Cucurbitane

Cucurbitane

Identifiers
CAS number	65441-59-0 (5α/β)^Y
Jmol-3D images	Image 3
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cucurbitane is a chemical compound with formula C₃₀H₅₄ (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]

1 Derivatives
- 1.1 Natural compounds
  - 1.1.1 Named
  - 1.1.2 Unnamed
2 See also
3 References

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, C₄₀H₆₆O₉, 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,C₄₂H₆₉O₁₄, 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, C₄₈H₈₂O₁₉, 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 C₂₇H₄₀O₃, white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)^[22]^:3

References

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^ ^a ^b ^c ^d ^e ^f Cátia Ramalhete,Tayyab A. Mansoor, Silva Mulhovo, Joseph Molnár, and Maria-José U. Ferreira (2009), "Cucurbitane-Type Triterpenoids from the African Plant Momordica balsamina." Journal of Natural Products, volume 72, pages 2009–2013. doi:10.1021/np900457u
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^ J. C. Chen, R. R. Tian, M. H. Qiu, L. Lu, Y. T. Zheng, Z. Q. Zhang (2008), "Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia." Phytochemistry, volume 69, pages 1043–1048
^ Jian-Chao Chen, Lu Lu, Xian-Ming Zhang, Lin Zhou, Zhong-Rong Li, and Ming-Hua Qiu (2008), "Eight New Cucurbitane Glycosides, Kuguaglycosides A–H, from the Root of Momordica charantia L.". Helvetica Chimica Acta, volume 91, issue 5, pages 920-928. doi:10.1002/hlca.200890097
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