Skip to main content
SpringerLink
Log in

Recent Advances in Synthetic Aspects of Naringenin Flavonoid and its Bioprotective Effect (A Review)

  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

Flavonoids which are secondary metabolites of plants are found naturally in fruits, vegetables, nuts, herbs, and spices, so they are important constituent of human diet also. They are also responsible for various pigments in plants and offer various health benefits to humans due to their diverse biological activities. Naringenin is a flavanone class of flavonoid and it is profusely found in citrus fruits, grapefruit, tomatoes and finds its extensive application in cosmetic industries, perfumeries as well as pharmaceutical formulations. This phytochemical has bioactive effects on human health as antioxidant, antiviral, anti-cancerous, antibacterial, anti-inflammatory, anti-obesity and hepatoprotective effects. Its anti-inflammatory and immune-stimulating actions plays a role in either preventing or control COVID infections to some extent according to recent reports. This review brings together all its synthetic routes reported till date and it also focused on the recent developments of its bioprotective effects and pharmacokinetic activities.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.

Similar content being viewed by others

DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

REFERENCES

  1. Patel, K., Singh, G.K., and Patel, D.K., Chin. J. Integr. Med., 2018, vol. 24, pp. 551–560. https://doi.org/10.1007/s11655-014-1960-x

    Article  CAS  PubMed  Google Scholar 

  2. Sumathi, R., Tamizharasi, S., and Sivakumar, T., Bio-Dynamic, 2015, vol. 4, pp. 234–236.

    Google Scholar 

  3. Jadeja, R.N. and Devkar, R.V., Elsevier Inc., 2013, vol. 1. ISBN 9780123984562.

  4. Soltana, H., De Rosso, M., Lazreg, H., Vedova, A.D., Hammami, M., and Flamini, R. J. Mass Spectr., 2018, vol. 53, pp. 817–823. https://doi.org/10.1002/jms.4209

    Article  CAS  Google Scholar 

  5. Erlund, I., Nutr. Res., 2004, vol. 24, pp. 851–874. https://doi.org/10.1016/j.nutres.2004.07.005

    Article  CAS  Google Scholar 

  6. Madrigal-Santillán, E., Madrigal-Bujaidar, E., Álvarez-González, I., Sumaya-Martínez, M.T., Gutiérrez-Salinas, J., Bautista, M., Morales-González, Á., García-Luna, Y., González-Rubio, M., Aguilar-Faisal, J.L., and Morales-González, J.A., World J. Gastroenterol., 2014, vol. 20, pp. 14787–14804. https://doi.org/10.3748/wjg.v20.i40.14787

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Eichenberger, M., Lehka, B.J., Folly, C., Fischer, D., Martens, S., Simón, E., and Naesby, M. Metab. Eng., 2017, vol. 39, pp. 80–89. https://doi.org/10.1016/j.ymben.2016.10.019

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Álvarez-Álvarez, R., Botas, A., Albillos, S.M., Rumbero, A., Martín, J.F., and Liras, P., Microb. Cell Fact., 2015, vol. 14, pp. 1–12. https://doi.org/10.1186/s12934-015-0373-7

    Article  CAS  Google Scholar 

  9. Sharma, A., Bhardwaj, P., and Arya, S.K., Carbohydr. Polym. Technol. Appl., 2021, vol. 2. https://doi.org/10.1016/j.carpta.2021.100068

  10. Pasam, V.R., Kiran, S.P., Pasam, V.R., Kiran, S., and Rohini, P., J. Pharmacogn. Phytochem., 2017, vol. 6, pp. 2778–2783.

    Google Scholar 

  11. Karim, N., Jia, Z., Zheng, X., Cui, S., and Chen, W., Trends Food Sci. Technol., 2018, vol. 79, pp. 35–54. https://doi.org/10.1016/j.tifs.2018.06.012

    Article  CAS  Google Scholar 

  12. Du, Y., Ma, J., Fan, Y., Wang, X., Zheng, S., Feng, J., Li, J., Fan, Z., Li, G., and Ye, Q., Oxid. Med. Cell. Longev., 2021, vol. 2021, 1210675. https://doi.org/10.1155/2021/1210675

  13. Salehi, B., Fokou, P.V.T., Sharifi-Rad, M., Zucca, P., Pezzani, R., Martins, N., and Sharifi-Rad, J., Pharmaceuticals, 2019, vol. 12, p. 11. https://doi.org/10.3390/ph12010011

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Naeini, F., Namkhah, Z., Ostadrahimi, A., Tutunchi, H., and Hosseinzadeh-Attar, M.J., Adv. Nutr., 2021, vol. 12, pp. 413–428.

