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International Journal of Molecular... Aug 2023This study aimed to assess the impact of oleic acid (OA) supplementation on the biosynthesis of 10-hydroxy-2-decenoic acid (10-HDA) in . In experiment 1, varying...
This study aimed to assess the impact of oleic acid (OA) supplementation on the biosynthesis of 10-hydroxy-2-decenoic acid (10-HDA) in . In experiment 1, varying concentrations of OA (2%, 4%, 6% and 8%) were added to an artificial diet for newly emerged bees reared in cages. Analysis of 10-HDA content and gene expression in the mandibular gland (MG) revealed that the 8% OA treatment had the greatest impact on promoting the synthesis of 10-HDA. Subsequent investigations utilized RNA-seq and lipidomics to characterize the molecular signature in the MG after feeding the 8% OA diet. Phosphatidylcholine (PC) and triacylglycerol (TAG) were found to be the predominant lipids in the MG of worker bees. A total of 154 TAGs were identified, with TAG (18:1-18:1-18:1) exhibiting the highest abundance, which increased by 1.5 times. The major TAG species contained palmitic acid (16:0) and oleic acid (18:1) in their structure, which was associated with fatty acid composition of diet. The increase in abundance of main TAGs may be attributed to the upregulation of glycerol-3-phosphate acyltransferase (Gpat) and glycerol kinase (GK) gene expression at the transcriptional level. The upregulation of differentially expressed genes (DEGs) related to carbohydrate metabolism may contribute to meeting the heightened metabolic demands of the MGs in worker bees. Royal jelly (RJ) samples from bee colonies fed with the 8% OA diet exhibited higher 10-HDA level than RJ collected from bee colonies fed with the artificial diet. These results indicate that 8% OA addition in the diet enhanced biosynthesis of 10-HDA in the mandibular gland, which was accompanied by significant and highly species-selective remodeling of TAGs.
Topics: Bees; Animals; Oleic Acid; Fatty Acids, Monounsaturated; Glycerol-3-Phosphate O-Acyltransferase; Lecithins; Triglycerides
PubMed: 37686166
DOI: 10.3390/ijms241713361 -
Experimental Biology and Medicine... Jun 2022We herein report the synthesis of poly (9-decenoic acid-1-vinylimidazole--isopropylacrylamide) nanoparticles containing indocyanine green (ICG) in one pot and in water...
We herein report the synthesis of poly (9-decenoic acid-1-vinylimidazole--isopropylacrylamide) nanoparticles containing indocyanine green (ICG) in one pot and in water phase throughout the reaction. We have shown that copolymers of 9-decenoic acid and 1-vinylimidazole, or 9-decenoic acid alone, have an enhanced sensitivity to pH values between 7.4 and 6.8 and are superior to the widely used acrylic acid. We have also shown that incorporation of acidic comonomers leads to the favorable outcome of a higher fluorescence signal intensity in lower pH values, whereas the opposite is true of basic comonomers, where the fluorescence signal intensity is lower at low pH values. It was shown that to keep the pH response favorable the molar ratio of basic comonomers to acidic comonomers should roughly equal 1:4. We controlled the lower critical solution temperature (LCST) of the nanoparticles from around 30 to 38°C for different applications by adding acrylamide comonomers. Finally, the nanoparticles at varying pH values, when imaged by an ultrasound switchable fluorescence (USF) imaging system, showed pH sensitivity and thermosensitivity at physiological and tumor pH.
Topics: Acrylamides; Acrylic Resins; Hydrogen-Ion Concentration; Imidazoles; Nanoparticles; Optical Imaging; Temperature
PubMed: 35470688
DOI: 10.1177/15353702221087648 -
ACS Omega May 202210-Hydroxy-2-decenoic acid (10-HDA) is an α,β-unsaturated medium-chain carboxylic acid containing a terminal hydroxyl group. It has various unique properties and great...
