Lupeol
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| Names | |
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| IUPAC name
(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
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| Other names
(3β,13ξ)-Lup-20(29)-en-3-ol; Clerodol; Monogynol B; Fagarasterol; Farganasterol
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| Identifiers | |
545-47-1  |
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| ChEMBL | ChEMBL289191 |
| ChemSpider | 23089061 |
| Jmol 3D model | Interactive image |
| PubChem | 259846 |
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| Properties | |
| C30H50O | |
| Molar mass | 426.73 g·mol−1 |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Lupeol is a pharmacologically active triterpenoid. It has several potential medicinal properties.
Contents
Natural occurrences
Lupeol is found in a variety of plants, including mango, Acacia visco and Abronia villosa.[1] It is also found in dandelion coffee.
Total synthesis
The first total synthesis of lupeol was reported by Gilbert Stork et al.[2]
In 2009, Surendra and Corey reported a more efficient and enantioselective total synthesis of lupeol, starting from (1E,5E)-8-[(2S)-3,3-dimethyloxiran-2-yl]-2,6-dimethylocta-1,5-dienyl acetate by use of a polycyclization.[3]
Biosynthesis
Lupeol is produced by several organisms from squalene epoxide. Dammarane and baccharane skeletons are formed as intermediates. The reactions are catalyzed by the enzyme lupeol synthase.[4]
Pharmacology
Lupeol has a complex pharmacology, displaying antiprotozoal, antimicrobial, antiinflammatory, antitumor and chemopreventive properties.[5]
Animal models suggest lupeol may act as an anti-inflammatory agent. A 1998 study found lupeol to decrease paw swelling in rats by 39%, compared to 35% for the standardized control compound indomethacin.[6]
One study has also found some activity as a Dipeptidyl peptidase-4 inhibitor and prolyl oligopeptidase inhibitor at high concentrations (in the millimolar range).[7]
It is an effective inhibitor in laboratory models of prostate and skin cancers.[8][9][10]
As an anti-inflammatory agent, lupeol functions primarily on the interleukin system. Lupeol to decreases IL-4 (interleukin 4) production by T-helper type 2 cells.[5][11]
See also
References
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- ↑ http://solcyc.solgenomics.net/LYCO/NEW-IMAGE?type=PATHWAY&object=PWY-112
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