Cucurbitane

Cucurbitane

Identifiers
CAS Registry Number	65441-59-0 (5α/β) Y
ChEBI	CHEBI:73169 Y
Jmol-3D images	Image (5α) Image (5β)
SMILES C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C (5α) C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C (5β)
Properties
Molecular formula	C30H54
Molar mass	414.75 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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.^[1][2]

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).^[1]

• 

  5α-Cucurbitane

• 

  5β-Cucurbitane

Derivatives

Natural compounds

Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals,^[3] Natural cucurbitane-related compounds include:

Named

• Balsaminapentaol, from Momordica balsamina.^[4]
• Balsaminol A, from Momordica balsamina.^[4]
• Balsaminol B, from Momordica balsamina.^[4]
• Brydioside A from Bryonia dioica ^[3]:64
• Bryoamaride and derivatives from Bryonia dioica ^[3]:65,66
• Charantin or foetidin, from Momordica charantia^[5] and Momordica foetida^[6]
• Charantosides I-VIII, from Momordica charantia.^[7]
• Cucurbalsaminol B, from Momordica balsamina.^[4]
• Cucurbalsaminol A, from Momordica balsamina.^[4]
• Cucurbitacins A-L, O-T ^{[3][8] [9]:3–8}
• Datiscosides, from Datisca glomerata ^[3]:16–19
• Endecaphyllacins A and B, from roots of Hemsleya endecaphylla ^[9]:1,2
• Hemslecins A and B, from roots of H. endecaphylla ^[9]
• Lepidolide, from the mushroom Russula lepida ^[10]
• Karavilagenin E, from Momordica balsamina.^[4]
• Khekadaengosides A, B, D and K, from Trichosanthes tricuspidata ^{[3]:57,58,67,68}
• Kuguacins A-S, from stems and leaves of Momordica charantia^[11][12]
• Kuguaglycosides A-H, from the root of Momordica charantia^[13]
• Mogrosides I-V, from the fruits of Siraitia grosvenorii ^[14]
• Momordicin I, II and 28, from Momordica charantia^[15][16]
• Momordicines II and IV, from leaves of Momordica charantia ^[17]
• Momordicosides A-S, from Momordica charantia fruits ^[7][18][19]
• Neokuguaglucoside, from Momordica charantia fruits ^[20]
• Neomogroside, from the fruit of Siraitia grosvenorii.^[21]
• Pentanorcucurbitacins A and B ^[22]:1,2
• Perseapicroside A, from Persea mexicana ^[3]:44
• Scandenoside R9, from Hemsleya panacis-scandens ^[3]:45
• Spinosides A and B, from Desfontainia spinosa ^[3]: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.^[23]:1
• 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica foetida^[23]:2
• 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida^[23]:3
• 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica foetida^[23]:4
• 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida^[23]: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^[23]:6
• 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida^[23]:7
• 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica foetida^[23]:8

• 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside, C
  40H
  66O
  9, white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 kg)^[18]:1
• 23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside,C
  42H
  69O
  14, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)^[18]:2
• 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside, C
  48H
  82O
  19, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)^[18]: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) ^[8]: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)^[8]:4

• 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina ^[24]

• 25,26,27-trinorcucurbit-5-ene-3,7,23-trione C
  27H
  40O
  3, white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)^[22]:3

See also

• Goyaglicoside
• Karaviloside
• Momordenol, from Momordica charantia^[15]
• 24(R)-stigmastan-3β,5α,6β-triol-25-ene 3-O-β-glucopyranoside, C
  35H
  60O
  8, white powder, from Momordica charantia fruit (15 mg/35 kg)^[18]:4

References