NMR Spectral Analysis and Hydrolysis Studies of Rebaudioside N, a Minor Steviol Glycoside of Stevia rebaudiana Bertoni

Venkata Sai Prakash Chaturvedula, Steven Chen, Oliver Yu, Guohong Mao

Natural Ingredient Development, Blue California, Rancho Santa Margarita, USA.
Natural Ingredient Development, Blue California, Rancho Santa Margarita, USA..

DOI: 10.4236/fns.2013.410130                

Abstract

The complete proton and carbon NMR spectral assignments of a diterpene glycoside isolated from the commercial extract of the leaves of Stevia rebaudiana Bertoni, 13-[(2-O-β-D-glucopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] entkaur-16-en-19-oic acid-[(2-O-α-L-rhamnopyranosyl-3-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester] (1); also known as rebaudioside N, was achieved by the extensive 1D and 2D NMR (1H and 13C, COSY, HMQC, HMBC) as well as mass spectral data. Further, hydrolysis studies were performed on rebaudioside N using acid and enzymatic studies to identify aglycone and sugar residues in its structure.

Keywords

Stevia rebaudiana; Diterpene Glycoside; Isolation; Structure Elucidation; Spectral Data; Hydrolysis Studies

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. E. Mosettig and W. R. Nes, “Stevioside. II. The Structure of the Aglucon,” Journal of Organic Chemistry, Vol. 20, No. 7, 1955, pp. 884-899. http://dx.doi.org/10.1021/jo01125a013
[2]	S. E. Mosettig, U. Beglinger, F. Dolder, H. Lichiti, P. Quitt and J. A. Waters, “The Absolute Configuration of Steviol and Isosteviol,” Journal of American Chemical Society, Vol. 85, No. 11, 1963, p. 2305. http://dx.doi.org/10.1021/ja00898a025
[3]	J. E. Brandle, A. N. Starrratt and M. Gijen, “Stevia rebaudiana: Its Agricultural, Biological and Chemical Properties,” Canadian Journal of Plant Sciences, Vol. 78, No. 4, 1998, pp. 527-536. http://dx.doi.org/ 10.4141/P97-114
[4]	E. S. Wayne and L. Lin, “NMR Studies of the Conformation of the Natural Sweetener Rebaudioside A,” Carbohydrate Research, Vol. 344, No. 18, 2009, pp. 2533-2538. http://dx.doi.org/10.1016/j. carres.2009.10.005
[5]	M. Ohta, S. Sasa, A. Inoue, T. Tamai, I. Fujita, K. Morita and F. Matsuura, “Characterization of Novel Steviol Glycosides from Leaves of Stevia rebaudiana Morita,” Journal of Applied Glycoscience, Vol. 57, No. 3, 2010, pp. 199-209. http://dx.doi.org/10.5458/jag.57.199
[6]	E. Bedir, N. J. Toyang, I. A. Khan, L. A. Walker and A. M. Clark, “A New Dammarane Type Triterpene Glycoside from Polyscias fulva,” Journal of Natural Products, Vol. 64, No. 1, 2001, pp. 95-97. http://dx.doi.org/10.1021/np0003589
[7]	V. S. P. Chaturvedula, J. K. Schilling, J. S. Miller, R. Andriantsiferana, V. E. Rasamison and V. D. G. I. Kingston, “New Cytotoxic Oleanane Saponins from the Infructescences of Polyscias amplifolia from the Madagascar Rainforest,” Planta Medica, Vol. 69, 2003, pp. 440-444. http://dx.doi.org/10.1055/s-2003-39711
[8]	V. D. Huan, S. Yamamura, K. Ohtani, R. Kasai, K. Yamasaki and N. T. Nham, “Oleanane saponins from Polyscias fructicosa,” Phytochemistry, Vol. 47, No. 3, 1998, pp. 451-457. http://dx.doi.org/10.1016/ S0031-9422(97)00618-3
[9]	K. Ohtani, Y. Aikawa, R. Kasai, W. Chou, K. Yamasaki and O. Tanaka, “Minor Diterpene Glycosides from Sweet Leaves of Rubus suavissimus,” Phytochemistry, Vol. 31, No. 5, 1992, pp. 1553-1559. http://dx.doi.org/10.1016/0031-9422(92)83105-8
[10]	V. S. P. Chaturvedula and I. Prakash, “A New Diterpenoid Glycoside from Stevia rebaudiana,” Molecules, Vol. 16, No. 4, 2011, pp. 2937-2943. http://dx.doi.org/10.3390/molecules16042937
[11]	V. S. P. Chaturvedula and I. Prakash, “Structures of the Novel Diterpene Glycosides from Stevia rebaudiana,” Carbohydrate Research, Vol. 346, No. 8, 2011, pp. 1057-1060. http://dx.doi.org/10.1016/ j.carres.2011.03.025
[12]	V. S. P. Chaturvedula and I. Prakash, “Additional Minor Diterpene Glycosides from Stevia rebaudiana,” Natural Product Communications, Vol. 6, No. 8, 2011, pp. 1059-1062.