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A new oxolane from Enterobacter cloacae

Yap AC, Chan KG, Sim KS, Choo YM

Nat Prod Res, 2016 Apr;30(7):783-8.
PMID: 26252083 DOI: 10.1080/14786419.2015.1065492

Enterobacter cloacae is a highly pathogenic Gram-negative proteobacterium which is responsible for a wide array of infections. In the present study, the fermentation culture of E. cloacae has yielded one new oxolane compound, Rimboxo (1) in addition to three known compounds, i.e. Maculosine (2), phenylacetic acid (3) and methyl myristate (4). These compounds were isolated and characterised using extensive chromatographic and spectroscopic methods, and were subjected to cytotoxicity evaluations.

Matched MeSH terms: Myristic Acid
Unusual poly(3-hydroxyalkanoate) (PHA) biosynthesis behavior of Pseudomonas putida Bet001 and Delftia tsuruhatensis Bet002 isolated from palm oil mill effluent

Razaif-Mazinah MRM, Anis SNS, Harun HI, Rashid KA, Annuar MSM

Biotechnol Appl Biochem, 2017 Mar;64(2):259-269.
PMID: 26800648 DOI: 10.1002/bab.1482

Pseudomonas putida Bet001 and Delftia tsuruhatensis Bet002, isolated from palm oil mill effluent, accumulated poly(3-hydroxyalkanoates) (PHAs) when grown on aliphatic fatty acids, sugars, and glycerol. The substrates were supplied at 20:1 C/N mole ratio. Among C-even n-alkanoic acids, myristic acid gave the highest PHA content 26 and 28 wt% in P. putida and D. tsuruhatensis, respectively. Among C-odd n-alkanoic acids, undecanoic gave the highest PHA content at 40 wt% in P. putida and 46 wt% in D. tsuruhatensis on pentadecanoic acid. Sugar and glycerol gave <10 wt% of PHA content for both bacteria. Interestingly, D. tsuruhatensis accumulated both short- and medium-chain length PHA when supplied with n-alkanoic acids ranging from octanoic to lauric, sucrose, and glycerol with 3-hydroxybutyrate as the major monomer unit. In P. putida, the major hydroxyalkanoates unit was 3-hydroxyoctanoate and 3-hydroxydecanoate when grown on C-even acids. Conversely, 3-hydroxyheptanoate, 3-hydrxoynonanoate, and 3-hydroxyundecanoate were accumulated with C-odd acids. Weight-averaged molecular weight (Mw ) was in the range of 53-81 kDa and 107-415 kDa for P. putida and D. tsuruhatensis, respectively. Calorimetric analyses indicated that both bacteria synthesized semicrystalline polymer with good thermal stability with degradation temperature (Td ) ranging from 178 to 282 °C.

Matched MeSH terms: Myristic Acid
Isolation and identification of metabolites from the gram-negative proteobacteria of burkholderia cenocepacia and serratia marcescens

Chan Kg, Yap Ac, Choo Ym

Sains Malaysiana, 2016;45:1073-1077.

Burkholderia cenocepacia and Serratia marcescens are Gram-negative proteobacteria commonly found in the natural
environment and are also opportunistic pathogens that caused a number of human diseases. The fermentation culture of
Burkholderia cenocepacia yielded three compounds, 4-(2-hydroxyethoxy)-phenol (1), Maculosin (2) and methyl myristate
(3). Compound 2 was also isolated together with cyclo(L-Leu-L-Pro) (4) from Serratia marcescens. Compound 1 was
isolated from a natural source for the first time and the first isolation of compounds 2-4 was also reported from both
Burkholderia cenocepacia and Serratia marcescens.

Matched MeSH terms: Myristic Acid
Fulltext Date seed and date seed oil

Abdul Afiq, M.J., Abdul Rahman, R., Che Man, Y.B., AL-Kahtani, H.A., Mansor, T.S.T.