    Article  PubMed  Google Scholar 

  15. Wang, Q., Yang, J., Zhang, X.M., Zhou, L., Liao, X.L., and Yang, B. J., Chem. Res., 2015, vol. 39, pp. 455–457. https://doi.org/10.3184/174751915X14379994045537

    Article  CAS  Google Scholar 

  16. Wu, J., Zhou, T., Du, G., Zhou, J., and Chen, J., PLoS One, 2014, vol. 9, e101492. https://doi.org/10.1371/journal.pone.0101492

  17. Carceller, J.M., Martínez Galán, J.P., Monti, R., Bassan, J.C., Filice, M., Iborra, S., Yu, J., and Corma, A., Green Chem., 2019, vol. 21, pp. 839–849. https://doi.org/10.1039/c8gc03661f

    Article  CAS  Google Scholar 

  18. Cui, W., Zhang, J., Wang, Q., Gao, K., Zhang, W., and Yang, J. J., Chem. Res., 2014, vol. 38, pp. 686–689. https://doi.org/10.3184/174751914X14145820775908

    Article  CAS  Google Scholar 

  19. Koopman, F., Beekwilder, J., Crimi, B., Houwelingen, A., Hall, R.D., Bosch, D., Maris, A.J.A. Van., Pronk, J.T., and Daran, J., Microb. Cell Fact., 2012, vol. 11, pp. 1–15.

    Article  Google Scholar 

  20. Zang, Y., Zha, J., Wu, X., Zheng, Z., Ouyang, J., and Koffas, M.A.G. J., Agric. Food Chem., 2019, vol. 67, pp. 13430–13436. https://doi.org/10.1021/acs.jafc.9b00413

    Article  CAS  PubMed  Google Scholar 

  21. Deepa, C.N., Geetha, A, and Antony, F.C., Asian J. Pharm. Clin. Res., 2014, vol. 7, pp. 222–226. https://journals.innovareacademics.in/index.php/ajpcr/article/view/2556

    CAS  Google Scholar 

  22. Manchope, M.F., Calixto-Campos, C., Coelho-Silva, L., Zarpelon, A.C., Pinho-Ribeiro, F.A., Georgetti, S.R., Baracat, M.M., Casagrande, R., and Verri, W.A., PLoS One, 2016, vol. 11, e0153015. https://doi.org/10.1371/journal.pone.0153015

  23. Pinho-Ribeiro, F.A., Zarpelon, A.C., Fattori, V., Manchope, M.F., Mizokami, S.S., Casagrande, R., and Verri, W.A., Neuropharmacology, 2016, vol. 105, pp. 508–519. https://doi.org/10.1016/j.neuropharm.2016.02.019

    Article  CAS  PubMed  Google Scholar 

  24. Jin, L., Zeng, W., Zhang, F., Zhang, C., and Liang, W.J., Immunol., 2017, vol. 199, pp. 3466–3477. https://doi.org/10.4049/jimmunol.1602016

    Article  CAS  Google Scholar 

  25. Xue, N., Wu, X., Wu, L., Li, L., and Wang, F., Life Sci., 2019, vol. 217, pp. 148–154. https://doi.org/10.1016/j.lfs.2018.11.013

    Article  CAS  PubMed  Google Scholar 

  26. Chung, T.W., Li, S., Lin, C.C., and Tsai, S.W., Tzu Chi Med. J., 2019, vol. 31, pp. 81–85. https://doi.org/10.4103/tcmj.tcmj_103_18

    Article  PubMed Central  Google Scholar 

  27. de Oliveira, M.R., Andrade, C.M.B., and Fürstenau, C.R., Neurochem. Res., 2018, vol. 43, pp. 894–903. https://doi.org/10.1007/s11064-018-2495-x

    Article  CAS  PubMed  Google Scholar 

  28. Escribano-Ferrer, E., Queralt Regué, J., Garcia-Sala, X., Boix Montanés, A., and Lamuela-Raventos, R.M., J. Nat. Prod., 2019, vol. 82, pp. 177–182. https://doi.org/10.1021/acs.jnatprod.8b00366

    Article  CAS  PubMed  Google Scholar 

  29. Rajamani, S., Sengodan, T., Thangavelu, S., Shanmukhan, N.K., and Radhakrishnan, A., Indones. J. Pharm., 2019, vol. 30, pp. 225–232. https://doi.org/10.14499/indonesianjpharm30iss3pp217

