Reduction of citrinin biosynthesis by fatty acids in Monascus fermented food

2012 ◽  
Vol 5 (2) ◽  
pp. 163-167
Author(s):  
B.P. Panda ◽  
M. Ali
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Octanoic Acid ◽  
Decanoic Acid ◽  
Fermentation Medium ◽  
Fermented Food ◽  
Hexanoic Acid ◽  
Red Yeast Rice ◽  
Octadecanoic Acid ◽  
Rice Medium

Monascus-fermented food (red yeast rice, red mould rice, angkak) contains various useful secondary metabolites, for example lovastatin, along with citrinin, a hepatonephrotoxic agent. Fatty acids such as octanoic acid, oleic acid, octadecanoic acid, decanoic acid, hexanoic acid at increasing concentrations concentrations (0.1, 0.5, 1, 3 and 5%) were incorporated in solid fermentation medium to influence the citrinin level in red mould rice. Out of all the fatty acids tested, oleic acid and octadecanoic acid were ineffective, hexanoic acid and octanoic acid were moderately effective, whereas decanoic acid was highly effective in controlling citrinin biosynthesis. On the eleventh day of solid-state fermentation in red mould rice medium supplemented with 5% decanoic acid, citrinin concentration was 28 ng/g (lower than the advisory citrinin limit of 200 ng/g), whereas lovastatin concentration was 1.574 mg/g. Fermentation of rice medium supplemented with decanoic acid could produce a safer Monascus-based functional food than the non-supplemented medium.

DEODORIZING MORINDA CITRIFOLIA (MENGKUDU) STRONG ODOR JUICE BY β-CYCLODEXTRIN-ORGANIC ACIDS INCLUSION

2016 ◽  
Vol 78 (10) ◽  
Author(s):  
Yeap Shong Yien ◽  
Osman Hassan ◽  
Saiful Irwan Zubairi
Keyword(s):  
Fatty Acids ◽  
Melting Point ◽  
Inclusion Complex ◽  
Octanoic Acid ◽  
Dry Weight ◽  
Decanoic Acid ◽  
Hexanoic Acid ◽  
Morinda Citrifolia ◽  
Therapeutic Effects ◽  
Clinical Practices

Morinda citrifolia (noni) which is locally known as mengkudu in Malaysia, is a small evergreen tree usually found growing in open coastal regions at sea level and in forest areas. It has been reported to have  various therapeutic effects, including having anticancer activities, in clinical practices and laboratory animal models. However, consumers mostly avoid consuming mengkudu products due to  mengkudu’s sensory properties such as a strong rancid-like odor that is released when the mengkudu fruit is fully ripe. Therefore, this study was  conducted to determine the effectiveness of β-cyclodextrin in deodorizing the unpleasant odors in mengkudu juice which are mainly caused by medium chain fatty acids such as hexanoic acid, octanoic acid and decanoic acid. Initially, the optimal molar ratio for the encapsulation of hexanoic, octanoic and decanoic acid by β-cyclodextrin was constructed as a model system prior to the encapsulation of the juice. The formation of inclusion complex between all acids and β-cyclodextrin was verified by means of differential scanning calorimetry (DSC). Next, four dry weight ratios of mengkudu juice to β–cyclodextrin (1:0.5, 1:1, 1:1.5 and 1:2) were selected to determine the degree of the effectiveness of β-cyclodextrin in encapsulating unpleasant odors via gas chromatography-mass spectrometry (GC-MS). Based on the results, inclusion complex formation was confirmed by DSC through the disappearance of a melting point for pure acid, and shifting to a lower melting point from the pure β–cyclodextrin after the encapsulation process. Moreover, there were significant differences observed between hexanoic acid and octanoic acid content in the mengkudu juice before and after adding β-cyclodextrin (p<0.05). On the other hand, the results obtained from GC-MS and sensory evaluation had contributed to an optimum entrapment of fatty acids at the optimal dry weight ratio of 1:0.5 (dry weight of mengkudu: β-cyclodextrin). Hence, the ability of β-cyclodextrin as a masking agent has been proven to be able to reduce the odor-based fatty acids in mengkudu juice.

scholarly journals Studies on the specificity of Candida rugosa lipase catalyzed esterification reactions in organic media

