Skip to main content

Cyclitols – Determination in Food and Bioactivity in the Human Organism

  • Chapter
  • First Online:
Analytical Methods in the Determination of Bioactive Compounds and Elements in Food

Abstract

Cyclitols are high polarity polyols, belonging to secondary metabolites, which are easily isolable from plant material. These compounds are biosynthetically derived from glucose, and occur in all living cells. They form a group of biologically active compounds and participate in many cellular processes such as: membrane biogenesis, signal transduction, ion channel physiology, osmoregulation, antioxidation, and others. The methods for the separation and determination of cyclitols include: preliminary sample preparation (drying, grinding, freezing, homogenization), sample extraction (optional: maceration, Soxhlet, ASE, MAE, SFE, UAE), isolation and purification (LLE, SPE, and others), analysis (GC-MS, HPLC, MALDI), and interpretation (identification, quantification, statistical analysis). Some other additional steps may be required, which are specific for the method chosen for the analysis. For example GC-MS analysis requires a derivatization step, while MALDI involves a laborious procedure for sample preparation. Cyclitols shows several health-promoting and therapeutic properties as follows: improving lipid profile in decreasing of serum triglycerides and total cholesterol, as well as having an insulin-mimetic effect. The beneficial properties of cyclitols are that they can be used for therapeutic purposes, particularly in neutralization of the results of chronic inflammation, which leads to increased risk of developing such metabolic disorders as diabetes, hypertension, atherosclerosis, etc. A notable factor is also good tolerance of cyclitols and their low toxicity, due to which they can be successfully used in treating pregnant women and children. Many benefits of cyclitols properties offer the possibility that these polyols may be candidates for discovery of novel drugs, food supplements and they can be used as well in cosmetic industry.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

References

  • Alberts, B., D. Bray, K. Hopkin, A. Johnson, J. Lewis, M. Raff, and K. Rober. 2013. Chapter 16 cell signaling. In Essential cell biology, ed. B. Alberts, D. Bray, K. Hopkin, A. Johnson, J. Lewis, M. Raff, and K. Rober, 4th ed., 525–555. New York: Garland Science.

    Chapter  Google Scholar 

  • Al-Daghri, N.M., M.S. Alokail, K.M. Alkharfy, A.K. Mohammed, S.H. Abd-Alrahman, S.M. Yakout, O.E. Amer, and S. Krishnaswamy. 2012. Fenugreek extract as an inducer of cellular death via autophagy in human T lymphoma Jurkat cells. BMC Complement and Alternative Medicine 12: 202.

    Article  Google Scholar 

  • Alsemari, A., F. Alkhodairy, A. Aldakan, M. Al-Mohanna, E. Bahoush, Z. Shinwari, and A. Alaiya. 2014. The selective cytotoxic anti-cancer properties and proteomic analysis of Trigonella Foenum-Graecum. BMC Complement and Alternative Medicine 14: 114.

    Article  CAS  Google Scholar 

  • Al-Suod, H., M. Ligor, I.A. Ratiu, K. Rafinska, R. Górecki, and B. Buszewski. 2017. A window on cyclitols: Characterization and analytics of inositols. Phytochemistry Letters 20: 507–519.

    Article  CAS  Google Scholar 

  • Al-Suod, H., I.A. Ratiu, M. Ligor, T. Ligor, and B. Buszewski. 2018a. Determination of sugars and cyclitols isolated from various morphological parts of Medicago sativa L. Journal of Separation Science 41: 1118–1128.

    Article  CAS  PubMed  Google Scholar 

  • Al-Suod, H., R. Gadzała-Kopciuch, and B. Buszewski. 2018b. Simultaneous HPLC-ELSD determination of sugars and cyclitols in different parts of Phacelia tanacetifolia Benth. Biochemical Systematics and Ecology 80: 32–38.

    Article  CAS  Google Scholar 

  • Al-Suod, H., P. Pomastowski, M. Ligor, V. Railean-Plugaru, and B. Buszewski. 2018c. New approach for fast identification of cyclitols by MALDI-TOF mass spectrometry. Phytochemical Analysis 29: 528–537.

