Cucurbitane
Encyclopedia
Cucurbitane is a chemical compound
with formula (CAS
number 65441-59-0). It is a polycyclic hydrocarbon
, specifically a triterpene
. It is an isomer of lanostane
(specifically 19(10→9β)abeo-lanostane), from which it differs by the formal shift of a methyl group (carbon
number 19) from the 10 to the 9β position in the standard steroid
numbering scheme.
The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β, which differ by the handedness of the bonds at a particular carbon
atom (number 5 in the standard steroid numbering scheme).
, Natural cucurbitane-related compounds include:
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with formula (CAS
Chemical Abstracts Service
Chemical Abstracts is a periodical index that provides summaries and indexes of disclosures in recently published scientific documents. Approximately 8,000 journals, technical reports, dissertations, conference proceedings, and new books, in any of 50 languages, are monitored yearly, as are patent...
number 65441-59-0). It is a polycyclic hydrocarbon
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
, specifically a triterpene
Triterpene
Triterpenes are terpenes consisting of six isoprene units and have the molecular formula C30H48.The pentacyclic triterpenes can be classified into lupane, oleanane or ursane groups.Animal- and plant-derived triterpenes exist, such as:*squalene...
. It is an isomer of lanostane
Lanostane
Lanostane or 4,4,14-trimethylcholestane is a chemical compound with formula . It is a polycyclic hydrocarbon, specifically a triterpene...
(specifically 19(10→9β)abeo-lanostane), from which it differs by the formal shift of a methyl group (carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
number 19) from the 10 to the 9β position in the standard 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...
numbering scheme.
The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β, which differ by the handedness of the bonds at a particular carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...
atom (number 5 in the standard steroid numbering scheme).
Natural compounds
Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticalsPhytomedicine
Phytomedicine is a peer-reviewed scientific journal publishing in the fields of phytopharmacology, phytotherapy and phytotoxicology. The journal was first published in 1994. Its editor-in-chief is Hildebert Wagner....
, Natural cucurbitane-related compounds include:
Named
- BalsaminapentaolBalsaminapentaolBalsaminapentaol or cucurbita-5,25-diene-3β,7β,23,24,29-pentaol, is a chemical compound with formula , found in the Balsam apple vine . It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C...
, from Momordica balsaminaMomordica balsaminaMomordica 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...
. - Balsaminol ABalsaminol ABalsaminol A or cucurbita-5,24-diene-3β,7β,23,29-tetraol, is a chemical compound with formula , 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 is an amorphous powder soluble in methanol and...
, from Momordica balsamina. - Balsaminol BBalsaminol BBalsaminol B or 7β-methoxycucurbita-5,24-diene-3β,23,29-triol, is a chemical compound with formula , 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 is an amorphous powder soluble in methanol...
, from Momordica balsamina. - Brydioside ABrydiosideBrydioside 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....
from Bryonia dioica - BryoamarideBryoamarideBryoamaride 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....
and derivatives from Bryonia dioicaBryonia dioicaBryonia dioica, known by the common names red bryony and white bryony, is a perennial climbing vine indigenous to Central and Southern Europe. It is a flowering plant of the genus Bryonia with five-pointed leaves and blue or white flowers. The vine produces a red berry fruit.-Medicinal use:A...
- CharantinCharantinCharantin 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...
or foetidin, from Momordica charantia and Momordica foetida - Charantosides I-VIIICharantosideCharantoside 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....
, from Momordica charantia. - Cucurbalsaminol BCucurbalsaminol BCucurbalsaminol B or 7β-methoxycucurbita-5,23-diene-3β,12β,25-triol, is a chemical compound with formula , found in the Balsam apple vine . It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C...
, from Momordica balsamina. - Cucurbalsaminol ACucurbalsaminol ACucurbalsaminol A or cucurbita-5,23-diene-3β,12β,25-triol, is a chemical compound with formula , 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 is an amorphous powder soluble in...
, from Momordica balsamina. - Cucurbitacins A-L, O-TCucurbitacinCucurbitacin is any of a class of biochemical compounds that some plants — notably members of the family Cucurbitaceae, that includes the common pumpkins and gourds — developed in order to defend themselves from herbivores...
- DatiscosideDatiscosideDatiscoside 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.They include...
s, from Datisca glomerataDatisca glomerataDatisca glomerata is a species of plant native to California, Nevada, and Baja California known by the common name Durango root. It is one of only two to four species in the plant family Datiscaceae. It is an erect perennial herb with distinctive long, pointed, often sharply serrated leaves. It is...
- Endecaphyllacins A and BEndecaphyllacinEndecaphyllacin is either of two similar compounds found in certain plants, such as Hemsleya endecaphylla. * Endecaphyllacin A, 2β-hydroxy-20,21,22,23,24,25,26,27-octanorcucurbita-5-ene-3,11,16-trione, . Crystallizes with 1 molecule of methanol as colorless prisms, mp 207-209 °C; * Endecaphyllacin...
, from roots of Hemsleya endecaphylla - Hemslecins A and BHemslecinHemslecin 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.The hemslecins include:...
