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<article article-type="research-article" dtd-version="1.3" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xml:lang="ru"><front><journal-meta><journal-id journal-id-type="publisher-id">medlit</journal-id><journal-title-group><journal-title xml:lang="ru">Гигиена и санитария</journal-title><trans-title-group xml:lang="en"><trans-title>Hygiene and Sanitation</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">0016-9900</issn><issn pub-type="epub">2412-0650</issn><publisher><publisher-name>Federal Scientific Center of Hygiene named after F.F. Erisman</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.47470/0016-9900-2020-99-12-1365-1369</article-id><article-id custom-type="elpub" pub-id-type="custom">medlit-1134</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>ГИГИЕНА ОКРУЖАЮЩЕЙ СРЕДЫ</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="en"><subject>ENVIRONMENTAL HYGIENE</subject></subj-group></article-categories><title-group><article-title>Комплексообразующая способность органических соединений и их влияние на организм человека (обзор)</article-title><trans-title-group xml:lang="en"><trans-title>Complexing ability of organic compounds and their influence on the human body (review)</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-4632-6060</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Хлыстов</surname><given-names>Иван Андреевич</given-names></name><name name-style="western" xml:lang="en"><surname>Hlystov</surname><given-names>Ivan A.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Канд. биол. наук, науч. сотр., ФБУН ЕМНЦ ПОЗРПП Роспотребнадзора, 620014, Екатеринбург.</p><p>e-mail: hlistovia@ymrc.ru</p></bio><bio xml:lang="en"><p>Researcher (Non-Academic) - Yekaterinburg Medical Research Center for Prophylaxis and Health Protection in Industrial Workers, Yekaterinburg, 620014, Russian Federation.</p><p>e-mail: hlistovia@ymrc.ru</p></bio><email xlink:type="simple">hlistovia@ymrc.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-8846-8016</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Штин</surname><given-names>Т. Н.</given-names></name><name name-style="western" xml:lang="en"><surname>Shtin</surname><given-names>Tat’yana N.</given-names></name></name-alternatives><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-6475-7753</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Гурвич</surname><given-names>В. Б.</given-names></name><name name-style="western" xml:lang="en"><surname>Gurvich</surname><given-names>Vladimir B.</given-names></name></name-alternatives><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-0723-8674</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Кузьмина</surname><given-names>Е. А.</given-names></name><name name-style="western" xml:lang="en"><surname>Kuz´mina</surname><given-names>Elena A.</given-names></name></name-alternatives><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-2"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0002-6562-2842</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Бугаева</surname><given-names>А. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Bugayeva</surname><given-names>Aleksandra V.</given-names></name></name-alternatives><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0001-7927-0246</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Харькова</surname><given-names>П. К.</given-names></name><name name-style="western" xml:lang="en"><surname>Khar´kova</surname><given-names>Polina K.</given-names></name></name-alternatives><email xlink:type="simple">noemail@neicon.ru</email><xref ref-type="aff" rid="aff-1"/></contrib></contrib-group><aff-alternatives id="aff-1"><aff xml:lang="ru"><institution>ФБУН «Екатеринбургский медицинский - научный центр профилактики и охраны здоровья рабочих промпредприятий» Роспотребнадзора</institution></aff><aff xml:lang="en"><institution>Yekaterinburg Medical Research Center for Prophylaxis and Health Protection in Industrial Workers</institution></aff></aff-alternatives><aff-alternatives id="aff-2"><aff xml:lang="ru"><institution>ФБУЗ «Федеральный центр гигиены и эпидемиологии» Роспотребнадзора</institution></aff><aff xml:lang="en"><institution>Center for Hygiene and Epidemiology</institution></aff></aff-alternatives><pub-date pub-type="collection"><year>2020</year></pub-date><pub-date pub-type="epub"><day>20</day><month>01</month><year>2021</year></pub-date><volume>99</volume><issue>12</issue><fpage>1365</fpage><lpage>1369</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Хлыстов И.А., Штин Т.Н., Гурвич В.Б., Кузьмина Е.А., Бугаева А.В., Харькова П.К., 2021</copyright-statement><copyright-year>2021</copyright-year><copyright-holder xml:lang="ru">Хлыстов И.А., Штин Т.Н., Гурвич В.Б., Кузьмина Е.А., Бугаева А.В., Харькова П.К.</copyright-holder><copyright-holder xml:lang="en">Hlystov I.A., Shtin T.N., Gurvich V.B., Kuz´mina E.A., Bugayeva A.V., Khar´kova P.K.</copyright-holder><license xml:lang="ru" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>Данная работа распространяется под лицензией Creative Commons Attribution 4.0.