首页 > 最新文献

Antioxidants最新文献

英文 中文
Influence of Pediococcus pentosaceus Starter Cultures on Biogenic Amine Content and Antioxidant Activity in African Sourdough Flatbread Fermentation. 五胜肽球菌起始培养物对非洲酸面团扁面包发酵过程中生物胺含量和抗氧化活性的影响
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-07 DOI: 10.3390/antiox13101204
Alaa Ahmed Alsiddig Hassan, Young Hun Jin, Jae-Hyung Mah

This study investigated the impact of Pediococcus pentosaceus strains not only on biogenic amine (BA) content, but also on antioxidant indices, including 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity and total phenolic content, in kisra, an African sourdough flatbread. Among forty-six lactic acid bacteria (LAB) strains isolated from naturally fermented kisra sourdough, two strains (K-B21, K-B01) identified as P. pentosaceus, were selected due to their low BA-producing and high BA-degrading ability for kisra fermentation. Inoculation with P. pentosaceus K-B21 or P. pentosaceus K-B01 completely prevented the formation of tyramine and cadaverine during kisra fermentation. The levels of putrescine, histamine, spermine, and spermidine in kisra were reduced by about 90%, >31%, 55-61%, and 9-25%, respectively, by the two strains, compared to the control (natural fermentation). Additionally, DPPH scavenging activity was 83-84% in the control and inoculated groups of kisra. The total phenolic content was 1977.60 μg/g in the control and insignificantly lower in the inoculated groups (1850-1880 μg/g) than the control. These results suggest that P. pentosaceus K-B21 and K-B01 are promising candidates for use as sourdough starter cultures to produce kisra bread of higher quality, including both its safety and health functionality.

本研究调查了五胜肽球菌(Pediococcus pentosaceus)菌株不仅对生物胺(BA)含量的影响,还对非洲酸面团(kisra)中的抗氧化指数(包括 2,2-二苯基-1-苦基肼(DPPH)清除活性和总酚含量)的影响。在从自然发酵的基斯拉酸面团中分离出的 46 株乳酸菌(LAB)中,有两株(K-B21 和 K-B01)被鉴定为戊糖杆菌,它们具有低 BA 产出和高 BA 降解能力,因此被选中用于基斯拉发酵。接种 P. pentosaceus K-B21 或 P. pentosaceus K-B01 能完全阻止基斯拉发酵过程中酪胺和尸胺的形成。与对照组(自然发酵)相比,这两种菌株可使 kisra 中的腐胺、组胺、精胺和亚精胺的含量分别减少约 90%、31%、55%-61% 和 9%-25%。此外,对照组和接种组基斯拉的 DPPH 清除活性为 83-84%。对照组的总酚含量为 1977.60 μg/g,接种组的总酚含量(1850-1880 μg/g)显著低于对照组。这些结果表明,P. pentosaceus K-B21 和 K-B01 有希望用作酸包粉起始培养物,以生产出更高质量的基斯拉面包,包括其安全性和保健功能。
{"title":"Influence of <i>Pediococcus pentosaceus</i> Starter Cultures on Biogenic Amine Content and Antioxidant Activity in African Sourdough Flatbread Fermentation.","authors":"Alaa Ahmed Alsiddig Hassan, Young Hun Jin, Jae-Hyung Mah","doi":"10.3390/antiox13101204","DOIUrl":"10.3390/antiox13101204","url":null,"abstract":"<p><p>This study investigated the impact of <i>Pediococcus pentosaceus</i> strains not only on biogenic amine (BA) content, but also on antioxidant indices, including 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity and total phenolic content, in kisra, an African sourdough flatbread. Among forty-six lactic acid bacteria (LAB) strains isolated from naturally fermented kisra sourdough, two strains (K-B21, K-B01) identified as <i>P. pentosaceus,</i> were selected due to their low BA-producing and high BA-degrading ability for kisra fermentation. Inoculation with <i>P. pentosaceus</i> K-B21 or <i>P. pentosaceus</i> K-B01 completely prevented the formation of tyramine and cadaverine during kisra fermentation. The levels of putrescine, histamine, spermine, and spermidine in kisra were reduced by about 90%, >31%, 55-61%, and 9-25%, respectively, by the two strains, compared to the control (natural fermentation). Additionally, DPPH scavenging activity was 83-84% in the control and inoculated groups of kisra. The total phenolic content was 1977.60 μg/g in the control and insignificantly lower in the inoculated groups (1850-1880 μg/g) than the control. These results suggest that <i>P. pentosaceus</i> K-B21 and K-B01 are promising candidates for use as sourdough starter cultures to produce kisra bread of higher quality, including both its safety and health functionality.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504419/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493372","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Antioxidant Function and Application of Plant-Derived Peptides. 植物肽的抗氧化功能和应用。
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-06 DOI: 10.3390/antiox13101203
Zhengqing Zhu, Ziwu Xu, Yuhang Li, Yutong Fan, Yingqian Zhou, Kaixin Song, Lei Meng

With the development of society and the improvement of people's health consciousness, the demand for antioxidants is increasing. As a natural antioxidant with no toxic side effects, antioxidant peptides are widely used in food, cosmetics, medicine, and other fields because of their strong antioxidant capacity and easy absorption by the human body. Plant-derived antioxidant peptides have attracted more attention than animal-derived antioxidant peptides because plants are more diverse than animals and produce a large number of protein-rich by-products during the processing of their products, which are the main source of antioxidant peptides. In this review, we summarize the source, structure and activity, other biological functions, mechanism of action, and comprehensive applications of plant antioxidant peptides, and look forward to their future development trends, which will provide a reference for further research and development of plant antioxidant peptides.

