Anti-inflammation Activity Evaluation of Apigenin-O-Glycosides and Apigenin-C-Glycosides

LI Hui; PAN Siyi; XU Xiaoyun

doi:10.13386/j.issn1002-0306.2021100016

Volume 43 Issue 13

Jun. 2022

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Science and Technology of Food Industry > 2022 > 43(13): 345-352. > DOI: 10.13386/j.issn1002-0306.2021100016

LI Hui, PAN Siyi, XU Xiaoyun. Anti-inflammation Activity Evaluation of Apigenin-O-Glycosides and Apigenin-C-Glycosides[J]. Science and Technology of Food Industry, 2022, 43(13): 345−352. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021100016.

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Anti-inflammation Activity Evaluation of Apigenin-O-Glycosides and Apigenin-C-Glycosides

LI Hui^1,,
PAN Siyi²,
XU Xiaoyun^2, ,

1.
College of Life Sciences, Jianghan University, Wuhan 430056, China
2.
College of Food Science and Technology, Huazhong Agricultural University, Wuhan 430070, China

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Received Date: October 10, 2021
Available Online: April 25, 2022

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Abstract

Abstract

Objective: The anti-inflammatory activities of apigenin-7-O-β-D-glucopyranoside, apigenin 5-O-glucoside, vitexin and isovitexin were evaluated. Methods: Changes of protein in THP-1 cells pretreated with flavonoids were measured by Western blot test. The differences of cytokines were analyzed by enzyme-linked immunosorbent assay and fluorescence quantitative polymerase chain reaction. Results: It showed that all the flavonoids tested could repress the gene expression of IL-10 (P<0.01). Vitexin and isovitexin inhibited the production of cyclooxygenase-2 as well (P<0.01). What’s more, isovitexin significantly suppressed the increases of interleukin-1β (P<0.01) and interleukin-6 (P<0.01). Apigenin-7-O-β-D-glucopyranoside only significantly inhibited TNF-α (P<0.01). Apart from IL-10 mRNA, apigenin 5-O-glucoside displayed no anti-inflammatory effects according to the other results of cytokine analyses. Furthermore, the structure of apigenin-C-glycoside substituted at position 8, namely isovitexin showed the strongest inhibition on nuclear translocation of P65 (P<0.01). However, this suppression effect of isovitexin on P65 was not through inhibiting upstream regulation proteins such as IκBα and IKKβ. Conclusion: In a word, compared with apigenin-O-glycosides, apigenin-C-glycosides especially isovitexin had a better anti-inflammatory activity based on cell line THP-1. But the anti-inflamamtion of isovitexin was not IκBα -dependent NF- κB signal pathway.
- anti-inflammatory,
- flavonoid,
- flavone-O-glycosides,
- flavone-C-glycosides,
- isovitexin

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References (38)

