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  1. Xu YJ, Wu XH, Tan BK, Lai YH, Vittal JJ, Imiyabir Z, et al.
    J Nat Prod, 2000 Apr;63(4):473-6.
    PMID: 10785416
    Leaf extracts of the Malaysian plant Aglaia laxiflora provided two cytotoxic compounds, a new rocaglaol rhamnoside (1), a known rocaglaol (2), new (but inactive) flavonol-cinnamaminopyrrolidine adducts (3-6), and their probable biosynthetic precursors (7 and trimethoxyflavonol). All structures were elucidated primarily by 2D NMR spectroscopy. The structure and stereochemistry of aglaxiflorin A (3) were confirmed by single-crystal X-ray crystallography.
  2. Xu J, Harrison LJ, Vittal JJ, Xu YJ, Goh SH
    J Nat Prod, 2000 Aug;63(8):1062-5.
    PMID: 10978198
    Leaf extracts of Callicarpa pentandra provided four new clerodane-type diterpenoids (1-4), of which 1, 2, and 4 have ring-A-contracted structures. Their structures and stereochemistry were established by spectral data interpretation, and for 3 also by single-crystal X-ray diffraction.
  3. Xu YJ, Chiang PY, Lai YH, Vittal JJ, Wu XH, Tan BK, et al.
    J Nat Prod, 2000 Oct;63(10):1361-3.
    PMID: 11076552
    Leaf extracts of Garcinia parvifolia provided relatively high yields of four novel, cytotoxic prenylated depsidones. The structures were determined mainly by detailed NMR spectral analysis and X-ray crystallography.
  4. Xu YJ, Lai YH, Imiyabir Z, Goh SH
    J Nat Prod, 2001 Sep;64(9):1191-5.
    PMID: 11575954
    Nine new xanthones, parvixanthones A-I (1-9), isolated from the dried bark of Garcinia parvifolia, were found to have a common 1,3,6,7-oxygenated pattern for their xanthone nucleus, but various oxygenated isoprenyl or geranyl substituent groups. The structures were determined by spectroscopic methods.
  5. Xu YJ, Jiang F, Song J, Yang X, Shu N, Yuan L, et al.
    J Agric Food Chem, 2020 Aug 19;68(33):8847-8854.
    PMID: 32806128 DOI: 10.1021/acs.jafc.0c03539
    The thermal pretreatment of oilseed prior to oil extraction could increase the oil yield and improve the oil quality. Phenolic compounds are important antioxidants in rapeseed oil. In this study, we investigated the impact of thermal pretreatment method on the rapeseed oil based on phenolic compound levels. Liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) analysis showed that the phenolic compound contents in the microwave-pretreated oil were higher than those in the oven- and infrared-treated oils. Sinapic acid (SA) and canolol (CA), which are the top two phenolic compounds in rapeseed oil, exerted well 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity with IC50 values of 8.45 and 8.80 μmol/L. The cell experiment uncovered that SA and CA have significant biological activities related to rapeseed oil quality, including increase of antioxidant enzymes superoxide dismutase (SOD), alleviation of reactive oxygen species (ROS), and cytotoxicity of HepG2 cells after the intake of excessive oleic acid. Further investigation indicated that SA and CA reduced cell apoptosis rate through Bax-Bcl-2-caspase-3 and p53-Bax-Bcl-2-caspase-3, respectively. Taken together, our findings suggest that microwave pretreatment is the best method to improve the content of phenolic compounds in rapeseed oil compared with oven and infrared pretreatments.
  6. He M, Tan CP, Xu YJ, Liu Y
    Food Res Int, 2020 12;138(Pt B):109812.
    PMID: 33288187 DOI: 10.1016/j.foodres.2020.109812
    Cardiovascular disease (CVD) is a serious disease that endangers human health and is one of the leading causes of death. Recent studies have reported that gut microbiota plays an important role in the development of CVD, especially its metabolite trimethylamine-N-oxide (TMAO). Dietary precursors, such as choline, L-carnitine, phosphatidylcholine and betaine were metabolized to trimethylamine (TMA) under the action of gut microbiota, and subsequently oxidized by hepatic flavin monooxygenases (FMOs) to form TMAO. Dietary fat is one of three major nutrients in food, has been found to have a positive or negative effect on the development of CVD. Multiple clinical and experimental evidences suggested that dietary fatty acids (FAs) can affect TMAO production through gut microbiota and/or FMO3 enzyme activity. This article summarizes the existing gut microbiota-mediated reduction of TMA, discusses the molecular mechanism of dietary FAs in the pathobiology of CVD from the view of TMAO. Therefore, this review provides new insight into the association of dietary FAs and CVD, paving the way for dietary FAs therapy for CVD.
  7. Li X, Tan CP, Liu YF, Xu YJ
    J Agric Food Chem, 2020 Dec 16;68(50):14728-14738.
    PMID: 33289375 DOI: 10.1021/acs.jafc.0c07378
    The intestine is an important digestive organ of the human body, and its barrier is the guardian of the body from the external environment. The impairment of the intestinal barrier is believed to be an important determinant in various foodborne diseases. Food hazards can lead to the occurrence of many foodborne diseases represented by inflammation. Therefore, understanding the mechanisms of the impact of the food hazards on intestinal barriers is essential for promoting human health. This review examined the relationship between food hazards and the intestinal barrier in three aspects: apoptosis, imbalance of gut microbiota, and pro-inflammatory cytokines. The mechanism of dysfunctional gut microbiota caused by food hazards was also discussed. This review discusses the interaction among food hazards, intestinal barrier, and foodborne diseases and, thus, offers a new thought to deal with foodborne disease.
  8. Li X, Nian BB, Tan CP, Liu YF, Xu YJ
    J Sci Food Agric, 2021 Nov 17.
    PMID: 34786719 DOI: 10.1002/jsfa.11659
    BACKGROUND: Deep-frying oil has been found to cause inflammatory bowel disease (IBD). However, the molecular mechanism of the effect of deep-frying palm oil on IBD still remains undetermined.