, from roots of H. endecaphylla - LepidolideLepidolideLepidolide is a chemical compound with formula — specifically, a terpenoid with the cucurbitane skeleton — isolated from the fruiting bodies of the mushroom Russula lepida . It is a pale yellow oil, soluble in chloroform....
, from the mushroom Russula lepida - Karavilagenin EKaravilagenin EKaravilagenin E is a chemical compound found in the Balsam apple vine . It is a cucurbitane-type triterpenoid, related to cucurbitacin.Karavilagenin E is soluble in methanol and ethyl acetate but insoluble in n-hexane....
, from Momordica balsamina. - Khekadaengosides A, B, D and KKhekadaengosideKhekadaengoside 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....
, from Trichosanthes tricuspidata - Kuguacins A-SKuguacinA kuguacin is one of several chemical compounds isolated from the bitter melon vine by J.-C. Chen and others.Kuguacins are cucurbitacins, formally derived from the triterpene hydrocarbon cucurbitane...
, from stems and leaves of Momordica charantia - Kuguaglycosides A-HKuguaglycosideA kuguaglycoside is one of several chemical compounds isolated from the roots of the bitter melon vine by J.-C. Chen and others....
, from the root of Momordica charantia - Mogrosides I-VMogrosideA mogroside is any of several chemical compounds found in certain plants, such as the fruit of the gourd vine luo han guo . They are glycosides of cucurbitane derivatives...
, from the fruits of Siraitia grosvenoriiSiraitia grosvenoriiSiraitia grosvenorii is an herbaceous perennial vine native to southern China and Northern Thailand. The plant is best known for its fruit, commonly called luo han guo or luo han kuo , la han qua , arhat fruit, Buddha... - Momordicin I, II and 28MomordicinMomordicin is one of several compounds found in the bitter melon vine, including:* Momordicin I foundin the leaves.* Momordicin II* Momordicin-28...
, from Momordica charantia - Momordicines II and IVMomordicineA momordicine is any of several compounds found the bitter melon vine, Momordica charantia. They are glycosides of cucurbitane derivatives. They include* Momordicine II...
, from leaves of Momordica charantia - Momordicosides A-SMomordicosideMomordicoside 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...
, from Momordica charantia fruits - NeokuguaglucosideNeokuguaglucosideNeokuguaglucoside is a chemical compound with formula , 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....
, from Momordica charantia fruits - NeomogrosideNeomogrosideNeomogroside is a cucurbitane glycoside isolated from the fruit of Siraitia grosvenorii....
, from the fruit of Siraitia grosvenoriiSiraitia grosvenoriiSiraitia grosvenorii is an herbaceous perennial vine native to southern China and Northern Thailand. The plant is best known for its fruit, commonly called luo han guo or luo han kuo , la han qua , arhat fruit, Buddha...
. - Pentanorcucurbitacins A and BCucurbitacinCucurbitacin is any of a class of biochemical compounds that some plants — notably members of the family Cucurbitaceae, that includes the common pumpkins and gourds — developed in order to defend themselves from herbivores...
- Perseapicroside APerseapicrosidePerseapicroside 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.They include...
, from Persea mexicana - Scandenoside R9ScandenosideScandenoside 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.They include...
, from Hemsleya panacis-scandens - Spinosides A and BSpinosideSpinoside 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.They include...
, from Desfontainia spinosa
Unnamed
- 3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123-125°C, from Momordica charantia, Momordica foetidaMomordica foetidaMomordica 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...
. - 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188-191°C, from Momordica charantia, Momordica foetida
- 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida
- 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182-184°C, from Momordica foetida
- 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida
- 5β,19-epoxy-19-methoxycucurbita-6,23-dien-3β,25-diol, soluble in chloroform, melts at 102-104°C, from Momordica charantia, Momordica foetida
- 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida
- 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139-141°C, from Momordica charantia, Momordica foetida
- 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside, , white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 kg)
- 23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside,, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)
- 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside, , white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)
- 2,16-dihydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 2-O-β-D-glucopyranoside, soluble in ethanol, from Cucurbita pepo fruits (25 mg/15 kg)
- 16-hydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside, white powder, soluble in ethanol, from Cucurbita pepo fruits (12 mg/15 kg)
- 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina
- 25,26,27-trinorcucurbit-5-ene-3,7,23-trione , white powder, soluble in methanolMethanolMethanol, 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...
, from stems of Momordica charantia (6 mg/18 kg)
See also
- Goyaglicoside
- KaravilosideKaravilosideKaraviloside is any of several related glycosides found in bitter melon vine . They include:* Karaviloside I* Karaviloside II* Karaviloside III* Karaviloside V* Karaviloside XI...
- MomordenolMomordenolMomordenol or 3β-hydroxy-stigmasta-5,14-dien-16-one is a natural chemical compound, a sterol with formula , found in the fresh fruit of the bitter melon ....
, from Momordica charantia - 24(R)-stigmastan-3β,5α,6β-triol-25-ene 3-O-β-glucopyranoside, , white powder, from Momordica charantia fruit (15 mg/35 kg)