Isolation and Structural Characterization of a New Minor Penta β-D-Glucopyranosyl Diterpene from Stevia rebaudiana Bertoni

Venkata Sai Prakash Chaturvedula

Wisdom Natural Brands, Gilbert, AZ, USA.

DOI: 10.4236/ajps.2014.524368                

Abstract

From the commercial extract of the leaves of Stevia rebaudiana Bertoni, a new minor ent-kaurane diterpene glycoside having five β-D-glucopyranosyl units has been isolated. The chemical structure of the new compound was characterized as 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-(2-O-β-D-glucopyranosyl-6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester (1) on the basis of extensive 1D (¹H & ¹³C) and 2D NMR (TOCSY, HMQC, and HMBC), and High Resolution (HR) mass spectroscopic data as well as hydrolysis studies.

Keywords

Stevia rebaudiana, Compositae, Asteraceae, Diterpenoid Glycoside, Spectral Data, Hydrolysis Studies, Structure Characterization

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	Brandle, J.E., Starrratt, A.N. and Gijen, M. (1998) Stevia rebaudiana: Its Agricultural, Biological and Chemical Properties. Canadian Journal of Plant Sciences, 78, 527-536. http://dx.doi.org/10.4141/P97-114
[2]	Mosettig, S.E. and Nes, W.R. (1955) Stevioside. II. The Structure of the Aglucon. Journal of Organic Chemistry, 20, 884-899. http://dx.doi.org/10.1021/jo01125a013
[3]	Mosettig, S.E., Beglinger, U., Dolder, F., Lichiti, H., Quitt, P. and Waters, J.A. (1963) The Absolute Configuration of Steviol and Isosteviol. Journal of American Chemical Society, 85, 2305-2309. http://dx.doi.org/10.1021/ja00898a025
[4]	Chaturvedula, V.S.P. and Zamora, J. (2014) Reversed-Phase HPLC Analysis of Steviol Glycosides Isolated from Stevia rebaudiana Bertoni. Food and Nutrition Sciences, 5, 1711-1716. http://dx.doi.org/10.4236/fns.2014.517184
[5]	Chaturvedula, V.S.P. and Prakash, I. (2013) Structural Characterization and Hydrolysis Studies of Rebaudioside E, a Minor Sweet Component of Stevia rebaudiana. European Chemical Bulletin, 2, 298-302.
[6]	Prakash, I., Bunders, C., Devkota, K.P., Charan, R.D., Ramirez, C., Priedmann, C. and Markosyan, A. (2014) Isolation and Characterization of a Novel Rebaudioside M Isomer from a Bioconversion Reaction of Rebaudioside A and NMR Comparison Studies of Rebaudioside M Isolated from Stevia rebaudiana Bertoni and Stevia rebaudiana Morita. Biomolecules, 4, 374-389. http://dx.doi.org/10.3390/biom4020374
[7]	JECFA (2010) Steviol Glycosides [Prepared at the 73rd JECFA (2010) and published in FAO JECFA Monographs 10 (2010)]. In: Combined Compendium of Food Additive Specifications (Online Edition). General Specifications for Enzymes Analytical Methods, Volume 4. (FAO JECFA Monographs 10). Food and Agriculture Organization of the United Nations (FAO), Joint FAO/WHO Expert Committee on Food Additives (JECFA), Rome. http://www.fao.org/ag/agn/jecfa-additives/specs/monograph10/additive-442-m10.pdf
[8]	Bedir, E., Toyang, N.J., Khan, I.A., Walker, L.A. and Clark, A.M. (2001) A New Dammarane Type Triterpene Glycoside from Polyscias fulva. Journal of Natural Products, 64, 95-97. http://dx.doi.org/10.1021/np0003589
[9]	Chaturvedula, V.S.P., Schilling, J.K., Miller, J.S., Andriantsiferana, R., Rasamison, V.E. and Kingston, D.G.I. (2003) New Cytotoxic Oleanane Saponins from the Infructescences of Polyscias amplifolia from the Madagascar Rainforest. Planta Medica, 69, 440-444. http://dx.doi.org/10.1055/s-2003-39711
[10]	Huan, V.D., Yamamura, S., Ohtani, K., Kasai, R., Yamasaki, K. and Nham, N.T. (1998) Oleanane Saponins from Polysciasfructicosa. Phytochemistry, 47, 451-457. http://dx.doi.org/10.1016/S0031-9422(97)00618-3
[11]	Ohtani, K., Aikawa, Y., Kasai, R., Chou, W., Yamasaki, K. and Tanaka, O. (1992) Minor Diterpene Glycosides from Sweet Leaves of Rubus suavissimus. Phytochemistry, 31, 1553-1559. http://dx.doi.org/10.1016/0031-9422(92)83105-8
[12]	Chaturvedula, V.S.P., Mubarak, C. and Prakash, I. (2012) IR Spectral Analysis of Diterpene Glycosides of Stevia rebaudiana. Food and Nutrition Sciences, 3, 1467-1471. http://dx.doi.org/10.4236/fns.2012.310191
[13]	Chaturvedula, V.S.P., Chen, S., Yu, O. and Mao, G. (2013) NMR Spectral Analysis and Hydrolysis Studies of Rebaudioside N, a Minor Steviol Glycoside of Stevia rebaudiana Bertoni. Food and Nutrition Sciences, 4, 1004-1008. http://dx.doi.org/10.4236/fns.2013.410130
[14]	Chaturvedula, V.S.P. and Prakash, I. (2011) A New Diterpenoid Glycoside from Stevia rebaudiana. Molecules, 16, 2937-2943. http://dx.doi.org/10.3390/molecules16042937
[15]	Chaturvedula, V.S.P. and Prakash, I. (2011) Structures of the Novel Diterpene Glycosides from Stevia rebaudiana, Carbohydrate Research, 346, 1057-1060. http://dx.doi.org/10.1016/j.carres.2011.03.025