随着社会的发展和人们健康意识的提高,人们对抗氧化剂的需求日益增加。抗氧化肽作为一种无毒副作用的天然抗氧化剂,因其抗氧化能力强、易被人体吸收等特点,被广泛应用于食品、化妆品、医药等领域。与动物源抗氧化肽相比,植物源抗氧化肽更受关注,因为植物的种类比动物多,在产品加工过程中会产生大量富含蛋白质的副产品,而这些副产品正是抗氧化肽的主要来源。在这篇综述中,我们总结了植物抗氧化肽的来源、结构与活性、其他生物学功能、作用机理以及综合应用,并展望了其未来的发展趋势,这将为进一步研究和开发植物抗氧化肽提供参考。
{"title":"Antioxidant Function and Application of Plant-Derived Peptides.","authors":"Zhengqing Zhu, Ziwu Xu, Yuhang Li, Yutong Fan, Yingqian Zhou, Kaixin Song, Lei Meng","doi":"10.3390/antiox13101203","DOIUrl":"10.3390/antiox13101203","url":null,"abstract":"<p><p>With the development of society and the improvement of people's health consciousness, the demand for antioxidants is increasing. As a natural antioxidant with no toxic side effects, antioxidant peptides are widely used in food, cosmetics, medicine, and other fields because of their strong antioxidant capacity and easy absorption by the human body. Plant-derived antioxidant peptides have attracted more attention than animal-derived antioxidant peptides because plants are more diverse than animals and produce a large number of protein-rich by-products during the processing of their products, which are the main source of antioxidant peptides. In this review, we summarize the source, structure and activity, other biological functions, mechanism of action, and comprehensive applications of plant antioxidant peptides, and look forward to their future development trends, which will provide a reference for further research and development of plant antioxidant peptides.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11505357/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493356","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Quercetin and Thyroid. 槲皮素与甲状腺
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-04 DOI: 10.3390/antiox13101202
Cesidio Giuliani, Giulia Di Dalmazi, Ines Bucci, Giorgio Napolitano

Quercetin is the most abundant flavonoid present in fruits and vegetables. For its antiproliferative, antiviral, anti-inflammatory and antioxidants activities, it is an active ingredient of several herbal remedies and is available as a nutraceutical. Experimental studies performed in vitro have demonstrated that quercetin inhibits growth and function in normal thyroid cells and may act as a thyroid disruptor. These effects have also been confirmed in vivo using rodent models. Some studies have reported the ability of quercetin to interfere with the metabolism of thyroid hormones, since it inhibits the 5'-deiodinase type 1 (D1) activity in the thyroid, as well as in the liver. Besides the effects on normal thyroid cells, several experiments performed in vitro have shown a potential therapeutic role of quercetin in thyroid cancer. Indeed, quercetin inhibits the growth, the adhesion and the migration of thyroid cancer cells, and it also has redifferentiation properties in some thyroid cancer cell lines. In conclusion, these data suggest that, although its effects can be of benefit in hyperthyroidism and thyroid cancer, caution is required in the use of high doses of quercetin due to its anti-thyroid properties. Further in vivo studies are certainly needed to confirm these hypotheses.

槲皮素是水果和蔬菜中含量最高的类黄酮。槲皮素具有抗增殖、抗病毒、抗炎和抗氧化作用,是多种草药的有效成分,也可作为营养保健品出售。体外实验研究表明,槲皮素会抑制正常甲状腺细胞的生长和功能,并可能成为甲状腺干扰素。利用啮齿动物模型进行的体内实验也证实了这些作用。一些研究报告称,槲皮素能够干扰甲状腺激素的新陈代谢,因为它能抑制甲状腺和肝脏中5'-脱碘酶1型(D1)的活性。除了对正常甲状腺细胞的影响外,一些体外实验还显示了槲皮素对甲状腺癌的潜在治疗作用。事实上,槲皮素能抑制甲状腺癌细胞的生长、粘附和迁移,还能使一些甲状腺癌细胞株发生再分化。总之,这些数据表明,尽管槲皮素对甲状腺机能亢进症和甲状腺癌有一定疗效,但由于其抗甲状腺特性,在使用大剂量槲皮素时仍需谨慎。当然,还需要进一步的体内研究来证实这些假设。
{"title":"Quercetin and Thyroid.","authors":"Cesidio Giuliani, Giulia Di Dalmazi, Ines Bucci, Giorgio Napolitano","doi":"10.3390/antiox13101202","DOIUrl":"10.3390/antiox13101202","url":null,"abstract":"<p><p>Quercetin is the most abundant flavonoid present in fruits and vegetables. For its antiproliferative, antiviral, anti-inflammatory and antioxidants activities, it is an active ingredient of several herbal remedies and is available as a nutraceutical. Experimental studies performed in vitro have demonstrated that quercetin inhibits growth and function in normal thyroid cells and may act as a thyroid disruptor. These effects have also been confirmed in vivo using rodent models. Some studies have reported the ability of quercetin to interfere with the metabolism of thyroid hormones, since it inhibits the 5'-deiodinase type 1 (D1) activity in the thyroid, as well as in the liver. Besides the effects on normal thyroid cells, several experiments performed in vitro have shown a potential therapeutic role of quercetin in thyroid cancer. Indeed, quercetin inhibits the growth, the adhesion and the migration of thyroid cancer cells, and it also has redifferentiation properties in some thyroid cancer cell lines. In conclusion, these data suggest that, although its effects can be of benefit in hyperthyroidism and thyroid cancer, caution is required in the use of high doses of quercetin due to its anti-thyroid properties. Further in vivo studies are certainly needed to confirm these hypotheses.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11505551/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493435","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
DNA-Protective, Antioxidant and Anti-Carcinogenic Potential of Meadowsweet (Filipendula ulmaria) Dry Tincture. 绣线菊(Filipendula ulmaria)干酊剂的 DNA 保护、抗氧化和抗致癌性潜力。
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-03 DOI: 10.3390/antiox13101200
Tsvetelina Andonova, Yordan Muhovski, Elena Apostolova, Samir Naimov, Silviya Mladenova, Iliya Slavov, Ivayla Dincheva, Vasil Georgiev, Atanas Pavlov, Ivanka Dimitrova-Dyulgerova