2006 ◽  
Vol 71 (1) ◽  
pp. 31-41 ◽  
Author(s):  
Dejan Bezbradica ◽  
Ivana Karalazic ◽  
Nevena Ognjanovic ◽  
Dusan Mijin ◽  
Slavica Siler-Marinkovic ◽  
...  
Keyword(s):  
Octanoic Acid ◽  
Candida Rugosa ◽  
Octadecenoic Acid ◽  
Decanoic Acid ◽  
Candida Rugosa Lipase ◽  
Reaction Rates ◽  
Initial Reaction ◽  
Octadecanoic Acid ◽  
Esterification Reactions ◽  
Commercial Lipase

In this study, the feasibility of the synthesis of various flavor esters catalyzed by a commercial lipase from Candida rugosa was investigated and the process parameters were optimized. Lipase from C. rugosa successfully catalyzed the synthesis of 19 esters. The highest yields, of more than 90 % after 20 h, were observed in the synthesis of short-chain esters, pentyl propanoate, isopentyl butanoate, and butyl butanoate. Increasing the number of carbon atoms of both substrates above 8 caused a significant decrease of the initial reaction rates and the final yields. The enzyme showed surprisingly low affinity towards pentanoic acid and hexanoic acid, compared with the higher homologues, octanoic acid and decanoic acid. In addition to the number of carbon atoms, the structure of the substrates had a significant influence on the enzyme activity. Namely, the activity of the enzyme towards isopropanol was significantly lower compared with n-propanol. Additionally, cis-9-octadecenoic acid was a better substrate than octadecanoic acid, its saturated analogue.

Uncoupling of cardiac cells by fatty acids: structure-activity relationships

1991 ◽  
Vol 260 (3) ◽  
pp. C439-C448 ◽  
Author(s):  
J. M. Burt ◽  
K. D. Massey ◽  
B. N. Minnich
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Unsaturated Fatty Acids ◽  
Saturated Fatty Acids ◽  
Decanoic Acid ◽  
Cardiac Cells ◽  
Neonatal Rat ◽  
Heart Cells ◽  
Dependent Manner ◽  
Rat Heart Cells

The permeability and conductance of gap junctions between pairs of neonatal rat heart cells were rapidly and reversibly decreased by oleic acid in a dose- and time-dependent manner. Other unsaturated fatty acids (C-18: cis 6, 9, or 11, and C-18, 16, and 14, cis 9), saturated fatty acids (C-10, 12, and 14), and saturated fatty alcohols (C-8, 10, and 12) also caused uncoupling. The most effective compounds of the unsaturated and saturated fatty acid and saturated fatty alcohol series caused essentially complete uncoupling at comparable aqueous concentrations. However, oleic acid uncoupled cells at membrane concentrations as low as 1 mol%, whereas decanoic acid required upwards of 35 mol%. The channels that support the action potential remained functional at these same membrane concentrations. The data are discussed in terms of the possible mechanism by which these compounds cause uncoupling and the possible role of uncoupling by nonesterified free fatty acids in the initiation of arrhythmias during and after ischemic insults.

scholarly journals Evaluation of the antimicrobial performance of menthol and menthol-based deep eutectic solvents as potential future antibiotic

2021 ◽  
Vol 287 ◽  
pp. 02010
Author(s):  
Nor Azrini Nadiha Azmi ◽  
Amal Elgharbawy ◽  
Hamzah Mohd Salleh ◽  
Adeeb Hayyan
Keyword(s):  
Fatty Acids ◽  
Octanoic Acid ◽  
Deep Eutectic Solvents ◽  
Decanoic Acid ◽  
Antimicrobial Activities ◽  
Gram Negative Bacteria ◽  
Eutectic Mixtures ◽  
Start Up ◽  
Antimicrobial Performance ◽  
Insight Into

Triggered by the strong antimicrobial activities of menthol and various fatty acids, eutectic mixtures based on the components are developed, producing new solvents that have possibilities to become a new antibiotic. This study aims to provide an insight into the antimicrobial activities of the new deep eutectic solvents (DESs) developed. Menthol-based DES combined with fatty acids, namely propionic acid, butanoic acid, hexanoic acid, octanoic acid, decanoic acid, and levulinic acid, were successfully obtained and their thermal profile was analyzed. The antimicrobial potential of DES systems was evaluated against both Gram positive and Gram negative bacteria. Owing to the activities of the start-up components, the results are considered promising, and this illustrates the potential of the newly obtained DESs as a new antimicrobial agent in various fields such as food, cosmetics as well as pharmaceutical.

