Nutritional Composition of Flaxseeds

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This entry is adapted from the peer-reviewed paper 10.3390/foods11203307

Flaxseed (Linum usitatissimum L.) has gained worldwide recognition as a health food because of its abundance in diverse nutrients and bioactive compounds such as oil, fatty acids, proteins, peptides, fiber, lignans, carbohydrates, mucilage, and micronutrients. These constituents attribute a multitude of beneficial properties to flaxseed that makes its use possible in various applications, such as nutraceuticals, food products, cosmetics, and biomaterials.

bioactive compound biological activity food application Linum usitatissimum L

1. Introduction

Flaxseed (Linum usitatissimum L.), commonly known as flaxseed or linseed, is an annual crop mainly grown for oil, fiber, food, and feed purposes. The significance of this crop has greatly increased in the modern world because of its exceptional nutritive content with a strong biological activity that has made its use possible in various applications such as functional foods, health supplements, and skincare products ^[1]^[2]^[3]. The importance of flaxseed has also recently increased because of the newer trend of veganism among consumers all over the world and the number of social, ethical, religious, moral, environmental, and sustainability concerns associated with the consumption of animal-based products. Flaxseed is becoming increasingly famous as a superfood because of its beneficial role in regulating gut flora and alleviating symptoms of many human diseases, such as cardiovascular ailments, diabetes, neural disorders, menopause, skin problems, gastrointestinal issues, and even cancers ^[4]. Furthermore, the proteins and cyclic peptides of flaxseed have been found to possess preferable antioxidant, antihypertensive, anti-inflammatory, immuno-suppressive, and anti-diabetic properties ^[5].

2. Nutritional Composition of Flaxseeds

2.1. Lipids

Flaxseed oil (FO) is divided into monounsaturated, polyunsaturated, and saturated fractions on the basis of fatty acid components (Figure 1) ^[6]. It is mainly abundant in total unsaturated fatty acids (87.8–89.8%) in comparison with the small amount of saturated fatty acids ^[7]. An investigation of FO extracted with petroleum ether elucidated α-linolenic (C18:3, ω-3, 42.4%), linoleic (C18:2, ω-6, 26.2%), palmitic (C16:0, 12.9%) and stearic acids (C18:0, 10.7%) as the major constituents ^[8]. Previous studies, however, revealed a little higher amount of α-linolenic (ca. 49–53%) and oleic (C18:1, ω-9, ca. 16–21%) acids along with a lower linoleic acid level (ca. 15–17%) and ascribed this variation to the difference in environment and farming conditions ^[9]^[10]. On the other hand, when n-hexane was used as an extracting solvent by Ishag and Khalid ^[8], it produced contrasting results with greater linoleic acid (46.5%) and lower α-linolenic acid (11.6%), while 18.0% palmitic acid in FO. It has been revealed that α-linolenic acid contents of flaxseed varieties from New Zealand and Canadian origin approximate 60%, which is far greater than the varieties belonging to Pakistan, Ethiopia, Egypt, and the USA. This increase is attributed to the cool, humid environment and optimal cultural practices (Table 1) ^[7]^[11].

Figure 1. Overview of flaxseed bioactive compounds. (A) Proposed structure of KPI-ASF as RG-1 bridge-linked arabinans. (B) Proposed repeating unit of the acidic fraction gum (HR, RG-1, and HG refer to homorhamnan, rhamnogalacturonan-I, and homogalacturonan, respectively). (C) Proposed structure of KPI-EPF as xyloglucans. (D) Proposed structure of FM-NFG as arabinoxylans. (E) Flaxseed oil, phenolic acids, sterols, pigments, and tocochromanols. (F) Lignans and their metabolites. (G) Cyclolinopeptide-A, cyclolinopeptide-B, and alcalase-derived antioxidant peptide.

Alpha-linolenic acid (ALA) is an essential polyunsaturated fatty acid with omega carbon at position three, which cannot be synthesized by the human body itself. ALA is used in the synthesis of docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) through different biosynthetic pathways, which are required for the normal growth, development, and maintenance of the human body, especially the brain and skin. Flaxseed oil is a very important source of ALA, but it has been employed to a limited extent for human benefits because of its low conversion ratio to DHA and EPA, which is a big hurdle faced by the scientific community these days ^[12]. The bioavailability of ALA is also dependent on the form of flaxseed consumed. For example, it is greater in flaxseed oil than in its milled form or whole seed. Additionally, the high unsaturated fatty acid content of flaxseed makes it highly prone to oxidative damage during processing stages, which is another threat that needs to be addressed to take maximum advantage of its nutritional contents ^[12]. Moreover, another study reported an appreciable amount of phospholipids, including phosphatidylethanolamine (27–40%), phosphatidylinositol (29–32%), phosphatidylcholine (7–18%), lysophosphatidylcholine (8–21%), phosphatidylglycerol (1–4%) and phosphatidic acid (1–9%), along with a small amount of palmitic acid (about 5%) and stearic acid (about 3%) in the lipid portion of flaxseed ^[11].

