lupeol
{{Chembox
| ImageFile = Lupeol structure.svg
| ImageSize = 200px
| IUPACName = (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
| OtherNames = (3β,13ξ)-Lup-20(29)-en-3-ol; Clerodol; Monogynol B; Fagarasterol; Farganasterol
|Section1={{Chembox Identifiers
| CASNo = 545-47-1
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O268W13H3O
| PubChem = 259846
| ChEMBL = 289191
| ChemSpiderID = 23089061
| SMILES = 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
| InChI = 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
}}
|Section2={{Chembox Properties
| C=30 | H=50 | O=1
| Appearance =
| Density =
| MeltingPt =
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|Section3={{Chembox Hazards
| MainHazards =
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Lupeol is a pharmacologically active pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.{{Cite journal|last1=Majumder|first1=Soumya|last2=Ghosh|first2=Arindam|last3=Bhattacharya|first3=Malay|date=2020-08-27|title=Natural anti-inflammatory terpenoids in Camellia japonica leaf and probable biosynthesis pathways of the metabolome|journal=Bulletin of the National Research Centre|volume=44|issue=1|pages=141|doi=10.1186/s42269-020-00397-7|issn=2522-8307|doi-access=free}}
Natural occurrences
Lupeol is found in a variety of plants, including mango, Acacia visco and Abronia villosa.{{cite journal | vauthors = Starks CM, Williams RB, Norman VL, Lawrence JA, Goering MG, O'Neil-Johnson M, Hu JF, Rice SM, Eldridge GR | title = Abronione, a rotenoid from the desert annual Abronia villosa | journal = Phytochemistry Letters | volume = 4 | issue = 2 | pages = 72–74 | date = June 2011 | pmid = 21617767 | pmc = 3099468 | doi = 10.1016/j.phytol.2010.08.004 }} It is also found in dandelion coffee. Lupeol is present as a major component in Camellia japonica leaf.
Total synthesis
The first total synthesis of lupeol was reported by Gilbert Stork et al.{{Cite journal | vauthors = Stork G, Uyeo S, Wakamatsu T, Grieco P, Labovitz J |title=Total synthesis of lupeol|year=1971 |journal=Journal of the American Chemical Society|volume=93|issue=19|page=4945 |doi=10.1021/ja00748a068 }}
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.{{cite journal | vauthors = Surendra K, Corey EJ | title = A short enantioselective total synthesis of the fundamental pentacyclic triterpene lupeol | journal = Journal of the American Chemical Society | volume = 131 | issue = 39 | pages = 13928–9 | date = October 2009 | pmid = 19788328 | doi = 10.1021/ja906335u }}
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.{{cite web | url=http://solcyc.solgenomics.net/LYCO/NEW-IMAGE?type=PATHWAY&object=PWY-112 | archive-url=https://archive.today/20120717220059/http://solcyc.solgenomics.net/LYCO/NEW-IMAGE?type=PATHWAY&object=PWY-112 | url-status=dead | archive-date=2012-07-17 | title=Solanum lycopersicum lupeol biosynthesis }} 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.