International Food Research Journal, 2013;20(5):2035-2043.
MyJurnal

Date palm is an important plant in arid regions with more than 20 varieties reported all over the world. Date seed is a byproduct of date fruit industry which is normally being discarded, used as animal feed ingredient or turned into non-caffeinated coffee by the Arabs. About 11-18% of date fruit weight is the seed which is composed of carbohydrates, dietary fiber, fat, ash and protein. In addition, the antioxidant content in date seed oil (DSO) was found to be comparable with olive oil, which can be as a good source of antioxidant in order to fulfill the consumers demand. Oleic acid is the major fatty acid found in DSO, followed by lauric, linoleic, palmitic and myristic acid. However, different varieties of date fruits have different fatty acid compositions. This paper reviewed the potential use of date seed and date seed oil in order to discover and develop its usage and find out the suitable application of these seed and oil.

Matched MeSH terms: Myristic Acid
Fulltext Thermal Performance Study of Composite Phase Change Material with Polyacrylicand Conformal Coating

Kee SY, Munusamy Y, Ong KS, Cornelis Metselaar HS, Chee SY, Lai KC

Materials (Basel), 2017 Jul 28;10(8).
PMID: 28773232 DOI: 10.3390/ma10080873

The composite PCM was prepared by blending polymethyl methacrylate (PMMA) and myristic acid (MA) in different weight percentages. The MA and PMMA were selected as PCM and supporting material, respectively. As liquid MA may leak out during the phase transition, this study proposes the use of two coatings, namely a polyacrylic coating and a conformal coating to overcome the leakage problem. Both coatings were studied in terms of the leakage test, chemical compatibility, thermal stability, morphology, and reliability. No leakage was found in the PCMs with coatings compared to those without under the same proportions of MA/PMMA, thus justifying the use of coatings in the present study. The chemically compatibility was confirmed by FTIR spectra: the functional groups of PCMs were in accordance with those of coatings. DSC showed that the coatings did not significantly change the melting and freezing temperatures, however, they improved the thermal stability of composite PCMs as seen in TGA analysis. Furthermore, the composite PCMs demonstrated good thermal reliability after 1000 times thermal cycling. The latent heat of melting reduced by only 0.16% and 1.02% for the PCMs coated with conformal coating and polyacrylic coating, respectively. Therefore, the proposed coatings can be considered in preparing fatty acid/PMMA blends attributed to the good stability, compatibility and leakage prevention.

Matched MeSH terms: Myristic Acid
Myristic acid defends against testicular oxidative stress, inflammation, apoptosis: Restoration of spermatogenesis, steroidogenesis in diabetic rats

Khalil ASM, Giribabu N, Yelumalai S, Shahzad H, Kilari EK, Salleh N

Life Sci, 2021 Aug 01;278:119605.
PMID: 33989665 DOI: 10.1016/j.lfs.2021.119605

Diabetes mellitus (DM) may lead to testicular-related infertility while Myristic acid (MA) is beneficial to lower hyperglycaemia. Thus, we hypothesized that MA could protect testes against hyperglycaemia-induced damage in DM. DM was induced in adult male rats by high-fat diet consumption for 12 weeks, accompanied by a single dose streptozotocin injection. Following DM confirmation, the rats were fed orally with 10 and 20 mg/kg body weight MA for 28 consecutive days. After completion of treatment, rats were sacrificed and blood, cauda epididymis and testes were harvested. Serum was separated, epididymal sperm was collected for analysis. Molecular studies of the testes were performed by qPCR, Western blotting and immunostaining. MA was found to protect the testes against oxidative stress via preventing the upregulation of RAGE, Keap1, and the downregulation of Nrf2, NQO1, HO1, SOD, CAT and GPx. MA also prevented increase in testicular inflammation and apoptosis, as indicated by low inflammatory (NF-κB p65, IKKβ, TNF-α, IL-1β and iNOS) and apoptosis (Bax and caspase-9), but high anti-apoptosis (Bcl-2) markers' levels. Besides, MA prevented the downregulation of testicular steroidogenic markers (3βHSD, 17βHSD, StAR, ARA-54 and CYP11A1). Sperm analysis revealed near normal sperm count, motility, viability, lower abnormal sperm morphology in diabetic rats received MA. MA also prevented the loss of germ cells via preventing the decreased in cell proliferative marker (PCNA) while maintaining near normal epithelial height, tubular and Leydig cell diameters in the testes in DM. MA protects the testes against damage in DM, thus maintaining spermatogenesis and steroidogenesis, consequently preserving male fertility in diabetes.

