Ethyl oleateCAS# 111-62-6 |
2D Structure
Quality Control & MSDS
Package In Stock
Number of papers citing our products
Cas No. | 111-62-6 | SDF | Download SDF |
PubChem ID | N/A | Appearance | Powder |
Formula | C20H38O2 | M.Wt | 310.52 |
Type of Compound | Aliphatics | Storage | Desiccate at -20°C |
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Ethyl oleate Dilution Calculator
Ethyl oleate Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.2204 mL | 16.102 mL | 32.204 mL | 64.4081 mL | 80.5101 mL |
5 mM | 0.6441 mL | 3.2204 mL | 6.4408 mL | 12.8816 mL | 16.102 mL |
10 mM | 0.322 mL | 1.6102 mL | 3.2204 mL | 6.4408 mL | 8.051 mL |
50 mM | 0.0644 mL | 0.322 mL | 0.6441 mL | 1.2882 mL | 1.6102 mL |
100 mM | 0.0322 mL | 0.161 mL | 0.322 mL | 0.6441 mL | 0.8051 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- Methyl arachidonate
Catalog No.:BCX1381
CAS No.:2566-89-4
- Ethyl Arachidonate
Catalog No.:BCX1380
CAS No.:1808-26-0
- Arachidic acid
Catalog No.:BCX1379
CAS No.:506-30-9
- Palmitoleic acid
Catalog No.:BCX1378
CAS No.:373-49-9
- Ethyl palmitoleate
Catalog No.:BCX1377
CAS No.:56219-10-4
- Nonadecanoic acid
Catalog No.:BCX1376
CAS No.:646-30-0
- Methyl heptadecanoate
Catalog No.:BCX1375
CAS No.:1731-92-6
- Heptadecanoic acid
Catalog No.:BCX1374
CAS No.:506-12-7
- Pentadecanoic acid
Catalog No.:BCX1373
CAS No.:1002-84-2
- Methyl tridecanoate
Catalog No.:BCX1372
CAS No.:1731-88-0
- Tridecanoic acid
Catalog No.:BCX1371
CAS No.:638-53-9
- Octadec-11-enoic acid
Catalog No.:BCX1370
CAS No.:693-72-1
- Docosahexaenoic acid ethyl ester
Catalog No.:BCX1383
CAS No.:84494-72-4
- Docosahexaenoic acid methyl ester
Catalog No.:BCX1384
CAS No.:2566-90-7
- Eicosapentaenoic acid ethyl ester
Catalog No.:BCX1385
CAS No.:86227-47-6
- Methyl Eicosapentaenoate
Catalog No.:BCX1386
CAS No.:2734-47-6
- Linoleic acid sodium salt
Catalog No.:BCX1387
CAS No.:822-17-3
- γ-Linolenic acid
Catalog No.:BCX1388
CAS No.:506-26-3
- Arundoin
Catalog No.:BCX1389
CAS No.:4555-56-0
- Flaccidoside II
Catalog No.:BCX1390
CAS No.:140694-19-5
- Peruvoside
Catalog No.:BCX1391
CAS No.:1182-87-2
- Thevetin A
Catalog No.:BCX1392
CAS No.:37933-66-7
- 3-O-Acetylbufotalin
Catalog No.:BCX1393
CAS No.:4029-69-0
- Smilagenin
Catalog No.:BCX1394
CAS No.:126-18-1
Investigation on the insecticidal activities of cyanobacterial extracts as an alternative source for the management of fall armyworm, Spodoptera frugiperda (J. E. Smith) (Lepidoptera: Noctuidae).[Pubmed:38623187]
Heliyon. 2024 Apr 3;10(7):e29060.
