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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
UNII
  • 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 pentacyclic triterpenoid. It has several potential medicinal properties, like anticancer and anti-inflammatory activity.[1]

Natural occurrences

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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

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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

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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

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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 interleukin 4 (IL-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]

The leaves of Camellia japonica contain lupeol.[1]

See also

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References

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  1. ^ a b c d Majumder, Soumya; Ghosh, Arindam; Bhattacharya, Malay (2020-08-27). "Natural anti-inflammatory terpenoids in Camellia japonica leaf and probable biosynthesis pathways of the metabolome". Bulletin of the National Research Centre. 44 (1): 141. doi:10.1186/s42269-020-00397-7. ISSN 2522-8307.
  2. ^ Starks CM, Williams RB, Norman VL, Lawrence JA, Goering MG, O'Neil-Johnson M, Hu JF, Rice SM, Eldridge GR (June 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.
  3. ^ Stork G, Uyeo S, Wakamatsu T, Grieco P, Labovitz J (1971). "Total synthesis of lupeol". Journal of the American Chemical Society. 93 (19): 4945. doi:10.1021/ja00748a068.
  4. ^ Surendra K, Corey EJ (October 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.
  5. ^ "Solanum lycopersicum lupeol biosynthesis". Archived from the original on 2012-07-17.
  6. ^ 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. Archived from the original (PDF) on 2010-10-25.
  7. ^ Geetha T, Varalakshmi P (June 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.
  8. ^ Marques MR, Stüker C, Kichik N, Tarragó T, Giralt E, Morel AF, Dalcol II (September 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.
  9. ^ Prasad S, Kalra N, Singh M, Shukla Y (March 2008). "Protective effects of lupeol and mango extract against androgen induced oxidative stress in Swiss albino mice". Asian Journal of Andrology. 10 (2): 313–8. doi:10.1111/j.1745-7262.2008.00313.x. PMID 18097535.
  10. ^ Nigam N, Prasad S, Shukla Y (November 2007). "Preventive effects of lupeol on DMBA induced DNA alkylation damage in mouse skin". Food and Chemical Toxicology. 45 (11): 2331–5. doi:10.1016/j.fct.2007.06.002. PMID 17637493.
  11. ^ Saleem M, Afaq F, Adhami VM, Mukhtar H (July 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.
  12. ^ Bani S, Kaul A, Khan B, Ahmad SF, Suri KA, Gupta BD, Satti NK, Qazi GN (April 2006). "Suppression of T lymphocyte activity by lupeol isolated from Crataeva religiosa". Phytotherapy Research. 20 (4): 279–87. doi:10.1002/ptr.1852. PMID 16557610. S2CID 34485412.
  13. ^ Mannowetz N, Miller MR, Lishko PV (May 2017). "Regulation of the sperm calcium channel CatSper by endogenous steroids and plant triterpenoids". Proceedings of the National Academy of Sciences of the United States of America. 114 (22): 5743–5748. doi:10.1073/pnas.1700367114. PMC 5465908. PMID 28507119.
  14. ^ Kangsamaksin T, Chaithongyot S, Wootthichairangsan C, Hanchaina R, Tangshewinsirikul C, Svasti J (2017-12-12). Ahmad A (ed.). "Lupeol and stigmasterol suppress tumor angiogenesis and inhibit cholangiocarcinoma growth in mice via downregulation of tumor necrosis factor-α". PLOS ONE. 12 (12): e0189628. Bibcode:2017PLoSO..1289628K. doi:10.1371/journal.pone.0189628. PMC 5726636. PMID 29232409.
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