Pharmacology
Lupeol has a complex pharmacology, displaying antiprotozoal, antimicrobial, antiinflammatory, antitumor and chemopreventive properties.{{cite journal | journal = International Journal of Biomedical and Pharmaceutical Sciences | title = Biological activities of Lupeol | author1 = Margareth B. C. Gallo | author2 = Miranda J. Sarachine | url = http://www.globalsciencebooks.info/JournalsSup/images/0906/IJBPS_3%28SI1%2946-66o.pdf | volume = 3 | issue = Special Issue 1 | pages = 46–66 | date = 2009 | url-status = dead | archive-url = https://web.archive.org/web/20101025091350/http://www.globalsciencebooks.info/JournalsSup/images/0906/IJBPS_3(SI1)46-66o.pdf | archive-date = 2010-10-25 }}
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.{{cite journal | vauthors = Geetha T, Varalakshmi P | title = Anti-inflammatory activity of lupeol and lupeol linoleate in rats | journal = Journal of Ethnopharmacology | volume = 76 | issue = 1 | pages = 77–80 | date = June 2001 | pmid = 11378285 | doi = 10.1016/S0378-8741(01)00175-1 }}
One study has also found some activity as a dipeptidyl peptidase-4 inhibitor and prolyl oligopeptidase inhibitor at high concentrations (in the millimolar range).{{cite journal | vauthors = Marques MR, Stüker C, Kichik N, Tarragó T, Giralt E, Morel AF, Dalcol II | title = Flavonoids with prolyl oligopeptidase inhibitory activity isolated from Scutellaria racemosa Pers | journal = Fitoterapia | volume = 81 | issue = 6 | pages = 552–6 | date = September 2010 | pmid = 20117183 | doi = 10.1016/j.fitote.2010.01.018 | doi-access = free }}
It is an effective inhibitor in laboratory models of prostate and skin cancers.{{cite journal | vauthors = Prasad S, Kalra N, Singh M, Shukla Y | title = Protective effects of lupeol and mango extract against androgen induced oxidative stress in Swiss albino mice | journal = Asian Journal of Andrology | volume = 10 | issue = 2 | pages = 313–8 | date = March 2008 | pmid = 18097535 | doi = 10.1111/j.1745-7262.2008.00313.x | doi-access = free }}{{cite journal | vauthors = Nigam N, Prasad S, Shukla Y | title = Preventive effects of lupeol on DMBA induced DNA alkylation damage in mouse skin | journal = Food and Chemical Toxicology | volume = 45 | issue = 11 | pages = 2331–5 | date = November 2007 | pmid = 17637493 | doi = 10.1016/j.fct.2007.06.002 }}{{cite journal | vauthors = Saleem M, Afaq F, Adhami VM, Mukhtar H | title = Lupeol modulates NF-kappaB and PI3K/Akt pathways and inhibits skin cancer in CD-1 mice | journal = Oncogene | volume = 23 | issue = 30 | pages = 5203–14 | date = July 2004 | pmid = 15122342 | doi = 10.1038/sj.onc.1207641 | doi-access = }}
As an anti-inflammatory agent, lupeol functions primarily on the interleukin system. Lupeol to decreases interleukin 4 (IL-4) production by T-helper type 2 cells.{{cite journal | vauthors = Bani S, Kaul A, Khan B, Ahmad SF, Suri KA, Gupta BD, Satti NK, Qazi GN | title = Suppression of T lymphocyte activity by lupeol isolated from Crataeva religiosa | journal = Phytotherapy Research | volume = 20 | issue = 4 | pages = 279–87 | date = April 2006 | pmid = 16557610 | doi = 10.1002/ptr.1852 | s2cid = 34485412 }}
Lupeol has been found to have a contraceptive effect due to its inhibiting effect on the calcium channel of sperm (CatSper).{{cite journal | vauthors = Mannowetz N, Miller MR, Lishko PV | title = Regulation of the sperm calcium channel CatSper by endogenous steroids and plant triterpenoids | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 114 | issue = 22 | pages = 5743–5748 | date = May 2017 | pmid = 28507119 | pmc = 5465908 | doi = 10.1073/pnas.1700367114 | doi-access = free }}
Lupeol has also been shown to exert anti-angiogenic and anti-cancer effects via the downregulation of TNF-alpha and VEGFR-2.{{cite journal | vauthors = Kangsamaksin T, Chaithongyot S, Wootthichairangsan C, Hanchaina R, Tangshewinsirikul C, Svasti J | title = Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor-α | journal = PLOS ONE | volume = 12 | issue = 12 | pages = e0189628 | date = 2017-12-12 | pmid = 29232409 | pmc = 5726636 | doi = 10.1371/journal.pone.0189628 | bibcode = 2017PLoSO..1289628K | veditors = Ahmad A | doi-access = free }}
The leaves of Camellia japonica contain lupeol.