    RESULTS: In the present study, bioinformatics and cell biology were used to investigate the functions and signal pathway enrichments of differentially expressed genes. The bioinformatics analysis of three original microarray datasets (GSE73661, GSE75214 and GSE126124) in the NCBI-Gene Expression Omnibus database showed 17 down-regulated genes (logFC  0) existed in the enteritis tissue. Meanwhile, pathway enrichment and protein-protein interaction network analysis suggested that IBD is relevant to cytotoxicity, inflammation and apoptosis. Furthermore, Caco-2 cells were treated with the main oxidation products of deep-frying oil-total polar compounds (TPC) and its components (polymerized triglyceride, oxidized triglycerides and triglyceride degradation products) isolated from deep-frying oil. The flow cytometry experiment revealed that TPC and its components could induce apoptosis, especially for oxidized triglyceride. A quantitative polymerase chain reaction analysis demonstrated that TPC and its component could induce Caco-2 cell apoptosis through AQP8/CXCL1/TNIP3/IL-1.

    CONCLUSION: The present study provides fundamental knowledge for understanding the effects of deep-frying oils on the cytotoxic and inflammatory of Caco-2 cells, in addition to clarifying the molecular function mechanism of deep-frying oil in IBD. © 2021 Society of Chemical Industry.

  9. He M, Nian B, Shi J, Sun X, Du R, Tan CP, et al.
    Food Funct, 2022 Jan 04;13(1):270-279.
    PMID: 34888592 DOI: 10.1039/d1fo01507a
    Extraction technology can influence the vegetable oil functional quality. Polyphenols in rapeseed oil have been proved to be beneficial for cardiovascular health. In this study, we evaluated the effect of extraction methods on the functional quality of rapeseed oil from the perspective of phenolic compounds. The results showed that hot pressing produces the highest amount of phenolic compounds in rapeseed oil. Its most abundant phenolic compound, sinapine (9.18 μg g-1), showed the highest activity in inhibiting anaerobic choline metabolism with an EC50 value of 1.9 mM, whose downstream products are related to cardiovascular diseases. Molecular docking and molecular dynamics (MD) simulations revealed that sinapine exhibits good binding affinity toward CutC, and CutC-sinapine is a stable complex with fewer conformational fluctuations and similar tightness. Taken together, hot pressing can be considered the best extraction method for rapeseed oil from the perspective of phenolic compounds.
  10. Li X, Liu YJ, Nian BB, Cao XY, Tan CP, Liu YF, et al.
    Food Chem, 2022 Mar 30;373(Pt B):131285.
    PMID: 34740049 DOI: 10.1016/j.foodchem.2021.131285
    The digestion behavior of epoxy triglyceride, the main cytotoxic product of deep-frying oil, remains unknown, which may affect its biosafety. In this study, epoxy triglyceride (EGT) and triglyceride (GT) were used to reveal the effect of epoxy group on digestion. Digestibility rate analysis showed that the free fatty acids release rate of EGT was slower. To clarify this phenomenon, binding ability with salt ions in digestive juice and particle size were also been studied. Cluster size analysis indicated that epoxy group increased triglyceride particle size, resulting in smaller contact area between EGT and lipase. Interface behaviors displayed EGT decreased binding ability with salt ions in digestive juice. Spectroscopic analysis showed EGT caused the red shift of lipase peak, indicating that epoxy group changed lipase structure. Molecular dynamics simulation suggested EGT leads to loosen lipase structure. In conclusion, this study highlights that epoxy group could weaken the triglyceride digestion.
  11. Ding Z, Jiang F, Shi J, Wang Y, He M, Tan CP, et al.
    Mol Nutr Food Res, 2023 Jan;67(2):e2200508.
    PMID: 36382382 DOI: 10.1002/mnfr.202200508
    SCOPE: Molecular networking (MN) analysis intends to provide chemical insight of untargeted mass spectrometry (MS) data to the user's underlying biological questions. Foodomics is the study of chemical compounds in food using advanced omics methods. In this study, an MS-MN-based foodomics approach is developed to investigate the composition and anti-obesity activity of cannabinoids in hemp oil.

