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Lupeol

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Lupeol
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 Edit this at Wikidata
  • InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21?,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1
  • CC([C@@H]1CC[C@@]2(C)[C@@]1([H])[C@@]3([H])CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]4(C)[C@]3(C)CC2)=C
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).

Lupeol is a pharmacologically active triterpenoid. It has several potential medicinal properties.

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

  1. ^ Starks, CM; Williams, RB; Norman, VL; Lawrence, JA; Goering, MG; O'Neil-Johnson, M; Hu, JF; Rice, SM; Eldridge, GR (2011). "Abronione, a rotenoid from the desert annual Abronia villosa". Phytochemistry letters. 4 (2): 72–74. doi:10.1016/j.phytol.2010.08.004. PMC 3099468. PMID 21617767.
  2. ^ Stork, Gilbert; Uyeo, Shoichiro; Wakamatsu, T.; Grieco, P.; Labovitz, J. (1971). "Total synthesis of lupeol". Journal of the American Chemical Society. 93 (19): 4945. doi:10.1021/ja00748a068.
  3. ^ Surendra, K; Corey, EJ (2009). "A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol". Journal of the American Chemical Society. 131 (39): 13928–9. doi:10.1021/ja906335u. PMID 19788328.
  4. ^ http://solcyc.solgenomics.net/LYCO/NEW-IMAGE?type=PATHWAY&object=PWY-112
  5. ^ a b Margareth B. C. Gallo; Miranda J. Sarachine (2009). "Biological activities of Lupeol" (PDF). International Journal of Biomedical and Pharmaceutical Sciences. 3 (Special Issue 1): 46–66.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ Bani S, Kaul A, Khan B, Ahmad SF, Suri KA, Gupta BD, Satti NK, Qazi GN (2006). "Suppression of T lymphocyte activity by lupeol isolated from Crataeva religious". Phytotherapy Research. 20: 279–287. doi:10.1002/ptr.1852.
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