Chemical and Functional Properties of Food Saccharides

© 2004 by CRC Press LLC
24.1.2 TERPENOIDS
The majority of intensely sweet naturally occurring compounds belong to the family
of terpenoids (mono-, sesqui-, di-, and triterpenoids; see Table 24.1). Many members
of this group are glycosides with one or more saccharide units, which improve their
solubility in water. Perilartine, a chemically modified sweetener being the (E)-oxime
of perilaldehyde (24.8), perialdehyde, and (E)-4-(methoxymethyl)-1,4-cyclohexadiene-1-carbaldoxime,
another semisynthetic sweetener (24.9), are sweet monoterpens.
CHO
H
C
OH
N
H
C
OH
N
CH2 CH2 CH2OCH 3
a b c
(24.7) (24.8) (24.9)
The group of sesquiterpenes is represented by the colorless, oily hernandulcin
(24.10). The toxicity of hernandulcin is low. Unpleasant aftertaste and natural bitterness
limits its applications in spite of its high sweet potency.
H 3C
O
H
CH3 CH3 CH HO
3
1
1´
6
5´
(24.10)
The group of sweet diterpenes is composed of sweet ent-kaurene glycosides
(24.11) to (24.19) isolated from the sweet herb Stevia rebaudiana Bertoni (Compositae).
Stevioside (24.11) is the major ent-kaurene glycoside of the leaves and
extracts of this plant apart from other glycosides (Table 24.2). The total yield of the
isolated sweet glycosides is 10% (6.6% stevioside, 3.7% rebaudioside A, 2.1%
rebaudioside C, and 0.53% dulcoside A).
The group of sweet diterpenes includes also baiynoside (24.20), a sweet labdane
glycoside from the roots of a Chinese officinal herb Bai-Yun-Shen used in the therapy
of gynecological diseases and gaudichaudioside A (24.21), a sweet diterpene glycoside
isolated from the Paraguayan medical plant. 2 This fairly water-soluble compound
has a pleasant taste with a low concomitant perception of bitterness. 12
A group of triterpenoids includes the sweet oleanane glycoside glycyrrhizin
(24.22). It forms colorless crystals poorly soluble in cold water but well soluble in
hot water or ethanol. Glycyrrhizin, the sweet principle of the licorice root, is a