Matched MeSH terms: Myristic Acid/pharmacology*
Modulation of human lipids and lipoproteins by dietary palm oil and palm olein: a review

Sundram K

Asia Pac J Clin Nutr, 1997 Mar;6(1):12-6.
PMID: 24394646

Several human clinical trials have now evaluated palm oil's effects on blood lipids and lipoproteins. These studies suggest that palm oil and palm olein diets do not raise plasma TC and LDL-cholesterol levels to the extent expected from its fatty acid composition. With maximum substitution of palm oil in a Western type diet some coronary heart disease risk factors were beneficially modulated: HDL2-cholesterol was significantly increased while the apolipoprotein B/A1 ratio was beneficially lowered by palm oil. Comparison of palm olein with a variety of monounsaturated edible oils including rapeseed, canola, and olive oils has shown that plasma and LDL-cholesterol were not elevated by palm olein. To focus these findings, specific fatty acid effects have been evaluated. Myristic acid may be the most potent cholesterol raising saturated fatty acid. Palmitic acid effects were largely comparable to the monounsaturated oleic acid in normolipidaemic subjects while trans fatty acids detrimentally increased plasma cholesterol, LDL-cholesterol, lipoprotein Lp(a) and lowered the beneficial HDL-cholesterol. Apart from these fatty acids there is evidence that the tocotrienols in palm oil products may have a hypocholesterolaemic effect. This is mediated by the ability of the tocotrienols to suppress HMG-CoA reductase. These new findings on palm oil merit a scientific reexamination of the classical saturated fat-lipid hypothesis and its role in lipoprotein regulation.

Matched MeSH terms: Myristic Acid
Fulltext Effects of Seasonal Variability on the Physicochemical, Biochemical, and Nutritional Composition of Western Peninsular Malaysia Gracilaria manilaensis

Aroyehun AQ, Palaniveloo K, Ghazali F, Rizman-Idid M, Abdul Razak S

Molecules, 2019 Sep 10;24(18).
PMID: 31510066 DOI: 10.3390/molecules24183298

This study evaluated the effect of seasonal variation on the physicochemical, biochemical, and nutritional composition of Gracilaria manilaensis. Sampling was designed during the main monsoon seasons in Malaysia-the Southwest monsoon (SWM) and Northeast monsoon (NEM)-to understand the intraspecific variation (p < 0.05). Carbohydrates, protein, and dietary fiber were found to be higher in NEM-G. manilaensis, whereas a higher ash content was quantified in SWM-G. manilaensis. No significant differences were found in crude lipid and moisture content (p > 0.05). Vitamin B2 was calculated as (0.29 ± 0.06 mg 100 g-1) and (0.38 ± 0.06 mg 100 g-1) for the NEM and SWM samples, respectively (p < 0.05). The fatty acid profile showed the dominance of saturated fatty acids (SFAs)-palmitic acids, stearic acid, and myristic acid-while the mineral contents were found to be good sources of calcium (1750.97-4047.74 mg 100 g-1) and iron (1512.55-1346.05 mg 100 g-1). Tryptophan and lysine were recorded as the limiting essential amino acids (EAAs) in NEM G. manilaensis, while leucine and phenylalanine were found to be the limiting EAAs in the SWM samples. None of the extracts exhibited antibacterial properties against the screened strains. The study concluded that seasonal changes have a great effect on the biochemical composition of G. manilaensis.

Matched MeSH terms: Myristic Acid
Fulltext Nutrients depictions of Barhi date palm (Phoenix dactylifera L.) kernels

Mahmud, I.A., Mirghani, M.E.S., Alkhatib, M.F.R., Yusof, F., Shahabuddin, M., Rashidi, O., et al.