Table 1. Protein, oil, and phenolic acid composition of flaxseed.

Composition of protein ^[13]^[14]
Amino acids	Flaxseed protein meal (g/100 g)	Flaxseed protein hydrolysate (mg/g)
Alanine	4.59	n.a *
Arginine	10.63	33.12
Asparagine	9.76	496.51
Cysteine	3.80	n.a *
Glutamic acid	26.92	911.05
Glycine	6.14	288.43
Histidine	2.45	118.63
Isoleucine	5.21	207.49
Leucine	6.82	261.79
Lysine	4.18	191.41
Methionine	2.20	104.09
Phenylalanine	5.33	284.49
Proline	5.24	n.a *
Serine	5.88	n.a *
Threonine	4.19	169.94
Tryptophan	1.38	n.a *
Tyrosine	2.94	500.33
Valine	5.17	131.43
Composition of oil (%) ^[12]
Fatty acids	Flaxseed oil	Soybean oil
Myristic (C14:0)	0.03–0.05	n.a *–0.12
Pentadecanoic acid (C15:0)	n.a *–0.01	n.a *
Palmitic (C16:0)	4.58–6.42	10.80–11.50
Palmitoleic (C16:1)	0.04–0.20	n.a *–0.16
Margaric (C17:0)	n.a *–0.04	n.a *–0.04
Margaroleic (C17:1)	n.a *–0.03	n.a *
Stearic (C18:0)	3.65–5.96	3.62–4.11
Oleic (C18:1n-9)	16.33–22.56	20.80–23.50
Linoleic (C18:2n-6)	9.18–15.88	50.23–53.33
Linolenic (C18:3n-3)	42.97–61.06	6.76–7.65
Arachidic (C20:0)	0.01–0.20	n.a *–0.32
Gadoleic (C20:1)	n.a *–0.21	n.a *–0.22
Eicosanoic (C20:2)	n.a *–0.09	n.a *
Behenic (C22:0)	0.11–0.14	n.a *–0.27
Lignoceric (C24:0)	0.04–0.13	n.a *–0.13
Saturated	8.42–12.90	14.42–16.18
Total Monounsaturated	16.37–23.00	20.8–23.88
Total Polyunsaturated	52.15–76.94	56.99–60.98
Composition of phenolic acids and lignans (mg/100 g) ^[13]^[15]
	Non-defatted extracts	Defatted extracts
p-Hydroxybenzoic acid	1719	6454
Chlorogenic acid	720	1435
Ferulic acid	161	313
Coumaric acid	87	130
Gallic acid	29	17
Vanillic acid	22	42
Sinapic acid	18	27
Protocatechuic acid	7	7
Caffeic acid	4	15
Diphyllin	4.2	n.a *
Secoisolariciresinol diglucoside	1300	n.a *
Secoisolariciresinol	156	n.a *
Laricinesol	1.7	n.a *
Matairesinol	3.1	n.a *
Pinoresinol	0.8	n.a *
Composition of vitamins and pigments (µg/g) ^[16]^[17]
	Raw flaxseed	Boiled flaxseed
α-Tocopherol	6.26	4.56
β-Tocopherol	1.07	0.89
γ-Tocopherol	302.0	256.2
δ-Tocopherol	2.26	2.09
β-Carotenoid	0.52	0.48
Xanthophyll	27.1	20.2
Sprouted	LT001 ^a	Zhongya 4 ^a
Lutein	56.03	8.14
Zeaxanthin	2.38	2.76
β-Cryptoxanthin	1.64	1.86
ε-Carotene	1.44	1.61
β-Carotene	5.18	5.87

* n.a = data not available, ^a = variety.

The total sterol content of FO ranged from 4720 to 7550 mg/kg oil ^[18], from which sitosterol made the most quantity averaging almost 240 mg/100 g while campesterol and stigmasterol were other significant constituents averaging about 110 and 50 mg/100 g in corresponding order ^[19]. FO also contained significant quantities of 24-methylenecycloartanol, 25-hydroxy-24-methylcholesterol and cyclolanost-23-ene-3,25-diol ^[18]. Tocochromanols are another category of strong antioxidant compounds present in flaxseed oil, which besides being amphipathic, also possesses vitamin E activity ranging from 154–934 mg/kg by virtue of particular substances commonly called tocopherols and tocotrienols ^[20]. A huge variation in the vitamin E activity of FO was observed due to the difference in plant variety, location, growing, extraction, and storage conditions. Furthermore, this dual characteristic of tocochromonals for being hydrophilic and hydrophobic at the same time comes from a tyrosine-derived polar moiety and a poly-prenyl side chain, respectively. Tocotrienols are tocochromanols with a geranyl-geranyl side chain, while tocopherols possess a phytyl-side chain ^[21].

