Punicic acid

Uses

Punicic acid is a bioactive compound of pomegranate seed oil. Punicic acid is an isomer of conjugated α-linolenic acid and ω-5 polyunsaturated fatty acids. Punicic acid has anti-inflammatory and antioxidant activities and can inhibit the expression of inflammatory mediators such as tumor necrosis factor α (TNF-α). Punicic acid can also reduce the formation of β-amyloid deposits and hyperphosphorylation of tau by increasing the expression of GLUT4 protein and inhibiting the overactivation of calpain, and is used to prevent and treat neurodegenerative diseases. In addition, punicic acid also has breast cancer inhibitor properties that depend on lipid peroxidation and PKC pathways[1][2][3][4].

Definition

ChEBI: A 9,11,13-octadecatrienoic acid having its double bonds in cis, trans and cis configurations, respectively. It has been isolated from pomegranate (Punica granatum).

Synthesis

[1] put 1000g of pomegranate seeds into the extractor for supercritical CO2 extraction, extraction pressure 25MPa, extraction temperature 45 , separation pressure 9MPa, separation temperature 60 , to get 140g of pomegranate seed oil; [2] the pomegranate oil mixed with 5% sodium hydroxide solution, reflux for 1.6 hours, to get the fatty acid salt mixture; [3] hydrochloric acid acid will be fatty acid salt mixture acidified to pH value of 3.5, to obtain mixed fatty acids; [4] will be [3] to get the mixed fatty acids washed to neutral; [5] will be urea and methanol according to urea: methanol 1:3 stirring reflux until the urea is completely dissolved, and then slowly poured into the mixed fatty acids obtained in step (4), at -10 , stand for 12 hours; stand for vacuum filtration, the cake to remove the urea to get the saturated fatty acids; the filtrate to remove methanol The content of 92% garnet acid was obtained.

in vivo

References

[1] Shabbir MA, et al. Punicic acid: A striking health substance to combat metabolic syndromes in humans. Lipids Health Dis. 2017;16(1):99. DOI:10.1186/s12944-017-0489-3
[2] Boussetta T, et al. Punicic acid a conjugated linolenic acid inhibits TNFα-induced neutrophil hyperactivation and protects from experimental colon inflammation in rats[J]. PloS one, 2009, 4(7): e6458. DOI:10.1371/journal.pone.0006458
[3] Guerra-Vázquez, et al. Punicic acid and its role in the prevention of neurological disorders: A review. Foods 11.3 (2022): 252. DOI:10.3390/foods11030252
[4] Grossmann, et al. Punicic acid is an ω-5 fatty acid capable of inhibiting breast cancer proliferation. International journal of oncology 36.2 (2010): 421-426. PMID:20043077