    Article  CAS  Google Scholar 

  30. Mohanty, S., Sahoo, A.K., Konkimalla, V.B., Pal, A., and Si, S.C., ACS Omega, 2020, vol. 5, pp. 28319–28332. https://doi.org/10.1021/acsomega.0c04300

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Alberca, R.W., Teixeira, F.M.E., Beserra, D.R., de Oliveira, E.A., Andrade, M.M., de S., Pietrobon, A.J., and Sato, M.N., Front. Immunol., 2020, vol. 11, 570919. https://doi.org/10.3389/fimmu.2020.570919

  32. Muschietti, L.V., Austin J Pharmacol Ther., 2021, vol. 9, pp. 1–4.

    Google Scholar 

  33. Richard, A.J., Amini-Vaughan, Z., Ribnicky, D.M., and Stephens, J.M., Evidence-based Compl. Altern. Med., 2013, vol. 2013, 549750. https://doi.org/10.1155/2013/549750

  34. Yoshida, H., Watanabe, W., Oomagari, H., Tsuruta, E., Shida, M., and Kurokawa, M., J. Nutr. Biochem., 2013, vol. 24, pp. 1276–1284. https://doi.org/10.1016/j.jnutbio.2012.10.003

    Article  CAS  PubMed  Google Scholar 

  35. Yoshida, H., Watanabe, H., Ishida, A., Watanabe, W., Narumi, K., Atsumi, T., Sugita, C., and Kurokawa, M., Biochem. Biophys. Res. Commun., 2014, vol. 454, pp. 95–101. https://doi.org/10.1016/j.bbrc.2014.10.038

    Article  CAS  PubMed  Google Scholar 

  36. Assini, J.M., Mulvihill, E.E., Burke, A.C., Sutherland, B.G., Telford, D.E., Chhoker, S.S., Sawyez, C.G., Drangova, M., Adams, A.C., Kharitonenkov, A., Pin, C.L., and Huff, M.W., Endocrinology, 2015, vol. 156, pp. 2087–2102. https://doi.org/10.1210/en.2014-2003

    Article  CAS  PubMed  Google Scholar 

  37. Ansari, M.N., Ganaie, M.A., Khan, T.H., Samad, A., Madkhali, H.A., and Ahamad, S.R., Trop. J. Pharm. Res., 2018, vol. 17, pp. 239–244. https://doi.org/10.4314/tjpr.v17i2.7

    Article  CAS  Google Scholar 

  38. Ke, J.Y., Kliewer, K.L., Hamad, E.M., Cole, R.M., Powell, K.A., Andridge, R.R., Straka, S.R., Yee, L.D., and Belury, M.A., Nutr. Metab., 2015, vol. 12, p. 1. https://doi.org/10.1186/1743-7075-12-1

    Article  CAS  Google Scholar 

  39. Ke, J.Y., Cole, R.M., Hamad, E.M., Hsiao, Y.H., Cotten, B.M. Powell, K.A., and Belury, M.A., Mol. Nutr. Food Res., 2016, vol. 60, pp. 313–324. https://doi.org/10.1002/mnfr.201500379

    Article  CAS  PubMed  Google Scholar 

  40. Ke, J.Y., Banh, T., Hsiao, Y.H., Cole, R.M., Straka, S.R., Yee, L.D., and Belury, M.A., Mol. Nutr. Food Res., 2017, vol. 61, 1600934. https://doi.org/10.1002/mnfr.201600934

  41. Burke, A.C., Sutherland, B.G., Telford, D.E., Morrow, M.R., Sawyez, C.G., Edwards, J.Y., Drangova, M., and Huff, M.W., J. Lipid Res., 2018, vol. 59, pp. 1714–1728. https://doi.org/10.1194/jlr.M087387

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Burke, A.C., Telford, D.E., Edwards, J.Y., Sutherland, B.G., Sawyez, C.G., and Huff, M.W., Mol. Nutr. Food Res., 2019, vol. 63, 1800833. https://doi.org/10.1002/mnfr.201800833

  43. Rebello, C.J., Greenway, F.L., Lau, F.H., Lin, Y., Stephens, J.M., Johnson, W.D., and Coulter, A.A., Obesity, 2019, vol. 27, pp. 103–111. https://doi.org/10.1002/oby.22352

    Article  CAS  PubMed  Google Scholar 

  44. Tsuhako, R., Yoshida, H., Sugita, C., and Kurokawa, M., J. Nat. Med., 2020, vol. 74, pp. 229–237. https://doi.org/10.1007/s11418-019-01332-5

