Hydrochloric acid producing higher purity of glucosamine than sulfuric acid: a comparison study with different detection approaches

1. Jain, T., Kumar, H. & Dutta, P.K. (2016). D-Glucosamine and N-Acetyl D-Glucosamine: Their Potential Use as Regenerative Medicine. In P. K. Dutta (Ed.), Chitin and Chitosan for Regenerative Medicine (pp. 279–295). Springer. Search in Google Scholar

2. Sampoorna, M., Mahender, M. & Bhavani, S.V. (2020). ORTHOLORD TABLETS: A Blend of Natural Ingredients Provides Nutritional Support for Joint Health. Asian J. Appl. Sci. Technol. 4(2), 17–36. DOI: 10.38177/AJAST.2020.4204. Search in Google Scholar

3. Kantor, E.D., Lampe, J.W., Navarro, S.L., Song, X., Milne, G.L. & White, E. (2014). Associations between glucosamine and chondroitin supplement use and biomarkers of systemic inflammation. J. Altern. Complement. Med. 20(6), 479–485. DOI: 10.1089/acm.2013.0323. Search in Google Scholar

4. Wu, S., Dai, X., Shilong, F., Zhu, M., Shen, X., Zhang, K. & Li, S. (2018). Antimicrobial and antioxidant capacity of glucosamine-zinc (II) complex via non-enzymatic browning reaction. Food Sci. Biotechnol. 27(1), 1–7. DOI: 10.1007/s10068-017-0192-1. Search in Google Scholar

5. Shekhar, S., Sharma, R., Sharma, S., Sharma, B., Sarkar, A. & Jain, P. (2020). An exploration of electrocatalytic analysis and antibacterial efficacy of electrically conductive poly (D-glucosamine)/graphene oxide bionanohybrid. Carbohydr. Polym. 240, 1–13. DOI: 10.1016/j.carbpol.2020.116242. Search in Google Scholar

6. Chesnokov, V., Gong, B., Sun, C. & Itakura, K. (2014). Anti-cancer activity of glucosamine through inhibition of N-linked glycosylation. Cancer Cell Int. 14(1), 1–10. DOI: 10.1186/1475-2867-14-45. Search in Google Scholar

7. Saengnipanthkul, S., Waikakul, S., Rojanasthien, S., Totemchokchyakarn, K., Srinkapaibulaya, A., Cheh Chin, T., Mai Hong, N., Bruyère, O., Cooper, C. & Reginster, J.Y. (2019). Differentiation of patented crystalline glucosamine sulfate from other glucosamine preparations will optimize osteoarthritis treatment. Int. J. Rheum. Dis., 22(3), 376–385. DOI: 10.1111/1756-185X.13068. Search in Google Scholar

8. Zahedipour, F., Dalirfardouei, R., Karimi, G. & Jamialahmadi, K. (2017). Molecular mechanisms of anticancer effects of Glucosamine. Biomed. Pharmacother. 95, 1051–1058. DOI: 10.1016/j.biopha.2017.08.122. Search in Google Scholar

9. Towheed, T., Maxwell, L., Anastassiades, T.P., Shea, B., Houpt, J., Welch, V., Hochberg, M.C. & Wells, G.A. (2005). Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst. Rev. (2), 1–58. DOI: 10.1002/14651858.CD002946.pub2. Search in Google Scholar

10. Altman, R.D. (2009). Glucosamine therapy for knee osteoarthritis: pharmacokinetic considerations. Expert Rev. Clin. Pharmacol. 2(4), 359–371. DOI: 10.1586/ecp.09.17. Search in Google Scholar

11. Amarase, C., Tanavalee, A., Jumroonwong, W., Tanavalee, C., Tantavisut, S. & Ngarmukos, S. (2018). Patients’ Real Life Experience in Using Glucosamine Sulfate for Treatment of Knee Osteoarthritis Under The Comptroller General’s Department (CGD) Reimbursement Protocol: A Preliminary Report. J. Med. Assoc. Thai., 101(3), 223–230. Search in Google Scholar

12. Meulyzer, M., Vachon, P., Beaudry, F., Vinardell, T., Richard, H., Beauchamp, G. & Laverty, S. (2008). Comparison of pharmacokinetics of glucosamine and synovial fluid levels following administration of glucosamine sulphate or glucosa-mine hydrochloride. Osteoarthr. Cartil. 16(9), 973–979. DOI: 10.1016/j.joca.2008.01.006. Search in Google Scholar