10-Hydroxy-2-decenoic acid (10-HDA) is an α,β-unsaturated medium-chain carboxylic acid containing a terminal hydroxyl group. It has various unique properties and great economic value. We improved the two-step biosynthesis method of 10-HDA. The conversion rate of the intermediate product -2-decenoic acid in the first step of 10-HDA synthesis could reach 93.1 ± 1.3% by combining transporter overexpression and permeation technology strategies. Moreover, the extracellular -2-decenoic acid content was five times greater than the intracellular content when 2.0% (v/v) triton X-100 and 1.2% (v/v) tween-80 were each used. In the second step of 10-HDA synthesis, we regenerated NAD(P)H by overexpressing a glucose dehydrogenase with the P450 enzyme (CYP153A33/M228L-CPR) in , improving the catalytic performance of the -2-decenoic acid terminal hydroxylation. Finally, the yield of 10-HDA was 486.5 mg/L using decanoic acid as the substrate with two-step continuous biosynthesis. Our research provides a simplified production strategy to promote the two-step continuous whole-cell catalytic biosynthesis of 10-HDA and other α,β-unsaturated carboxylic acid derivatives.
PubMed: 35664602
DOI: 10.1021/acsomega.2c00972 -
Scientific Reports May 2021In bees from genus Melipona, differential feeding is not enough to fully explain female polyphenism. In these bees, there is a hypothesis that in addition to the...
In bees from genus Melipona, differential feeding is not enough to fully explain female polyphenism. In these bees, there is a hypothesis that in addition to the environmental component (food), a genetic component is also involved in caste differentiation. This mechanism has not yet been fully elucidated and may involve epigenetic and metabolic regulation. Here, we verified that the genes encoding histone deacetylases HDAC1 and HDAC4 and histone acetyltransferase KAT2A were expressed at all stages of Melipona scutellaris, with fluctuations between developmental stages and castes. In larvae, the HDAC genes showed the same profile of Juvenile Hormone titers-previous reported-whereas the HAT gene exhibited the opposite profile. We also investigated the larvae and larval food metabolomes, but we did not identify the putative queen-fate inducing compounds, geraniol and 10-hydroxy-2E-decenoic acid (10HDA). Finally, we demonstrated that the histone deacetylase inhibitor 10HDA-the major lipid component of royal jelly and hence a putative regulator of honeybee caste differentiation-was unable to promote differentiation in queens in Melipona scutellaris. Our results suggest that epigenetic and hormonal regulations may act synergistically to drive caste differentiation in Melipona and that 10HDA is not a caste-differentiation factor in Melipona scutellaris.
Topics: Acyclic Monoterpenes; Animals; Bees; Epigenesis, Genetic; Fatty Acids; Fatty Acids, Monounsaturated; Feeding Behavior; Female; Gene Expression Regulation, Developmental; Hierarchy, Social; Histone Acetyltransferases; Histone Deacetylases; Insect Proteins; Juvenile Hormones
PubMed: 33972627
DOI: 10.1038/s41598-021-89212-5 -
Evidence-based Complementary and... 2022Natural products and their derivatives as an inexpensive, accessible, and useful alternative medicine are broadly applied for the treatment of a wide range of diseases...
Insecticidal, Antimalarial, and Antileishmanial Effects of Royal Jelly and Its Three Main Fatty Acids, -10-Hydroxy-2-decenoic Acid, 10-Hydroxydecanoic Acid, and Sebacic Acid.