The total tocopherol content in Pakistani and Egyptian cultivars was greater than that of Canadian and American cultivars ^[7], which is an indication of their better antioxidant potential. Tocopherols are the fat-soluble vitamins (460–610 mg/kg) found in the greatest amount in FO, trailed by plastochromanol-8 (270–370 mg/kg), which is a functional analog of γ-tocotrienol and lastly α tocopherol that averages about 1–8 mg/kg ^[22]. The study also revealed that the γ-tocotrienol and plastochromanol-8 had a positive correlation, while δ-tocopherol had a negative correlation with temperature and amount of sunlight received during seed ripening. The cause behind this biological mechanism needs to be sought out for taking advantage of this relationship for human use ^[7].

2.2. Polysaccharides

FM is separated into two types of polysaccharide fractions on the basis of the net charge that is acidic and neutral. Arabinoxylans with β-D-(1,4)-xylan make the backbone of a neutral fraction, which is also free of uronic acid, while the acidic fraction is mainly composed of sugars, which are building blocks of pectic substances such as galactose, rhamnose, and galacturonic acid (Figure 1) ^[23]. The analysis of the chemical composition of FM from different genotypes showed that FM from yellow seeds had lower galacturonic acid (13–16%) and rhamnose (12–14%) contents, while higher neutral sugars like xylose (39–48%) content in contrast to FM obtained from brown seeds ^[24]. Moreover, it has been documented that the neutral fraction of FM with high molecular weight (MW; 1470 kDa) also contains uronic acids in a small amount (1.8%), which gives it a pseudo-plastic flow behavior ^[25].

The acidic fraction of FM is mostly constituted by two sub-fractions of rhamnogalacturonans, one with greater MW (1510 kDa) and the other with a lesser MW (341 kDa). The structure of rhamnogalacturonan from flaxseed hull was explicated through methylation analysis and 1D/2D NMR spectroscopy which showed it to be a structure consisting of rhamnogalacturonan-1 (RG-1) structure with diglycosyl repetition unit →2)-α-L-Rhap-(1→4)-α-D-GalpA-(1→as depicted in Figure 1 ^[26]. Six types of RG-1 from FM were obtained from ion-exchange chromatography and a light scattering detector ^[27]. Furthermore, MWs of acidic fractions were also determined through size exclusion chromatography as follows 756.4 kDa, 718.8 kDa, 505.6 kDa, 457.5 kDa, 354.8 kDa, and 593.2 kDa. However, the rhamnose to galacturonic acid ratio (1.22 to 0.85) and degree of branching (0.33 to 0.65) of the acidic fractions varied considerably. It was also revealed that RG-1 blocks are often singly substituted with sugars like galactose, fructose, rhamnose, or sometimes short, neutral monosaccharides. Polysaccharides in FM, when dissolved in water, attained random coil confirmation, the MWs of which fluctuated between 1.6 × 10⁶ and 1.0 × 10⁷ g/mol, whereas, in the salt solution, they adopted more regular, spherical, closed shapes, which differed in weight from the spiral and close confirmations MWs of which varied from 1.5 × 10⁶ to 4 × 10⁸ g/mol ^[28].

2.3. Protein/Peptides

Flaxseed is an abundant source of proteins, which make up to 23% of the total seed weight, and this amount increases to 35 to 40% in meal after oil extraction. A balanced amino acid combination of flaxseed gives it a high protein quality score (82%), which is even better than that of soybean ^[29]. Similarly, the lysine to arginine ratio of flaxseed of 0.37 is far lesser than that of soybean (0.88), which is indicative of its lower lipidemic and atherogenic potential and, thus, heart friendliness (Table 1) ^[29]. Flaxseed mainly contains two types of proteins, namely albumins and globulins, on the basis of solubility properties, which are also known as linins and colinins. Globulins make up 80% of total proteins. They consist of subunits with a high MW ranging between 252 and 298 kDa (18.6% nitrogen; 11–12S) and smaller percentages of alpha-helical (3%) and beta structures (17%) ^[30]^[31].

