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Biologically Active Natural 2'-Hydroxychalcones

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Abstract—

The study provides modern data from the literature on the results of research in the field of flavonoids of medicinal plants. Systematization was carried out according to the most common structures of the isolated 2'-hydroxychalcones and their derivatives from 59 sources of natural raw materials. The data on the features of biogenesis, general characteristics, possible functions, biological properties and aspects of practical application are presented.

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REFERENCES

  1. Michael, S. and Marc, D., Epigenetic Cancer Ther., 2015, pp. 393–425. https://doi.org/10.1016/B978-0-12-800206-3.00018-5

  2. Ismailova, G.O., Karimova, Sh.F., Ziyamutdinova, Z.K., and Bakhodirova, M. A., Al’m. Sovrem. Nauki Obraz., Tambov: Gramota, 2016, no. 10 (112), pp. 36–45.

  3. Popova, A.V., Bondarenko, S.P., and Frasinyuk, M.S., Khim. Geterotsikl. Soedin., 2019, vol. 55, nos. 4/5, pp. 285–299.

    CAS  Google Scholar 

  4. Panasenko, A.I., Vestn. TGU, 2010, vol. 15, no. 1, pp. 62–64.

    Google Scholar 

  5. Bondakova, M.V., Formulation development and production technology of cosmetic products using grape extract, Cand. Sci. (Tech.) Dissertation, Moscow, 2014.

  6. Gouveia, M.G., Xavier, M.A., Barreto, A.S., Gelain, D.P., Santos, J.P., Araújo, A.A., Silva, F.A., Quintans, J.S., Agra, M.F., Cabral, A.G., Tavares, J.F., Silva, M.S., and Quintans-Júnior, L.J., J. Med. Food, 2011, vol. 14, no. 11, pp. 1389–1396. https://doi.org/10.1089/jmf.2010.0212

    Article  CAS  PubMed  Google Scholar 

  7. Anderson, A., J. Am. Coll. Nutr., 2001, vol. 20, no. 4, pp. 327–336.

    Article  Google Scholar 

  8. Stepkina, N.N. and Velikorodov, A.V., Fundam. Issled., 2015, no. 11, part 3, pp. 505–510. https://doi.org/10.17513/fr.39449

  9. Satyanarayama, M., Tiwari, P., Tripathi, K., Srivastava, A.K., and Pratap, R., Bioorg. Med. Chem., 2004, vol. 12, pp. 883–889. https://doi.org/10.1016/j.bmc.2003.12.026

    Article  CAS  Google Scholar 

  10. Ramirez, I., Carabot, A., Melendez, P., Carmona, J., Jimenez, M., Patel, A.V., Crabb, T.A., Blunden, G., Cary, P.D., Croft, S.L., and Costa, M., Phytochemistry, 2003, vol. 64, pp. 645–647. https://doi.org/10.1016/s0031-9422(03)00241-3

    Article  CAS  PubMed  Google Scholar 

  11. Lunardi, F., Guzela, M., Rodrigues, A.T., Corre, R., Eger-Mangrich, I., Steindel, M., Grisard, E.C., Assreuy, J., Calixto, J.B., and Santos, A.R., Antimicrob. Agents Chemother., 2003, vol. 47, pp. 1449–1451.

    Article  CAS  Google Scholar 

  12. Fabr, P., Puani, S., Belobr, F., and Mando, A., Monoterpene derivatives of chalcone or dihydrochalcone and their use as depigmenting agents, Inventor’s Certificate, no. 0002595860, no. 216.015.509E, Otkr., Izobret., 2020.

    Google Scholar 

  13. Yinning, C., Tao, Y., Chenghai, G., Wenhao, C., and Riming, H., Molecules J., 2014, vol. 19, pp. 1432–1458. https://doi.org/10.3390/molecules19021432

    Article  CAS  Google Scholar 

  14. Khan, S.A., Ahmed, B., and Alam, T., Pak. J. Pharm. Sci., 2006, vol. 19, pp. 290–294.

    CAS  PubMed  Google Scholar 

  15. Jun, N., Hong, G., and Jun, K., Bioorg. Med. Chem., 2007, vol. 15, pp. 2396–2402. https://doi.org/10.1016/j.bmc.2007.01.017

    Article  CAS  PubMed  Google Scholar 

  16. Liu, M., Wiliarat, P., and Croft, S.L., Bioorg. Med. Chem., 2003, vol. 11, pp. 2729–2738. https://doi.org/10.1016/S0968-0896(03)00233-5