    Article  CAS  PubMed  Google Scholar 

  • Al-Suod, H., I.A. Ratiu, A. Krakowska-Sieprawska, L. Lahuta, R. Górecki, and B. Buszewski. 2019a. Supercritical fluid extraction in isolation of cyclitols and sugars from chamomile flowers. Journal of Separation Science 42: 3243–3252.

    Article  CAS  Google Scholar 

  • Al-Suod, H., I.A. Ratiu, R. Górecki, and B. Buszewski. 2019b. Pressurized liquid extraction of cyclitols and sugars: Optimization of extraction parameters and selective separation. Journal of Separation Science 42: 1265–1272.

    Article  CAS  PubMed  Google Scholar 

  • Altaf, Q.A., A.H. Barnett, and A.A. Tahrani. 2015. Novel therapeutics for type 2 diabetes: Insulin resistance. Diabetes, Obesity and Metabolism 17: 319–334.

    Article  PubMed  Google Scholar 

  • Antonowski, T., A. Osowski, L. Lahuta, R. Górecki, A. Rynkiewicz, and J. Wojtkiewicz. 2019. Health-promoting properties of selected cyclitols for metabolic syndrome and diabetes. Nutrients 11: 2314.

    Article  CAS  PubMed Central  Google Scholar 

  • Awuchi, Ch.G., and K.Ch Echeta. 2019. Current developments in sugar alcohols: Chemistry, nutrition, and healthconcerns of sorbitol, xylitol, glycerol, arabitol, inositol, maltitol, and lactitol. International Journal of Advanced Academic Research 5: 1–33.

    Google Scholar 

  • Bae, M.-J., H.S. Shin, D.-W. Choi, and D.-H. Shon. 2012. Antiallergic effect of Trigonella foenum-graecum L. extracts on allergic skin inflammation induced by trimellitic anhydride in BALB/c mice. Journal of Ethnopharmacology 144: 514–522.

    Article  CAS  PubMed  Google Scholar 

  • Bates, S.H., R.B. Jones, and C.J. Bailey. 2000. Insulin-like effect of pinitol. British Journal of Pharmacology 130: 1944–1948.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Baumgartner, S., R. Genner-Ritzmann, J. Haas, R. Amado, and H. Neukom. 1986. Isolation and identification of cyclitols in carob pods (Ceratonia siliqua L.). Journal of Agricultural and Food Chemistry 34: 827–829.

    Article  CAS  Google Scholar 

  • Bizzarri, M., and G. Carlomagno. 2014. Inositol: History of an effective therapy for polycystic ovary syndrome. European Review for Medical and Pharmacological Sciences 18: 1896–1903.

    CAS  PubMed  Google Scholar 

  • Bizzarri, M., A. Fuso, S. Dinicola, A. Cucina, and A. Bevilacqua. 2016. Pharmacodynamics and pharmacokinetics of inositol(s) in health and disease. Expert Opinion on Drug Metabolism and Toxicology 12: 1181–1196.

    Article  CAS  PubMed  Google Scholar 

  • Chauhan, P.S., K.K. Gupta, and S. Bani. 2011. The immunosuppressive effects of Agyrolobium roseum and pinitol in experimental animals. International Immunopharmacology 11: 286–291.

    Article  CAS  PubMed  Google Scholar 

  • Cheang, K.I., J.P. Baillargeon, P.A. Essah, R.E. Ostlund Jr., T. Apridonize, L. Islam, and J.E. Nestler. 2008. Insulin-stimulated release of D-chiro-inositol-containing inositol phosphoglycan mediator correlates with insulin sensitivity in women with polycystic ovary syndrome. Metabolism Clinical and Exppermental 57: 1390–1397.

    Article  CAS  Google Scholar 

  • Choi, M.-S., W.-H. Lee, E.-Y. Kwon, M.A. Kang, M.-K. Lee, Y.B. Park, and S.-M. Jeon. 2007. Effects of soy pinitol on the pro-inflammatory cytokines and scavenger receptors in oxidized low-density lipoprotein-treated THP-1 macrophages. Journal of Medicinal Food 10: 594–601.

