Charantin
Encyclopedia
Charantin is a chemical substance obtained from the Asia
n bitter melon
(Momordica charantia), reputed to be responsible for the hypoglycaemic properties of those plants. It was identified by Lolitkar and Rao in 1960. It was also found in the similar Africa
n species M. foetida
, by A. Olaniyi in 1975, under the name foetidin.
Charantin is actually a 1:1 mixture of two steroid
al saponin
s, β-sitosteryl
glucoside
and 5,25-stigmasteryl
glucoside . It is a whitish crystalline substance, neutral and tasteless, melting at 266–268°C. It is
sparingly soluble in water or other highly polar solvents, as well as in apolar solvents like hexane
, but is soluble in ether
, ethanol
and methanol
, and can be efficiently extracted from the plant by pressurized ethanol
or acetone
at 100°C.
The name charantin has also been used by A. Parkash and other for a different compound, a peptide
with molecular mass 9.7 kDa, also isolated from bitter melon
seeds.
Asia
Asia is the world's largest and most populous continent, located primarily in the eastern and northern hemispheres. It covers 8.7% of the Earth's total surface area and with approximately 3.879 billion people, it hosts 60% of the world's current human population...
n bitter melon
Bitter melon
Momordica charantia, called bitter melon or bitter gourd in English, is a tropical and subtropical vine of the family Cucurbitaceae, widely grown in Asia, Africa, and the Caribbean for its edible fruit, which is among the most bitter of all fruits...
(Momordica charantia), reputed to be responsible for the hypoglycaemic properties of those plants. It was identified by Lolitkar and Rao in 1960. It was also found in the similar Africa
Africa
Africa is the world's second largest and second most populous continent, after Asia. At about 30.2 million km² including adjacent islands, it covers 6% of the Earth's total surface area and 20.4% of the total land area...
n species M. foetida
Momordica foetida
Momordica foetida is a perennial climbing vine native of tropical Africa, closely related to the bitter melon and balsam apple . Its species name refers to its unpleasant smell. It was previously named M. morkorra and M...
, by A. Olaniyi in 1975, under the name foetidin.
Charantin is actually a 1:1 mixture of two steroid
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...
al saponin
Saponin
Saponins are a class of chemical compounds, one of many secondary metabolites found in natural sources, with saponins found in particular abundance in various plant species...
s, β-sitosteryl
Beta-sitosterol
β-Sitosterol is one of several phytosterols with chemical structures similar to that of cholesterol. Sitosterols are white, waxy powders with a characteristic odor...
glucoside
Glucoside
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes....
and 5,25-stigmasteryl
Stigmasterol
Stigmasterol is one of a group of plant sterols, or phytosterols, that include beta-sitosterol, campesterol, ergosterol , brassicasterol, delta-7-stigmasterol and delta-7-avenasterol, that are chemically similar to animal cholesterol...
glucoside . It is a whitish crystalline substance, neutral and tasteless, melting at 266–268°C. It is
sparingly soluble in water or other highly polar solvents, as well as in apolar solvents like hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...
, but is soluble in ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...
, ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
and methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...
, and can be efficiently extracted from the plant by pressurized ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
or acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
at 100°C.
The name charantin has also been used by A. Parkash and other for a different compound, a peptide
Peptide
Peptides are short polymers of amino acid monomers linked by peptide bonds. They are distinguished from proteins on the basis of size, typically containing less than 50 monomer units. The shortest peptides are dipeptides, consisting of two amino acids joined by a single peptide bond...
with molecular mass 9.7 kDa, also isolated from bitter melon
Bitter melon
Momordica charantia, called bitter melon or bitter gourd in English, is a tropical and subtropical vine of the family Cucurbitaceae, widely grown in Asia, Africa, and the Caribbean for its edible fruit, which is among the most bitter of all fruits...
seeds.
See also
- momordicosideMomordicosideMomordicoside is any of several related glycosides that can be extracted from the bitter melon vine . They include:*Momordicoside A *Momordicoside B *momordicoside F1 *momordicoside F2 *Momordicoside K *Momordicoside L...
- charantosideCharantosideCharantoside is any of several related glycosides found in the fruits bitter melon vine . They include:* charantoside I, -5β,19-Epoxy-19-methoxycucurbita-6,23,25-trien-3β-ol 3-O-β-D-glucopyranoside: amorphous solid....
- goyaglycosideGoyaglycosidegoyaglycoside is any of several related glycosides found in the fruits bitter melon vine , called goya in Okinawan language. They include:* goyaglycoside c.* goyaglycoside d....
- karavilosideKaravilosideKaraviloside is any of several related glycosides found in bitter melon vine . They include:* Karaviloside I* Karaviloside II* Karaviloside III* Karaviloside V* Karaviloside XI...
- napin, another 7.8 kDa peptide isolated from bitter melon seeds.