2-decenoic Acid Research Articles

The role of 10-hydroxy-Δ<sup>2</sup>-decenoic acid in the formation of fibrils of the major royal jelly protein 1/apisimin/24-methylenecholesterol complex isolated from honey bee (Apis mellifera) royal jelly

Queen larvae of the honey bee (Apis mellifera) are fed with royal jelly, a glandular secretion produced by the hypopharyngeal and mandibular glands of worker honey bees. The necessary consistency of royal jelly is dependent on a protein-sterol complex (MRJP14/apisimin4/24MC8). At low pH, this complex forms fibrillar structures, which increase the viscosity of royal jelly. While the proteins in this complex are produced in the hypopharyngeal gland, the low pH is achieved by the secretion of the mandibular gland, which contains fatty acids. It is shown for the first time that fibril formation of MRJP14/apisimin4/24MC8 is not only induced by low pH via a buffer system, but also by the addition of the major fatty acid 10-hydroxy-Δ2-decenoic acid (10-HDA) of the mandibular gland secretion. This result further substantiates that fibril formation of the MRJP14/apisimin4/24MC8 complex only occurs after mixing the hypopharyngeal and mandibular gland secretions.

Synthesis and Characterization of 2-Decenoic Acid Modified Chitosan for Infection Prevention and Tissue Engineering.

Chitosan nanofiber membranes are recognized as functional antimicrobial materials, as they can effectively provide a barrier that guides tissue growth and supports healing. Methods to stabilize nanofibers in aqueous solutions include acylation with fatty acids. Modification with fatty acids that also have antimicrobial and biofilm-resistant properties may be particularly beneficial in tissue regeneration applications. This study investigated the ability to customize the fatty acid attachment by acyl chlorides to include antimicrobial 2-decenoic acid. Synthesis of 2-decenoyl chloride was followed by acylation of electrospun chitosan membranes in pyridine. Physicochemical properties were characterized through scanning electron microscopy, FTIR, contact angle, and thermogravimetric analysis. The ability of membranes to resist biofilm formation by S. aureus and P. aeruginosa was evaluated by direct inoculation. Cytocompatibility was evaluated by adding membranes to cultures of NIH3T3 fibroblast cells. Acylation with chlorides stabilized nanofibers in aqueous media without significant swelling of fibers and increased hydrophobicity of the membranes. Acyl-modified membranes reduced both S. aureus and P. aeruginosa bacterial biofilm formation on membrane while also supporting fibroblast growth. Acylated chitosan membranes may be useful as wound dressings, guided regeneration scaffolds, local drug delivery, or filtration.

Chemical Characterization and Biological Properties of Royal Jelly Samples From the Mediterranean Area

Royal jelly (RJ) is a bee product that has high nutritional value and is beneficial for the human health, earning importance as a functional food. Thus, the characterization of its main biological properties is with high importance. In this work, 6 RJ samples obtained in Morocco, Portugal, and Spain were evaluated in terms of total phenol and flavone/flavonol contents; total protein; 10-hydroxy-2-decenoic acid (10-HDA); volatiles composition; antioxidant and anti-inflammatory properties; and inhibition of tyrosinase, xanthine oxidase (XO), and acetylcholinesterase (AChE) activities. Total phenolic content ranged from 3 to 9 mg gallic acid equivalent/g RJ, and flavone/flavonol content from 0.1 to 0.5 mg quercetin equivalent/g RJ. 10-Hydroxy-2-decenoic acid content varied from 0.9% to 1.2% and total protein from 5.5% to 29.7%. Gas chromatography-flame ionization detector and gas chromatography-mass spectrometry analysis showed RJ volatiles dominated by linolenic acid, 2-decenoic acid, and octanoic acid in variable amounts. The antioxidant activity was monitored through nitric oxide (NO) scavenging activity and hydrogen peroxide (H2O2) scavenging capacity, where the IC50 ranged from 2.3 to 3.4 and 0.2 to 1.5 mg/mL, respectively. Anti-AChE activity IC50 ranged from 0.7 to 4.6 mg/mL, while XO inhibition IC50 ranged from 3.3 to 11.9 mg/mL. The results showed that phenols and flavonoids highly contributed to the RJ biological properties in contrast to 10-HDA and proteins.

Sulfated liposaccharides inspired by telomerase inhibitor axinelloside A

Sulfated liposaccharides are known inhibitors of telomerase and here we describe the synthesis of a series of sulfated liposaccharides inspired by the natural product axinelloside A, reported to act as an inhibitor of human telomerase. We established a robust and scalable synthetic route to galactosyl liposaccharides capitalizing on a series of regioselective acylation reactions with 2-decenoic acid and imidazolium sulfate esters.