The Spodoptera frugiperda is a notorious pest with a broad host range. It severely damages crops, mainly in areas of the globewhere maize and sorghum are grown. The pest is difficult to control due to its adaptive nature and resistance to several insecticides available in the market. So, an identification of the alternative strategy is the prime important in the present context. Insecticidal activities of cyanobacterial extracts were evaluated in the laboratory as a biocomponent against S. frugiperda. The crude extracts of Nostoc muscorum and Spirulina sp. were prepared by using ethanol, methanol and petroleum ether solvents. Soxhlet apparatus was used for extraction. S. frugiperda larvae in their second instar were given access to fragments of maize leaf that had been treated with various cyanobacterial extracts. The findings displayed that the petroleum ether extract of N. muscorum had the lowest LC50 value of 155.22 ppm, followed by petroleum ether extracts of Spirulina, ethanol extract of N. Muscorum, methanol extract of N. muscorum, ethanol and methanol extract of Spirulina with an LC(50) values of 456.02, 710, 780, 1050 and 1070 ppm respectively. Later, the effect of LC(50) values on many biological parameters like the larval duration and pupal stages, the percentage of pupation, the weight of the pupal stage, the malformation of the pupal and adult stages, adult emergence percentage, fertility and the longevity of the male and female adult stages of S. frugiperda was examined. The gas chromatography-mass spectrometry (GC-MS) was used to analyse the crude extract to identify the bioactive components that were responsible for the insecticidal properties. The major compounds detected were diethyl phthalate (19.87 %), tetradecane (5.03%), hexadecanoic acid, ethyl ester (4.10 %), dodecane (4.03%), octadecane (3.72%), octadecanoic acid, methyl ester (3.40 %), Ethyl oleate (3.11 %), methyl ester. octadecenoic acid (3.04 %), heptadecane (3.04 %) and phytol (3.02 %). The presence of several bioactive chemicals in the cyanobacterial extracts may be the reason for their insecticidal actions, thus it can be used as an alternative and new source to combat fall armyworm and other crop pests.
Lipolytic production from solid-state fermentation of the filamentous fungus Penicillium polonicum and its applicability as biocatalyst in the synthesis of ethyl oleate.[Pubmed:38558334]
Environ Sci Pollut Res Int. 2024 Apr;31(19):28632-28643.
Lipases represent versatile biocatalysts extensively employed in transesterification reactions for ester production. Ethyl oleate holds significance in biodiesel production, serving as a sustainable alternative to petroleum-derived diesel. In this study, our goal was to prospect lipase and assess its efficacy as a biocatalyst for Ethyl oleate synthesis. For quantitative analysis, a base medium supplemented with Rhodamine B, olive oil, and Tween 80 was used. Solid-state fermentation utilized crambe seeds of varying particle sizes and humidity levels as substrates. In the synthesis of Ethyl oleate, molar ratios of 1:3, 1:6, and 1:9, along with a total enzymatic activity of 60 U in n-heptane, were utilized at temperatures of 30 degrees C, 37 degrees C, and 44 degrees C. Reactions were conducted in a shaker at 200 rpm for 60 min. As a result, we first identified Penicillium polonicum and employed the method of solid-state fermentation using crambe seeds as a substrate to produce lipase. Our findings revealed heightened lipolytic activity (22.5 Ug(-1)) after 96 h of fermentation using crambe cake as the substrate. Optimal results were achieved with crambe seeds at a granulometry of 0.6 mm and a fermentation medium humidity of 60%. Additionally, electron microscopy suggested the immobilization of lipase in the substrate, enabling enzyme reuse for up to 4 cycles with 100% enzymatic activity. Subsequently, we conducted applicability tests of biocatalysts for Ethyl oleate synthesis, optimizing parameters such as the acid/alcohol molar ratio, temperature, and reaction time. We attained 100% conversion within 30 min at 37 degrees C, and our results indicated that the molar ratio proportion did not significantly influence the outcome. These findings provide a methodological alternative for the utilization of biocatalysts in Ethyl oleate synthesis.
Hexane extract of Persea schiedeana Ness as green corrosion inhibitor for the brass immersed in 0.5 M HCl.[Pubmed:38499625]
Sci Rep. 2024 Mar 18;14(1):6512.
