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).
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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

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. PMID 18298868
    .
  3. PMID 21800347
    .
  4. PMID 16484046
    .
  5. PMID 16169219
    .
  6. PMID 9525100
    .
  7. PMID 9988218
    .
  8. ^
    PMID 12802735
    .
  9. ^ Nierding, Axel. "Acide Maslinique: Propriétés Et Bienfaits" [Maslinic Acid: Properties And Benefits]. Polyvalents (in French). Retrieved 2023-12-25.
  10. PMID 31138956
    .
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