Skip to main content
Log in

Identification of a novel sugar compound from Korean pine seeds

  • Research Note
  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

Sugar derivatives are critically important in nutritional, pharmaceutical, and some non-food industries. Amino sugars are more important as essential components of many drugs, antibiotics, and biopolymers. Hence, a novel amino sugar compound is worthy of investigation for identification and production. A novel amino sugar compound was identified from crude extracts of Korean pine seed embryos. This new compound was isolated from extracts using traditional purification steps. The pure compound was white in color with a melting point of 145°C. HPLC, TLC, FT-IR, and NMR analyses of the compound indicated a trisaccharide form of amino mannose that was polymerized with β-(1→2) glycosidic bonding. Computer-aided NMR spectral analysis of the trisaccharide of 2-dehydro-2-mannosamine exhibited a 96% match with the 13C-NMR spectrum of the new compound.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Marchal LM, Beeftink HH, Tramper J. Towards a rational design of commercial maltodextrins. Trends Food Sci. Tech. 10: 345–355 (1999)

    Article  CAS  Google Scholar 

  2. Imeson A. Thickening and Gelling Agents for Food. 3rd ed. Blackie Academic and Professional, London, UK. pp. 15–17 (1996)

    Google Scholar 

  3. Sanford PA. A survey of possible new polysaccharides. pp. 251–262. In: Polysaccharides in Food. Blanshard JMV, Mitchell JR (eds). Butterworths, London, UK. (1979)

    Chapter  Google Scholar 

  4. Edwards CA. The physiological effects of dietary fiber. pp. 58–71. In: Dietary Fiber in Health and Disease. Kritchevsky D, Bonfield C (eds). Eagan Press, St. Paul, MN, USA (1995)

    Google Scholar 

  5. Inngjerdingen KT, Debes SC, Inngjerdingen M, Hokputsa S, Harding SE, Rolstad B. Bioactive pectic polysaccharides from Glinus oppositifolius (L.) Aug. DC., a Malian medicinal plant, isolation and partial characterization. J. Ethnopharmacol. 101: 204–214 (2005)

    Article  CAS  Google Scholar 

  6. Sun Y, Tang J, Gu X, Li D. Water soluble polysaccharides from Angelica sinensis (Oliv.) Diels: Preparation, characterization and bioactivity. Int. J. Biol. Macromol. 36: 283–289 (2005)

    Article  CAS  Google Scholar 

  7. Park JK, Khan T, Jung JY. Structural studies of the glucoronic acid oligomers produced by Gluconacetobacter hansenii strain. Carbohyd. Polym. 63: 482–486 (2006)

    Article  CAS  Google Scholar 

  8. Saenz C, Sepulveda E, Matsuhiro B. Opuntia spp. Mucilage’s: A functional component with industrial perspectives. J. Arid Environ. 57: 275–290 (2004)

    Google Scholar 

  9. Ji XM. Mo J, Liu HM, Sun HP. Synthesis of new amino sugar derivatives from keto-sugars of D-xylose. Carbohyd. Res. 341: 2312–2320 (2006)

    Article  CAS  Google Scholar 

  10. Soro P, Rassu G, Spanu P, Pianna L, Zanardi F, Casiraghi G. Total syntheses of 2,4-diamino-2-4-dideoxy-L-arabinose and 2,4-diamino-2,4-dideoxy-L-ribose. J. Org. Chem. 61: 5172–5174 (1996)

    Article  CAS  Google Scholar 

  11. Voss AA, Diez-Sampedro A, Hirayama BA, Donald Loo DDF, Wright EM. Imino sugars are potent agonists of the human glucose sensor SGLT3. Mol. Pharmacol. 71: 628–634 (2007)

    Article  CAS  Google Scholar 

  12. Butters TD, Dwek RA, Platt FM. Imino sugars inhibitors for treating the lysosomal glycosphingolipidoses. Glycobiology 10: 622–627 (2005)

    Google Scholar 

  13. Angelino NJ, Bernacki RJ, Sharma M, Dodson-Simmons O, Korytnyk W. Versatile intermediates in the selective modification of the aminofunction of 2-amino-2-deoxy-D-mannopyranose and the 3-postion of 2-acetamido-2-deoxy-D-mannose: potential membrane modifiers in neoplastic control. Carbohyd. Res. 276: 99–115 (1995)

    Article  CAS  Google Scholar 

  14. Hitti M. Pine nut oil may cut appetite. Available from: http://www.medicinenet. com/script/main/art.asp?articlekey=60784. Accessed Oct. 15, 2006.

    Google Scholar 

  15. Miller GN. Use of dinitrosalicylic acid reagent for the determination of reducing sugar. Anal. Chem. 81: 426–428 (1959)

    Article  Google Scholar 

  16. University of Calgary. Organic Laboratory Techniques 4. Available from: http://www.chem.ucalgary.ca/courses/351/laboratory/meltingpoint.pdf. Accessed Jul. 13, 2015.

