Research progress on new extraction technologies and bioactivities of flavonoids from orange

Authors

LIU Dan, School of Food and Biological Engineering, Chengdu University, Chengdu, Sichuan 610106 , China ；Institute of Urban Agriculture, Chinese Academy of Agricultural Sciences, Chengdu, Sichuan 610213 , China
GUO Huan, Institute of Urban Agriculture, Chinese Academy of Agricultural Sciences, Chengdu, Sichuan 610213 , China
WU Di, School of Food and Biological Engineering, Chengdu University, Chengdu, Sichuan 610106 , China
GAN Ren-you, School of Food and Biological Engineering, Chengdu University, Chengdu, Sichuan 610106 , China ；Institute of Urban Agriculture, Chinese Academy of Agricultural Sciences, Chengdu, Sichuan 610213 , China ；Chengdu National Agricultural Science & Technology Center, Chengdu, Sichuan 610213 , China

Abstract

The new extraction technologies of citrus flavonoids in recent five years were reviewed, including low eutectic solvent extraction, subcritical fluid extraction and magnetic molecular blot selective extraction.the bioactivities and mechanisms of citrus flavonoids, such as antioxidant, anti-inflammatory, antibacterial, anti-obesity, anti-diabetes, anti-cancer, intestinal protection, cardiovascular protection, liver protection and neuroprotection, were also expounded, and suggestions for further study of citrus flavonoids were proposed.

Publication Date

12-15-2022

First Page

217

Last Page

224

DOI

10.13652/j.spjx.1003.5788.2022.90234

Recommended Citation

Dan, LIU; Huan, GUO; Di, WU; and Ren-you, GAN (2022) "Research progress on new extraction technologies and bioactivities of flavonoids from orange," Food and Machinery: Vol. 38: Iss. 11, Article 35.
DOI: 10.13652/j.spjx.1003.5788.2022.90234
Available at: https://www.ifoodmm.cn/journal/vol38/iss11/35

