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Cucurbitane is a
tetracyclic Tetracyclics are cyclic compound, cyclic chemical compounds that contain four fused ring (chemistry), rings of atoms, for example, Tröger's base. Some tricyclic compounds having three fused and one tethered ring (connected to main nucleus by ...
chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...
with formula . It is a polycyclic
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
, specifically
triterpene Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...
. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of a
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
group (
carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
number 19) from the 10 to the 9β position in the standard
steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...
numbering scheme.Satish Kumar and Raj Kumar (1991), ''Dictionary of Biochemistry''. Anmol Publications, India The name is applied to two
stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
s, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular
carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
atom (number 5 in the standard steroid numbering scheme). File:5alpha-cucurbitane.svg, 5α-Cucurbitane File:5beta-cucurbitane.svg, 5β-Cucurbitane Cucurbitane is the core chemical structure of a class of derivatives known as cucurbitane-type triterpenoids or simply as cucurbitanes.


Derivatives


Natural compounds

Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals. Natural cucurbitane-related compounds include:


Named

* Balsaminapentaol, from '' Momordica balsamina''. * Balsaminol A, from ''Momordica balsamina''. * Balsaminol B, from ''Momordica balsamina''. * Brydioside A from ''Bryonia dioica'' * Bryoamaride and derivatives from ''
Bryonia dioica ''Bryonia dioica'', known by the common names red bryony and white bryony, also English mandrake or ladies' seal, is a perennial climbing vine indigenous to Central and Southern Europe. It is a flowering plant in the cucumber family Cucurbitac ...
'' * Charantin or foetidin, from ''
Momordica charantia ''Momordica charantia'' (commonly called bitter melon, cerassee, goya, bitter apple, bitter gourd, bitter squash, balsam-pear, karela, karavila and many more names listed below) is a tropical and subtropical vine of the family Cucurbitaceae, w ...
'' and ''Momordica foetida'' * Charantosides I-VIII, from ''Momordica charantia''. * Cucurbalsaminol B, from ''Momordica balsamina''. * Cucurbalsaminol A, from ''Momordica balsamina''. * Cucurbitacins A-L, O-T * Datiscosides, from '' Datisca glomerata'' * Endecaphyllacins A and B, from roots of '' Hemsleya endecaphylla'' * Hemslecins A and B, from roots of ''H. endecaphylla'' *
Lepidolide Lepidolide is a chemical compound with formula — specifically, a terpenoid with the cucurbitane skeleton — isolated from the fruiting bodies of the mushroom '' Russula lepida'' (23 mg/7 kg). It is a pale yellow oil, soluble in chlor ...
, from the mushroom ''
Russula lepida ''Russula rosea'' (synonym ''Russula lepida''), known as the rosy russula, is a north temperate, commonly found mushroom of the large "brittlegill" genus '' Russula''. The cap is convex when young, later flat, mostly bright cinnabar to carmine r ...
''Jian-Wen Tan, Ze-Jun Dong, Zhi-Hui Ding and Ji-Kai Liu (2002)
"Lepidolide, a Novel Seco-ring-A Cucurbitane Triterpenoid from ''Russula lepida'' (Basidiomycetes)"
''Zeitschrift für Naturforschung'' Series C, volume 57C issue 11/12, pages 963-965.
* Karavilagenin E, from ''Momordica balsamina''. * Khekadaengosides A, B, D and K, from ''
Trichosanthes tricuspidata ''Trichosanthes tricuspidata'' is a climbing plant in the family Cucurbitaceae. Subspecies The following subspecies are listed in the Catalogue of Life: * ''T. t. asperifolia'' * ''T. t. seramensis'' * ''T. t. siberutensis'' * ''T. t. javanica ...
'' * Kuguacins A-S, from stems and leaves of ''Momordica charantia'' * Kuguaglycosides A-H, from the root of ''Momordica charantia'' * Mogrosides I-V, from the fruits of '' Siraitia grosvenorii'' * Momordicin I, II and 28, from ''Momordica charantia'' * Momordicines II and IV, from leaves of ''Momordica charantia''Daniel Bisrat Mekuria, Takehiro Kashiwagi, Shin-ichi Tebayashi, and Chul-Sa Kim (2006)"Cucurbitane Glucosides from ''Momordica charantia'' Leaves as Oviposition Deterrents to the Leafminer, ''Liriomyza trifolii''". ''Z. Naturforsch.'', volume 61c, pages 81–86 * Momordicosides A-S, from ''Momordica charantia'' fruits * Neokuguaglucoside, from ''Momordica charantia'' fruits * Neomogroside, from the fruit of '' Siraitia grosvenorii''. * Pentanorcucurbitacins A and B * Perseapicroside A, from '' Persea mexicana'' * Scandenoside R9, from '' Hemsleya panacis-scandens'' * Spinosides A and B, from ''
Desfontainia spinosa ''Desfontainia'' is a genus of flowering plants in the family Columelliaceae, though it was placed formerly in Loganiaceae, Potaliaceae (later subsumed in Gentianaceae), or a family of its own, Desfontainiaceae. The genus was named for the Fr ...
''


Unnamed

* 3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123−125 °C, from ''Momordica charantia'', '' Momordica foetida''. * 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'' * , , 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''--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 ''Cucurbita pepo'' is a cultivated plant of the genus ''Cucurbita''. It yields varieties of winter squash and pumpkin, but the most widespread varieties belong to the subspecies ''Cucurbita pepo'' subsp. ''pepo'', called summer squash. It has b ...
'' 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
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic Alcohol (chemistry), alcohol, with the chemical formula (a methyl group linked to a hydroxyl group, often ab ...
, from stems of ''Momordica charantia'' (6 mg/18 kg)


See also

*
Goyaglicoside Goyaglycoside is any of several related triterpenoid glycosides found in the fruits bitter melon vine (''Momordica charantia''), called ''goya'' in Okinawan language. They include: * goyaglycoside c. * goyaglycoside d. Goyaglycosides c and d can b ...
*
Karaviloside Karaviloside is any of several related cucurbitane triterpenoid glycosides found in bitter melon vine (''Momordica charantia'').Toshihiro Akihisa, Naoki Higo, Harukuni Tokuda, Motohiko Ukiya, Hiroyuki Akazawa, Yuichi Tochigi, Yumiko Kimura, Takashi ...
* Momordenol, 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)


References

{{Tetracyclics Lanostanes Triterpenes