Isolation,and Structural Characterization of a New Hexa β-D-Glucopyranosyl Diterpene from Stevia rebaudiana

Abstract

A new diterpene glycoside with six β-D-glucopyranosyl units was isolated from the extract of the leaves of Stevia rebaudiana Bertoni, which was identified as 13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy] ent-kaur-16-en-19-oic acid-[2-O-β-D-glucopyranosyl-3-O-(2-O-β-D-glucopyranosyl)-β-D-glucopyrano-syl -β-D-glucopyranosyl) ester (1) based on the extensive NMR (¹H and ¹³C, COSY, HSQC, and HMBC) and mass spectral data as well as hydrolysis studies.

Keywords

Stevia rebaudiana Asteraceae Structure characterization Spectral data Hydrolysis studies

References

Lewis

W.H.

(1992) Early uses of Stevia rebaudiana (Asteraceae) leaves as a sweetener in Paraguay. Economic Botany, 46, 336–337.

Ceunen

, Geuns

J.M.C.

(2013) Steviol glycosides: Chemical diversity, metabolism, and function. Journal of Natural Products, 76, 1201–1228.

Brandle

J.E.

, Starrratt

A.N.

, Gijen

(1998) Stevia rebaudiana: its agricultural, biological and chemical properties. Canadian Journal of Plant Sciences, 78, 527–536.

Kinghorn

A.D.

(2002) In stevia: the genus stevia (medicinal and aromatic plants-industrial profile); Taylor and Francis 19, 1–17.

Ibrahim

M.A.

, Rodenburg

D.L.

, Alves

, Fronczek

F.R.

, McChesney

J.D.

, Wu

, Nettles

B.J.

, Venkataraman

S.K.

, Jacksch (2014) Minor diterpene glycosides from the leaves of Stevia rebaudiana. Journal of Natural Products, 77, 1231–1235.

JEFCA. (2010) Steviol glycosides. In Combined Compendium of Food Additive Specifications [Online Edition]. Food and Agriculture Organization of the United Nations (FAO), Joint FAO/WHO Expert Committee on Food Additives (JECFA), Rome. Italy. Available from: http://www.fao.org/ag/agn/jecfa-additives/specs/monograph10/additive-442-m10.pdf.

Chaturvedula

V.S.P.

, Zamora

(2014) Reversed-phase HPLC analysis of steviol glycosides isolated from Stevia rebaudiana Bertoni. Food and Nutrition Scences, 5, 1711–1716.

Chaturvedula

V.S.P.

(2014) Isolation and structural characterization of a new minor penta β-D-glucopyranosyl diterpene from Stevia rebaudiana Bertoni. American Journal of Plant Sciences, 5, 3519–3525.

Chaturvedula

V.S.P.

, Meneni

S.R.

(2016) Isolation and structural characterization of a new minor steviol glycoside of Stevia rebaudiana. IOSR Journal of Pharmacy, 6, 01–05.

10.

Chaturvedula

V.S.P.

, Meneni

S.R.

(2017) A new penta β-D-glucopyranosyl diterpene from Stevia rebaudiana. International Journal of Organic Chemistry, 7, 91–98.

11.

Bedir

, Toyang

N.J.

, Khan

I.A.

, Walker

L.A.

, Clark

A.M.

(2001) A new dammarane type triterpene glycoside from Polyscias fulva. Journal of Natural Products, 64, 95–97.

12.

Chaturvedula

V.S.P.

, Schilling

J.K.

, Miller

J.S.

, Andriantsiferana

, Rasamison

V.E.

, Kingston

D.G.I.

(2003) New cytotoxic oleanane saponins from the infructescences of Polyscias amplifolia from the Madagascar rainforest. Planta Medica, 69, 440–444.

13.

Huan

V.D.

, Yamamura

, Ohtani

, Kasai

, Yamasaki

, Nham

N.T.

(1998) Oleanane saponins from Polyscias fructicosa. Phytochemistry, 47, 451–457.

14.

Ohta

, Sasa

, Inoue

, Tamai

, Fujita

, Morita

, Matsuura

(2010) Characterization of novel steviol glycosides from leaves of Stevia rebaudiana Morita. Journal of Applied Glycosciences, 57, 199–209.

15.

Ohtani

, Aikawa

, Kasai

, Chou

, Yamasaki

, Tanaka

(1992) Minor diterpene glycosides from sweet leaves of Rubus suavissimus. Phytochemistry, 31, 1553–1559.

16.

Chaturvedula

V.S.P.

, Prakash

(2013) Structural characterization and hydrolysis of rebaudioside E, a minor sweet component of Stevia rebaudiana. European Chemical Bulletin, 2, 298–302.

17.

Prakash

, Chaturvedula

V.S.P.

, Markosyan

(2013) Isolation, Characterization and sensory evaluation of a hexa β-D-glucopyranosyl diterpene from Stevia rebaudiana. Natural Product Communications, 9, 1677–1679.

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