    METHODS AND RESULTS: A total of 16 cannabinoids are determined in optimized microwave pretreatment of hemp oil using the developed approach. Untargeted metabolomics analysis reveals that cannabinoid extract (CE) and its major constituent (cannabidiol, CBD), can alleviate high glucose-induced increases in lipids and carbohydrates, and decreases in amino acid and nucleic acid. Moreover, CE and CBD are also found to suppress the expression levels of mdt-15, sbp-1, fat-5, fat-6, fat-7, daf-2, and elevate the expression level of daf-1, daf-7, daf-16, sod-3, gst-4, lipl-4, resulting in the decrease of lipid synthesis and the enhance of kinetism. Canonical correspondence analysis (CCA) uncovers strong associations between specific metabolic alterations and gene expression levels.

    CONCLUSION: These findings from this exploratory study offer a new insight into the roles of cannabinoids in the treatment of obesity and related complications.

  12. Liu A, Chai X, Zhu S, Chin PT, He M, Xu YJ, et al.
    Int J Biol Macromol, 2023 Jul 31;244:125311.
    PMID: 37302627 DOI: 10.1016/j.ijbiomac.2023.125311
    Astaxanthin (AST) has outstanding antioxidant and anti-inflammation bioactivities, but the low biocompatibility and stability limit its application in foods. In this study, N-succinyl-chitosan (NSC)-coated AST polyethylene glycol (PEG)-liposomes were constructed to enhance the biocompatibility, stability, and intestinal-targeted migration of AST. The AST NSC/PEG-liposomes were uniform in size, had larger particles, greater encapsulation efficiency, and better storage, pH, and temperature stability than the AST PEG-liposomes. AST NSC/PEG-liposomes exerted stronger antibacterial and antioxidant activities against Escherichia coli and Staphylococcus aureus than AST PEG-liposomes. The NSC coating not only protects AST PEG-liposomes from gastric acid but also prolongs the retention and sustained release of AST NSC/PEG-liposomes depending on the intestinal pH. Moreover, caco-2 cellular uptake studies showed that AST NSC/PEG-liposomes had higher cellular uptake efficiency than AST PEG-liposomes. And AST NSC/PEG-liposomes were taken up by caco-2 cells through clathrin mediated endocytic, macrophage pathways and paracellular transport pathway. These results further proved that AST NSC/PEG-liposomes delayed the release and promoted the intestinal absorption of AST. Hence, AST PEG-liposomes coated with NSC could potentially be used as an efficient delivery system for therapeutic AST.
  13. Zhang Y, Shi J, Tan C, Liu Y, Xu YJ
    Food Res Int, 2023 Nov;173(Pt 1):113301.
    PMID: 37803609 DOI: 10.1016/j.foodres.2023.113301
    Oil is one of three nutritious elements. The application of omics techniques in the field of oil science and technology is attracted increasing attention. Oilomics, which emerged as an important branch of foodomics, has been widely used in various aspects of oil science and technology. However, there are currently no articles systematically reviewing the application of oilomics. This paper aims to provide a critical overview of the advantages and value of oilomics technology compared to traditional techniques in various aspects of oil science and technology, including oil nutrition, oil processing, oil quality, safety, and traceability. Moreover, this article intends to review major issues in oilomics and give a comprehensive, critical overview of the current state of the art, future challenges and trends in oilomics, with a view to promoting the optimal application and development of oilomics technology in oil science and technology.
  14. Shi J, Zhao J, Zhang Y, Wang Y, Tan CP, Xu YJ, et al.
    Anal Chem, 2023 Dec 26;95(51):18793-18802.
    PMID: 38095040 DOI: 10.1021/acs.analchem.3c03785
    Metabolomics and proteomics offer significant advantages in understanding biological mechanisms at two hierarchical levels. However, conventional single omics analysis faces challenges due to the high demand for specimens and the complexity of intrinsic associations. To obtain comprehensive and accurate system biological information, we developed a multiomics analytical method called Windows Scanning Multiomics (WSM). In this method, we performed simultaneous extraction of metabolites and proteins from the same sample, resulting in a 10% increase in the coverage of the identified biomolecules. Both metabolomics and proteomics analyses were conducted by using ultrahigh-performance liquid chromatography mass spectrometry (UPLC-MS), eliminating the need for instrument conversions. Additionally, we designed an R-based program (WSM.R) to integrate mathematical and biological correlations between metabolites and proteins into a correlation network. The network created from simultaneously extracted biomolecules was more focused and comprehensive compared to those from separate extractions. Notably, we excluded six pairs of false-positive relationships between metabolites and proteins in the network established using simultaneously extracted biomolecules. In conclusion, this study introduces a novel approach for multiomics analysis and data processing that greatly aids in bioinformation mining from multiomics results. This method is poised to play an indispensable role in systems biology research.