The hexane extract of Persea schiedeana Ness (PSN) was analyzed as corrosion inhibitor for the brass surface immersed in 0.5 M HCl. Fourier-transform infrared spectroscopy and a gas chromatographic (GC) and mass spectrometric (MS) were used to identify the PSN extract's functional groups and compound constituents. The functional groups identified were CH3 and CH2 functional alkyl groups, C=O stretching vibration of aldehydes, ketones, and carbonyl groups. The GC/MS determined the presence of fatty acids in the PSN extract, where palmitic acid, oleic acid, and Ethyl oleate were the major constituents. Electrochemical characterizations were conducted to observe the effect of PSN as corrosion inhibitor on the brass surface. The R(p) and R(n) calculated from EIS and ENA give the same behavior. Based on the OCP behavior, it was determined that the PSN works as a mix inhibitor, affecting both anodic and cathodic reactions. The corrosion current density (I(corr)) suggests that the extract of PSN reduces the corrosion rate of the brass with efficiencies above 90% for all concentrations. The efficiency obtained for each PSN concentration was attributed to forming a corrosion scale of CuO and Cu2O , which reacted with the carboxyl group to form copper carboxylates on the metal surface.
Phytocompounds of Nigella sativa seeds extract and their neuroprotective potential via EGR1 receptor inhibition: A molecular docking study.[Pubmed:38454971]
Narra J. 2023 Aug;3(2):e173.
Bioactivity of Nigella sativa seed extract has the potential as a neuro-protector, offering its promising utility in the clinical setting for brain injury management. This study aimed to identify the phytocompounds contained in the extract of N. sativa seeds and further screen their respective neuronal anti-inflammatory activities in silico. The extract of N. sativa seeds was prepared through successive maceration using non-polar to polar solvents (n-hexane and ethanol, respectively). The phytocompounds in the ethanolic extract were initially identified through qualitative analysis and further analyzed with gas chromatography-mass spectrometry (GC-MS). The spectral data were compared with the compound library for identification. The identified phytocompounds were then simulated computationally for their binding affinities toward the active pocket of early growth response-1 (EGR1) receptor (PDB: 14r2a). We found that the ethanolic extract of N. sativa seeds were predominantly constituted of hexadecanoic acid, ethyl ester (17.15%); linoleic acid ethyl ester (15.0%); octadecanoic acid (13.26%); and Ethyl oleate (10.38%). The binding affinity of the phytocompounds ranged from -7.49 kcal/mol (methyl palmitoleate) to -14.31 kcal/mol (9-hexadecanoic acid, methyl ester), with 12 compounds having binding affinity < -10 kcal/mol. In conclusion, ethanolic extract of N. sativa seeds are rich with fatty acids that have active as anti-inflammatory and may exert neuronal protection by inhibiting EGR1 receptor. Studies using animal models to confirm the activity are warranted.
Nutritional, chemical and functional potential of Inga laurina (Fabaceae): A barely used edible species.[Pubmed:38309858]
Food Res Int. 2024 Feb;178:113751.
Inga laurina is a plant species which produces edible fruits, and until now there is little information available concerning its nutritional, chemical and bioactive composition. In this study, we evaluated for the first time the proximate composition and mineral contents in its fruit (peel, pulp and seed), that is the traditionally consumed part. The seeds obtained the highest protein (19.52 g/100 g), carbohydrate (22.5 g/100 g) and mineral contents, mainly Cu, Cr, P, Mn, Se and Zn. The peel and pulp were excellent sources of fiber (4.5 and 11.05 g/100 g) as well as mineral content, with Cr and Cu standing out in the pulp. This study is notably the first to provide a detailed assessment of the nutritional compositions of traditionally consumed and not consumed parts of this fruit. Sensory analysis of the pulp was also performed, which indicated good acceptance. The antioxidant properties were characterized in the fruit, peels and leaves. The ABTS test showed that leaf supernatant hydroethanolic crude extract (EC(50) = 2.70 mug/mL) and its corresponding ethyl acetate (EC(50) = 1.68 microg/mL) and butanol (EC(50) = 2.48 microg/mL) partitions presented higher antioxidant potential compared to the control Ginkgo biloba (EC(50) = 12.17 microg/mL). The most active precipitate extract regarding DPPH was from the peel (EC(50) = 13.30 mug /mL) and the most active partition was the ethyl acetate (EC(50) = 13.37 