</license-p></license><license xml:lang="en" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>This work is licensed under a Creative Commons Attribution 4.0 License.</license-p></license></permissions><self-uri xlink:href="https://www.rjhas.ru/jour/article/view/1134">https://www.rjhas.ru/jour/article/view/1134</self-uri><abstract><p>Введение. Существует острая проблема увеличения содержания органических веществ в природных водах, расширения перечня поступающих веществ в водоёмы в связи с промышленной, хозяйственной деятельностью человека, изменениями климата. В этих условиях вероятно появление соединений с неизученными химическими и токсическими свойствами.</p><p>Цель работы – на основании имеющихся литературных данных собрать сведения о путях поступления органических соединений в водоёмы и организм человека, изучить данные о механизмах взаимодействия органических веществ с металлами, показать судьбу известных органических хелаторов, комплексообразователей и сформированных ими металлоорганических соединений внутри организма. Поиск литературы осуществлён по базам данных Scopus, Web of Science, CyberLeninka.</p><p>Источники поступления органических веществ в водоёмы, свойства органических веществ. Выделяют три группы органических веществ в водоёмах, разделяемых по источникам их появления (поступления): терригенного происхождения, образующиеся внутри водоёмов и поступающие из техногенных источников. Органические соединения способны образовывать растворимые и нерастворимые соединения с металлами и коллоидами.</p><p>Механизмы взаимодействия органических веществ с металлами. Образование связей органических веществ происходит по типу хелатирования и комплексообразования, зависит от наличия функциональных групп, молекулярной массы веществ, радиуса ионов, конкурирующих взаимодействий с сайтами связывания. К веществам, проявляющим связывающие свойства, относят фенольные соединения, карбоновые кислоты, полисахариды, флавоноиды. В связи с тем, что фенольные соединения в больших количествах содержатся в растительной и животной ткани, данная группа соединений с позиции взаимодействий с металлами и токсикометрии изучена более подробно.</p><p>Поступление органических и органометаллических соединений в организм, их кинетика, метаболизм и распад. Органические соединения, хелаты и комплексы поступают в организм с питьевой водой, продуктами и лекарствами, а также образуются в организме, в том числе путём замещения ионов. Представлена информация по биохимическим и токсикологическим исследованиям известных на сегодняшний день соединений.</p></abstract><trans-abstract xml:lang="en"><p>Introduction. Increased content of organic substances in natural waters, expanding the list of input substances to water bodies, owing to industrial and economic activities of a person, and climate changes is an urgent issue. Against this background, compounds with unknown chemical and toxic properties are likely to appear. </p><p>The purpose of this study is to collect data concerning the ways for organic compounds entering water bodies and the human body, study data on interaction mechanisms of organic substances with metals, reveal the fate of known organic chelators, complexing agents as well as organometallic compound shaped by them inside the body. The literature search was carried out in Scopus, Web of Science, CyberLeninka databases.</p><p>Sources of organic substances entering water bodies, properties of organic substances. There are three types of organic substances in water bodies, divided by the sources of their occurrence (inflow): terrigenous origin, shaped inside water bodies and coming from man-made sources. Organic compounds may produce soluble and insoluble compounds with metals and colloids.</p><p>Mechanisms of interaction of organic substances with metals. Bonding of organic substances takes place by the type of chelation and complexation. There are factors for bonding: functional group content, the molecular mass of substances, ion radius, and competitive interaction with binding sites. Substances having binding properties include phenolic compounds, carboxylic acids, polysaccharides, and flavonoids. Considering that phenolic compounds are located in large quantities in plant and animal tissues, this group of compounds has been researched more thoroughly in terms of interactions with metals and toxicometry.</p><p>Intake of organic and organometallic compounds into the body, their kinetics, metabolism and decay. Organic compounds, chelates, and complexes enter the body with drinking water, food, and drugs. They are also generated in the body, including by replacing ions. Data on biochemical and toxicological studies of currently known compounds is given.</p></trans-abstract><kwd-group xml:lang="ru"><kwd>органические соединения</kwd><kwd>металлы</kwd><kwd>комплексообразование и хелатирование</kwd><kwd>водоёмы</kwd><kwd>риски для здоровья</kwd><kwd>токсичность</kwd><kwd>обзор</kwd></kwd-group><kwd-group xml:lang="en"><kwd>organic compounds</kwd><kwd>metals</kwd><kwd>complexation and chelation</kwd><kwd>water bodies</kwd><kwd>health risks</kwd><kwd>toxicity</kwd><kwd>review</kwd></kwd-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">Egorova K.S., Ananikov V.P. Toxicity of metal compounds: knowledge and myths. Organometallics. 