Lupane (compound)
 | |
| Names | |
|---|---|
| IUPAC name
(1S,3aR,5aR,5bR,7aS,11aS,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-Hexamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene
| |
| Identifiers | |
3D model (JSmol)
|
|
| 2562721 | |
| ChEBI | |
| ChemSpider | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C30H52 | |
| Molar mass | 412.746 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Lupane is a pentacyclic triterpene hydrocarbon with the molecular formula C₃₀H₅₂. It serves as the core skeleton for various bioactive compounds, including lupeol and betulinic acid, which are prevalent in numerous plant species.[1] It actually features a structure composed of five fused rings––four cyclohexane rings and one cyclopentane––and is one of the major triterpene skeletons alongside hopane, oleanane, and ursane types. The compound is common in birch bark.
Occurrence and derivatives
[edit]Derivatives of lupane, such as lupeol, betulin, and betulinic acid, are found in high concentrations in birch bark (Betula spp.), mango peels, olives, strawberries, and other fruits.[2]
Similar derivatives
[edit]Similar derivatives are the following ones:
- Lupeol (C₃₀H₅₀O) – a hydroxylated lupane at position C‑3, with noted anti-inflammatory and anti‑cancer effects.
- Betulin (C₃₀H₅₀O₂) – a diol lupane naturally abundant in birch bark (up to 30% by dry weight) and researched for wound healing and pharmaceutical uses.[3]
- Betulinic acid – the oxidized carboxylic acid form of betulin; one of the most extensively studied lupane-derived compounds with anticancer activity.[4]
Biosynthesis and uses
[edit]Like all triterpenes, lupane is biosynthesized via cyclization of the squalene precursor in plants and fungi.
While lupane itself has limited direct applications, its derivatives have been used in topical wound-healing formulations and are under evaluation as nutraceuticals and anticancer agents. Betulin-rich extracts are utilized in dermatology.
Biological activity
[edit]Pentacyclic lupane derivatives have attracted attention for potential pharmacological effects—including anti-inflammatory, antiviral, hepatoprotective, and anticancer activities—with generally low toxicity.[5][6] Lupane-type molecules have been shown to modulate apoptosis and cell signaling in various cancer cell lines.
Recent studies highlight:
- Antiproliferative and anti-inflammatory effects of 3,4‑seco‑lupane derivatives from Eleutherococcus sessiliflorus.[7]
- Lupane-triterpene-tryptamine hybrids demonstrating potent anti‑bladder cancer activity through modulation of DUSP5 and the p38 MAPK pathway.
- Lupane-based analogs with inhibitory activity toward influenza A (H1N1).
See also
[edit]References
[edit]- ^ Jäger, Sebastian; Trojan, Holger; Kopp, Thomas; Laszczyk, Melanie N.; Scheffler, Armin (2009-06-04). "Pentacyclic Triterpene Distribution in Various Plants – Rich Sources for a New Group of Multi-Potent Plant Extracts". Molecules. 14 (6). MDPI AG: 2016–2031. doi:10.3390/molecules14062016. ISSN 1420-3049. PMC 6254168. PMID 19513002.
- ^ Jäger, Sebastian; Trojan, Holger; Kopp, Thomas; Laszczyk, Melanie N.; Scheffler, Armin (2009-06-04). "Pentacyclic Triterpene Distribution in Various Plants – Rich Sources for a New Group of Multi-Potent Plant Extracts". Molecules. 14 (6). MDPI AG: 2016–2031. doi:10.3390/molecules14062016. ISSN 1420-3049. PMC 6254168. PMID 19513002.
- ^ Zhao, Nan; Guan, Ju; Forouhar, Farhad; Tschaplinski, Timothy J.; Cheng, Zong-Ming; Tong, Liang; Chen, Feng (2009). "Two poplar methyl salicylate esterases display comparable biochemical properties but divergent expression patterns". Phytochemistry. 70 (1). Elsevier BV: 32–39. Bibcode:2009PChem..70...32Z. doi:10.1016/j.phytochem.2008.11.014. ISSN 0031-9422. PMID 19136124.
- ^ Fulda, Simone (2008-06-27). "Betulinic Acid for Cancer Treatment and Prevention". International Journal of Molecular Sciences. 9 (6). MDPI AG: 1096–1107. doi:10.3390/ijms9061096. ISSN 1422-0067. PMC 2658785. PMID 19325847.
- ^ Cite error: The named reference
LupeolAntiCancer2016was invoked but never defined (see the help page). - ^ Cite error: The named reference
BetulinicReview2022was invoked but never defined (see the help page). - ^ Wang, Chao; Wang, Han; Zheng, Cangxin; Liu, Zhenming; Gao, Xiaozuo; Xu, Fengrong; Niu, Yan; Zhang, Liangren; Xu, Ping (2021). "Research progress of MEK1/2 inhibitors and degraders in the treatment of cancer". European Journal of Medicinal Chemistry. 218. Elsevier BV: 113386. doi:10.1016/j.ejmech.2021.113386. ISSN 0223-5234. PMID 33774345.