    Article  CAS  PubMed  Google Scholar 

  17. Achanta, G., Modzelewska, A., Feng, L., Khan, S.R., and Huang, P.A., Mol. Pharmacol., 2006, vol. 70, pp. 426–433. https://doi.org/10.1124/mol.105.021311

    Article  CAS  PubMed  Google Scholar 

  18. Echeverria, C., Santibanez, J.F., Donoso-Tauda, O., Escobar, C.A., and Tagle, R.R., Int. J. Mol. Sci., 2009, vol. 10, pp. 221–231. https://doi.org/10.3390/ijms10010221

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Romagnoli, R., Baraldi, P.G., Carrion, M.D., Cara, C.L., Cruz-Lopez, O., and Preti, D., Bioorg. Med. Chem., 2008, vol. 16, pp. 5367–5376. https://doi.org/10.1016/j.bmc.2008.04.026

    Article  CAS  PubMed  Google Scholar 

  20. Meng, C.Q., Zheng, X.S., Ni, L., Ye, Z., Simpson, J.E., Worsencroft, K.J., Hotema, M.R., Weingarten, M.D., Skudlarek, J.W., Gilmore, J.M., Hoong, L.K., Hill, R.R., Marino, E.M., Suen, K.L., Kunsch, C., Wasserman, M.A., and Sikorski, J.A., Bioorg. Med. Chem. Lett., 2004, vol. 14, pp. 1513–1517. https://doi.org/10.1016/j.bmcl.2004.01.021

    Article  CAS  PubMed  Google Scholar 

  21. Nam, N.H., Kim, Y., You, Y.J., Hong, D.H., Kim, H.M., and Ahn, B.Z., Eur. J. Med. Chem., 2003, vol. 38, pp. 179–187. https://doi.org/10.1016/S0223-5234(02)01443-5

    Article  CAS  PubMed  Google Scholar 

  22. Sabzevarib, O., Galati, G., Moridani, M.Y., Siraki, A., and O’Brien, P.J., Chem.–Biol. Interact., 2004, vol. 148, pp. 57–67.

    Article  Google Scholar 

  23. Begum, N.A., Roy, N., Laskar, R.A., and Roy, K., Med. Chem. Res., 2011, vol. 20, pp. 184–191. https://doi.org/10.1007/s00044-010-9305-6

    Article  CAS  Google Scholar 

  24. Barford, L., Kemp, K., Hansen, M., and Kharazmi, A., Int. Immunopharmacol., 2002, vol. 2, pp. 545–550.

    Article  Google Scholar 

  25. Najafian, M., Ebrahim-Habibi, A., Hezareh, N., Yaghmaei, P., Parivar, K., and Larijani, B., Mol. Biol. Rep., 2010, vol. 10, pp. 271–274.

    Google Scholar 

  26. Zarghi, A., Zebardast, T., Hakimion, F., Shirazi, F.H., Rao, P.N.P., and Knaus, E.E., Bioorg. Med. Chem., 2006, vol. 14, pp. 7044–7050. https://doi.org/10.1016/j.bmc.2006.06.022

    Article  CAS  PubMed  Google Scholar 

  27. Chimenti, F., Fioravanti, R., Bolasco, A., Chimenti, P., Secci, D., Rossi, F., Yanez, M., Francisco, O.F., Ortuso, F., and Alcaro, S., J. Med. Chem., 2009, vol. 49, pp. 4912–4925.

    Google Scholar 

  28. Khatib, S., Nerua, O., Musa, R., Shmnell, M., Tamir, S., and Vaya, J., Bioorg. Med. Chem., 2005, vol. 13, pp. 433–441.

    Article  CAS  Google Scholar 

  29. Bruno, B., Alberto, V., Pilar, M., Domenico, M., and Giuliano, D.M., Curr. Med. Chem., 2005, no. 6, pp. 713–739. https://doi.org/10.2174/0929867053202241

  30. Hatano, T., Kusudo, M., Inada, K., Ogawa, T., Shiota, S., Tsuchiya, T., and Yoshida, T., Phytochemistry, 2005, vol. 66, pp. 2047–2055.

    Article  CAS  Google Scholar 

  31. Shmuilovich, K., Interaction of polyfluorinated chalcones with binucleophilic reagents, Cand. Sci. (Chem.) Dissertation, Novosibirsk, 2014.

  32. Tiwari, K.N., Monserrat, J.-P., Arnaud, HequetA., Ganem-Elbaz, C., Cresteil, T., Jaouen, G., Vessieres, A., Hillard, E.A., and Jolivalt, C., Dalton Trans., 2012, vol. 41, pp. 6451–6457.

