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Cucurbitane

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Cucurbitane is a chemical compound with formula C
30H
54 (CAS number 65441-59-0). It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of lanostane (specifically 19(10→9β)abeo-lanostane), 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.

Contents

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).

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
  • 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)

    • References

    Cucurbitane Wikipedia
    (Text) CC BY-SA