Skip to main content
SpringerLink
Log in

Synthesis and characterization of novel amphiphilic tamarind seed xyloglucan-octenyl succinic anhydride conjugate

  • ORIGINAL PAPER
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

Octenyl succinic anhydride (OSA) has been widely reported for modification of starches and bears an amphiphilic character and is permitted for food applications. The present study was conducted to impart an amphiphilic character to tamarind seed xyloglucan (TSX) by its conjugation to OSA with an objective to impart amphiphilicity. The conjugate gains an amphiphilic character when hydrophilic groups of TSX bonded to hydrophobic octenyl groups. The TSX-OSA conjugate was characterized using Fourier Transform Infrared Spectroscopy (FTIR), Nuclear Magnetic Resonance (NMR), Thermal Gravimetric Analysis (TGA), and Scanning Electron Microscope (SEM). The FTIR, NMR results confirmed the conjugation of TSX-OSA. The TGA analysis revealed lower thermal stability of TSX-OSA conjugate due to introduction of hydrophobic OSA group thereby further confirming conjugation. The SEM micrograph shows that the conjugate possess a smoother surface in comparison to TSX. Hence, the conjugate can be envisaged as an improved material thereby expanding the applications of TSX in terms of its use in designing new products for drug delivery as well as for food applications.

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

Similar content being viewed by others

References

  1. Kochumalayil J, Sehaqui H, Zhou Q, Berglund LA (2010) Tamarind seed xyloglucan–a thermostable high-performance biopolymer from non-food feedstock. J Mater Chem 20(21):4321–4327

    Article  CAS  Google Scholar 

  2. Piqué N, Gómez-Guillén M, Montero M (2018) Xyloglucan, a plant polymer with barrier protective properties over the mucous membranes: an overview. Int J Mol Sci 19(3):673

    Article  Google Scholar 

  3. Sahoo R, Sahoo S (2015) Natural polymer of tamarind seed: a prospective carrier for ocular drug delivery. Eur Sci J ESJ 11(27)

  4. Balcı M, Allı A, Hazer B, Güven O, Cavicchi K, Cakmak M (2010) Synthesis and characterization of novel comb-type amphiphilic graft copolymers containing polypropylene and polyethylene glycol. Polym Bull 64(7):691–705

    Article  Google Scholar 

  5. Hazer B (2010) Amphiphilic poly (3-hydroxy alkanoate) s: potential candidates for medical applications. Int J Polym Sci 2010:1–8

    Article  Google Scholar 

  6. Ren L, Jiang M, Tong J, Bai X, Dong X, Zhou J (2010) Influence of surface esterification with alkenyl succinic anhydrides on mechanical properties of corn starch films. Carbohydr Polym 82(3):1010–1013

    Article  CAS  Google Scholar 

  7. Bai Y, Shi YC (2011a) Structure and preparation of octenyl succinic esters of granular starch, microporous starch and soluble maltodextrin. Carbohydr Polym 83(2):520–527

    Article  CAS  Google Scholar 

  8. Bai Y, Shi YC, Herrera A, Prakash O (2011b) Study of octenyl succinic anhydride-modified waxy maize starch by nuclear magnetic resonance spectroscopy. Carbohydr Polym 83(2):407–413

    Article  CAS  Google Scholar 

  9. Shi SS, He GQ (2012) Process optimization for cassava starch modified by octenyl succinic anhydride. Procedia Eng 37:255–259

    Article  CAS  Google Scholar 

  10. Segura-Campos M, Chel-Guerrero L, Betancur-Ancona D (2008) Synthesis and partial characterization of octenylsuccinic starch from Phaseolus lunatus. Food Hydrocoll 22:1467–1474

    Article  CAS  Google Scholar 

  11. Kweon DK, Choi JK, Kim EK, Lim ST (2001) Adsorption of divalent metal ions by succinylated and oxidized corn starches. Carbohydr Polym 46:171–177

    Article  CAS  Google Scholar 

  12. Dominguez A, Fernandez A, Gonzalez N, Igelesias E, Montenegro L (1997) Determination of critical micelle concentration of some surfactants by three techniques. J Chem Educ 74:1226–1230

    Article  Google Scholar 

  13. Glicksman MJ, Lillford PJ, Rowlands DW, Lang P, Dentini M, Crescenzi V, Edwards M, Fanutti C, Ried JSG (1991) Structure and solution properties of tamarind seed xyloglucan. Carbohydr Res 214:299–314

