PRODUCTION OF D-SORBITOL AND L-ASCORBIC ACID FROM D-GLUCOSE: THEIR PROPERTIES, FIELDS OF USAGE AND EFFECTS ON HEALTH

Öz

D-sorbitol is a sugar alcohol naturally found in many fruits. L-ascorbic acid is a compound that can be synthesized by plants and some animals but must be externally taken by humans because it cannot be synthesized due to the lack of L-gulono-γ-lactone oxidase enzyme. D-sorbitol and L-ascorbic acid are two ingredients that are frequently used in the food, chemical, pharmaceutical and cosmetic industries and may have a number of positive effects on human health. These ingredients are generally produced commercially from D-glucose by a series of chemical and biochemical reactions. In the commercial production of these compounds, Reichstein-Grüssner or two-step fermentation methods are generally used. In this study; the properties, fields of usage, effects on human health and production methods of D-sorbitol and L-ascorbic acid are reviewed.

Anahtar Kelimeler

• D-glucose,hydrogenation,fermentation,Gluconobacter oxydans,Ketogulonicigenum vulgare

D-GLİKOZDAN D-SORBİTOL VE L-ASKORBİK ASİT ÜRETİMİ: BU BİLEŞİKLERİN ÖZELLİKLERİ, KULLANIM ALANLARI VE SAĞLIK ÜZERİNE ETKİLERİ

Öz

D-sorbitol birçok meyvede doğal olarak bulunan bir şeker alkolüdür. L-askorbik asit ise bitkiler ve bazı hayvanlar tarafından sentezlenebilen ancak insanlar tarafından L-gulono-γ-lakton oksidaz enzimi eksikliği nedeniyle sentezlenemediği için dışarıdan alınması zorunlu olan bir bileşiktir. D-sorbitol ve L-askorbik asit gıda, kimya, ilaç ve kozmetik sektörlerinde sıklıkla kullanılan ve insan sağlığı üzerine birçok olumlu etkileri bulunan iki üründür. Bu ürünler D-glikozdan kimyasal ve biyokimyasal reaksiyonlar ile ticari olarak üretilmektedirler. Bu bileşiklerin ticari üretiminde genellikle Reichstein-Grüssner veya iki aşamalı fermantasyon yöntemleri kullanılmaktadır. Bu çalışmada D-sorbitol ve L-askorbik asidin bazı özellikleri, kullanım alanları, sağlık üzerine etkileri ve üretim yöntemleri derlenmiştir.  

Anahtar Kelimeler

• D-glikoz,hidrojenizasyon,fermantasyon,Gluconobacter oxydans,Ketogulonicigenum vulgare

Kaynakça

1. Bhand, D.V., Patwardhan, A.V. (2015). Statistical optimization of L-ascorbic acid production by Xanthomonas campestris MTCC 2286 using sucrose as a cheap carbon source. J Biochem Technol, 6(1): 922-928.
2. Bommarius, A.S., Riebel-Bommarius, B.R. (2004). Biocatalysis: fundamentals and applications. Wiley-VCH Verlag GmbH & Co.KGaA, Weinheim, 611 pp.
3. Camarena, V., Wang, G. (2016). The epigenetic role of vitamin C in health and disease. Cell Mol Life Sci, 73(8): 1645-1658.
4. Canali, R., Natarelli, L., Leoni, G., Azzini, E., Comitato, R., Sancak, O., Barella, L., Virgili, F. (2014). Vitamin C supplementation modulates gene expression in peripheral blood mononuclear cells specifically upon an inflammatory stimulus: a pilot study in healthy subjects. Genes Nutr, 9(3): 390.
5. Covarrubias-Pinto, A., Acuña, A., Beltrán, F., Torres-Díaz, L., Castro, M. (2015). Old things new view: ascorbic acid protects the brain in neurodegenerative disorders. Int J Mol Sci, 16(12): 28194-28217.
6. Deis, R.C., Kearsley, M.W. (2012). Sorbitol and mannitol. Sweeteners and Sugar Alternatives in Food Technology (second edition), 331-346.
7. del Rocío Gómez-García, M., Ochoa-Alejo, N. (2016). Predominant role of the L-galactose pathway in L-ascorbic acid biosynthesis in fruits and leaves of the Capsicum annuum L. chili pepper. Braz J Bot, 39(1): 157-168.
8. Delić, V., Šunić, D., Vlašić, D. (1989). Microbial reactions for the synthesis of vitamin C (L-ascorbic acid). Biotechnology of vitamins, pigments and growth factors, Springer, 299-334.

