STRUCTURE AND BIOMEDICAL PROPERTIES OF LIGNINS (REVIEW)
UDC 547.458.82
Abstract
The proposed literature review is in line with current trends in the development of nature-like technologies and is devoted to the analysis of the chemical structure and the search for new ways to use lignins for biomedical applications. Lignins are unique biopolymers of plant origin, the structural organization of which is multivariate and largely depends on the biological species of the plant. Fundamental structural and chemical studies are increasingly clarifying our understanding of the macromolecules structure of this key plant biopolymer, and the study of various taxonomic origins lignins shows to what extent evolution and natural variability have led to a complication of the chemical structure of macromolecules, including through the inclusion of "unconventional" phenolic monomers. This suggests that lignins contain much more structural units than the three monolignol variants described in lignin chemistry textbooks. As a result, as the analysis of the literature data shows, the very definition of lignin continues to expand and refine. Currently, there is a dramatic increase in interest in lignin-based materials, mainly due to their diverse beneficial properties, such as biodegradability, reactivity, biocompatibility, low toxicity and a wide range of biological activity. One of the main objectives of this article is to identify and discuss the mechanisms of biological action of lignins on living organisms to assess the biomedical potential and substantiate the possibility of their use as innovative drugs of antioxidant, radioprotective and geroprotective action. Finding new ways to use lignins is necessary to meet the challenges of maintaining health and improving the quality and duration of people's lives.
Downloads
Metrics
References
Zhang C., Liu Y., Liu X., Chen X., Chen R. Molecules, 2023, vol. 28 (1), p. 365.
Karmanov A.P., Kocheva L.S., Karmanova Yu.A. Khimiya Rastitel’nogo Syr’ya, 2015, no. 4, pp. 109–114. (in Russ.).
Xue J.Y., Hind K.R., Lemay M.A., Mcminigal A., Jourdain E., Chan C.X., Martone P.T. PLoS ONE, 2022, vol. 17 (7), article e0266892. DOI: 10.1371/journal.pone.0266892.
Han X., Zhao Y., Chen Y., Xu J., Jiang C. et al. Forestry Research. 2022, vol. 2 (9). DOI: 10.48130/FR-2022-0009.
Lu X., Gu X., Shi Y. International Journal of Biological Macromolecules, 2022, vol. 210, pp. 716–741. DOI: 10.1016/j.ijbiomac.2022.04.228.
Domínguez-Robles J., Cárcamo-Martínez Á., Stewart S.A., Donnelly R.F., Larrañeta E., Borrega M. Sustainable Chemistry and Pharmacy, 2020, vol. 18, article 100320.
Liu Q., Luo L., Zheng L. Int. J. Molec. Sci., 2018, vol. 19, p. 335. DOI: 10.3390/ijms19020335.
Sugiarto S., Leow Y., Tan C. L., Wang G., Kai D. Bioactive Materials, 2022, vol. 8, pp. 71–94.
Ralph J., Lapierre C., Boerjan W. Curr. Opin. Biotechnol., 2019, vol. 56, pp. 240–249. DOI: 10.1016/j.copbio.2019.02.019.
Rencoret J., Kim H., Evaristo A.B., Gutiérrez A., Ralph J., Del Río J.C. Journal of agricultural and food chemistry, 2018, vol. 66 (1), pp. 138–153.
Reyt G., Ramakrishna P., Salas-González I., Fujita S., Love A., Tiemessen D., Lapierre C., Morree K., Calvo-Polanco M., Flis P., Geldner N., Boursiac Ya., Boerjan W., George M.W., Castrillo G., Salt D.E. Nat. Comm., 2021, vol. 12, pp. 1–15. DOI: 10.1038/s41467-021-22550-0.
Mottiar Y., Smith R.A., Karlen S.D., Ralph J., Mansfield S.D. New Phytologist, 2022, vol. 237 (1), pp. 251–264. DOI: 10.1111/nph.18518.
Mottiar Y., Vanholme R., Boerjan W., Ralph J., Mansfield S.D. Current Opinion in Biotechnology, 2016, vol. 37, pp. 190–200.
