The effect of adding hydroxycinnamic acids(caffeic acid,sinapic acid,p-coumaric acid and chlorogenic acid)in Cabernet Sauvignon dry red wine before and after fermentation was investigated,taking into account the color...The effect of adding hydroxycinnamic acids(caffeic acid,sinapic acid,p-coumaric acid and chlorogenic acid)in Cabernet Sauvignon dry red wine before and after fermentation was investigated,taking into account the color parameters,anthocyanin content,and overall polyphenol levels in the wine samples.The copigmentation effect of malvidin-3-Oglucoside and sinapic acid was further explored in model solution and through theoretical calculations.The results indicated that the addition of hydroxycinnamic acids significantly enhanced the wine's color with sinapic acid(before the fermentation)showing the most pronounced color protection effect.Compared to control samples,the addition of hydroxycinnamic acids resulted in a 36%increase in total phenolic content and a 28% increase in total anthocyanin content.Thermodynamic analysis revealed that the interaction between sinapic acid and malvidin-3-O-glucoside was spontaneous and exothermic.Theoretical studies identified hydrogen bonding(HB)and dispersion forces as the main primary stabilizing forces,with the carboxyl group of sinapic acid playing a critical role while the anthocyanin backbone also influenced the interaction.展开更多
Hydroxycinnamic acids(HCAs)including ferulic,caffeic,coumaric,rosmarinic and chlorogenic acids are widely present in plant-based foods and herbal extracts.They are renowned for their health-promoting properties such a...Hydroxycinnamic acids(HCAs)including ferulic,caffeic,coumaric,rosmarinic and chlorogenic acids are widely present in plant-based foods and herbal extracts.They are renowned for their health-promoting properties such as antioxidant,anti-inflammatory,antidiabetic and anticancer activities.However,their bioavailability is low and their metabolic pathways within the gastrointestinal tract are highly complex.Hence,understanding how HCAs are transformed,absorbed,and metabolized during digestion is crucial to evaluate their physiological relevance.This review highlights the bioavailability,absorption,digestion and metabolism of natural HCAs.It comprehensively examines the bioavailability,absorption and digestion mechanism of natural HCAs across different digestive compartments,including the oral cavity,stomach and intestinal tract.Additionally,it criti-cally discussed the key factors influencing the digestion and metabolism of HCAs such as pH,digestive enzymes and microbial composition.In the oral cavities,HCAs undergo limited enzymatic and oral bacterial degradation,with some exhibiting antimicrobial activity.Absorption in oral cavity and stomach is minimal,and HCAs are relatively stable under acidic gastric conditions.However,acidic environment in the stomach promotes partial degradation through reaction with salivary components to form thiocyanate and oxathiolone derivatives.The intestinal tract serves as the main site for HCAs absorption and degradation.The presence of various enzymes and alkali conditions causes the production of HCA metabolites such as glucuronides,sulfates and methylated derivatives.The metabolites possess the health benefits similar to those of the intact HCAs compounds.Further studies on the bioavailability,absorption and degradation metabolism of HCAs are strongly required for enhanced nutraceutical and therapeutic applications.展开更多
Hybrid antioxidants cinnamoyldopamine（2a）, p-coumaroyldopamine（2b）, caffeoyldopamine（2c）, feruloyldopamine（2d） and sinapoyldopamine（2e） were synthesized by conjugation of dopamine（DA） and hydroxycinnamic a...Hybrid antioxidants cinnamoyldopamine（2a）, p-coumaroyldopamine（2b）, caffeoyldopamine（2c）, feruloyldopamine（2d） and sinapoyldopamine（2e） were synthesized by conjugation of dopamine（DA） and hydroxycinnamic acids（HCAs）. The stabilities were studied in buffers at p H 1.3, p H 5.0, and p H 7.4 including the human plasma. All the compounds were found highly stable at acidic p H, but underwent hydrolysis at neutral p H. Furthermore, the hydrolysis proceeded much faster in plasma in the following order as indicated by half-life values（t1/2）, 2c（1.21 h）〈2e（1.52 h）〈2d（1.85 h）〈2b（3.38 h）〈2a（3.88 h）, correlating with the number of electron-donating groups. It has been proven by UV spectrum that 2c, 2d, and 2e displayed red shift of more than 50 nm as compared to 2a and 2b, because of the presence of OH and OCH3 groups. In addition, the compounds（2b–e） showed no cytotoxicity on normal HUVEC cells as DA, although 2a displayed a 16% inhibition of proliferation at 40 μM following 48 h incubation. Their free radical-scavenging activities were evaluated using ABTS^＊＋ and superoxide anion assays and the mechanisms were proposed. It was found that they all exhibited higher activities than trolox, a recognized antioxidant. Amazingly, in the case of the hybrids（2a–e）, their activity was higher than that of HCAs while lower or comparable to that of DA, suggesting that there may be a ＂saturation effect＂ with the hybrid molecules in the antioxidant activities.展开更多
