Maslinic acid

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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 Edit this at Wikidata
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 ?)

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.

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] Additionally, maslinic acid serves as a glycogen phosphorylase inhibitor in mouse liver,[4][5] as evidenced by increased glycogen accumulation in rainbow trout liver.[6]

Clinical significance

Maslinic acid demonstrates antioxidant capabilities against oxygen and nitrogen reactive species.[7][8] It also exhibits a suppressive impact on proinflammatory cytokines like TNF-α and IL-6 in murine macrophages.[8] These mechanisms could contribute to enhanced protein synthesis, growth rates, and joint support.[9] Maslinic acid has been shown to improve muscle mass in the elderly when combined with resistance exercise.[10]

References

  1. ^ University of Granada (11 July 2007). "Compound From Olive-pomace Oil Inhibits HIV Spread". sciencedaily.com. Retrieved 2009-06-16.
  2. ^ Juan ME, Planas JM, Ruiz-Gutierrez V, Daniel H, Wenzel U (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, Guan T, Qian Y, Tang X, Huang M, Huang L, Li Y, Sun M (November 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. ^ Márquez Martín A, De La Puerta Vázquez R, Fernández-Arche A, Ruiz-Gutiérrez V (2006). "Supressive effect of maslinic acid from pomace olive oil on oxidative stress and cytokine production in stimulated murine macrophages". Free Radical Research. 40 (3): 295–302. doi:10.1080/10715760500467935. ISSN 1071-5762. PMID 16484046.
  5. ^ Wen X, Sun H, Liu J, Wu G, Zhang L, Wu X, Ni P (2005-11-15). "Pentacyclic triterpenes. Part 1: The first examples of naturally occurring pentacyclic triterpenes as a new class of inhibitors of glycogen phosphorylases". Bioorganic & Medicinal Chemistry Letters. 15 (22): 4944–4948. doi:10.1016/j.bmcl.2005.08.026. ISSN 0960-894X. PMID 16169219.
  6. ^ Vlietinck A, De Bruyne T, Apers S, Pieters L (1998). "Plant-Derived Leading Compounds for Chemotherapy of Human Immunodeficiency Virus (HIV) Infection" (PDF). Planta Medica. 64 (02): 97–109. doi:10.1055/s-2006-957384. ISSN 0032-0943. PMID 9525100.
  7. ^ Conlon, Ian; Raff, Martin (1999-01-22). "Size Control in Animal Development". Cell. 96 (2): 235–244. doi:10.1016/S0092-8674(00)80563-2. PMID 9988218.
  8. ^ a b Montilla MP, Agil A, Navarro MC, Jiménez MI, García-Granados A, Parra A, Cabo MM (2003). "Antioxidant Activity of Maslinic Acid, a Triterpene Derivative Obtained from Olea europaea". Planta Medica. 69 (5): 472–474. doi:10.1055/s-2003-39698. ISSN 0032-0943. PMID 12802735.
  9. ^ Nierding, Axel. "Acide Maslinique: Propriétés Et Bienfaits" [Maslinic Acid: Properties And Benefits]. Polyvalents (in French). Retrieved 2023-12-25.
  10. ^ Nagai N, Yagyu S, Sakane N (2019). "Maslinic acid derived from olive fruit in combination with resistance training improves muscle mass and mobility functions in the elderly". Journal of Clinical Biochemistry and Nutrition. 64 (3): 224–230. doi:10.3164/jcbn.18-104. PMC 6529705. PMID 31138956.
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