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Nut Bioactives: Phytochemicals and Lipid-Based Components of Brazil Nuts, Cashews, Macadamias, Pecans, and Pine Nuts

Nut Bioactives: Phytochemicals and Lipid-Based Components of Brazil Nuts, Cashews, Macadamias, Pecans, and Pine Nuts

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214



Fruit and Cereal Bioactives: Sources, Chemistry, and Applications



Brazil nut (Bertholletia excelsa H.B.K.)

Figure 10.1  (See color insert) Brazil nut.



most extensively in confections (Sun et al. 1987). The Brazil nut is also used to produce oil, soaps, and

shampoos and for the cosmetic industries (Bonelli et al. 2001).

The Brazil nut has a well-known nutritional value due to its high content of lipids (50–70%), proteins

(1020%), and carbohydrates (1020%; Elias and Bressani 1961; Gonỗalves et al. 2009); it is high in

essential fatty acids (mainly oleic and linoleic acids), amino acids containing sulfur (particularly methionine and cysteine), vitamins (A and E), fibers and minerals such as zinc and especially selenium. In

fact, the Brazil nut is the best source of selenium from plant-based foods; selenium is a mineral needed

for proper thyroid and immune function and it is known for its antioxidant activity (Nwanna et al. 2008).

Brazil nuts promote diverse benefits to the health of humans owing to its anticarcinogenic properties (Ip

and Lisk 1994). This effect seems to be related to the high content of selenium, mainly present in the

form of Se-methionine, which is in a bioavailable form, and is also associated with compounds of low

molecular weight (Kannamkumarath et al., 2002).



Phenolics

There is a lack of information regarding the phenolics profile in a Brazil nut. However, the total phenolic

content has been determined with the Folin-Ciocalteu method (112 mg/100 g of gallic acid equivalents)

and summing the free and the bound phenolic contents (169 mg/100 g of the nut; Kornsteiner et al. 2006;

Yang et al. 2009). The total flavonoid content was found to be ~108 mg/100 g (Yang et al. 2009). The

content of phytoestrogens (isoflavones + lignans, mainly genistein and secoisolariciresinol) has been

reported to be ~0.9 mg/100 g of the dry nut (Kuhnle et al. 2008).



Neutral Lipids

Brazil nuts have a high oil content (>65%; Miraliakbari and Shahidi, 2007, 2008). Triacylglycerols (TGs)

are the major lipid class (>95 g/100 g oil; 2007). Over 20 TGs have been identified in Brazil nut oil,

which include: POL, SOL, OOO, PLP, POO, PoOO, PPoO, PoPoO, and SOO, together they account for

~80% of the total TGs content (Rodrigues et al. 2005).

The mean fatty acid composition (%) of a Brazil nut is reported in Table 10.1. The Brazil nut contains

an especially high concentration of palmitic and stearic acids (13.8 and 10.9%, respectively). The saturated fat content of a Brazil nut is the highest among all nuts (~20% of total fat). Oleic and linoleic acids

together account for more than 70% of the total fatty acids content (Miraliakbari and Shahidi 2007;

Chunhieng et al. 2008; Yang et al. 2009). The content of the ω-3 fatty acid (α-linolenic acid) is near 7%

of total fat (Yang 2009).



Polar Lipids

Brazil nut oil contains ~2% of polar lipids (Miraliakbari and Shahidi 2007). Among polar lipids, phospholipids (phosphatidylinositol, phosphotidylcholine, phosphatidylethanoalmine, phosphotidylserine

and phosphatidic acid) are the main class. Phosphatidylinositol and phosphotidylcholine range from

16 to 31% and 24 to 53% of total phospholipids content, respectively. Phosphotidylserine, phosphatidic

acid, and phosphatidylethanoalmine account for about 30, 24, and 21% of total phospholipids content,



215



Nut Bioactives

Table 10.1

Mean Content (%) of the Major Fatty Acid of Brazil Nut Oil

Fatty Acids



%



C 12:01

C 14:02

C 16:02

C 16:12

C 17:03

C 18:04

C 18:14

C 18:24



0.2

0.1

13.8

0.3

0.2

10.9

35.4

38.3



C 18:35

C 20:06

C 20:16

C 22:07

C 22:17



0.2

0.5

0.2

0.1

0.3



Source: Data reported by: 1,2,4  Chunhieng, T., Hafidi, A., Pioch, D.,

Brochier, J., and Montet, D., J. Braz. Chem. Soc., 19, 1374–80,

2008; 2,4,6  Miraliakbari, H. and Shahidi, F., J. Food Lipids, 15,

81–96, 2007; 2–7  Yang, J., Liu, R. H., and Halim, L., LWT-Food Sci.

Technol., 42, 1–8, 2009.



Table 10.2

Content (mg/ g of Oil) of Major Sterols of the Brazil Nut Oil

Sterols



Phillips et al. (2005)



Miraliakbari and

Shahidi (2007)



Yang (2009)



nd

0.65

0.06

0.02

0.13

0.86



0.12

1.11

0.22

0.12

nd

1.57



nd

1.32

0.58

0.03

nd

1.93



Cholesterol

β-sitosterol

Stigmasterol

Campesterol

Δ5-avenasterol

Total

Note: nd: not detected.



respectively (Miraliakbari and Shahidi 2007; Chunhieng et al. 2008). Sphingolipids are present in small

amounts (<1% of total lipid content).



Phytosterols and Tocols

The total sterols content of Brazil nut oil ranges from 0.9 to 1.9 mg/g (Phillips et al. 2005; Miraliakbari

and Shahidi 2007; Yang 2009). The main phytosterol is β-sitosterol, followed by stigmasterol, campesterol, and Δ5-avenasterol (Table 10.2). Moreover small amounts of 22-nordehydrocholesterol, 24-methylenecholesterol, and Δ7-stigmasterol have also been detected (Miraliakbari and Shahidi 2007; Chunhieng

et al. 2008).