    Article  CAS  Google Scholar 

  33. Bhatia, N.M., Mahadik, K.R., and Bhatia, M.S., Chem. Pap., 2009, vol. 63, pp. 456–463. https://doi.org/10.2478/s11696-009-0026-6

    Article  CAS  Google Scholar 

  34. Hamdi, N., Fischmeister, C., Puerta, M.C., and Valerga, P., Med. Chem. Res., 2011, vol. 20, pp. 522–530. https://doi.org/10.1007/s00044-010-9326-1

    Article  CAS  Google Scholar 

  35. Bonakdar, A.P.S., Sadeghi, A., Aghaei, H.R., Beheshtimaal, K., Nazifi, S.M.R., and Massah, A.R., Russ. J. Bioorg. Chem., 2020, vol. 46, pp. 371–381. https://link.springer.com/journal/11171/46/3.

    Google Scholar 

  36. Dao, T.T., Nguyen, P.H., Lee, H.S., Kim, E., Park, J., Lim, S., and Oh, W.K., Bioorg. Med. Chem. Lett., 2011, vol. 21, pp. 294–298. https://doi.org/10.1016/j.bmcl.2010.11.016

    Article  CAS  PubMed  Google Scholar 

  37. Yenesew, A., Induli, M., Derese, S., Midiwo, J.O., Heydenreich, M., Peter, M.G., Akala, H., Wangui, J., Liyala, P., and Waters, N.C., Phytochemistry, 2004, vol. 65, pp. 3029–3032. https://doi.org/10.1016/j.phytochem.2004.08.050

    Article  CAS  PubMed  Google Scholar 

  38. Portet, B., Fabre, N., Roumy, V., Gornitzka, H., Bourdy, G., Chevalley, S., Sauvain, M., Valentin, A., and Moulis, C., Phytochemistry, 2007, vol. 68, pp. 1312–1320. https://doi.org/10.1016/j.phytochem.2007.02.006

    Article  CAS  PubMed  Google Scholar 

  39. Yenesew, A., Derese, S., Midiwo, J.O., Oketch-Rabah, H.A., Lisgarten, J., Palmer, R., Heydenreich, M., Peter, M.G., Akala, H., Wangui, J., Liyala, P., and Waters, N.C., Phytochemistry, 2003, vol. 64, pp. 773–779. https://doi.org/10.1016/s0031-9422(03)00373-x

    Article  CAS  PubMed  Google Scholar 

  40. Jayasinghe, L., Balasooriya, B.A.I.S., Padmini, W.C., Hara, N., and Fujimoto, Y., Phytochemistry, 2004, vol. 65, pp. 1287–1290.

    Article  CAS  Google Scholar 

  41. Epifano, F., Genovese, S., Menghini, L., and Curini, M., Phytochemistry, 2007, vol. 68, pp. 939–953. https://doi.org/10.1016/j.phytochem.2007.01.019

    Article  CAS  PubMed  Google Scholar 

  42. Jayasinghe, L., Rupasinghe, G., Hara, N., and Fujimoto, Y., Phytochemistry, 2006, vol. 67, pp. 1353–1358.

    Article  CAS  Google Scholar 

  43. Apak, R., Guclu, K., Demirata, B., Ozyurek, M., Celik, S.E., Bektasoglu, B., Berker, K.I., and Ozyurt, D., Molecules J., 2007, vol. 12, pp. 1496–1547. https://doi.org/10.3390/12071496

    Article  CAS  Google Scholar 

  44. Bajgai, E.S., Prachyawarakarn, V., Mahidol, C., Ruchirawat, S., and Kittakoop, P., Phytochemistry, 2011, vol. 72, pp. 2062–2067.

    Article  CAS  Google Scholar 

  45. Stevens, J.F. and Page, J.E., Phytochemistry, 2004, vol. 65, pp. 1317–1330. https://doi.org/10.1016/j.phytochem.2004.04.025

    Article  CAS  PubMed  Google Scholar 

  46. Prachayasittikul, S., Buraparuangsang, P., Worachartcheewan, A., Isarankura-Na-Ayudhya, C., Ruchirawat, S., and Prachayasittikul, V., Molecules J., 2008, vol. 13, pp. 904–921. https://doi.org/10.3390/molecules13040904

    Article  CAS  Google Scholar 

  47. Kurkin V.A., Kurkina A.V., Avdeeva E.V., Ratsion. Pitan., Pishch. Dobavki Biostimulyatory, 2014, no. 4, p. 26.

  48. Nerya, O., Musa, R., Khatib, S., Tamir, S., and Vaya, J., Phytochemistry, 2004, vol. 65, pp. 1389–1395. https://doi.org/10.1016/j.phytochem.2004.04.016

    Article  CAS  PubMed  Google Scholar 

  49. Calliste, C.A., Le Bail, J.C., Trouilas, P., Pouget, C., Habrioux, G., and Chulia, A.J., Anticancer Res., 2001, vol. 21, pp. 3949–3956.