mug/mL), both with better activity compared to the control Ginkgo biloba (EC(50) = 46.97 mug/mL). The ethyl acetate partition (EC(50) = 13.45 mug/mL) and butanol partition (EC(50) = 7.97 mug/mL) from the leaves showed the highest antioxidant capacity. Thus, extracts and partitions from the peels and leaves were studied from a phytochemical point of view due to presenting the best results for antioxidant capacity. The presence of phenolic compounds such as myricetin-3-O-rhamnopyranoside, myricetin-3-O-(2''-O-galloyl)-rhamnopyranoside and myricetin-3-O-(2'',4''-di-O-galloyl)-arabinopentoside-methyl ether were observed in the leaf crude extract and polar partitions, being reported for the first time in the Inga genus and Fabaceae family. Moreover, quercetin, quercetin-3-O-galatoctoside, quercetin-3-O-rhamnopyranoside, quercetin-3-O-(2''-O-galloyl)-rhamnoside, and quercetin tri-hexose were identified in the peel crude extract and ethyl acetate partition, in which the galloyl derivative of quercetin was identified for the first time in I. laurina fruit peels. GC-MS enabled separating and identifying substances such as palmitic and stearic acids, and Ethyl oleate. It is possible to conclude that I. laurina pulp can be a supplementary food as a source of phenolic compounds, and the other organs of the plant (leaves and peel) are rich in flavonoids with great antioxidant capacity, making this species a promising source of antioxidants.
Solvent-free synthesis of hydrophobic and amphiphilic esters using a chemically modified lipase from Thermomyces lanuginosus: a comparative study with native and immobilized forms.[Pubmed:38169079]
Chembiochem. 2024 Feb 16;25(4):e202300843.
Using lipases to catalyze the synthesis of the most differentiated type of compounds remains one of the major challenges among scientists. Seeking more economic and advantageous catalysts is a current goal of green chemistry. In this work, we demonstrate the potential of a chemically modified form of lipase from Thermomyces lanuginosus (cmLTL) for the synthesis of both hydrophobic (heptyl heptanoate, heptyl octanoate, heptyl decanoate, decyl heptanoate, decyl octanoate and decyl decanoate) and amphiphilic (2-(2-ethoxyethoxy)Ethyl oleate and 2-(2-ethoxyethoxy)ethyl linoleate) esters, in bulk. The results were compared with its native (LTL) and immobilized (imLTL) forms. The data revealed that LTL showed poor activity for all reactions performed with n-heptane (eta<20 %). ImLTL was able to synthesize all hydrophobic esters (eta>60 %), with exception of the short ester, heptyl heptanoate. cmLTL was the only form of LTL capable of producing hydrophobic and amphiphilic esters, without compromising the yield when the reactions were performed under solvent-free conditions (>50 %). Molecular modeling showed that the active pocket of cmLTL is able to deeply internalize transcutol, with stronger interactions, justifying the outstanding results obtained. Furthermore, owing to the possibility of cmLTL filtration, the reusability of the catalyst is ensured for at least 6 cycles, without compromising the reaction yields.
New insights into changing honey bee (Apis mellifera) immunity molecules pattern and fatty acid esters, in responses to Ascosphaera apis infection.[Pubmed:38065241]
J Invertebr Pathol. 2024 Feb;202:108028.
Monitoring of metabolite changes could provide valuable insights into disturbances caused by an infection and furthermore, could be used to define the status of an organism as healthy or diseased and define what could be defensive elements against the infection. The present investigation conducted a gas chromatography-mass spectrometry (GC/MS) for haemolymph of larval honey bees (Apis mellifera L.) infected with the fungal pathogen Ascosphaera apis in comparison with control haemolymph non-infected insects. Results revealed that the pathogen caused a general disturbance of metabolites detected in the haemolymph of the honey bee. The majority of metabolites identified before and after infection were fatty acid esters. The disease caused an elevation in levels of mEthyl oleate, methyl palmitate, and methyl stearate, respectively. Further, the disease drove to the disappearance of methyl palmitoleate, and methyl laurate. Conversely, methyl linolelaidate, and Ethyl oleate were identified only in infected larvae. A high reduction in diisooctyl phthalate was recorded after the infection. Interestingly, antimicrobial activities were confirmed for haemolymph of infected honey bee larvae. In spite of the presence of some previously known bioactive compounds in healthy larvae there were no antimicrobial activities.