References

[1] 祁建宏,董芳旭.黄酮类化合物药理作用研究进展[J].北京联合大学学报,2020,34(3):89-92.QI J H,DONG F X.Research progress on pharmacological action of flavonoids[J].Journal of Beijing Union University,2020,34(3):89-92.
[2] 成洪业,漆志文.低共熔溶剂用于萃取分离的研究进展[J].化工进展,2020,39(12):4 896-4 907.CHENG H Y,QI Z W.Research progress of deep eutectic solvent for extractive separation[J].Chemical Industry and Engineering Progress,2020,39(12):4 896-4 907.
[3] XU M,RAN L,CHEN N,et al.Polarity-dependent extraction of flavonoids from Citrus peel waste using a tailor-made deep eutectic solvent[J].Food Chemistry,2019,297:124970.
[4] JOKIC S,AFRANKO S,JAKOVLJEVIC M,et al.Sustainable green procedure for extraction of hesperidin from selected Croatian mandarin peels[J].Processes,2019,7(7):469.
[5] 谢豪,黄龙,王萍,等.亚临界萃取结合分子蒸馏提取甜橙油的研究[J].食品工业,2019,40(3):78-82.XIE H,HUANG L,WANG P,et al.Study on the essential oil extraction from Citrus sinensis by subcritical extraction combining with molecular distillation[J].The Food Industry,2019,40(3):78-82.
[6] KIM D S,LIM S B.Semi-continuous subcritical water extraction of flavonoids from Citrus unshiu peel:Their antioxidant and enzyme inhibitory activities[J].Antioxidants(Basel),2020,9(5):360.
[7] LACHOS-PEREZ D,BASEGGIO A M,MAYANGA-TORRES P C,et al.Subcritical water extraction of flavanones from defatted orange peel[J].The Journal of Supercritical Fluids,2018,138:7-16.
[8] 杨霄鸿,贾明宏,杨天予,等.分子印迹技术在农药残留检测中的应用进展[J].食品安全质量检测学报,2017,8(2):462-467.YANG X H,JIA M H,YANG T Y,et al.Progress of molecular imprinting technique on the determination of pesticides residues[J].Journal of Food Safety and Quality,2017,8(2):462-467.
[9] 张曦雯,李兆周,李道敏,等.磁性分子印迹聚合物的制备与应用研究[J].化工进展,2016,35(12):3 964-3 969.ZHANG X W,LI Z Z,LI D M,et al.Preparation and application of magnetic molecularly imprinted polymer[J].Chemical Industry and Engineering Progress,2016,35(12):3 964-3 969.
[10] 贺美艳.类黄酮分子印迹聚合物的合成及其在柑橘中识别性能的研究[D].重庆:西南大学,2017:17-54.HE M Y.Study on synthesis and molecular recognition of flavonoids molecularly imprinted polymers in Citrus[D].Chongqing:Southwest University,2017:17-54.
[11] WANG D D,GAO D,XU W J,et al.Magnetic molecularly imprinted polymer for the selective extraction of hesperetin from the dried pericarp of Citrus reticulata Blanco[J].Talanta,2018,184:307-315.
[12] LIU F,HAN S,NI Y.Isolation and purification of four flavanones from peel of Citrus changshanensis[J].Journal of Food Processing and Preservation,2017,41(6):e13278.
[13] SUBHI SAMMANI M,CLAVIJO S,FIGUEROLA A,et al.3D printed structure coated with C18 particles in an online flow system coupled to HPLC-DAD for the determination of flavonoids in Citrus external peel[J].Microchemical Journal,2021,168:106421.
[14] GUO C,SHAN Y,YANG Z,et al.Chemical composition,antioxidant,antibacterial,and tyrosinase inhibition activity of extracts from Newhall navel orange(Citrus sinensis Osbeck cv.Newhall)peel[J].Journal of the Science of Food and Agriculture,2020,100(6):2 664-2 674.
[15] 郭春霞.4类重庆柑橘乙醇提取物类黄酮分析及其体内外抗氧化评价[J].安徽农业科学,2018,46(22):149-153.GUO C X.Flavonoids composition of the ethanol extracts of four Citrus in Chongqing and their in vitro and in vivo antioxidant activities[J].Journal of Anhui Agricultural Sciences,2018,46(22):149-153.
[16] FERLAZZO N,VISALLI G,CIRMI S,et al.Natural iron chelators:Protective role in A549 cells of flavonoids-rich extracts of Citrus juices in Fe3+-induced oxidative stress[J].Environmental Toxicology and Pharmacology,2016,43:248-256.
[17] LIU W Y,LIOU S S,HONG T Y,et al.The benefits of the Citrus flavonoid diosmin on human retinal pigment epithelial cells under high-glucose conditions[J].Molecules,2017,22(12):2 251.
