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Ziziphin
Ziziphin, a triterpene glycoside which exhibits taste-modifying properties, has been isolated from the leaves of ''Ziziphus jujuba'' (''Rhamnaceae''). Among ziziphin's known homologues found in this plant, it is the most anti-sweet. However, its anti-sweet activity is less effective than gymnemic acid 1, another anti-sweet compound glycoside isolated from the leaves of ''Gymnema sylvestre'' (Asclepiadaceae).Kinghorn, A.D. and Compadre, C.M. ''Alternative Sweeteners: Third Edition, Revised and Expanded'', Marcel Dekker ed., New York, 2001. Ziziphin reduces perceived sweetness of most of the carbohydrates (e.g. glucose, fructose), bulk sweeteners, intense sweeteners (natural: steviol glycoside – artificial: sodium saccharin and aspartame Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade n ...
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Ziziphus Zizyphus
Jujube (), sometimes jujuba, known by the scientific name ''Ziziphus jujuba'' and also called red date, Chinese date, and Chinese jujube, is a species in the genus ''Ziziphus'' in the buckthorn family Rhamnaceae. Description It is a small deciduous tree or shrub reaching a height of , usually with thorny branches. The leaves are shiny-green, ovate-acute, long and wide, with three conspicuous veins at the base, and a finely toothed margin. The flowers are small, wide, with five inconspicuous yellowish-green petals. The fruit is an edible oval drupe deep; when immature it is smooth-green, with the consistency and taste of an apple with lower acidity, maturing brown to purplish-black, and eventually wrinkled, looking like a small date. There is a single hard kernel, similar to an olive pit, containing two seeds. Chemistry Leaves contain saponin and ziziphin, which suppresses the ability to perceive sweet taste. Flavinoids found in the fruits include Kaempferol 3-O ...
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Triterpene
Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squalene, the precursor to all steroids. Structures Triterpenes exist in a great variety of structures. Nearly 200 different skeletons have been identified. These skeletons may be broadly divided according to the number of rings present. In general pentacyclic structures (5 rings) tend to dominate. Squalene is biosynthesized through the head-to-head condensation of two farnesyl pyrophosphate units. This coupling converts a pair of C15 components into a C30 product. Squalene serves as precursor for the formation of many triterpenoids, including bacterial hopanoids and eukaryotic sterols. Triterpenoids By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms ''triterpene'' and ''triterpenoid'' oft ...
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Aspartame
Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade names ''NutraSweet'', ''Equal'', and ''Canderel''. First submitted for approval as a food ingredient in 1974, aspartame was approved by the US Food and Drug Administration (FDA) in 1981. Aspartame is one of the most rigorously tested food ingredients. Reviews by over 100 governmental regulatory bodies found the ingredient safe for consumption at current levels.Food Standards Australia New Zealand: , several reviews of clinical trials showed that using aspartame in place of sugar reduces calorie intake and body weight in adults and children. Uses Aspartame is around 180 to 200 times sweeter than sucrose (table sugar). Due to this property, even though aspartame produces of energy per gram when metabolized, the quantity of aspartame ne ...
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Saponins
Saponins (Latin "sapon", soap + "-in", one of), also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed but found particularly in soapwort (genus Saponaria), a flowering plant, the soapbark tree (''Quillaja saponaria'') and soybeans (''Glycine max'' L.). They are used in soaps, medicinals, fire extinguishers, speciously as dietary supplements, for synthesis of steroids, and in carbonated beverages (the head on a mug of root beer). Structurally, they are glycosides, sugars bonded to another organic molecule, usually a steroid or triterpene, a steroid building block. Saponins are both water and fat soluble, which gives them their useful soap properties. Some examples of these chemicals are glycyrrhizin, licorice flavoring; and quillaia (alt. quillaja), a bark extract used in beverages. Uses The saponins are a subclass of terpenoids, the larges ...
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Taste Modifiers
The gustatory system or sense of taste is the sensory system that is partially responsible for the perception of taste (flavor). Taste is the perception produced or stimulated when a substance in the mouth reacts chemically with taste receptor cells located on taste buds in the oral cavity, mostly on the tongue. Taste, along with olfaction and trigeminal nerve stimulation (registering texture, pain, and temperature), determines flavors of food and other substances. Humans have taste receptors on taste buds and other areas, including the upper surface of the tongue and the epiglottis. The gustatory cortex is responsible for the perception of taste. The tongue is covered with thousands of small bumps called papillae, which are visible to the naked eye. Within each papilla are hundreds of taste buds. The exception to this is the filiform papillae that do not contain taste buds. There are between 2000 and 5000Boron, W.F., E.L. Boulpaep. 2003. Medical Physiology. 1st ed. Elsevier Sc ...
