Cucurbitane

Cucurbitane is a tetracyclic chemical compound with formula C
₃₀H
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.^[1][2]

Cucurbitane

Names
IUPAC name 19-Nor-5ξ,9β,10α-lanostane
Systematic IUPAC name (1R,3aS,3bR,5aΞ,9aR,9bS,11aR)-3a,6,6,9b,11a-Pentamethyl-1-[(2R)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	65441-59-0 (5α/β) Y
3D model (JSmol)	(5α): Interactive image (5β): Interactive image
ChEBI	CHEBI:73245 N
ChemSpider	25936933 (5α) N 28639243 (5β) N
PubChem CID	71306377
UNII	VQU8QE865A Y
CompTox Dashboard (EPA)	DTXSID50745373
InChI InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 N Key: ZYZJWAJOTPNVPI-AUAIAXQGSA-N N (5α): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-AUAIAXQGBW (5β): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-QJMYWHNVBB (5β): InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1 Key: ZYZJWAJOTPNVPI-QJMYWHNVSA-N
SMILES (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): 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
Properties
Chemical formula	C30H54
Molar mass	414.762 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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

Cucurbitane is the core chemical structure of a class of derivatives known as cucurbitane-type triterpenoids or simply as cucurbitanes.^[3]

Derivatives

Natural compounds

Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals.^[4] Natural cucurbitane-related compounds include:

Named

• Balsaminapentaol, from Momordica balsamina.^[5]
• Balsaminol A, from Momordica balsamina.^[5]
• Balsaminol B, from Momordica balsamina.^[5]
• Brydioside A from Bryonia dioica^[4]: 64
• Bryoamaride and derivatives from Bryonia dioica^{[4]: 65, 66}
• Charantin or foetidin, from Momordica charantia^[6] and Momordica foetida^[7]
• Charantosides I-VIII, from Momordica charantia.^[8]
• Cucurbalsaminol B, from Momordica balsamina.^[5]
• Cucurbalsaminol A, from Momordica balsamina.^[5]
• Cucurbitacins A-L, O-T^{[4][9][10]: 3–8}
• Datiscosides, from Datisca glomerata^{[4]: 16–19}
• Endecaphyllacins A and B, from roots of Hemsleya endecaphylla^{[10]: 1, 2}
• Hemslecins A and B, from roots of H. endecaphylla^[10]
• Lepidolide, from the mushroom Russula lepida^[11]
• Karavilagenin E, from Momordica balsamina.^[5]
• Khekadaengosides A, B, D and K, from Trichosanthes tricuspidata^{[4]: 57, 58, 67, 68}
• Kuguacins A-S, from stems and leaves of Momordica charantia^[12][13]
• Kuguaglycosides A-H, from the root of Momordica charantia^[14]
• Mogrosides I-V, from the fruits of Siraitia grosvenorii^[15]
• Momordicin I, II and 28, from Momordica charantia^[16][17]
• Momordicines II and IV, from leaves of Momordica charantia^[18]
• Momordicosides A-S, from Momordica charantia fruits^[8][19][20]
• Neokuguaglucoside, from Momordica charantia fruits^[21]
• Neomogroside, from the fruit of Siraitia grosvenorii.^[22]
• Pentanorcucurbitacins A and B^{[23]: 1, 2}
• Perseapicroside A, from Persea mexicana^[4]: 44
• Scandenoside R9, from Hemsleya panacis-scandens^[4]: 45
• Spinosides A and B, from Desfontainia spinosa^{[4]: 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.^[24]: 1
• 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica foetida^[24]: 2
• 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida^[24]: 3
• 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica foetida^[24]: 4
• 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida^[24]: 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^[24]: 6
• 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida^[24]: 7
• 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica foetida^[24]: 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)^[19]: 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)^[19]: 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)^[19]: 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)^[9]: 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)^[9]: 4
• 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina^[25]
• 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)^[23]: 3

See also

• Goyaglicoside
• Karaviloside
• Momordenol, from Momordica charantia^[16]
• 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)^[19]: 4