中文名 | 柚皮素 |
英文名 | (+|-)-naringenin |
别名 | 柚皮素 柚配基 柚(苷)配基 4',5,7-三羥黃酮 4',5,7-三羟基黄酮 4',5,7-三羟基黄烷酮 |
英文别名 | Naringenin -)-Naringenin TIMTEC-BB SBB006461 4,5,7-Trihydroxyflavone 4',5,7-Trihydroxyflavanone 5,7,4'-TRIHYDROXYFLAVANONE 5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE 5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one |
CAS | 93602-28-9 67604-48-2 |
EINECS | 266-769-1 |
化学式 | C15H12O5 |
分子量 | 272.25 |
熔点 | 247-250°C(lit.) |
沸点 | 577.5°Cat760mmHg |
溶解度 | 溶于乙醇、乙醚和苯,几乎不溶于水。 |
存储条件 | -20℃ |
外观 | 白色针状结晶 |
物化性质 | 柚皮素(4',5,7-三羟基二氢黄酮) 是柚皮苷水解掉一分子葡萄糖和鼠李糖得到的苷元图 1)。常温下为白色针状晶体,储存条件一般为阴凉干燥环境,熔点 247 ~ 250 ℃,由于其分子内含有苯环、羟基、羰基等官能团,所以在紫外区有吸收,无水乙醇中其紫外光谱在 288 nm 处有最大吸收,质谱(MRM) 检测,离子对为273.4/153.。柚皮素溶于乙醇、乙醚和苯,几乎不溶于水。盐酸镁粉反应呈樱红色,四氢硼钠反应呈红紫色,molish 反应阴性。脂溶性和水溶性不甚理想,通过引入脂溶性或水溶性较强的基团对其结构进行修 饰,可提高其脂溶性或水溶性,从而提高生物利度。其结构修饰主要包括羟基的烷基化、酰化、磺化、苷化及形成金属配合物等。 |
MDL号 | MFCD00006844 |
危险品标志 | Xi - 刺激性物品 |
风险术语 | 36/37/38 - 刺激眼睛、呼吸系统和皮肤。 |
安全术语 | S26 - 不慎与眼睛接触后,请立即用大量清水冲洗并征求医生意见。 S36 - 穿戴适当的防护服。 |
WGK Germany | 3 |
参考资料 展开查看 | 1. 李博. 合成8-二甲基异戊烯基柚皮素的人工酿酒酵母菌株构建[D].天津大学 2017. 2. 柯婷梅, 谌琪, 崔婷,等. 柚皮素对紫杉醇诱导外周神经病理性疼痛的保护作用[J]. 湖北科技学院学报(医学版), 2018, 032(004):280-282. 3. 刘金涛, 李玲, 董家吏,等. 柚皮素标准物质的研制及不确定度评定[J]. 分析测试学报, 2020, v.39(02):36-43. 4. 何小燕, 彭颖, 何婉莺,等. 柚皮素磷脂复合物的制备及其理化性质的研究[J]. 华中农业大学学报, 2019, 038(005):137-142. 5. 刘艳新, 李湘洲, 周军,等. 纤维素纳米晶体提升柚皮素抗氧化活性的研究[J]. 中国造纸, 38(9). 6. 余颖, 樊金玲, 程源斌,等. 甘草酸提取废液α-葡萄糖苷酶抑制剂的筛选与鉴定[J]. 食品科学, 2018, 39(13). 7. 柴瑞娟 雷金胜. Ce(NO3)3与4-香豆酸对黑曲霉合成黄酮类化合物的影响[J]. 中国稀土学报 2017(06):117-123. 8. 杨希娟, 党斌, 樊明涛. 溶剂提取对青稞中不同形态多酚组成及抗氧化活性的影响[J]. 食品科学, 2018, 39(24):246-255. 9. 詹志斌, 邓可众, 熊英,等. 高效液相色谱法同时测定枳实中6种成分的含量[J]. 中国医院药学杂志, 2015, 35(012):1080-1082. 10. 芦海生,李婷,姜丹,孙宇峰,常晓茜,胡小松,刘春生.基于DNA条形码、UPLC及色度学方法鉴定与评价化橘红[J].中国中药杂志,2019,44(20):4419-4425. 11. 高喜梅, 池玉梅, 张雯,等. 指纹图谱结合一测多评法评价酸橙枳实质量的研究[J]. 中草药, 2020, v.51;No.668(09):281-289. 12. 邓可众 邓敏芝 熊英 等. HPLC法同时分析酸橙果实类药材中黄酮和香豆素类成分[J]. 中药材 2016年39卷3期 575-578页 MEDLINE ISTIC PKU 2016. 13. 谢辉 陈亚 雷爱玲 等. SPE-HPLC-DAD法同时检测柑橘药用资源中黄烷酮类和川陈皮素成分[J]. 天然产物研究与开发 2019(8). 14. 崔欣悦 凌空 周明 等. 乳酸菌发酵柑橘皮的工艺研究及优化[J]. 食品研究与开发 2019 40(08):135-142. 15. 蔡爽, 阮成江, 杜维,等. 高效液相色谱-串联质谱法同时测定沙棘中的11种黄酮类物质[J]. 分析科学学报, 2019, 035(003):311-316. 16. 黑青稞麸皮结合态酚类物质大孔树脂分离纯化工艺优化 17. 黄旭,田苗苗,肖妃垚,刘娟,王振,单杨.柑橘香橙素生成途径关键酶黄烷酮-3-羟化酶特性分析及原核表达[J].食品科学技术学报,2021,39(02):65-72. 18. 常冠华,薄颖异,崔洁,徐露露,赵梓邯,王文全,侯俊玲.基于UPLC-Q-Exactive Orbitrap-MS分析甘草地上部分主要化学成分[J].中国中药杂志,2021,46(06):1449-1459. 19. 徐艳阳,赵玉娟,高峰,王二雷,鲁海玲,李雪凤,姜雯雯,陈艳.高效液相色谱法分析中国人参不同部位中多酚类化合物[J].食品科学,2021,42(04):240-246. 20. 赵萌萌,张文刚,党斌,杨希娟,张杰,甘生智.超微粉碎对青稞麸皮粉多酚组成及抗氧化活性的影响[J].农业工程学报,2020,36(15):291-298. 21. Cui, Yongliang, et al. "Development of a sensitive monoclonal antibody-based indirect competitive enzyme-linked immunosorbent assay for analysing nobiletin in citrus and herb samples." Food chemistry 293 (2019): 144-150.https://doi.org/10.1016/j.foodchem.2 22. He, Wei, et al. "Flavonoids from Citrus aurantium ameliorate TNBS-induced ulcerative colitis through protecting colonic mucus layer integrity." European journal of pharmacology 857 (2019): 172456.https://doi.org/10.1016/j.ejphar.2019.172456 23. Zhu, Bo, et al. "Fungal elicitors stimulate biomass and active ingredients accumulation in Dendrobium catenatum plantlets." Biologia 73.10 (2018): 917-926.https://doi.org/10.2478/s11756-018-0091-9 24. Hengqiang Zhao, Minmin Zhang, Qian Liu, Xiaoli Wang, Ruixuan Zhao, Yanling Geng, Tityee Wong, Shengbo