Nowadays, interest in natural antioxidants (especially phenolics) for the prevention of oxidative stress-related diseases is increasing due to their fewer side effects and more potent activity than some of their synthetic analogues. New chemical and pharmacological studies of well-known herbal substances are among the current trends in medicinal plant research. Meadowsweet (Filipendula ulmaria) is a popular herb used in traditional medicine to treat various diseases (including rheumatic-, inflammatory- and tumor-related disease, etc.). The dry tincture of Filipendulae ulmariae herba, collected from the Bulgarian flora, was analyzed using the HPLC method and bioassayed for antioxidant, antiproliferative and DNA-protective activities against oxidative damage. The HPLC phenolic profile showed 12 phenolics, of which salicylic acid (18.84 mg/g dry extract), rutin (9.97 mg/g de), p-coumaric acid (6.80 mg/g de), quercetin (4.47 mg/g de), rosmarinic acid (4.01 mg/g de) and vanillic acid (3.82 mg/g de) were the major components. The high antioxidant potential of the species was confirmed by using four methods, best expressed by the results of the CUPRAC assay (10,605.91 μM TE/g de). The present study reports for the first time the highly protective activities of meadowsweet dry tincture against oxidative DNA damage and its antiproliferative effect against hepatocellular carcinoma (HepG2 cell line). Meadowsweet dry tincture possesses great potential to prevent diseases caused by oxidative stress.

如今,人们对天然抗氧化剂(尤其是酚类物质)预防氧化应激相关疾病的兴趣与日俱增,因为与某些合成类似物相比,天然抗氧化剂的副作用更小,活性更强。对知名草药物质进行新的化学和药理研究是当前药用植物研究的趋势之一。绣线菊(Filipendula ulmaria)是一种传统医学中常用的草药,可用于治疗多种疾病(包括风湿、炎症和肿瘤相关疾病等)。从保加利亚植物区系中采集的 Filipendulae ulmariae 草药干酊剂采用高效液相色谱法进行了分析,并进行了抗氧化、抗增殖和保护 DNA 免受氧化损伤的生物测定。高效液相色谱酚类谱图显示有 12 种酚类物质,其中水杨酸(18.84 毫克/克干提取物)、芦丁(9.97 毫克/克de)、对香豆酸(6.80 毫克/克de)、槲皮素(4.47 毫克/克de)、迷迭香酸(4.01 毫克/克de)和香草酸(3.82 毫克/克de)是主要成分。通过四种方法证实了该物种的高抗氧化潜力,其中以 CUPRAC 分析法的结果(10,605.91 μM TE/g de)最能说明问题。本研究首次报道了绣线菊干酊剂对 DNA 氧化损伤的高度保护活性及其对肝细胞癌(HepG2 细胞系)的抗增殖作用。绣线菊干酊剂在预防氧化应激引起的疾病方面具有巨大潜力。
{"title":"DNA-Protective, Antioxidant and Anti-Carcinogenic Potential of Meadowsweet (<i>Filipendula ulmaria</i>) Dry Tincture.","authors":"Tsvetelina Andonova, Yordan Muhovski, Elena Apostolova, Samir Naimov, Silviya Mladenova, Iliya Slavov, Ivayla Dincheva, Vasil Georgiev, Atanas Pavlov, Ivanka Dimitrova-Dyulgerova","doi":"10.3390/antiox13101200","DOIUrl":"10.3390/antiox13101200","url":null,"abstract":"<p><p>Nowadays, interest in natural antioxidants (especially phenolics) for the prevention of oxidative stress-related diseases is increasing due to their fewer side effects and more potent activity than some of their synthetic analogues. New chemical and pharmacological studies of well-known herbal substances are among the current trends in medicinal plant research. Meadowsweet (<i>Filipendula ulmaria</i>) is a popular herb used in traditional medicine to treat various diseases (including rheumatic-, inflammatory- and tumor-related disease, etc.). The dry tincture of <i>Filipendulae ulmariae herba</i>, collected from the Bulgarian flora, was analyzed using the HPLC method and bioassayed for antioxidant, antiproliferative and DNA-protective activities against oxidative damage. The HPLC phenolic profile showed 12 phenolics, of which salicylic acid (18.84 mg/g dry extract), rutin (9.97 mg/g de), <i>p</i>-coumaric acid (6.80 mg/g de), quercetin (4.47 mg/g de), rosmarinic acid (4.01 mg/g de) and vanillic acid (3.82 mg/g de) were the major components. The high antioxidant potential of the species was confirmed by using four methods, best expressed by the results of the CUPRAC assay (10,605.91 μM TE/g de). The present study reports for the first time the highly protective activities of meadowsweet dry tincture against oxidative DNA damage and its antiproliferative effect against hepatocellular carcinoma (HepG2 cell line). Meadowsweet dry tincture possesses great potential to prevent diseases caused by oxidative stress.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504252/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493280","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Facile One-Pot Conversion of (poly)phenols to Diverse (hetero)aryl Compounds by Suzuki Coupling Reaction: A Modified Approach for the Synthesis of Coumarin- and Equol-Based Compounds as Potential Antioxidants. 通过铃木偶联反应将(多)苯酚轻松一锅转化为多种(杂)芳基化合物:合成具有抗氧化潜力的香豆素和戊醇基化合物的改良方法。
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-03 DOI: 10.3390/antiox13101198
Muthipeedika Nibin Joy, Igor S Kovalev, Olga V Shabunina, Sougata Santra, Grigory V Zyryanov

A series of 16 (hetero)aryl compounds based on coumarin and equol has been efficiently synthesized by exploring the palladium-catalyzed Suzuki cross-coupling reactions. Polyphenol based on coumarin (4-methyl-7-hydroxy coumarin) was initially converted to corresponding coumarin imidazylate and then subjected to Suzuki coupling reaction with 4-methoxyphenylboronic acid to obtain the coupled product. This modified approach was later developed into a one-pot methodology by directly reacting the polyphenol with 1,1-sulfonyldiimidazole (SDI) and boronic acid in situ to obtain the Suzuki coupled product in one step. Moreover, an array of (poly)phenols based on coumarin and equol were later converted to diverse (hetero)aryl compounds by this optimized step-economic protocol. The synthesized compounds were then subjected to the screening of their potential antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In our investigation, the compounds 4ah, 4eh, 4gh and 4hh exhibited promising antioxidant potential when compared to the reference standard, butylated hydroxytoluene (BHT). Structure activity relationship (SAR) studies revealed the importance of the presence of electron-donating substituents in enhancing the antioxidant activity of the synthesized compounds.

