Ursolic acid

Source: Wikipedia, the free encyclopedia.
"Malol" redirects here. For the language, see Malol language.
Ursolic acid
Names
IUPAC name
3β-Hydroxyurs-12-en-28-oic acid
Systematic IUPAC name
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Other names
Prunol, Malol, β-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966[1]
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.000.941 Edit this at Wikidata
UNII
  • InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 checkY
    Key: WCGUUGGRBIKTOS-GPOJBZKASA-N checkY
  • InChI=1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
    Key: WCGUUGGRBIKTOS-GPOJBZKABB
  • O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)[C@@H](C)[C@H](C)CC5
Properties
C30H48O3
Molar mass 456.711 g·mol−1
Melting point 285 to 288 °C (545 to 550 °F; 558 to 561 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-28-oic acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

Natural occurrence

Ursolic acid is present in many plants, such as

prunes). Apple peels contain large quantities of ursolic acid and related compounds.[3]

Potential biochemical effects

A number of potential biochemical effects of ursolic acid have been investigated, but there has been no clinical study demonstrating benefits to human health.

JURKAT leukemic T Cells leading to the reduction in proliferation and T cell activation.[7] Ursolic acid is a weak aromatase inhibitor (IC50 = 32 μM),[8] and has been shown to increase the amount of muscle and brown fat and decrease white fat obesity and associated conditions when added to diets fed to mice.[9] Under physiological concentrations, ursolic acid also induces eryptosis (the apoptosis-like suicidal cell death in defective red blood cells).[10] It has been found to reduce muscle atrophy and to stimulate muscular growth in mice,[11] also shows a potential cardioprotection.[12]

In mice, ursolic acid induces

beta-cell function in streptozotocin-induced diabetic mice fed a high-fat diet.[20] Ursolic acid increased skeletal muscle mass, as well as grip strength and exercise capacity, improved endurance, reduced the expression of the genes involved in the development of muscle atrophy, and decreased indicators of accumulated fatigue and exercise-induced stress.[21]

In rats, ursolic acid ameliorated high-fat diet-induced

hepatic steatosis and improved metabolic disorders in high-fat diet-induced non-alcoholic fatty liver disease.[22]

Uses

Ursolic acid can be found in plants that are used for cosmetics additives.[23] It can serve as a starting material for synthesis of more potent bioactive derivatives, such as experimental antitumor agents.[24]

See also

References

  1. ^ CID 64945 from PubChem
  2. ^ Constituents of Mirabilis jalapa. Siddiqui S., Siddiqui B.S., Adil Q. and Begum S., Fitoterapia, 1990, Volume 61, No. 5, page 471 (abstract)
  3. PMID 27855928
    .
  4. PMID 12907607
    .
  5. S2CID 15908477
    .
  6. ^ Wang X, Zhang F, Yang L, Mei Y, Long H, Zhang X, Zhang J, Qimuge-Suyila, Su X.,"Ursolic acid inhibits proliferation and induces apoptosis of cancer cells in vitro and in vivo", J Biomed Biotechnol. 2011;2011:419343 Full-text pdf
  7. PMID 26417220
    .
  8. PMID 18192087
    .
  9. PMID 22745735
    .
  10. PMID 21923134
    .
  11. PMID 21641545
    .
  12. PMID 21648406
    .
  13. PMID 25206561
    .
  14. PMID 32253301
    .
  15. PMID 23707761
    .
  16. S2CID 23045414
    .
  17. S2CID 20954998
    .
  18. PMID 17692828
    .
  19. S2CID 24109549
    .
  20. PMID 19013541
    .
  21. PMID 26331671
    .
  22. PMID 24489777
    .
  23. ISBN 978-1-4398-1214-3
    .
  24. PMID 15922841
    .
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