Engineering Escherichia coli for the synthesis of short- and medium-chain α,β-unsaturated carboxylic acids

Concerns over sustained availability of fossil resources along with environmental impact of their use have stimulated the development of alternative methods for fuel and chemical production from renewable resources. In this work, we present a new approach to produce α,β-unsaturated carboxylic acids (α,β-UCAs) using an engineered reversal of the β-oxidation (r-BOX) cycle. To increase the availability of both acyl-CoAs and enoyl-CoAs for α,β-UCA production, we use an engineered Escherichia coli strain devoid of mixed-acid fermentation pathways and known thioesterases. Core genes for r-BOX such as thiolase, hydroxyacyl-CoA dehydrogenase, enoyl-CoA hydratase, and enoyl-CoA reductase were chromosomally overexpressed under the control of a cumate inducible phage promoter. Native E. coli thioesterase YdiI was used as the cycle-terminating enzyme, as it was found to have not only the ability to convert trans-enoyl-CoAs to the corresponding α,β-UCAs, but also a very low catalytic efficiency on acetyl-CoA, the primer and extender unit for the r-BOX pathway. Coupling of r-BOX with YdiI led to crotonic acid production at titers reaching 1.5g/L in flask cultures and 3.2g/L in a controlled bioreactor. The engineered r-BOX pathway was also used to achieve for the first time the production of 2-hexenoic acid, 2-octenoic acid, and 2-decenoic acid at a final titer of 0.2g/L. The superior nature of the engineered pathway was further validated through the use of in silico metabolic flux analysis, which showed the ability of r-BOX to support growth-coupled production of α,β-UCAs with a higher ATP efficiency than the widely used fatty acid biosynthesis pathway. Taken together, our findings suggest that r-BOX could be an ideal platform to implement the biological production of α,β-UCAs.

Measuring and modeling elution of Cis 2-decenoic acid from phosphatidylcholine coatings

Measuring and modeling elution of Cis 2-decenoic acid from phosphatidylcholine coatings

A suggestion for royal jelly specifications.

This article proposes guidelines for quality standards of royal jelly. The proposals are based on two sets of data; the first from our study of the factors that may affect the royal jelly's chemical composition (protein and sugar supplementation of beehives) and the second on the analysis of a great number of samples from across Greece to establish natural variability of this product. We compared our findings with the adopted national limits, the proposals of the working group of the International Honey Commission (IHC), and the draft proposal of the International Organization of Standardization (ISO). The studied parameters included moisture, total proteins, sugars (fructose, glucose, sucrose, total sugars), and 10-hydroxy- 2-decenoic acid (10-HDA). Our results indicate that the limits for royal jelly in some countries should be amended and the proposals of the IHC and the ISO reviewed in view of recent data on variability. We believe that our proposals could be considered for setting global standards for royal jelly, as they incorporate national legislations, proposals of scientific groups, experimental data, and updated information.

Basic Research on Neurotrophic Factors and Its Application to Medical Uses

The author has studied nerve growth factor (NGF) and its family of neurotrophic factors (neurotrophins) for over 40 years. During the first 20 years, my laboratory established a highly sensitive enzyme immunoassay for NGF and analyzed the regulatory mechanism of NGF synthesis in cultured primary cells. Fibroblast cells cultured from peripheral organs such as the heart and astrocytes from the brain produced a substantial amount of NGF in a growth-dependent manner. Furthermore, synthesis of NGF in these cells could be upregulated by catechol compounds including catecholamines. This observation might explain a physiological relation between the level of NGF mRNA and the density of innervation in the peripheral sympathetic nervous systems. Over the subsequent 20 years, my laboratory investigated the physiological functions of neurotrophic factors, including neurotrophins, during development or post-injury and found that brain-derived neurotrophic factor (BDNF) plays a role in the formation of the laminar structure of the cerebral cortex. In addition, my laboratory discovered that endogenous glial cell line-derived neurotrophic factor (GDNF) contributes to the amelioration of motor activity after spinal cord injury. Therefore we aimed to develop low-molecular weight compounds that generate neurotrophic factor-like intracellular signals to protect or ameliorate neurological/psychiatric diseases. 2-Decenoic acid derivatives and other similar molecules could protect or ameliorate in animal models of mood disorders such as depression and enhance recovery from spinal cord injury-induced motor paralysis. Compounds that can generate neurotrophin-like signals in neurons are expected to be developed as therapeutic drugs for certain neurological or psychiatric disorders.

CORR Insights(®): D-amino acid inhibits biofilm but not new bone formation in an ovine model.

