Cucurbitane Explained

Cucurbitane is a class of tetracyclic chemical compounds with formula (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]}

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]

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.
• Balsaminol A, from Momordica balsamina.
• Balsaminol B, from Momordica balsamina.^[4]
• Brydioside A from Bryonia dioica^[3]
• Bryoamaride and derivatives from Bryonia dioica^[3]
• 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]}
• Datiscosides, from Datisca glomerata^[3]
• Endecaphyllacins A and B, from roots of Hemsleya endecaphylla^[9]
• 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]
• 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
• Perseapicroside A, from Persea mexicana^[3]
• Scandenoside R9, from Hemsleya panacis-scandens^[3]
• Spinosides A and B, from Desfontainia spinosa^[3]

Unnamed

• 3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123−125 °C, from Momordica charantia, Momordica foetida.^[22]
• 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica foetida^[22]
• 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida^[22]
• 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica foetida^[22]
• 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida^[22]
• 5β,19-epoxy-19-methoxycucurbita-6,23-dien-3β,25-diol, soluble in chloroform, melts at 102−104 °C, from Momordica charantia, Momordica foetida^[22]
• 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida^[22]
• 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica foetida^[22]
• ,, white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 kg)^[18]
• 23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside,, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)^[18]
• 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O--25-O-β-glucopyranoside,, white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)^[18]
• 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]
• 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]
• 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina^[23]
• 25,26,27-trinorcucurbit-5-ene-3,7,23-trione, white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)^[24]

See also

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

Notes and References

1. 1969 . The Nomenclature of Steroids — Revised Tentative Rules . 10.1111/j.1432-1033.1969.tb00650.x . European Journal of Biochemistry . 10 . 1–19 . free .
2. Satish Kumar and Raj Kumar (1991), Dictionary of Biochemistry. Anmol Publications, India
3. Chen . J. C. . Chiu . M. H. . Nie . R. L. . Cordell . G. A. . Qiu . S. X. . Cucurbitacins and cucurbitane glycosides: Structures and biological activities . 10.1039/B418841C . Natural Product Reports . 22 . 3 . 386–399 . 2005 . 16010347.
4. Ramalhete . C. T. . Mansoor . T. A. . Mulhovo . S. . Molnár . J. . Ferreira . M. J. U. . Cucurbitane-Type Triterpenoids from the African PlantMomordica balsamina . 10.1021/np900457u . Journal of Natural Products . 72 . 11 . 2009–2013 . 2009 . 19795842. 10884/1322 . free .
5. 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 .
6. Olaniyi . A. A. . A neutral constituent of Momordica foetida . Lloydia . 38 . 4 . 361–362 . 1975 . 1186439.
7. Akihisa . T. . Higo . N. . Tokuda . H. . Ukiya . M. . Akazawa . H. . Tochigi . Y. . Kimura . Y. . Suzuki . T. . Nishino . H. . 10.1021/np068075p . Cucurbitane-Type Triterpenoids from the Fruits of Momordica charantia and Their Cancer Chemopreventive Effects. Journal of Natural Products . 70 . 8 . 1233–1239 . 2007 . 17685651.
8. Wang . Da-Cheng . Pan . Hong-Yu . Deng . Xu-Ming . Xiang . Hua . Gao . Hui-Yuan . Cai . Hui . Wu . Li-Jun . 2007 . Cucurbitane and hexanorcucurbitane glycosides from the fruits of Cucurbita pepo cv dayangua . Journal of Asian Natural Products Research . 9 . 6. 525–529 . 10.1080/10286020600782538 . 17885839 . 27762659 .
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10. 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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