    Article  CAS  PubMed  Google Scholar 

  • Choi, M.-S., M.-K. Lee, U.J. Jung, H.-J. Kim, G.-M. Do, Y.B. Park, and S.-M. Jeon. 2009. Metabolic response of soy pinitol on lipid-lowering, antioxidant and hepatoprotective action in hamsters fed-high fat and high cholesterol diet. Molecular Nutrition and Food Research 53: 751–759.

    Article  CAS  PubMed  Google Scholar 

  • Christou, Ch., E. Poulli, S. Yiannopoulos, and A. Agapiou. 2019. GC–MS analysis of D-pinitol in carob: Syrup and fruit (flesh and seed). Journal of Chromatography B 1116: 60–64.

    Article  CAS  Google Scholar 

  • Clements, R.S., and B. Darnell. 1980. Myo-inositol content of common foods: Development of a high-myo-inositol diet. The American Journal of Clinical Nutrition 33: 1954–1967.

    Article  CAS  PubMed  Google Scholar 

  • Colazingari, S., M. Treglia, R. Najjar, and A. Bevilacqua. 2013. The combined therapy myo-inositol plus D-chiro-inositol, rather than D-chiro-inositol, is able to improve IVF outcomes: Results from a randomized controlled trial. Archives of Gynecology and Obstetrics 288: 1405–1411.

    Article  CAS  PubMed  Google Scholar 

  • Costantino, D., G. Minozzi, F. Minozzi, and C. Guaraldi. 2009. Metabolic and hormonal effects of myo-inositol in women with polycystic ovary syndrome: A double-blind trial. European review for medicinal and pharmacological. Science 13: 105–110.

    CAS  Google Scholar 

  • Croze, M.L., and C.O. Soulage. 2013. Potential role and therapeutic interests of myo-inositol in metabolic diseases. Biochimie 95: 1811–1827.

    Article  CAS  PubMed  Google Scholar 

  • Dai, Z., S.K. Chung, D. Miao, K.S. Lau, A.W. Chan, and A.W. Kung. 2011. Sodium/myo-inositol cotransporter 1 and myo-inositol are essential for osteogenesis and bone formation. Journal of Bone and Mineral Ressearch 26: 582–590.

    Article  CAS  Google Scholar 

  • Dang, N.T., R. Mukai, K.I. Yoshida, and H. Ashida. 2010. D-Pinitol and myo-inositol stimulate translocation of glucose transporter 4 in skeletal muscleof C57BL/6 mice. Bioscience, Biotechnology, and Biochemistry 74: 1062–1067.

    Article  CAS  PubMed  Google Scholar 

  • Donahue, J.L., S.R. Alford, J. Torabinejad, R.E. Kerwin, A. Nourbakhsh, W.K. Ray, M. Hernick, X. Huang, B.M. Lyons, P.P. Hein, and G.E. Gillaspy. 2010. The arabidopsis thaliana myo-inositol 1-phosphate synthase1 gene is required for myo-inositol synthesis and suppression of cell death. Plant Cell 22: 888–903.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ferreira, H.C., C.P. Serra, V.S. Lemos, F.C. Braga, and S.F. Cortes. 2007. Nitric oxide-dependent vasodilatation by ethanolic extract of Hancornia speciosa via phosphatidyl-inositol 3-kinase. Journal of Ethnopharmacology 109: 161–164.

    Article  CAS  PubMed  Google Scholar 

  • Fougere, F., D. Le Rudulier, and J.G. Streeter. 1991. Effects of salt stress on amino acid, organic acid, and carbohydrate composition of roots, bacteroids, and cytosol of alfalfa (Medicago sativa L.). Plant Physiology 96: 1228–1236.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Fouka, P., H. Alexopoulos, I. Chatzi, S.G. Dedos, M. Samiotaki, G. Panayotou, P. Politis, A. Tzioufas, and M.C. Dalakas. 2017. Antibodies to inositol 1,4,5-triphosphate receptor 1 in patients with cerebellar disease. Neurol Neuroimmunol Neuroinflamm. 4: e306.

    Article  PubMed  Google Scholar 

  • Frej, A.D., G.P. Otto, and R.S. Williams. 2017. Tipping the scales: Lessons from simple model systems on inositol imbalance in neurological disorders. European Journal of Cell Biology 96: 154–163.

