Cucurbitane

Cucurbitane is a tetracyclic chemical compound with formula. 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.
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.
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
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
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
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
[cucurbita-6,23-diene|],, white powder soluble in methanol, from Momordica charantia fruit
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
23(R),24(S),25-trihydroxycucurbit-5-ene 3-O--25-O-β-glucopyranoside,, white powder soluble in methanol, from Momordica charantia fruit
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
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
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''