2017; 36(21): 4071-90. https://doi.org/10.1021/acs.organomet.7b00605</mixed-citation><mixed-citation xml:lang="en">Egorova K.S., Ananikov V.P. Toxicity of metal compounds: knowledge and myths. Organometallics. 2017; 36(21): 4071–90. https://doi.org/10.1021/acs.organomet.7b00605</mixed-citation></citation-alternatives></ref><ref id="cit2"><label>2</label><citation-alternatives><mixed-citation xml:lang="ru">Kovacs M.H., Kovacs E.D. Concerning Organometallic Compounds in Environment: Occurrence, Fate, and Impact. In: Rahman M., Asiri A.M., eds. Recent Progress in Organometallic Chemistry. 2017. https://doi.org/10.5772/67755 Available at: https://www.intechopen.com/books/recent-progress-in-organometallic-chemistry/concerning-organometallic-compounds-in-environment-occurrence-fate-and-impact</mixed-citation><mixed-citation xml:lang="en">Kovacs M.H., Kovacs E.D. Concerning Organometallic Compounds in Environment: Occurrence, Fate, and Impact. In: Rahman M., Asiri A.M., eds. Recent Progress in Organometallic Chemistry. 2017. https://doi.org/10.5772/67755 Available at: https://www.intechopen.com/books/recent-progress-in-organometallic-chemistry/concerning-organometallic-compounds-in-environment-occurrence-fate-and-impact</mixed-citation></citation-alternatives></ref><ref id="cit3"><label>3</label><citation-alternatives><mixed-citation xml:lang="ru">Lee R., Oshima Y. Effects of selected pesticides, metals and organometallics on development of blue crab (Callinectes sapidus) embryos. Mar. Environ. Res. 1998; 46(1-5): 479-82. https://doi.org/10.1016/S0141-1136(97)00072-X</mixed-citation><mixed-citation xml:lang="en">Lee R., Oshima Y. Effects of selected pesticides, metals and organometallics on development of blue crab (Callinectes sapidus) embryos. Mar. Environ. Res. 1998; 46(1–5): 479–82. https://doi.org/10.1016/S0141-1136(97)00072-X</mixed-citation></citation-alternatives></ref><ref id="cit4"><label>4</label><citation-alternatives><mixed-citation xml:lang="ru">Cole R.F., Mills G.A., Parker R., Bolam T., Birchenough A., Kröger S., et al. Trends in the analysis and monitoring of organotins in the aquatic environment. Trends Environ. Anal. Chem. 2015; (8): 1-11. https://doi.org/10.1016/j.teac.2015.05.001</mixed-citation><mixed-citation xml:lang="en">Cole R.F., Mills G.A., Parker R., Bolam T., Birchenough A., Kröger S., et al. Trends in the analysis and monitoring of organotins in the aquatic environment. Trends Environ. Anal. Chem. 2015; (8): 1–11. https://doi.org/10.1016/j.teac.2015.05.001</mixed-citation></citation-alternatives></ref><ref id="cit5"><label>5</label><citation-alternatives><mixed-citation xml:lang="ru">Nierenberg D.W., Nordgren R.E., Chang M.B., Siegler R.W., Blayney M.B., Hochberg F., et al. Delayed cerebellar disease and death after accidental exposure to dimethylmercury. N. Eng. J. Med. 1998; 338(23): 1672-6. https://doi.org/10.1056/nejm199806043382305</mixed-citation><mixed-citation xml:lang="en">Nierenberg D.W., Nordgren R.E., Chang M.B., Siegler R.W., Blayney M.B., Hochberg F., et al. Delayed cerebellar disease and death after accidental exposure to dimethylmercury. N. Eng. J. Med. 1998; 338(23): 1672–6. https://doi.org/10.1056/nejm199806043382305</mixed-citation></citation-alternatives></ref><ref id="cit6"><label>6</label><citation-alternatives><mixed-citation xml:lang="ru">Lozovik P.A., Morozov A.K., Zobkov M.B., Dukhovicheva T.A., Osipova L.A. Allochthonous and autochthonous organic matter in surface waters in Karelia. Water Res. 2007; 34(2): 204-16.</mixed-citation><mixed-citation xml:lang="en">Lozovik P.A., Morozov A.K., Zobkov M.B., Dukhovicheva T.A., Osipova L.A. Allochthonous and autochthonous organic matter in surface waters in Karelia. Water Res. 2007; 34(2): 204–16.</mixed-citation></citation-alternatives></ref><ref id="cit7"><label>7</label><citation-alternatives><mixed-citation xml:lang="ru">Mostofa K.M.G., Liu C.Q., Mottaleb M.A., Wan G., Ogawa H., Vione D., et al. Dissolved Organic Matter in Natural Waters. Photobiogeochemistry of Organic Matter. Principles and Practices in Water Environments. New York, Dordrecht, London; 2013.</mixed-citation><mixed-citation xml:lang="en">Mostofa K.M.G., Liu C.Q., Mottaleb M.A., Wan G., Ogawa H., Vione D., et al. Dissolved Organic Matter in Natural Waters. Photobiogeochemistry of Organic Matter. Principles and Practices in Water Environments. New York, Dordrecht, London; 2013.