    Article  CAS  PubMed  Google Scholar 

  45. Naeini, F., Namkhah, Z., Tutunchi, H., Rezayat, S.M., Mansouri, S., Jazayeri-Tehrani, S.A., Yaseri, M., and Hosseinzadeh-Attar, M.J., Trials, 2021, vol. 22, 801. https://doi.org/10.1186/s13063-021-05784-7

  46. Dayarathne, A., Sewwandi, S., Natraj, P., and Rajan, P., Anti-diabetic and Anti-obesity Potentials of Naringin and Naringenin, Conference: 2020 Kalas international Symposium. https://doi.org/10.13140/RG.2.2.25037.67042

  47. Murugesan, N., Woodard, K., Ramaraju, R., Greenway, F.L., Coulter, A.A., and Rebello, C.J., J. Med. Food, 2020, vol. 23, pp. 343–348. https://doi.org/10.1089/jmf.2019.0216

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  48. Nishimura, F.D.C.Y., De Almeida, A.C., Ratti, B.A., Ueda-Nakamura, T., Nakamura, C.V., Ximenes, V.F., and De Oliveira Silva, S., Evid-Based Compl. Altern. Med., 2013, vol. 2013, 795916. https://doi.org/10.1155/2013/795916

  49. Hermenean, A., Ardelean, A., Stan, M., Hadaruga, N., Mihali, C.V., Costache, M., and Dinischiotu, A., J. Med. Food, 2014, vol. 17, pp. 670–677. https://doi.org/10.1089/jmf.2013.0007

    Article  CAS  PubMed  Google Scholar 

  50. Kerdudo, A., Dingas, A., Fernandez, X., and Faure, C., Food Chem., 2014, vol. 159, pp. 12–19. https://doi.org/10.1016/j.foodchem.2014.03.005

    Article  CAS  PubMed  Google Scholar 

  51. Yan, M.X., Gong, J.D., Shen, P., and Yang, C.Y., Proceed. Appl. Mechanic. Mat., 2014, vol. 513–517, pp. 359–362.

    Google Scholar 

  52. Vallejo, W.A., Diaz Uribe, C.D., Oliveros, G., and Muñoz, A., Prospectiva, 2016, vol. 14, 31. https://doi.org/10.15665/rp.v14i2.677

  53. Hernández-Aquino, E. and Muriel, P., World J. Gastroenterol., 2018, vol. 24, pp. 1679–1707.

    Article  PubMed  PubMed Central  Google Scholar 

  54. Rashmi, R., Bojan Magesh, S., Mohanram Ramkumar, K., Suryanarayanan, S., and Venkata SubbaRao, M., Rep. Biochem. Mol. Biol., 2018, vol. 7, pp. 76­–84.

    CAS  PubMed  PubMed Central  Google Scholar 

  55. Bilkan, M.T. and Bilkan, Ç., J. Inst. Sci. Technol., 2019, vol. 9, pp. 790–799. https://doi.org/10.21597/jist.445937

    Article  Google Scholar 

  56. Zheng, Y.Z., Deng, G., Guo, R., Chen, D.F., and Fu, Z.M., Int. J. Mol. Sci., 2019, vol. 20, 1450. https://doi.org/10.3390/ijms20061450

  57. Yildiztugay, E., Ozfidan-Konakci, C., Kucukoduk, M., and Turkan, I., Front. Plant Sci., 2020, vol. 11, 682. https://doi.org/10.3389/fpls.2020.00682

  58. Baranowska, M., Koziara, Z., Suliborska, K., Chrzanowski, W., Wormstone, M., Namieśnik, J., and Bartoszek, A., Sci. Rep., 2021, vol. 11, 12282. https://doi.org/10.1038/s41598-021-89314-0

  59. Ahamad, M.S., Siddiqui, S., Jafri, A., Ahmad, S., Afzal, M., and Arshad, M., PLoS One, 2014, vol. 9, e110003. https://doi.org/10.1371/journal.pone.0110003

  60. Baruah, T., Hauneihkim, K., and Kma, L., Pharmacogn. Mag., 2020, vol. 16, pp. 229–235. https://doi.org/10.4103/pm.pm_535_19

    Article  CAS  Google Scholar 

  61. Junedi, S., Hermawan, A., Setiawati, A., and Fitriyasari, A., Indonesian J. Cancer Chemoprevent., 2021, vol. 12, pp. 83–89. https://doi.org/10.14499/indonesianjcanchemoprev12iss2pp83-89