(omega-1)-Hydroxymonocarboxylic acids in urine of infants fed medium-chain triglycerides.

1981 ◽  
Vol 27 (10) ◽  
pp. 1661-1664 ◽  
Author(s):  
Y Shigematsu ◽  
T Momoi ◽  
M Sudo ◽  
Y Suzuki
Keyword(s):  
Mass Spectrometry ◽  
Fatty Acids ◽  
Octanoic Acid ◽  
Monocarboxylic Acid ◽  
Decanoic Acid ◽  
Gas Chromatography Mass Spectrometry ◽  
Medium Chain Triglycerides ◽  
Medium Chain ◽  
Chain Acyl ◽  
Total Fatty Acids

Abstract Organic acids in the urine of infants fed a formula containing medium-chain triglycerides (octanoic acid 49% and decanoic acid 26% of total fatty acids) were determined by gas chromatography-mass spectrometry. We found a considerable amount of 5-hydroxyhexanoic acid and 7-hydroxyoctanoic acid, but no detectable 9-hydroxydecanoic acid, as well as a large amount of C6-C10-dicarboxylic acid. We believe that such acids are derived, via (omega-1)-hydroxylation, from medium-chain monocarboxylic acid or medium-chain acyl-CoA in the liver cell. The degree of (omega-1)-hydroxylation of medium-chain fatty acids relative to omega-hydroxylation apparently increases as the chain length of the fatty acids decreases.

scholarly journals Fatty Acids Taste Intensity Ratings Before and After Sour Taste Adaptation

2020 ◽  
Vol 4 (Supplement_2) ◽  
pp. 742-742
Author(s):  
Eunjin Cheon ◽  
Richard Mattes
Keyword(s):  
Fatty Acids ◽  
Acetic Acid ◽  
Fatty Acid ◽  
Acid Solution ◽  
Octanoic Acid ◽  
Decanoic Acid ◽  
Acid Solutions ◽  
Significant Difference ◽  
Before And After

Abstract Objectives Recent research indicates that the taste quality of fatty acids, called ‘Oleogustus’, differs from the traditionally accepted five basic tastes. However, the actual quality of the sensation has not been characterized. One question is whether there is a sour component because very short-chain fatty acids, like acetic acid, the sour tastant in vinegar, is structurally a fatty acid. The present study investigated the quality sensation of fatty acids of graded chain length. Methods Sensory stimuli were acetic acid, butyric acid, hexanoic acid, octanoic acid, decanoic acid, lauric acid, oleic acid, and linoleic acid emulsions and palmitic acid, stearic acid powder. The intensity of the samples before and after expectorating was measured. Next, participants repeatedly sipped, held for 5 seconds, and expectorated a sour solution (0.09% w/w) and rated the intensity on a gLMS until the intensity was lower than “weak”. After adaption to the sour solution, the intensity of the sample was measured before and after expectorating. Participants recorded the quality of each sample. Results The intensity of acetic acid was significantly lower after adaptation (P &lt; 0.04) that before adaptation and a similar trend was noted for butyric acid. The other fatty acids were not affected by adaptation. The intensities of all liquid samples except the octanoic acid solution showed a significant difference between before and after expectorating the samples. The intensities of acetic, butyric and hexanoic acids were lower after expectorating the samples than the intensities before expectorating the samples (P &lt; 0.05) while the intensities of decanoic acid, lauric acid, oleic acid, and linoleic acid (P &lt; 0.05) were lower after expectorating. There was no significant difference in intensity of the palmitic acid solution and the intensity of the stearic acid solution between before and after expectorating. Conclusions The results showed that fatty acids with chain lengths great than 4 have a unique taste other than the sourness. In addition, short-chain fatty acid solutions had higher intensity before expectorating the solutions while the medium- and long-chain fatty acid solutions had higher intensity after expectorating solutions, indicating that there is a different persistence time for fatty acid directly related to chain-length. Funding Sources This study has no sponsors.

scholarly journals Oleic Acid Directly Regulates POMC Neuron Excitability in the Hypothalamus