Li & Xiao Wang (2018) A comprehensive screening shows that ergothioneine is the most abundant antioxidant in the wild macrofungus Phylloporia ribis Ryvard 25. Guo, Xiao, et al. "Intestinal absorption and distribution of naringin, hesperidin, and their metabolites in mice." Journal of Functional Foods 74 (2020): 104158.https://doi.org/10.1016/j.jff.2020.104158 26. He, Wei, et al. "Citrus aurantium L. and its flavonoids regulate TNBS-induced inflammatory bowel disease through anti-inflammation and suppressing isolated jejunum contraction." International journal of molecular sciences 19.10 (2018): 3057.https://doi.org 27. Yang, Yang, et al. "Deciphering the multicomponent synergy mechanism from a systems pharmacology perspective: application to Gualou Xiebai decoction for coronary heart disease." Journal of Functional Foods 47 (2018): 143-155.https://doi.org/10.1016/j.jff.2 28. Pei Pu, Xin Zheng, Linna Jiao, Lang Chen, Han Yang, Yonghong Zhang, Guizhao Liang, Six flavonoids inhibit the antigenicity of β-lactoglobulin by noncovalent interactions: A spectroscopic and molecular docking study, Food Chemistry, Volume 339, 2021, 128106 29. Gao, Mingliang, et al. "Evaluation of VEGF mediated pro-angiogenic and hemostatic effects and chemical marker investigation for Typhae Pollen and its processed product." Journal of Ethnopharmacology 268 (2021): 113591.https://doi.org/10.1016/j.jep.2020.113 30. Lyu, Yunbin, et al. "Identification and characterization of three flavonoid 3-O-glycosyltransferases from Epimedium koreanum Nakai." Biochemical Engineering Journal 163 (2020): 107759.https://doi.org/10.1016/j.bej.2020.107759 31. Tan, Si, et al. "Lycopene, polyphenols and antioxidant activities of three characteristic tomato cultivars subjected to two drying methods." Food Chemistry 338 (2021): 128062.https://doi.org/10.1016/j.foodchem.2020.128062 32. Hengqiang Zhao, Minmin Zhang, Qian Liu, Xiaoli Wang, Ruixuan Zhao, Yanling Geng, Tityee Wong, Shengbo Li & Xiao Wang (2018) A comprehensive screening shows that ergothioneine is the most abundant antioxidant in the wild macrofungus Phylloporia ribis Ryvard 33. [IF=7.808] Jianhua Li et al."Production of plant-specific flavones baicalein and scutellarein in an engineered E. coli from available phenylalanine and tyrosine."Metab Eng. 2019 Mar;52:124 34. [IF=5.81] Zhang Xianhua et al."Pharmacokinetic Study of 7 Compounds Following Oral Administration of Fructus Aurantii to Depressive Rats."Front Pharmacol. 2018 Mar;0:131 35. [IF=5.279] Yingying Wei et al."Hot Air Treatment Induces Disease Resistance through Activating the Phenylpropanoid Metabolism in Cherry Tomato Fruit."J Agr Food Chem. 2017;65(36):8003–8010 36. [IF=4.556] Wei He et al."Citrus aurantium L. and Its Flavonoids Regulate TNBS-Induced Inflammatory Bowel Disease through Anti-Inflammation and Suppressing Isolated Jejunum Contraction."Int J Mol Sci. 2018 Oct;19(10):3057 37. [IF=4.451] Yang Yang et al."Deciphering the multicomponent synergy mechanism from a systems pharmacology perspective: Application to Gualou Xiebai Decoction for coronary heart disease."J Funct Foods. 2018 Aug;47:143 38. [IF=4.411] Xiaosheng Tang et al."Molecular Structure–Affinity Relationship of Flavonoids in Lotus Leaf (Nelumbo nucifera Gaertn.) on Binding to Human Serum Albumin and Bovine Serum Albumin by Spectroscopic Method."Molecules. 