Natural products and their derivatives as an inexpensive, accessible, and useful alternative medicine are broadly applied for the treatment of a wide range of diseases and infectious ones. The present study was designed to evaluate the insecticidal, antimalarial, antileishmanial, and cytotoxic effects of royal jelly and its three main fatty acids (-10-hydroxy-2-decenoic acid (10-H2DA), 10-hydroxydecanoic acid (10-HDAA), sebacic acid (1,10-decanedioic acid)). Insecticidal activity of RJ and 10-H2DA, 10-HDAA, and sebacic acid was performed against healthy 4th instar larvae at 25 ± 2°C. Antiplasmodial and antileishmanial effects of RJ and 10-H2DA, 10-HDAA, and sebacic acid were also performed against chloroquine-resistant K1-strain and amastigotes according to the Malstat method and macrophage model, respectively. In addition, the level of nitric oxide (NO) production in J774-A1 macrophages cells, plasma membrane permeability, and caspase-3-like activity and cytotoxicity effects of RJ and 10-H2DA, 10-HDAA, and sebacic acid against human embryonic kidney 293 (HEK239T cells) were evaluated. Considering the insecticidal activity, the results showed that the lethal concentration 50% value for RJ, 10-H2DA, 10-HDAA, and sebacic acid was 24.6, 31.4, 37.8, and 44.7 g/mL g/mL, respectively. RJ, 10-H2DA, 10-HDAA, and sebacic acid showed potent ( < 0.0001) antileishmanial effects with IC values ranging from 2.4 to 8.4 g/mL. Various concentrations of RJ, 10-H2DA, 10-HDAA, and sebacic acid significantly ( < 0.05) increased the production of NO, plasma membrane permeability, and caspase-3-like activity level as a dose-dependent response. Considering the cytotoxicity, SIs > 10 of these compounds exhibited their specificity to parasites and safety against human HEK239T normal cells. The results of the present investigation revealed the promising insecticidal, antimalarial, and antileishmanial effects of RJ and its three main fatty acids (10-H2DA, 10-HDAA, and sebacic acid). However, more studies are required to confirm the mechanisms of action mode of these compounds as well as their efficacy in animal models and clinical settings.
PubMed: 35096117
DOI: 10.1155/2022/7425322 -
Molecular Nutrition & Food Research Jun 2022The objective of this study is to explore the effects of 10-hydroxy-2-decenoic acid (10-HDA), the major fatty acid in royal jelly, on dextran sodium sulfate...
Trans-10-Hydroxy-2-Decenoic Acid Alleviates Dextran Sulfate Sodium-Induced Colitis in Mice via Regulating the Inflammasome-Mediated Pyroptotic Pathway and Enhancing Colonic Barrier Function.
SCOPE
The objective of this study is to explore the effects of 10-hydroxy-2-decenoic acid (10-HDA), the major fatty acid in royal jelly, on dextran sodium sulfate (DSS)-induced mice ulcerative colitis (UC) and its potential mechanism of action.
METHODS AND RESULTS
Forty male C57BL/6 mice are randomly divided into five experimental groups: control, DSS, DSS + 25 (or 100)mg kg d 10-HDA, and DSS + 200 mg kg d mesalazine (ME). UC is induced in mice using 2.5% DSS in drinking water for 7 days. During the induction, these UC mice are orally administrated 10-HDA or ME per day. Meanwhile, lipopolysaccharide (LPS)/adenosine-triphosphate (ATP)-stimulated THP1 cells are used as a model to test the effects of 10-HDA. 10-HDA reduces DSS-induced pathological damage, reactive oxygen species (ROS) accumulation, neutrophil infiltration, and cytokine production in colonic tissue. Compared with the DSS group, the expressions of thioredoxin interacting protein (TXNIP), NOD-like receptor family pyrin domain containing 3 (NLRP3), apoptosis-associated speck-like protein containing a caspase-recruitment domain (ASC), cysteinyl aspartate specific proteinase-1 (Caspase-1), gasdermin-D (GSDMD), N-terminal domain of gasdermin-D (N-GSDMD), interleukin-1β (IL-1β), and interleukin-18 (IL-18) in the colon are decreased after administration of 10-HDA. 10-HDA also elevates the barrier integrity and the expressions of zonula occludens-1 (ZO-1) and Occludin in colonic epithelium exposed to DSS. In THP1 cells, the inflammasome-mediated pyroptosis induced by LPS/ATP is inhibited by 10-HDA pretreatment.
CONCLUSION
10-HDA alleviates DSS-induced colitis by regulating the NLRP3 inflammasome-mediated pyroptotic pathway and enhancing colonic barrier function.
Topics: Adenosine Triphosphate; Animals; Caspase 1; Colitis; Colitis, Ulcerative; Dextran Sulfate; Fatty Acids, Monounsaturated; Inflammasomes; Lipopolysaccharides; Male; Mice; Mice, Inbred C57BL; NLR Family, Pyrin Domain-Containing 3 Protein
PubMed: 35373915
DOI: 10.1002/mnfr.202100821 -
European Journal of Nutrition Oct 2020Neuroinflammation is thought to be associated with the pathogenesis of a series of neurodegenerative diseases. We have previously reported that royal jelly (RJ) has an...