通过探索钯催化的铃木交叉偶联反应,我们有效地合成了一系列基于香豆素和等醇的 16 种(杂)芳基化合物。以香豆素(4-甲基-7-羟基香豆素)为基础的多酚最初被转化为相应的香豆素亚酰胺酯,然后与 4-甲氧基苯硼酸进行铃木偶联反应,得到偶联产物。这种改良方法后来发展成了单锅方法,即直接将多酚与 1,1-磺酰基二咪唑(SDI)和硼酸原位反应,从而一步获得铃木偶联产物。此外,基于香豆素和等醇的一系列(多)酚后来也通过这种优化的经济型步骤转化成了多种(杂)芳基化合物。合成的化合物随后通过 2,2-二苯基-1-苦基肼(DPPH)检测法筛选其潜在的抗氧化活性。在我们的研究中,与参考标准丁基羟基甲苯(BHT)相比,化合物 4ah、4eh、4gh 和 4hh 表现出了良好的抗氧化潜力。结构活性关系(SAR)研究表明,电子供能取代基的存在对提高合成化合物的抗氧化活性非常重要。
{"title":"Facile One-Pot Conversion of (poly)phenols to Diverse (hetero)aryl Compounds by Suzuki Coupling Reaction: A Modified Approach for the Synthesis of Coumarin- and Equol-Based Compounds as Potential Antioxidants.","authors":"Muthipeedika Nibin Joy, Igor S Kovalev, Olga V Shabunina, Sougata Santra, Grigory V Zyryanov","doi":"10.3390/antiox13101198","DOIUrl":"10.3390/antiox13101198","url":null,"abstract":"<p><p>A series of 16 (hetero)aryl compounds based on coumarin and equol has been efficiently synthesized by exploring the palladium-catalyzed Suzuki cross-coupling reactions. Polyphenol based on coumarin (4-methyl-7-hydroxy coumarin) was initially converted to corresponding coumarin imidazylate and then subjected to Suzuki coupling reaction with 4-methoxyphenylboronic acid to obtain the coupled product. This modified approach was later developed into a one-pot methodology by directly reacting the polyphenol with 1,1-sulfonyldiimidazole (SDI) and boronic acid in situ to obtain the Suzuki coupled product in one step. Moreover, an array of (poly)phenols based on coumarin and equol were later converted to diverse (hetero)aryl compounds by this optimized step-economic protocol. The synthesized compounds were then subjected to the screening of their potential antioxidant activities by 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In our investigation, the compounds <b>4ah</b>, <b>4eh</b>, <b>4gh</b> and <b>4hh</b> exhibited promising antioxidant potential when compared to the reference standard, butylated hydroxytoluene (BHT). Structure activity relationship (SAR) studies revealed the importance of the presence of electron-donating substituents in enhancing the antioxidant activity of the synthesized compounds.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504026/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493317","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
NADPH Oxidase 5 (NOX5) Upregulates MMP-10 Production and Cell Migration in Human Endothelial Cells. NADPH 氧化酶 5 (NOX5) 上调人内皮细胞中 MMP-10 的生成和细胞迁移。
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-03 DOI: 10.3390/antiox13101199
Javier Marqués, Elena Ainzúa, Josune Orbe, María Martínez-Azcona, José Martínez-González, Guillermo Zalba

NADPH oxidases (NOXs) have been described as critical players in vascular remodeling, a mechanism modulated by matrix metalloproteinases. In this study, we describe for the first time the upregulation of MMP-10 through the activation of NOX5 in endothelial cells. In a chronic NOX5 overexpression model in human endothelial cells, MMP-10 production was measured at different levels: extracellular secretion, gene expression (mRNA and protein levels), and promoter activity. Effects on cell migration were quantified using wound healing assays. NOX5 overexpression increased MMP-10 production, favoring cell migration. In fact, NOX5 and MMP-10 silencing prevented this promigratory effect. We showed that NOX5-mediated MMP-10 upregulation involves the redox-sensitive JNK/AP-1 signaling pathway. All these NOX5-dependent effects were enhanced by angiotensin II (Ang II). Interestingly, MMP-10 protein levels were found to be increased in the hearts of NOX5-expressing mice. In conclusion, we described that NOX5-generated ROS may modulate the MMP-10 expression in endothelial cells, which leads to endothelial cell migration and may play a key role in vascular remodeling.