    Article  Google Scholar 

  62. Kocyigit, A., Koyuncu, I., Dikilitas, M., Bahadori, F., and Turkkan, B., Asian Pac. J. Trop. Biomed., 2016, vol. 6, pp. 872–880. https://doi.org/10.1016/j.apjtb.2016.08.004

    Article  CAS  Google Scholar 

  63. Wang, R., Wang, J., Dong, T., Shen, J., Gao, X., and Zhou, J., Oncol. Lett., 2019, vol. 17, pp. 1217–1222. https://doi.org/10.3892/ol.2018.9704

    Article  CAS  PubMed  Google Scholar 

  64. Song, H.M., Park, G.H., Eo, H.J., Lee, J.W., Kim, M.K., Lee, J.R., Lee, M.H., Koo, J.S., and Jeong, J.B., Biomol. Ther., 2015, vol. 23, pp. 339–344. https://doi.org/10.4062/biomolther.2015.024

    Article  CAS  Google Scholar 

  65. Abaza, M.S.I., Orabi, K.Y., Al-Quattan, E., and Al-Attiyah, R.J., Cancer Cell Int., 2015, vol. 15, pp. 1–19. https://doi.org/10.1186/s12935-015-0194-0

    Article  CAS  Google Scholar 

  66. El-Kersh, D.M., Ezzat, S.M., Salama, M.M., Mahrous, E.A., Attia, Y.M., Ahmed, M.S., and Elmazar, M.M., Sci. Rep., 2021, vol. 11, pp. 1–14. https://doi.org/10.1038/s41598-021-86599-z

    Article  CAS  Google Scholar 

  67. Noori, S., Tavirani, M.R., Deravi, N., Rabbani, M.I.M., and Zarghi, A., Iran. J. Pharm. Res., 2020, vol. 19, pp. 122–133. https://doi.org/10.22037/ijpr.2020.113103.14112

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  68. Krishnakumar, N., Sulfikkarali, N., RajendraPrasad, N., and Karthikeyan, S., Biomed. Prev. Nutr., 2011, vol. 1, pp. 223–231. https://doi.org/10.1016/j.bionut.2011.09.003

    Article  Google Scholar 

  69. Askar, M.A., El Shawi, O.E., Abou Zaid, O.A.R., Mansour, N.A., and Hanafy, A.M., Tumour Biol., 2021, vol. 43, pp. 225–247. https://doi.org/10.3233/TUB-211506

    Article  PubMed  Google Scholar 

  70. Rajamani, S., Radhakrishnan, A., Sengodan, T., and Thangavelu, S., Drug Dev. Ind. Pharm., 2018, vol. 44, pp. 1752–1761. https://doi.org/10.1080/03639045.2018.1496445

    Article  CAS  PubMed  Google Scholar 

  71. Shadab, M., Alhakamy, N.A., Akhter, S., Awan, Z.A.Y., Aldawsari, H.M., Alharbi, W.S., Haque, A., Choudhury, H., and Sivakumar, P.M., J. Chem., 2020, vol. 2020, Article ID: 3489393. https://doi.org/10.1155/2020/3489393

  72. Zhang, S., Jiang, Z.F., Pan, Q., Song, C.Y., and Zhang, W.H., Bangladesh J. Pharmacol., 2016, vol. 11, pp. 684–690. https://doi.org/10.3329/bjp.v11i3.27518

    Article  Google Scholar 

  73. Stabrauskiene, J., Kopustinskiene, D.M., Lazauskas, R., and Bernatoniene, J., Biomedicines, 2022, vol. 10, pp. 1–16. https://doi.org/10.3390/biomedicines10071686

    Article  CAS  Google Scholar 

  74. Goldwasser, J., Cohen, P.Y., Yang, E., Balaguer, P., Yarmush, M.L., and Nahmias, Y., PLoS One, 2010, vol. 5, e12399. https://doi.org/10.1371/journal.pone.0012399

  75. Demonty, I., Lin, Y., Zebregs, Y.E.M.P., Vermeer, M.A., Van Der Knaap, H.C.M., Jäkel, M., and Trautwein, E.A., J. Nutr., 2010, vol. 140, pp. 1615–1620. https://doi.org/10.3945/jn.110.124735

    Article  CAS  PubMed  Google Scholar 

  76. Jayaraman, J., Jesudoss, V.A.S., Menon, V.P., and Namasivayam, N., Toxicol. Mech. Methods, 2012, vol. 22, pp. 568–576. https://doi.org/10.3109/15376516.2012.707255

    Article  CAS  PubMed  Google Scholar 

  77. Ahmed, O.M., Moawad Mahmoud, A., Abdel Moneim, A., Mohamed Ahmed, O., Abdel-Moneim, A., and Ashour, M.B., Life Sci. J., 2011, vol. 8, pp. 91–101.

