Karaviloside

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Karaviloside is any of several related cucurbitane triterpenoid glycosides found in bitter melon vine (Momordica charantia). [1] [2] [3] 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.

Karavilosides I, II, and III can be extracted from the M. charantia fruit with methanol. [1] [3] Karavilosides III, V, and XI can be extracted from the M. charantia roots by methanol. [2]

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.

See also

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:

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

Related Research Articles

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.

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.

Momordicin is one of several compounds found in the bitter melon vine, including:

Momordicoside is any of several related cucurbitane triterpenoid glycosides that can be extracted from the bitter melon vine (Momordica charantia). They include:

Cucurbitane chemical compound

Cucurbitane is a chemical compound with formula C
30
H
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 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 in 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
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.

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

Hemslecin is any of several compounds obtained from plants of the Helmseya genus, which are used in Asian folk medicine. They are triterpene derivatives, specifically with the cucurbitane skeleton, related to cucurbitacin F.

Perseapicroside is any one of several chemical compounds isolated from certain plants, notably Persea mexicana. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacin F.

Scandenoside is any one of several chemical compounds isolated from certain plants, notably Hemsleya panacis-scandens. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacin F.

Datiscoside is any one of several chemical compounds isolated from certain plants, notably Datisca glomerata. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacin F.

Khekadaengoside is any one of several chemical compounds isolated from certain plants, notably Trichosanthes tricuspidata. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacins H and L.

Spinoside is any one of several chemical compounds isolated from certain plants, notably Desfontainia spinosa. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacin H.

Brydioside is any one of several chemical compounds isolated from certain plants, notably Bryonia dioica. They can be seen as derivatives of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacin Lor 23,24-dihydrocucurbitacin I.

Bryoamaride chemical compound

Bryoamaride is a chemical compound isolated from certain plants, notably Bryonia dioica. It can be seen as a derivative of the triterpene hydrocarbon cucurbitane, more specifically from cucurbitacin L or 23,24-dihydrocucurbitacin I.

References

  1. 1 2 3 Toshihiro Akihisa, Naoki Higo, Harukuni Tokuda, Motohiko Ukiya, Hiroyuki Akazawa, Yuichi Tochigi, Yumiko Kimura, Takashi Suzuki, and Hoyoku Nishino (2007), "Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects". Journal of Natural Products, volume 70, pages 1233-1239. doi : 10.1021/np068075p
  2. 1 2 3 4 5 Jian-Chao Chen, Lu Lu, Xian-Ming Zhang, Lin Zhou, Zhong-Rong Li, and Ming-Hua Qiu (2008), "Eight New Cucurbitane Glycosides, Kuguaglycosides A–H, from the Root of Momordica charantia L.". Helvetica Chimica Acta, volume 91, issue 5, pages 920-928. doi : 10.1002/hlca.200890097
  3. 1 2 3 4 Jie-Qing Liu, Jian-Chao Chen, Cui-Fang Wang and Ming-Hua Qiu (2009), "New Cucurbitane Triterpenoids and Steroidal Glycoside from Momordica charantia". Molecules, volume 14, pages 4804-4813 doi : 10.3390/molecules14124804