C omplex musculoskeletal injuries are complicated by infections in as many 30% of traumatized patients [2], depending on the type of injury and the timing of the interventions. Biomaterials often are necessary components to restore function and promote healing in injuries where muscle, nerve, and bone damage present challenges to healing. While biomaterials serve critical functions in repairing defects, they also increase the risk of infection. This is in part due to the promotion of biofilm formation on the surface of implants, and in particular, the presence of persister cells (dormant cells that survive exposure to antimicrobials) within biofilm. Biofilm microorganisms and persister cells have altered metabolic function that make them resistant to traditional antibiotic therapy and require antimicrobial concentrations several orders of magnitude higher for complete eradication than those necessary for killing planktonic counterparts [9]. Basic science studies of biofilm and persister-cell biology have led to the discovery of a number of molecules that specifically target these phenotypes. D-amino acids (D-AAs), cis 2decenoic acid, and farnesol are among these recently discovered biofilm inhibitors that have been shown to prevent biofilm formation, disperse existing biofilm, and revert persister cells to a more active and antimicrobial-susceptible state [4, 7, 8]. While in vitro results using D-AAs are encouraging, clinical use of these biofilm inhibitors remains investigational. Dose considerations and compatibility with bone and soft tissue must be established for safety. Since systemic delivery of D-AAs and other biofilm inhibitors may be ineffective, local delivery carriers for D-AAs are an advantageous strategy for clinical use.

A novel 2-decenoic acid thioester ameliorates corticosterone-induced depression- and anxiety-like behaviors and normalizes reduced hippocampal signal transduction in treated mice.

We characterized mice administered corticosterone (CORT) at a dose of 20 mg/kg for 3 weeks to determine their suitability as a model of mood disorders and found that the time immobilized in the tail suspension test was longer and the time spent in the open arms of the elevated plus-maze test was shorter than those of the vehicle-treated group, findings demonstrating that chronic CORT induced both depression-like and anxiety-like behaviors. Furthermore, the levels of phosphorylated extracellular signal-regulated kinase (pERK) 1/2 in the hippocampus and cerebral cortex were reduced in the CORT-treated group. Using this model, we investigated the protective effect of the ester, thioester, and amide compounds of 2-decenoic acid derivatives (termed compounds A, B, and C, respectively). The potency of the protective activity against the CORT-induced depression-like or anxiety-like behaviors and the reduction in pERK1/2 level were found to be in the following order: compound B > compound C > compound A. Therefore, we further investigated the therapeutic activity of only compound B, and its effect on depression-like behavior was observed after oral administration for 1 or 2 weeks, and its effect on anxiety-like behavior was observed after oral administration for 3 weeks. The ratios of phosphorylated ERK1/2, Akt, and cAMP-response element-binding protein to their respective nonphosphorylated forms were smaller in the CORT-treated group than in the vehicle-treated group; however, subsequent treatment with compound B at either 0.3 or 1.5 mg/kg significantly ameliorated this reduction. Compound B appeared to elicit intracellular signaling, similar to that elicited by brain-derived neurotrophic factor, and its mode of action was shown to be novel and different from that of fluvoxamine, a currently prescribed drug for mood disorders.

Disintegration of aerobic granules induced by trans-2-decenoic acid

One current major hurdle to practical implementation of aerobic granule technology is the frequent occurrence of granule disintegration during long-term operation. However, the mechanism behind this is largely unclear today. Here, 2-decenoic acid, which has been previously demonstrated to be released by Pseudomonas aeruginosa and disperse biofilms, was found to also induce the disintegration of aerobic granules. A comparison of the solution compositions from samples of only trans-2-decenoic acid, only aerobic granules, and granules added with trans-2-decenoic acid shows that bacteria and extracellular polymeric substances (EPS) were stripped from granule surface upon trans-2-decenoic acid dosing. Due to the possible toxicity of trans-2-decenoic acid at a saturation concentration, the disintegrated granules and the milky suspension in the disintegration test showed a significantly lower oxygen uptake rate than the un-integrated granules. This work suggests that trans-2-decenoic acid released by microbes might play a critical role in regulating the disintegration of aerobic granules.

Phytochemistry, pharmacology and medicinal properties of Coriandrum sativum L.

