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Alkylresorcinols: New Potential Bioregulators in the Superorganism System (Human–Microbiota)

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Abstract

Based on the results of qualitative and quantitative analysis of alkylresorcinol pools in the intestine and in the blood, as well as their correlations with the level of tryptophan metabolites in feces, indicators of the diversity of intestinal microbiota, and clinical and laboratory data, the role of alkylresorcinols as regulatory mediators in the axis “microbiota–adipose tissue” was proposed. Changes in the content of alkylresorcinols in obesity have been shown, which probably reflects the relationship between the state of the microbiota and the metabolic characteristics of the macroorganism.

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REFERENCES

  1. Bartłomiej, S., Justyna, R.K., and Ewa, N., Bioactive compounds in cereal grains—occurrence, structure, technological significance and nutritional benefits—a review, Food Sci Technol. Int., 2012, vol. 18, no. 6, pp. 559–568.

    Article  Google Scholar 

  2. Cani, P.D., Van Hul, M., Lefort, C., Depommier, C., Rastelli, M., and Everard, A., Microbial regulation of organismal energy homeostasis, Nat. Metab., 2019, vol. 1, no. 1, pp. 34–46.

    Article  CAS  Google Scholar 

  3. Choung, R.S., Murray, J.A., Marietta, E.V., Van Dyke, C.T., and Ross, A.B., Serum alkylresorcinols as biomarkers of detary gluten exposure in coeliac disease, Aliment. Pharmacol. Ther., 2017, vol. 45, no. 5, pp. 643–652.

    Article  CAS  Google Scholar 

  4. Depommier, C., Everard, A., Druart, C., Plovier, H., Van Hul, M., Vieira-Silva, S., Falony, G., Raes, J., Maiter, D., Delzenne, N.M., de Barsy, M., Loumaye, A., Hermans, M.P., Thissen, J.-P., de Vos, W.M., and Cani, P.D., Supplementation with akkermansia muciniphila in overweight and obese human volunteers: a proof-of-concept exploratory study, Nat. Med., 2019, vol. 25, pp. 1096–1103.

    Article  CAS  Google Scholar 

  5. van Duynhoven, J., Vaughan, E.E., Jacobs, D.M., Kemperman, A.R., van Velzen, E.J.J., Gross, G., Roger, L.C., Possemiers, S., Smilde, A.K., Doré, J., Westerhuis, J.A., and Van de Wiele, T., Metabolic fate of polyphenols in the human superorganism, Proc. Natl. Acad. Sci. U. S. A., 2011, vol. 108, pp. 4531–4538.

    Article  CAS  Google Scholar 

  6. Galland, L., The gut microbiome and the brain, J. Med. Food, 2014, vol. 17, no. 12, pp. 1261–1272.

    Article  CAS  Google Scholar 

  7. Goodacre, R., Metabolomics of a superorganism, J. Nutr., 2007, vol. 137, no. 1, suppl. 1, pp. 259–266.

    Article  Google Scholar 

  8. Il’inskaya, O.N., Kolpakov, A.I., Zelenikhin, P.V., Kruglova, Z.F., Choidash, B., Doroshenko, E.V., Mulyukin, A.L., and El’-Registan, G.I., The effect of anabiosis autoinducers on the bacterial genome, Microbiology (Moscow), 2002, vol. 71, no. 2, pp. 164–168.

    Article  Google Scholar 

  9. Jalanka-Tuovinen, J., Salonen, A., Nikkilä, J., Immonen, O., Kekkonen, R., Lahti, L., Palva, A., and de Vos, W.M., Intestinal microbiota in healthy adults: temporal analysis reveals individual and common core and relation to intestinal symptoms, PLoS One, 2011, vol. 6, no. 7, art. ID 23035.

    Article  Google Scholar 

  10. Kyrø, C., Kristensen, M., Jakobsen, M.U., Halkjær, J., Landberg, R., Bueno-de-Mesquita, H.A., Christensen, J., Romieu, I., Tjønneland, A., and Olsen, A., Dietary intake of whole grains and plasma alkylresorcinol concentrations in relation to changes in anthropometry: the Danish diet, cancer and health cohort study, Comp. Study Eur. J. Clin. Nutr., 2017, vol. 71, no. 8, pp. 944–952.

    Article  Google Scholar 

  11. Lambring, C.B., Siraj, S., Patel, K., Sankpal, U.T., Mathew, S., and Basha, R., Impact of the microbiome on the immune system, Crit. Rev. Immunol., 2019, vol. 39, no. 5, pp. 313–328.