</mixed-citation></citation-alternatives></ref><ref id="cit8"><label>8</label><citation-alternatives><mixed-citation xml:lang="ru">Park H.K., Byeon M.S., Shin Y.N., Jung D.I. Sources and spatial and temporal characteristics of organic carbon in two large reservoirs with contrasting hydrologic characteristics. Water Resour. Res. 2009; 45(11): W11418. https://doi.org/10.1029/2009WR008043</mixed-citation><mixed-citation xml:lang="en">Park H.K., Byeon M.S., Shin Y.N., Jung D.I. Sources and spatial and temporal characteristics of organic carbon in two large reservoirs with contrasting hydrologic characteristics. Water Resour. Res. 2009; 45(11): W11418. https://doi.org/10.1029/2009WR008043</mixed-citation></citation-alternatives></ref><ref id="cit9"><label>9</label><citation-alternatives><mixed-citation xml:lang="ru">Toming K., Tuvikene L., Vilbaste S., Agasild H., Viik M., Kisand A., et al. Contributions of autochthonous and allochthonous sources to dissolved organic matter in a large, shallow, eutrophic lake with a highly calcareous catchment. Limnol. Oceanogr. 2013; 58(4): 1259-70. https://doi.org/10.4319/lo.2013.58.4.1259</mixed-citation><mixed-citation xml:lang="en">Toming K., Tuvikene L., Vilbaste S., Agasild H., Viik M., Kisand A., et al. Contributions of autochthonous and allochthonous sources to dissolved organic matter in a large, shallow, eutrophic lake with a highly calcareous catchment. Limnol. Oceanogr. 2013; 58(4): 1259–70. https://doi.org/10.4319/lo.2013.58.4.1259</mixed-citation></citation-alternatives></ref><ref id="cit10"><label>10</label><citation-alternatives><mixed-citation xml:lang="ru">Al-Reasi H.A., Wood C.M., Smith D.S. Characterization of freshwater natural dissolved organic matter (DOM): Mechanistic explanations for protective effects against metal toxicity and direct effects on organisms. Environ. Int. 2013; 59: 201-7. https://doi.org/10.1016/j.envint.2013.06.005</mixed-citation><mixed-citation xml:lang="en">Al-Reasi H.A., Wood C.M., Smith D.S. Characterization of freshwater natural dissolved organic matter (DOM): Mechanistic explanations for protective effects against metal toxicity and direct effects on organisms. Environ. Int. 2013; 59: 201–7. https://doi.org/10.1016/j.envint.2013.06.005</mixed-citation></citation-alternatives></ref><ref id="cit11"><label>11</label><citation-alternatives><mixed-citation xml:lang="ru">Findley W.G. Aquatic Ecosystems: Interactivity of Dissolved Organic Matter (Aquatic Ecology). San Diego: Academic Press; 2003.</mixed-citation><mixed-citation xml:lang="en">Findley W.G. Aquatic Ecosystems: Interactivity of Dissolved Organic Matter (Aquatic Ecology). San Diego: Academic Press; 2003.</mixed-citation></citation-alternatives></ref><ref id="cit12"><label>12</label><citation-alternatives><mixed-citation xml:lang="ru">Hossain M.M., Islam K.M.N., Rahman I.M.M. An Overview of the Persistent Organic Pollutants in the Freshwater System. Ecological Water Quality - Water Treatment and Reuse. Rijeka, Croatia; 2012: 455-70.</mixed-citation><mixed-citation xml:lang="en">Hossain M.M., Islam K.M.N., Rahman I.M.M. An Overview of the Persistent Organic Pollutants in the Freshwater System. Ecological Water Quality – Water Treatment and Reuse. Rijeka, Croatia; 2012: 455–70.</mixed-citation></citation-alternatives></ref><ref id="cit13"><label>13</label><citation-alternatives><mixed-citation xml:lang="ru">Mostofa K.M., Yoshioka T., Mottaleb A., Vione D., eds. Photobiogeochemistry of Organic Matter: Principles and Practices in Water Environments. New York, Dordrecht, London; 2013.</mixed-citation><mixed-citation xml:lang="en">Mostofa K.M., Yoshioka T., Mottaleb A., Vione D., eds. Photobiogeochemistry of Organic Matter: Principles and Practices in Water Environments. New York, Dordrecht, London; 2013.</mixed-citation></citation-alternatives></ref><ref id="cit14"><label>14</label><citation-alternatives><mixed-citation xml:lang="ru">Ashworth D.J., Alloway B.J. Influence of dissolved organic matter on the solubility of heavy metals in sewage-sludge-amended soils. Commun. Soil Sci. Plant Anal. 2008; 39: 538-50. https://doi.org/10.1080/00103620701826787</mixed-citation><mixed-citation xml:lang="en">Ashworth D.J., Alloway B.J. Influence of dissolved organic matter on the solubility of heavy metals in sewage-sludge-amended soils. Commun. Soil Sci. Plant Anal. 2008; 39: 538–50. https://doi.org/10.1080/00103620701826787</mixed-citation></citation-alternatives></ref><ref id="cit15"><label>15</label><citation-alternatives><mixed-citation xml:lang="ru">Cory R.M., Green S.A., Pregitzer K.S. Dissolved Organic Matter concentration and composition in the forests and streams of Olympic National Park, WA. Biogeochemistry. 2004; 67: 269-88.</mixed-citation><mixed-citation xml:lang="en">Cory R.M., Green S.A., Pregitzer K.S. Dissolved Organic Matter concentration and composition in the forests and streams of Olympic National Park, WA. Biogeochemistry. 2004; 67: 269–88.</mixed-citation></citation-alternatives></ref><ref id="cit16"><label>16</label><citation-alternatives><mixed-citation xml:lang="ru">Kalbitz K., Wennrich R. Mobilization of heavy metals and arsenic in polluted wetland soils and its dependence on dissolved organic matter. Sci. Total Environ. 1998; 209(1): 27-39. https://doi.org/10.1016/s0048-9697(97)00302-1</mixed-citation><mixed-citation xml:lang="en">Kalbitz K., Wennrich R. Mobilization of heavy metals and arsenic in polluted wetland soils and its dependence on dissolved organic matter. Sci. Total Environ. 