Coriandrum sativum L. commonly known as “Coriander” is an annual herb, indicated for a number of medical properties in traditional medicine. For a long time, C. sativum has been used in traditional medicines as an anti-inflammatory, analgesic, and antibacterial agent. Its essential oil is also used as a natural fragrance with some medicinal properties. C. sativum has recently been shown to have antioxidant, antidiabetic, hepatoprotective, antibacterial, and antifungal activities. Volatile components, flavonoids, and isocoumarins are the main constituents of C. sativum. 2-decenoic acid, E-11-tetradecenoic acid, and capric acid were identified as the major components for C. sativum leaves essential oil. The seed oil contained linalool and geranyl acetate. Due to the easy collection of the plant and being widespread and also remarkable biological activities, this plant has become both food and medicine in many parts of the world. This review presents comprehensive analyzed information on the botanical, chemical, and pharmacological aspects of C. sativum. Key words: Coriandrum sativum, apiaceae, phytochemistry, pharmacology.

2-Decenoic Acid Ethyl Ester, a Compound That Elicits Neurotrophin-like Intracellular Signals, Facilitating Functional Recovery from Cerebral Infarction in Mice

In our previous study, we found that trans-2-decenoic acid ethyl ester (DAEE), a derivative of a medium-chain fatty acid, elicits neurotrophin-like signals including the activation of extracellular signal-regulated kinases 1 and 2 (ERK1/2) in cultured mouse cortical neurons. Here, we examined the efficacy of intraperitoneal administration of DAEE on the treatment of a mouse model of the cerebral infarction caused by unilateral permanent middle cerebral artery occlusion (PMCAO). DAEE-treatment (100 μg/kg body weight injected at 0.5, 24, 48, 72 h after PMCAO) significantly restored the mice from PMCAO-induced neurological deficits including motor paralysis when evaluated 48, 72, and 96 h after the PMCAO. Furthermore, DAEE facilitated the phosphorylation of ERK1/2 on the infarction side of the brain when analyzed by Western immunoblot analysis, and it enhanced the number of phosphorylated ERK1/2-positive cells in the border areas between the infarction and non-infarction regions of the cerebral cortex, as estimated immunohistochemically. As the infarct volume remained unchanged after DAEE-treatment, it is more likely that DAEE improved the neurological condition through enhanced neuronal functions of the remaining neurons in the damaged areas rather than by maintaining neuronal survival. These results suggest that DAEE has a neuro-protective effect on cerebral infarction.

Utilization of 2-alkenoic acids for biosynthesis of medium-chain-length polyhydroxyalkanoates in metabolically engineered Escherichia coli to construct a novel chemical recycling system

This study describes the biosynthesis and thermal degradation of medium-chain-length polyhydroxyalkanoate (PHA), focusing on 2-alkenoic acids as a recyclable carbon source. Using metabolically engineered Escherichia coli, PHA consisting of 3-hydroxydecanoate (3HD) was synthesized from 2-decenoic acid. Solvent cast film of poly(3HD) [P(3HD)] was transparent and showed thermal property similar to that of polycaprolactone. In addition, the use of various 2-alkenoic acids (C6-C12) resulted in production of PHAs with over 95 mol% of the corresponding single monomer units. The pyrolysis product of P(3HD) was dominantly 2-decenoic acid used for the P(3HD) biosynthesis. This demonstrates the feasibility of PHA recycling via 2-alkenoic acids, which act as pyrolysis products and raw materials for PHA biosynthesis.

Vibrational analysis and electronic properties of 2-Decenoic acid and its derivative by first principles

Royal jelly is the mixture of acids like 2-Decenoic acid (DA), 10-Hydroxy 2-Decenoic acid and many others. 10-HDA possesses strong inhibition to the growth of cancer cells, namely transferable AKR leukaemia, TA3 breast cancer, etc. The equilibrium geometry of 2-Decenoic acid and its derivative 10-Hydroxy 2-Decenoic acid in the ground state have been determined and analyzed by Density functional theory (DFT) employing 6-311 G (d, p) as the basis set. The harmonic frequencies of 2-DA and 10-HDA have also been calculated to understand its complete vibrational dynamics. The study of simulated spectra provides important information about the ability of the computational method to describe the vibrational modes.

Vibrational analysis and electronic properties of 2-Decenoic acid and its derivative by first principles

Royal jelly is the mixture of acids like 2-Decenoic acid (DA), 10-Hydroxy 2-Decenoic acid and many others. 10-HDA possesses strong inhibition to the growth of cancer cells, namely transferable AKR leukaemia, TA3 breast cancer, etc. The equilibrium geometry of 2-Decenoic acid and its derivative 10-Hydroxy 2-Decenoic acid in the ground state have been determined and analyzed by Density functional theory (DFT) employing 6-311 G (d, p) as the basis set. The harmonic frequencies of 2-DA and 10-HDA have also been calculated to understand its complete vibrational dynamics. The study of simulated spectra provides important information about the ability of the computational method to describe the vibrational modes.