2009 ◽  
Vol 101 (5) ◽  
pp. 2305-2316 ◽  
Author(s):  
Young-Hwan Jo ◽  
Ya Su ◽  
Roger Gutierrez-Juarez ◽  
Streamson Chua
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Alternative Fuels ◽  
Octanoic Acid ◽  
Carnitine Palmitoyltransferase ◽  
High Fat ◽  
Neuron Excitability ◽  
Carnitine Palmitoyltransferase 1 ◽  
Fat Feeding ◽  
External Glucose

The mammalian CNS relies on a constant supply of external glucose for its undisturbed operation. However, neurons can readily switch to using fatty acids and ketones as alternative fuels. Here, we show that oleic acid (OA) excites pro-opiomelanocortin (POMC) neurons by inhibition of ATP-activated potassium (KATP) channels. The involvement of KATP channels is further supported by experiments in SUR1 KO animals. Inhibition of β-oxidation using carnitine palmitoyltransferase-1 inhibitors blocks OA-induced depolarization. The depolarizing effect of OA is specific because it is not mimicked by octanoic acid. Furthermore, OA does not regulate the excitability of agouti-related peptide neurons. High-fat feeding alters POMC neuron excitability, but not its response to OA. Thus β-oxidation in POMC neurons may mediate the appetite-suppressing (anorexigenic) effects of OA.

Synthesis and Characterization of New Bolaform Surfactant from Palm Oil Derivative

2011 ◽  
Vol 364 ◽  
pp. 95-99 ◽  
Author(s):  
S.C. Goh ◽  
S.Y. Chin ◽  
L.M.S. Lee ◽  
Mohd Ambar Yarmo ◽  
N.I. Nik Yusof
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Thin Layer ◽  
Stationary Phase ◽  
Palm Oil ◽  
Atmospheric Pressure ◽  
Synthesis And Characterization ◽  
Octadecanoic Acid ◽  
Layer Chromatography

In this research, new chemistry is explored through a simple, efficient and cheap method to synthesize new surfactants from palm oil fatty acids. Oleic acid, which is one of the major fatty acids in palm oil, has been used as a starting material for the synthesis of surfactants. This study focuses on the synthesis and characterization of bolaform surfactants from oleic acid. For this purpose, two steps reaction will be carried out: Firstly, consisted of hydrobromination of oleic acid followed by reaction of 10-bromo-octadecanoic acid with ethane-1,2-dithiol and butane-1,2-dithiol. During the first stage of the reaction, hydrobromination of oleic acid was carried out by adding hydrobromic acid into the oleic acid. The reaction was carried out in benzene as solvent at 30°C and atmospheric pressure. This reaction gives 73% yield of 10-bromo-octadecanoic acid and it yield a black brownish liquid which have the m/z 363.2056 by ESI-MS(ToF) and –CH2-CHBr-CH2-shift (4.02 ppm) was well defined in1H-NMR. The separation of 10-bromo-octadecanoic acid was done through thin layer chromatography (TLC) with chloroform and methanol as the eluent and silica plate grade 60 F254as the stationary phase. The second stage of reaction was reacting the 10-bromo-octadecanoic acid with ethane-1,2-dithiol and butane-1,2-dithiol in THF as the solvent and 1,8-Diazabicyclo [5.4.0] undec-7-ene (DBU) as the catalyst respectively. These reactions were carried out at 30°C and atmospheric pressure. Product obtained was a two layers black brownish liquid with white colour precipitate gives m/z: 659.4813 for ethane-1,2-dithiol and m/z:686.5278 for butane-1,4-dithiol respectively using ESI-MS (ToF) mass spectroscopy. Separation was done on both bolaform surfactants through thin layer chromatography (TLC) with hexane and ethyl acetate as eluent and silica plate grade 60 F254as stationary phase, and finally followed by column chromatography. These two new surfactants will be tested for their physical-chemical properties as well as apply on nanomaterial stabilizer.

scholarly journals The β-Oxidation Systems of Escherichia coli and Salmonella enterica Are Not Functionally Equivalent

