Cucurbitane is a tetracyclic chemical compound with formula . 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.Satish Kumar and Raj Kumar (1991), Dictionary of Biochemistry. Anmol Publications, India
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).
Cucurbitane is the core chemical structure of a class of derivatives known as cucurbitane-type triterpenoids or simply as cucurbitanes.
Derivatives
Natural compounds Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals. Natural cucurbitane-related compounds include:
Named Balsaminapentaol, from Momordica balsamina. Balsaminol A, from Momordica balsamina. Balsaminol B, from Momordica balsamina. Brydioside A from Bryonia dioica Bryoamaride and derivatives from Bryonia dioica Charantin or foetidin, from Momordica charantia and Momordica foetida Charantosides I-VIII, from Momordica charantia. Cucurbalsaminol B, from Momordica balsamina. Cucurbalsaminol A, from Momordica balsamina. Cucurbitacins A-L, O-T Datiscosides, from Datisca glomerata Endecaphyllacins A and B, from roots of Hemsleya endecaphylla Hemslecins A and B, from roots of H. endecaphylla Lepidolide, from the mushroom Russula lepidaJian-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. Karavilagenin E, from Momordica balsamina. Khekadaengosides A, B, D and K, from Trichosanthes tricuspidata Kuguacins A-S, from stems and leaves of Momordica charantia Kuguaglycosides A-H, from the root of Momordica charantia Mogrosides I-V, from the fruits of Siraitia grosvenorii Momordicin I, II and 28, from Momordica charantia Momordicines II and IV, from leaves of Momordica charantiaDaniel Bisrat Mekuria, Takehiro Kashiwagi, Shin-ichi Tebayashi, and Chul-Sa Kim (2006)"Cucurbitane Glucosides from Momordica charantia Leaves as Oviposition Deterrents to the Leafminer, Liriomyza trifolii". Z. Naturforsch., volume 61c, pages 81–86 Momordicosides A-S, from Momordica charantia fruits Neokuguaglucoside, from Momordica charantia fruits Neomogroside, from the fruit of Siraitia grosvenorii.Si Jian-yong, Chen Di-hua, Chang Qi and Shen Lian-gang (1996), Isolation and Determination of Cucurbitane-Glycosides from Fresh Fruits of Siraitia Grosvenorii. Journal of Integrative Plant Biology, volume 38, issue 6, pages, 489–494 Pentanorcucurbitacins A and B Perseapicroside A, from Persea mexicana Scandenoside R9, from Hemsleya panacis-scandens Spinosides A and B, from Desfontainia spinosa
Unnamed 3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123−125 °C, from Momordica charantia, Momordica foetida. 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica foetida 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica foetida 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida 5β,19-epoxy-19-methoxycucurbita-6,23-dien-3β,25-diol, soluble in chloroform, melts at 102−104 °C, from Momordica charantia, Momordica foetida 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica foetida , , white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 kg) 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) 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside, , white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg) 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) 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) 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina 25,26,27-trinorcucurbit-5-ene-3,7,23-trione , white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)
See also Goyaglicoside Karaviloside Momordenol, from Momordica charantia 24(R)-stigmastan-3β,5α,6β-triol-25-ene 3-O-β-glucopyranoside, , white powder, from Momordica charantia fruit (15 mg/35 kg)
References