[18] LIU X,WANG N,FAN S,et al.The Citrus flavonoid naringenin confers protection in a murine endotoxaemia model through AMPK-ATF3-dependent negative regulation of the TLR4 signalling pathway[J].Scientific Reports,2016,6:39735.
[19] RONG X,XU J,JIANG Y,et al.Citrus peel flavonoid nobiletin alleviates lipopolysaccharide-induced inflammation by activating IL-6/STAT3/FOXO3a-mediated autophagy[J].Food & Function,2021,12(3):1 305-1 317.
[20] HE W,LI Y,LIU M,et al.Citrus aurantium L.and its flavonoids regulate tnbs-induced inflammatory bowel disease through anti-inflammation and suppressing isolated jejunum contraction[J].International Journal of Molecular Sciences,2018,19(10):3 057.
[21] YANG W L,CHEN S Y,HO C Y,et al.Citrus flavonoids suppress IL-5 and ROS through distinct pathways in PMA/ionomycin-induced EL-4 cells[J].Food & Function,2020,11(1):824-833.
[22] WANG J,LI T,CAI H,et al.Protective effects of total flavonoids from Qu Zhi Qiao(fruit of Citrus paradisi cv.Changshanhuyou)on OVA-induced allergic airway inflammation and remodeling through MAPKs and Smad2/3 signaling pathway[J].Biomedicine & Pharmacotherapy,2021,138:111421.
[23] CARVALHO J S,RAMADAN D,DE PAIVA GONCALVES V,et al.Impact of Citrus flavonoid supplementation on inflammation in lipopolysaccharide-induced periodontal disease in mice[J].Food & Function,2021,12(11):5 007-5 017.
[24] SATHIYA DEEPIKA M,THANGAM R,SAKTHIDHASAN P,et al.Combined effect of a natural flavonoid rutin from Citrus sinensis and conventional antibiotic gentamicin on Pseudomonas aeruginosa biofilm formation[J].Food Control,2018,90:282-294.
[25] WANG L H,WANG M S,ZENG X A,et al.Membrane and genomic DNA dual-targeting of Citrus flavonoid naringenin against Staphylococcus aureus[J].Integrative Biology,2017,9(10):820-829.
[26] ROMER VILLUMSEN K,OHTANI M,FORBERG T,et al.Citrus flavonoids,β-glucan and organic acid feed additives decrease relative risk during Yersinia ruckeri O1 biotype 2 infection of rainbow trout(Oncorhynchus mykiss)[J].Peer J,2020,8:e8706.
[27] BUSTANJI Y,AL-MASRI I M,MOHAMMAD M,et al.Pancreatic lipase inhibition activity of trilactone terpenes of Ginkgo biloba[J].Journal of Enzyme Inhibition and Medicinal Chemistry,2011,26(4):453-459.
[28] 黄睿.柑橘类黄酮分光测定法比较及其抗氧化与胰脂肪酶抑制功效评价[D].杭州:浙江大学,2019.HUANG R.Comparison of spectrophotometry of Citrus flavonoids and evaluation of their antioxidant and pancreatic lipase inhibitory activities[D].Hangzhou:Zhejiang University,2019.
[29] 孔宇驰.三种柑橘黄酮与消化相关酶的相互作用机理研究[D].沈阳:辽宁大学,2020:47-63.KONG Y C.Study on the interaction mechanism between three Citrus flavonoids and digestive enzymes[D].Shenyang:Liaoning University,2020:47-63.
[30] SU D,LIU H,QI X,et al.Citrus peel flavonoids improve lipid metabolism by inhibiting miR-33 and miR-122 expression in HepG2 cells[J].Bioscience,Biotechnology,and Biochemistry,2019,83(9):1 747-1 755.
[31] MONTALBANO G,MANIA M,GUERRERA M C,et al.Effects of a flavonoid-rich extract from Citrus sinensis juice on a diet-induced obese zebrafish[J].International Journal of Molecular Sciences,2019,20(20):5 116.
[32] MORROW N M,BURKE A C,SAMSOONDAR J P,et al.The Citrus flavonoid nobiletin confers protection from metabolic dysregulation in high-fat-fed mice independent of AMPK[J].Journal of Lipid Research,2020,61(3):387-402.
[33] BURKE A C,SUTHERLAND B G,TELFORD D E,et al.Intervention with Citrus flavonoids reverses obesity and improves metabolic syndrome and atherosclerosis in obese Ldlr-/-mice[J].Journal of Lipid Research,2018,59(9):1 714-1 728.
[34] KE J Y,COLE R M,HAMAD E M,et al.Citrus flavonoid,naringenin,increases locomotor activity and reduces diacylglycerol accumulation in skeletal muscle of obese ovariectomized mice[J].Molecular Nutrition & Food Research,2016,60(2):313-324.
