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Docosapentaenoic acid

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Docosapentaenoic acid designates any straight chain 22:5 fatty acid.

Isomers

See essential fatty acid#nomenclature for nomenclature.

all-cis-4,7,10,13,16-docosapentaenoic acid (osbond acid)

The chemical structure of osbond acid showing physiological numbering (red) and chemical numbering (blue) conventions.


all-cis-4,7,10,13,16-docosapentaenoic acid is an ω-6 fatty acid with the trivial name osbond acid. It is formed by an elongation and desaturation of arachidonic acid 20:4 ω-6.

all-cis-7,10,13,16,19-docosapentaenoic acid (clupanodonic acid)

The chemical structure of clupanodonic acid showing physiological numbering (red) and chemical numbering (blue) conventions.


all-cis-7,10,13,16,19-docosapentaenoic acid is an ω-3 fatty acid with the trivial name clupanodonic acid, commonly called DPA. It is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source.[1]

Nutrition

Docosapentaeonic acid (DPA) is an omega-3 fatty acid that is structurally similar to EPA with two more carbon chain units. Many chronic diseases have an inflammatory component, and studies indicate that DPA has crucial anti-inflammatory properties. [2]

Dietary sources

These are the top five sources for DPA according to the USDA Agricultural Research Service: [3]

  1. Fish oil, menhaden .668 22:5 n-3 (DPA) (g) Per Measure
  2. Fish oil, salmon .407 22:5 n-3 (DPA) (g) Per Measure
  3. Salmon, red (sockeye), filets with skin, smoked (Alaska Native) 0.335 22:5 n-3 (DPA) (g) Per Measure
  4. Fish, salmon, Atlantic, farmed, raw .334 22:5 n-3 (DPA) (g) Per Measure
  5. Beef, variety meats and by-products, brain, cooked, simmered 22:5 n-3 (DPA) (g) Per Measure

Seal oil is also a major source of DPA. DPA represents approximately 5% by weight of the total seal oil. [4]

Docosapentaenoic acid deficiency

In mammals, clupanodonic acid (ω-3 fatty acid) deficiency is accompanied by an increase of the osbond acid (ω-6 fatty acid) isomer; the Osbond/DHA ratio is thus a marker of dietary DHA sufficiency.[5] However, this usage has been questioned.[6]

References

  1. ^ Ho, Cosmos. "The Studies of Seal Oil". The Benefits of Omega 3 Fatty Acids found In Seal Oil, as Opposed to Fish and Flaxseed Oils. Newfoundland Health Foods. Retrieved December 24, 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  2. ^ Byelashov, Alex. “DPA: An Up-and-Coming Fatty Acid.” Supply Side Insights. 2013
  3. ^ “DPA Nutrient List.” National Nutrient Database for Standard Reference Release 27.
  4. ^ “What types of omega-3 fatty acids are in seal oil?” DHA/EPA Omega-3 Institute. 2013.
  5. ^ Hornstra, Gerard; Al, Monique D.M.; Houwelingen, Adriana C.v.; Foreman-van Drongelen, Magritha M.H.P. (1995). "Essential fatty acids in pregnancy and early human development". Eur. J. Obstet. Gynecol. Reprod. Biol. 61 (1): 57–62. doi:10.1016/0028-2243(95)02153-J. ISSN 0301-2115. Retrieved December 24, 2013.Closed access icon
  6. ^ Innis, Sheila M; Vaghri, Ziba; King, D Janette (September 2004). "n−6 Docosapentaenoic acid is not a predictor of low docosahexaenoic acid status in Canadian preschool children1,2,3". Am. J. Clin. Nutr. 80 (3): 768–773.Open access icon

See also


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