Österberg M., Sipponen M.H., Mattos B.D., Rojas O.J. Green Chemistry, 2020, vol. 22 (9), pp. 2712–2733.
De Meester B., Vanholme R., Mota T., Boerjan W. Plant Communications, 2022, vol. 3 (6), article 100465. DOI: 10.1016/j.xplc.2022.100465.
Dixon R.A., Barros J. Open Biology, 2019, vol. 9 (12), article 190215.
Gellerstedt G., Henriksson G., Belgacem M.N., Gandini A. Monomers Polym. Compos. Renew. Resour. Elsevier, Am-sterdam, 2008, pp. 201–224.
Ralph J., Brunow G., Harris P.J., Dixon R.A., Schatz P.F., Boerjan W. Recent Advances in Polyphenol Research. Wiley-Blackwell Publishing, 2008, vol. 1, pp. 36–66.
Zhao Q. Trends in plant science, 2016, vol. 21 (8), pp. 713–721.
Mottiar Y., Vanholme R., Boerjan W., Ralph J., Mansfield S.D. Current Opinion in Biotechnology, 2016, vol. 37, pp. 190–200.
Kärkönen A., Koutaniemi S. Journal of integrative plant biology, 2010, vol. 52 (2), pp. 176–185.
Shao-Ying G., Mlynár J., Sarkanen S. Phytochemistry, 1997, vol. 45 (5), pp. 911–918. DOI: 10.1016/S0031-9422(97)00077-0.
Karmanov A.P., Matveev D.V., Monakov Yu.B. Doklady Chemistry. 2001, vol. 380 (4–6), pp. 280–283.
Li Q., Koda K., Yoshinaga A., Takabe K., Shimomura M., Hirai Y. et al. Journal of agricultural and food chemistry, 2015, vol. 63 (18), pp. 4613–4620.
Lyu Y., Suzuki S., Nagano H., Shigetomi K., Tamai Y., Tsutsumi Y., Uraki Y. Carbohydrate Polymers, 2023, vol. 301, article 120305.
Chen F., Tobimatsu Y., Havkin-Frenkel D., Dixon R.A., Ralph J. Proceedings of the National Academy of Sciences, 2012, vol. 109 (5), pp. 1772–1777.
Faraji M., Fonseca L.L., Escamilla-Treviño L., Barros-Rios J., Engle N., Yang Z.K. et al. Biotechnology for biofuels, 2018, vol. 11 (1), pp. 1–17.
Karmanov A.P., Poleshchikov S.M. Khimiya Rastitel’nogo Syr’ya, 2019, no. 1, pp. 63–72. (in Russ.).
Zhang L., Larsson A., Moldin A., Edlund U. Industrial Crops and Products, 2022, vol. 187, article 115432.
Karmanov A.P., Kanarsky A.V., Kocheva L.S., Belyy V.A., Semenov E.I., Rachkova N.G., Bogdanovich N.I., Pokryshkin S.A. Polymer, 2021, vol. 220, article 123571. DOI: 10.1016/j.polymer.2021.123571.
Pesquet E., Wagner A., Grabber J.H. Current opinion in biotechnology, 2019, vol. 56, pp. 215–222. DOI: 10.1016/j.copbio.2019.02001.
Rosado M.J., Rencoret J., Marques G., Gutiérrez A., Del Río J.C. Frontiers in Plant Science, 2021, vol. 12, article 640475. DOI: 10.3389/fpls.2021.640475.
Qin Z., Yang Q.L., Cheng X.C., Liu H.M., Wang X.D. Industrial Crops and Products, 2021, vol. 169, article 113677. DOI: 10.1016/j.indorop.2021.113677.
Popova Y.A., Shestakov S.L., Belesov A.V., Pikovskoi I.I., Kozhevnikov A.Y. International Journal of Biological Macromolecules, 2020, vol. 164, pp. 3814–3822. DOI: 10.1016/j.ijbiomac.2020.08.240.
Shi Z., Xu G., Deng J., Dong M., Murugadoss V., Liu C. et al. Green Chemistry Letters and Reviews, 2019, vol. 12 (3), pp. 235–243. DOI: 10.1080/17518253.2019.1627428.
