Skip to main content
SpringerLink
Log in

Modification of quebrachitol extracted from natural rubber serum (NRS) to l-chiro-inositol for pharmaceutical and nutraceutical applications

  • Original Paper
  • Published:
Journal of Rubber Research Aims and scope Submit manuscript

Abstract

Inositols are a class of biologically active compounds which can be used as precursors for the synthesis of a wide range of bioactive products. Lately, there is growing awareness on the importance of developing chiral compounds in the pharmaceutical and nutraceutical industries. This new emphasis on chiral compounds boils down to safety matters, with an aim to select the right enantiomer for desired biological activities. Natural rubber serum (NRS) has the advantage as it possesses a significant percentage of naturally occurring bioactive inositol compounds. For this study, considerable amounts of quebrachitol (2-O-methyl-l-chiro-inositol) were isolated from NRS using membrane separation technology and converted to l-chiro-inositol crystals. Characterisations of the resulting inositol compounds were performed using Fourier transform infrared spectroscopy (FTIR), high-performance liquid chromatography–mass spectrometry (LCMS) and liquid-state nuclear magnetic resonance (NMR) spectroscopy methods. FTIR and NMR results for the l-chiro-inositol compound obtained showed similar spectrums as the commercial control, while LCMS mass spectra was demonstrated to be at m/z 179.03 (M–H)− in the negative ionisation mode, confirming the compound to be l-chiro-inositol. Thus, it can be concluded that quebrachitol from NRS obtained via membrane separation technology and its modified inositol derivatives have high potential market value to be used as building blocks for pharmaceutical and nutraceutical applications. Quebrachitol already exists naturally as an enantiomer and chiral compound in the rubber tree, and instead of being treated as a waste product, its usage can actively contribute to tackling environmental pollution from rubber processing effluents.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

Data availability

The data presented in this study are available from the corresponding author upon request.

References

  1. Bakti NAK, Mohd. Zin AK (1989) Treatment of rubber effluent with high rate algal pond. J Nat Rubber Res 4(3):179–185

    CAS  Google Scholar 

  2. Tata SJ (1980) Distribution of proteins between fractions of Hevea latex separated by ultracentrifugation. J Rubber Res Inst Malay 28:77

    CAS  Google Scholar 

  3. Lau CM (1996) Quebrachitol—a carbohydrate extract from Hevea latex. Rubber Research Institute of Malaysia, pp 1–21

  4. Bottier C (2020) Chapter Seven—biochemical composition of Hevea brasiliensis latex: a focus on the protein, lipid, carbohydrate and mineral contents. Adv Bot Res 93:201–237

    Article  CAS  Google Scholar 

  5. Laua CM (1996) Quebrachitol—an additional role for Hevea latex. Rubber Dev 49(1/2):11–13

    Google Scholar 

  6. McCance RA, Lawrence RD (1933) An investigation of quebrachitol as a sweetening agent for diabetics. Biochem J 27(4):986–989

    Article  CAS  Google Scholar 

  7. Díaz M, González A, Castro-Gamboa I, Gonzalez D, Rossini C (2008) First record of l-quebrachitol in Allophylus edulis (Sapindaceae). Carbohyd Res 343:2699–2700

    Article  Google Scholar 

  8. Kallio H, Lassila M, Jarvenpaa E, Haraldsson GG, Jonsdottir S, Yang B (2009) Inositols and methylinositols in sea buckthorn (Hippophae rhamnoides) berries. J Chromatogr B 877:1426–1432

    Article  CAS  Google Scholar 

  9. Alphen JV (1951) Quebrachitol. J Ind Eng Chem 43(1):141–145

    Article  Google Scholar 

  10. Kiddle JJ (1995) Quebrachitol: a versatile building block in the construction of naturally occurring bioactive materials. Chem Rev 95:2189–2202

    Article  CAS  Google Scholar 

  11. Baars SM, Hoberg HO (2006) Improved synthesis of dicyclohexylidene protected quebrachitol and its use in the synthesis of l-chiro-inositol derivatives. Carbohyd Res 341:1680–1684

