From the commercial extract of the leaves of Stevia rebaudiana Bertoni, a minor steviol glycoside, 13-[(2- O-β-D-glucopyranosyl-3- O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[(2- O-(3- O-β-D-glucopyranosyl-α-L-rhamnopyranosyl)-3- O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester] ( 1); also known as rebaudioside O having seven sugar units has been isolated. Its structural characterization has been achieved by the extensive 1D ( 1H and 13C), and 2D NMR (COSY, HMQC, HMBC) as well as mass spectral data. Further, hydrolysis studies were performed on rebaudioside O using acid and enzymatic methods to identify aglycone and sugar residues in its structure as well as their configurations.
References
[1]
Mosettig, E.; Nes, W.R. Stevioside. II. The structure of the aglucon. J. Org. Chem.？1955, 20, 884–899, doi:10.1021/jo01125a013.
[2]
Mosettig, E.; Beglinger, U.; Dolder, F.; Lichiti, H.; Quitt, P.; Waters, J.A. The absolute configuration of steviol and isosteviol. J. Am. Chem. Soc.？1963, 85, 2305–2309, doi:10.1021/ja00898a025.
[3]
Brandle, J.E.; Starrratt, A.N.; Gijen, M. Stevia rebaudiana: Its agricultural, biological and chemical properties. Can. J. Plant Sci.？1998, 78, 527–536, doi:10.4141/P97-114.
[4]
Wayne, E.S.; Lin, L. NMR studies of the conformation of the natural sweetener rebaudioside A. Carbohydr. Res.？2009, 344, 2533–2538, doi:10.1016/j.carres.2009.10.005.
[5]
Ohta, M.; Sasa, S.; Inoue, A.; Tamai, T.; Fujita, I.; Morita, K.; Matsuura, F. Characterization of novel steviol glycosides from leaves of Stevia rebaudiana Morita. J. Appl. Glycosci.？2010, 57, 199–209, doi:10.5458/jag.57.199.
[6]
Chaturvedula, V.S.P.; Mani, U.; Prakash, I. Diterpene glycosides from Stevia rebaudiana. Molecules？2011, 16, 3552–3562, doi:10.3390/molecules16053552.
[7]
Chaturvedula, V.S.P.; Prakash, I. A new diterpenoid glycoside from Stevia rebaudiana. Molecules？2011, 16, 2937–2943, doi:10.3390/molecules16042937.
[8]
Chaturvedula, V.S.P.; Prakash, I. Structures of the novel diterpene glycosides from Stevia rebaudiana. Carbohydr. Res.？2011, 346, 1057–1060, doi:10.1016/j.carres.2011.03.025.
[9]
Chaturvedula, V.S.P.; Rhea, J.; Milanowski, D.; Mocek, U.; Prakash, I. Two minor diterpene glycosides from the leaves of Stevia rebaudiana. Nat. Prod. Commun.？2011, 6, 175–178.
[10]
Bedir, E.; Toyang, N.J.; Khan, I.A.; Walker, L.A.; Clark, A.M. A new dammarane type triterpene glycoside from Polyscias fulva. J. Nat. Prod.？2001, 64, 95–97, doi:10.1021/np0003589.
[11]
Chaturvedula, V.S.P.; Schilling, J.K.; Miller, J.S.; Andriantsiferana, R.; Rasamison, V.E.; Kingston, D.G.I. New cytotoxic oleanane saponis from the infructescences of Polyscias amplifolia from the Madagascar rainforest. Planta Med.？2003, 69, 440–444, doi:10.1055/s-2003-39711.
