified towards a novel C12 sophorolipid aldehyde. This derivative constitutes an interesting building block for further modification towards new-to-nature sophorolipids with high potential for self-assembly applications.

Oil Content, Fatty Acid Composition and Distributions of Vitamin-E-Active Compounds of Some Fruit Seed Oils.[Pubmed:26785341]

Antioxidants (Basel). 2015 Jan 29;4(1):124-33.

Oil content, fatty acid composition and the distribution of vitamin-E-active compounds of selected Turkish seeds that are typically by-products of the food processing industries (linseed, apricot, pear, fennel, peanut, apple, cotton, quince and chufa), were determined. The oil content of the samples ranged from 16.9 to 53.4 g/100 g. The dominating fatty acids were oleic acid (apricot seed oil, peanut oil, and chufa seed oil) in the range of 52.5 to 68.4 g/100 g and linoleic acid (pear seed oil, apple seed oil, cottonseed oil and quince seed oil) with 48.1 to 56.3 g/100 g, while in linseed oil mainly alpha-linolenic acid (53.2 g/100 g) and in fennel seed oil mainly 18:1 fatty acids (80.5 g/100 g) with Petroselinic acid predominating. The total content of vitamin-E-active compounds ranged from 20.1 (fennel seed oil) to 96 mg/100 g (apple seed oil). The predominant isomers were established as alpha- and gamma-tocopherol.

Accurate Mass GC/LC-Quadrupole Time of Flight Mass Spectrometry Analysis of Fatty Acids and Triacylglycerols of Spicy Fruits from the Apiaceae Family.[Pubmed:26633337]

Molecules. 2015 Dec 2;20(12):21421-32.

The triacylglycerol (TAG) structure and the regio-stereospecific distribution of fatty acids (FA) of seed oils from most of the Apiaceae family are not well documented. The TAG structure ultimately determines the final physical properties of the oils and the position of FAs in the TAG molecule affects the digestion; absorption and metabolism; and physical and technological properties of TAGs. Fixed oils from the fruits of dill (Anethum graveolens), caraway (Carum carvi), cumin (Cuminum cyminum), coriander (Coriandrum sativum), anise (Pimpinella anisum), carrot (Daucus carota), celery (Apium graveolens), fennel (Foeniculum vulgare), and Khella (Ammi visnaga), all from the Apiaceae family, were extracted at room temperature in chloroform/methanol (2:1 v/v) using percolators. Crude lipids were fractionated by solid phase extraction to separate neutral triacylglycerols (TAGs) from other lipids components. Neutral TAGs were subjected to transesterification process to convert them to their corresponding fatty acids methyl esters (FAMES) using 1% boron trifluoride (BF(3)) in methanol. FAMES were analyzed by gas chromatography-quadrupole time of flight (GC-QTOF) mass spectrometry. Triglycerides were analyzed using high performance liquid chromatography-quadrupole time of flight (LC-QTOF) mass spectrometry. Petroselinic acid was the major fatty acid in all samples ranging from 57% of the total fatty acids in caraway up to 82% in fennel. All samples contained palmitic (16:0), palmitoleic (C16:1n-9), stearic (C18:0), petroselinic (C18:1n-12), linoleic (C18:2n-6), linolinic (18:3n-3), and arachidic (C20:0) acids. TAG were analyzed using LC-QTOF for accurate mass identification and mass spectrometry/mass spectrometry (MS/MS) techniques for regiospesific elucidation of the identified TAGs. Five major TAGs were detected in all samples but with different relative concentrations in all of the tested samples. Several other TAGs were detected as minor components and were present in some samples and absence in the others. Regiospecific analysis showed a non-random fatty acids distribution. Petroselinic acid was predominantly located at the sn-1 and sn-3 positions.

Fatty acid composition analysis in polysorbate 80 with high performance liquid chromatography coupled to charged aerosol detection.[Pubmed:25460583]

Eur J Pharm Biopharm. 2015 Aug;94:569-74.

The fatty acid (FA) composition of polysorbate 80 (PS80), a sorbitan oleic acid ester copolymerized with about 20mole of ethylene oxide, is typically characterized by gas chromatography. Here, an alternative method was developed. After saponification with potassium hydroxide the FA fraction was collected with liquid-liquid extraction using methyl-tert-butyl ether. HPLC in combination with a Corona(R) charged aerosol detector (CAD) was applied for the separation and detection. The method was fully validated in terms of specificity, repeatability, limits of quantification, linearity, range, accuracy and robustness. The characterization of 16 different PS80 batches demonstrated variability regarding their FA composition, with e.g. the amount of oleic acid ranging from 67.8+/-0.7% to 96.6+/-1.4%. Furthermore, we identified Petroselinic acid, a double-bond positional isomer to oleic acid in all batches, an FA not known to pharmacopoeias at present. In addition, 11-hydroxy-9-octadecenoic acid, an oxidation product of oleic acid was identified. Structure elucidation was performed by means of HPLC-MS/MS. In addition, the method was expanded to the evaluation of the free FAs. Having determined the entire FA composition, the acid value according to EP and USP can be calculated.