2017 Jul;22(7):1036 39. [IF=4.142] Tao Yi et al."Ultrafiltration coupled with high-performance liquid chromatography and quadrupole-time-of-flight mass spectrometry for screening lipase binders from different extracts of Dendrobium officinale."Anal Bioanal Chem. 2015 Aug;407(20):6081-6093 40. [IF=3.738] Selma Houchi et al."Investigation of common chemical components and inhibitory effect on GES-type β-lactamase (GES22) in methanolic extracts of Algerian seaweeds."Microb Pathogenesis. 2019 Jan;126:56 41. [IF=1.35] Zhu Bo et al."Fungal elicitors stimulate biomass and active ingredients accumulation in Dendrobium catenatum plantlets."Biologia. 2018 Oct;73(10):917-926 42. [IF=10.182] Yucong Zou et al."Highly efficient bioconversion of flavonoid glycosides from citrus-processing wastes in solvent-buffer systems."Green Chem. 2020 May;22(10):3196-3207 43. [IF=7.514] Yongliang Cui et al."Development of a sensitive monoclonal antibody-based indirect competitive enzyme-linked immunosorbent assay for analysing nobiletin in citrus and herb samples."Food Chem. 2019 Sep;293:144 44. [IF=7.514] Pei Pu et al."Six flavonoids inhibit the antigenicity of β-lactoglobulin by noncovalent interactions: A spectroscopic and molecular docking study."Food Chem. 2021 Mar;339:128106 45. [IF=7.514] Jing Zhao et al."A sensitive and practical ELISA for analyzing naringenin in pummelo and herb samples."Food Chem. 2021 Nov;362:130223 46. [IF=6.543] Wang Yue et al."Polymethoxyflavones in Citrus Regulate Lipopolysaccharide-Induced Oscillating Decay of Circadian Rhythm Genes by Inhibiting Nlrp3 Expression."Oxid Med Cell Longev. 2021;2021:8419415 47. [IF=5.64] Ji Xuemeng et al."Function Characterization of Endogenous Plasmids in Cronobacter sakazakii and Identification of p-Coumaric Acid as Plasmid-Curing Agent."Front Microbiol. 2021 Jun;0:1589 48. [IF=5.537] Mengjie Kong et al."Effect of high-pressure carbon dioxide treatment on browning inhibition of fresh-cut Chinese water chestnut (Eleocharis tuberosa): Based on the comparison of damaged tissue and non-damaged tissue."Postharvest Biol Tec. 2021 Sep;179:111 49. [IF=5.34] Jing Zhang et al."Application of “spider-web” mode in discovery and identification of Q-markers from Xuefu Zhuyu capsule."Phytomedicine. 2020 Oct;77:153273 50. [IF=5.279] Chengcheng Sun et al."Enhancing Flavan-3-ol Biosynthesis in Saccharomyces cerevisiae."J Agr Food Chem. 2021;69(43):12763–12772 51. [IF=5.279] Feng Wang et al."Four Citrus Flavanones Exert Atherosclerosis Alleviation Effects in ApoE–/– Mice via Different Metabolic and Signaling Pathways."J Agr Food Chem. 2021;69(17):5226–5237 52. [IF=5.279] Qinggang Yin et al."Identification of Specific Glycosyltransferases Involved in Flavonol Glucoside Biosynthesis in Ginseng Using Integrative Metabolite Profiles, DIA Proteomics, and Phylogenetic Analysis."J Agr Food Chem. 2021;69(5):1714–1726 53. [IF=4.879] Yang Liu et al."UV-B Radiation Largely Promoted the Transformation of Primary Metabolites to Phenols in Astragalus mongholicus Seedlings."Biomolecules. 2020 Apr;10(4):504 54. [IF=4.653] Qiang Zhao et al."Naringenin Exerts Cardiovascular Protective Effect in a Palmitate‐Induced Human Umbilical Vein Endothelial Cell Injury Model via Autophagy Flux Improvement."Mol Nutr Food Res. 2019 Dec;63(24):1900601 55. [IF=4.451] Xiao Guo et al."Intestinal absorption and distribution of naringin, hesperidin, and their metabolites in mice."J Funct Foods. 