In order to develop agents with superior chemopreventive and chemotherapeutic properties against hepatocellular carcinomas, mitochondria-targeted hydroxycinnamic acids(Mito HCAs) were synthesized by conjugation with a...In order to develop agents with superior chemopreventive and chemotherapeutic properties against hepatocellular carcinomas, mitochondria-targeted hydroxycinnamic acids(Mito HCAs) were synthesized by conjugation with a triphenylphosphonium cation. These synthetic compounds were evaluated for their antioxidant activities in hepatic mitochondria, including against OH? àand ROO? àinduced lipid peroxidation. H_2O_2 production was decreased significantly by increasing glutathione peroxidase and catalase activities. In addition, cell proliferation data from three cell lines(HepG2, L02 and WI38) indicated that the Mito HCAs were selective for cancer cells. Interestingly, the Mito HCAs both with or without Ca^(2+)triggered mitochondrial dysfunction by inducing mitochondrial swelling, collapsing the mitochondrial membrane potential and causing cytochrome c release. In particular, an inhibitor of the mitochondrial permeability transition pore(m PTP), cyclosporin A, attenuated mitochondrial damage and cell apoptosis, indicating that m PTP may be involved in the antiproliferative activity of Mito HCAs.Further studies focused on structural optimization of these compounds are onging.展开更多
Sichuan Paocai is a kind of fermented vegetable with rich microorganism and enzyme resources.Based on our previous metatranscriptomics and flavor-oriented metabolomics studies,three potential phenolic acid decarboxyla...Sichuan Paocai is a kind of fermented vegetable with rich microorganism and enzyme resources.Based on our previous metatranscriptomics and flavor-oriented metabolomics studies,three potential phenolic acid decarboxylases LvPAD,DhFDC1 and LvUbiD were mined from environmental RNA of industrial Sichuan Paocai,and their catalytic function were verified by heterologous expression.LvPAD,which was derived from Lactobacillus vermolensis and had the highest catalytic activity among the three enzymes,was selected for further purification and characterization.It was optimally active at pH 6.0 and 35℃,had good thermal stability and pH tolerance,and did not require specific cofactors.Kinetic parameters showed that LvPAD could catalyze the decarboxylation of p-coumaric acid,ferulic acid and caffeic acid with the kcat/Km values of 460.6±0.1,23.7±0.09 and 118.2±0.1 mM^(-1)s^(-1),respectively,and the products of the first two substrates were 4-vinylphenol and 4-vinylguaiacol with aromatic characteristics.Moreover,LvPAD was successfully used to preliminarily strengthen the vinylphenol aroma of industrial Paocai,which could shorten the fermentation time to a certain extent in practical production.Therefore,this work not only validated the important role of LvPAD in the production of aromatic phenols in Paocai,but also facilitated the mining of more enzymes from Paocai to improve the flavor and production process in the future.展开更多
Genomic clustering of non-homologous genes for the biosynthesis of plant defensive compounds is an emerging theme, but insights into their formation and physiological function remain limited. Here we report the identi...Genomic clustering of non-homologous genes for the biosynthesis of plant defensive compounds is an emerging theme, but insights into their formation and physiological function remain limited. Here we report the identification of a newly discovered hydroxycinnamoyl tyramine(HT) gene cluster in rice.This cluster contains a pyridoxamine 50-phosphate oxidase(Os PDX3) producing the cofactor pyridoxal50-phosphate(PLP), a PLP-dependent tyrosine decarboxylase(Os Ty DC1), and two duplicated hydroxycinnamoyl transferases(Os THT1 and Os THT2). These members were combined to represent an enzymological innovation gene cluster. Natural variation analysis showed that the abundance of the toxic tyramine intermediate of the gene cluster among different rice accessions is mainly determined by the coordinated transcription of Os Ty DC1 and Os THT1. Further pathogen incubation assays demonstrated that the end products of the HT gene cluster displayed enhanced resistance to the bacterial pathogen Xanthomonas oryzae pv. Oryzae(Xoo) and fungal pathogen Magnaporthe oryzae(M. oryzae), and the enhanced resistance is associated with the boost of phytoalexins and the activation of defense response. The unique presence of the HT gene cluster in Oryza AA genome, together with the enrichment of transposon elements within this gene cluster region, provides an evolutionary background to accelerate cluster member combinations. Our study not only discovered a gene cluster involved in the phenylpropanoid metabolism but also addressed the key aspects of gene cluster formation. In addition, our results provide a new metabolic pool for plant defense against pathogens.展开更多