NADPH氧化酶(NOXs)被认为是血管重塑的关键因素,而这一机制是由基质金属蛋白酶调节的。在这项研究中,我们首次描述了通过激活内皮细胞中的 NOX5 上调 MMP-10。在人内皮细胞中的慢性 NOX5 过表达模型中,MMP-10 的产生在不同水平上进行了测量:细胞外分泌、基因表达(mRNA 和蛋白水平)和启动子活性。利用伤口愈合试验量化了对细胞迁移的影响。NOX5的过表达增加了MMP-10的产生,有利于细胞迁移。事实上,NOX5 和 MMP-10 的沉默能阻止这种迁移效应。我们发现,NOX5 介导的 MMP-10 上调涉及对氧化还原反应敏感的 JNK/AP-1 信号通路。血管紧张素 II(Ang II)增强了所有这些依赖于 NOX5 的效应。有趣的是,在表达 NOX5 的小鼠心脏中,MMP-10 蛋白水平升高。总之,我们描述了 NOX5 产生的 ROS 可调节内皮细胞中 MMP-10 的表达,从而导致内皮细胞迁移,并可能在血管重塑中发挥关键作用。
{"title":"NADPH Oxidase 5 (NOX5) Upregulates MMP-10 Production and Cell Migration in Human Endothelial Cells.","authors":"Javier Marqués, Elena Ainzúa, Josune Orbe, María Martínez-Azcona, José Martínez-González, Guillermo Zalba","doi":"10.3390/antiox13101199","DOIUrl":"10.3390/antiox13101199","url":null,"abstract":"<p><p>NADPH oxidases (NOXs) have been described as critical players in vascular remodeling, a mechanism modulated by matrix metalloproteinases. In this study, we describe for the first time the upregulation of MMP-10 through the activation of NOX5 in endothelial cells. In a chronic NOX5 overexpression model in human endothelial cells, MMP-10 production was measured at different levels: extracellular secretion, gene expression (mRNA and protein levels), and promoter activity. Effects on cell migration were quantified using wound healing assays. NOX5 overexpression increased MMP-10 production, favoring cell migration. In fact, NOX5 and MMP-10 silencing prevented this promigratory effect. We showed that NOX5-mediated MMP-10 upregulation involves the redox-sensitive JNK/AP-1 signaling pathway. All these NOX5-dependent effects were enhanced by angiotensin II (Ang II). Interestingly, MMP-10 protein levels were found to be increased in the hearts of NOX5-expressing mice. In conclusion, we described that NOX5-generated ROS may modulate the MMP-10 expression in endothelial cells, which leads to endothelial cell migration and may play a key role in vascular remodeling.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504164/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493400","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synergistic Dual Targeting of Thioredoxin and Glutathione Systems Irrespective of p53 in Glioblastoma Stem Cells. 与 p53 无关的硫氧还蛋白和谷胱甘肽系统在胶质母细胞瘤干细胞中的协同双重靶向作用
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-03 DOI: 10.3390/antiox13101201
Fatemeh Jamali, Katherine Lan, Paul Daniel, Kevin Petrecca, Siham Sabri, Bassam Abdulkarim

Glioblastoma (GBM) is an incurable primary brain cancer characterized by increased reactive oxygen species (ROS) production. The redox-sensitive tumor suppressor gene TP53, wild-type (wt) for 70% of patients, regulates redox homeostasis. Glioblastoma stem cells (GSCs) increase thioredoxin (Trx) and glutathione (GSH) antioxidant systems as survival redox-adaptive mechanisms to maintain ROS below the cytotoxic threshold. Auranofin, an FDA-approved anti-rheumatoid drug, inhibits thioredoxin reductase 1 (TrxR1). L-buthionine sulfoximine (L-BSO) and the natural product piperlongumine (PPL) inhibit the GSH system. We evaluated the cytotoxic effects of Auranofin alone and in combination with L-BSO or PPL in GBM cell lines and GSCs with a known TP53 status. The Cancer Genome Atlas/GBM analysis revealed a significant positive correlation between wtp53 and TrxR1 expression in GBM. Auranofin induced ROS-dependent cytotoxicity within a micromolar range in GSCs. Auranofin decreased TrxR1 expression, AKT (Ser-473) phosphorylation, and increased p53, p21, and PARP-1 apoptotic cleavage in wtp53-GSCs, while mutant-p53 was decreased in a mutant-p53 GSC line. Additionally, p53-knockdown in a wtp53-GSC line decreased TrxR1 expression and significantly increased sensitivity to Auranofin, suggesting the role of wtp53 as a negative redox-sensitive mechanism in response to Auranofin in GSCs. The combination of Auranofin and L-BSO synergistically increased ROS, decreased IC50s, and induced long-term cytotoxicity irrespective of p53 in GBM cell lines and GSCs. Intriguingly, Auranofin increased the expression of glutathione S-transferase pi-1 (GSTP-1), a target of PPL. Combining Auranofin with PPL synergistically decreased IC50s to a nanomolar range in GSCs, supporting the potential to repurpose Auranofin and PPL in GBM.