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Gymnemic Acid
Gymnemic acids are a class of chemical compounds isolated from the leaves of ''Gymnema sylvestre'' (Asclepiadaceae). They are anti-sweet compounds, or sweetness inhibitors. After chewing the leaves, solutions sweetened with sugar taste like water. Chemically, gymnemic acids are triterpenoid glycosides. The central structure is the aglycone gymnemagenin (C30H50O6). This is adorned with a sugar such as glucuronic acid and with various ester groups. These variations give rise to the different gymnemic acids. More than 20 homologs of gymnemic acid are known. Gymnemic acid I has the highest anti-sweet properties. It suppresses the sweetness of most of the sweeteners including intense artificial sweeteners such as aspartame and natural sweeteners such as thaumatin, a sweet protein. The anti-sweet activity is reversible, but sweetness recovery on the tongue can take more than 10 minutes. Example chemical structures See also Other anti-sweeteners: * Hodulcine, a dammarane-type tri ...
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Lactisole
Lactisole is the sodium salt and commonly supplied form of 2-(4-methoxyphenoxy)propionic acid, a natural carboxylic acid found in roasted coffee beans. Like gymnemic acid, it has the property of masking sweet flavors and is used for this purpose in the food industry. Chemistry Chemically, lactisole is a double ether of hydroquinone. Since it contains an asymmetric carbon atom the molecule is chiral, with the S enantiomer predominating in natural sources and being primarily responsible for the sweetness-masking effect. Commercial lactisole is a racemic mixture of the R and S forms.T. Nakagita et al "Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor" PLoS One. 2019; 14(3): e0213552 Natural occurrences The parent acid of lactisole was discovered in 1989 in roasted Colombian arabica coffee beans in a concentration of 0.5 to 1.2 ppm. Anti-sweet properties At concentrations of 100–150 parts ...
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Hodulcine
Hodulcine (or hoduloside) are glycosides (dammarane-type triterpenes) which are isolated from the leaves of ''Hovenia dulcis Thunb.'' (''Rhamnaceae'') also known as Japanese Raisin Tree. Several glycosides homologue have been found in this plant and although hoduloside 1 exhibits the highest anti-sweet activity, it is less potent than gymnemic acid 1.Kinghorn, A.D. and Compadre, C.M. Alternative Sweeteners: Third Edition, Revised and Expanded, Marcel Dekker ed., New York, 2001. See also * Gymnemic acid * Lactisole * Ziziphin Ziziphin, a triterpene glycoside which exhibits taste-modifying properties, has been isolated from the leaves of ''Ziziphus jujuba'' (''Rhamnaceae''). Among ziziphin's known homologues found in this plant, it is the most anti-sweet. However, its ... References External links Hovenia dulcis - Plants For A Future database report Taste modifiers Triterpene glycosides {{organic-compound-stub ...
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Glycine
Glycine (symbol Gly or G; ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable), with the chemical formula NH2‐ CH2‐ COOH. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG (GGU, GGC, GGA, GGG). Glycine is integral to the formation of alpha-helices in secondary protein structure due to its compact form. For the same reason, it is the most abundant amino acid in collagen triple-helices. Glycine is also an inhibitory neurotransmitter – interference with its release within the spinal cord (such as during a ''Clostridium tetani'' infection) can cause spastic paralysis due to uninhibited muscle contraction. It is the only achiral proteinogenic amino acid. It can fit into hydrophilic or hydrophobic environments, due to its minimal side chain of only one hydrogen atom. History and etymology Glycine was discovered in 1820 by the French chemist He ...
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Steviol Glycoside
Steviol glycosides are the chemical compounds responsible for the sweet taste of the leaves of the South American plant ''Stevia rebaudiana'' (Asteraceae) and the main ingredients (or precursors) of many sweeteners marketed under the generic name stevia and several trade names. They also occur in the related species '' S. phlebophylla'' (but in no other species of ''Stevia'') and in the plant '' Rubus chingii'' (Rosaceae). Steviol glycosides from ''Stevia rebaudiana'' have been reported to be between 30 and 320 times sweeter than sucrose, although there is some disagreement in the technical literature about these numbers. They are heat-stable, pH-stable, and do not ferment. Steviol glycosides do not induce a glycemic response when ingested, because humans cannot metabolize stevia. The acceptable daily intake (ADI) for steviol glycosides, expressed as steviol equivalents, has been established to be 4 mg/kg body weight/day, and is based on no observed effects of a 100 fol ...
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Saccharin
Saccharin (''aka'' saccharine, Sodium sacchari) is an artificial sweetener with effectively no nutritional value. It is about 550 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations. Saccharin is used to sweeten products such as drinks, candies, cookies, and especially for masking bitter taste of some medicines. Etymology Saccharin derives its name from the word "saccharine", meaning "sugary". The word saccharine is used figuratively, often in a derogative sense, to describe something "unpleasantly over-polite" or "overly sweet". Both words are derived from the Greek word (''sakkharon'') meaning "gravel". Similarly, saccharose is an obsolete name for sucrose (table sugar). Properties Saccharin is heat-stable. It does not react chemically with other food ingredients; as such, it stores well. Blends of saccharin with other sweeteners are often used to compensate for each sweetener's weaknesses and faults. A 10:1 cyclamate–sacch ...
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Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of ''Heliconius'' butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body. In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an ''O-glycoside''), N- (a ''glycosylamine''), S-(a ''thioglycoside''), or C- (a '' C-glycoside'') glycosidic bond. According to th ...
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