  15. Lei J, He Y, Zhu S, Shi J, Tan CP, Liu Y, et al.
    Analyst, 2024 Jan 29;149(3):751-760.
    PMID: 38194259 DOI: 10.1039/d3an01536j
    Polyunsaturated fatty acids (PUFAs), such as arachidonic acid (ARA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), play an important role in the nutritional value of milk lipids. However, a comprehensive analysis of PUFAs and their esters in milk is still scarce. In this study, we developed a novel pseudotargeted lipidomics approach, named SpecLipIDA, for determining PUFA lipids in milk. Triglycerides (TGs) and phospholipids (PLs) were separated using NH2 cartridges, and mass spectrometry data in the information-dependent acquisition (IDA) mode were preprocessed by MS-DIAL, leading to improved identification in subsequent targeted analysis. The target matching algorithm, based on specific lipid cleavage patterns, demonstrated enhanced identification of PUFA lipids compared to the lipid annotations provided by MS-DIAL and GNPS. The approach was applied to identify PUFA lipids in various milk samples, resulting in the detection of a total of 115 PUFA lipids. The results revealed distinct differences in PUFA lipids among different samples, with 44 PUFA lipids significantly contributing to these differences. Our study indicated that SpecLipIDA is an efficient method for rapidly and specifically screening PUFA lipids.
  16. Zhao J, Shi J, Chen X, Lei Y, Tian T, Zhu S, et al.
    Mol Omics, 2024 Mar 25;20(3):192-202.
    PMID: 38224158 DOI: 10.1039/d3mo00232b
    Areca nut (Areca catechu L.) is commonly consumed as a chewing food in the Asian region. However, the investigations into the components of areca nut are limited. In this study, we have developed an approach that combines mass spectrometry with feature-based molecular network to explore the chemical characteristics of the areca nut. In comparison to the conventional method, this technique demonstrates a superior capability in annotating unknown compounds present in areca nut. We annotated a total of 52 compounds, including one potential previously unreported alkaloid, one carbohydrate, and one phenol and confirmed the presence of 7 of them by comparing with commercial standards. The validated method was used to evaluate chemical features of areca nut at different growth stages, annotating 25 compounds as potential biomarkers for distinguishing areca nut growth stages. Therefore, this approach offers a rapid and accurate method for the component analysis of areca nut.
  17. Liu A, He M, Liu C, Ye Z, Tan CP, Liu Y, et al.
    J Agric Food Chem, 2024 Mar 27;72(12):6118-6132.
    PMID: 38477232 DOI: 10.1021/acs.jafc.3c08697
    Cardiovascular diseases are caused by hypercholesterolemia. Astaxanthin (AST) has been reported to exhibit antioxidant and anti-inflammatory properties. However, its bioavailability is poor because of low solubility and instability. In order to improve the bioavailability of AST, we developed an intestinal-responsive composite carrier termed as "liposomes in micropheres" incorporating N-succinyl-chitosan (NSC)-poly(ethylene glycol) (PEG) liposomes that functionalized by neonatal Fc receptors (FcRn) into hydrogels of sodium alginate (SA) and carboxymethyl chitosan (CMCS). In the AST NSC/HSA-PEG liposomes@SA/CMCS microspheres, the AST's encapsulation efficiency (EE) was 96.26% (w/w) and its loading capacity (LC) was 6.47% (w/w). AST NSC/HSA-PEG liposomes had stability in the gastric conditions and achieved long-term release of AST in intestinal conditions. Then, AST NSC/HSA-PEG liposomes@SA/CMCS bind to intestinal epithelial cell targets by the neonatal Fc receptor. In vitro permeation studies show that there was a 4-fold increase of AST NSC/HSA-PEG liposomes@SA/CMCS in AST permeation across the intestinal epithelium. Subsequent in vivo experiments demonstrated that the composite carrier exhibited a remarkable mucoadhesive capacity, allowing for extended intestinal retention of up to 12 h, and it displayed deep penetration through the mucus layer, efficiently entering the intestinal villi epithelial cells, and enhancing the absorption of AST and its bioavailability in vivo. And oral administration of AST NSC/HSA-PEG liposomes@SA/CMCS could effectively prevent hypercholesterolemia caused by a high-fat, high-cholesterol diet (HFHCD). These advancements highlight the potential of NSC/HSA-PEG liposomes@SA/CMCS composite carriers for targeted and oral uptake of hydrophobic bioactives.
  18. He Y, Zhu S, Zhang Y, Tan CP, Zhang J, Liu Y, et al.
    Eur J Clin Nutr, 2024 Apr 12.
    PMID: 38609641 DOI: 10.1038/s41430-024-01438-4
    BACKGROUND: Despite the abundance of research examining the effects of coffee, tea, and alcohol on inflammatory diseases, there is a notable absence of conclusive evidence regarding their direct causal influence on circulating inflammatory cytokines. Previous studies have primarily concentrated on established cytokines, neglecting the potential impact of beverage consumption on lesser-studied but equally important cytokines.