    Article  Google Scholar 

  14. Mishra A, Malhotra AV (2012) Graft copolymers of xyloglucan and methyl methacrylate. Carbohydr Polym 87(3):1899–1904

    Article  CAS  Google Scholar 

  15. Chang R, Yang J, Ge S, Zhao M, Liang C, Xiong L, Sun Q (2017) Synthesis and self-assembly of octenyl succinic anhydride modified short glucan chains based amphiphilic biopolymer: micelles, ultrasmall micelles, vesicles, and lutein encapsulation/release. Food Hydrocoll 67:14–26

    Article  CAS  Google Scholar 

  16. Altuna L, Herrera ML, Foresti ML (2018) Synthesis and characterization of octenyl succinic anhydride modified starches for food applications. A review of recent literature. Food Hydrocoll 80:97–110

    Article  CAS  Google Scholar 

  17. Simsek S, Ovando-Martinez M, Marefati A, Sjӧӧ M, Rayner M (2015) Chemical composition, digestibility and emulsification properties of octenyl succinic esters of various starches. Food Res Int 75:41–49

    Article  CAS  Google Scholar 

  18. Tizzotti MJ, Sweedman MC, Schäfer C, Gilbert RG (2013) The influence of macromolecular architecture on the critical aggregation concentration of large amphiphilic starch derivatives. Food Hydrocoll 31(2):365–374

    Article  CAS  Google Scholar 

  19. Whitney, K, Reuhs, B L, Martinez, M. O, & Simsek, S (2016) Analysis of octenylsuccinate rice and tapioca starches: distribution of octenylsuccinic anhydride groups in starch granules. Food Chem, 211: 608–615

  20. Mahajan HS, Sonar YA (2019) Esterification of pea starch with octenyl succinic anhydride using conventional and microwave irradiation method: synthesis and characterization. J Polym Res 26(10):247

    Article  CAS  Google Scholar 

  21. Hu Z, Feng T, Zeng X, Janaswamy S, Wang H, Campanella O (2019) Structural characterization and digestibility of Curcumin loaded Octenyl succinic nanoparticles. Nanomaterials 9(8):1073

    Article  CAS  Google Scholar 

  22. Mai Y, Eisenberg A (2012) Self-assembly of block copolymers. Chem Soc Rev 18:5969–5985

    Article  Google Scholar 

  23. Ogawa K, Hirai I, Shimasaki C, Yoshimura T, Ono S, Rengakuji S, Nakamura Y, Yamazaki I (1999) Simple determination method of degree of substitution for starch acetate. Bull Chem Soc Jpn 72(12):2785–2790

    Article  CAS  Google Scholar 

  24. Abdul Hadi N, Wiege B, Stabenau S, Marefati A, Rayner M (2020) Comparison of three methods to determine the degree of substitution of quinoa and rice starch acetates, propionates, and Butyrates: direct stoichiometry, FTIR, and 1H-NMR. Foods 83

Download references

Acknowledgements

Harmanmeet Kaur is highly thankful to Haryana State Government for C.V. Raman Fellowship. All the authors are also very grateful to Department of Science & Technology, Govt of India for providing assistance to establish research facilities.

Author information

Author notes

  1. Neeraj Dilbaghi and Munish Ahuja contributed equally to this work.

Authors and Affiliations

  1. Department of Bio & NanoTechnology, Guru Jambheshwar University of Science & Technology, Hisar, Haryana, 125001, India

    Neeraj Dilbaghi, Manju Bernela, Sandeep Kumar, Prashant Bhardwaj & Harmanmeet Kaur

  2. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science & Technology, Hisar, 125001, India

    Munish Ahuja

  3. Department of Biotechnology, Guru Nanak Dev University, Amritsar, Punjab, India

    Manju Bernela

  4. DHR-ICMR, Ministry of Health & Family Welfare, Government of India, New Delhi, India

    Harmanmeet Kaur

Authors
  1. Neeraj Dilbaghi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Munish Ahuja
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Manju Bernela
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sandeep Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Prashant Bhardwaj
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Harmanmeet Kaur
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Harmanmeet Kaur.

Additional information

Publisher’s note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dilbaghi, N., Ahuja, M., Bernela, M. et al. Synthesis and characterization of novel amphiphilic tamarind seed xyloglucan-octenyl succinic anhydride conjugate. J Polym Res 27, 236 (2020). https://doi.org/10.1007/s10965-020-02195-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-020-02195-1

Keywords

Search

Navigation