Karmanov A.P., Kanarsky A.V., Kocheva L.S., Semenov E.I., Belyy V.A. Reactive and Functional Polymers, 2021, vol. 167, article 105033. DOI: 10.1016/j.reactfunctpolym.2021.105033.
Wang W.Y., Qin Z., Liu H.M., Wang X.D., Gao J.H., Qin G.Y. Molecules, 2021, vol. 26 (2), p. 398. DOI: 10.3390/molecules26020398.
Branco D.G., Santiago C., Lourenco A., Cabrita L., Evtuguin D.V. Journal of Agricultural and Food Chemistry, 2021, vol. 69 (30), pp. 8555–8564. DOI: 10.1021/acs.jafc.1c01961.
Karmanov A.P., Kocheva L.S., Belyaev V.Y., Brovko O.S., Ovodov Y.S. Izvestiya VUZov. Lesnoy zhurnal, 2013, no. 1, pp. 137–145. (in Russ.).
Wang J., Wang S. Journal of Cleaner Production, 2019, vol. 227, pp. 1002–1022.
Yuan J.M., Li H., Xiao L.P., Wang T.P., Ren W.F., Lu Q., Sun R.C. Fuel, 2022, vol. 319, article 123758.
Smith R.A., Lu F., Muro-Villanueva F., Cusumano J.C., Chapple C., Ralph J. Plant and Cell Physiol., 2022, vol. 63, pp. 744–754. DOI: 10.1093/pcp/pcac051.
Sun R.C. ChemSusChem., 2020, vol. 13 (17), pp. 4385–4393.
Barsberg S.T., Lee Y.I., Rasmussen H.N. Seed Science Research, 2018, vol. 28 (1), pp. 41–51.
Wang S., Shen Q., Su S., Lin J., Song G. Trends in Chemistry, 2022, vol. 4, no. 10, pp. 948–961.
Song W., Du Q., Li X., Wang S., Song G. ChemSusChem., 2022, vol. 15 (14), article e202200646.
Wang S., Su S., Xiao L.P., Wang B., Sun R.C., Song G. ACS Sustainable Chemistry & Engineering, 2020, vol. 8 (18), pp. 7031–7038.
del Río J.C., Rencoret J., Gutiérrez A., Elder T., Kim H., Ralph J. ACS Sustainable Chemistry & Engineering, 2022, vol. 8 (13), pp. 4997–5012.
Li M., Pu Y., Meng X., Chen F., Dixon R.A., Ragauskas A.J. Green Chemistry, 2022, vol. 24 (1), pp. 259–270.
José C., Rencoret J., Gutiérrez A., Kim H., Ralph J. Advances in Botanical Research, 2022, vol. 104, pp. 1–39.
Rosado M.J., Rencoret J., Marques G., Gutiérrez A., Del Río J.C. Frontiers in Plant Science, 2021, vol. 12, article 640475.
Lam P.Y., Lui A.C., Wang L., Liu H., Umezawa T., Tobimatsu Y., Lo C. Frontiers in Plant Science, 2021, vol. 12, ar-ticle 733198.
Xie M., Chen Z., Xia Y., Lin M., Li J., Lan W. et al. Frontiers in Energy Research, 2021, vol. 9, article 756285.
del Río J.C., Rencoret J., Gutiérrez A., Lan W., Kim H., Ralph J. Recent advances in polyphenol research, 2021, vol. 7, pp. 177–206.
Ando D., Lu F., Kim H., Eugene A., Tobimatsu Y., Vanholme R. et al. Green Chemistry, 2021, vol. 23 (22), pp. 8995–9013.
Rencoret J., Rosado M.J., Kim H., Timokhin V.I., Gutiérrez A., Bausch F. et al. Plant Physiology, 2022, vol. 188 (1), pp. 208–219.
Elder T., Rencoret J., del Río J.C., Kim H., Ralph J. Frontiers in Plant Science, 2021, vol. 12, article 642848. DOI: 10.3389/fpls.2021.642848.