2-Decenoic acid ethyl ester, a derivative of unsaturated medium-chain fatty acids, facilitates functional recovery of locomotor activity after spinal cord injury

There is increasing evidence that omega-3 polyunsaturated fatty acids (PUFAs) have therapeutic potential in various animal models of neuronal injury. However, very few studies have examined the effect of medium-chain fatty acids (MCFAs) on neuronal injury. So in the present study we synthesized various MCFAs and their derivatives, and found that exposure to trans-2-decenoic acid ethyl ester (DAEE) markedly activated extracellular signal-regulated protein kinases 1 and 2 (ERK1/2) in cultured cortical neurons. Therefore, we examined the effect of DAEE treatment on a rat model of spinal cord injury. DAEE (150 μg/kg body weight) administered after hemisection of the spinal cord resulted in improved functional recovery, decreased the lesion size, increased the activation of ERK1/2, and enhanced the expression of bcl-2 and brain-derived neurotrophic factor (BDNF) mRNA in the injury site of the spinal cord. Furthermore, it also increased neuronal survival after spinal cord injury. These results indicate that the possibility that DAEE will become a promising tool for reducing the secondary damage observed following primary physical injury to the spinal cord.

2-Decenoic acid ethyl ester possesses neurotrophin-like activities to facilitate intracellular signals and increase synapse-specific proteins in neurons cultured from embryonic rat brain

We presently found that medium-chain fatty acids (MCFAs) with 8-12 carbons and their esters facilitated activation (phosphorylation) of mitogen-activated protein kinases (MAPK)/extracellular signal-regulated kinases (ERK) 1/2 of cultured embryonic cortical/hippocampal neurons. In particular, trans-2-decenoic acid ethyl ester (DAEE) had the most potent activity. Additionally, DAEE activated phosphatidylinositol 3-kinase and cAMP-response element binding protein (CREB), suggesting that DAEE generates similar intracellular signal as neurotrophins. Therefore, details of the signal elicited by DAEE were examined in comparison with those of a neurotrophin, brain-derived neurotrophic factor (BDNF). We found that 1) DAEE phosphorylated MAPK/ERK1/2 via MEK activation without the involvement of tyrosine kinases of neurotrophin Trk receptors; 2) DAEE activated CREB predominantly through MAPK/ERK1/2 activation, not through other pathways such as cAMP/protein kinase A; and 3) DAEE increased the expression of RNAs of BDNF and neurotrophin-3 and the protein content of synapse-specific proteins such as synaptophysin, synapsin-1, and syntaxin. Based on these observations we propose that DAEE and some other derivatives of MCFAs having neurotrophin-like neurotrophic activities may become therapeutic tools for certain neurological or psychiatric disorders.

Chemical composition of leaf and seed essential oil of Coriandrum sativum L. from Bangladesh

The essential oils from leaves and fruits of Coriandrum sativum L. were analyzed by gas chromatography mass spectroscopy (GC-MS). The leaf oil contained 44 compounds mostly of aromatic acids containing 2-decenoic acid (30.8%), E-11-tetradecenoic acid (13.4%), capric acid (12.7%), undecyl alcohol (6.4%), tridecanoic acid (5.5%) and undecanoic acid (7.1%) as major constituents. The seed oil contains 53 compounds where the major compounds are linalool (37.7%), geranyl acetate (17.6%) and γ-terpinene (14.4%). The compositions of both oils varied qualitatively and quantitatively. Article Info

OCCURRENCE OF LOROXANTHIN, LOROXANTHIN DECENOATE, AND LOROXANTHIN DODECENOATE IN TETRASELMIS SPECIES (PRASINOPHYCEAE, CHLOROPHYTA)(1).

The pigment composition of six species of Tetraselmis (Prasinophyceae) was analyzed using improved HPLC methods. All pigment extracts showed three peaks corresponding to unknown carotenoids. The isolated pigments were analyzed using UV-Vis spectroscopy, electrospray ionization-mass spectrometry (ESI-MS), and when carotenoid esters were suspected, gas chromatography-mass spectrometry (GC-MS) of the methyl ester and dimethyloxazoline derivative of the corresponding fatty acid. The new pigments were determined to be loroxanthin, loroxanthin 19-(2-decenoate), and loroxanthin 19-(2-dodecenoate); this is the first time these pigments have been described in the genus Tetraselmis. Moreover, this is the first report of esterification of 2-decenoic acid to loroxanthin. The relative contents of these pigments depended on the light regime, with the lowest proportions measured at the highest photon flux density assayed. The implications of the identification of these pigments in the genus Tetraselmis for the pigment types previously described in the class Prasinophyceae are discussed.