References

[1]	韩公羽, 沈企华, 韩绍雯. 植物药黄酮成分与生理生化活性[M]. 北京: 中国书籍出版社, 2010: 38−45 HAN G Y, SHEN Q H, HAN S W. Flavonoids and physiological and biochemical activities of plant drugs[M]. Beijing: China Book Press, 2010: 38−45.
[2]	谢凡, 吴迎春, 李医明, 等. 葎草药材的质量标准研究[J]. 中国中药杂志,2014(20):3986−3990. [XE F, WU Y C, LI Y M, et al. Study on quality standard for Humulus scandens[J]. China Journal of Chinese Materia Medica,2014(20):3986−3990. XE F, WU Y C, LI Y M, et al. Study on quality standard for Humulus scandens[J]. China Journal of Chinese Materia Medica, 2014(20): 3986-3990.
[3]	刘细桥, 董俊兴. 中药地锦草芹菜素糖苷类化合物[J]. 药学学报,2009,44(5):496−499. [LIU X Q, DONG J X. Apigenin glycosides from Euphorbia humifusa Wild[J]. Acta Pharmaceutica Sinica,2009,44(5):496−499. doi: 10.3321/j.issn:0513-4870.2009.05.010 LIU X Q, DONG J X. Apigenin glycosides from Euphorbia humifusa Wild[J]. Acta Pharmaceutica Sinica, 2009, 44(05): 496-499. doi: 10.3321/j.issn:0513-4870.2009.05.010
[4]	李慧, 潘思轶, 徐晓云. 莲子心水提物中黄酮类化合物的结构及其对RAW264.7小鼠巨噬细胞NO生成的影响[J]. 中国食品学报,2018,18(2):44−54. [LI H, PAN S Y, XU X Y. Structures of flavones in lotus plumule water extract and the effect on RAW264.7 mouse ’ macrophage producing NO[J]. Journal of Chinese Institute of Food Science and Technology,2018,18(2):44−54. LI H, PAN S Y, XU X Y. Structures of flavones in lotus plumule water extract and the effect on RAW264.7 mouse’ macrophage producing NO[J]. Journal of Chinese Institute of Food Science and Technology, 2018, 018(2): 44-54.
[5]	NICHOLAS C, BATRA S, VARGO M A, et al. Apigenin blocks lipopolysaccharide-induced lethality in vivo and proinflammatory cytokines expression by inactivating NF-kappaB through the suppression of P65 phosphorylation[J]. Journal of Immunology,2007,179(10):7121−7127. doi: 10.4049/jimmunol.179.10.7121
[6]	CARDENAS H, ARANGO D, NICHOLAS C, et al. Dietary apigenin exerts immune-regulatory activity in vivo by reducing NF-κB activity, halting leukocyte infiltration and restoring normal metabolic function[J]. International Journal of Molecular Sciences,2016,17:323. doi: 10.3390/ijms17030323
[7]	朱理, 陈召桂, 何剑飞, 等. 箬叶中4种黄酮苷的同步HPLC检测[J]. 食品与生物技术学报,2016,35(6):657−659. [ZHU L, CHEN Z G, HE J F, et al. Simultaneous determination of 4 flavonoid glycosides in Indocalmus leaf by HPLC[J]. Journal of Food Science and Biotechnology,2016,35(6):657−659. doi: 10.3969/j.issn.1673-1689.2016.06.015 ZHU L, CHEN Z G, HE J F, et al. Simultaneous determination of 4 flavonoid glycosides in Indocalmus leaf by HPLC[J]. Journal of Food Science and Biotechnology, 2016, 35(6): 657-659. doi: 10.3969/j.issn.1673-1689.2016.06.015
[8]	邓思珊, 刘洪旭, 马丽红, 等. 三叶青叶黄酮类化学成分的UPLC-MS/MS定性分析及HPLC含量测定[J]. 中国医药导报,2018,15(33):86−90,94. [DENG S S, LIU H X, MA L H, et al. UPLC-MS/MS qualitative analysis and HPLC determination of flavonoids in leaves of Tetrastigma hemsleyanum[J]. China Medical Herald,2018,15(33):86−90,94. DENG S S, LIU H X, MA L H, et al. UPLC-MS/MS qualitative analysis and HPLC determination of flavonoids in leaves of Tetrastigma hemsleyanum[J]. China Medical Herald, 2018, 15(33): 86-90, 94.
[9]	董银卯, 唐冬雁, 何聪芬, 等. 绿豆芽中异黄酮类成分提取工艺的优化及含量测定[J]. 安徽农业科学,2011(10):5746−5747. [DONG Y M, TANG D Y, HE C F, et al. Optimization of extraction process of isoflavonoids from mung bean sprout and determination of its content[J]. Journal of Anhui Agricultural Sciences,2011(10):5746−5747. doi: 10.3969/j.issn.0517-6611.2011.10.029 DONG Y M, TANG D Y, HE C F, et al. Optimization of extraction process of isoflavonoids from mung bean sprout and determination of its content[J]. Journal of Anhui Agricultural Sciences, 2011(10): 5746-5747. doi: 10.3969/j.issn.0517-6611.2011.10.029