The use of polymorphic state modifiers in solid lipid microparticles: The role of structural modifications on drug release performance.[Pubmed:37995834]
Eur J Pharm Sci. 2024 Jan 1;192:106650.
This study investigates the correlation between the structural and release properties of solid lipid microparticles (MPs) of tristearin containing 5 % w/w of four different liquid additives used as crystal modifiers: isopropyl myristate (IM), Ethyl oleate (EO), oleic acid (OA) and medium chain triglycerides (MCT). All additives accelerated the conversion of the unstable alpha-form of tristearin, formed after the MPs manufacturing, to the stable beta-polymorph and the transformation was completed within 24 h (for IM and EO) or 48 h (for OA and MCT). The kinetic of polymorphic transition at 25 degrees C was investigated by simultaneous synchrotron SAXS/WAXS and DSC analysis after melting and subsequent cooling of the lipid mixture. After crystallization in the alpha-phase, additives accelerate the solid-solid phase transformation to beta-tristearin. SAXS data showed that two types of structural modifications occurred on MPs during storage: compaction of the crystal packing (slight decrease in lamellar thickness) and crystal growth (increased number of stacked lipid lamellae). The release behavior of a model hydrophilic drug (caffeine) at two different amounts (15 % and 30 %) from MPs was studied in water and biorelevant media simulated the gastric and intestinal environment. It was particularly significant that the introduction of IM, EO and MCT were able to prolong the drug release in water, passing from a diffusion-based Higuchi kinetics to a perfect zero-order kinetic. Moreover, the overall release profiles were higher in biorelevant media, where erosion/digestion of MPs was observed. After 6 months, a moderate but statistically significant change in release profile was observed for the MPs with IM and EO, which can be correlated with the time-dependent structural alterations (i.e. larger average crystallite size) of these formulations; while MPs with OA or MCT displayed stable release profiles. These findings help to understand the correlation between release behavior, polymorphism and supramolecular-level structural modification of lipid formulations containing crystal modifiers.
Adsorption of lipases on porous silica-based materials for esterification in a solvent-free system.[Pubmed:37900269]
3 Biotech. 2023 Nov;13(11):380.
This study deals with lipase immobilization on micro- and mesoporous silica-based materials. The effects of the type of support (silica MCM-41, zeolite HZSM-5 (SAR 25), zeolite HZSM-5 (SAR 280), and the silica-aluminas Siral 10, Siral 20, and Siral 40) were investigated on the immobilization of lipase B from Candida antarctica (CALB) and lipase from Rhizomucor miehei (RML). The supports that allowed the highest immobilization efficiencies for the CALB were Siral 40 (91.4%), HZSM-5 (SAR 280) (90.6%), and MCM-41 (89.4%). Siral 20 allowed the highest immobilization efficiency for RML (97.6%), followed by HZSM-5 (SAR 25) (77.1%) and HZSM-5 (SAR 280) (62.7%). The effect of protein concentration on lipase immobilization was investigated, and the results adjusted well on the Langmuir isotherm model (R(2) > 0.9). The maximum protein adsorption capacity of the support determined by the Langmuir model was equal to 10.64 and 20.97 mg(protein) g(support)(-1) for CALB and RML, respectively. The effects of pH (pH 7.0 and pH 11.0) and phosphate buffer solution concentration (5 and 100 mmol L(-1)) were also investigated on lipase immobilization. The immobilization efficiency for both lipases was similar for the different pH values. The use of 100 mmol L(-1) phosphate buffer decreased the lipase immobilization efficiency. The biocatalysts (CALB-Siral 40 and RML-Siral 20) were tested in the Ethyl oleate synthesis. The conversion of 61.7% was obtained at 60 degrees C in the reaction catalyzed by CALB-Siral 40. Both heterogeneous biocatalysts showed increased thermal stability compared with their free form. Finally, the reuse of the biocatalysts was studied. CALB-Siral 40 and RML-Siral 20 maintained about 30% of the initial conversion after 3 batches of Ethyl oleate synthesis. Silica-aluminas (Siral 20 and 40) proved to be a support that allowed a high efficiency of immobilization of lipases and activity for esterification reaction.
