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
CAS Number	4373-41-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:66682 N
ChEMBL	ChEMBL201515 N
ChemSpider	66312 N
ECHA InfoCard	100.128.873
KEGG	C16939 N
PubChem CID	73659
UNII	E233J88OHQ Y
CompTox Dashboard (EPA)	DTXSID30905074
InChI 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
SMILES 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
Chemical formula	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 YN ?) 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] 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. 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.