Charantin

Last updated

Charantin is a chemical substance obtained from the Asian bitter melon (Momordica charantia), reputed to be responsible for the hypoglycaemic properties of those plants. It was identified by Lolitkar and Rao in 1960. [1] [2] It was also found in the similar African species M. foetida , by A. Olaniyi in 1975, under the name foetidin. [3]

Charantin is actually a 1:1 mixture of two steroidal saponins, β-sitosteryl glucoside (C
35
H
60
O
6
) and 5,22-stigmasteryl glucoside (C
35
H
58
O
6
). [3] It is a whitish crystalline substance, neutral and tasteless, melting at 266–268 °C. It is sparingly soluble in water [1] 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. [4]

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. [5]

See also

Related Research Articles

<i>Momordica charantia</i> Bitter melon, tropical & subtropical

Momordica charantia is a tropical and subtropical vine of the family Cucurbitaceae, widely grown in Asia, Africa, and the Caribbean for its edible fruit. Its many varieties differ substantially in the shape and bitterness of the fruit.

<span class="mw-page-title-main">Cucurbitacin</span> Class of biochemical compounds

Cucurbitacins are a class of biochemical compounds that some plants – notably members of the pumpkin and gourd family, Cucurbitaceae – produce and which function as a defense against herbivores. Cucurbitacins and their derivatives have also been found in many other plant families, in some mushrooms and even in some marine mollusks.

<span class="mw-page-title-main">Extraction (chemistry)</span> Separation of a desired substance from other substances in the sample

Extraction in chemistry is a separation process consisting of the separation of a substance from a matrix. The distribution of a solute between two phases is an equilibrium condition described by partition theory. This is based on exactly how the analyte moves from the initial solvent into the extracting solvent. The term washing may also be used to refer to an extraction in which impurities are extracted from the solvent containing the desired compound.

<span class="mw-page-title-main">Momordicin I</span> Chemical compound

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.

<span class="mw-page-title-main">Momordicin-28</span> Chemical compound

Momordicin-28 or 13-hydroxy-28-methoxy-urs-11-en-3-one is a triterpene compound with formula C
31
H
50
O
3
found in the fresh fruit of the bitter melon.

<span class="mw-page-title-main">Momordicinin</span> Chemical compound

Momordicinin (13β,28-epoxy-urs-11-en-3-one) is chemical compound, a triterpene with formula C
30
H
46
O
2
, found in the fresh fruit of the bitter melon.

<span class="mw-page-title-main">Momordicilin</span> Chemical compound

Momordicilin or 24-[1′-hydroxy,1′-methyl-2′-pentenyloxyl]-ursan-3-one is a chemical compound, a triterpenoid with formula C
36
H
60
O
3
, found in the fresh fruit of the bitter melon.

<span class="mw-page-title-main">Momordenol</span> Chemical compound

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

<span class="mw-page-title-main">Momordol</span> Chemical compound

Momordol or 1-hydroxy-1,2-dimethyl-2-[8′,10′-dihydroxy-4′,7′-dimethyl-11′-hydroxy methyl-trideca]-3-ethyl-cyclohex-5-en-4-one is a chemical compound with formula C
26
H
48
O
5
, found in the fresh fruit of the bitter melon.

Charantoside is any of several related cucurbitane triterpenoid glycosides found in the fruits bitter melon vine. They include:

Goyaglycoside is any of several related triterpenoid glycosides found in the fruits bitter melon vine, called goya in Okinawan language. They include:

<span class="mw-page-title-main">15,16-Dihydroxy-α-eleostearic acid</span> Chemical compound

15,16-Dihydroxy-α-eleostearic acid, or 15,16-Dihydroxy-(9Z,11E,13E)-9,11,13-octadecatrienoic acid, is an organic compound with formula C
18
H
30
O
4
, or H3C-CH2-(-CH(OH)-)2(-CH=CH-)3-(-CH2-)7-(C=O)OH. It can be seen as derived from α-eleostearic acid by the replacement of two hydrogen atoms by two hydroxyl (OH) groups.

<i>Momordica foetida</i> Species of flowering 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.)

<i>Momordica cymbalaria</i> Species of flowering plant

Momordica cymbalaria is a vine of the genus Momordica found in the Indian states of Andhra Pradesh, Karnataka, Madhya Pradesh, Maharashtra, and Tamil Nadu. It is a relative of the bitter melon plant. The plant has also been named Luffa tuberosa (Roxb.) or Momordica tuberosa (Roxb.)

<span class="mw-page-title-main">Momordin (protein)</span>

Momordin or α-momorcharin is one of several related proteins isolated from several plants of the genus Momordica, which includes the bitter melon and the balsam apple.

<span class="mw-page-title-main">Cucurbitane</span> Chemical compound

Cucurbitane is a class of tetracyclic chemical compounds with formula C
30
H
54
. It is a polycyclic hydrocarbon, specifically triterpene. It is also 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.

<span class="mw-page-title-main">Neokuguaglucoside</span> Chemical compound

Neokuguaglucoside is a chemical compound with formula C
42
H
66
O
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.

Concrete, in perfumery, is a waxy mass obtained by solvent extraction of fresh plant material. It is usually used for the production of absolutes.

References

  1. 1 2 M. M. Lolitkar and M. R. Rajarama Rao (1962). "Note on a Hypoglycaemic Principle Isolated from the fruits of Momordica charantia". Journal of the University of Bombay. 29: 223–224.
  2. Raman, A.; Lau, C. (1996). "Anti-diabetic properties and phytochemistry of Momordica charantia L. (Cucurbitaceae)". Phytomedicine. 2 (4): 349–62. doi:10.1016/S0944-7113(96)80080-8. PMID   23194773.
  3. 1 2 Olaniyi, A. A. (1975). "A neutral constituent of Momordica foetida". Lloydia. 38 (4): 361–362. PMID   1186439.
  4. Pitipanapong, J.; Chitprasert, S.; Goto, M.; Jiratchariyakul, W.; Sasaki, M.; Shotipruk, A. (2007). "New approach for extraction of charantin from Momordica charantia with pressurized liquid extraction". Separation and Purification Technology. 52 (3): 416. doi:10.1016/j.seppur.2005.11.037.
  5. Parkash, A.; Ng, T. B.; Tso, W. W. (2002). "Purification and characterization of charantin, a napin-like ribosome-inactivating peptide from bitter gourd (Momordica charantia) seeds". The Journal of Peptide Research. 59 (5): 197–202. doi: 10.1034/j.1399-3011.2002.00978.x . PMID   11966976.