    Article  CAS  Google Scholar 

  12. Chida N, Yamada K, Suzuki M, Ogawa S (1992) Facile synthesis of some l-sugar derivatives from l-quebrachitol. J Carbohydr Chem 11(2):137–148

    Article  CAS  Google Scholar 

  13. Akiyama T, Ohnar M, Shima H, Ozaki S (1991) Total synthesis of cyclophellitol from l-Quebrachitol. Synlett. https://doi.org/10.1055/s-1991-20895

    Article  Google Scholar 

  14. Cid MB, Alfonso F, Martίn-Lomas M (2003) l-chiro-Inositol derivatives from myo-Inositol. Building Blocks for Inositolphosphoglycans. Synlett 9:1370–1372

    Google Scholar 

  15. Darrow JJ (2007) The patentability of enantiomers: implications for the pharmaceutical industry, vol 2. Stanford Technol Law Rev. https://ssrn.com/abstract=1698920

  16. Rentsch KM (2002) The importance of stereoselective determination of drugs in the clinical laboratory. J Biochem Biophys Methods 54(1–3):1–9

    Article  CAS  Google Scholar 

  17. Nguyen LA, He H, Pham-Huy C (2006) Chiral drugs: an overview. Int J Biomed Sci 2(2):85–100

    CAS  Google Scholar 

  18. Katzung BG (2004) Basic and clinical pharmacology, 14th edn. Lange Medical Books/McGraw-Hill Education, New York

    Google Scholar 

  19. Business Analytic Centre (BAC) (2015) L-Inositol (CAS 551-724): Market Research Report 2015. Available at: Market Publishers Ltd

  20. Sumaiya ZA, Gregory KFL, Luqman CA, Salmiah A, Robiah Y, Thomas SYC (2009) Effects of temperature and cooling modes on yield, purity and particle size distribution of dihydroxystearic acid crystals. Eur J Sci Res 33(3):471–479

    Google Scholar 

  21. Szterner P, Biernat M (2022) Effect of reaction time, heating and stirring rate on the morphology of HAp obtained by hydrothermal synthesis. J Therm Anal Calorim 147:13059–13071

    Article  CAS  Google Scholar 

  22. Du CM, Zuo KQ, Wang XY, Huang SY, Liu B, Xiao GY, Lu YP (2022) Effect of reaction time on the microstructure and properties of in-situ hopeite chemical conversion coatings formed by self-corrosion on zinc alloy. J Market Res 18:4445–4455

    CAS  Google Scholar 

  23. AgraQuant® Total aflatoxin enzyme-linked immunosorbent assays (ELISA) Test. Romer Labs

  24. Kohl TO, Ascoli CA (2017) Direct competitive enzyme-linked immunosorbent assay (ELISA). Cold Spring Harb Protoc. https://doi.org/10.1101/pdb.prot093740

    Article  Google Scholar 

  25. AOAC Official Method 999.11 (2000) Determination of lead, cadmium, copper, iron, and zinc in foods. Atomic absorption spectrophotometry after dry ashing. First Action 1999. NMLK–AOAC method. J AOAC Int 83:1204–1206

  26. AOAC Official Method 986.15 (1980) Arsenic, cadmium, lead, selenium, and zinc in human and pet foods. Multielement method. First action 1986. Final action 1988. Codex-adopted–AOAC method. J AOAC Int 63:485–487

  27. APHA Method 3112B: Standard methods for the examination of water and wastewater—metals in water by CV-AAS. American Public Health Association

  28. APHA Method 3125B: Standard methods for the examination of water and wastewater—metals in water by ICP/MS. American Public Health Association

  29. Jiang SK, Zhang GM, Wu Y, Meng ZH, Xue M (2014) Isolation and characterisation of l-quebrachitol from rubber factory wastewater. J Nat Rubber Res 17(1):23–33