Flaxseed is considered a preferable source of protein because of the appreciable amounts of sulfur-based amino acids, such as cysteine and methionine; branched-chain amino acids, such as leucine, isoleucine, aline, and essential amino acids, such as tyrosine, threonine, and lysine. Flaxseed is rich in storage proteins such as aspartic acid, glutamine, asparagine, and arginine, like other seeds, which contribute to its high amide content ^[29]. Madhusudhan and Singh ^[30] isolated flaxseed globulins (FG) through SDS-PAGE in their investigation. It was found that FG contained five subunits with MW lying between 11 and 61 kDa and six subunits with MW lying between 41 and 55 kDa linked with disulfide bridges. When treated with mercaptoethanol, the larger subunits with MWs from 50 to 55 kDa disassociated into one acidic (40 kDa) and one basic smaller subunit (20 kDa). Likewise, five types of globulins were sorted in another study on the basis of MWs from flaxseeds with MWs of 14.4, 24.6, 30.0, 35.2, and 50.9 kDa, among which acidic subunits were a little bigger than basic subunits ^[32]. A large protein fraction (365 kDa) was isolated from defatted and dehulled flaxseed through anion-exchange chromatography, which was later separated into three more fractions (20, 23, and 31 kDa) when subjected to reducing SDS-PAGE. Four subunits of 11S globulin were identified from FP, which consisted of a pair of α- and β-chains linked with disulfide bonds ^[29]. A small amount of 7S globulin subunits (21 to 54 kDa) were also identified, along with other low MW (7 to 10 kDa) fractions.

Conlinins are a type of albumin found in the seeds of many plant species. It consists of a polypeptide chain with a 16–18 MW and a 1.6–2 sedimentation coefficient. These proteins have more organized confirmation due to greater disulfide bonds, which are overall composed of 26% α-helices and 32% β-structures ^[29]. Furthermore, these albumins are rich in lysine, arginine, cysteine, glutamine, and alanine ^[33]. Flaxseed is an important source of another group of proteins or peptides called cyclolinopeptides, orbitides, or linosurbs. There are more than 25 kinds of these compounds that have been distinguished ^[5]. Orbitides mostly consist of 8–10 amino acids. The structure of one famous Cyclolinopeptide-A is as follows: Pro-Pro-Phe-Phe-Leu-Ile-Ile-Leu-Val. These compounds have been found to possess multiple beneficial traits, such as being immunosuppressive, anti-malarial, anti-tumor, and a protectant against bone degeneration. Linosurbs are usually cyclic, hydrophilic in nature, linked with N-C bonds, and are named on the basis of the first amino acid or prolyl residue in the protein sequence. Orbitides are also present in many other plant species and are used for the chemical synthesis of methionine sulfones, alcohol, and acetonitrile solvates, which are useful for many health and biomedical uses ^[34].

2.4. Phenolic Compounds and Carotenoids

Phenolic substances possess numerous health advantages. Flaxseed has a variety of phenolic compounds, which are divided into two categories, namely phenolic acids and lignans (Table 1) and (Figure 1). The range of phenolic acids in a Canadian flaxseed variety was found to be varying between 790–1030 mg/100 g, out of which chlorogenic acid, p-hydroxy benzoic acid, ferulic acid, vanillic acid, and coumaric acid make the highest portion, while lignans, namely matairesinol, pinoresinol, diphyllin, and secoisolariciresinol made a smaller portion ^[13]^[35]. Lignans are low molecular weight phenolic dimers comprising of 2,3-dibenzylbutane as a base structure. They are mostly present in the outer coat of the seed ^[13]. Secoisolariciresinol diglucoside (SDG) is a major lignan in flaxseed averaging about 610–1300 mg/100 g ^[36]. Lignans are powerful anti-oxidant substances in flaxseed, which has made them the center of attention for many studies in recent times ^[37]. The phenolic acid composition of flaxseed before and after fat extraction is presented in Table 1, which shows that whole seeds have a lesser phenolic acid content than meal after oil extraction. The maximum recovery ratio of lignans was obtained by Gutiérrez and Rubilar ^[38] with 50% ethanol, 1:60 solid-to-liquid ratio, 30 min shaking, 200 rpm speed, and at 25 °C.

Carotenoids are organic compounds with 40-carbon atoms in many seeds and fruits, which gives them red, orange, and yellow colors, besides being precursors of vitamin A ^[39]. β-Carotene is one such important pigment that has the highest pro-vitamin A activity ^[40]. The carotenoid content of flaxseed was found to be 0.7–3.1 mg/kg; however, Farag and Elimam ^[41] reported a far greater amount of β-carotene in flaxseed oil (77 mg/kg). Furthermore, there is a positive correlation between the amount of tocochromanol and carotenoid levels in flaxseed and the number of sunshine hours received during the seed maturation phase. Carotenoids play a crucial role against photo-oxidation, and thus it holds special importance with reference to the high unsaturated lipid content of flaxseed.

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