    Google Scholar 

  78. Jayachitra, J. and Nalini, N., J. Food Biochem., 2012, vol. 36, pp. 502–511. https://doi.org/10.1111/j.1745-4514.2011.00561.x

    Article  CAS  Google Scholar 

  79. Jayaraman, J. and Namasivayam, N., Fundam. Clin. Pharmacol., 2011, vol. 25, pp. 682–689. https://doi.org/10.1111/j.1472-8206.2010.00899.x

    Article  CAS  PubMed  Google Scholar 

  80. Trends in Food Science and Technology: Editorial. Trends Food Sci. Technol., 2001, vol. 12, p. 260. https://doi.org/10.1016/S0924-2244(02)00026-2

  81. Mershiba, S.D., Dassprakash, M.V., and Saraswathy, S.D., Mol. Biol. Rep., 2013, vol. 40, pp. 3681–3691. https://doi.org/10.1007/s11033-012-2444-8

    Article  CAS  PubMed  Google Scholar 

  82. Motawi, T.K., Teleb, Z.A., El-Boghdady, N.A., and Ibrahim, S.A., J. Physiol. Biochem., 2014, vol. 70, pp. 225–237. https://doi.org/10.1007/s13105-013-0296-x

    Article  CAS  PubMed  Google Scholar 

  83. Ozkaya, A., Sahin, Z., Dag, U., and Ozkaraca, M., J. Biochem. Mol. Toxicol., 2016, vol. 30, pp. 243–248. https://doi.org/10.1002/jbt.21785

    Article  CAS  PubMed  Google Scholar 

  84. Wang, C., Fan, R.Q., Zhang, Y.X., Nie, H., and Li, K., World J. Gastroenterol., 2016, vol. 22, pp. 9775–9783. https://doi.org/10.3748/wjg.v22.i44.9775

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  85. Sirovina, D., Orsolic, N., Gregorovic, G., and Koncic, M.Z., Arh. Hig. Rada Toksikol., 2016, vol. 67, pp. 19–24. https://doi.org/10.1515/aiht-2016-67-2708

    Article  CAS  PubMed  Google Scholar 

  86. Chen, C., Jie, X., Ou, Y., Cao, Y., Xu, L., Wang, Y., and Qi, R., Nanomedicine, 2017, vol. 12, pp. 1791–1800. https://doi.org/10.2217/nnm-2017-0119

    Article  CAS  PubMed  Google Scholar 

  87. Zhao, L., Zhang, N., Yang, D., Yang, M., Guo, X., He, J., Wu, W., Ji, B., Cheng, Q., Zhou, F., Nutrients, 2018, vol. 10, 1754. https://doi.org/10.3390/nu10111754

  88. Ahmed, O.M., Fahim, H.I., Ahmed, H.Y., Al-Muzafar, H.M., Ahmed, R.R., Amin, K.A., El-Nahass, E.S., and Abdelazeem, W.H., Oxid. Med. Cell. Longev., 2019, vol. 2019, Article ID: 2745352. https://doi.org/10.1155/2019/2745352

  89. Gama, G., Alberca, F., Fernandes, I.G., and Sato, M.N., Kid. Front. Org., 2021, vol. 8, pp. 1–8. https://doi.org/10.3389/frym.2020.00074

    Article  Google Scholar 

  90. Li, F., Annu. Rev. Virol., 2016, vol. 3, pp. 237–261. https://doi.org/10.1146/annurev-virology-110615042301

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  91. Abbas, G., Al-Taey, D.K.A., Al-Azawi, S.S.M., Mehdizadeh, M., Qureshi, R.A.M., Jasman, A.K., Slomy, A.K., Khan, M.A., Jabbar, M.A., and Iqbal, A., IOP Conf. Ser. Earth Environ. Sci., 2021, vol. 910, Article ID: 012045. https://doi.org/10.1088/1755-1315/910/1/012045

  92. Kishi, K., Bull. hort. Res. Stat, Hiratsuka, 1967, vol. 6, pp. 105–114.

    Google Scholar 

  93. Hyun, J.W., Hwang, R.Y., Choi, C.W., Jung, K.E., and Han, S.G., Plant Pathol. J., 2020, vol. 36, pp. 106–110. https://doi.org/10.5423/PPJ.NT.07.2019.0192

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  94. Garufi, G., Carbognin, L., and Orlandi, A., Brain. Behav. Immun., 2020, vol. 2020, pp. 19–21.