International Food Research Journal, 2017;24(101):0-0.
MyJurnal

Phoenix dactylifera L (Date palm) is one of the oldest known fruit crops in the world, and
the consumption of date fruits is no longer restricted to the Middle Eastern countries. Date
palm kernels are waste products of date fruit industry which are normally being discarded.
Based on their dietary fiber content; date palm kernels (DPK) have been proposed to be used
as fiber-based food supplement, caffeine free coffee alternative and animal feed ingredient.
Hence, utilization of such waste is highly desirable for the date industry. To accommodate these
benefits, and subsequent to some uses associated with DPK, this study sought to investigate the
biochemical and nutritional values of the Barhi date palm kernels (BDPK) grown in Iraq. The
results show that BDPK is an excellent source of dietary fiber (66.24 g/100g). Glutamic acid
was found to be the predominant amino acid, (0.674 g/100g), followed by Arginine and aspartic
acid (0.437 g/100g and 0.320 g/100g, respectively). Potassium was the most occurring mineral
in BDPK (2.39 g/kg), and the main sugars were sucrose and fructose (0.548 g/100g and 0.249
g/100g, respectively). Gas-liquid chromatography revealed that the main unsaturated fatty acid
(USFA) was oleic acid (40.927 mg/100g), while the main saturated fatty acid (SFA) were lauric
acid (20.270 mg/100g) and myristic acid (12.288 mg/100g). Furthermore, the BDPK depicted
considerable concentrations of vitamins, in which vitamin B5 (40.4 mg/100g) showed the
highest value. The results obtained indicate a strong potential for BDPK to be used in human
nutrition, cosmetics, and pharmaceutical applications and may provide an important economic
advantage through increasing the utilization of BDKP while also additive value will be added
to the residue.

Matched MeSH terms: Myristic Acid
Proximate, fatty acid and mineral composition of selected deep sea fish species from Southern Java Ocean and Western Sumatra Ocean, Indonesia

Suseno, S.H., Tajul, A.Y., Nadiah, W.A., Hamidah, Asti, Ali, S.

International Food Research Journal, 2010;17(4):905-914.
MyJurnal

Proximate content, fatty acid and mineral compositions were determined for the ten species of deepsea fish from Southern Java Ocean and Western Sumatra Ocean, Indonesia. The proximate composition was found to be 23.0-24.8 % protein, 1.9-4.1% fat , 0-1.75 % carbohydrate, 1.7-2.4 % ash and 70.1-72.1% water, whereas the fatty acid compositions consisted of 0.86 - 49.63 % saturated fatty acids (SFA), 0.29 - 50.09 % monounsaturated fatty acid (MUFA) and 2.85 % - 46.32 % polyunsaturated fatty acids (PUFAs). Among them, those occurring in the highest proportions were myristic acid (C14:0, 0.12-7.59%), palmitic acid (C16:0, 0.02–20.5%), stearic acid (C18:0, 0.42–49.19), oleic acid (C18:1, 0.29–50.09 %), linoleic acid (C18:2, 0.23– 44.91%), eicosapentaenoic acid (EPA, C20:5n3, 0.41– 4.61%) docosahexaenoic acid (DHA, C22:6n3, 0.28– 3.44%). The rest of the microelements, Cd, Hg, and Pb were all present in amounts below toxic levels.

Matched MeSH terms: Myristic Acid
Fulltext A study of fatty acid composition and tocopherol content of lipid extracted from marine microalgae, Nannochloropsis oculata and Tetraselmis suecica, using solvent extraction and supercritical fluid extraction

Bong, S.C., Loh, S. P.