2020 Nov;74:104158 56. [IF=4.432] Wei He et al."Flavonoids from Citrus aurantium ameliorate TNBS-induced ulcerative colitis through protecting colonic mucus layer integrity."Eur J Pharmacol. 2019 Aug;857:172456 57. [IF=4.411] Liuyi Yu et al."Systematic Detection and Identification of Bioactive Ingredients from Citrus aurantium L. var. amara Using HPLC-Q-TOF-MS Combined with a Screening Method."Molecules. 2020 Jan;25(2):357 58. [IF=4.407] Jie Yang et al."Naringenin inhibits pro‑inflammatory cytokine production in macrophages through inducing MT1G to suppress the activation of NF‑κB."Mol Immunol. 2021 Sep;137:155 59. [IF=4.36] Mingliang Gao et al."Evaluation of VEGF mediated pro-angiogenic and hemostatic effects and chemical marker investigation for Typhae Pollen and its processed product."J Ethnopharmacol. 2021 Mar;268:113591 60. [IF=4.35] Yanpeng Hao et al."Biotransformation of Flavonoids Improves Antimicrobial and Anti-Breast Cancer Activities In Vitro."Foods. 2021 Oct;10(10):2367 61. [IF=4.24] Mingxia Wu et al."Inhibitory effects of acorn (Quercus variabilis Blume) kernel-derived polyphenols on the activities of α-amylase, α-glucosidase, and dipeptidyl peptidase IV."Food Biosci. 2021 Oct;43:101224 62. [IF=3.935] Jingyun Zheng et al."A systematic investigation on free phenolic acids and flavonoids profiles of commonly consumed edible flowers in China."J Pharmaceut Biomed. 2019 Aug;172:268 63. [IF=3.935] Yong-liang Zhu et al."Simultaneous determination of six components of Danzhi Xiaoyao Pill in beagle plasma by HPLC-MS/MS and a study of pharmacokinetic of paeoniflorin and geniposide after single-dose administration."J Pharmaceut Biomed. 2020 Jul;186:1132 64. [IF=3.411] Shi Guiqin et al."UPLC-ESI-MS/MS Analysis and Evaluation of Antioxidant Activity of Total Flavonoid Extract from Paeonia lactiflora Seed Peel and Optimization by Response Surface Methodology (RSM)."Biomed Res Int. 2021;2021:7304107 65. [IF=3.361] Mengmeng Yuan et al."The interaction of dietary flavonoids with xanthine oxidase in vitro: molecular property-binding affinity relationship aspects."Rsc Adv. 2019 Apr;9(19):10781-10788 66. [IF=3.361] Yanhui Zhao et al."Rapid characterization of the chemical constituents of Sanhua decoction by UHPLC coupled with Fourier transform ion cyclotron resonance mass spectrometry."Rsc Adv. 2020 Jul;10(44):26109-26119 67. [IF=2.633] Ruoke Ma et al."Variation of Chemical Components in Sapwood, Transition Zone, and Heartwood of Dalbergia odorifera and Its Relationship with Heartwood Formation."Forests. 2021 May;12(5):577 68. [IF=2.461] Yang Qian et al."The disruption of the MAPKK gene triggering the synthesis of flavonoids in endophytic fungus Phomopsis liquidambaris."Biotechnol Lett. 2021 Jan;43(1):119-132 69. [IF=2.391] Tan Si et al."Effects of three drying methods on polyphenol composition and antioxidant activities of Litchi chinensis Sonn.."Food Sci Biotechnol. 2020 Mar;29(3):351-358 70. [IF=2.193] Zhu Yong-liang et al."Simultaneous Determination of Five Components of Chaihu-Shugan-San in Beagle Plasma by HPLC-MS/MS and Its Application to a Pharmacokinetic Study after a Single Dose of Chaihu-Shugan-San."J Anal Methods Chem. 2020;2020:8831938 71. [IF=2.19] Sheng-xiang Yang et al."Extraction of flavonoids from Cyclocarya paliurus (Juglandaceae) leaves using ethanol/salt aqueous two-phase system coupled with ultrasonic."J Food Process Pres. 2020 Jun;44(6):e14469 72. [IF=1.524] Zhang Xiaodong et al."Gene polymorphism of chalcone isomerase influence the accumulation of flavonoids in licorice (Glycyrrhiza spp.)