胶质母细胞瘤(GBM)是一种无法治愈的原发性脑癌,其特点是活性氧(ROS)生成增加。对氧化还原反应敏感的肿瘤抑制基因TP53(70%的患者为野生型)调节氧化还原平衡。胶质母细胞瘤干细胞(GSCs)会增加硫氧还蛋白(Trx)和谷胱甘肽(GSH)抗氧化系统,作为生存的氧化还原适应机制,将ROS维持在细胞毒性阈值以下。美国 FDA 批准的抗类风湿药物 Auranofin 可抑制硫氧还蛋白还原酶 1(TrxR1)。L-丁硫亚胺(L-BSO)和天然产物哌隆胺(PPL)抑制 GSH 系统。我们评估了奥拉诺芬单独使用以及与 L-BSO 或 PPL 联用对已知 TP53 状态的 GBM 细胞系和 GSC 的细胞毒性作用。癌症基因组图谱/GBM分析显示,GBM中wtp53和TrxR1的表达呈显著正相关。欧拉诺芬在微摩尔范围内诱导 GSCs 中的 ROS 依赖性细胞毒性。在wtp53-GSCs中,奥拉诺芬降低了TrxR1的表达、AKT(Ser-473)的磷酸化,并增加了p53、p21和PARP-1的凋亡裂解,而在突变体-p53 GSC系中,突变体-p53的表达也有所降低。此外,在 wtp53-GSC 株系中敲除 p53 会降低 TrxR1 的表达,并显著增加对 Auranofin 的敏感性,这表明 wtp53 在 GSCs 对 Auranofin 的反应中起着负氧化还原敏感机制的作用。欧拉诺芬和 L-BSO 的联合作用协同增加了 ROS,降低了 IC50,并诱导了 GBM 细胞系和 GSCs 的长期细胞毒性,而与 p53 无关。耐人寻味的是,Auranofin 增加了谷胱甘肽 S 转移酶 pi-1 (GSTP-1)的表达,而 GSTP-1 是 PPL 的靶标。Auranofin 与 PPL 协同作用可将 GSCs 中的 IC50 降至纳摩尔范围,这支持了将 Auranofin 和 PPL 重新用于 GBM 的潜力。
{"title":"Synergistic Dual Targeting of Thioredoxin and Glutathione Systems Irrespective of p53 in Glioblastoma Stem Cells.","authors":"Fatemeh Jamali, Katherine Lan, Paul Daniel, Kevin Petrecca, Siham Sabri, Bassam Abdulkarim","doi":"10.3390/antiox13101201","DOIUrl":"10.3390/antiox13101201","url":null,"abstract":"<p><p>Glioblastoma (GBM) is an incurable primary brain cancer characterized by increased reactive oxygen species (ROS) production. The redox-sensitive tumor suppressor gene <i>TP53</i>, wild-type (wt) for 70% of patients, regulates redox homeostasis. Glioblastoma stem cells (GSCs) increase thioredoxin (Trx) and glutathione (GSH) antioxidant systems as survival redox-adaptive mechanisms to maintain ROS below the cytotoxic threshold. Auranofin, an FDA-approved anti-rheumatoid drug, inhibits thioredoxin reductase 1 (TrxR1). L-buthionine sulfoximine (L-BSO) and the natural product piperlongumine (PPL) inhibit the GSH system. We evaluated the cytotoxic effects of Auranofin alone and in combination with L-BSO or PPL in GBM cell lines and GSCs with a known <i>TP53</i> status. The Cancer Genome Atlas/GBM analysis revealed a significant positive correlation between wtp53 and TrxR1 expression in GBM. Auranofin induced ROS-dependent cytotoxicity within a micromolar range in GSCs. Auranofin decreased TrxR1 expression, AKT (Ser-473) phosphorylation, and increased p53, p21, and PARP-1 apoptotic cleavage in wtp53-GSCs, while mutant-p53 was decreased in a mutant-p53 GSC line. Additionally, p53-knockdown in a wtp53-GSC line decreased TrxR1 expression and significantly increased sensitivity to Auranofin, suggesting the role of wtp53 as a negative redox-sensitive mechanism in response to Auranofin in GSCs. The combination of Auranofin and L-BSO synergistically increased ROS, decreased IC50s, and induced long-term cytotoxicity irrespective of p53 in GBM cell lines and GSCs. Intriguingly, Auranofin increased the expression of glutathione S-transferase pi-1 (GSTP-1), a target of PPL. Combining Auranofin with PPL synergistically decreased IC50s to a nanomolar range in GSCs, supporting the potential to repurpose Auranofin and PPL in GBM.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504866/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493448","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Melatonin's Impact on Wound Healing. 褪黑激素对伤口愈合的影响
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-02 DOI: 10.3390/antiox13101197
Eun-Hwa Sohn, Su-Nam Kim, Sung-Ryul Lee

Melatonin (5-methoxy-N-acetyltryptamine) is an indoleamine compound that plays a critical role in the regulation of circadian rhythms. While melatonin is primarily synthesized from the amino acid tryptophan in the pineal gland of the brain, it can also be produced locally in various tissues, such as the skin and intestines. Melatonin's effects in target tissues can be mediated through receptor-dependent mechanisms. Additionally, melatonin exerts various actions via receptor-independent pathways. In biological systems, melatonin and its endogenous metabolites often produce similar effects. While injuries are common in daily life, promoting optimal wound healing is essential for patient well-being and healthcare outcomes. Beyond regulating circadian rhythms as a neuroendocrine hormone, melatonin may enhance wound healing through (1) potent antioxidant properties, (2) anti-inflammatory actions, (3) infection control, (4) regulation of vascular reactivity and angiogenesis, (5) analgesic (pain-relieving) effects, and (6) anti-pruritic (anti-itch) effects. This review aims to provide a comprehensive overview of scientific studies that demonstrate melatonin's potential roles in supporting effective wound healing.

褪黑素(5-甲氧基-N-乙酰色胺)是一种吲哚胺化合物,在调节昼夜节律方面起着至关重要的作用。褪黑素主要由大脑松果体中的色氨酸氨基酸合成,也可在皮肤和肠道等多种组织中产生。褪黑素在目标组织中的作用可通过受体依赖机制介导。此外,褪黑激素还可通过与受体无关的途径发挥各种作用。在生物系统中,褪黑激素及其内源性代谢物通常会产生类似的作用。受伤在日常生活中很常见,促进伤口的最佳愈合对患者的健康和医疗效果至关重要。除了作为一种神经内分泌激素调节昼夜节律外,褪黑激素还可通过以下作用促进伤口愈合:(1)强效抗氧化特性;(2)抗炎作用;(3)感染控制;(4)调节血管反应性和血管生成;(5)镇痛作用;(6)止痒作用。本综述旨在全面概述证明褪黑激素在支持有效伤口愈合方面潜在作用的科学研究。
{"title":"Melatonin's Impact on Wound Healing.","authors":"Eun-Hwa Sohn, Su-Nam Kim, Sung-Ryul Lee","doi":"10.3390/antiox13101197","DOIUrl":"10.3390/antiox13101197","url":null,"abstract":"<p><p>Melatonin (5-methoxy-N-acetyltryptamine) is an indoleamine compound that plays a critical role in the regulation of circadian rhythms. While melatonin is primarily synthesized from the amino acid tryptophan in the pineal gland of the brain, it can also be produced locally in various tissues, such as the skin and intestines. Melatonin's effects in target tissues can be mediated through receptor-dependent mechanisms. Additionally, melatonin exerts various actions via receptor-independent pathways. In biological systems, melatonin and its endogenous metabolites often produce similar effects. While injuries are common in daily life, promoting optimal wound healing is essential for patient well-being and healthcare outcomes. Beyond regulating circadian rhythms as a neuroendocrine hormone, melatonin may enhance wound healing through (1) potent antioxidant properties, (2) anti-inflammatory actions, (3) infection control, (4) regulation of vascular reactivity and angiogenesis, (5) analgesic (pain-relieving) effects, and (6) anti-pruritic (anti-itch) effects. This review aims to provide a comprehensive overview of scientific studies that demonstrate melatonin's potential roles in supporting effective wound healing.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504849/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493380","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Biological Activity Assessment of 2-Styrylbenzothiazoles as Potential Multifunctional Therapeutic Agents. 作为潜在多功能治疗剂的 2-苯乙烯基苯并噻唑的合成和生物活性评估。
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-01 DOI: 10.3390/antiox13101196
Riccardo Barbari, Vera Bruggink, Robert Klaus Hofstetter, Chiara Tupini, Sofia Fagnani, Erika Baldini, Elisa Durini, Ilaria Lampronti, Silvia Vertuani, Anna Baldisserotto, Oliver Werz, Stefano Manfredini