Lawoko M., Berglund L., Johansson M. ACS Sustainable Chemistry & Engineering, 2021, vol. 9 (16), pp. 5481–5485. DOI: 10.1021/acssuschemeng.1c01741.
Tao J., Li S., Ye F., Zhou Y., Lei L., Zhao G. Crit. Rev. Food Sci., 2020, vol. 60 (12), pp. 2011–2033. DOI: 10.1080/10408398.2019.1625025.
Lourenço A., Pereira H. Lignin-trends and applications, 2018, pp. 65–98.
Yadav V.K., Gupta N., Kumar P., Dashti M.G., Tirth V., Khan S. H. et al. Materials, 2022, vol. 15 (3), p. 953.
Balakshin M., Capanema E.A., Zhu X., Sulaeva I., Potthast A., Rosenau T., Rojas O.J. Green Chemistry, 2020, vol. 22 (13), pp. 3985–4001.
Su X., Fu Y., Shao Z., Qin M., Li X., Zhang F. Industrial Crops and Products, 2022, vol. 176, article 114359.
Nadányi R., Ház A., Lisý A., Jablonský M., Šurina I., Majová V., Baco A. Energies, 2022, vol. 15 (18), article 6520.
Liu X., Bouxin F.P., Fan J., Budarin V.L., Hu C., Clark J.H. ChemSusChem., 2020, vol. 13, pp. 4296–4317.
Huang J., Fu S., Gan L. Lignin Chemistry and Applications. Elsevier: Amsterdam, 2019, pp. 25–50.
Zhang H., Zhao Y., Zhu J.K. Developmental Cell., 2020, vol. 55 (5), pp. 529–543. DOI: 10.1016/j.devcel.2020.10.012.
Šamec D., Karalija E., Šola I., Vujčić Bok V., Salopek-Sondi B. Plants, 2021, vol. 10, p. 118. DOI: 10.3390/plants10010118.
Cesarino I. Curr. opinion in biotech., 2019, vol. 56, pp. 209–214. DOI: 10.1016/j.copbio.2018.12.012.
Pellegrini E., Campanella A., Cotrozzi L., Tonelli M., Nali C., Lorenzini G. Environmental Science and Pollution Re-search, 2018, vol. 25 (9), pp. 8148–8160. DOI: 10.1007/s11356-017-8818-7.
Espinosa-Leal C.A., Mora-Vásquez S., Puente-Garza C.A., Alvarez-Sosa D.S., García-Lara S. Plant Growth Regula-tion, 2022, pp. 1–20. DOI: 10.1007/s10725-022-00810-3.
Ninkuu V., Yan J., Fu Z., Yang T., Ziemah J., Ullrich M.S. et al. Journal of Fungi, 2023, vol. 9 (1), p. 52. DOI: 10.3390/jof9010052.
Chen K., Guo Y., Song M., Liu L., Xue H., Dai H., Zhang Z. Horticulture research, 2020, vol. 7, p. 204. DOI: 10.1038/s41438-020-00433-7.
Liu W.G., Hussain S., Ting L.I.U., Zou J.L., Ren M.L., Tao Z.H.O.U. et al. Journal of integrative agriculture, 2019, vol. 18 (1), pp. 43–53. DOI: 10.1016/S2095-3119(18)61905-7.
Lu Y.C., Lu Y., Fan X. Structure and characteristics of lignin. Lignin: Biosynthesis and Transformation for Industrial Applications. Springer, 2020, pp. 17–75.
Alzagameem A., Klein S.E., Bergs M., Do X.T., Korte I., Dohlen S., Huwe C., Kreyenschmidt J., Kamm B., Lar-kins M., Schulze M. Polymers, 2019, vol. 11 (4), article 670.
Agrawal R., Kumar A., Singh S., Sharma K. Journal of Polymer Research, 2022, vol. 29 (6), p. 222.
Espinoza-Acosta J.L., Torres-Chávez P.I., Ramírez-Wong B., López-Saiz C.M., Montaño-Leyva B. BioResources, 2016, vol. 11 (2), pp. 5452–5481.
Heitner C., Dimmel D., Schmidt J. Lignin and lignans: advances in chemistry. CRC press, 2016. 684 p.