1998; 209(1): 27–39. https://doi.org/10.1016/s0048-9697(97)00302-1</mixed-citation></citation-alternatives></ref><ref id="cit17"><label>17</label><citation-alternatives><mixed-citation xml:lang="ru">Paunovic I., Schulin R., Nowack B. Fractionation of dissolved organic carbon from soil solution with immobilized metal ion affinity chromatography. Eur. J. Soil Sci. 2008; 59(2): 198-207. https://doi.org/10.1111/j.1365-2389.2007.00975.x</mixed-citation><mixed-citation xml:lang="en">Paunovic I., Schulin R., Nowack B. Fractionation of dissolved organic carbon from soil solution with immobilized metal ion affinity chromatography. Eur. J. Soil Sci. 2008; 59(2): 198–207. https://doi.org/10.1111/j.1365-2389.2007.00975.x</mixed-citation></citation-alternatives></ref><ref id="cit18"><label>18</label><citation-alternatives><mixed-citation xml:lang="ru">Boguta P., Sokołowska Z. Interactions of humic acids with metals. Acta Agroph. Monograph. 2013; (2).</mixed-citation><mixed-citation xml:lang="en">Boguta P., Sokołowska Z. Interactions of humic acids with metals. Acta Agroph. Monograph. 2013; (2).</mixed-citation></citation-alternatives></ref><ref id="cit19"><label>19</label><citation-alternatives><mixed-citation xml:lang="ru">Libecki B., Dziejowski J. Changes in iron(II) and iron(III) content in a solution of humic acids during coagulation by means of monomeric iron(III) salts. Polish J. Environ. Study. 2010; 19(5): 1089-93.</mixed-citation><mixed-citation xml:lang="en">Libecki B., Dziejowski J. Changes in iron(II) and iron(III) content in a solution of humic acids during coagulation by means of monomeric iron(III) salts. Polish J. Environ. Study. 2010; 19(5): 1089–93.</mixed-citation></citation-alternatives></ref><ref id="cit20"><label>20</label><citation-alternatives><mixed-citation xml:lang="ru">Riedhammer C., Schwarz-Schulz B. The newly proposed EU risk assessment concept for the sediment compartment. J. Soils Sediments. 2001; 1(2): 105-10. https://doi.org/10.1007/BF02987715</mixed-citation><mixed-citation xml:lang="en">Riedhammer C., Schwarz-Schulz B. The newly proposed EU risk assessment concept for the sediment compartment. J. Soils Sediments. 2001; 1(2): 105–10. https://doi.org/10.1007/BF02987715</mixed-citation></citation-alternatives></ref><ref id="cit21"><label>21</label><citation-alternatives><mixed-citation xml:lang="ru">Aiken G.R., Hsu-Kim H., Ryan J.N. Influence of dissolved organic matter on the environmental fate of metals, nanoparticles, and colloids. Environ. Sci. Technol. 2011; 45(8): 3196-201. https://doi.org/10.1021/es103992s</mixed-citation><mixed-citation xml:lang="en">Aiken G.R., Hsu-Kim H., Ryan J.N. Influence of dissolved organic matter on the environmental fate of metals, nanoparticles, and colloids. Environ. Sci. Technol. 2011; 45(8): 3196–201. https://doi.org/10.1021/es103992s</mixed-citation></citation-alternatives></ref><ref id="cit22"><label>22</label><citation-alternatives><mixed-citation xml:lang="ru">Zhang Z., Shi W., Ma H., Zhou B., Li H., Lü C., et al. Binding mechanism between fulvic acid and heavy metals: integrated interpretation of binding experiments, fraction characterizations, and models. Water Air Soil Pollut. 2020; 231(284). https://doi.org/10.1007/s11270-020-04558-2</mixed-citation><mixed-citation xml:lang="en">Zhang Z., Shi W., Ma H., Zhou B., Li H., Lü C., et al. Binding mechanism between fulvic acid and heavy metals: integrated interpretation of binding experiments, fraction characterizations, and models. Water Air Soil Pollut. 2020; 231(284). https://doi.org/10.1007/s11270-020-04558-2</mixed-citation></citation-alternatives></ref><ref id="cit23"><label>23</label><citation-alternatives><mixed-citation xml:lang="ru">Ghosh R., Banerjee D.K. Complexation of trace metals with humic acids from soil, sediment and sewage. Chem. Speciat. Bioavailab. 1997; 9(1): 15-9. https://doi.org/10.1080/09542299.1997.11083279</mixed-citation><mixed-citation xml:lang="en">Ghosh R., Banerjee D.K. Complexation of trace metals with humic acids from soil, sediment and sewage. Chem. Speciat. Bioavailab. 1997; 9(1): 15–9. https://doi.org/10.1080/09542299.1997.11083279</mixed-citation></citation-alternatives></ref><ref id="cit24"><label>24</label><citation-alternatives><mixed-citation xml:lang="ru">Helal A.A., Imam D.M., Khalifa S.M., Aly H.F. Interaction of pesticides with humic compounds and their metal complexes. Radiochemistry. 2006; 48(4): 419-25. https://doi.org/10.1134/S1066362206040199</mixed-citation><mixed-citation xml:lang="en">Helal A.A., Imam D.M., Khalifa S.M., Aly H.F. Interaction of pesticides with humic compounds and their metal complexes. Radiochemistry. 