13. Bruyere, O., Pavelka, K., Rovati, L.C., Deroisy, R., Olejarova, M., Gatterova, J., Giacovelli, G. & Reginster, J.-Y. (2004). Glucosamine sulfate reduces osteoarthritis progression in postmenopausal women with knee osteoarthritis: evidence from two 3-year studies. Menopause, 11(2), 138–143. DOI: 10.1097/01.gme.0000087983.28957.5d. Search in Google Scholar

14. Tenti, S., Giordano, N., Mondanelli, N., Giannotti, S., Maheu, E. & Fioravanti, A. (2020). A retrospective observational study of glucosamine sulfate in addition to conventional therapy in hand osteoarthritis patients compared to conventional treatment alone. Aging. Clin. Exp. Res., 32, 1161–1172. DOI: 10.1007/s40520-019-01305-4. Search in Google Scholar

15. Veronese, N., Ecarnot, F., Cheleschi, S., Fioravanti, A. & Maggi, S. (2022). Possible synergic action of non-steroidal anti-inflammatory drugs and glucosamine sulfate for the treatment of knee osteoarthritis: a scoping review. BMC Musculoskelet. Disord. 23(1), 1–9. DOI: 10.1186/s12891-022-06046-6. Search in Google Scholar

16. Mojarrad, J.S., Nemati, M., Valizadeh, H., Ansarin, M. & Bourbour, S. (2007). Preparation of Glucosamine from Exoskeleton of Shrimp and Predicting Production Yield by Response Surface Methodology. J. Agric. Food Chem. 55, 2246–2250. DOI: 10.1021/jf062983a. Search in Google Scholar

17. Elieh Ali Komi, D., Sharma, L. & Dela Cruz, C.S. (2018). Chitin and its effects on inflammatory and immune responses. Clin. Rev. Allergy Immunol. 54(2), 213–223. DOI: 10.1007/s12016-017-8600-0. Search in Google Scholar

18. Novikov, V.Y. (2004). Acid Hydrolysis of Chitin and Chitosan. Russ. J. Appl. Chem. 77(3), 484–487. DOI: 10.1023/B:RJAC.0000031297.24742.b9. Search in Google Scholar

19. Rojas, J., Madrigal, J. & Ortiz, J. (2015). Effect of Acid Hydrolysis on Tableting Properties of Chitin Obtained from Shrimp Heads. Trop. J. Pharm. Res., 14(7), 1137–1144. DOI: 10.4314/tjpr.v14i7.3. Search in Google Scholar

20. Munjal, S. & Singh, A. (2020). The Arrhenius Acid and Base Theory. In S. Ambrish (Ed.), Corrosion. IntechOpen. Search in Google Scholar

21. Lin, Y. (2023). Whole-process optimization for industrial production of glucosamine sulfate sodium chloride based on QbD concept. Chin. J. Chem. Eng. 54, 153–161. DOI: 10.1016/j.cjche.2022.03.025. Search in Google Scholar

22. Ramırez, M.G., Avelizapa, L.R., Avelizapa, N.R. & Camarillo, R.C. (2004). Colloidal chitin stained with Remazol Brilliant Blue R®, a useful substrate to select chitinolytic microorganisms and to evaluate chitinases. J. Microbiol. Methods, 56(2), 213–219. DOI: 10.1016/j.mimet.2003.10.011. Search in Google Scholar

23. Swartz, M. (2010). HPLC detectors: a brief review. J. Liq. Chromatogr. Relat. Technol. 33(9–12), 1130–1150. DOI: 10.1080/10826076.2010.484356. Search in Google Scholar

24. Yan, X. (2014). High performance liquid chromatography for carbohydrate analysis. In Z. Yuegang (Ed.), High-Performance Liquid Chromatography (HPLC): Principles, Practices and Procedures (pp. 1–20). Nova Science. Search in Google Scholar

25. Fish Information & Services. (2018). Shrimp exporters face prons and cons this year. https://seafood.media/fis/worldnews/worldnews.asp?l=e&id=100412&ndb=1 Search in Google Scholar

26. Sowcharoensuk, C. (2019). Industry Outlook 2019–2021: Processed Seafood. Krungsri Research. Retrieved June 27, 2022, from https://www.krungsri.com/en/research/industry/industry-outlook/Food-Beverage/Processed-Seafood/IO/io-frocessed-seafood-20-th Search in Google Scholar

