An octadecatetraenoic acid having four double bonds located at positions 6, 9, 12 and 15 (the all-cis-isomer). It has been isolated from Lithospermum officinale and fish oils.

Identification

IUPAC Names

(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoic acid

Molecular Formula
C18H28O2
Mass
276.41370
Monoisotopic Mass
276.20893
Charge
0
InChI
InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,12-13H,2,5,8,11,14-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,13-12-
InChIKey
JIWBIWFOSCKQMA-LTKCOYKYSA-N
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(O)=O
Synonyms

(6Z,9Z,12Z,15Z)-Octadecatetraenoic acid

6,9,12,15-Octadecatetraenoic acid

SDA

stearidonic acid

Species

daphnia galeata

NCBI:txid27404Is the fatty acid composition of Daphnia galeata determined by the fatty acid composition of the ingested diet?Weers P.M.M., Siewertsen K., and Gulati R.D.Freshwater Biology (1997), 38, 731-738

oryza sativa

homo sapiens

bos taurus

sus scrofa

drosophila melanogaster

ixodes scapularis

marine plankton environmental sample

aeromonas veronii

rattus norvegicus

cryptomeria

synechococcus elongatus pcc 7942

bos grunniens

malus domestica

arabidopsis thaliana

ctenopharyngodon idella

felis catus

microcystis aeruginosa

Europe PubMed Central results


Increase in stearidonic acid by increasing the supply of histidine to oleaginous Saccharomyces cerevisiae.

Author: Kimura K, Kamisaka Y, Uemura H, Yamaoka M.

Abstract: Increasing concentration of histidine significantly increased stearidonic acid production and cell growth in oleaginous Saccharomyces cerevisiae that has been genetically modified by Δsnf2 disruption, DGA1 and Δ6 desaturase gene overexpression, and LEU2 expression. High concentration of histidine in wild-type transformant and HIS3 expression in Δsnf2 transformant also increased stearidonic acid.

Dietary echium oil increases long-chain n-3 PUFAs, including docosapentaenoic acid, in blood fractions and alters biochemical markers for cardiovascular disease independently of age, sex, and metabolic syndrome.

Author: Kuhnt K, Fuhrmann C, Köhler M, Kiehntopf M, Jahreis G.

Abstract: Dietary supplementation with echium oil (EO) containing stearidonic acid (SDA) is a plant-based strategy to improve long-chain (LC) n-3 (ω-3) polyunsaturated fatty acid (PUFA) status in humans. We investigated the effect of EO on LC n-3 PUFA accumulation in blood and biochemical markers with respect to age, sex, and metabolic syndrome. This double-blind, parallel-arm, randomized controlled study started with a 2-wk run-in period, during which participants (n = 80) were administered 17 g/d run-in oil. Normal-weight individuals from 2 age groups (20-35 and 49-69 y) were allotted to EO or fish oil (FO; control) groups. During the 8-wk intervention, participants were administered either 17 g/d EO (2 g SDA; n = 59) or FO [1.9 g eicosapentaenoic acid (EPA); n = 19]. Overweight individuals with metabolic syndrome (n = 19) were recruited for EO treatment only. During the 10-wk study, the participants followed a dietary n-3 PUFA restriction, e.g., no fish. After the 8-wk EO treatment, increases in the LC n-3 metabolites EPA (168% and 79%) and docosapentaenoic acid [DPA (68% and 39%)] were observed, whereas docosahexaenoic acid (DHA) decreased (-5% and -23%) in plasma and peripheral blood mononuclear cells, respectively. Compared with FO, the efficacy of EO to increase EPA and DPA in blood was significantly lower (∼25% and ∼50%, respectively). A higher body mass index (BMI) was associated with lower relative and net increases in EPA and DPA. Compared with baseline, EO significantly reduced serum cholesterol, LDL cholesterol, oxidized LDL, and triglyceride (TG), but also HDL cholesterol, regardless of age and BMI. In the FO group, only TG decreased. Overall, daily intake of 15-20 g EO increased EPA and DPA in blood but had no influence on DHA. EO lowered cardiovascular risk markers, e.g., serum TG, which is particularly relevant for individuals with metabolic syndrome. Natural EO could be a noteworthy source of n-3 PUFA in human nutrition.