Insights into microbial communities and metabolic profiles in the traditional production of the two representative Hongqu rice wines fermented with Gutian Qu and Wuyi Qu based on single-molecule real-time sequencing.[Pubmed:37803808]
Food Res Int. 2023 Nov;173(Pt 2):113488.
Hongqu rice wine, a famous traditional fermented alcoholic beverage, is brewed with traditional Hongqu (mainly including Gutian Qu and Wuyi Qu). This study aimed to compare the microbial communities and metabolic profiles in the traditional brewing of Hongqu rice wines fermented with Gutian Qu and Wuyi Qu. Compared with Hongqu rice wine fermented with Wuyi Qu (WY), Hongqu rice wine fermented with Gutian Qu (GT) exhibited higher levels of biogenic amines. The composition of volatile flavor components of Hongqu rice wine brewed by different fermentation starters (Gutian Qu and Wuyi Qu) was obviously different. Among them, ethyl acetate, isobutanol, 3-methylbutan-1-ol, ethyl decanoate, ethyl palmitate, Ethyl oleate, nonanoic acid, 4-ethylguaiacol, 5-pentyldihydro-2(3H)-furanone, ethyl acetate, n-decanoic acid etc. were identified as the characteristic aroma-active compounds between GT and WY. Microbiome analysis based on high-throughput sequencing of full-length 16S rDNA/ITS-5.8S rDNA amplicons revealed that Lactococcus, Leuconostoc, Pseudomonas, Serratia, Enterobacter, Weissella, Saccharomyces, Monascus and Candida were the predominant microbial genera during the traditional production of GT, while Lactococcus, Lactobacillus, Leuconostoc, Enterobacter, Kozakia, Weissella, Klebsiella, Cronobacter, Saccharomyces, Millerozyma, Monascus, Talaromyces and Meyerozyma were the predominant microbial genera in the traditional fermentation of WY. Correlation analysis revealed that Lactobacillus showed significant positive correlations with most of the characteristic volatile flavor components and biogenic amines. Furthermore, bioinformatical analysis based on PICRUSt revealed that microbial enzymes related to biogenic amines synthesis were more abundant in GT than those in WY, and the enzymes responsible for the degradation of biogenic amines were less abundant in GT than those in WY. Collectively, this study provides important scientific data for enhancing the flavor quality of Hongqu rice wine, and lays a solid foundation for the healthy and sustainable development of Hongqu rice wine industry.
Anti-osteoporosis effects of triterpenoids from the fruit of sea buckthorn (Hippophae rhamnoides) through the promotion of osteoblast differentiation in mesenchymal stem cells, C3H10T1/2.[Pubmed:37751030]
Arch Pharm Res. 2023 Oct;46(9-10):771-781.
In a previous study, we discovered that the ethanolic extract of sea buckthorn (Hippophae rhamnoides) fruits exhibited anti-osteoporosis effects both in vitro and in vivo. Through bioassay-guided fractionation, we identified the hexane fraction (HRH) as the active fraction, which was further fractionated using preparative HPLC. Among the resulting six fractions, HRHF4 showed significant activity. In the present study, we focused on the bioassay-guided isolation of bioactive compounds from the HRHF4 fraction. We successfully identified the active HRHF43 fraction, which led us to the isolation of potential bioactive compounds (1-6). The chemical structures of these compounds were determined using NMR data, LC-MS analysis, and HR-ESI-MS data as four triterpenes, ursolic acid (1), uvaol (2), oleanolic aldehyde (3), and ursolic aldehyde (4), together with two fatty acids, methyl linoleate (5) and Ethyl oleate (6). To evaluate the efficacy of promoting osteoblast differentiation and the expression of mRNA biomarkers related to osteogenesis, we tested the isolated compounds in the mouse mesenchymal stem cell line, C3H10T1/2. Alkaline phosphate staining demonstrated that triterpenes (1-4) displayed osteogenic activity. Particularly noteworthy, ursolic aldehyde (4) exhibited the most potent effect, showing an 11.2-fold higher activity at a concentration of 10 mug/mL compared to the negative control. Moreover, ursolic aldehyde (4) upregulated the gene expression of bone formation-related biomarkers, including Runx2, Osterix, Alp, and Osteopontin. These findings suggest that the fruit extract of H. rhamnoides may have potential as a nutraceutical for promoting bone health, with ursolic aldehyde (4) identified as an active constituent.
