Five New Ent-Atisene Glycosides From Stevia rebaudiana

Abstract

Five new ent-atisene diterpene glycosides (1-5) have been isolated from Stevia rebaudiana Bertoni. This adds to a list of only 2 new ent-atisene diterpene glycosides isolated previously from S. rebaudiana. Diterpene glycosides isolated from S. rebaudiana, such as the rebaudiosides, are typically associated with the ent-kaurene core and glycosylation at the C-13 and C-19 positions. Extensive application of nuclear magnetic resonance spectroscopy techniques (1H, 13C, 1D-TOCSY, COSY, HSQC-DEPT, HMBC, and ROESY) as well as high-resolution mass spectrometry demonstrated that the ent-atisenes 1 to 5 had glycosylation patterns identical to rebaudiosides J, N, O, K, and T, respectively. We have named these compounds stevatisene J, N, O, K, and T, respectively.

Approaches toward the Separation, Modification, Identification and Scale up Purification of Tetracyclic Diterpene Glycosides from Stevia rebaudiana (Bertoni) Bertoni

“…All these developments have allowed the discovery of several new natural and slightly modified DGs with remarkable potential as sugar substitutes e.g., several rebaudioside A isomers, a stevioside like-compound with a disaccharide linked at position C-12 of the aglycone [ 22 ], rebaudioside R (unique example with a non-glucose monosaccharide linked directly at position C-13 (xylose) [ 23 ], rebaudioside U and similar compounds, the only steviol glycosides with an arabinopyranosyl moiety [ 24 , 25 ], rebaudioside W (unique hexa-glycoside from S. rebaudiana with three different sugar monosaccharides attached (glucose, xylose and rhamnose) [ 26 ]. Additionally, rebaudioside IX series are the largest natural DGs composed of nine glucose units linked to steviol [ 27 , 28 , 29 ], only one natural example of rebaudioside M isomer has been reported [ 30 ] and a few new compounds with an ent -atisene core have also been reported [ 31 , 32 ]. Nowadays, many natural, chemically, and enzymatically modified diterpene glycosides with diverse sugar interlinkages and cores have been discovered, hence, a wide spectrum of structures are now available to evaluate for their sweetener potential and to understand better the relationship between structure-sweetness/lingering aftertaste.…”

Chemical Analysis and Antidiabetic Potential of a Decoction from Stevia serrata Roots

“…In summary, S. serrata biosynthesized ent -kauranoic- and ent -atisenoic-type acid glycosides like other species of Stevia . This report describes for the third time the presence of ent -atisenoic glycosides esters, previously reported from the roots of S. salicifolia collected in Mexico and from a commercial sample of the leaves from S. rebaudiana …”

“…This report describes for the third time the presence of ent-atisenoic glycosides esters, previously reported from the roots of S. salicifolia collected in Mexico and from a commercial sample of the leaves from S. rebaudiana. 59 In vivo evaluation demonstrated the hypoglycemic and antihyperglycemic activities of SSD in healthy and STZ-hyperglycemic mice. Glycoside 2 exhibited a hypoglycemic effect lower than that of SSD, which could be related to poor bioavailability.…”