    CAS  PubMed  Google Scholar 

  50. Bo, Han., Zheng, Q., Wang, J., Chen, W., Tang, H., Qi, Wang., Wang, X., and Ji, Li., Khim. Prir. Soedin., 2010, no. 4, pp. 443–446.

  51. Martinez-Luis, S., Perez-Vasquez, A., and Mata, R., Phytochemistry, 2007, vol. 68, pp. 1882–1903. https://doi.org/10.1016/j.phytochem.2007.02.025

    Article  CAS  PubMed  Google Scholar 

  52. Meazza, G., Scheffler, B.E., Tellez, M.R., Rimando, A.M., Romagni, J.G., Duke, S.O., Nanayakkara, D., Khan, I.A., Abourashed, E.A., and Dayan, F.E., Phytochemistry, 2002, vol. 59, pp. 281–288.

    Article  Google Scholar 

  53. Haraguchi, H., Tanaka, Y., Kabbash, A., Fujioka, T., Ishizu, T., and Yagi, A., Phytochemistry, 2004, vol. 65, pp. 2255–2260. https://doi.org/10.1016/s0031-9422(03)00516-8

    Article  CAS  PubMed  Google Scholar 

  54. Eckermann, C., Matthes, B., Nimtz, M., Reiser, V., Lederer, B., Boger, P., and Schroder, J., Phytochemistry, 2003, vol. 64, pp. 1045–1054. https://doi.org/10.1016/s0031-9422(03)00516-8

    Article  CAS  PubMed  Google Scholar 

  55. Bastos dos Santos, M., Bertholin Anselmo, D., Gisleine de Oliveira, J., Jardim-Perassi, B.V., et al., Antiproliferative activity and p53 upregulation effects of chalcones on human breast cancer cells, J. Enzyme Inhib. Med. Chem., 2019, pp. 1093–1099. https://doi.org/10.1080/14756366.2019.1615485

  56. Hsieh, H.K., Tsao, L.T., Wang, J.P., and Lin, C.N., J. Pharm. Pharmacol., 2000, vol. 52, pp. 163–171. https://doi.org/10.1211/0022357001773814

    Article  CAS  PubMed  Google Scholar 

  57. Won, S.J., Liu, C.T., Tsao, L.T., Weng, J.R., Ko, H.H., Wang, J.P., and Lin, C.N., Eur. J. Med. Chem., 2005, vol. 40, pp. 103–112. https://doi.org/10.1016/j.ejmech.2004.09.006

    Article  CAS  PubMed  Google Scholar 

  58. Okunade, A.L., Elvin-Lewis, M.P.F., and Lewis, W.H., Phytochemistry, 2004, vol. 65, pp. 1017–1032. https://doi.org/10.1016/j.phytochem.2004.02.013

    Article  CAS  PubMed  Google Scholar 

  59. Aitmambetov, A., Ibragimova, Z.Yu., Khozhambergenov, K., and Ibragimov, M.Yu., Teoret. Klin. Med. (Tashkent), 2006, no. 5, p. 184.

  60. Hyun, AhJ., Takako, Y., Byung-Woo, K., Jee, H.J., and Jae, S.Ch., Am. J. Chin. Med., 2010, no. 2, pp. 415–429. https://doi.org/10.1142/S0192415X10007944

  61. Hongyu, W., Tingting, L., and Dejian, H., Adv. Food Nutr. Res., 2013, vol. 70, pp. 103–136. https://doi.org/10.1016/B978-0-12-416555-7.00003-5

    Article  CAS  Google Scholar 

  62. Yue, Y., Xuchao, J., Haihui, X., and Xiaoyi, W., Phytochemistry, 2020, p. 174. https://doi.org/10.1016/j.phytochem.2020.112364

  63. Toshihiro, A., Harukuni, T., Motohiko, U., Masao, I., Stefan, S., Kazuya, O., Teruo, M., Kenji, I., Takashi, S., and Hoyoku, N., Cancer Lett., 2003, vol. 201, no. 2, pp. 133–137. https://doi.org/10.1016/S0304-3835(03)00466-X