9. Ding, M.Z., Zou, Y., Song, H., Yuan, Y.J. (2014). Metabolomic analysis of cooperative adaptation between co-cultured Bacillus cereus and Ketogulonicigenium vulgare. Plos One, 9(4): e94889.
10. Eitenmiller, R.R., Landen Jr, W., Ye, L. (2016). Vitamin analysis for the health and food sciences. CRC Press (second edition), 664 pp.
11. Fennema, O.R., Damodaran, S., Parkin, K.L. (2008). Fennema's food chemistry. CRC Press (fourth edition), 1160 pp.
12. García, B., Moreno, J., Iglesias, J., Melero, J.A., Morales, G. (2019). Transformation of glucose into sorbitol on raney nickel catalysts in the absence of molecular hydrogen: sugar disproportionation vs catalytic hydrogen transfer. Top Catal, 1-9.
13. Ge, X., Zhao, Y., Hou, W., Zhang, W., Chen, W., Wang, J., Zhao, N., Lin, J., Wang, W., Chen, M. (2013). Complete genome sequence of the industrial strain Gluconobacter oxydans H24. Genome Announcements, 1(1): e00003-00013.
14. Ghosh, S., Sudha, M. (2012). A review on polyols: new frontiers for health-based bakery products. Int J Food Sci Nutr, 63(3): 372-379.
15. Grembecka, M. (2015a). Natural sweeteners in a human diet. Roczniki Państwowego Zakładu Higieny, 66(3): 195-202.
16. Grembecka, M. (2015b). Sugar alcohols—their role in the modern world of sweeteners: a review. Eur Food Res Technol, 241(1): 1-14.
17. Guo, X., Wang, X., Guan, J., Chen, X., Qin, Z., Mu, X., Xian, M. (2014). Selective hydrogenation of D-glucose to D-sorbitol over Ru/ZSM-5 catalysts. Chinese J Catal, 35(5): 733-740.
18. Huang, M., Zhang, Y.H., Yao, S., Ma, D., Yu, X.D., Zhang, Q., Lyu, S.X. (2018). Antioxidant effect of glutathione on promoting 2‐keto‐l‐gulonic acid production in vitamin C fermentation system. J App Microbiol, 125(5): 1383-1395.
19. Jia, N., Ding, M.Z., Zou, Y., Gao F., Yuan, Y.J. (2017). Comparative genomics and metabolomics analyses of the adaptation mechanism in Ketogulonicigenium vulgare-Bacillus thuringiensis consortium. Sci Rep-UK, 7(46759):1-8.
20. Knight, J., Madduma-Liyanage, K., Mobley, J.A., Assimos, D.G., Holmes, R.P. (2016). Ascorbic acid intake and oxalate synthesis. Urolithiasis, 44(4): 289-297.
21. Kobayashi, H., Yamakoshi, Y., Hosaka, Y., Yabushita, M., Fukuoka, A. (2014). Production of sugar alcohols from real biomass by supported platinum catalyst. Catal Today, 226: 204-209.
22. Kowalczyk, D., Gustaw, W., Zięba, E., Lisiecki, S., Stadnik, J., Baraniak, B. (2016). Microstructure and functional properties of sorbitol-plasticized pea protein isolate emulsion films: Effect of lipid type and concentration. Food Hydrocolloids, 60: 353-363.
23. Lazaridis, P.A., Karakoulia, S., Delimitis, A., Coman, S.M., Parvulescu, V.I., Triantafyllidis, K.S. (2015). D-glucose hydrogenation/hydrogenolysis reactions on noble metal (Ru, Pt)/activated carbon supported catalysts. Catal Today, 257: 281-290.
24. Ma, Q., Zou, Y., Lv, Y., Song, H., Yuan, Y.J. (2014). Comparative proteomic analysis of experimental evolution of the Bacillus cereus-Ketogulonicigenium vulgare co-culture. Plos One, 9(3): e91789.
25. Ma, X., Qiao, C., Zhang, J., Xu, J. (2018). Effect of sorbitol content on microstructure and thermal properties of chitosan films. Int J Biol Macromol, 119: 1294-1297.
26. Mishra, D.K., Dabbawala, A.A., Park, J.J., Jhung, S.H., Hwang, J.S. (2014). Selective hydrogenation of D-glucose to D-sorbitol over HY zeolite supported ruthenium nanoparticles catalysts. Catal Today, 232: 99-107.
27. Murzin, D.Y., Duque, A., Arve, K., Sifontes, V., Aho, A., Eränen, K., Salmi, T. (2015). Catalytic hydrogenation of sugars. In Biomass Sugars for Non-Fuel Applications, 89-133.
28. Negahdar, L., Hausoul, P.J., Palkovits, S., Palkovits, R. (2015). Direct cleavage of sorbitol from oligosaccharides via a sequential hydrogenation-hydrolysis pathway. Appl Catal B: Environ, 166: 460-464.
29. Padayatty, S.J., Levine, M. (2016). Vitamin C: the known and the unknown and Goldilocks. Oral Dis, 22(6): 463-493.
30. Pappenberger, G., Hohmann, H.P. (2013). Industrial production of L-ascorbic acid (vitamin C) and D-isoascorbic acid. Biotech Food and Feed Adv, Springer, 143-188.