Watson R.R., Preedy V.R., Zibadi S. Polyphenols: Mechanisms of Action in Human Health and Disease. Academic Press Inc, 2018, vol. 1, 472 p.
Vinardell M.P., Mitjans M. International Journal of Molecular Sciences, 2017, vol. 18 (6), pp. 1–15. DOI: 10.3390/ijms18061219.
Singh S.K. International Journal of Biological Macromolecules, 2019, vol. 132, pp. 265–277. DOI: 10.1016/j.ijbiomac.2019.03.182.
Sato S., Mukai Y., Yamate J., Norikura T., Morinaga Y., Mikame K., Funaoka M., Fujita S. Free Radical Research, 2009, vol. 43, pp. 1205–1213. DOI: 10.3109/10715760903247264.
Saluja B., Thakkar J.N., Li H.; Desai U.R., Sakagami M. Pulmonary Pharmacology and Therapeutics, 2013, vol. 26, pp. 296–3043. DOI: 10.1016/j.pupt.2012.12.009.
Mehta A.Y., Mohammed B.M., Martin E.J., Brophy D.F., Gailani D., Desai U.R. Journal of Thrombosis and Haemo-stasis, 2016, vol. 14 (4), pp. 828–838.
Revajová V., Levkut M., Levkutová M., Bořutová R., Grešaková Ľ., Košiková B., Leng Ľ. Acta Veterinaria Hungari-ca, 2013, vol. 61 (3), pp. 354–365.
Heiss C., Spyridopoulos I., Haendeler J. Experimental Gerontology, 2018, vol. 109, pp. 108–118. DOI: 10.1016/j.exger.2017.06.015.
Borisenkov M.F., Karmanov A.P., Kocheva L.S. Uspekhi gerontologii, 2005, no. 17, pp. 34–41. (in Russ.).
Hudlikar R.R., Venkadakrishnan V.B., Kumar R., Thorat R.A., Kannan S., Ingle A.D., Desai S., Maru G.B., Mahimkar M.B. Molecular Carcinogenesis, 2017, vol. 56, pp. 625–640. DOI: 10.1002/ mc.22521.
Gonzalez de Mejia E., Loarca-Pina G. Food Research International, 2018, vol. 105, pp. 159–168. DOI: 10.1016/j.foodres.2017.11.004.
Liu D., He B., Lin L., Malhotra A., Yuan N. Drug and Chemical Toxicology, 2019, vol. 42, pp. 328–334. DOI: 10.1080/01480545.2018.1523921.
Figueiredo P., Lintinen K., Kiriazis A., Hynninen V., Liu Z., Bauleth-Ramos T. et al. Biomaterials, 2017, vol. 121, pp. 97–108. DOI: 10.1016/j.biomaterials.2016.12.034.
Panchenko A.V., Fedoros E.I., Pigarev S.E., Maydin M.A., Gubareva E.A., Kireeva G. S., Tyndyk M.L., Kuz-netsova A.I., Nekhaeva T.L., Danilova A.B., Baldueva I.A., Anisimov V.N. Integrative Cancer Therapies, 2019, vol. 18, pp. 1–13. DOI: 10.1177/1534735419833778.
Saratale R.G., Saratale G.D., Ghodake G., Cho S.-K., Kadam A., Kumar G., Jeon S.-H., Pant D., Bhatnagar A., Shin H.S. International Journal of Biological Macromolecules, 2019, vol. 128, pp. 391–400. DOI: 10.1016/j.ijbiomac.2019.01.120.
Schneider W.D.H., Dillon A.J.P., Camassola M. Biotechnology Advances, 2021, vol. 47, article 107685. DOI: 10.1016/j.biotechadv.2020.107685.
Verdini F., Calcio Gaudino E., Canova E., Tabasso S., Jafari Behbahani P., Cravotto G. Molecules, 2022, vol. 27 (11), article 3598. DOI: 10.3390/molecules27113598.
Ali D.A., Mehanna M.M. International Journal of Biological Macromolecules, 2022, vol. 221, pp. 934–953. DOI: 10.1016/j.ijbiomac.2022.09.007.
