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Chemical compound

Cucurbitane

Cucurbitane
5α-Cucurbitane
5α-Cucurbitane
5β-Cucurbitane
5β-Cucurbitane
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Cucurbitane is a tetracyclic chemical compound with formula C
30
H
54
. 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).

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

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
  • 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)
  • 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)
  • 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)
  • 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 C
    27
    H
    40
    O
    3
    , white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)

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Text from Wikipedia, CC BY-SA 4.0 · Source article