    Article  CAS  PubMed  Google Scholar 

  • Gao, Y., M. Zhang, T. Wu, M. Xu, H. Cai, and Z. Zhang. 2015. Effects of D-pinitol on insulin resistance through the PI3K/Akt signaling pathway in type 2 diabetes mellitus rats. Journal of Agricultural and Food Chemictry 63: 6019–6026.

    Article  CAS  Google Scholar 

  • Geethan, P.K.M.A., and P.S.M. Prince. 2008. Antihyperlipidemic effect of D-pinitol on streptozotocin-induced diabetic Wistar rats. Journal of Biochemicla and Molecular Toxicology 22: 220–224.

    Article  CAS  Google Scholar 

  • Genazzani, A.D., C. Lanzoni, F. Ricchieri, and V.M. Jasonni. 2008. Myoinositol administration positively affects hyperinsulinemia and hormonal parameters in overweight patients with polycystic ovary syndrome. Gynecological Endocrinology 24: 139–144.

    Article  CAS  PubMed  Google Scholar 

  • Ghfar, A.A., S.M. Wabaidur, A. Yacine, Z.A. Alothman, M.R. Khan, and N.H. Al-Shaalan. 2015. Simultaneous determination of monosaccharides and oligosaccharides in dates using liquid chromatographyelectrospray ionization mass spectrometry. Food Chemistry 176: 487–492.

    Article  CAS  PubMed  Google Scholar 

  • Greene, N.D., K.-Y. Leung, and A.J. Copp. 2017. Inositol, neural tube closure and the prevention of neural tube defects. Birth Defects Research 109: 68–80.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Griffith, H.R., J.A. den Hollander, O.C. Okonkwo, T. O’Brien, R.L. Watts, and D.C. Marson. 2008. Brain metabolism differs in Alzheimer’s disease and Parkinson’s disease dementia. Alzheimer's & Dementia 4: 421–427.

    Article  CAS  Google Scholar 

  • Heimark, D., J. McAllister, and J. Larner. 2014. Decreased myo-inositol to chiro-inositol (M/C) ratios and increased M/C epimerase activity in PCOS theca cells demonstrate increased insulin sensitivity compared to controls. Endocrine Journal 61: 111–117.

    Article  CAS  PubMed  Google Scholar 

  • Hernandez-Mijares, A., C. Banuls, J.E. Peris, N. Monzo, A. Jover, L. Bellod, V.M. Victor, and M. Rocha. 2013. A single acute dose of pinitol from a naturally-occurring food ingredient decreases hyperglycaemia and circulating insulin levels in healthy subjects. Food Chemistry 141: 1267–1272.

    Article  CAS  PubMed  Google Scholar 

  • Hossain, M.S., M. Persicke, A.I. El-Sayed, J. Kalinowski, and K.J. Dietz. 2017. Metabolite profiling at the cellular and subcellular level reveals metabolites associated with salinity tolerance in sugar beet. Journal of Experimental Botany 68: 5961–5976.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Kido, E.A., H.R.C. Ferreira Neto, R.L.O. Silva, L.C. Belarmino, J.P. Bezerra Neto, N.M. Soares-Cavalcanti, V. Pandolfi, M. Da Silva, A.L. Nepomuceno, and A.M. Benko-Iseppon. 2013. Expression dynamics and genome distribution of osmoprotectants in soybean: Identifying important components to face abiotic stress. BMC Bioinformatics 14: S7.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Larner, J. 2002. D-chiro-inositol–its functional role in insulin action and its deficit in insulin resistance. International Journal of Experimental Diabetes Research 3: 47–60.

    Article  PubMed  PubMed Central  Google Scholar 

  • Larner, J., D.L. Brautigan, and M.O. Thorner. 2010. D-chiro-inositol glycans in insulin signaling and insulin resistance. Molecular Medicine 16: 543–552.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lazarenko, R., J. Geisler, D. Bayliss, J. Larner, and C. Li. 2014. D-chiro-inositol glycan stimulates insulin secretion in pancreatic β cells. Molecular and Cellular Endocrinology 387: 1–7.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lein, S., M. Van Boven, R. Holser, E. Decuypere, G. Flo, S. Lievens, and M. Cokelaere. 2002. Simultaneous determination of carbohydrates and simmondsins in jojoba seed meal (Simmondsia chinensis) by gas chromatography. Journal of Chromatography A 977: 257–264.