    Google Scholar 

  95. Khan, A., Ikram, M., Hahm, J.R., and Kim, M.O., Antioxidants, 2020, vol. 9, pp. 1–15. https://doi.org/10.3390/antiox9070609

    Article  CAS  Google Scholar 

  96. Agrawal, P.K., Agrawal, C., and Blunden, G., Nat. Prod. Commun., 2021, vol. 16, https://doi.org/10.1177/1934578X211066723

  97. Tanonaka, K. and Marunouchi, T., Folia Pharmacol. Jpn., 2016, vol. 147, pp. 120–121. https://doi.org/10.1254/fpj.147.120

    Article  CAS  Google Scholar 

  98. Kuba, K., Imai, Y., Rao, S., Gao, H., Guo, F., Guan, B., Huan, Y., Yang, P., Zhang, Y., and Deng, W., Nat. Med., 2005, vol. 11, pp. 875–879. https://doi.org/10.1038/nm1267

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  99. Bouhaddou, M., Memon, D., Meyer, B., White, K.M., Rezelj, V. V., Correa Marrero, M., Polacco, B.J., Melnyk, J.E., Ulferts, S., and Kaake, R.M., Cell, 2020, vol. 182, Article ID: 685-712.e19. https://doi.org/10.1016/j.cell.2020.06.034

  100. Jayaraman, J., Jesudoss, V.A.S., Menon, V.P., and Namasivayam, N., Toxicol. Mech. Methods, 2012, vol. 22, pp. 568–576. https://doi.org/10.3109/15376516.2012.707255

    Article  CAS  PubMed  Google Scholar 

  101. Madeswaran, A., Brahmasundari, S., and Midhuna, P.G., Eur. Rev. Med. Pharmacol. Sci., 2021, vol. 25, pp. 6741–6744. https://doi.org/10.26355/eurrev_202111_27119

    Article  CAS  PubMed  Google Scholar 

  102. Muschietti, L.V., Austin J. Pharmacol. Ther., 2021, vol. 9, Article ID: 1146. https://doi.org/10.26420/austinjpharmacolther.2021.1146

  103. Cheng, R.Z., Med. Drug Discov., 2020, vol. 5, p. 100028. https://doi.org/10.1016/j.medidd.2020.100028

    Article  PubMed  PubMed Central  Google Scholar 

  104. Tutunchi, H., Naeini, F., Ostadrahimi, A., and Hosseinzadeh-Attar, M.J., Phyther. Res., 2020, vol. 34, pp. 3137–3147. https://doi.org/10.1002/ptr.6781

    Article  CAS  Google Scholar 

  105. D’amore, A., Gradogna, A., Palombi, F., Minicozzi, V., Ceccarelli, M., Carpaneto, A., and Filippini, A., Cells, 2021, vol. 10, Article ID: 1130. https://doi.org/10.3390/cells10051130

  106. Alzaabi, M.M., Hamdy, R., Ashmawy, N.S., Hamoda, A.M., Alkhayat, F., Khademi, N.N., Al Joud, S.M.A., El-Keblawy, A.A., and Soliman, S.S.M., Phytochem. Rev., 2022, vol. 21, pp. 291–312. https://doi.org/10.1007/s11101-021-09759-z

    Article  CAS  PubMed  Google Scholar 

  107. Khaerunnisa, S., Kurniawan, H., Awaluddin, R., and Suhartati, S., Preprints, 2020, pp. 1–14. https://doi.org/10.20944/preprints202003.0226.v1

  108. Khan, N., Chen, X., and Geiger, J.D., J. Cell. Signal., 2021, vol. 2, pp. 63–79. https://doi.org/10.33696/signaling.2.036

    Article  PubMed  PubMed Central  Google Scholar 

  109. Rajamani, S., Sengodan, T., Radhakrishnan, A., and Shanmukhan, N., Asian J. Pharm., 2018, vol. 12, pp. S1201–S1207.

  110. Xu, D., Zhang, G.Q., Zhang, T.T., Jin, B., and Ma, C., J. Anal. Methods Chem., 2020, vol. 2020, Article ID: 8364218. https://doi.org/10.1155/2020/8364218