27. Bassig, R.A., Obinque, A.V., Nebres, V.T., Delos Santos, V.H., Peralta, D.M. & Madrid, A.J.J. (2022). Black tiger shrimp processing waste can be converted into a value-added powder. Responsible Seafood Advocate. Retrieved June 27, 2022, from https://www.globalseafood.org/advocate/black-tiger-shrimp-processing-waste-can-be-converted-into-a-value-added-powder/. Search in Google Scholar

28. Benavente, M., Arias, S., Moreno, L. & Martínez, J. (2015). Production of glucosamine hydrochloride from crustacean shell. J. Pharm. Pharmacol. 3(1), 20–26. DOI: 10.17265/2328-2150/2015.01.003. Search in Google Scholar

29. Miller, G.L. (1959). Use of dinitrosalicylic acid reagent for determination of reducing sugar. Anal. Chem. 31(3), 426–428. DOI: 10.1021/ac60147a030. Search in Google Scholar

30. Magaña, A.A., Wrobel, K., Escobosa, A.R.C. & Wrobel, K. (2014). Fast determination of glucosamine in pharmaceutical formulations by high performance liquid chromatography without pre-column derivatization. Acta Univ. 24(2), 16–22. DOI: 10.15174/au.2014.717. Search in Google Scholar

31. Donzelli, B.G.G., Ostroff, G. & Harman, G.E. (2003). Enhanced enzymatic hydrolysis of langostino shell chitin with mixtures of enzymes from bacterial and fungal sources. Carbohydr. Res. 338(18), 1823–1833. DOI: 10.1016/S0008-6215(03)00269-6. Search in Google Scholar

32. Chang, H., Chen, Y. & Tan, F. (2011). Antioxidative properties of a chitosan–glucose Maillard reaction product and its effect on pork qualities during refrigerated storage. Food Chem., 124(2), 589–595. DOI: 10.1016/j.foodchem.2010.06.080. Search in Google Scholar

33. Choi, Y.J., & Shin, Y.C. (2000). Microbial enzymes for the production of glucosamine and N-acetylglucosamine from chitinous biomass. Proceedings of the Korean Society for Applied Microbiology Conference. Search in Google Scholar

34. Gandhi, N. & Laidler, J.K. (2002). Preparation of glucosamine hydrochloride. In Alberta Research Council Inc. (Ed.). Washington, DC, USA: United States patent US 6,486,307. Search in Google Scholar

35. Martin Xavier, K. & Ramachandran, K. (2006). Standardization of Optimum Conditions for the Production of Glucosamine Hydrochiloride from Chitin Central Institute of Fisheries Technology]. Search in Google Scholar

36. Zhang, P. & Sutheerawattananonda, M. (2020). Kinetic models for glucosamine production by acid hydrolysis of chitin in five mushrooms. Int. J. Chem. Eng., 2020, 1-8. DOI: 10.1155/2020/5084036. Search in Google Scholar

37. Shī, X.W., Shī, M., Wú, M.Y. & Shī, L.K. (2014). Glucosamine sulfate production method. In L. Yangzhou Rixing Bio-Tech Co. (Ed.). China: CN103509063A. Search in Google Scholar

38. Hu, R., Lin, L., Liu, T., Ouyang, P., He, B., & Liu, S. (2008). Reducing sugar content in hemicellulose hydrolysate by DNS method: a revisit. J. Biobased Mater. Bio. 2(2), 156–161. DOI: 10.1166/jbmb.2008.306. Search in Google Scholar

39. Jain, A., Jain, R. & Jain, S. (2020). Quantitative Analysis of Reducing Sugars by 3, 5-Dinitrosalicylic Acid (DNSA Method). In Basic Techniques in Biochemistry, Microbiology and Molecular Biology: Principles and Techniques (pp. 181–183). DOI: 10.1007/978-1-4939-9861-6_43. Search in Google Scholar

40. Rivers, D.B., Gracheck, S.J., Woodford, L.C. & Emert, G.H. (1984). Limitations of the NNS assay for reducing sugars from saccharified lignocellulosics [Trichoderma reesei]. Biotechnol. Bioeng. 26(7), 800–802. DOI: 10.1002/bit.260260727. Search in Google Scholar

41. Tihomirova, K., Dalecka, B. & Mezule, L. (2016). Application of conventional HPLC RI technique for sugar analysis in hydrolysed hay. Agron. Res. 14(5), 1713–1719. Search in Google Scholar