    Article  CAS  PubMed  Google Scholar 

  • Ligor, M., I.A. Ratiu, A. Kiełbasa, H. Al-Suod, and B. Buszewski. 2018. Extraction approaches used for the determination of biologically active compounds (cyclitols, polyphenols and saponins) isolated from plant material. Electrophoresis 39: 1860–1874.

    Article  CAS  Google Scholar 

  • Lin, T.-H., T.-W. Tan, T.-H. Tsai, C.-C. Chen, T.-F. Hsieh, S.-S. Lee, H.-H. Liu, W.-C. Chen, and C.-H. Tang. 2013. D-pinitol inhibits prostate cancer metastasis through inhibition of αVβ3 integrin by modulating FAK, c-Src and NF-κB pathways. International Journal of Molecular Sciences 14: 9790–9802.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Liu, M., S. Jevtic, K. Markham-Coultes, N.P. Ellens, M.A. O’Reilly, K. Hynynen, I. Aubert, and J. McLaurin. 2018. Investigating the efficacy of a combination Aβ-targeted treatment in a mouse model of Alzheimer’s disease. Brain Research 1678: 138–145.

    Article  CAS  PubMed  Google Scholar 

  • López-Sánchez, J.I., D.A. Moreno, and C. García-Viguera. 2018. D-pinitol, a highly valuable product from carob pods: Health-promoting effects and metabolic pathways of this natural super-food ingredient and its derivatives. AIMS Agriculture and Food 3: 41–63.

    Article  Google Scholar 

  • Murakeözy, É.P., N. Smirnoff, Z. Nagy, and Z. Tuba. 2002. Seasonal accumulation pattern of pinitol and other carbohydrates in Limonium gmelini subsp. hungarica. Journal of Plant Physiology 159: 485–490.

    Article  Google Scholar 

  • Nabors, L., Th. Hedrick. 2001. Sweeteners, Food Additives (2nd ed. Revised and expanded), eds. A. L. Branen, P. M. Davidson, S. Salminen and J. Thorngate, pp. 467–799. New York: Marcel Dekker.

    Google Scholar 

  • Nasar-Abbas, S.M., Z.E. Huma, and T.-H. Vu. 2016. Carob kibble: A bioactive-rich food ingredient. Comprehensive Reviews in Food Science and Food Safety 15: 63–72.

    Article  CAS  PubMed  Google Scholar 

  • Ncube, B., J.F. Finnie, and J. Van Staden. 2012. Quality from the field: The impact of environmental factors as quality determinants in medicinal plants. South African Journal of Botany 82: 11–20.

    Article  Google Scholar 

  • Nestler, J.E., E.R. Reilly, K.I. Cheang, L.M. Bachmann, and R.W. Downs Jr. 2012. A pilot study: Effects of decreasing serum insulin with diazoxide on vitamin D levels in obese women with polycystic ovary syndrome. Transactions of the American Clinical and Climatological Association 123: 209–219.

    PubMed  PubMed Central  Google Scholar 

  • Orthen, B., and M. Popp. 2000. Cyclitols as cryoprotectants for spinach and chickpea thylakoids. Environmental and Experimental Botany 44: 125–132.

    Article  CAS  PubMed  Google Scholar 

  • Oszukowski, P., A. Jakimiuk, M. Spaczyński, J. Szamatowicz, A. Karowicz-Bilińska, E. Nowak-Markwitz, L. Putowski, and T. Isaat. 2014. Stanowisko Zespołu Ekspertów Polskiego Towarzystwa Ginekologicznego dotyczące stosowania preparatów zawierających myo-inozytol przez pacjentki z zespołem policystycznych jajników (PCOS) – (opinion of the expert panel of the polish gynecological society concerning use of products containing myo-inositol by patients with polycystic ovary syndrome (PCOS)). Ginekologia Polska 85: 158–160. (in Polish).