[35] ALI M Y,ZAIB S,RAHMAN M M,et al.Didymin,a dietary Citrus flavonoid exhibits anti-diabetic complications and promotes glucose uptake through the activation of PI3K/Akt signaling pathway in insulin-resistant HepG2 cells[J].Chemico-Biological Interactions,2019,305:180-194.
[36] 季诗誉.柑橘果实黄酮类物质的降糖活性研究[D].杭州:浙江大学,2019.JI S Y.Hypoglycemic activity of flavonoids from Citrus fruits[D].Hangzhou:Zhejiang University,2019.
[37] HSU C C,LIN M H,CHENG J T,et al.Antihyperglycaemic action of diosmin,a Citrus flavonoid,is induced through endogenous beta-endorphin in type I-like diabetic rats[J].Clinical and Experimental Pharmacology and Physiology,2017,44(5):549-555.
[38] JAYARAMAN R,SUBRAMANI S,SHEIK ABDULLAH S H,et al.Antihyperglycemic effect of hesperetin,a Citrus flavonoid,extenuates hyperglycemia and exploring the potential role in antioxidant and antihyperlipidemic in streptozotocin-induced diabetic rats[J].Biomedicine & Pharmacotherapy,2018,97:98-106.
[39] SUNDARAM R,NANDHAKUMAR E,HASEENA BANU H.Hesperidin,a Citrus flavonoid ameliorates hyperglycemia by regulating key enzymes of carbohydrate metabolism in streptozotocin-induced diabetic rats[J].Toxicology Mechanisms and Methods,2019,29(9):644-653.
[40] UMRAN N S S,MOHAMED S,LAU S F,et al.Citrus hystrix leaf extract attenuated diabetic-cataract in STZ-rats[J].Journal of Food Biochemistry,2020,44(8):e13258.
[41] 肖博.橙皮苷对糖尿病大鼠视网膜神经节细胞的影响及其机制[D].唐山:华北理工大学,2020:3-25.XIAO B.Effects of hesperidin on retinal ganglion cells in diabetic rats and its mechanism[D].Tangshan:North China University of Science and Technology,2020:3-25.
[42] SINGH P,BANSAL S,KUHAD A,et al.Naringenin ameliorates diabetic neuropathic pain by modulation of oxidative-nitrosative stress,cytokines and MMP-9 levels[J].Food & Function,2020,11(5):4 548-4 560.
[43] MATO MOFO E P,ESSOP M F,OWIRA P M O.Citrus fruit-derived flavonoid naringenin and the expression of hepatic organic cation transporter 1 protein in diabetic rats treated with metformin[J].Basic & Clinical Pharmacology & Toxicology,2020,127(3):211-220.
[44] NAGAPPAN A,LEE H J,SARALAMMA V V,et al.Flavonoids isolated from Citrus platymamma induced G2/M cell cycle arrest and apoptosis in A549 human lung cancer cells[J].Oncology Letters,2016,12(2):1 394-1 402.
[45] HONG G E,LEE H J,KIM J A,et al.Korean Byungkyul-Citrus platymamma Hort.et Tanaka flavonoids induces cell cycle arrest and apoptosis,regulating MMP protein expression in Hep3B hepatocellular carcinoma cells[J].International Journal of Oncology,2017,50(2):575-586.
[46] DAI T Y,WANG B,LIN S Y,et al.Pure total flavonoids from Citrus paradisi Macfad induce leukemia cell apoptosis in vitro[J].Chinese Journal of Integrative Medicine,2017,23(5):370-375.
[47] 汪超.橙皮素通过内质网应激通路诱导人肺癌细胞PC9发生凋亡[D].合肥:安徽医科大学,2019:7-37.WANG C.Hesperidin induces apoptosis of human lung carcinoma cell PC9 through endoplasmic reticulum(ER)stress[D].Hefei:Anhui Medical University,2019:7-37.
[48] KO Y C,CHOI H S,LIU R,et al.Inhibitory effects of tangeretin,a Citrus Peel-derived flavonoid,on breast cancer stem cell formation through suppression of Stat3 signaling[J].Molecules,2020,25(11):e2599.
[49] KE J Y,BANH T,HSIAO Y H,et al.Citrus flavonoid naringenin reduces mammary tumor cell viability,adipose mass,and adipose inflammation in obese ovariectomized mice[J].Molecular Nutrition & Food Research,2017,61(9):1600934.
[50] SONG M,LAN Y,WU X,et al.The chemopreventive effect of 5-demethylnobiletin,a unique Citrus flavonoid,on colitis-driven colorectal carcinogenesis in mice is associated with its colonic metabolites[J].Food & Function,2020,11(6):4 940-4 952.