2006; 48(4): 419–25. https://doi.org/10.1134/S1066362206040199</mixed-citation></citation-alternatives></ref><ref id="cit25"><label>25</label><citation-alternatives><mixed-citation xml:lang="ru">Huang G., Wang D., Ma S., Chen J., Jiang L., Wang P. A new, low-cost adsorbent: Preparation, characterization, and adsorption behavior of Pb(II) and Cu(II). J. Colloid Interface Sci. 2015; 445: 294-302. https://doi.org/10.1016/j.jcis.2014.12.099</mixed-citation><mixed-citation xml:lang="en">Huang G., Wang D., Ma S., Chen J., Jiang L., Wang P. A new, low-cost adsorbent: Preparation, characterization, and adsorption behavior of Pb(II) and Cu(II). J. Colloid Interface Sci. 2015; 445: 294–302. https://doi.org/10.1016/j.jcis.2014.12.099</mixed-citation></citation-alternatives></ref><ref id="cit26"><label>26</label><citation-alternatives><mixed-citation xml:lang="ru">von Wandruszka A., Ragle C., Engebretson R. The role of selected cations in the formation of pseudomicelles in aqueous humic acid. Talanta. 1997; 44(5): 805-9. https://doi.org/10.1016/s0039-9140(96)02116-9</mixed-citation><mixed-citation xml:lang="en">von Wandruszka A., Ragle C., Engebretson R. The role of selected cations in the formation of pseudomicelles in aqueous humic acid. Talanta. 1997; 44(5): 805–9. https://doi.org/10.1016/s0039-9140(96)02116-9</mixed-citation></citation-alternatives></ref><ref id="cit27"><label>27</label><citation-alternatives><mixed-citation xml:lang="ru">Boggs S.J., Livermore D., Seitz M.G. Humic Substances in Natural Waters and Their Complexation with Trace Metals and Radionuclides: a Review. Lemont, IL: Argonne National Lab; 1985.</mixed-citation><mixed-citation xml:lang="en">Boggs S.J., Livermore D., Seitz M.G. Humic Substances in Natural Waters and Their Complexation with Trace Metals and Radionuclides: a Review. Lemont, IL: Argonne National Lab; 1985.</mixed-citation></citation-alternatives></ref><ref id="cit28"><label>28</label><citation-alternatives><mixed-citation xml:lang="ru">Попов А.И. Гуминовые вещества: свойства, строение, образование. СПб.; 2004</mixed-citation><mixed-citation xml:lang="en">Popov A.I. Humic Substances: Properties, Structure, Formation [Guminovye veshchestva: svoystva, stroenie, obrazovanie]. St. Petersburg; 2004. (in Russian)</mixed-citation></citation-alternatives></ref><ref id="cit29"><label>29</label><citation-alternatives><mixed-citation xml:lang="ru">Malá J., Cvikrová M., Hrubcová M., Máchová P. Influence of vegetation on phenolic acid contents in soil. J. Forest Sci. 2013; 59(7): 288-94.</mixed-citation><mixed-citation xml:lang="en">Malá J., Cvikrová M., Hrubcová M., Máchová P. Influence of vegetation on phenolic acid contents in soil. J. Forest Sci. 2013; 59(7): 288–94.</mixed-citation></citation-alternatives></ref><ref id="cit30"><label>30</label><citation-alternatives><mixed-citation xml:lang="ru">Rimmer D.L., Abbott G.D. Phenolic Compounds in NaOH Extracts of UK Soils and Their Contribution to Antioxidant Capacity. Brisbane, Australia; 2010: 167-70.</mixed-citation><mixed-citation xml:lang="en">Rimmer D.L., Abbott G.D. Phenolic Compounds in NaOH Extracts of UK Soils and Their Contribution to Antioxidant Capacity. Brisbane, Australia; 2010: 167–70.</mixed-citation></citation-alternatives></ref><ref id="cit31"><label>31</label><citation-alternatives><mixed-citation xml:lang="ru">Banach-Szott M. Content of phenolic compounds in humus acids of forest soil. Polish J. Soil Sci. 2007; 40(1): 68-79.</mixed-citation><mixed-citation xml:lang="en">Banach-Szott M. Content of phenolic compounds in humus acids of forest soil. Polish J. Soil Sci. 2007; 40(1): 68–79.</mixed-citation></citation-alternatives></ref><ref id="cit32"><label>32</label><citation-alternatives><mixed-citation xml:lang="ru">Kassim G., Stott D.E., Martin J.P., Haider K. Stabilization and incorporation into biomass of phenolic and benzenoid carbons during biodegradation in soil. Soil Sci. Soc. Am. J. 1982; 46(2): 305-9. https://doi.org/10.2136/sssaj1982.03615995004600020018x</mixed-citation><mixed-citation xml:lang="en">Kassim G., Stott D.E., Martin J.P., Haider K. Stabilization and incorporation into biomass of phenolic and benzenoid carbons during biodegradation in soil. Soil Sci. Soc. Am. J. 1982; 46(2): 305–9. https://doi.org/10.2136/sssaj1982.03615995004600020018x</mixed-citation></citation-alternatives></ref><ref id="cit33"><label>33</label><citation-alternatives><mixed-citation xml:lang="ru">Hernes P.J., Hedges J.I. Determination of condensed tannin monomers in environmental samples by capillary gas chromatography of acid depolymerization extracts. Anal. Chem. 2000; 72(20): 5115-24. https://doi.org/10.1021/ac991301y</mixed-citation><mixed-citation xml:lang="en">Hernes P.J., Hedges J.I. Determination of condensed tannin monomers in environmental samples by capillary gas chromatography of acid depolymerization extracts. Anal. Chem. 2000; 72(20): 5115–24. https://doi.org/10.1021/ac991301y</mixed-citation></citation-alternatives></ref><ref id="cit34"><label>34</label><citation-alternatives><mixed-citation xml:lang="ru">Kakkar S., Bais S. A review on protocatechuic acid and its pharmacological potential. ISRN Pharmacol. 2014; 2014: 952943. https://doi.org/10.1155/2014/952943</mixed-citation><mixed-citation xml:lang="en">Kakkar S., Bais S. A review on protocatechuic acid and its pharmacological potential. ISRN Pharmacol. 