基金supported by the Key R&D Program of Shaanxi Province,China(2024NC-YBXM-146)the Xi’an Agricultural Technology Research and Development Project,China(24NYGG0048)+1 种基金the Key R&D Program of Xianyang,China(L2024-ZDYF-ZDYF-NY-0028)the National Foreign Expert Project of China(G2023172002L)。
文摘The effect of adding hydroxycinnamic acids(caffeic acid,sinapic acid,p-coumaric acid and chlorogenic acid)in Cabernet Sauvignon dry red wine before and after fermentation was investigated,taking into account the color parameters,anthocyanin content,and overall polyphenol levels in the wine samples.The copigmentation effect of malvidin-3-Oglucoside and sinapic acid was further explored in model solution and through theoretical calculations.The results indicated that the addition of hydroxycinnamic acids significantly enhanced the wine's color with sinapic acid(before the fermentation)showing the most pronounced color protection effect.Compared to control samples,the addition of hydroxycinnamic acids resulted in a 36%increase in total phenolic content and a 28% increase in total anthocyanin content.Thermodynamic analysis revealed that the interaction between sinapic acid and malvidin-3-O-glucoside was spontaneous and exothermic.Theoretical studies identified hydrogen bonding(HB)and dispersion forces as the main primary stabilizing forces,with the carboxyl group of sinapic acid playing a critical role while the anthocyanin backbone also influenced the interaction.
基金supported by the research grant of Universiti Teknologi Malaysia[Q.J130000.3846.23H03].
文摘Hydroxycinnamic acids(HCAs)including ferulic,caffeic,coumaric,rosmarinic and chlorogenic acids are widely present in plant-based foods and herbal extracts.They are renowned for their health-promoting properties such as antioxidant,anti-inflammatory,antidiabetic and anticancer activities.However,their bioavailability is low and their metabolic pathways within the gastrointestinal tract are highly complex.Hence,understanding how HCAs are transformed,absorbed,and metabolized during digestion is crucial to evaluate their physiological relevance.This review highlights the bioavailability,absorption,digestion and metabolism of natural HCAs.It comprehensively examines the bioavailability,absorption and digestion mechanism of natural HCAs across different digestive compartments,including the oral cavity,stomach and intestinal tract.Additionally,it criti-cally discussed the key factors influencing the digestion and metabolism of HCAs such as pH,digestive enzymes and microbial composition.In the oral cavities,HCAs undergo limited enzymatic and oral bacterial degradation,with some exhibiting antimicrobial activity.Absorption in oral cavity and stomach is minimal,and HCAs are relatively stable under acidic gastric conditions.However,acidic environment in the stomach promotes partial degradation through reaction with salivary components to form thiocyanate and oxathiolone derivatives.The intestinal tract serves as the main site for HCAs absorption and degradation.The presence of various enzymes and alkali conditions causes the production of HCA metabolites such as glucuronides,sulfates and methylated derivatives.The metabolites possess the health benefits similar to those of the intact HCAs compounds.Further studies on the bioavailability,absorption and degradation metabolism of HCAs are strongly required for enhanced nutraceutical and therapeutic applications.
基金The National Natural Science Foundation of China(Grant No.21302079)the Fundamental Research Funds for the Central Universities(Grant No.lzujbky-2014-151)
文摘Hybrid antioxidants cinnamoyldopamine（2a）, p-coumaroyldopamine（2b）, caffeoyldopamine（2c）, feruloyldopamine（2d） and sinapoyldopamine（2e） were synthesized by conjugation of dopamine（DA） and hydroxycinnamic acids（HCAs）. The stabilities were studied in buffers at p H 1.3, p H 5.0, and p H 7.4 including the human plasma. All the compounds were found highly stable at acidic p H, but underwent hydrolysis at neutral p H. Furthermore, the hydrolysis proceeded much faster in plasma in the following order as indicated by half-life values（t1/2）, 2c（1.21 h）〈2e（1.52 h）〈2d（1.85 h）〈2b（3.38 h）〈2a（3.88 h）, correlating with the number of electron-donating groups. It has been proven by UV spectrum that 2c, 2d, and 2e displayed red shift of more than 50 nm as compared to 2a and 2b, because of the presence of OH and OCH3 groups. In addition, the compounds（2b–e） showed no cytotoxicity on normal HUVEC cells as DA, although 2a displayed a 16% inhibition of proliferation at 40 μM following 48 h incubation. Their free radical-scavenging activities were evaluated using ABTS^＊＋ and superoxide anion assays and the mechanisms were proposed. It was found that they all exhibited higher activities than trolox, a recognized antioxidant. Amazingly, in the case of the hybrids（2a–e）, their activity was higher than that of HCAs while lower or comparable to that of DA, suggesting that there may be a ＂saturation effect＂ with the hybrid molecules in the antioxidant activities.
