Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.[1]
 | |
| Names | |
|---|---|
| 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 | |
| Other names (3β,13ξ)-Lup-20(29)-en-3-ol; Clerodol; Monogynol B; Fagarasterol; Farganasterol | |
| Identifiers | |
3D model (JSmol) | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.082 |
PubChem CID | |
| UNII | |
| |
| |
| Properties | |
| C30H50O | |
| Molar mass | 426.729 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Natural occurrences
Lupeol is found in a variety of plants, including mango, Acacia visco and Abronia villosa.[2] It is also found in dandelion coffee. Lupeol is present as a major component in Camellia japonica leaf.[1]
Total synthesis
The first total synthesis of lupeol was reported by Gilbert Stork et al.[3]
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.[4]
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.[5] A recent study on the metabolomics of Camellia japonica leaf revealed that lupeol is produced from squalene epoxide where squalene play the role as a precursor.[1]
Pharmacology
Lupeol has a complex pharmacology, displaying antiprotozoal, antimicrobial, antiinflammatory, antitumor and chemopreventive properties.[6]
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.[7]
One study has also found some activity as a Dipeptidyl peptidase-4 inhibitor and prolyl oligopeptidase inhibitor at high concentrations (in the millimolar range).[8]
It is an effective inhibitor in laboratory models of prostate and skin cancers.[9][10][11]
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.[6][12]
Lupeol has been found to have a contraceptive effect due to its inhibiting effect on the calcium channel of sperm (CatSper).[13]
Lupeol has also been shown to exert anti-angiogenic and anti-cancer effects via the downregulation of TNF-alpha and VEGFR-2.[14]
Famous anti-inflammatory ethno-medicinal plant Camellia japonica contains anti-inflammatory component lupeol in its leaf.[1]