Low Calorie Nonnutritive Sweeteners - Sweeteners: Nutritional Aspects, Applications, and Production Technology - page 92

O-R2

CH 3 CH 2

CH 3 COO-R1

Compound name R1 R2

1
2
3
4

Steviol
Steviolbioside
Stevioside
Rebaudioside A

H
H
β-Glc
β-Glc

H
β-Glc-β-Glc(2 1)
β-Glc-β-Glc(2 1)
β-Glc-β-Glc(2 1)

β-Glc(3 1)
β-Glc-β-Glc(2 1) 5 Rebaudioside B H

β-Glc(3 1)
β-Glc-α-Rha(2 1) 6 Rebaudioside C

(Dulcoside B)

β-Glc

β-Glc(3 1)
β-Glc-β-Glc(2 1) 7 Rebaudioside D β-Glc-β-Glc(2 1)

β-Glc(3 1)
β-Glc-β-Glc(2 1)
β-Glc-β-Xyl(2 1)

8
9

Rebaudioside E
Rebaudioside F

β-Glc-β-Glc(2 1)
β-Glc

β-Glc(3 1)
β-Glc-α-Rha(2 1) 10 Dulcoside A β-Glc

Chemical structure of steviosides. in rebaudioside D and E, R1 is composed of 2 b-Glc-b-Glc(2 - 1).
in rebaudioside A, B, C, D, E, and F in group R2, an additional sugar moiety is added on carbon 3
of the irst b-Glc. in rebaudioside F, one b-Glc is substituted for by-b-Xyl.

Figure 4.9

Acuteandsubacutetoxicitystudiesrevealedaverylowtoxicityofsteviaandstevioside.Steviaand
steviosidearesafewhenusedasasweetener.TheyaresuitedforbothdiabeticsandPKUpatients,as
wellasforobesepersonsintendingtoloseweightbyavoidingsugarsupplementsinthediet.Noaller-
gicreactionstoitseemtoexist.Stevioside,themainsweetcomponentintheleavesof S. rebaudiana
(Bertoni)Bertoni,tastesabout300timessweeterthansucrose(0.4%solution).Structuresofthesweet
components of Stevia occurring mainly in the leaves are given in Figure 4.9. Their content varies
between4%and20%ofthedryweightoftheleavesdependingonthecultivarandgrowingcondi-
tions.Stevioside3isthemainsweetcomponent.Theadvantagesofsteviosideasadietarysupplement
forhumansubjectsaremanifold:itisstable,isnoncaloriic,maintainsgooddentalhealthbyreducing
theintakeofsugar,andopensthepossibilityforusebydiabeticandPKUpatientsandobesepersons.
Therehasbeenconsiderablecommercialinterestinusing Stevia asafood/beveragesweetener.
InDecember2008,theFDAgavea“noobjection”approvalforGRASstatustoTruvia(developed
byCargillandtheCoca-ColaCompany)andPureVia(developedbyPepsiCoandtheWholeEarth
SweetenerCompany,asubsidiaryofMerisant),bothofwhicharewhollyderivedfromthe Stevia
plant.Abitteraftertasteassociatedwith Stevia hasbeenaproblemforcompanieswishingtousethe