2014; 2014: 952943. https://doi.org/10.1155/2014/952943</mixed-citation></citation-alternatives></ref><ref id="cit35"><label>35</label><citation-alternatives><mixed-citation xml:lang="ru">Singh K., Kumar A. Kinetics of complex formation of Fe(III) with syringic acid: Experimental and theoretical study. Food Chem. 2018; 265: 96-100. https://doi.org/10.1016/j.foodchem.2018.05.071</mixed-citation><mixed-citation xml:lang="en">Singh K., Kumar A. Kinetics of complex formation of Fe(III) with syringic acid: Experimental and theoretical study. Food Chem. 2018; 265: 96–100. https://doi.org/10.1016/j.foodchem.2018.05.071</mixed-citation></citation-alternatives></ref><ref id="cit36"><label>36</label><citation-alternatives><mixed-citation xml:lang="ru">Khvan A.M., Kristallovich E.L., Abduazimov K.A. Complexation of caffeic and ferulic acids by transition-metal ions. Chem. Nat. Compd. 2001; 37(1): 72-5. https://doi.org/10.1023/A:1017662812611</mixed-citation><mixed-citation xml:lang="en">Khvan A.M., Kristallovich E.L., Abduazimov K.A. Complexation of caffeic and ferulic acids by transition-metal ions. Chem. Nat. Compd. 2001; 37(1): 72–5. https://doi.org/10.1023/A:1017662812611</mixed-citation></citation-alternatives></ref><ref id="cit37"><label>37</label><citation-alternatives><mixed-citation xml:lang="ru">Schweigert N., Zehnder A.J.B., Eggen R.I.L. Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Environ. Microbiol. 2001; 3(2): 81-91. https://doi.org/10.1046/j.1462-2920.2001.00176.x</mixed-citation><mixed-citation xml:lang="en">Schweigert N., Zehnder A.J.B., Eggen R.I.L. Chemical properties of catechols and their molecular modes of toxic action in cells, from microorganisms to mammals. Environ. Microbiol. 2001; 3(2): 81–91. https://doi.org/10.1046/j.1462-2920.2001.00176.x</mixed-citation></citation-alternatives></ref><ref id="cit38"><label>38</label><citation-alternatives><mixed-citation xml:lang="ru">Лазарев А.И. Органические реактивы в анализе металлов. М.: Металлургия; 1980</mixed-citation><mixed-citation xml:lang="en">Lazarev A.I. Organic Reagents in Metal Analysis [Organicheskie reaktivy v analize metallov]. Moscow: Metallurgiya; 1980. (in Russian)</mixed-citation></citation-alternatives></ref><ref id="cit39"><label>39</label><citation-alternatives><mixed-citation xml:lang="ru">Soldevila-Barreda J.J., Sadler P.J. Approaches to the design of catalytic metallodrugs. Curr. Opin. Chem. Biol. 2015; 25: 172-83. https://doi.org/10.1016/j.cbpa.2015.01.024</mixed-citation><mixed-citation xml:lang="en">Soldevila-Barreda J.J., Sadler P.J. Approaches to the design of catalytic metallodrugs. Curr. Opin. Chem. Biol. 2015; 25: 172–83. https://doi.org/10.1016/j.cbpa.2015.01.024</mixed-citation></citation-alternatives></ref><ref id="cit40"><label>40</label><citation-alternatives><mixed-citation xml:lang="ru">Keller S., Ong Y.C., Lin Y., Cariou K., Gasser G. A tutorial for the assessment of the stability of organometallic complexes in biological media. J. Organomet. Chem. 2019; 906: 121059. https://doi.org/10.1016/j.jorganchem.2019.121059</mixed-citation><mixed-citation xml:lang="en">Keller S., Ong Y.C., Lin Y., Cariou K., Gasser G. A tutorial for the assessment of the stability of organometallic complexes in biological media. J. Organomet. Chem. 2019; 906: 121059. https://doi.org/10.1016/j.jorganchem.2019.121059</mixed-citation></citation-alternatives></ref><ref id="cit41"><label>41</label><citation-alternatives><mixed-citation xml:lang="ru">Кононова М.М. Органическое вещество почвы, его природа, свойства и методы изучения. М.; 1963</mixed-citation><mixed-citation xml:lang="en">Kononova M.M. Soil Organic Matter, its Nature, Properties and Methods of Study [Organicheskoe veshchestvo pochvy, ego priroda, svoystva i metody izucheniya]. Moscow; 1963. (in Russian)</mixed-citation></citation-alternatives></ref><ref id="cit42"><label>42</label><citation-alternatives><mixed-citation xml:lang="ru">Osawa R., Kuroiso K., Goto S., Shimizu A. Isolation of tannin-degrading lactobacilli from humans and fermented foods. Appl. Environ. Microbiol. 2000; 66(7): 3093-7. https://doi.org/10.1128/aem.66.7.3093-3097.2000</mixed-citation><mixed-citation xml:lang="en">Osawa R., Kuroiso K., Goto S., Shimizu A. Isolation of tannin-degrading lactobacilli from humans and fermented foods. Appl. Environ. Microbiol. 2000; 66(7): 3093–7. https://doi.org/10.1128/aem.66.7.3093-3097.2000</mixed-citation></citation-alternatives></ref><ref id="cit43"><label>43</label><citation-alternatives><mixed-citation xml:lang="ru">Adamczyk B., Simon J., Kitunen V., Adamczyk S., Smolander A. Tannins and their complex interaction with different organic nitrogen compounds and enzymes: old paradigms versus recent advances. ChemistryOpen. 2017; 6(5): 610-4. https://doi.org/10.1002/open.201700113</mixed-citation><mixed-citation xml:lang="en">Adamczyk B., Simon J., Kitunen V., Adamczyk S., Smolander A. Tannins and their complex interaction with different organic nitrogen compounds and enzymes: old paradigms versus recent advances. ChemistryOpen. 