NMR Spectral Assignments and Hydrolysis Studies of Dulcosides A and B

The complete 1H and 13C NMR assignments for the two diterpene glycosides 13-[(2-O-a-L-rhamnopyranosyl-B-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid B-D-glucopyranosyl ester (Dulcoside A) and 13-[(2-O-a-L-rhamnopyranosyl-3-O-B-D-glucopyranosyl-B-D-glucopyranosyl)oxy]-ent-kaur-16-en-19-oic acid B-D-glucopyranosyl ester (Dulcoside B) isolated from Stevia rebaudiana were achieved by the extensive NMR (1H and 13C, COSY, HSQC, HMBC) and mass spectral data. Further, hydrolysis of the two compounds Dulcosides A and B was performed using acid and enzymatic studies to identify their aglycone and sugar residues.

[1]  I. Prakash,et al.  Synthesis of ent-Kaurane Diterpene Monoglycosides , 2011, Molecules.

[2]  I. Prakash,et al.  Structures of the novel α-glucosyl linked diterpene glycosides from Stevia rebaudiana. , 2011, Carbohydrate research.

[3]  D. Milanowski,et al.  Minor diterpenoid glycosides from the leaves of Stevia rebaudiana , 2011 .

[4]  I. Prakash,et al.  Additional Minor Diterpene Glycosides from Stevia rebaudiana , 2011, Natural product communications.

[5]  I. Prakash,et al.  Structures of the novel diterpene glycosides from Stevia rebaudiana. , 2011, Carbohydrate research.

[6]  I. Prakash,et al.  Diterpene Glycosides from Stevia rebaudiana , 2011, Molecules.

[7]  I. Prakash,et al.  A New Diterpene Glycoside from Stevia rebaudiana , 2011, Molecules.

[8]  D. Milanowski,et al.  Two Minor Diterpene Glycosides from the Leaves of Stevia rebaudiana , 2011, Natural product communications.

[9]  I. Prakash,et al.  ISOLATION AND NMR SPECTRAL ASSIGNMENTS OF STEVIOLBIOSIDE AND STEVIOSIDE , 2011 .

[10]  V. Sai,et al.  ISOLATIO N AND NMR SPECTRAL ASSIGNMENTS OF STEVIOLBIOSIDE AND STEVI OSIDE , 2011 .

[11]  M. Ohta,et al.  Characterization of Novel Steviol Glycosides from Leaves of Stevia rebaudiana Morita , 2010 .

[12]  雅也 太田,et al.  Stevia rebaudiana Moritaの葉から抽出した新規ステビオール配糖体の解析 , 2010 .

[13]  Wayne E Steinmetz,et al.  NMR studies of the conformation of the natural sweetener rebaudioside A. , 2009, Carbohydrate research.

[14]  G. Dubois,et al.  Photostability of rebaudioside A and stevioside in beverages. , 2008, Journal of agricultural and food chemistry.

[15]  T. Ueda,et al.  Facile discrimination of aldose enantiomers by reversed-phase HPLC. , 2007, Chemical & pharmaceutical bulletin.

[16]  J. Miller,et al.  New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest. , 2003, Planta medica.

[17]  L. Walker,et al.  A new dammarane-type triterpene glycoside from Polyscias fulva. , 2001, Journal of natural products.

[18]  A. Starratt,et al.  Stevia rebaudiana: Its agricultural, biological, and chemical properties , 1998 .

[19]  M. C. Hoang,et al.  Oleanane saponins from Polyscias fruticosa. , 1998, Phytochemistry.

[20]  R. Kasai,et al.  Minor diterpene glycosides from sweet leaves of Rubus suavissimus , 1992 .

[21]  J. R. Hanson,et al.  Hydrolysis of the diterpenoid glycoside, stevioside , 1990 .

[22]  E. Mosettig,et al.  The Absolute Configuration of Steviol and Isosteviol , 1963 .

[23]  E. Mosettig,et al.  STEVIOSIDE. II. THE STRUCTURE OF THE AGLUCON , 1955 .