    Article  Google Scholar 

  12. Lundgren, P. and Thaiss, C.A., The microbiome–adipose tissue axis in systemic metabolism, Am. J. Physiol. Gastroin. Liver Physiol., 2020, vol. 318, no. 4, pp. 717–724.

    Article  Google Scholar 

  13. Margulis, A.B., Il’inskaya, O.N., Kolpakov, A.I., and Mufer, K., Induction of hypometabolic forms in non-spore-forming gram-positive bacteria, Uch. Zap. Kazan. Univ., Ser. Estestv. Nauki, 2005, vol. 147, no. 2, pp. 108–114.

    Google Scholar 

  14. Martins, T.P., Rouger, C., Glasser, N.R., Freitas, S., de Fraissinette, N.B., Balskus, E.P., Tasdemir, D., and Leao, P.N., Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols, Nat. Prod. Rep., 2019, vol. 36, no. 10, pp. 1437–1461.

    Article  CAS  Google Scholar 

  15. Million, M., Angelakis, E., Paul, M., Armougom, F., Leibovici, L., and Raoult, D., Comparative meta-analysis of the effect of lactobacillus species on weight gain in humans and animals, Microb. Pathog., 2012, vol. 53, pp. 100–108.

    Article  Google Scholar 

  16. Oishi, K., Yamamoto, S., Itoh, N., Nakao, R., Yasumoto, Y., Tanaka, K., Kikuchi, Y., Fukudome, S., Okita, K., and Takano-Ishikawa, Y., Wheat alkylresorcinols suppress high-fat, high-sucrose diet-induced obesity and glucose intolerance by increasing insulin sensitivity and cholesterol excretion in male mice, J. Nutr., 2015, vol. 145, no. 2, pp. 199–206.

    Article  Google Scholar 

  17. Ross, A.B., Aman, P., Andersson, R., and Kamal-Eldin, A., Chromatographic analysis of alkylresorcinols and their metabolites, J. Chromatogr., A, 2004, vol. 1054, pp. 157–164.

    Article  CAS  Google Scholar 

  18. Salvucci, E., The human-microbiome superorganism and its modulation to restore health, Int. J. Food Sci. Nutrit., 2019, vol. 70, no. 7, pp. 781–795.

    Article  CAS  Google Scholar 

  19. Schmidt, T.S.B., Raes, J., and Bork, P., The human gut microbiome: from association to modulation, Cell, 2018, vol. 172, no. 6, pp. 1198–1215.

    Article  CAS  Google Scholar 

  20. Sidhu, M. and van der Poorten, D., The gut microbiome, Aust. Fam. Physician, 2017, vol. 46, no. 4, pp. 206–211.

    PubMed  Google Scholar 

  21. Sitkin, S., Tkachenko, E.I., and Vakhitov, T., Phylometabolic core of intestinal microbiota, Alm. Clin. Med., 2015, vol. 12, p. 34.

    Google Scholar 

  22. Sun, T., Zhang, Y., Huang, H., Wang, X., Zhou, Li., Li, Sh., Huang, S., Xie, Ch., Wen, Y., Zhu, Y., Hu, X., Chen, L., Li, P., Chen, S., Yang, W., Bao, W., Hu, F.B., Cheng, J., and Sun, L.L., Plasma alkylresorcinol metabolite, a biomarker of whole-grain wheat and rye intake, and risk of ischemic stroke: a case-control study, Am. J. Clin. Nutrit., 2019, vol. 109, no. 2, pp. 1–7.

    Article  Google Scholar 

  23. Sun, Y., Yao, R., Ji, X., Wu, H., Luna, A., Zhonghua Wang, Zh., and Jetter, R., Characterization of an alkylresorcinol synthase that forms phenolics accumulating in the cuticular wax on various organs of rye (Secale cereale), Plant J., 2020, vol. 102, no. 6, pp. 1294–1312.

    Article  CAS  Google Scholar 

  24. Tap, J., Mondot, S., Levenez, F., Pelletier, E., Caron, C., Furet, J.P., Ugarte, E., Muñoz-Tamayo, R., Paslier, D.L., Nalin, R., Dore, J., and Leclerc, M., Towards the human intestinal microbiota phylogenetic core, Environ. Microbiol., 2009, vol. 11, no. 10, pp. 2574–2584.