    Google Scholar 

  30. Danwanichakul P, Pohom W, Yingsampancharoen J (2019) l-Quebrachitol from acidic serum obtained after rubber coagulation of skim natural rubber latex. Ind Crops Prod 137:157–161

    Article  CAS  Google Scholar 

  31. Hu B, Zhou Y, Luo MC, Wei YC, Liu GX, Liao S, Zhao Y (2021) Influence of l-quebrachitol on the properties of centrifuged natural rubber. E-Polymers 21(1):420–427

    Article  CAS  Google Scholar 

  32. Xue M, Lv Z, Chen J, Dong XM, Meng ZH, Dong X, Zhang DX, Wu Y, Jiang SK, Li M (2014) Analysis of l-quebrachitol from the waste water of rubber latex serum using hydrophilic interaction chromatography and evaporative light scattering detector method. J Liq Chromatogr Relat Technol 38(1):92–96

    Article  Google Scholar 

  33. Hu B, Cui H, Shi S, Long A, Zhao Y, Liao S (2021) A new method of extracting l-quebrachitol from serum obtained from acid coagulation of natural rubber latex. J Nat Rubber Res 24:587–593

    Article  CAS  Google Scholar 

  34. Kim BH, Park JY, Jang JB, Moon DC (2012) LC-MS/MS method for the quantification of myo- and chiro-inositol as the urinary biomarkers of insulin resistance in human urine. Biomed Chromatogr 26(4):429–433

    Article  CAS  Google Scholar 

  35. Abraham RJ, Byrne JJ, Griffiths L, Koniotou R (2005) 1H chemical shifts in NMR: Part 22—prediction of the 1H chemical shifts of alcohols, diols and inositols in solution, a conformational and solvation investigation. Magn Reson Chem 43:611–624

    Article  CAS  Google Scholar 

  36. Singleton J, Hoberg JO (2009) Chiro-inositols in organic synthesis. Mini-Rev Org Chem 6:1–8

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research study was supported by the Malaysian Rubber Board (MRB). The authors would like to thank the Director General of the MRB for permission to publish this work. We would like to express our appreciation to fellow MRB colleagues Pn. Aimi Izyana Ismail, Pn. Nurhafizah Jaffar, En. Mohd Mustakiem Mustafar and Pn. Fatin Syahirah Mohd Arif for their assistance in conducting the experiments. We are also grateful to Dr. Devaraj Veerasamy and Mr. Lau Chee Mun (retired MRB research officers) for their guidance pertaining to chemical modification works. Similarly, we wish to thank Research Instruments Sdn Bhd (Waters Analytical Instruments Sdn Bhd) for their support in the LCMS analyses.

Funding

This research was funded by the Malaysian Rubber Board.

Author information

Authors and Affiliations

  1. Rubber Research Institute of Malaysia, Malaysian Rubber Board, 47000, Sungai Buloh, Selangor, Malaysia

    Christine Sue Chen Lee, Manroshan Singh, Dazylah Darji, Azhar Ahmad & Zairossani Mohd Nor

  2. Bruker (Malaysia) Sdn Bhd, 11900, Bayan Lepas, Pulau Pinang, Malaysia

    Chin-Hoe Teh

Authors
  1. Christine Sue Chen Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Manroshan Singh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chin-Hoe Teh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dazylah Darji
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Azhar Ahmad
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zairossani Mohd Nor
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Christine Sue Chen Lee.

Ethics declarations

Ethical approval

This research study was carried out in compliance with the ethical standards and the authors declare that we do not have any commercial or associated interest that represents a conflict of interest in connection with the work submitted.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Appendix A (DOCX 405 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lee, C.S.C., Singh, M., Teh, CH. et al. Modification of quebrachitol extracted from natural rubber serum (NRS) to l-chiro-inositol for pharmaceutical and nutraceutical applications. J Rubber Res 26, 179–192 (2023). https://doi.org/10.1007/s42464-023-00218-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s42464-023-00218-2

Keywords

Search

Navigation