    Google Scholar 

  • Owczarczyk-Saczonek, A., L.B. Lahuta, M. Ligor, W. Placek, R. Górecki, and B. Buszewski. 2018a. The healing-promoting properties of selected cyclitols – A review. Nutrients 10: 1891.

    Article  PubMed Central  CAS  Google Scholar 

  • Owczarczyk-Saczonek, A., L.B. Lahuta, W. Placek, and R.J. Górecki. 2018b. The potential benefits of plant cyclitols in the treatment of psoriasis. Polish Annals of Medicine 25: 166–171.

    Google Scholar 

  • Özturan, A., S. Arslan, B. Kocaadam, E. Elibol, İ. İmamoğlu, and M.G. Karadağ. 2019. Effect of inositol and its derivatives on diabetes: A systematic review. Critical Reviews in Food Science and Nutrition 59: 1124–1136.

    Article  PubMed  CAS  Google Scholar 

  • Pascente, R., F. Frigerio, M. Rizzi, L. Porcu, M. Boido, J. Davids, M. Zaben, D. Tolomeo, M. Filibian, and W.P. Gray. 2016. Cognitive deficits and brain myo-inositol are early biomarkers of epileptogenesis in a rat model of epilepsy. Neurobiology of Disease 93: 146–155.

    Article  CAS  PubMed  Google Scholar 

  • Paul, C., A.S. Laganà, P. Maniglio, O. Triolo, and D.M. Brady. 2016. Inositol’s and other nutraceuticals’ synergistic actions counteract insulin resistance in polycystic ovarian syndrome and metabolic syndrome: State-of-the-art and future perspectives. Gynecological Endocrinology 32: 431–438.

    Article  CAS  PubMed  Google Scholar 

  • Pereira, A.B.D., T.M. Veríssimo, M.A. de Oliveira, I.A. de Araujo, R.J. Alves, and F.C. Braga. 2012. Development and validation of an HPLC-DAD method for quantification of bornesitol in extracts from Hancornia speciosa leaves after derivatization with p-toluenesulfonyl chloride. Journal of Chromatograhy B. 887–888: 133–137.

    Article  CAS  Google Scholar 

  • Posternak, Th., D. Reymond, and W. Haerdi. 1955. Recherchesdans la série des cyclitols XX. Chromatographie sur papier de cyclitols et de cycloses. Helvetica Chimica Acta 38: 191–194.

    Article  CAS  Google Scholar 

  • Raju, J., J. Paltolla, M. Swamy, and C. Rao. 2004. Diosgenin, a steroid saponin of Trigonellafoenumgraecum (fenugreek), inhibits azoxymethane-induced aberrant crypt foci formation in F344 rats and induces apoptosis in HT-29 human colon cancer cells. Cancer Epidemiology, Biomarkers & Prevention 13: 1392–1398.

    Article  CAS  Google Scholar 

  • Ratiu, I.A., H. Al-Suod, M. Ligor, T. Ligor, V. Railean-Plugaru, and B. Buszewski. 2018. Complex investigation of extraction techniques applied for cyclitols and sugars isolation from different species of Solidago genus. Electrophoresis 39: 1966–1974.

    Article  CAS  Google Scholar 

  • Ratiu, I.A., H. Al-Suod, M. Ligor, T. Ligor, A. Krakowska, R. Górecki, and B. Buszewski. 2019. Simultaneous determination of cyclitols and sugars following a comprehensive investigation of 40 plants. Food Analytical Methods 12: 1466–1478.

    Article  Google Scholar 

  • Ratiu, I.A., H. Al-Suod, M. Bukowska, M. Ligor, and B. Buszewski. 2020. Correlation study of honey regarding their physicochemical properties and sugars and cyclitols content. Molecules 25: 34.

    Article  CAS  Google Scholar 

  • Rengarajan, T., N. Nandakumar, P. Rajendran, M.K. Ganesh, M.P. Balasubramanian, and I. Nishigaki. 2015. D-pinitol mitigates tumor growth by modulating interleukins and hormones and induces apoptosis in rat breast carcinogenesis through inhibition of NF-κB. Journal of Physiology and Biochemistry 71: 191–204.