[10]	庞晨. 发芽绿豆皮抗炎活性分析及其作用方式[D]. 武汉: 华中农业大学, 2018: 44−50 PANG C. Study on the anti-inflammatory activity of germinated mung bean hull and its mode of action[D]. Wuhan: Huazhong Agricultural University, 2018: 44−50.
[11]	GUO H, LI M, XU L J. Apigetrin treatment attenuates LPS-induced acute otitis media though suppressing inflammation and oxidative stress[J]. Biomedicine & Pharmacotherapy,2019,109:1978−1987.
[12]	CHANPUT W, MES J J, WICHERS H J. THP-1 cell line: An in vitro cell model for immune modulation approach[J]. International Immunopharmacology,2014,23(1):37−45. doi: 10.1016/j.intimp.2014.08.002
[13]	SHIRATORI H, FEINWEBER C, LUCKHARDT S, et al. THP-1 and human peripheral blood mononuclear cell-derived macrophages differ in their capacity to polarize in vitro[J]. Molecular Immunology,2017,88:58−68. doi: 10.1016/j.molimm.2017.05.027
[14]	LUND M E, TO J, O'BRIEN B A, et al. The choice of phorbol 12-myristate 13-acetate differentiation protocol influences the response of THP-1 macrophages to a pro-inflammatory stimulus[J]. Journal of Immunological Methods,2016,430:64−70. doi: 10.1016/j.jim.2016.01.012
[15]	ZHENG L T, OCK J, KWON B M, et al. Suppressive effects of flavonoid fisetin on lipopolysaccharide-induced microglial activation and neurotoxicity[J]. International Immunopharmacology,2008,8(3):484−494. doi: 10.1016/j.intimp.2007.12.012
[16]	LI X C, SONG M F, FENG S, et al. Fragile X-related protein 1 (FXR1) regulates cyclooxygenase-2 (COX-2) expression at the maternal-fetal interface[J]. Reproduction, Fertility and Development,2018,30(11):1566−1574. doi: 10.1071/RD18037
[17]	CHANPUT W, KRUEYOS N, RITTHIRUANGDEJ P. Anti-oxidative assays as markers for anti-inflammatory activity of flavonoids[J]. International Immunopharmacology,2016,40:170−175. doi: 10.1016/j.intimp.2016.08.038
[18]	KAN X, LIU B, GUO W, et al. Myricetin relieves LPS-induced mastitis by inhibiting inflammatory response and repairing the blood-milk barrier[J]. Journal of Cellular Physiology,2019,234(9):16252−16262. doi: 10.1002/jcp.28288
[19]	LI H, PAN S Y, XU X Y. Structure characteristics of flavonoids for cyclooxygenase-2 mRNA inhibition in lipopolysaccharide-induced inflammatory macrophages[J]. European Journal of Pharmacology,2019,856:172416. doi: 10.1016/j.ejphar.2019.172416
[20]	DUBOIS R N, ABRAMSON S B, CROFFORD L, et al. Cyclooxygenase in biology and disease[J]. Faseb Journal Official Publication of the Federation of American Societies for Experimental Biology,1998,12(12):1063−1073. doi: 10.1096/fasebj.12.12.1063
[21]	WANG L, TU Y C, LIAN T W, et al. Distinctive antioxidant and antiinflammatory effects of flavonols[J]. Journal of Agricultural & Food Chemistry,2006,54(26):9798−9804.
[22]	HA S K, LEE P, PARK J A, et al. Apigenin inhibits the production of NO and PGE2 in microglia and inhibits neuronal cell death in a middle cerebral artery occlusion-induced focal ischemia mice model[J]. Neurochemistry International,2008,52(4):878−886.
[23]	HUANG Z, WANG C, WEI L, et al. Resveratrol inhibits EMMPRIN expression via P38 and ERK1/2 pathways in PMA-induced THP-1 cells[J]. Biochemical and Biophysical Research Communications,2008,374(3):517−521. doi: 10.1016/j.bbrc.2008.07.058
[24]	OLSZEWSKI M B, GROOT A J, DASTYCH J, et al. TNF trafficking to human mast cell granules: Mature chain-dependent endocytosis[J]. Journal of Immunology,2007,178(9):5701−5709. doi: 10.4049/jimmunol.178.9.5701
[25]	PETKOVIC A B, MATIC S M, STAMATOVIC N V, et al. Proinflammatory cytokines (IL-1 beta and TNF-alpha) and chemokines (IL-8 and MIP-1 alpha) as markers of pen-implant tissue condition[J]. International Journal of Oral and Maxillofacial Surgery,2010,39(5):478−485. doi: 10.1016/j.ijom.2010.01.014
[26]	BARNES P J, KARIN M. Nuclear factor-kappaB: A pivotal transcription factor in chronic inflammatory diseases[J]. N Engl J Med,1997,336(15):1066−1071. doi: 10.1056/NEJM199704103361506