42. Deshavath, N.N., Mukherjee, G., Goud, V.V., Veeranki, V.D. & Sastri, C.V. (2020). Pitfalls in the 3, 5-dinitrosalicylic acid (DNS) assay for the reducing sugars: Interference of furfural and 5-hydroxymethylfurfural. Int. J. Biol. Macromol. 156, 180–185. DOI: 10.1016/j.ijbiomac.2020.04.045. Search in Google Scholar

43. Kazakevich, Y., McBrien, M. & LoBrutto, R. (2007). Computer-Assisted HPLC and Knowledge Management. In HPLC for Pharmaceutical Scientists (pp. 503–532). John Wiley & Sons. DOI: 10.1002/9780470087954.ch10. Search in Google Scholar

44. Schwald, W., Chan, M., Breuil, C. & Saddler, J. (1988). Comparison of HPLC and colorimetric methods for measuring cellulolytic activity. Appl. Microbiol. Biotechnol., 28, 398–403. DOI: 10.1007/BF00268203. Search in Google Scholar

45. Hasnaoui, N., Jbir, R., Mars, M., Trifi, M., Kamal-Eldin, A., Melgarejo, P. & Hernandez, F. (2011). Organic acids, sugars, and anthocyanins contents in juices of Tunisian pomegranate fruits. Int. J. Food Prop. 14(4), 741–757. DOI: 10.1080/10942910903383438. Search in Google Scholar

46. Sims, A. (1995). HPLC analysis of sugars in foods containing salt. J. Agric. Food Chem., 43(2), 377–380. DOI: 10.1021/jf00050a022. Search in Google Scholar

47. Holc, D., Pruss, A. & Komorowska-Kaufman, M. (2018). The possibility of using UV absorbance measurements to interpret the results of organic matter removal in the biofiltration process. Rocz. Ochr. Śr. 20, 326–341. Search in Google Scholar

48. Uchiho, Y., Goto, Y., Kamahori, M., Aota, T., Morisaki, A., Hosen, Y. & Koda, K. (2015). Far-ultraviolet absorbance detection of sugars and peptides by high-performance liquid chromatography. J. Chromatogr. A, 1424, 86–91. DOI: 10.1016/j.chroma.2015.11.006. Search in Google Scholar

49. Jalaludin, I. & Kim, J. (2021). Comparison of ultra-violet and refractive index detections in the HPLC analysis of sugars. Food Chem. 365(130514), 1–8. DOI: 10.1016/j.foodchem.2021.130514. Search in Google Scholar

50. Aghazadeh-Habashi, A., Sattari, S., Pasutto, F. & Jamali, F. (2002). High performance liquid chromatographic determination of glucosamine in rat plasma. J. Pharm. Sci. 5(2), 176–180. Search in Google Scholar

51. Kosman, V., Karlina, M., Pozharitskaya, O., Shikov, A. & Makarov, V. (2017). HPLC determination of glucosamine hydrochloride and chondroitin sulfate, weakly absorbing in the near UV region, in various buffer media. J. Anal. Chem. 72(8), 879–885. DOI: 10.1134/S106193481708007X. Search in Google Scholar

52. Russell, A.S., Aghazadeh-Habashi, A. & Jamali, F. (2002). Active ingredient consistency of commercially available glucosamine sulfate products. J. Rheumatol. 29(11), 2407–2409. Search in Google Scholar

53. El-Saharty, Y.S. & Bary, A.A. (2002). High-performance liquid chromatographic determination of neutraceuticals, glucosamine sulphate and chitosan, in raw materials and dosage forms. Anal. Chim. Acta, 462(1), 125–131. DOI: 10.1016/S0003-2670(02)00279-9. Search in Google Scholar

54. Mohammadi, M., Zamani, A. & Karimi, K. (2012). Determination of glucosamine in fungal cell walls by high-performance liquid chromatography (HPLC). J. Agric. Food Chem., 60(42), 10511–10515. DOI: 10.1021/jf303488w. Search in Google Scholar

55. Way, W.K., Gibson, K.G. & Breite, A.G. (2000). Determination of glucosamine in nutritional supplements by reversed-phase ion-pairing HPLC. J. Liq. Chromatogr. Related. Technol. 23(18), 2861–2871. DOI: 10.1081/JLC-100101238. Search in Google Scholar