International Food Research Journal, 2013;20(2):721-729.
MyJurnal

This study was conducted to investigate and compare the fatty acids and tocopherols of lipid extracted from marine microalgae, Nannochloropsis oculata (NO) and Tetraselmis suecica (TS) using solvent extraction and supercritical fluid extraction (SFE). Fatty acids and tocopherols were determined in the extracted lipid as functions of the temperature (40, 80oC) and pressure (3000, 5000, 7000, 9000psi). Dichloromethane/methanol and hexane were the chosen conventional solvent for fatty acids and tocopherols extraction respectively. The results obtained showed that there were differences in the fatty acid composition of various lipid extracts of NO and TS. Extracts of NO were high in myristic acid (C14:0) (17-35%), palmitic acid (C16:0) (14-47%) and palmitoleic acid (C16:1) (11-42%) whereas extracts of TS were high in C14:0 (21-34%) and C16:0 (29-49%). Eicosapentaenoic acid (EPA) was detected only under certain SFE conditions in NO but was not detected in TS. α-, β- and γ-tocopherol were detected in various SFE extracts of NO but only α- and β-tocopherol were detected in TS. Hexane extraction of both NO and TS resulted in the detection of only α-tocopherol. In conclusion, the use of different extraction methods resulted in different compositions and concentrations of fatty acids and tocopherols in the microalgae studied.

Matched MeSH terms: Myristic Acid
Structural difference of palm based Medium- and Long-Chain Triacylglycerol (MLCT) further reduces body fat accumulation in DIO C57BL/6J mice when consumed in low fat diet for a mid-term period

Lee YY, Tang TK, Phuah ET, Karim NAA, Alitheen NBM, Tan CP, et al.

Food Res Int, 2018 01;103:200-207.
PMID: 29389606 DOI: 10.1016/j.foodres.2017.10.022

Medium-and-Long Chain Triacylglycerol (MLCT) is a type of structured lipid that is made up of medium chain, MCFA (C8-C12) and long chain, LCFA (C16-C22) fatty acid. Studies claimed that consumption of MLCT has the potential in reducing visceral fat accumulation as compared to long chain triacylglycerol, LCT. This is mainly attributed to the rapid metabolism of MCFA as compared to LCFA. Our study was designed to compare the anti-obesity effects of a enzymatically interesterified MLCT (E-MLCT) with physical blend of palm kernel and palm oil (B-PKOPO) having similar fatty acid composition and a commercial MLCT (C-MLCT) made of rapeseed/soybean oil on Diet Induced Obesity (DIO) C57BL/6J mice for a period of four months in low fat, LF (7%) and high fat, HF (30%) diet. The main aim was to determine if the anti-obesity effect of MLCT was contributed solely by its triacylglycerol structure alone or its fatty acid composition or both. Out of the three types of MLCT, mice fed with Low Fat, LF (7%) E-MLCT had significantly (P<0.05) lower body weight gain (by ~30%), body fat accumulation (by ~37%) and hormone leptin level as compared to both the LF B-PKOPO and LF C-MLCT. Histological examination further revealed that dietary intake of E-MLCT inhibited hepatic lipid accumulation. Besides, analysis of serum profile also demonstrated that consumption of E-MLCT was better in regulating blood glucose compared to B-PKOPO and C-MLCT. Nevertheless, both B-PKO-PO and E-MLCT which contained higher level of myristic acid was found to be hypercholesterolemic compared to C-MLCT. In summary, our finding showed that triacylglycerol structure, fatty acid composition and fat dosage play a pivotal role in regulating visceral fat accumulation. Consumption of E-MLCT in low fat diet led to a significantly lesser body fat accumulation. It was postulated that the MLM/MLL/LMM/MML/LLM types of triacylglycerol and C8-C12 medium chain fatty acids were the main factors that contributed to the visceral fat suppressing effect of MLCT. Despite being able to reduce body fat, the so called healthful functional oil E-MLCT when taken in high amount do resulted in fat accumulation. In summary, E-MLCT when taken in moderation can be used to manage obesity issue. However, consumption of E-MLCT may lead to higher total cholesterol and LDL level.

