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Hodulcine
Hodulcine (or hoduloside) are glycosides (dammarane-type triterpenes) which are isolated from the leaves of ''Hovenia dulcis Thunb.'' (''Rhamnaceae The Rhamnaceae are a large family of flowering plants, mostly trees, shrubs, and some vines, commonly called the buckthorn family. Rhamnaceae is included in the order Rosales. The family contains about 55 genera and 950 species. The 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 References External links Hovenia dulcis - Plants For A Future database report Taste modifiers Triterpene glycosides {{organic-compound-stub ...
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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 Hodulcine (or hodul ...
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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 Hodulcine (or hodul ...
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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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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) and sweet amino acids (e.g. 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‐ C ...
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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. Accordin ...
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Dammarane
Dammarane is a tetracyclic triterpene found in sapogenins (forming triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol and protopanaxadiol). Compounds of the series were first isolated from and named after dammar resin, a natural resin from tropical trees of the Dipterocarp family. Mills J.S. (1956) "The Constitution of the Neutral, Tetracyclic Triterpenes of Dammar Resin" ''Journal of the Chemical Society'' 2196-2202 References External links Numbering of dammarane according to IUPAC Recommendations
Steroids Triterpenes {{steroid-stub ...
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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 ''triterpenoi ...
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Hovenia Dulcis
''Hovenia dulcis'', the Japanese raisin tree or oriental raisin tree, is a hardy tree found in Asia, from Eastern China ( 萬壽果; pinyin: wànshòuguǒ) and Korea (헛개나무, ''heotgae namu'') to the Himalayas (up to altitudes of 2,000 m), growing preferably in a sunny position on moist sandy or loamy soils. The tree known for its health benefits when consumed in tea, introduced as an ornamental tree to several countries, also bears edible fruit. It is considered to be one of the most pervasive invaders in Brazilian subtropical forests. Description Tree, rarely a shrub, deciduous, to 10–30 m tall. Branchlets brown or black-purple, glabrous, with inconspicuous lenticels. The glossy leaves are large and pointed. The trees bear clusters of small cream-coloured hermaphroditic flowers in July. The drupes appear at the ends of edible fleshy fruit stalks (rachis), which is a type of accessory fruit. Uses The fleshy rachis of the infructescence is sweet, fragrant and is ed ...
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Rhamnaceae
The Rhamnaceae are a large family of flowering plants, mostly trees, shrubs, and some vines, commonly called the buckthorn family. Rhamnaceae is included in the order Rosales. The family contains about 55 genera and 950 species. The Rhamnaceae have a worldwide distribution, but are more common in the subtropical and tropical regions. The earliest fossil evidence of Rhamnaceae is from the Late Cretaceous. Fossil flowers have been collected from the Upper Cretaceous of Mexico and the Paleocene of Argentina. Leaves of family Rhamnaceae members are simple, i.e., the leaf blades are not divided into smaller leaflets.Flowering Plants of the Santa Monica Mountains, Nancy Dale, 2nd Ed. 2000, p. 166 Leaves can be either alternate or opposite. Stipules are present. These leaves are modified into spines in many genera, in some (e.g. ''Paliurus spina-christi'' and ''Colletia cruciata'') spectacularly so. ''Colletia'' stands out by having two axillary buds instead of one, one developing int ...
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Homology (chemistry)
In chemistry, homology is the appearance of homologues. A homologue (also spelled as homolog) is a compound belonging to a series of compounds differing from each other by a repeating unit, such as a methylene bridge −−, a peptide residue, etc. A homolog is a special case of an analog. Examples are alkanes and compounds with alkyl side chains of different length (the repeating unit being a methylene group -CH2-). Periodic table On the periodic table, homologous elements share many electrochemical properties and appear in the same group (column) of the table. For example, all noble gases are colorless, monatomic gases with very low reactivity. These similarities are due to similar structure in their outer shells of valence electrons. Mendeleev used the prefix eka- for an unknown element below a known one in the same group. See also * Homologous series * Analog * Congener * Structure–activity relationship The structure–activity relationship (SAR) is th ...
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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 ...
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