    Article  CAS  PubMed  Google Scholar 

  • Richter, A., and M. Popp. 1992. The physiological importance of accumulation of cyclitolsin Vis cum album L. New Phytologist 121: 431–438.

    Article  CAS  PubMed  Google Scholar 

  • Rouzi, A.A., and M.S. Ardawi. 2006. A randomized controlled trial of the efficacy of rosiglitazone and clomiphene citrate versus metformin and clomiphene citrate in women with clomiphene citrate-resistant polycystic ovary syndrome. Fertility and Sterility 85: 428–435.

    Article  CAS  PubMed  Google Scholar 

  • Ruiz-Aceituno, L., S. Rodríguez-Sánchez, A.I. Ruiz-Matute, L. Ramos, A.C. Soria, and M.L. Sanz. 2013. Optimisation of a biotechnological procedure for selective fractionation of bioactive inositols in edible legume extracts. Journal of the Science and Food Agriculture 93: 2797–2803.

    Article  CAS  Google Scholar 

  • Ruiz-Aceituno, L., M.J. García-Sarrió, B. Alonso-Rodriguez, L. Ramos, and M.L. Sanz. 2016. Extraction of bioactive carbohydrates from artichoke (Cynarascolymus L:) external bracts using microwave assisted extraction and pressurized liquid extraction. Food Chemistry 196: 1156–1162.

    Article  CAS  PubMed  Google Scholar 

  • Sacchi, S., F. Marinaro, D. Tondelli, and A. La Marca. 2016. Modulation of gonadotrophin induced steroidogenic enzymes in granulosa cells by d-chiro-inositol. Reproductive Biology and Endocrinology 14: 52.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Saleem, F., and S.W. Rizvi. 2017. New therapeutic approaches in obesity and metabolic syndrome associated with polycystic ovary syndrome. Cureus 9: e1844.

    PubMed  PubMed Central  Google Scholar 

  • Sanz, M.L., J. Sanz, and I. Martı́nez-Castro. 2004. Presence of some cyclitols in honey. Food Chemistry 84: 133–135.

    Article  CAS  Google Scholar 

  • Sanz, M.L., I. Martínez-Castro, and M.V. Moreno-Arribas. 2008. Identification of the origin of commercial enological tannins by the analysis of monosaccharides and polyalcohols. Food Chemistry 111: 778–783.

    Article  CAS  Google Scholar 

  • Schulz, E., T. Gori, and T. Münzel. 2011. Oxidative stress and endothelial dysfunction in hypertension. Hypertension Research 34: 665–673.

    Article  CAS  PubMed  Google Scholar 

  • Sengupta, S., and A.L. Majumder. 2010. Porteresia coarctata (Roxb.) Tateoka, a wild rice: A potential model for studying salt-stress biology in rice. Plant, Cell & Environment 33: 526–542.

    Article  CAS  Google Scholar 

  • Sengupta, S., B. Patra, S. Ray, and A.L. Majumder. 2008. Inositol methyl tranferase from a halophytic wild rice, Porteresia coarctata Roxb. (Tateoka): Regulation of pinitol synthesis under abiotic stress. Plant, Cell & Environment 31: 1442–1459.

    Article  CAS  Google Scholar 

  • Shabbeer, S., M. Sobolewski, R.K. Anchoori, S. Kachhap, M. Hidalgo, A. Jimeno, N.E. Davidson, M. Carducci, and S.R. Khan. 2009. Fenugreek: A naturally occurring edible spice as an anticancer agent. Cancer Biology & Therapy 8: 272–278.

    Article  CAS  Google Scholar 

  • Sharma, N., M.K. Verma, D.K. Gupta, N.K. Satti, and R.K. Khajuria. 2016. Isolation and quantification of pinitol in Argyrolobiumroseum plant, by 1H NMR. Journal of Saudi Chemical Society 20: 81–87.

    Article  CAS  Google Scholar 

  • Shashkin, P.N., L.C. Huang, J. Larner, G.E. Vandenhoff, and A. Katz. 2002. Fasting decreases the content of D-chiroinositol in human skeletal muscle. International Journal of Experimental Diabetes Research 3: 163–169.

