- Cucurbitane
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Cucurbitane Identifiers CAS number 65441-59-0 (5α/β) Jmol-3D images
Image 3- 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 (verify) (what is: / ?)
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]
Contents
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
- 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
See also
- Goyaglicoside
- Karaviloside
- Momordenol, from Momordica charantia[15]
- edit] References
- ^ a b IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature (1969), The Nomenclature of Steroids — Revised Tentative Rules. European J. of Biochemistry, volume 10, 1-19
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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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Categories:- Triterpenes
- 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)
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