Stearidonic acid: A plant produced omega‐3 PUFA and a potential alternative for marine oil fatty acids

Abstract

Omega-3 (n-3) fatty acids are widely recognized as being important in regulating many inflammatory disorders in man. However, metabolism of the parent n-3 fatty acid a-linolenic acid (ALA, 18:3n-3) to the highly unsaturated bioactive fatty acids; eicosapentaenoic acid (EPA, 20:5n-3) and docosahexaenoic acid (DHA,, in the body is limited. The first product in the pathway leading to EPA/ DHA is the post-D6 desaturase metabolite stearidonic acid (SDA, 18:4n-3). The activity of the D6-desaturase enzyme is low in man and can be adversely influenced by several environmental factors including dietary fat. SDA has been shown, in several studies, to be rapidly and efficiently converted to EPA which is a probable factor in its bio-activity. The main source of EPA and DHA in diet is fish oil which, owing to over-fishing and its extensive use in aquaculture feed, is becoming a scarce resource. There clearly exists a need for a renewable source of a lipid containing the highly unsaturated n-3 fatty acids EPA, DHA or SDA. Although the highly unsaturated fatty acids (HUFA) have been commercially produced in micro-organisms neither EPA nor DHA has been shown to exist in any quantity in land-based plants. SDA is however found in several fungal and algal species and also in a small number of plant seed oils. Plants from the Boraginaceae family notably Echium species are particularly rich in SDA and Echium plantagineum has been grown commercially. Other plants from the Boraginaceae are being investigated and several have been identified that may offer benefits over Echium spp. Transgenic plants containing high levels of SDA have also been reported but engineering EPA or DHA into genetically modified higher plants is proving elusive. SDAcontaining lipids are of great interest in a number of areas such as fortified foods, dietary supplements, medicinal foods, pharmaceuticals and personal-care products.

Enzymatic production of human milk fat analogues containing stearidonic acid and optimization of reactions by response surface methodology

“…ALA conversion is relatively poor because of the high percentage of ALA directed towards boxidation, which is approximately 60e85% of ALA (Barceló-Coblijn & Murphy, 2009). Besides, SDA shows similar health effects like EPA and DHA; it is an important component of membrane phospholipids and is the precursor of some eicosanoids like prostaglandin E2 (Senanayake & Fichtali, 2006;Coupland, 2008;Whelan, 2009;Guil-Guerrero, Rincón-Cervera, & Venegas-Venegas, 2010). For these reasons, SDA rich plant-originated sources can be useful for replacement of fish oils and other PUFA containing oils for inclusion in infant formulae or for their use as functional lipids in the food and pharmaceutical industry.…”

“…Richest sources for those fatty acids are fishes and algae (Akoh, Lee, & Fomuso, 1998;Russo, 2009). However, as those sources are getting limited each day, intensive research on alternative sources for PUFAs is being carried out (Ratledge, 2004;Coupland, 2008). These fatty acids can be found in different ratios in some plants.…”

Preparation of Highly Purified Stearidonic Acid from Echium Oil via an Enzymatic Method Combined with Preparative High Performance Liquid Chromatography

“…SDA can be converted to longer chain highly unsaturated fatty acid, and it has similar biological properties to eicosapentaenoic acid EPA and docosahexaenoic acid DHA 1 . There have been numerous studies of the concentration of n-3 PUFA such as EPA and DHA because of their physiological effects on cardioprotective mechanisms 2 5 .…”

Review of twelve West Africa medicinal plants: Active phytochemical combinations in direct biochemically wound healing process

“…The plant constituents also include gamma-linolenic acid (GLA), alphalinolenic acid (ALA), delta 6 fatty acid denaturase, delta 8 sphingolipid desaturase (Coupland, 2008).…”