    Article  PubMed  PubMed Central  Google Scholar 

  • Sikorski, L., A.I. Piotrowicz-Cieslak, and B. Adomas. 2013. Phytotoxicity of sodium cloride towards common duckweed (Lemna minor L.) and yellow lupin (Lupinus Luteus L.). Archives of Environmental Protection 39: 117–128.

    Article  CAS  Google Scholar 

  • Silva, G., F. Braga, M. Lima, J. Pesquero, V. Lemos, and S. Cortes. 2011. Hancornia speciosa Gomes induces hypotensive effect through inhibition of ACE and increase on NO. Journal of Ethnopharmacology 137: 709–713.

    Article  CAS  PubMed  Google Scholar 

  • Silva, G.C., F.C. Braga, V.S. Lemos, and S.F. Cortes. 2016. Potent antihypertensive effect of Hancornia speciosa leaves extract. Phytomedicine 23: 214–219.

    Article  PubMed  Google Scholar 

  • Silverstone, P.H., B.M. McGrath, and H. Kim. 2005. Bipolar disorder and myo-inositol: A review of the magnetic resonance spectroscopy findings. Bipolar Disorders 7: 1–10.

    Article  CAS  PubMed  Google Scholar 

  • Sortino, M.A., S. Salomone, M.O. Carruba, and F. Drago. 2017. Polycystic ovary syndrome: Insights into the therapeutic approach with inositols. Frontiers in Pharmacology 8: 341.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Tetik, N., and E. Yüksel. 2014. Ultrasound-assisted extraction of D-pinitol from carob pods using response surface methodology. Ultrasonics Sonochemistry 21: 860–865.

    Article  CAS  PubMed  Google Scholar 

  • Tetik, N., I. Turhan, H.R. Oziyci, and M. Karhan. 2011. Determination of D-pinitol in carob syrup. International Journal of Food Sciences and Nutrition 62: 572–576.

    Article  CAS  PubMed  Google Scholar 

  • Turhan, I. 2014. Relationship between sugar profile and D-pinitol content of pods of wild and cultivated types of carob bean (Ceratonia siliqua L.). International Journal of Food Properties 17: 363–370.

    Article  CAS  Google Scholar 

  • Unfer, V., F. Facchinetti, B. Orrù, B. Giordani, and J. Nestler. 2017. Myo-inositol effects in women with PCOS: A meta-analysis of randomized controlled trials. Bios 6: 647–658.

    CAS  Google Scholar 

  • Wang, L., and C.L. Weller. 2006. Recent advances in extraction of nutraceuticals from plants. Trends in Food Science & Technology 17: 300–312.

    Article  CAS  Google Scholar 

  • Zhang, B., C. Gao, Y. Li, and M. Wang. 2018. D-chiro-inositol enriched Fagopyrum tataricum (L.) Gaench extract alleviates mitochondrial malfunction and inhibits ER stress/JNK associated inflammation in the endothelium. Journal of Ethnopharmacology 214: 83–89.

    Article  CAS  PubMed  Google Scholar 

  • Zheng, K., Z. Zha, N. Lin, Y. Wu, Y. Xu, and W. Zhang. 2017. Protective effect of pinitol against inflammatory mediators of rheumatoid arthritis via inhibition of protein tyrosine phosphatase non-receptor type 22 (PTPN22). Medical Science Monitor: International Medical Journal of Experimental and Clinical Research 23: 1923–1932.

    Article  CAS  Google Scholar 

  • Zygmunt, B., and J. Namieśnik. 2003. Preparation of samples of plant material for chromatographic analysis. Journal of Chromatographic Science 41: 109–116.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Magdalena Ligor .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2021 Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Ligor, M. et al. (2021). Cyclitols – Determination in Food and Bioactivity in the Human Organism. In: Jeszka-Skowron, M., Zgoła-Grześkowiak, A., Grześkowiak, T., Ramakrishna, A. (eds) Analytical Methods in the Determination of Bioactive Compounds and Elements in Food. Food Bioactive Ingredients. Springer, Cham. https://doi.org/10.1007/978-3-030-61879-7_7

Download citation

Publish with us

Policies and ethics