Potential Correlation between Microbial Diversity and Volatile Flavor Substances in a Novel Chinese-Style Sausage during Storage.[Pubmed:37685124]
Foods. 2023 Aug 24;12(17):3190.
A novel Chinese-style sausage with Chinese traditional fermented condiments used as additional ingredients is produced in this study. The aim of this study was to investigate the microbial community's structure, the volatile flavor substances and their potential correlation in the novel Chinese sausage. High-throughput sequencing (HTS) and solid-phase microextraction-gas chromatography-mass spectrometry (GC-MS) were, respectively, used to analyze the microbial diversity and volatile flavor substances of the novel Chinese-style sausage during storage. The results showed that Firmicutes, Proteobacteria and Actinobacteria were the predominant bacterial genera, and Hyphopichia and Candida were the predominant fungal genera. A total of 88 volatile flavor substances were identified through GC-MS, among which 18 differential flavor compounds were screened (VIP > 1), which could be used as potential biomarkers to distinguish the novel sausages stored for different periods. Lactobacillus exhibited a significant negative correlation with 2,3-epoxy-4,4-dimethylpentane and acetoin and a significant positive correlation with 2-phenyl-2-butenal. Hyphopichia significantly positively correlated with ester. Leuconostoc significantly positively correlated with ethyl caprate, ethyl palmate, ethyl tetradecanoate and Ethyl oleate while it negatively correlated with hexanal. This study provides a theoretical basis for revealing the flavor formation mechanisms and the screening of functional strains for improving the flavor quality of the novel Chinese-style sausage.
Metagenomic Insights into the Regulatory Effects of Microbial Community on the Formation of Biogenic Amines and Volatile Flavor Components during the Brewing of Hongqu Rice Wine.[Pubmed:37628073]
Foods. 2023 Aug 16;12(16):3075.
As one of the typical representatives of Chinese rice wine (Huangjiu), Hongqu rice wine is produced with glutinous rice as the main raw material and Hongqu as the fermentation starter. The complex microbial flora in the brewing process may have a great influence on the formation of the flavor quality and drinking safety of Hongqu rice wine. Previous studies have shown that high biogenic amine (BA) content in rice wine has potential physiological toxicity and has become a bottleneck problem restricting the development of the rice wine industry. This study aimed to evaluate the regulatory effects of the microbial community on the formation of BAs and volatile flavor components during the brewing of Hongqu rice wine. The results demonstrated that histamine, putrescine, cadaverine, tyramine, tryptamine, spermine, and spermidine were the main BAs in Hongqu rice wine. The contents of putrescine, cadaverine, histamine, tyramine, and spermidine in Hongqu rice wine of HBAs (with higher BAs content) were significantly higher than those in LBAs (with lower BAs content). GC-MS testing results showed that there were significant differences in the composition of volatile organic compounds (VOCs) between HBAs and LBAs. Among them, VOCs such as 2-methoxy-4-vinylphenol, ethyl caprate, phenethyl acetate, ethyl lactate, ethyl myristate, ethyl palmitate, ethyl n-octadecanoate, Ethyl oleate, and ethyl linoleate were identified as the characteristic volatile components with significant differences between HBAs and LBAs. Microbiome analysis based on metagenomic sequencing revealed that unclassified_g_Pantoea, Klebsiella pneumoniae, Panobacter disperse, unclassified_f_Enterobacteriaceae, Leuconostoc mesenteroides, and Saccharomyces cerevisiae were the dominant microbial species in the HBA brewing process, while Weissella confuse, Pediococcus acidilactici, Saccharomyces cerevisiae, and Aspergillus niger were the dominant microbial species in the LBA brewing process. Furthermore, correlation heatmap analysis demonstrated that BAs were positively related to Lactobacillus curvatus, Lactococcus lactis, and Leuconostoc mesenteroides. Bioinformatical analysis based on the KEGG database revealed that the microbial genes encoding enzymes involved in BAs' synthesis were more abundant in HBAs, and the abundances of microbial genes encoding enzymes related to BAs' degradation and the metabolism of characteristic volatile components were higher in LBAs. Overall, this work provides important scientific data for enhancing the flavor quality of Hongqu rice wine and lays a solid foundation for the healthy development of the Hongqu rice wine industry.
