Lupeol

Lupeol
Other names

(3β,13ξ)-Lup-20(29)-en-3-ol; Clerodol; Monogynol B; Fagarasterol; Farganasterol
Identifiers
CAS number 545-47-1 Y
PubChem 259846
ChemSpider 23089061
ChEMBL CHEMBL289191
Jmol-3D images Image 1
Properties
Molecular formula C30H50O
Molar mass 426.72 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lupeol is a pharmacologically active triterpenoid found in a variety of plants, including mango and acacia visco. It has several medicinal properties, one being anti-inflammatory. A 1998 study found lupeol to decrease paw swelling in rats by 39%, compared to 35% for the standardized control compound indomethacin.[1]

Contents

Pharmacology

Lupeol has a complex pharmacology in humans, displaying antiprotozoal, antimicrobial, antiinflammatory, antitumor and chemopreventive properties.[2] One study has also found some activity as a Dipeptidyl peptidase-4 inhibitor and prolyl oligopeptidase inhibitor at high concentrations (in the millimolar range).[3]

It is an effective inhibitor in laboratory models of prostate and skin cancers.[4][5][6]

Mechanism of action

As an anti-inflammatory agent, lupeol functions primarily on the interleukin system. Bani et al. (2006) found lupeol to decrease IL-4 (interleukin 4) production by T-helper type 2 cells.[2]

References

  1. ^ Geetha, T; Varalakshmi, P (2001). "Anti-inflammatory activity of lupeol and lupeol linoleate in rats". Journal of ethnopharmacology 76 (1): 77–80. doi:10.1016/S0378-8741(01)00175-1. PMID 11378285. 
  2. ^ a b Margareth B. C. Gallo, Miranda J. Sarachine (2009). "Biological activities of Lupeol". International Journal of Biomedical and Pharmaceutical Sciences. http://www.globalsciencebooks.info/JournalsSup/images/0906/IJBPS_3%28SI1%2946-66o.pdf. 
  3. ^ Marques, MR; Stüker, C; Kichik, N; Tarragó, T; Giralt, E; Morel, AF; Dalcol, II (2010). "Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers.". Fitoterapia 81 (6): 552–6. doi:10.1016/j.fitote.2010.01.018. PMID 20117183. 
  4. ^ Prasad S, Kalra N, Singh M, Shukla Y (2008). "Protective effects of lupeol and mango extract against androgen induced oxidative stress in Swiss albino mice" (PDF). Asian J Androl 10 (2): 313–8. doi:10.1111/j.1745-7262.2008.00313.x. PMID 18097535. http://www.nature.com/aja/journal/v10/n2/pdf/aja2008241a.pdf. 
  5. ^ Nigam N, Prasad S, Shukla Y (2007). "Preventive effects of lupeol on DMBA induced DNA alkylation damage in mouse skin". Food Chem Toxicol 45 (11): 2331–5. doi:10.1016/j.fct.2007.06.002. PMID 17637493. 
  6. ^ Saleem M, Afaq F, Adhami VM, Mukhtar H (2004). "Lupeol modulates NF-kappaB and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice". Oncogene 23 (30): 5203–14. doi:10.1038/sj.onc.1207641. PMID 15122342. 

Further reading