Cucurbitane

Cucurbitane is a class of chemical compounds with formula (CAS number 65441-59-0). It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), 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.Satish Kumar and Raj Kumar (1991), ''Dictionary of Biochemistry''. Anmol Publications, India

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).

File:5alpha-cucurbitane.svg, 5α-Cucurbitane
File:5beta-cucurbitane.svg, 5β-Cucurbitane

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''
* Charantin or foetidin, from ''Momordica charantia'' 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, from the mushroom '' Russula lepida''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''
* 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''

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'' 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, from stems of ''Momordica charantia'' (6 mg/18 kg)

See also

* Goyaglicoside
* Karaviloside
* 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

{{reflist, 2

Lanostanes
Triterpenes