  17. Coimbra MA, Barros A, Barros M, Rutledge DN, Delgadillo I. Multivariate analysis of uronic acid and neutral sugars in whole pectic samples by FT-IR spectroscopy. Carbohyd. Polym. 37: 241–248 (1998)

    Article  CAS  Google Scholar 

  18. Santhiya D, Subramanian S, Natarajan KA. Surface chemical studies on sphalerite and galena using extracellular polysaccharide isolated from Bacillus polymyxa. J. Colloid. Interf. Sci. 256: 237–248 (2002)

    Article  CAS  Google Scholar 

  19. Shi Y, Sheng J, Yang F, Hu Q. Purification and identification of polysaccharide derived from Chlorella pyrenoidosa. Food Chem. 103: 101–105 (2007)

    Article  CAS  Google Scholar 

  20. Gi YK, Hyung SP, Byong HN, Sang JL, Jae DL. Purification and characterization of acidic proteo-heteroglycan from the fruiting body of Phellinus linteus. Bioresour. Technol. 89: 81–87 (2003)

    Article  Google Scholar 

  21. Wang L, Zhang H, Zhang X, Chen Z. Purification and identification of a novel heteropolysaccharide RBPS2a with anti-complementary activity from defatted rice bran. Food Chem. 110: 150–155 (2008)

    Article  CAS  Google Scholar 

  22. Xu F, Sun JX, Geng ZC, Liu CF, Ren JL, Sun RC, Fowler P, Baird MS. Comparative study of water-soluble and alkali-soluble hemicllulose from perennial ryegrass leaves (Lolium peree). Carbohyd. Polym. 67: 56–65 (2007)

    Article  CAS  Google Scholar 

  23. Zhao M, Yang N, Yang B, Jiang Y, Zhang G. Structural characterization of water-soluble polysaccharides from Opuntia monacantha cladodes in relation to their anti-glycated activities. Food Chem. 105: 1480–1486 (2007)

    Article  CAS  Google Scholar 

  24. Chaikumpollert O, Methacanon P, Suchiva K. Structural elucidation of hemicelluloses from vetiver grass. Carbohyd. Polym. 57: 191–196 (2004)

    Article  CAS  Google Scholar 

  25. Rao RSP, Muralikrishna G. Structural characteristics of water-soluble feruloyl arabinoxylans from rice (Oryza sativa) and ragi (finger millet, Eleusine coracana): Variations upon malting. Food Chem. 104: 1160–1170 (2007)

    Article  CAS  Google Scholar 

  26. Nie S, Xie M, Fu Z, Wan Y, Yan A. Study on the purification and chemical compositions of tea glycoprotein. Carbohyd. Polym. 71: 626–633 (2008)

    Article  CAS  Google Scholar 

  27. Gupta S, Madan RN, Bansal MC. Chemical composition of Pinus caribaea hemi-celluloses. Tappi J. 70: 113–114 (1987)

    CAS  Google Scholar 

  28. Chiovitti A, Bacic A, Craik DJ, Munro SLA, Kraft GT, Liao ML. Cell-wall polysaccharide from Australian red algae of the family Solieriaceae (Gigartinales, Rhodophyta): Novel, highly pyruvated carrageenans from the genus Callophycus. Carbohyd. Res. 299: 229–243 (1997)

    Article  CAS  Google Scholar 

  29. Ajisaka K, Matsuo I, Isomura M, Fujimoto H, Shirakabe M, Okawa M. Enzymatic synthesis of mannobioses and mannotrioses by reverse hydrolysis using alpha-mannosidase from Aspergillus niger. Carbohyd. Res. 270: 123–130 (1995)

    Article  CAS  Google Scholar 

  30. Vinogradov E, Li J, Sadovskaya I, Jabbouri S, Helander IM. The structure of the carbohydrate backbone of the lipopolysaccharide of Pectinatus frisingensis strain VTT E-79104. Carbohyd. Res. 339: 1637–1642 (2004)

    Article  CAS  Google Scholar 

  31. Urai M, Anzai H, Ogihara J, Iwabuchi N, Harayama S, Sunairi M, Nakajima M. Structural analysis of an extracellular polysaccharide produced by Rhodococcus rhodochrous strain S-2. Carbohyd. Res. 341: 766–775 (2006)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hak-Ryul Kim.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kalam Azad, M.A., Wang, F. & Kim, HR. Identification of a novel sugar compound from Korean pine seeds. Food Sci Biotechnol 24, 2011–2015 (2015). https://doi.org/10.1007/s10068-015-0265-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-015-0265-y

Keywords

Navigation