Structures of Some Novel α-Glucosyl Diterpene Glycosides from the Glycosylation of Steviol Glycosides

Molecules

Volumn 19, Issue 12, 2014, Pages 20280-20294

  Prakash, Indra ^a   Chaturvedula, Venkata Sai Prakash ^a,b  

^a The Coca Cola Company   (United States)

^b Natural Products Research Group Wisdom Natural Brands   (United States)

Author keywords

Asteraceae; Compositae; Diterpenoid glycosides; Glycosylation; Hydrolysis studies; MS; NMR; Stevia rebaudiana

Indexed keywords

DITERPENE; GLYCOSIDE; PLANT EXTRACT;

CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; STEVIA;

DITERPENES; GLYCOSIDES; GLYCOSYLATION; HYDROLYSIS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT EXTRACTS; STEVIA;

EID: 84919774925     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules191220280     Document Type: Article

References (17)

1. Lewis, W.H. Early uses of Stevia rebaudiana (Asteraceae) leaves as a sweetener in Paraguay. Econ. Bot. 1992, 46, 336-337.
2. Ibrahim, M.A.; Rodenburg, D.L.; Alves, K.; Fronczek, F.R.; McChesney, J.D.; Wu, C; Nettles, B.J.; Venkataraman, S.K.; Jacksch, F. Minor diterpene glycosides from the leaves of Stevia rebaudiana. J. Nat. Prod. 2014, 77, 1231-1235.
3. Mosettig, E.; Nes, W.R. Stevioside. II. The structure of the aglucon. J. Org. Chem. 1955, 20, 884-899.
4. 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.
5. Brandle, J.E.; Starrratt, A.N.; Gijen, M. Stevia rebaudiana: Its agricultural, biological and chemical properties. Can. J. Plant Sci. 1998, 78, 527-536.
6. Wayne, E.S.; Lin, L. NMR studies of the conformation of the natural sweetener rebaudioside A. Carbohydr. Res. 2009, 344, 2533-2538.
7. Chaturvedula, V.S.P.; Mani, U.; Prakash, I. Structures of the novel α-glucosyl linked diterpene glycosides from Stevia rebaudiana. Carbohydr. Res. 2011, 346, 2034-2038.
8. Prakash, I.; Chaturvedula, V.S.P.; Markosyan, A. Isolation, characterization and sensory evaluation of a hexa β-D-glucopyranosyl diterpene from Stevia rebaudiana. Nat. Prod. Commun. 2013, 8, 1523-1526.
9. Prakash, I.; Chaturvedula, V.S.P. Additional minor diterpene glycosides from Stevia rebaudiana bertoni. Molecules 2013, 18, 13510-13519.
10. Chaturvedula, V.S.P.; Mani, U.; Prakash, I. Diterpene glycosides from Stevia rebaudiana. Molecules 2011, 16, 3552-3562.
11. Chaturvedula, V.S.P.; Prakash, I. A new diterpenoid glycoside from Stevia rebaudiana. Molecules 2011, 16, 2937-2943.
12. Chaturvedula, V.S.P.; Prakash, I. Structures of the novel diterpene glycosides from Stevia rebaudiana. Carbohydr. Res. 2011, 346, 1057-1060.
13. 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.
14. 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.
15. Huan, V.D.; Yamamura, S.; Ohtani.K.; Kasai, R.; Yamasaki, K.; Nham, N.T. Oleanane saponins from Polyscias fructicosa. Phytochemistry 1998, 47, 451-457.
16. Tanaka, T.; Nakashima, T.; Ueda, T.; Tomii, K.; Kouno, I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem. Pharm. Bull. 2007, 55, 899-901.
17. Abelyan, V.; Markosyan, A.; Abelyan, L. Sweetner and use. U.S. Patent Application No. 2010/0166679, 1 July 2010.