[27]	HAYDEN M S, GHOSH S. Shared principles in NF-kappaB signaling[J]. Cell,2008,132(3):344−362. doi: 10.1016/j.cell.2008.01.020
[28]	KAEKO M, SUMIE S, SAYURI M, et al. Unique uptake and transport of isoflavone aglycones by human intestinal Caco-2 cells: Comparison of isoflavonoids and flavonoids[J]. Journal of Nutrition,2002(7):1956−1961.
[29]	陈丙銮, 李松林, 李萍, 等. 黄酮类化合物在Caco-2细胞模型中的吸收规律[J]. 中国天然药物,2006,4(4):299−302. [CHEN B L, LI S L, LI P, et al. The uptake characteristics of flavonoids in the Caco-2 model system[J]. Chinese Journal of Natural Medicines,2006,4(4):299−302. CHEN B L, LI S L, LI P, et al. The uptake characteristics of flavonoids in the Caco-2 model system[J]. Chinese Journal of Natural Medicines, 2006, 4(4): 299-302.
[30]	周乐, 赵晓莉, 狄留庆, 等. 黄酮类化合物口服吸收与代谢特征及其规律分析[J]. 中草药,2013,44(16):2313−2320. [ZHOU L, ZHAO X L, DI L Q, et al. Oral absorption of flavonoids and analysis of their metabolism characteristics and law[J]. Chinese Traditional and Herbal Drugs,2013,44(16):2313−2320. ZHOU L, ZHAO X L, DI L Q, et al. Oral absorption of flavonoids and analysis of their metabolism characteristics and law[J]. Chinese Traditional and Herbal Drugs, 2013, 44(16): 2313-2320.
[31]	FANG Y J, CAO W W, LIANG F Q, et al. Structure affinity relationship and docking studies of flavonoids as substrates of multidrug-resistant associated protein 2 (MRP2) in MDCK/MRP2 cells[J]. Food Chemistry,2019,291:101−109. doi: 10.1016/j.foodchem.2019.03.111
[32]	FANG Y J, XIA M M, LIANG F Q, et al. Establishment and use of human mouth epidermal carcinoma (KB) cells overexpressing P-glycoprotein to characterize structure requirements for flavonoids transported by the efflux transporter[J]. Journal of Agricultural and Food Chemistry,2019,67(8):2350−2360. doi: 10.1021/acs.jafc.9b00039
[33]	CHEN Y, ZHAO Y H, JIA X B, et al. Intestinal absorption mechanisms of prenylated flavonoids present in the heat-processed Epimedium koreanum Nakai (Yin Yanghuo)[J]. Pharmaceutical Research,2008,25(9):2190−2199. doi: 10.1007/s11095-008-9602-7
[34]	李军茂, 何明珍, 冯育林, 等. 木犀草素及木犀草苷在大鼠体内的代谢研究[J]. 中药新药与临床药理,2017,28(1):61−68. [LI J M, HE M Z, FENG Y L, et al. In vivo studies on metabolism of luteolin and luteoloside in rats[J]. Traditional Chinese Drug Research and Clinical Pharmacology,2017,28(1):61−68. LI J M, HE M Z, FENG Y L, et al. In vivo studies on metabolism of luteolin and luteoloside in rats[J]. Traditional Chinese Drug Research and Clinical Pharmacology, 2017, 28(1): 61-68.
[35]	白岩. 绿豆化学成分及其质量控制与药动学研究[D]. 沈阳: 沈阳药科大学, 2017: 104−116 BAI Y. Constituents, quality control, and pharmacokinetics study on the mung bean (Vigna radiate L.)[D]. Shenyang: Shenyang Pharmaceutical University, 2017: 104−116.
[36]	童成亮, 刘晓东. 牡荆素在大鼠体内的药代动力学[J]. 中国药科大学学报,2007,38(1):65−68. [TONG C L, LIU X D. Pharmacokinetics of vitexin in rats[J]. Journal of China Pharmaceutical University,2007,38(1):65−68. doi: 10.3321/j.issn:1000-5048.2007.01.016 TONG C L, LIU X D. Pharmacokinetics of vitexin in rats[J]. Journal of China Pharmaceutical University, 2007, 38(1): 65-68. doi: 10.3321/j.issn:1000-5048.2007.01.016
[37]	BAI Y, ZHANG Q, WANG B, et al. Plasma pharmacokinetics, bioavailability and tissue distribution of four C-glycosyl flavones from mung bean (Vigna radiata L.) seeds extracts in rat by UHPLC-MS/MS[J]. Journal of Agricultural & Food Chemistry,2017,65(27):5570−5580.
[38]	GONZÁLEZ R, BALLESTER I, LÓPEZ-POSADAS R, SUAREZ M D, et al. Effects of flavonoids and other polyphenols on inflammation[J]. Critical Reviews in Food Science and Nutrtion,2011,51:331−362. doi: 10.1080/10408390903584094

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