基金supported by the National Natural Sciences Foundation of China (Grant No. 21302079)the Fundamental Research Funds for the Central Universities (No. lzujbky2014151)
文摘In order to develop agents with superior chemopreventive and chemotherapeutic properties against hepatocellular carcinomas, mitochondria-targeted hydroxycinnamic acids(Mito HCAs) were synthesized by conjugation with a triphenylphosphonium cation. These synthetic compounds were evaluated for their antioxidant activities in hepatic mitochondria, including against OH? àand ROO? àinduced lipid peroxidation. H_2O_2 production was decreased significantly by increasing glutathione peroxidase and catalase activities. In addition, cell proliferation data from three cell lines(HepG2, L02 and WI38) indicated that the Mito HCAs were selective for cancer cells. Interestingly, the Mito HCAs both with or without Ca^(2+)triggered mitochondrial dysfunction by inducing mitochondrial swelling, collapsing the mitochondrial membrane potential and causing cytochrome c release. In particular, an inhibitor of the mitochondrial permeability transition pore(m PTP), cyclosporin A, attenuated mitochondrial damage and cell apoptosis, indicating that m PTP may be involved in the antiproliferative activity of Mito HCAs.Further studies focused on structural optimization of these compounds are onging.
基金supported by the National Natural Science Foundation of China(Program No.31871788).
文摘Sichuan Paocai is a kind of fermented vegetable with rich microorganism and enzyme resources.Based on our previous metatranscriptomics and flavor-oriented metabolomics studies,three potential phenolic acid decarboxylases LvPAD,DhFDC1 and LvUbiD were mined from environmental RNA of industrial Sichuan Paocai,and their catalytic function were verified by heterologous expression.LvPAD,which was derived from Lactobacillus vermolensis and had the highest catalytic activity among the three enzymes,was selected for further purification and characterization.It was optimally active at pH 6.0 and 35℃,had good thermal stability and pH tolerance,and did not require specific cofactors.Kinetic parameters showed that LvPAD could catalyze the decarboxylation of p-coumaric acid,ferulic acid and caffeic acid with the kcat/Km values of 460.6±0.1,23.7±0.09 and 118.2±0.1 mM^(-1)s^(-1),respectively,and the products of the first two substrates were 4-vinylphenol and 4-vinylguaiacol with aromatic characteristics.Moreover,LvPAD was successfully used to preliminarily strengthen the vinylphenol aroma of industrial Paocai,which could shorten the fermentation time to a certain extent in practical production.Therefore,this work not only validated the important role of LvPAD in the production of aromatic phenols in Paocai,but also facilitated the mining of more enzymes from Paocai to improve the flavor and production process in the future.
基金supported by the National Science Fund for Distinguished Young Scholars of China (31625021)the Foundation for Innovative Research Groups of the National Natural Science Foundation of China (31821005)+1 种基金the State Key Program of National Natural Science Foundation of China (31530052)the Hainan University Startup Fund (KYQD(ZR)1866)。
文摘Genomic clustering of non-homologous genes for the biosynthesis of plant defensive compounds is an emerging theme, but insights into their formation and physiological function remain limited. Here we report the identification of a newly discovered hydroxycinnamoyl tyramine(HT) gene cluster in rice.This cluster contains a pyridoxamine 50-phosphate oxidase(Os PDX3) producing the cofactor pyridoxal50-phosphate(PLP), a PLP-dependent tyrosine decarboxylase(Os Ty DC1), and two duplicated hydroxycinnamoyl transferases(Os THT1 and Os THT2). These members were combined to represent an enzymological innovation gene cluster. Natural variation analysis showed that the abundance of the toxic tyramine intermediate of the gene cluster among different rice accessions is mainly determined by the coordinated transcription of Os Ty DC1 and Os THT1. Further pathogen incubation assays demonstrated that the end products of the HT gene cluster displayed enhanced resistance to the bacterial pathogen Xanthomonas oryzae pv. Oryzae(Xoo) and fungal pathogen Magnaporthe oryzae(M. oryzae), and the enhanced resistance is associated with the boost of phytoalexins and the activation of defense response. The unique presence of the HT gene cluster in Oryza AA genome, together with the enrichment of transposon elements within this gene cluster region, provides an evolutionary background to accelerate cluster member combinations. Our study not only discovered a gene cluster involved in the phenylpropanoid metabolism but also addressed the key aspects of gene cluster formation. In addition, our results provide a new metabolic pool for plant defense against pathogens.