A current trend in healthcare research is to discover multifunctional compounds, able to interact with multiple biological targets, in order to simplify multi-drug therapies and improve patient compliance. The aim of this work was to outline the growing demand for innovative multifunctional compounds, achieved through the synthesis, characterisation and SAR evaluation of a series of 2-styrylbenzothiazole derivatives. The six synthesised compounds were studied for their potential as photoprotective, antioxidant, antiproliferative, and anti-inflammatory agents. In order to profile antioxidant activity against various radical species, in vitro DPPH, FRAP and ORAC assays were performed. UV-filtering activity was studied, first in solution and then in formulation (standard O/W sunscreen containing 3% synthesised molecules) before and after irradiation. Compound BZTst6 proved to be photostable, suitable for broad-spectrum criteria, and is an excellent UVA filter. In terms of antioxidant activity, only compound BZTst4 can be considered a promising candidate, due to the potential of the catechol moiety. Both also showed exceptional inhibitory action against the pro-inflammatory enzyme 5-lipoxygenase (LO), with IC50 values in the sub-micromolar range in both activated neutrophils and under cell-free conditions. The results showed that the compounds under investigation are suitable for multifunctional application purposes, underlining the importance of their chemical scaffolding in terms of different biological behaviours.

目前医疗保健研究的一个趋势是发现能够与多个生物靶点相互作用的多功能化合物,以简化多种药物疗法并提高患者的依从性。这项研究的目的是通过一系列 2-苯乙烯基苯并噻唑衍生物的合成、表征和 SAR 评估,概述对创新型多功能化合物日益增长的需求。研究人员对合成的六种化合物进行了研究,以了解它们作为光保护剂、抗氧化剂、抗增殖剂和抗炎剂的潜力。为了分析针对各种自由基的抗氧化活性,研究人员进行了体外 DPPH、FRAP 和 ORAC 试验。研究了紫外线过滤活性,首先是在溶液中,然后是在配方中(含有 3% 合成分子的标准 O/W 防晒霜),然后是在照射前后。事实证明,化合物 BZTst6 具有光稳定性,适用于广谱标准,是一种出色的 UVA 过滤器。在抗氧化活性方面,由于儿茶酚分子的潜力,只有化合物 BZTst4 有希望成为候选化合物。这两种化合物对促炎酶 5-脂氧合酶(LO)也有特殊的抑制作用,在活化的中性粒细胞和无细胞条件下,其 IC50 值都在亚微摩尔范围内。研究结果表明,所研究的化合物适用于多功能应用目的,强调了其化学支架在不同生物行为方面的重要性。
{"title":"Synthesis and Biological Activity Assessment of 2-Styrylbenzothiazoles as Potential Multifunctional Therapeutic Agents.","authors":"Riccardo Barbari, Vera Bruggink, Robert Klaus Hofstetter, Chiara Tupini, Sofia Fagnani, Erika Baldini, Elisa Durini, Ilaria Lampronti, Silvia Vertuani, Anna Baldisserotto, Oliver Werz, Stefano Manfredini","doi":"10.3390/antiox13101196","DOIUrl":"10.3390/antiox13101196","url":null,"abstract":"<p><p>A current trend in healthcare research is to discover multifunctional compounds, able to interact with multiple biological targets, in order to simplify multi-drug therapies and improve patient compliance. The aim of this work was to outline the growing demand for innovative multifunctional compounds, achieved through the synthesis, characterisation and SAR evaluation of a series of 2-styrylbenzothiazole derivatives. The six synthesised compounds were studied for their potential as photoprotective, antioxidant, antiproliferative, and anti-inflammatory agents. In order to profile antioxidant activity against various radical species, in vitro DPPH, FRAP and ORAC assays were performed. UV-filtering activity was studied, first in solution and then in formulation (standard O/W sunscreen containing 3% synthesised molecules) before and after irradiation. Compound <b>BZTst6</b> proved to be photostable, suitable for broad-spectrum criteria, and is an excellent UVA filter. In terms of antioxidant activity, only compound <b>BZTst4</b> can be considered a promising candidate, due to the potential of the catechol moiety. Both also showed exceptional inhibitory action against the pro-inflammatory enzyme 5-lipoxygenase (LO), with IC<sub>50</sub> values in the sub-micromolar range in both activated neutrophils and under cell-free conditions. The results showed that the compounds under investigation are suitable for multifunctional application purposes, underlining the importance of their chemical scaffolding in terms of different biological behaviours.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504387/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493449","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Scavenging of Alkylperoxyl Radicals by Addition to Ascorbate: An Alternative Mechanism to Electron Transfer. 加入抗坏血酸清除烷基过氧自由基:电子转移的替代机制。
IF 6 2区 医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-10-01 DOI: 10.3390/antiox13101194
Gabriel Robert, J Richard Wagner

