Maslinic acid

Maslinic acid is a compound derived from dry olive-pomace oil (an olive skin wax) which is a byproduct of olive oil extraction. It is a member of the group of triterpenes known as oleananes.

Maslinic acid
Names
IUPAC name
2α,3β-Dihydroxyolean-12-en-28-oic acid
Systematic IUPAC name
(4aS,6aS,6bR,8aR,10R,11R,12aR,12bR,14bS)-10,11-Dihydroxy-2,2,6a,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
Crategolic acid; Masilinic acid; Crataegolic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.128.873
KEGG
UNII
  • InChI=1S/C30H48O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21-,22+,23-,27-,28+,29+,30-/m0/s1 ☒N
    Key: MDZKJHQSJHYOHJ-LLICELPBSA-N ☒N
  • CC1(C)[C@@H](O)[C@H](O)C[C@@]2(C)[C@]([H])1CC[C@]3(C)[C@@]([H])2CC=C4[C@](C)3CC[C@]5([C@](O)=O)[C@]([H])4CC(C)(C)CC5
Properties
C30H48O4
Molar mass 472.710 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Pharmacology

In vitro study shows that maslinic acid inhibits serine proteases, key enzymes necessary for the spread of HIV within an individual's body.[1] It also has in vitro antiproliferative effects on colon cancer cells.[2] Maslinic acid increases EAAT2 (GLT-1) glutamate reuptake and may reduce glutamatergic toxicity in rats.[3]


Maslinic acid demonstrates antioxidant capabilities against oxygen and nitrogen reactive species.[4][5] It also exhibits a suppressive impact on proinflammatory cytokines like TNF-α and IL-6 in murine macrophages.[6] A recent review shows how these mechanisms could contribute to enhanced protein synthesis, growth rates, and joint support.[7] Additionally, maslinic acid serves as a glycogen phosphorylase inhibitor in mouse liver,[8][9] as evidenced by increased glycogen accumulation in rainbow trout liver.[10]

References
  1. "Compound From Olive-pomace Oil Inhibits HIV Spread". sciencedaily.com. Retrieved 2009-06-16.
  2. Juan ME, et al. (2008). "Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells" (PDF). Br J Nutr. 100 (1): 36–43. doi:10.1017/S0007114508882979. PMID 18298868.
  3. Guan T, Qian Y, et al. (2011). "Maslinic acid, a natural inhibitor of glycogen phosphorylase, reduces cerebral ischemic injury in hyperglycemic rats by GLT-1 up-regulation". J. Neurosci. Res. 89 (11): 1829–39. doi:10.1002/jnr.22671. PMID 21800347.
  4. Conlon I, Raff M. Size control in animal development. Cell 1999;96:235–44.
  5. Montilla MP, Agil A, Navarro MC, Jimenez MI, Garcia-Granados A, Parra A, Cabo MM. Antioxidant activity of maslinic acid, a triterpene derivative obtained from Olea europaea. Planta Med 2003;69:472–4.
  6. Montilla MP, Agil A, Navarro MC, Jimenez MI, Garcia-Granados A, Parra A, Cabo MM. Antioxidant activity of maslinic acid, a triterpene derivative obtained from Olea europaea. Planta Med 2003;69:472–4.
  7. https://polyvalents.fr/acide-maslinique/
  8. Márquez-Martín A, De la Puerta-Vázquez R, Fernández-Arche A, Ruíz-Gutiérrez V. Suppressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages. Free Rad Res 2006;40:205–302.
  9. Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P. Pentacyclic triterpenes. Part 1: the first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases. Bioorg Med Chem Lett 2005;15(22):4944–8.
  10. Vlietinck AJ, De Bruyne T, Apers S, Pieters LA. Plant-derived leading compounds for chemotherapy of human immunodeficiency virus (HIV) infection. Planta Med 1998;64:97–109.
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