  111. Zhang, L., Song, L., Zhang, P., Liu, T., Zhou, L., Yang, G., Lin, R., and Zhang, J., J. Chem. Eng. Data, 2015, vol. 60, pp. 932–940. https://doi.org/10.1021/je501004g

    Article  CAS  Google Scholar 

  112. Xu, H., Kulkarni, K.H., Singh, R., Yang, Z., Wang, S.W.J., Tam, V.H., and Hu, M., Mol. Pharm., 2009, vol. 6, pp. 1703–1715. https://doi.org/10.1021/mp900013d

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  113. Chabane, M.N., Ahmad, A. Al, Peluso, J., Muller, C.D., and Ubeaud, G., J. Pharm. Pharmacol., 2009, vol. 61, pp. 1473–1483. https://doi.org/10.1211/jpp/61.11.0006

    Article  CAS  Google Scholar 

  114. Mata-Bilbao, M. de L., Andrés-Lacueva, C., Roura, E., Jáuregui, O., Escribano, E., Torre, C., and Lamuela-Raventós, R.M., Br. J. Nutr., 2007, vol. 98, pp. 86–92. https://doi.org/10.1017/S0007114507707262

    Article  CAS  PubMed  Google Scholar 

  115. Kanaze, F.I., Bounartzi, M.I., Georgarakis, M., and Niopas, I., Eur. J. Clin. Nutr., 2007, vol. 61, pp. 472–477. https://doi.org/10.1038/sj.ejcn.1602543

    Article  CAS  PubMed  Google Scholar 

  116. Gardana, C., Guarnieri, S., Riso, P., Simonetti, P., and Porrini, M., Br. J. Nutr., 2007, vol. 98, pp. 165–172. https://doi.org/10.1017/S0007114507699358

    Article  CAS  PubMed  Google Scholar 

  117. Rebello, C.J., Beyl, R.A., Lertora, J.J.L., Greenway, F.L., Ravussin, E., Ribnicky, D.M., Poulev, A., Kennedy, B.J., Castro, H.F., Campagna, S.R., Coulter, A.A., and Redman, L.M., Diabetes, Obes. Metab., 2020, vol. 22, pp. 91–98. https://doi.org/10.1111/dom.13868

    Article  CAS  PubMed  Google Scholar 

  118. Zeng, X., Su, W., Zheng, Y., He, Y., He, Y., Rao, H., Peng, W., and Yao, H., Front. Pharmacol., 2019, vol. 9, pp. 1–12. https://doi.org/10.3389/fphar.2019.00034

    Article  CAS  Google Scholar 

  119. El Mohsen, M.A., Marks, J., Kuhnle, G., Rice-Evans, C., Moore, K., Gibson, G., Debnam, E., and Srai, S.K., Free Radic. Res., 2004, vol. 38, pp. 1329–1340. https://doi.org/10.1080/10715760400017293

    Article  CAS  PubMed  Google Scholar 

  120. Justesen, U., Knuthsen, P., and Leth, T., J. Chromatogr. A, 1998, vol. 799, pp. 101–110. https://doi.org/10.1016/s0021-9673(97)01061-3

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

The authors thank the University Grant Commission, New Delhi for granting UGC-BSR Start-UP Project (No.F.30-477/ 2019 (BSR)).

Author information

Authors and Affiliations

  1. Department of Chemistry, Magadh Mahila College, Patna University, 800001, Patna, India

    A. Prasad

  2. Department of Chemistry, R.D.S. College, B.R.A. Bihar University, 842002, Muzaffarpur, India

    R. Kumar

  3. Department of Zoology, Magadh Mahila College, Patna University, 800001, Patna, India

    S. Kumari

Authors
  1. A. Prasad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Kumari
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Author AP conceptualisation, design, literature survey and draft manuscript preparation, writing bioactive effects in the draft. Author RK writing synthesis portion of the draft. Author SK writing pharmacokinetics. All authors reviewed and approved the final version of the article.

Corresponding author

Correspondence to A. Prasad.

Ethics declarations

This article does not contain any studies involving animals or human participants performed by any of the authors.

Informed consent was not required for this article. No conflict of interest was declared by the authors.

Additional information

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Prasad, A., Kumar, R. & Kumari, S. Recent Advances in Synthetic Aspects of Naringenin Flavonoid and its Bioprotective Effect (A Review). Russ J Bioorg Chem 49, 1177–1197 (2023). https://doi.org/10.1134/S106816202306002X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S106816202306002X

Keywords:

Search

Navigation