."Genet Resour Crop Ev. 2021 Mar;68(3):899-913 73. [IF=1.296] Shen Ting et al."Pigment profile and gene analysis revealed the reasons of petal color difference of crabapples."Braz J Bot. 2021 Jun;44(2):287-296 74. [IF=4.379] Zhang Lulu et al.Systems pharmacology to reveal multi-scale mechanisms of traditional Chinese medicine for gastric cancer.Sci Rep-Uk. 2021 Nov;11(1):1-12 75. [IF=2.629] Mu Qixuan et al."Study on Closely Related Citrus CMMs based on Chemometrics and Prediction of Components-Targets-Diseases Network by Ingenuity Pathway Analysis."Evid-Based Compl Alt. 2022;2022:1106353 76. [IF=3.638] Wenfeng Li et al."Zein enhanced the digestive stability of five citrus flavonoids via different binding interaction."Journal Of The Science Of Food And Agriculture. 2022 Mar 09 77. [IF=5.165] Juanning Ren et al."Qualitative and quantitative analysis of multi-components in Xing-Su-Ning Capsules for quality improvement."Arab J Chem. 2022 Jun;15:103825 78. [IF=6.475] Jinxin Li et al."Trapping of reactive carbonyl species by fiber-bound polyphenols from whole grains under simulated physiological conditions."Food Res Int. 2022 Jun;156:111142 79. [IF=3.307] Juan Liu et al."Production of hesperetin from naringenin in an engineered Escherichia coli consortium."J Biotechnol. 2022 Mar;347:67 80. [IF=3.833] Xiao Guo et al."Involvement of phase II enzymes and efflux transporters in the metabolism and absorption of naringin, hesperidin and their aglycones in rats."International Journal Of Food Sciences And Nutrition. 2022 Jan 02 81. [IF=3.935] Junmao Li et al."Comprehensive chemical profiling of the flowers of Citrus aurantium L. var. amara Engl. and uncovering the active ingredients of lipid lowering."J Pharmaceut Biomed. 2022 Mar;211:114621 82. [IF=4.57] Liu Jinyue et al."Identification and characterization of unique 5-hydroxyisoflavonoid biosynthetic key enzyme genes in Lupinus albus."Plant Cell Reports. 2021 Dec 01 83. [IF=4.412] Haifan Liu et al."Pharmacokinetics, Prostate Distribution and Metabolic Characteristics of Four Representative Flavones after Oral Administration of the Aerial Part of Glycyrrhiza uralensis in Rats."MOLECULES. 2022 Jan;27(10):3245 84. [IF=4.412] Hui-Min Jin et al."Polyphenol and Anthocyanin Composition and Activity of Highland Barley with Different Colors."MOLECULES. 2022 Jan;27(11):3411 85. [IF=5.34] Mingliang Gao et al."Discovery of processing-associated Q-marker of carbonized traditional Chinese medicine: an integrated strategy of metabolomics, systems pharmacology and in vivo high-throughput screening model."PHYTOMEDICINE. 2022 May;:154152 86. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 87. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure–Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 88. [IF=3.713] Ren Li et al."Effects of germination time on phenolics, antioxidant capacity, in vitro phenolic bioaccessibility and starch digestibility in sorghum."INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY |
微信搜索化工百科或扫描下方二维码,添加化工百科小程序,随时随地查信息!