2017; 6(5): 610–4. https://doi.org/10.1002/open.201700113</mixed-citation></citation-alternatives></ref><ref id="cit44"><label>44</label><citation-alternatives><mixed-citation xml:lang="ru">Krajka-Kuźniak V., Baer-Dubowska W. The effects of tannic acid on cytochrome P450 and phase II enzymes in mouse liver and kidney. Toxicol. Lett. 2003; 143(2): 209-16. https://doi.org/10.1016/s0378-4274(03)00177-2</mixed-citation><mixed-citation xml:lang="en">Krajka-Kuźniak V., Baer-Dubowska W. The effects of tannic acid on cytochrome P450 and phase II enzymes in mouse liver and kidney. Toxicol. Lett. 2003; 143(2): 209–16. https://doi.org/10.1016/s0378-4274(03)00177-2</mixed-citation></citation-alternatives></ref><ref id="cit45"><label>45</label><citation-alternatives><mixed-citation xml:lang="ru">Afsana K., Shiga K., Ishizuka S., Hara H. Reducing effect of ingesting tannic acid on the absorption of iron, but not of zinc, copper and manganese by rats. Biosci. Biotechnol. Biochem. 2004; 68(3): 584-92. https://doi.org/10.1271/bbb.68.584</mixed-citation><mixed-citation xml:lang="en">Afsana K., Shiga K., Ishizuka S., Hara H. Reducing effect of ingesting tannic acid on the absorption of iron, but not of zinc, copper and manganese by rats. Biosci. Biotechnol. Biochem. 2004; 68(3): 584–92. https://doi.org/10.1271/bbb.68.584</mixed-citation></citation-alternatives></ref><ref id="cit46"><label>46</label><citation-alternatives><mixed-citation xml:lang="ru">Andrade R.G., Dalvi L.T., Silva J.M.C., Lopes G.K.B., Alonso A., Hermes-Lima M. The antioxidant effect of tannic acid on the in vitro copper-mediated formation of free radicals. Arch. Biochem. Biophys. 2005; 437(1): 1-9. https://doi.org/10.1016/j.abb.2005.02.016</mixed-citation><mixed-citation xml:lang="en">Andrade R.G., Dalvi L.T., Silva J.M.C., Lopes G.K.B., Alonso A., Hermes-Lima M. The antioxidant effect of tannic acid on the in vitro copper-mediated formation of free radicals. Arch. Biochem. Biophys. 2005; 437(1): 1–9. https://doi.org/10.1016/j.abb.2005.02.016</mixed-citation></citation-alternatives></ref><ref id="cit47"><label>47</label><citation-alternatives><mixed-citation xml:lang="ru">Agrawal R., Sharma P.K., Rao G.S. Release of iron from ferritin by metabolites of benzene and superoxide radical generating agents. Toxicology. 2001; 168(3): 223-30. https://doi.org/10.1016/S0300-483X(01)00412-7</mixed-citation><mixed-citation xml:lang="en">Agrawal R., Sharma P.K., Rao G.S. Release of iron from ferritin by metabolites of benzene and superoxide radical generating agents. Toxicology. 2001; 168(3): 223–30. https://doi.org/10.1016/S0300-483X(01)00412-7</mixed-citation></citation-alternatives></ref><ref id="cit48"><label>48</label><citation-alternatives><mixed-citation xml:lang="ru">Li Y., Trush M.A., Yager J.D. DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol. Carctoogenesis. 1994; 15(7): 1421-7. https://doi.org/10.1093/carcin/15.7.1421</mixed-citation><mixed-citation xml:lang="en">Li Y., Trush M.A., Yager J.D. DNA damage caused by reactive oxygen species originating from a copper-dependent oxidation of the 2-hydroxy catechol of estradiol. Carctoogenesis. 1994; 15(7): 1421–7. https://doi.org/10.1093/carcin/15.7.1421</mixed-citation></citation-alternatives></ref><ref id="cit49"><label>49</label><citation-alternatives><mixed-citation xml:lang="ru">Kiran P., Denni M., Daniel M. Antidiabetic principles, phospholipids and fixed oil of kodo millet (Paspalum scrobiculatum Linn.). Ind. J. Appl. Res. 2014; 4(2): 13-5.</mixed-citation><mixed-citation xml:lang="en">Kiran P., Denni M., Daniel M. Antidiabetic principles, phospholipids and fixed oil of kodo millet (Paspalum scrobiculatum Linn.). Ind. J. Appl. Res. 2014; 4(2): 13–5.</mixed-citation></citation-alternatives></ref><ref id="cit50"><label>50</label><citation-alternatives><mixed-citation xml:lang="ru">Kosińska A., Karamać M., Penkacik K., Urbalewicz A., Amarowicz R. Interactions between tannins and proteins isolated from broad bean seeds (Vicia faba Major) yield soluble and non-soluble complexes. Eur. Food Res. Technol. 2011; 233(2): 213-22. https://doi.org/10.1007/s00217-011-1506-9</mixed-citation><mixed-citation xml:lang="en">Kosińska A., Karamać M., Penkacik K., Urbalewicz A., Amarowicz R. Interactions between tannins and proteins isolated from broad bean seeds (Vicia faba Major) yield soluble and non-soluble complexes. Eur. Food Res. Technol. 2011; 233(2): 213–22. https://doi.org/10.1007/s00217-011-1506-9</mixed-citation></citation-alternatives></ref><ref id="cit51"><label>51</label><citation-alternatives><mixed-citation xml:lang="ru">Koç S., Köse D.A., Avcı E., Köse K. Synthesis and thermal characterization of p-coumaric acid complexes of Co II, Ni II, Cu II and Zn II metal cations and biological applications. Hitite J. Sci. Eng. 2016; 3(1): 15-22.</mixed-citation><mixed-citation xml:lang="en">Koç S., Köse D.A., Avcı E., Köse K. Synthesis and thermal characterization of p-coumaric acid complexes of Co II, Ni II, Cu II and Zn II metal cations and biological applications. Hitite J. Sci. Eng. 2016; 3(1): 15–22.</mixed-citation></citation-alternatives></ref></ref-list><fn-group><fn fn-type="conflict"><p>The authors declare that there are no conflicts of interest present.</p></fn></fn-group></back></article>