    METHODS: Information regarding the consumption of coffee, tea, and alcohol was collected from the UK Biobank, with sample sizes of 428,860, 447,485, and 462,346 individuals, respectively. Data on 41 inflammatory cytokines were obtained from summary statistics of 8293 healthy participants from Finnish cohorts.

    RESULTS: The consumption of coffee was found to be potentially associated with decreased levels of Macrophage colony-stimulating factor (β = -0.57, 95% CI -1.06 ~ -0.08; p = 0.022) and Stem cell growth factor beta (β = -0.64, 95% CI -1.16 ~ -0.12; p = 0.016), as well as an increase in TNF-related apoptosis-inducing ligand (β = 0.43, 95% CI 0.06 ~ 0.8; p = 0.023) levels. Conversely, tea intake was potentially correlated with a reduction in Interleukin-8 (β = -0.45, 95% CI -0.9 ~ 0; p = 0.045) levels. Moreover, our results indicated an association between alcohol consumption and decreased levels of Regulated on Activation, Normal T Cell Expressed and Secreted (β = -0.24, 95% CI -0.48 ~ 0; p = 0.047), as well as an increase in Stem cell factor (β = 0.17, 95% CI 0.02 ~ 0.31; p = 0.023) and Stromal cell-derived factor-1 alpha (β = 0.20, 95% CI 0.04 ~ 0.36; p = 0.013).

    CONCLUSION: Revealing the interactions between beverage consumption and various inflammatory cytokines may lead to the discovery of novel therapeutic targets, thereby facilitating dietary interventions to complement clinical disease treatments.

  19. Wang Y, Shi J, Xu YJ, Tan CP, Liu Y
    Food Chem, 2024 Apr 16;438:137400.
    PMID: 38039864 DOI: 10.1016/j.foodchem.2023.137400
    The digestion behavior of lipids plays a crucial role in their nutritional bioaccessibility, which subsequently impacts human health. This study aims to investigate potential variations in lipid digestion profiles among individuals of different ages, considering the distinct physiological functions of the gastrointestinal tract in infants, aging populations, and healthy young adults. The digestion fates of high oleic peanut oil (HOPO), sunflower oil (SO), and linseed oil (LINO) were investigated using in vitro digestion models representing infants, adults, and elders. Comparatively, lipid digestion proved to be more comprehensive in adults, leading to free fatty acid (FFA) levels of 64.53%, 62.32%, and 57.90% for HOPO, SO, and LINO, respectively. Besides, infants demonstrated propensity to selectively release FFAs with shorter chain lengths and higher saturation levels during the digestion. In addition, in the gastric phase, particle sizes among the elderly were consistently larger than those observed in infants and adults, despite adults generating approximately 15% FFAs within the stomach. In summary, this study enhances our fundamental comprehension of how lipids with varying degrees of unsaturation undergo digestion in diverse age groups.
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