    Article  Google Scholar 

  25. Tirosh, A., Calay, E.S., Tuncman, G., Claiborn, K.C., Inouye, K.E., Eguchi, K., Alcala, M., Rathaus, M., Hollander, K.S., Ron, I., Livne, R., Heianza, Y., Qi, L., Shai, I., Garg, R., and Hotamisligil, G.S., The short-chain fatty acid propionate increases glucagon and fabp4 production, impairing insulin action in mice and humans, Sci. Transl. Med., 2019, vol. 11, p. 120.

    Article  Google Scholar 

  26. Turnbaugh, P.J., Hamady, M., Yatsunenko, T., Cantarel, B.L., Duncan, A., Ley, R.E., Sogin, M.L., Jones, W.J., Roe, B.A., Affourtit, J.P., Egholm, M., Henrissat, B., Heath, A.C., Knight, R., and Gordon, J.I., A core gut microbiome in obese and lean twins, Nature, 2009, vol. 457, no. 7228, pp. 480–484.

    Article  CAS  Google Scholar 

  27. Wu, H., Omar, N.A.M., Håkansson, N., Wolk, A., Michaёlsson, K., and Landberg, R., Evaluation of alkylresorcinols in adipose tissue biopsies as a long-term biomarker of whole-grain wheat and rye intake in free-living Swedish men and women, Public Health Nutr., 2018, vol. 21, no. 10, pp. 1933–1942.

    Article  Google Scholar 

  28. Zhao, Y., Shi, L., Hu, Ch., and Sang, Sh., Wheat bran for colon cancer prevention: the synergy between phytochemical alkylresorcinol C21 and intestinal microbial metabolite butyrate, J. Agric. Food Chem., 2019, vol. 67, no. 46, pp. 12761–12769.

    Article  CAS  Google Scholar 

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Funding

This work was conducted under a contract (no. 0373100122119000041) for the project “Creation of a Bank of Biosamples of Blood Serum and Feces from Healthy Donors and Patients with Obesity, Metabolic Syndrome, Type II Diabetes Mellitus, Impaired Mucosal Barrier of the Gastrointestinal Tract in Order to Identify Candidate Species–Nonspecific Mediators of Quorum Sensing Systems of the Human Microbiota Modulating the Endocrine and Metabolic Function of Adipose Tissue.”

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Authors and Affiliations

  1. Rogachev National Medical Research Center of Pediatric Hematology, Oncology, and Immunology, 117997, Moscow, Russia

    A. V. Shestopalov, A. M. Gaponov, A. V. Tutelyan & A. G. Rumyantsev

  2. Center of Digital and Translational Biomedicine, LLC Center for Molecular Health, 117218, Moscow, Russia

    A. V. Shestopalov, E. D. Teplyakova, V. F. Shin, D. V. Savchuk & S. A. Rumyantsev

  3. Pirogov Russian National Research Medical University, 117997, Moscow, Russia

    A. A. Zabolotneva, O. V. Borisenko & S. A. Rumyantsev

  4. Sechenov First Moscow State Medical University, 119991, Moscow, Russia

    S. A. Appolonova & P. A. Markin

  5. Rostov State Medical University, 344022, Rostov-on-Don, Russia

    E. D. Teplyakova, V. F. Shin, N. I. Volkova & L. A. Ganenko

  6. Municipal Children’s Hospital No. 1, 344019, Rostov-on-Don, Russia

    D. V. Savchuk

  7. Center for Strategic Planning of FMBA of Russia, 119121, Moscow, Russia

    V. V. Makarov & S. M. Yudin

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  1. A. V. Shestopalov
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  2. A. M. Gaponov
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  8. A. G. Rumyantsev
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  9. E. D. Teplyakova
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  10. V. F. Shin
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  14. V. V. Makarov
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  15. S. M. Yudin
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  16. S. A. Rumyantsev
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Corresponding author

Correspondence to A. V. Shestopalov.

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Conflict of interest. The authors declare that they have no conflicts of interest.

Statement of compliance with standards of research involving humans as subjects. This study was approved by the Local Independent Ethics Committee of the Pirogov Russian National Research Medical University of the Ministry of Health of Russia. All patients signed an informed voluntary consent for the use of biological material for scientific purposes.

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Shestopalov, A.V., Gaponov, A.M., Zabolotneva, A.A. et al. Alkylresorcinols: New Potential Bioregulators in the Superorganism System (Human–Microbiota). Biol Bull Russ Acad Sci 49, 150–159 (2022). https://doi.org/10.1134/S1062359022030153

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  • DOI: https://doi.org/10.1134/S1062359022030153

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