Acido diomo-gamma-linolenico

Acido diomo-gamma-linolenico
Nome IUPAC
acido (8Z,11Z,14Z)-icosa-8,11,14-trienoico
Abbreviazioni
20:3Δ8c,11c,14c , DGLA
Caratteristiche generali
Formula bruta o molecolareC20H34O2
Massa molecolare (u)306,482 g/mol
Numero CAS1783-84-2
Numero EINECS217-233-0
PubChem5280581
DrugBankDBDB00154
SMILES
CCCCCC=CCC=CCC=CCCCCCCC(=O)O
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

L'acido diomo-gamma-linolenico o diomo-γ-linolenico, in sigla DGLA, è un acido grasso polinsaturo con 20 atomi di carbonio e 3 doppi legami cis in posizione 8, 11, e 14. Appartiene alla classe degli omega-6. Si trova in piccole quantità (<5%) in alcuni funghi del genere Mortierella o Condiobolus[1] e negli oli di semi di diverse piante[2]:

Negli animali come nelle piante è normalmente prodotto dall'acido γ-linolenico in una reazione di allungamento della catena catalizzata da un enzima elongasi. Con diverse reazioni enzimatiche può contribuire alla sintesi degli eicosaoidi con rilevanti effetti biologici e clinici.[3][4] Catalizzato dall'enzima Δ5-desaturasi può formare acido arachidonico. Catalizzato dagli enzimi ciclo-ossigenasi 1(COX1) può formare prostaglandine del tipo 1 (PGE1).[5] Catalizzato dall'enzima lipo-ossigenasi 15 (15LOX) può formare acido 15 idrossieicosatrienoico (15HETrE).

Note

  1. ^ Cyverlipid: Polyenoic acids, su cyberlipid.org. URL consultato l'11 giugno 2017 (archiviato dall'url originale il 30 settembre 2018).
  2. ^ Max Rubner Institut - SOFA: Seed oil fatty acid database, su sofa.mri.bund.de. URL consultato l'11 giugno 2017 (archiviato dall'url originale il 9 novembre 2018).
  3. ^ Fan Yang-Yi, Robert S. Chapkin, Importance of Dietary γ-Linolenic Acid in Human Health and Nutrition, in Journal of Nutrition, vol. 128, n. 9, 9 settembre 1998, pp. 1411–4, PMID 9732298.
  4. ^ Drugbank Canada: Dihomo gamma-linolenic acid
  5. ^ Levin G., Duffin K. L., Obukowicz M. G., Hummert S. L., Fujiwara H., Needleman P. e Raz A., Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2., in Biochem J., vol. 15, n. 365, 2002, pp. 489-96.
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