PURPOSE
Neuroinflammation is thought to be associated with the pathogenesis of a series of neurodegenerative diseases. We have previously reported that royal jelly (RJ) has an anti-inflammatory effect on microglial BV-2 cells. However, components contributing to the effect of RJ were largely unexplored. The aim of this study was to assess whether trans-10-hydroxy-2-decenoic acid (10-HDA), the exclusive fatty acid in RJ, can alleviate neuroinflammation and to further explore the underlying mechanisms.
METHODS
Immunohistochemistry staining, ELISA, qRT-PCR and Western blot were used to assess the effect of 10-HDA on LPS-induced neuroinflammation both in vivo and in vitro. To determine the extent of inflammatory changes after 10-HDA treatment, RNAseq transcriptomic analysis was conducted.
RESULTS
10-HDA pretreatment significantly reduced the production of pro-inflammatory mediators in LPS-treated C57BL/6J mice and microglial BV-2 cells. 10-HDA inhibited the activation of the TNF-α/NF-κB axis and NLRP3 inflammasome-IL-1β pathway, which may be the anti-neuroinflammatory mechanism of 10-HDA. We also demonstrated that 10-HDA triggered cell autophagy, as evidenced by elevated levels of microtubule-associated protein 1 light chain 3-II (LC3-II) and decreased expression of SQSTM1. More importantly, 10-HDA increased the transcriptional activity of FOXO1 by increasing FOXO1 nuclear localization. Inhibition of FOXO1 and autophagy using chemical inhibitors markedly blunted the effect of 10-HDA on the TNF-α pathway and NLRP3 inflammasome-IL-1β pathway, indicating that 10-HDA alleviates neuroinflammation in BV-2 cells by modulating FOXO1-mediated autophagy.
CONCLUSIONS
10-HDA may be a promising agent for various neuroinflammation-associated diseases.
Topics: Animals; Autophagy; Fatty Acids, Monounsaturated; Forkhead Box Protein O1; Lipopolysaccharides; Mice; Mice, Inbred C57BL; Microglia; NF-kappa B; Signal Transduction
PubMed: 31820078
DOI: 10.1007/s00394-019-02128-9 -
Pharmaceutics Oct 2023Wound dressings serve to protect tissue from contamination, alleviate pain, and facilitate wound healing. The biopolymer chitosan is an exemplary choice in wound...
Wound dressings serve to protect tissue from contamination, alleviate pain, and facilitate wound healing. The biopolymer chitosan is an exemplary choice in wound dressing material as it is biocompatible and has intrinsic antibacterial properties. Infection can be further prevented by loading dressings with cis-2-decenoic acid (C2DA), a non-antibiotic antimicrobial agent, as well as bupivacaine (BUP), a local anesthetic that also has antibacterial capabilities. This study utilized a series of assays to elucidate the responses of dermal cells to decanoic anhydride-modified electrospun chitosan membranes (DA-ESCMs) loaded with C2DA and/or BUP. Cytocompatibility studies determined the toxic loading ranges for C2DA, BUP, and combinations, revealing that higher concentrations (0.3 mg of C2DA and 1.0 mg of BUP) significantly decreased the viability of fibroblasts and keratinocytes. These high concentrations also inhibited collagen production by fibroblasts, with lower loading concentrations promoting collagen deposition. These findings provide insight into preliminary cellular responses to DA-ESCMs and can guide future research on their clinical application as wound dressings.
PubMed: 37896236
DOI: 10.3390/pharmaceutics15102476 -
Journal of Clinical Medicine Aug 2023Although previous studies have demonstrated that royal jelly (RJ) may have estrogenic properties and prevent postmenopausal bone loss, the underlying mechanisms are not...