GC-MS Analysis of Persicaria bistorta: Uncovering the Molecular Basis of Its Traditional Medicinal Use.[Pubmed:37515679]
Appl Biochem Biotechnol. 2024 Apr;196(4):2270-2288.
Persicaria bistorta is a perennial herb used traditionally in treating various ailments, including diarrhea, abdominal pain, and bleeding. In this study, we used gas chromatography-mass spectrometry (GC-MS) analysis to identify the chemical composition of Persicaria bistorta. The GC-MS analysis revealed the presence of several compounds, including flavonoids, tannins, saponins, and alkaloids. Among those, the most important from medicinal points of view are Ethyl oleate (3%), cyclotetradecane (4.74%), dodecanoic acid (4.69%), hexadecanoic acid (5.61%), tetradecane (5.25%), cis-13-octadecenoic acid (10.91%), and bis(2-ethylhexyl) phthalate (32%). The GC-MS analysis of ethanolic fraction of Persicaria bistorta involved in antibacterial activity showed about 18 compounds. Among those, the most important from a medicinal and nutritional point of view are bis(2-ethylhexyl) phthalate (42.20%), 6-octadecenoic acid methyl ester, (Z)- (10.37%), Ethyl oleate (6.84%), hexadecanoic acid methyl ester (6.67%), and methyl ester and oleic acid (5.27%). Reported biological antibacterial activity has shown that the main compound determined in both extracts was bis(2-ethylhexyl) phthalate, which has higher peak area percentage in ethanolic extract than in ethyl acetate fraction. Some oily compounds important for health because of their cis-conformation were also revealed in the given study like Ethyl oleate and oleic acid. Overall, results suggest that Persicaria bistorta may have therapeutic potential and warrant further investigation. Further research is needed to confirm the efficacy and safety of Persicaria bistorta as a natural medicine and determine its active compounds' mechanisms of action.
The Relationship between Microbial Community Succession and Flavor Formation during the Natural Fermentation of Hongqu sufu.[Pubmed:37509892]
Foods. 2023 Jul 23;12(14):2800.
To study the diversity of microbial flora in Hongqu sufu and analyze the characteristics of special flavor compounds, this study took self-made Hongqu sufu as the research object. Dynamic changes in sufu during fermentation were studied. High-throughput sequencing (HTS) was used to analyze changes in the diversity of fungal and bacterial communities during fermentation. The results showed that at the phylum level, the dominant fungal phyla were identified, Mucormyces and Ascomycetes. The dominant bacterial phyla were Proteobacteria and Firmicutes. At the genus level, the dominant fungal genera were identified as Actinomucor, Monascus, and Aspergillus. The dominant bacterial genera were Pseudomonas, Aneurimibacillus, Sphingobacterium, and Bacillus. Headspace solid-phase microextraction gas chromatography-mass spectrometry (HS-SPME-GC-MS) combined with technology that can dynamically change flavor compounds was explored to investigate the correlation between microbiota and flavor compounds. In different stages of fermentation, 75 main volatile organic compounds were identified, including seven alcohols, four acids, 16 alkanes, 14 olefins, seven kinds of aldehydes, two kinds of ketones, 10 kinds of esters, one kind of phenol, one kind of sulfur-containing compound, one benzene, and 12 other compounds. The correlation analysis between flora and flavor compounds showed that the fungi genera Alternaria and Pichia were significantly correlated with most flavor compounds. Bacteria genera including Weissella, Hafnia-Obesumbacterium, and Leuconostoc had a strong positive correlation with Ethyl oleate.