Liu R., Dai L., Xu C., Wang K., Si C., Zheng C. ChemSusChem., 2020, vol. 13 (17), pp. 4266–4283. DOI: 10.1002/cssc.202000783.
Sipponen M.H., Lange H., Crestini C., Henn A., Österberg M. ChemSusChem., 2019, vol. 12 (10), pp. 2039–2054. DOI: 10.1002/cssc.201900480.
Figueiredo P., Lintinen K., Hirvonen J.T., Kostiainen M.A., Santos H.A. Progress in Materials Science, 2018, vol. 93, pp. 233–269.
Xu J., Xu J.J., Lin Q., Jiang L., Zhang D., Li Z. et al. ACS Applied Bio Materials, 2020, vol. 4 (1), pp. 3–13. DOI: 10.1021/acsabm.0c00858.
Roopan S.M. International Journal of Biological Macromolecules, 2017, vol. 103, pp. 508–514. DOI: 10.1016/j.ijbiomac.2017.05.10.
Li S.-X., Li M.-F., Bing J., Wu X.-F., Peng F., Ma M.-G. International Journal of Biological Macromolecules, 2019, vol. 132, pp. 836–843. DOI: 10.1016/j.ijbiomac.2019.03.17.
Sunthornvarabhas J., Rungthaworn P., Sukatta U., Juntratip N., Sriroth K. Sugar Tech., 2020, vol. 22, pp. 697–705. DOI: 10.1007/s12355-019-00778-x.
Lobo F.C.M., Franco A.R., Fernandes E.M., Reis R.L. Molecules, 2021, vol. 26 (6), article 1749.
Gujjala L.S., Kim J., Won W. Journal of Cleaner Production, 2022, vol. 363, article 132585. DOI: 10.1016/j.jclepro.2022.132585.
Chen M., Li Y., Liu H., Zhang D., Shi Q.-S., Zhong X.-Q., Guo Y., Xie X.-B. Materials Today Bio, 2022, vol. 18, ar-ticle 100520. DOI: 10.1016/j.mtbio.2022.100520.
Moreira W.M., Moreira P.V.V., Dos Santos D.F., Gimenes M.L., Vieira M.G.A. Environmental Science and Pollution Research, 2023, vol. 30(8), pp. 19564–19591. DOI: 10.1007/s11356-023-25150-1.
Raghuraman M., Verma P., Kunwar A., Phadnis P. P., Jain V.K., Priyadarsini I. Metallomics, 2017, vol. 9, pp. 715–725. DOI: 10.1039/c7mt00034k.
Srisapoome P., Hamano K., Tsutsui I., Iiyama K. Fish & Shellfish Immunology, 2018, vol. 72, pp. 494–501. DOI: 10.1016/j.fsi.2017.11.037.
Gordts S.C., Férir G., D’huys T., Petrova M.I., Lebeer S., Snoeck R., Andrei G., Schols D. PLoS ONE, 2015, vol. 10 (7), article 0131219. DOI: 10.1371/journal.pone.0131219.
Lee J.B., Yamagishi C., Hayashi K., Hayashi T. Bioscience, Biotechnology and Biochemistry, 2011, vol. 75, pp. 459–465. DOI: 10.1271/bbb.100645.
Yang W., Fortunati E., Dominici F., Giovanale G., Mazzaglia A., Balestra G.M., Kenny J.M., Puglia D. European Pol-ymer Journal, 2016, vol. 79, pp. 1–12. DOI: 10.1016/j.eurpolymj.2016.04.003.
Cazacu G., Capraru M., Popa V. Advances in Natural Polymers. Springer Berlin Heidelberg, 2013, vol. 18, pp. 255–312.
Yang W., Fortunati E., Dominici F., Giovanale G., Mazzaglia A., Balestra G.M., Kenny J.M., Puglia D. International Journal of Biological Macromolecules, 2016, vol. 89, pp. 360–368. DOI: 10.1016/j.ijbiomac.2016.04.068.
Andrianova Ye.N. Ptitsevodstvo, 2017, no. 6, pp. 13–16. (in Russ.).