[51] CHEN S,JIANG J,CHAO G,et al.Pure total flavonoids from Citrus protect against nonsteroidal anti-inflammatory drug-induced small intestine injury by promoting autophagy in vivo and in vitro[J].Frontiers in Pharmacology,2021,12:622744.
[52] HE W,LIU M,LI Y,et al.Flavonoids from Citrus aurantium ameliorate TNBS-induced ulcerative colitis through protecting colonic mucus layer integrity[J].European Journal of Pharmacology,2019,857:172456.
[53] LIU P,BIAN Y,FAN Y,et al.Protective effect of naringin on in vitro gut-vascular barrier disruption of intestinal microvascular endothelial cells induced by TNF-alpha[J].Journal of Agricultural and Food Chemistry,2020,68(1):168-175.
[54] KARN A.基于体外发酵的柑橘黄酮与人体肠道菌群相互作用研究[D].北京:中国农业科学院,2020:23-35.KARN A.In vitro study of interactions between Citrus flavonoids and gut microbiota[D].Beijing:Chinese Academy of Agricultural Sciences,2020:23-35.
[55] SHEN C Y,LIN J J,JIANG J G,et al.Potential roles of dietary flavonoids from Citrus aurantium L.var.amara Engl.in atherosclerosis development[J].Food & Function,2020,11(1):561-571.
[56] TESTAI L,PIRAGINE E,PIANO I,et al.The Citrus flavonoid naringenin protects the myocardium from ageing-dependent dysfunction:Potential role of SIRT1[J].Oxidative Medicine and Cellular Longevity,2020,2 020:4650207.
[57] PLA-PAGA L,GUIRRO M,GUAL-GRAU A,et al.Proteomic analysis of heart and kidney tissues in healthy and metabolic syndrome rats after hesperidin supplementation[J].Molecular Nutrition & Food Research,2020,64(10):e1901063.
[58] LING Y,SHI Z,YANG X,et al.Hypolipidemic effect of pure total flavonoids from peel of Citrus(PTFC)on hamsters of hyperlipidemia and its potential mechanism[J].Experimental Gerontology,2020,130:110786.
[59] AGIR M S,ERASLAN G.The effect of diosmin against liver damage caused by cadmium in rats[J].Journal of Food Biochemistry,2019,43(9):e12966.
[60] LEE E Y,KIM S H,CHANG S N,et al.Efficacy of polymethoxylated flavonoids from Citrus depressa extract on alcohol-induced liver injury in mice[J].Biotechnology and Bioprocess Engineering,2019,24(6):907-914.
[61] JIANG J,YAN L,SHI Z,et al.Hepatoprotective and anti-inflammatory effects of total flavonoids of Qu Zhi Ke(peel of Citrus changshan-huyou)on non-alcoholic fatty liver disease in rats via modulation of NF-kappaB and MAPKs[J].Phytomedicine,2019,64:153082.
[62] SHI Z,LI T,LIU Y,et al.Hepatoprotective and anti-oxidative effects of total flavonoids from Qu Zhi Qiao(fruit of Citrus Paradisi cv.Changshanhuyou)on nonalcoholic steatohepatitis in vivo and in vitro through Nrf2-ARE signaling pathway[J].Frontiers in Pharmacology,2020,11:483.
[63] HE B,JIANG J,SHI Z,et al.Pure total flavonoids from Citrus attenuate non-alcoholic steatohepatitis via regulating the gut microbiota and bile acid metabolism in mice[J].Biomedicine & Pharmacotherapy,2021,135:111183.
[64] 张海萍,袁梅,蒋玲,等.柑橘黄酮对帕金森病模型细胞增殖和凋亡的影响研究[J].中国临床药理学杂志,2020,36(5):555-559.ZHANG H P,YUAN M,JIANG L,et al.Citrus flavone affects proliferation apoptosis of Parkinson disease model cell by regulating SNHG1 expression[J].The Chinese Journal of Clinical Pharmacology,2020,36(5):555-559.
[65] ZHOU T,LIU L,WANG Q,et al.Naringenin alleviates cognition deficits in high-fat diet-fed SAMP8 mice[J].Journal of Food Biochemistry,2020,44(9):e13375.
[66] SATO M,OKUNO A,SUZUKI K,et al.Dietary intake of the Citrus flavonoid hesperidin affects stress-resilience and brain kynurenine levels in a subchronic and mild social defeat stress model in mice[J].Bioscience,Biotechnology,and Biochemistry,2019,83(9):1 756-1 765.
[67] MILER M,ZIVANOVIC J,AJDZANOVIC V,et al.Citrus flavanones upregulate thyrotroph Sirt1 and differently affect thyroid Nrf2 expressions in old-aged Wistar rats[J].Journal of Agricultural and Food Chemistry,2020,68(31):8 242-8 254.