Although previous studies have demonstrated that royal jelly (RJ) may have estrogenic properties and prevent postmenopausal bone loss, the underlying mechanisms are not fully understood. This animal study aimed to investigate the effects of specific fatty acids of RJ, 10-hydroxy-2-decenoic acid (10H2DA) and 10-hydroxydecanoic acid (10HDAA), in ovariectomized rats. Ten-week-old female Wistar rats were divided into the Baseline, Sham, Ovx, Ovx + 10H2DA, and Ovx + 10HDAA groups. Rats in the Baseline group were sacrificed immediately, whereas those in the other groups were subjected to either a sham operation or bilateral ovariectomy. The animals in the Ovx + 10H2DA and Ovx + 10HDAA groups were fed diets containing 10H2DA and 10HDAA, respectively. Twelve weeks after surgery, the rats were sacrificed, and indices of bone mass and bone mechanics were analyzed. Femoral bone mineral density was significantly lower in the Ovx group than in the Sham group ( < 0.01). Administration of 10H2DA or 10HDAA did not ameliorate bone loss after ovariectomy. In addition, administration of these fatty acids diminished femur bone stiffness in ovariectomized rats ( < 0.01 and < 0.05, respectively). These findings suggest that the favorable effects of RJ may not be exerted solely by 10H2DA or 10HDAA. However, these effects may be exhibited in combination with other RJ constituents.
PubMed: 37629354
DOI: 10.3390/jcm12165309 -
Frontiers in Microbiology 2023This study aimed to investigated the effects of 10-hydroxy-2-decenoic acid (10-HDA) on the growth performance, intestinal barrier, inflammatory response, oxidative...
10-hydroxy-2-decenoic acid alleviates lipopolysaccharide-induced intestinal mucosal injury through anti-inflammatory, antioxidant, and gut microbiota modulation activities in chickens.
INTRODUCTION
This study aimed to investigated the effects of 10-hydroxy-2-decenoic acid (10-HDA) on the growth performance, intestinal barrier, inflammatory response, oxidative stress, and gut microbiota of chickens challenged with lipopolysaccharide (LPS).
METHODS
A total of 240 one-day-old chickens were randomly assigned to five treatment groups: (1) control group (basal diet + saline); (2) LPS group (basal diet + LPS); (3) Chlortetracycline (CTC) group (basal diet containing 75 mg/kg CTC + LPS); (4) 0.1% 10-HDA group (basal diet containing 1 g/kg 10-HDA + LPS); and (5) 0.5% 10-HDA group (basal diet containing 5 g/kg 10-HDA + LPS). All chickens were injected intraperitoneally with 0.5 mg/kg body weight of either LPS or saline at 17, 19, and 21 days of age.
RESULTS
The results showed that dietary 10-HDA supplementation attenuated the loss in growth performance caused by the LPS challenge ( < 0.05). 10-HDA effectively alleviated LPS-induced intestinal mucosal injury, as evidenced by reduced bleeding, decreased serum diamine oxidase levels ( < 0.05), and increased villus/crypt ratios of the jejunum and ileum ( < 0.05). Dietary treatment with 0.1% 10-HDA reduced the concentrations of inflammatory cytokines (TNF-α, IL-1β, IL-6; < 0.05), and increased immunoglobulin (IgA, IgG) and antioxidant enzyme levels (CAT, GSH-px, T-SOD) in the serum of LPS-challenged chickens ( < 0.05). These effects were similar to those observed in the CTC group. Moreover, 0.1% 10-HDA treatment reversed the LPS-induced variations in the mRNA expression of genes related to inflammation, antioxidant capacity, and intestinal tight junctions ( < 0.05). 16S rRNA analysis revealed that 10-HDA supplementation increased the relative abundance of and ( < 0.05). Additionally, it decreased the abundance of , , and ( < 0.05). These changes were correlated with reduced inflammation and improved antioxidant capacity in the LPS-challenged chickens.
CONCLUSION
Collectively, dietary 10-HDA supplementation alleviated LPS-induced intestinal mucosal injury and the loss of growth performance through anti-inflammatory, antioxidant, and gut microbiota modulation activities in chickens. Moreover, 0.1% 10-HDA supplementation had comparable or even better protection for LPS-challenged chickens than supplementation with antibiotics or 0.5% 10-HDA. 10-HDA has the potential to be used as an alternative to antibiotics in protecting the intestinal health and improving the performance of poultry.
PubMed: 37915852
DOI: 10.3389/fmicb.2023.1285299