Klapiszewski L., Jesionowski T. Handbook of Composites from Renewable Materials, 2017, pp. 519–554. DOI: 10.1002/9781119441632.ch122.
Golovnya Ye. Zhivotnovodstvo Rossii, 2021, no. S3, pp. 38–39. (in Russ.).
Borisenkov M.F., Karmanov A.P., Kocheva L.S., Markov P.A., Istomina E.I., Bakutova L.A., Litvinets S.G., Martin-son E.A., Durnev E.A., Vityazev F.A., Popov S.V. International Journal of Polymeric Materials and Polymeric Bio-materials, 2016, vol. 65 (9), pp. 433–441. DOI: 10.1080/00914037.2015.1129955.
Solihat N., Sari F., Falah F., Ismayati M., Lubis M. Adly, Fatriasari W., Santoso E., Syafii W. Jurnal Sylva Lestari, 2021, vol. 9 (1), pp. 1–22. DOI: 10.23960/jsl191-22.
Xie D., Gan T., Su C., Han Y., Liu Z., Cao Y. International Journal of Biological Macromolecules, 2020, vol. 161, pp. 315–324. DOI: 10.1016/j.ijbiomac.2020.06.049.
Piccinino D., Capecchi E., Tomaino E., Gabellone S., Gigli V., Avitabile D., Saladino R. Antioxidants, 2021, vol. 10 (2), p. 274. DOI: 10.3390/antiox10020274.
Su C., Gan T., Liu Z., Chen Y., Zhou Q., Xia J., Cao Y. International Journal of Biological Macromolecules, 2021, vol. 184, pp. 369–379. DOI: 10.1016/j.ijbiomac.2021.06.063.
Hsu B., Coupar I.M., Ng K. Food Chemistry, 2006, vol. 98, pp. 317–328. DOI: 10.1016/j.foodchem.2005.05.077.
Dong X., Dong M., Lu Y., Turley A., Jin T., Wu C. Industrial Crops and Products, 2011, vol. 34, pp. 1629–1634. DOI: 10.1016/j.indcrop.2011.06.002.
Lapin A.A., Borisenkov M.F., Karmanov A.P., Berdnik I.V., Kocheva L.S., Musin R.Z., Magdeyev I.M. Khimiya Ras-titel’nogo Syr’ya, 2007, no. 2, pp. 79–83. (in Russ.).
Patent 2292896 (RU). 2007. (in Russ.).
Kocheva L.S., Karmanov A.P., Borisenkov M.F. Uspekhi gerontologii, 2008, vol. 21, no. 3, pp. 494–495. (in Russ.).
Kumar R., Butreddy A., Kommineni N., Reddy P.G., Bunekar N., Sarkar C., Dutt S., Mishra V.K., Aadil K.R., Mishra Y.K., Oupicky D., Kaushik A. International Journal of Nanomedicine, 2021, vol. 16, pp. 2419–2441. DOI: 10.2147/IJN.S303462.
Wardman P. The British Journal of Radiology, 2009, vol. 82, pp. 89–104. DOI: 10.1259/bjr/60186130.
Gudkov S.V., Popova N.R., Bruskov V.I. Biophysics, 2015, vol. 60 (4), pp. 659–667. DOI: 10.1134/S0006350915040120.
Hosseinimehr S.J. Drug Discovery Today, 2007, vol. 12, pp. 794–805. DOI: 10.1016/j.drudis.2007.07.017.
Panchenko A.V., Fedoros E.I., Pigarev S.E., Bykov V.N., Drachev I.S., Kraev S.Y. Radiatsionnaya biologiya. Radi-oekologiya, 2017, vol. 57 (5), pp. 1–7. DOI: 10.7868/S086980311705006X. (in Russ.).
Bykov V.N., Drachev I.S., Kraev S.Y., Maydin M.A., Gubareva E.A., Pigarev S.E., Anisimov V.N., Baldueva I.A., Fedoros E.I., Panchenko A.V. International Journal of Radiation Biology, 2018, vol. 94 (2), pp. 114–123. DOI: 10.1080/09553002.2018.1416204.