56. Shao, Y., Alluri, R., Mummert, M., Koetter, U. & Lech, S. (2004). A stability-indicating HPLC method for the determination of glucosamine in pharmaceutical formulations. J. Pharm. Biomed. Anal. 35(3), 625–631. DOI: 10.1016/j.jpba.2004.01.021. Search in Google Scholar

57. Bertuzzi, D.L., Becher, T.B., Capreti, N.M., Amorim, J., Jurberg, I.D., Megiatto Jr, J.D. & Ornelas, C. (2018). General Protocol to Obtain D-Glucosamine from Biomass Residues: Shrimp Shells, Cicada Sloughs and Cockroaches. Global Chall. 2(11), 1–6. DOI: 10.1002/gch2.201800046. Search in Google Scholar

58. Novikov, V.Y. & Ivanov, A. (1997). Synthesis of D (+)-glucosamine hydrochloride. Russ. J. Appl. Chem., 70(9), 1467–1470. Search in Google Scholar

59. Smets, R. & Van Der Borght, M. (2021). Enhancing the specificity of chitin determinations through glucosamine analysis via ultra-performance LC-MS. Anal. Bioanal. Chem. 413, 3119–3130. DOI: 10.1007/s00216-021-03252-4. Search in Google Scholar

60. Putri, A.K., Kartosentono, S. & Sugijanto, N.E.N. (2019). Isolation of glucosamine hcl from scylla paramamosain and determination by HPLC. J. Teknol. 81(5), 1–8. DOI: 10.11113/jt.v81.13416. Search in Google Scholar

61. Islam, M., Masum, S., Rahman, M. & Shaikh, A. (2011). Preparation of glucosamine hydrochloride from indigenous shrimp processing waste. Bangladesh J. Sci. Ind. Res., 46(3), 375–378. DOI: 10.3329/bjsir.v46i3.9046. Search in Google Scholar

62. Akpuaka, M.U. & Esimai, B.G. (2021). Isolation and Characterization of Chitin and Chitosan from the Biomass of Nigerian Shrimp Shells and Conversion to Glucosamine. Int. J. Res. Sci. Eng. 2(7), 181–187. https://www.journals.grdpublications.com/index.php/ijprse/article/view/347. Search in Google Scholar

63. Padman, A.J., Henderson, J., Hodgson, S. & Rahman, P.K. (2014). Biomediated synthesis of silver nanoparticles using Exiguobacterium mexicanum. Biotechnol. Lett. 36, 2079–2084. DOI: 10.1007/s10529-014-1579-1. Search in Google Scholar

64. Chen, X., Liu, Y., Kerton, F. M. & Yan, N. (2015). Conversion of chitin and N-acetyl-d-glucosamine into a N-containing furan derivative in ionic liquids. Rsc Adv. 5(26), 20073–20080. DOI: 10.1039/C5RA00382B. Search in Google Scholar

65. Telange, D.R., Bhagat, S.B., Patil, A.T., Umekar, M.J., Pethe, A.M., Raut, N.A. & Dave, V. S. (2019). Glucosamine HCl-based solid dispersions to enhance the biopharmaceutical properties of acyclovir. J. Excip. Food Chem. 10(3), 65–81. Search in Google Scholar

66. Sun, X.-F., Sun, R., Fowler, P. & Baird, M. S. (2005). Extraction and characterization of original lignin and hemicelluloses from wheat straw. J. Agric. Food Chem. 53(4), 860–870. DOI: 10.1021/jf040456q. Search in Google Scholar

67. Yu, S., Zang, H., Chen, S., Jiang, Y., Yan, B. & Cheng, B. (2016). Efficient conversion of chitin biomass into 5-hydroxymethylfurfural over metal salts catalysts in dimethyl sulfoxide-water mixture under hydrothermal conditions. Polym. Degrad. Stab., 134, 105–114. DOI: 10.1016/j.polymdegradstab.2016.09.035. Search in Google Scholar

68. Sibi, G., Dhananjaya, K., Ravikumar, K., Mallesha, H., Venkatesha, R., Dwijendra, T., Bhusal, K., Gowda, N. & Gowda, K. (2013). Preparation of glucosamine hydrochloride from crustacean shell waste and it’s quantitation by RP-HPLC. Am. Eurasian. J. Sci. Res. 8(2), 63–67. DOI: 10.5829/idosi.aejsr.2013.8.2.7381. Search in Google Scholar