Punicic acid

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Punicic acid
Punicic acid
IUPAC name 9Z,11E,13Z-octadeca-9,11,13-trienoic acid
Identifiers
CAS number
PubChem 5281126
SMILES CCCC\C=C/C=C/C=C\CCCCCCCC(=O)O
Properties
Molecular formula C18H30O2
Molar mass 278.43 g/mol
Melting point

44-45 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Punicic acid (also called trichosanic acid) is a polyunsaturated fatty acid, 18:3 (n-5). It is named for the pomegranate, (Punica granatum), and is obtained from pomegranate seed oil. It is also found in the seed oils of snake gourd and bitter gourd.[1]

Punicic acid is a conjugated linolenic acid or ClnA; i.e. it has three conjugated double bonds. It is chemically similar to the conjugated linoleic acids, or CLA, which have two. In lab rats, it was found that punicic acid was converted to the CLA rumenic acid (9Z11E-CLA).[2] In vitro, it shows anticancer activity against prostate cancer cells.[3] OLETF rats—a strain which becomes obese—remained relatively lean when punicic acid was added to their feed.[4] Fat cells undergo programmed cell death when exposed to punicic acid from bitter-gourd oil.[5]

[edit] See also

[edit] References

 The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.
  1. ^ Cyberlipid. POLYENOIC FATTY ACIDS. Retrieved on 2007-01-11.
  2. ^ Tsuzuki T, Kawakami Y, Abe R (Aug 2006). "Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid". J Nutr 136 (8): 2153–9. PMID 16857834. 
  3. ^ Lansky E, Harrison G, Froom P, Jiang W (2005). "Pomegranate (Punica granatum) pure chemicals show possible synergistic inhibition of human PC-3 prostate cancer cell invasion across Matrigel". Invest New Drugs 23 (2): 121–2. doi:10.1007/s10637-005-5856-7. PMID 15744587. 
  4. ^ Arao K, Wang Y, Inoue N, Hirata J, Cha J, Nagao K, Yanagita T. "Dietary effect of pomegranate seed oil rich in 9cis, 11trans, 13cis conjugated linolenic acid on lipid metabolism in obese, hyperlipidemic OLETF rats". Lipids Health Dis 3: 24. doi:10.1186/1476-511X-3-24. PMID 15533261. 
  5. ^ Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K. "Regulation of apoptosis through arachidonate cascade in mammalian cells". Appl Biochem Biotechnol 102-103 (1-6): 239–50. doi:10.1385/ABAB:102-103:1-6:239. PMID 12396127. 
  • Punicic acid makes up around 65% of the fatty acids in pomegranate seed oil.
    Punicic acid makes up around 65% of the fatty acids in pomegranate seed oil.
  1. ^ Cyberlipid. POLYENOIC FATTY ACIDS. Retrieved on 2007-01-11.
  2. ^ Tsuzuki T, Kawakami Y, Abe R (Aug 2006). "Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid". J Nutr 136 (8): 2153–9. PMID 16857834. 
  3. ^ Lansky E, Harrison G, Froom P, Jiang W (2005). "Pomegranate (Punica granatum) pure chemicals show possible synergistic inhibition of human PC-3 prostate cancer cell invasion across Matrigel". Invest New Drugs 23 (2): 121–2. doi:10.1007/s10637-005-5856-7. PMID 15744587. 
  4. ^ Arao K, Wang Y, Inoue N, Hirata J, Cha J, Nagao K, Yanagita T. "Dietary effect of pomegranate seed oil rich in 9cis, 11trans, 13cis conjugated linolenic acid on lipid metabolism in obese, hyperlipidemic OLETF rats". Lipids Health Dis 3: 24. doi:10.1186/1476-511X-3-24. PMID 15533261. 
  5. ^ Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K. "Regulation of apoptosis through arachidonate cascade in mammalian cells". Appl Biochem Biotechnol 102-103 (1-6): 239–50. doi:10.1385/ABAB:102-103:1-6:239. PMID 12396127.