31. Robinson, J.M., Wadle, A.M., Reno, M.D., Kidd, R., Barrett Hinsz, S.R., Urquieta, J. (2015). Solvent-and microwave-assisted dehydrations of polyols to anhydro and dianhydro polyols. Energ Fuel, 29(10): 6529-6535.
32. Romero, A., Alonso, E., Sastre, Á., Nieto-Márquez, A. (2016). Conversion of biomass into sorbitol: cellulose hydrolysis on MCM-48 and d-glucose hydrogenation on Ru/MCM-48. Micropor Mesopor Mat, 224: 1-8.
33. Romero, A., Nieto-Márquez, A., Alonso, E. (2017). Bimetallic Ru: Ni/MCM-48 catalysts for the effective hydrogenation of D-glucose into sorbitol. Appl Catal A: Gen, 529: 49-59.
34. Sanyang, M.L., Sapuan, S.M., Jawaid, M., Ishak, M.R., Sahari, J. (2015). Effect of glycerol and sorbitol plasticizers on physical and thermal properties of sugar palm starch based films. In Proceedings of the 13th International Conference on Environment, Ecosystems and Development (EED ‘15), p. 157.
35. Sies, H. (2014). Role of metabolic H2O2 generation redox signaling and oxidative stress. J Biol Chem, 289(13): 8735-8741.
36. Sulman, E.M., Doluda, V.Y., Matveeva, V.G., Grigorev, M.E., Sulman, M.G., Bykov, A.V. (2016). Ru-containing catalysts in hydrogenation of D-glucose in flow-type microreactor. Chem Engineer Trans, 52: 673-678.
37. Sun, Z., Wang, R., Han, X., Xu, H., Yang, W. (2018). Enhanced 2-keto-L-gulonic acid production by applying L-sorbose-tolerant helper strain in the co-culture system. AMB Express, 8(1): 30.
38. Thomas, L.D., Elinder, C.G., Tiselius, H.G., Wolk, A., Åkesson, A. (2013). Ascorbic acid supplements and kidney stone incidence among men: a prospective study. JAMA Intern Med, 173(5): 386-388.
39. Vandamme, E.J. (2016). Industrial biotechnology of vitamins, biopigments, and antioxidants. Wiley-VCH Verlag GmbH & Co.KGaA, Weinheim, 578 pp.
40. Wang, S., Wei, W., Zhao, Y., Li, H., Li, H. (2015). Ru–B amorphous alloy deposited on mesoporous silica nanospheres: An efficient catalyst for D-glucose hydrogenation to D-sorbitol. Catal Today, 258: 327-336.
41. Wheeler, G., Ishikawa, T., Pornsaksit, V., Smirnoff, N. (2015). Evolution of alternative biosynthetic pathways for vitamin C following plastid acquisition in photosynthetic eukaryotes. Elife, 4: e06369.
42. Yamaguchi, A., Sato, O., Mimura, N., Shirai, M. (2016). Catalytic production of sugar alcohols from lignocellulosic biomass. Catal Today, 265: 199-202.
43. Yang, W., Han, L., Wang, Z., Xu, H. (2013). Two-helper-strain co-culture system: a novel method for enhancement of 2-keto-L-gulonic acid production. Biotechnol Lett, 35(11): 1853-1857.
44. Yang, W., Liu, C., Xu, H. (2015). l-sorbose is not only a substrate for 2-keto-l-gulonic acid production in the artificial microbial ecosystem of two strains mixed fermentation. J Ind Microbiol Biot, 42(6): 897-904.
45. Yang, W., Han, L., Mandlaa, M., Zhang, H., Zhang, Z., Xu, H. (2017). A plate method for rapid screening of Ketogulonicigenium vulgare mutants for enhanced 2-keto-L-gulonic acid production. Braz J Microbiol, 48(3): 397-402.
46. Ye, C., Wei Z., Nan X., Liming L. (2014). Metabolic model reconstruction and analysis of an artificial microbial ecosystem for vitamin C production. J Biotechnol, 182: 61-67.
47. Zada, B., Chen, M., Chen, C., Yan, L., Xu, Q., Li, W., Guo, Q., Fu, Y. (2017). Recent advances in catalytic production of sugar alcohols and their applications. Sci China Chem, 60(7): 853-869.
48. Zhang, J., Li, J.B., Wu, S.B., Liu, Y. (2013). Advances in the catalytic production and utilization of sorbitol. Ind Engineer Chem Res, 52(34): 11799-11815.
49. Zhang, J., Liu, J., Shi, Z., Liu, L., Chen, J. (2010). Manipulation of B. megaterium growth for efficient 2-KLG production by K. vulgare. Process Biochem, 45(4): 602-606.
50. Zhang, X., Durndell, L.J., Isaacs, M.A., Parlett, C.M., Lee, A.F., Wilson, K. (2016). Platinum-catalyzed aqueous-phase hydrogenation of D-glucose to D-sorbitol. ACS Catal, 6(11): 7409-7417.
51. Zhou, J., Du, G., Chen, J. (2012). Metabolic engineering of microorganisms for vitamin C production. Reprogramming Microbial Metabolic Pathways, Springer, 241-259.
52. Zou, W., Liu, L., Chen, J. (2013). Structure, mechanism and regulation of an artificial microbial ecosystem for vitamin C production. Cr Rev Microbiol, 39(3): 247-255.