    Article  CAS  Google Scholar 

  64. Rosa, M.P.G., Alethia, M-R., and Jahel, V.S., Afr. J. Pharm. Pharmacol., 2015, vol. 9, no. 8, pp. 237–257. https://doi.org/10.5897/AJPP2015.4267

    Article  Google Scholar 

  65. Hyung, W.R., Mi, H.P., Ok-Kyoung, K., Doo-Young, K., Jung-Yeon, H., Yang, H.Jo., Kyung-Seop, A., and Bang, Y.H., Bioorg. Chem., 2019, vol. 92, p. 103233. https://doi.org/10.1016/j.bioorg.2019.103233

    Article  CAS  Google Scholar 

  66. Tamires, C.L., Rafaela, J.S., Alan, D.C.S., Milene, H.M., Nicole, E.B., Andersson, B., Mário, S., and Maique, W.B., Nat. Prod. Res., vol. 30, no. 5, pp. 1–7. https://doi.org/10.1080/14786419.2015.1030740

  67. Øyvind, M.A. and Monica, J., Compr. Nat. Prod. II, 2010, vol. 3, pp. 547–614. https://doi.org/10.1016/B978-008045382-8.00086-1

    Article  Google Scholar 

  68. Dykens, J.A., Compr. Med. Chem. II, 2007, vol. 2, pp. 1053–1087. https://doi.org/10.1016/B0-08-045044-X/00071-7

    Article  Google Scholar 

  69. Fera, K., Lia, D.J., Yana, M.S., Sjamsul, A.A., Euis, H.H., Kiyotaka, K., Kaoru, K., and Kunio, T., J. Nat. Med., 2010, vol. 64, pp. 121–125. https://doi.org/10.1007/s11418-009-0368-y

    Article  CAS  Google Scholar 

  70. Anam Edet, M.U., Russ. Zh. Khim., 2000, vol. 2, p. 206. 19E.

  71. Krasnov, E.A., Ermilova, E.V., Kadyrova, T.V., Raldugin, V.A., Bagryanskaya, I.Yu., Gatilov, Yu.V., Druganov, A.G., Semenov, A.A., and Tolstikov, G.A., Khim. Prir. Soed., 2000, no. 5, pp. 389–391.

  72. Fuendjiep, V., Wandji, J., Tillequin, F., Mulholland, D.A., Budzikiewicz, H., Fomum, Z.T., Nyemba, A.M., and Koch, M., Phytochemistry, 2002, no. 8, pp. 803–806. https://doi.org/10.1016/s0031-9422(02)00108-5

  73. Boonchoo, S., Kittisak, L., Jurgen, C., and Wolfgang, K., Phytochemistry, 2002, no. 8, pp. 943–947. https://doi.org/10.1016/s0031-9422(02)00337-0

  74. Lim, S.H., Ha, T.Y., Ahn, J., and Kim, S., Phytomedicine, 2011, vol. 18, pp. 425–430. https://doi.org/10.1016/j.phymed.2011.02.002

    Article  CAS  PubMed  Google Scholar 

  75. oseph, A., Sandra, D., Matthias, H., Lois, M-M., Vicky, M.A., Mate, E., and Abiy, Y., Molecules, 2017, no. 2, p. 318. 10.3390/molecules2202031

  76. Panthati, M.K., Rao, K.N.V., Sandhya, S., and David, B., Braz. J. Pharmacogn., 2012, vol. 22, pp. 1145–1154.

    Article  Google Scholar 

  77. Motahare, B., Saba, S., and Mehrdad, I., Phytother. Res., 2019, no. 3, pp. 546–560. https://doi.org/10.1002/ptr.6265

  78. Handbook of Dietary Phytochemicals, Xiao, J., , Eds., Springer Nature Singapore Pte Ltd., 2020. https://doi.org/10.1007/978-981-13-1745-3_10-1

    Book  Google Scholar 

  79. Federico, G-G., Oswaldo, T-V., Gregorio, M-T., and Jose, S.C., Zeitschrift Naturforschung, 2014, nos. 7–8, pp. 579–583. https://doi.org/10.1515/znc-2002-7-805

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Ismailova, G.O., Yuldashev, N.M., Akbarhodjaeva, K.N. et al. Biologically Active Natural 2'-Hydroxychalcones. Russ J Bioorg Chem 47, 660–669 (2021). https://doi.org/10.1134/S1068162021030080

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