Charantoside

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Charantoside is any of several related cucurbitane triterpenoid glycosides found in the fruits bitter melon vine (Momordica charantia). [1] They include:

Glycoside molecule in which a sugar is bound to another functional group

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.

Charantosides I through VIII can be extracted from the fresh fruit with methanol and ethyl acetate. [1]

Methanol, also known as methyl alcohol among others, is a chemical with the formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated MeOH). Methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.

Ethyl acetate chemical compound

Ethyl acetate is the organic compound with the formula CH
3–COO–CH
2–CH
3, simplified to C
4H
8O
2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, decaffeinating tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. The combined annual production in 1985 of Japan, North America, and Europe was about 400,000 tonnes. In 2004, an estimated 1.3 million tonnes were produced worldwide.

See also

Related Research Articles

<i>Momordica balsamina</i> species of plant

Momordica balsamina is a tendril-bearing annual vine native to the tropical regions of Africa, introduced and invasive in Asia, Australia, and Central America. It has pale yellow, deeply veined flowers and round, somewhat warty, bright orange fruits, or "apples". When ripe, the fruits burst apart, revealing numerous seeds covered with a brilliant scarlet, extremely sticky coating. The balsam apple was introduced into Europe by 1568 and was used medicinally to treat wounds. In 1810, Thomas Jefferson planted this vine in his flower borders at Monticello along with larkspur, poppies, and nutmeg.

Cucurbitacin group of chemical compounds

Cucurbitacin is any of a class of biochemical compounds that some plants — notably members of the family Cucurbitaceae, which includes the common pumpkins and gourds — produce and which function as a defence against herbivores. Cucurbitacins are chemically classified as triterpenes, formally derived from cucurbitane, a triterpene hydrocarbon—specifically, from the unsaturated variant cucurbita-5-ene, or 19-(10→9β)-abeo-10α-lanost-5-ene. They often occur as glycosides. They and their derivatives have been found in many plant families, in some mushrooms and even in some marine mollusks.

Flavan-4-ol chemical compound

The flavan-4-ols (3-deoxyflavonoids) are flavone-derived alcohols and a family of flavonoids. Flavan-4-ols are colorless precursor compounds that polymerize to form red phlobaphene pigments. They can be found in the sorghum. Glycosides can be isolated from a methanol extract of the rhizomes of Abacopteris penangiana.

Momordicin I

Momordicin I, or 3,7,23-trihydroxycucurbitan-5,24-dien-19-al, is a chemical compound found in the leaves of the bitter melon vine, possibly responsible for its reputed medicinal properties.

Momordenol chemical compound

Momordenol or 3β-hydroxy-stigmasta-5,14-dien-16-one is a natural chemical compound, a sterol found in the fresh fruit of the bitter melon.

Balsaminapentaol chemical compound

Balsaminapentaol or cucurbita-5,25-diene-3β,7β,23(R),24(R),29-pentaol, is a chemical compound with formula C
30H
50O
5, found in the Balsam apple vine. It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.

Balsaminol A chemical compound

Balsaminol A or cucurbita-5,24-diene-3β,7β,23(R),29-tetraol, is a chemical compound with formula C
30H
50O
4, found in the Balsam apple vine. It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.

Balsaminol B chemical compound

Balsaminol B or 7β-methoxycucurbita-5,24-diene-3β,23(R),29-triol, is a chemical compound with formula C
31H
52O
4, found in the balsam apple vine. It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.

Cucurbalsaminol A chemical compound

Cucurbalsaminol A or cucurbita-5,23(E)-diene-3β,12β,25-triol, is a chemical compound with formula C
30H
50O
4, found in the Balsam apple vine. It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.

Cucurbalsaminol B chemical compound

Cucurbalsaminol B or 7β-methoxycucurbita-5,23(E)-diene-3β,12β,25-triol, is a chemical compound with formula C
31H
52O
4, found in the Balsam apple vine. It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.

<i>Momordica foetida</i> species of plant

Momordica foetida is a perennial climbing vine native of tropical Africa, closely related to the bitter melon and balsam apple. Its species name ("bad-smelling") refers to its unpleasant smell. It was previously named M. morkorra and M. cordata (Cogn.)

Charantin is a chemical substance obtained from the Asian bitter melon, 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 African species M. foetida, by A. Olaniyi in 1975, under the name foetidin.

Momordin is one of several saponins derived from oleanolic acid, a triterpenoid. These chemical compounds are found in some plants of the genus Momordica, which includes the bitter melon and the balsam apple, as well as in other Asian herbal medicine plants such as Kochia scoparia and Ampelopsis radix.

Cucurbitane chemical compound

Cucurbitane is a chemical compound with formula C
30H
54. It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of lanostane, from which it differs by the formal shift of a methyl group from the 10 to the 9β position in the standard steroid numbering scheme.

A kuguaglycoside is one of several chemical compounds isolated from the roots of the bitter melon vine by J.-C. Chen and others.

A kuguacin is one of several chemical compounds isolated from the bitter melon vine by J.-C. Chen and others.

A momordicine is any of several compounds found the bitter melon vine, Momordica charantia. They are glycosides of cucurbitane derivatives. They include

Neokuguaglucoside chemical compound

Neokuguaglucoside is a chemical compound with formula C
42H
66O
14, isolated from the fruit of the bitter melon vine, where it occurs at 23 mg/35 kg. It is a triterpene glucoside with the cucurbitane skeleton. It is a white powder, soluble in methanol and butanol.

Endecaphyllacin is either of two similar compounds found in certain plants, such as Hemsleya endecaphylla.

<i>Paullinia pinnata</i> species of plant

Paullinia pinnata is a flowering plant species in the genus of Paullinia found in South America and Africa.

References

  1. 1 2 Akihisa T, Higo N, Tokuda H, Ukiya M, Akazawa H, Tochigi Y, Kimura Y, Suzuki T, Nishino H, et al. (2007). "Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects". Journal of Natural Products. 70 (8): 1233–1239. doi:10.1021/np068075p. PMID   17685651.
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