Vitamin C (ascorbate; Asc) is a biologically important antioxidant that scavenges reactive oxygen species such as deleterious alkylperoxyl radicals (ROO), which are generated by radical-mediated oxidation of biomolecules in the presence of oxygen. The radical trapping proprieties of Asc are conventionally attributed to its ability to undergo single-electron transfers with reactive species. According to this mechanism, the reaction between Asc and ROO results in the formation of dehydroascorbate (DHA) and the corresponding hydroperoxides (ROOH). When studying the reactivity of DNA 5-(2'-deoxyuridinyl)methylperoxyl radicals, we discovered a novel pathway of ROO scavenging by Asc. The purpose of this study is to elucidate the underlying mechanism of this reaction with emphasis on the characterization of intermediate and final decomposition products. We show that the trapping of ROO by Asc leads to the formation of an alcohol (ROH) together with an unstable cyclic oxalyl-l-threonate intermediate (cOxa-Thr), which readily undergoes hydrolysis into a series of open-chain oxalyl-l-threonic acid regioisomers. The structure of products was determined by detailed MS and NMR analyses. The above transformation can be explained by initial peroxyl radical addition (PRA) onto the C2=C3 enediol portion of Asc. Following oxidation of the resulting adduct radical, the product subsequently undergoes Baeyer-Villiger rearrangement, which releases ROH and generates the ring expansion product cOxa-Thr. The present investigation provides robust clarifications of the peroxide-mediated oxidation chemistry of Asc and DHA that has largely been obscured in the past by interference with autooxidation reactions and difficulties in analyzing and characterizing oxidation products. Scavenging of ROO by PRA onto Asc may have beneficial consequences since it directly converts ROO into ROH, which prevents the formation of potentially deleterious ROOH, although it induces the breakdown of Asc into fragments of oxalyl-l-threonic acid.

维生素 C(抗坏血酸;Asc)是一种重要的生物抗氧化剂,可清除活性氧,如有害的烷基过氧自由基(ROO-),这些自由基是生物大分子在氧气存在下通过自由基介导的氧化作用产生的。Asc 的自由基捕获特性通常归因于其与活性物种发生单电子转移的能力。根据这一机制,Asc 与 ROO- 反应后会形成脱氢抗坏血酸(DHA)和相应的氢过氧化物(ROOH)。在研究 DNA 5-(2'-脱氧尿苷基)甲基过氧自由基的反应性时,我们发现了 Asc 清除 ROO- 的新途径。本研究的目的是阐明这一反应的基本机理,重点是分析中间和最终分解产物的特征。我们的研究表明,Asc 清除 ROO- 的过程中会形成一种醇(ROH)和一种不稳定的环状草酰-L-苏氨酸中间体(cOxa-Thr),这种中间体很容易水解成一系列开链草酰-L-苏氨酸半异构体。通过详细的 MS 和 NMR 分析确定了产物的结构。Asc 的 C2=C3 烯二醇部分最初可通过过氧自由基加成(PRA)来解释上述转化。生成的加合物自由基被氧化后,产物随后发生拜耳-维利格重排,释放出 ROH 并生成扩环产物 cOxa-Thr。本研究有力地阐明了过氧化物介导的 Asc 和 DHA 氧化化学反应,过去由于自氧化反应的干扰以及氧化产物分析和表征的困难,这些化学反应在很大程度上被掩盖了。PRA 清除 Asc 上的 ROO- 可能会产生有益的结果,因为它能直接将 ROO- 转化为 ROH,从而防止形成可能有害的 ROOH,尽管它会诱导 Asc 分解为草酰苏氨酸片段。
{"title":"Scavenging of Alkylperoxyl Radicals by Addition to Ascorbate: An Alternative Mechanism to Electron Transfer.","authors":"Gabriel Robert, J Richard Wagner","doi":"10.3390/antiox13101194","DOIUrl":"10.3390/antiox13101194","url":null,"abstract":"<p><p>Vitamin C (ascorbate; Asc) is a biologically important antioxidant that scavenges reactive oxygen species such as deleterious alkylperoxyl radicals (ROO<sup>•</sup>), which are generated by radical-mediated oxidation of biomolecules in the presence of oxygen. The radical trapping proprieties of Asc are conventionally attributed to its ability to undergo single-electron transfers with reactive species. According to this mechanism, the reaction between Asc and ROO<sup>•</sup> results in the formation of dehydroascorbate (DHA) and the corresponding hydroperoxides (ROOH). When studying the reactivity of DNA 5-(2'-deoxyuridinyl)methylperoxyl radicals, we discovered a novel pathway of ROO<sup>•</sup> scavenging by Asc. The purpose of this study is to elucidate the underlying mechanism of this reaction with emphasis on the characterization of intermediate and final decomposition products. We show that the trapping of ROO<sup>•</sup> by Asc leads to the formation of an alcohol (ROH) together with an unstable cyclic oxalyl-l-threonate intermediate (cOxa-Thr), which readily undergoes hydrolysis into a series of open-chain oxalyl-l-threonic acid regioisomers. The structure of products was determined by detailed MS and NMR analyses. The above transformation can be explained by initial peroxyl radical addition (PRA) onto the C2=C3 enediol portion of Asc. Following oxidation of the resulting adduct radical, the product subsequently undergoes Baeyer-Villiger rearrangement, which releases ROH and generates the ring expansion product cOxa-Thr. The present investigation provides robust clarifications of the peroxide-mediated oxidation chemistry of Asc and DHA that has largely been obscured in the past by interference with autooxidation reactions and difficulties in analyzing and characterizing oxidation products. Scavenging of ROO<sup>•</sup> by PRA onto Asc may have beneficial consequences since it directly converts ROO<sup>•</sup> into ROH, which prevents the formation of potentially deleterious ROOH, although it induces the breakdown of Asc into fragments of oxalyl-l-threonic acid.</p>","PeriodicalId":7984,"journal":{"name":"Antioxidants","volume":null,"pages":null},"PeriodicalIF":6.0,"publicationDate":"2024-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11504153/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142493444","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
期刊
Antioxidants
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1