Cucurbitane is a class of tetracyclic chemical compounds with formula C
30H
54 (CAS number 65441-59-0). 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]
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| Names | |
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| IUPAC name
19-Nor-5ξ,9β,10α-lanostane
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| 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 | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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).
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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
editNatural compounds
editCompounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals.[3] Natural cucurbitane-related compounds include:
Named
edit- 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
edit- 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
edit- 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
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- ^ Satish Kumar and Raj Kumar (1991), Dictionary of Biochemistry. Anmol Publications, India
- ^ a b c d e f g h i Chen, J. C.; Chiu, M. H.; Nie, R. L.; Cordell, G. A.; Qiu, S. X. (2005). "Cucurbitacins and cucurbitane glycosides: Structures and biological activities". Natural Product Reports. 22 (3): 386–399. doi:10.1039/B418841C. PMID 16010347.
- ^ a b c d e f Ramalhete, C. T.; Mansoor, T. A.; Mulhovo, S.; Molnár, J.; Ferreira, M. J. U. (2009). "Cucurbitane-Type Triterpenoids from the African PlantMomordica balsamina". Journal of Natural Products. 72 (11): 2009–2013. doi:10.1021/np900457u. hdl:10884/1322. PMID 19795842.
- ^ Lolitkar, M. M.; Rao, M. R. Rajarama (1962). "Note on a Hypoglycaemic Principle Isolated from the fruits of Momordica charantia". Journal of the University of Bombay. 29: 223–224.
- ^ Olaniyi, A. A. (1975). "A neutral constituent of Momordica foetida". Lloydia. 38 (4): 361–362. PMID 1186439.
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- ^ Jian-Wen Tan, Ze-Jun Dong, Zhi-Hui Ding and Ji-Kai Liu (2002), "Lepidolide, a Novel Seco-ring-A Cucurbitane Triterpenoid from Russula lepida (Basidiomycetes)". Zeitschrift für Naturforschung Series C, volume 57C issue 11/12, pages 963-965.
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- ^ Chen, J. C.; Tian, R. R.; Qiu, M. H.; Lu, L.; Zheng, Y. T.; Zhang, Z. Q. (2008). "Trinorcucurbitane and cucurbitane triterpenoids from the roots of Momordica charantia". Phytochemistry. 69 (4): 1043–1048. doi:10.1016/j.phytochem.2007.10.020. PMID 18045630.
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