Lupeol

Last updated
Lupeol
Lupeol structure.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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]

Contents

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]

LUPEOL SYNTHESIS.png

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 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

Related Research Articles

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<span class="mw-page-title-main">Oleanolic acid</span> Pentacyclic chemical compound in plant leaves and fruit

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<span class="mw-page-title-main">Oligopeptidase</span> Enzymes that cleaves peptides but not proteins

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<span class="mw-page-title-main">Quinone methide</span> Chemical compound

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<span class="mw-page-title-main">Epoxide hydrolase 2</span> Protein-coding gene in the species Homo sapiens

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<span class="mw-page-title-main">Amyrin</span> Chemical compound

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References

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  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.
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  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.
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  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.
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