Matched MeSH terms: Myristic Acid
The chain length of dietary saturated fatty acids affects human postprandial lipemia

Karupaiah T, Tan CH, Chinna K, Sundram K

J Am Coll Nutr, 2011 Dec;30(6):511-21.
PMID: 22331686

OBJECTIVE: Saturated fats increase total cholesterol (TC) and low density lipoprotein-cholesterol (LDL-C) and are linked to coronary artery disease risk. The effect of variance in chain length of saturated fatty acids (SFA) on coronary artery disease in human postprandial lipemia is not well elucidated.
METHODS: A total of 20 healthy volunteers were challenged with 3 test meals, similar in fat content (~31% en) but varying in saturated SFA content and polyunsaturated/saturated fatty acid ratios (P/S). The 3 meals were lauric + myristic acid-rich (LM), P/S 0.19; palmitic acid-rich (POL), P/S 0.31; and stearic acid-rich (STE), P/S 0.22. Blood was sampled at fasted baseline and 2, 4, 5, 6, and 8 hours. Plasma lipids (triacylglycerol [TAG]) and lipoproteins (TC, LDL-C, high density lipoprotein-cholesterol [HDL-C]) were evaluated.
RESULTS: Varying SFA in the test meal significantly impacted postprandial TAG response (p < 0.05). Plasma TAG peaked at 5 hours for STE, 4 hours for POL, and 2 hours for LM test meals. Area-under-the-curve (AUC) for plasma TAG was increased significantly after STE treatment (STE > LM by 32.2%, p = 0.003; STE > POL by 27.9%, p = 0.023) but was not significantly different between POL and LM (POL > LM by 6.0%, p > 0.05). At 2 hours, plasma HDL-C increased significantly after the LM and POL test meals compared with STE (p < 0.05). In comparison to the STE test meal, HDL-C AUC was elevated 14.0% (p = 0.005) and 7.6% (p = 0.023) by the LM and POL test meals, respectively. The TC response was also increased significantly by LM compared with both POL and STE test meals (p < 0.05).
CONCLUSIONS: Chain length of saturates clearly mediated postmeal plasma TAG and HDL-C changes.

Matched MeSH terms: Myristic Acid/administration & dosage
Dietary palmitic and oleic acids exert similar effects on serum cholesterol and lipoprotein profiles in normocholesterolemic men and women

Ng TK, Hayes KC, DeWitt GF, Jegathesan M, Satgunasingam N, Ong AS, et al.

J Am Coll Nutr, 1992 Aug;11(4):383-90.
PMID: 1506599

To compare the effects of dietary palmitic acid (16:0) vs oleic acid (18:1) on serum lipids, lipoproteins, and plasma eicosanoids, 33 normocholesterolemic subjects (20 males, 13 females; ages 22-41 years) were challenged with a coconut oil-rich diet for 4 weeks. Subsequently they were assigned to either a palm olein-rich or olive oil-rich diet followed by a dietary crossover during two consecutive 6-week periods. Each test oil served as the sole cooking oil and contributed 23% of dietary energy or two-thirds of the total daily fat intake. Dietary myristic acid (14:0) and lauric acid (12:0) from coconut oil significantly raised all the serum lipid and lipoprotein parameters measured. Subsequent one-to-one exchange of 7% energy between 16:0 (palm olein diet) and 18:1 (olive oil diet) resulted in identical serum total cholesterol (192, 193 mg/dl), low-density lipoprotein cholesterol (LDL-C) (130, 131 mg/dl), high-density lipoprotein cholesterol (HDL-C) (41, 42 mg/dl), and triglyceride (TG) (108, 106 mg/dl) concentrations. Effects attributed to gender included higher HDL in females and higher TG in males associated with the tendency for higher LDL and LDL/HDL ratios in men. However, both sexes were equally responsive to changes in dietary fat saturation. The results indicate that in healthy, normocholesterolemic humans, dietary 16:0 can be exchanged for 18:1 within the range of these fatty acids normally present in typical diets without affecting the serum lipoprotein cholesterol concentration or distribution. In addition, replacement of 12:0 + 14:0 by 16:0 + 18:1, but especially 16:0 or some component of palm olein, appeared to have a beneficial impact on an important index of thrombogenesis, i.e., the thromboxane/prostacyclin ratio in plasma.

Matched MeSH terms: Myristic Acids/pharmacology; Myristic Acid

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