Cucurbitane
# Cucurbitane

Cucurbitane is a class of tetracyclic chemical compounds with formula C $_{30}H$ $_{54}$ (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.

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).

* 5α-Cucurbitane
* 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 $dioica^{:64}$
* Bryoamaride and derivatives from Bryonia $dioica^{:65,66}$
* 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, $O-T^{:3–8}$
* Datiscosides, from Datisca $glomerata^{:16–19}$
* Endecaphyllacins A and B, from roots of Hemsleya $endecaphylla^{:1,2}$
* 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 $tricuspidata^{:57,58,67,68}$
* 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 $B^{:1,2}$
* Perseapicroside A, from Persea $mexicana^{:44}$
* Scandenoside R9, from Hemsleya $panacis-scandens^{:45}$
* Spinosides A and B, from Desfontainia $spinosa^{:61,62}$

**Unnamed**

* 3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123−125 °C, from Momordica charantia, Momordica $foetida.^{:1}$
* 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica $foetida^{:2}$
* 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica $foetida^{:3}$
* 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica $foetida^{:4}$
* 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica $foetida^{:5}$
* 5β,19-epoxy-19-methoxycucurbita-6,23-dien-3β,25-diol, soluble in chloroform, melts at 102−104 °C, from Momordica charantia, Momordica $foetida^{:6}$
* 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica $foetida^{:7}$
* 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica $foetida^{:8}$
* 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside, C $_{40}H$ $_{66}O$ $_9,$ white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 $kg)^{:1}$
* 23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside,C $_{42}H$ $_{69}O$ $_{14},$ white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 $kg)^{:2}$
* 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside, C $_{48}H$ $_{82}O$ $_{19},$ white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 $kg)^{:3}$
* 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 $kg)^{:3}$
* 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 $kg)^{:4}$
* 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina
* 25,26,27-trinorcucurbit-5-ene-3,7,23-trione C $_{27}H$ $_{40}O$ $_3,$ white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 $kg)^{:3}$