2006 ◽  
Vol 188 (2) ◽  
pp. 599-608 ◽  
Author(s):  
Surtaj Hussain Iram ◽  
John E. Cronan
Keyword(s):  
Escherichia Coli ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Octanoic Acid ◽  
Decanoic Acid ◽  
Wild Type ◽  
Fatty Acid Degradation ◽  
E Coli ◽  
Acid Degradation ◽  
Type Strains

ABSTRACT Based on its genome sequence, the pathway of β-oxidative fatty acid degradation in Salmonella enterica serovar Typhimurium LT2 has been thought to be identical to the well-characterized Escherichia coli K-12 system. We report that wild-type strains of S. enterica grow on decanoic acid, whereas wild-type E. coli strains cannot. Mutant strains (carrying fadR) of both organisms in which the genes of fatty acid degradation (fad) are expressed constitutively are readily isolated. The S. enterica fadR strains grow more rapidly than the wild-type strains on decanoic acid and also grow well on octanoic and hexanoic acids (which do not support growth of wild-type strains). By contrast, E. coli fadR strains grow well on decanoic acid but grow only exceedingly slowly on octanoic acid and fail to grow at all on hexanoic acid. The two wild-type organisms also differed in the ability to grow on oleic acid when FadR was overexpressed. Under these superrepression conditions, E. coli failed to grow, whereas S. enterica grew well. Exchange of the wild-type fadR genes between the two organisms showed this to be a property of S. enterica rather than of the FadR proteins per se. This difference in growth was attributed to S. enterica having higher cytosolic levels of the inducing ligands, long-chain acyl coenzyme As (acyl-CoAs). The most striking results were the differences in the compositions of CoA metabolites of strains grown with octanoic acid or oleic acid. S. enterica cleanly converted all of the acid to acetyl-CoA, whereas E. coli accumulated high levels of intermediate-chain-length products. Exchange of homologous genes between the two organisms showed that the S. enterica FadE and FadBA enzymes were responsible for the greater efficiency of β-oxidation relative to that of E. coli.

scholarly journals Astrocyte metabolism of the medium-chain fatty acids octanoic acid and decanoic acid promotes GABA synthesis in neurons via elevated glutamine supply

2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Jens V. Andersen ◽  
Emil W. Westi ◽  
Emil Jakobsen ◽  
Nerea Urruticoechea ◽  
Karin Borges ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Neurological Disorders ◽  
Octanoic Acid ◽  
Brain Slices ◽  
Decanoic Acid ◽  
Protective Effects ◽  
Medium Chain ◽  
Medium Chain Fatty Acids ◽  
Metabolic Substrates ◽  
Gaba Synthesis

AbstractThe medium-chain fatty acids octanoic acid (C8) and decanoic acid (C10) are gaining attention as beneficial brain fuels in several neurological disorders. The protective effects of C8 and C10 have been proposed to be driven by hepatic production of ketone bodies. However, plasma ketone levels correlates poorly with the cerebral effects of C8 and C10, suggesting that additional mechanism are in place. Here we investigated cellular C8 and C10 metabolism in the brain and explored how the protective effects of C8 and C10 may be linked to cellular metabolism. Using dynamic isotope labeling, with [U-13C]C8 and [U-13C]C10 as metabolic substrates, we show that both C8 and C10 are oxidatively metabolized in mouse brain slices. The 13C enrichment from metabolism of [U-13C]C8 and [U-13C]C10 was particularly prominent in glutamine, suggesting that C8 and C10 metabolism primarily occurs in astrocytes. This finding was corroborated in cultured astrocytes in which C8 increased the respiration linked to ATP production, whereas C10 elevated the mitochondrial proton leak. When C8 and C10 were provided together as metabolic substrates in brain slices, metabolism of C10 was predominant over that of C8. Furthermore, metabolism of both [U-13C]C8 and [U-13C]C10 was unaffected by etomoxir indicating that it is independent of carnitine palmitoyltransferase I (CPT-1). Finally, we show that inhibition of glutamine synthesis selectively reduced 13C accumulation in GABA from [U-13C]C8 and [U-13C]C10 metabolism in brain slices, demonstrating that the glutamine generated from astrocyte C8 and C10 metabolism is utilized for neuronal GABA synthesis. Collectively, the results show that cerebral C8 and C10 metabolism is linked to the metabolic coupling of neurons and astrocytes, which may serve as a protective metabolic mechanism of C8 and C10 supplementation in neurological disorders.

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