Bykov V.N., Drachev I.S., Panchenko A.V., Fedoros E.I., Pigarev S.E. Radiatsionnaya biologiya. Radioekologiya, 2020, vol. 60 (4), pp. 404–410. DOI: 10.31857/S0869803120040050. (in Russ.).
Kuntic V.S., Stankovic M.B., Vujic Z.B., Brboric J.S., Uskokovic-Markovic S.M. Chemistry and Biodiversity, 2013, vol. 10, pp. 1791–1803, DOI: 10.1002/cbdv.201300054.
Qazi S.S., Li D., Briens C., Berruti F., Abou-Zaid M. Molecules, 2017, vol. 22 (3), article 372. DOI: 10.3390/molecules22030372.
Pigarev S.E., Trashkov A.P., Panchenko A.V., Yurova M.N., Bykov V.N., Fedoros E.I., Anisimov V.N. Environmen-tal Research, 2021, vol. 192, article 110321. DOI: 10.1016/j.envres.2020.110321.
Azqueta A., Collins A. Nutrients, 2016, vol. 8, article 785. DOI: 10.3390/nu8120785.
Labaj J., Slamenova D., Kosikova B. Nutrition and Cancer, 2003, vol. 47, pp. 95–103. DOI: 10.1207/s15327914nc4701_12.
Wang Y., Duan H., Dai Y., Bin P., Cheng J., Pan Z., Huang C., Leng S., Zheng Y. Science of the Total Environment, 2009, vol. 407, pp. 2615–2620. DOI: 10.1016/j.scitotenv.2009.01.002.
Assimopoulou A.N., Sinakos Z., Papageorgiou V.P. Phytotherapy Research, 2005, vol. 19, pp. 997–1000. DOI: 10.1002/ptr.1749.
Papież M.A. Drug and Chemical Toxicology, 2013, vol. 36 (1), pp. 93–101. DOI: 10.3109/01480545.2012.726626.
Kuhlmann M.K., Horsch E., Burkhardt G., Wagner M., Köhler H. Archives of Toxicology, 1998, vol. 72 (8), pp. 536–540. DOI: 10.1007/s002040050539.
Barsberg S., Elder T., Felby C. Chemistry of Materials, 2003, vol. 15, pp. 649–655. DOI: 10.1021/cm021162s.
Su X., Fu Y., Shao Z., Qin M., Li X., Zhang F. Industrial Crops and Products, 2022, vol. 176, article 114359.
Bykov V.N. Uspekhi gerontologii, 2020, vol. 33 (4), pp. 646–656. DOI: 10.34922/AE.2020.33.4.003. (in Russ.).
Belyy V.A., Pechnikova A.A., Kocheva L.S., Moskalov A.A., Karmanov A.P. Uspekhi gerontologii, 2010, vol. 23 (2), pp. 221–227. (in Russ.).
Moskalev A., Chernyagina E., de Magalhaes J.P., Barardo D., Thoppil H., Shaposhnikov M., Budovsky A., Fraifeld V.E., Garazha A., Tsvetkov V., Bronovitsky E., Bogomolov V., Scerbacov A., Kuryan O., Gurinovich R., Jellen L. C., Kennedy B., Mamoshina P., Dobrovolskaya E., Aliper A., Kaminsky D., Zhavoronkov A. Aging, 2015, vol. 7, pp. 616–628. DOI: 10.18632/aging.100799.
Fedoros E.I., Badun G.A., Grozdova I.D., Melik-Nubarov N.S., Perminova I.V., Baldueva I.A., Danilova A.B., Nehaeva T.L., Ryakhovskiy A.A., Pigarev S.E., Panchenko A.V., Anisimov, V.N. Fifth International Conference of CIS IHSS on Humic Innovative Technologies «Humic Substances and Living Systems» (HIT-2019), Moscow, 2019, p. 101. DOI: 10.36291/HIT.2019.fedoros.089.
Copyright (c) 2023 chemistry of plant raw material
This work is licensed under a Creative Commons Attribution 4.0 International License.
This work is licensed under a Creative Commons Attribution 4.0 International License.
The authors, which are published in this journal, agree to the following conditions:
1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .
2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.
3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.