The total tocopherols content is ~20 mg/100 g of the nut (Kornsteiner et al. 2006; Miraliakbari and

Shahidi 2007; Yang 2009). The γ-tocopherol is the major tocopherol (~15 mg/100 g of nut) followed by

α- and δ-tocopherol (~2 and 1 mg/100 g of the nut, respectively). Synergistic effects of Se and vitamin

E as well as other antioxidants play an important role in the prevention of prostate cancer cells (Zu and

Ip 2003).



216



Fruit and Cereal Bioactives: Sources, Chemistry, and Applications



Cashew (Anacardium occidentale L.)

Figure 10.2  (See color insert) Cashew nut.



Cashew

The cashew (Anacardium occidentale L.) (Figure 10.2) is one of the nut crops cultivated in the

tropical regions of India, Brazil, and Africa. India is the largest producer and exporter of the cashew

kernel, accounting for almost 50% of the world export (Paramashivappa et al. 2001). The kernel of

a cashew nut valued in trade is covered with a thin reddish-brown skin or testa. The testa has been

reported to be a good source of hydrolysable tannins (Pillai et al. 1963) with catechin and epicatechin

as the major polyphenols (Mathew and Parpia 1970). There are many reports describing the radical

scavenging activities of the by-products of a cashew nut (Amorati et al. 2001; Trevisan et al. 2006;

Kamath and Rajini 2007).

The cashew nut is a good source of proteins (20%), carbohydrates (23%), and fats (45%; Bhattacharjee

et al. 2003). Of the fat, 56% is oleic acid (ω-9) and 18% is linoleic acid (ω-6; Venkatachalam and Sathe

2006; Mexis and Kontominas 2009; Yang 2009). The consumption of cashew nuts may prevent cardiovascular diseases and lower low density lipoprotein (LDL) without affecting high density lipoprotein

(HDL; Baggio et al. 1988).



Phenolics

The cashew nut shell liquid is a viscous liquid that surrounds the edible kernel of a cashew nut. It is an

important by-product of cashew nut production, which is used in many industrial applications such as

paints, foundry chemicals, and special coatings (Menon et al. 1985) and even for gasoline stabilization

(Castro Dantas et al. 2003). The major phenolic constituents of the cashew nut shell liquid are anacardic

acids that have antioxidant and antitumor activities and cardols and cardanols that have uses in polymer

formulations and resins (Kubo et al. 1993; Ikeda et al. 2002; Kubo et al. 2006). Cashew nut shell liquid

contains ~350 g/kg of alkyl phenols, anacardic acids while the cashew nut has only 0.6 g/kg of hydroxy

alkyl phenols (Trevisan et al. 2006).

The total phenolic content of the cashew skin and nut is ~240 mg GAE/g of skin and ~137 mg

GAE/100 g of the nut, respectively (Kornsteiner et al. 2006; Kamath and Rajini 2007); more than 40% of

the total polyphenol in the skin is reported to be constituted by (+) catechin and (−) epicatechin (Mathew

and Parpia 1970). The total flavonoid content of the cashew nut is ~64 mg/100 g (~42 and ~22 mg/100 g

of free and bound flavonoids, respectively; Yang et al. 2009). Isoflavones and lignans are also present in

small amounts (0.012 and 0.170 mg/100 g of the dry nut; Kuhnle et al. 2008).



Neutral Lipids

The lipid content of a cashew nut ranges from 40 to 45% (Bhattacharjee et al. 2003; Venkatachalam and

Sathe 2006). Oleic and linoleic acids are the major fatty acids and in fact together account for ~75% of

total fatty acid content (Table 10.3). Palmitic and stearic acids represent, together, ~23% of total fatty

acids content. Palmitoleic and linolenic are present in small amounts (0.5 and 0.2%, respectively). Traces



217



Nut Bioactives

Table 10.3

Mean Content (%) of the Major Fatty Acids of Cashew Oil

Authors

Venkatachalam and Sathe (2006)

Mexis and Kontominas (2009)

Yang (2009)

Mean value



Palmitic

(C16:0)



Palmitoleic

(C16:1)



Stearic

(C18:0)



Oleic

(C18:1)



Linoleic

(C18:2)



Linolenic

(C18:3)



10.7

13.0

9.9

11.2



0.5

0.6

0.4

0.5



9.3

17.8

8.7

11.9



61.1

49.1

57.2

55.8



16.8

17.0

20.8

18.2



0.3

0.2

0.2

0.2



Macadamia (Macadamia tetraphylla)

Figure 10.3  (See color insert) Macadamia.



of myristic, pentadecanoic, heptadecanoic, elaidic, arachidic, behenic, and lignoceric acids have also

been detected (Mexis and Kontominas 2009; Yang 2009).



Polar Lipids

The cashew nut contains ~3% of polar lipids (Koaze et al. 2001). The classes of polar lipids found in

cashew nuts are cerebrosides and ceramides. The cerebroside concentration is ~0.04 mg/g of nut (Fang

et al. 2005). Sphingolipids are important in biological systems and have preventive effects on colon

­carcinogenesis (Merill et al. 1997).



Phytosterols and Tocols

The total phytosterols content of cashew nuts range from 1 to 2 mg/g of oil (Phillips et al. 2005; Yang

2009). The β-sitosterol represents ~89% of total sterols content, followed by stigmasterol and campesterol that together represent ~10% of total sterols content (Yang 2009). The Δ5-avenasterol, sitostanol,

and campestanol have also been detected (Phillips et al. 2005). Phillips et al. (2005) have found higher

levels of Δ5-avenasterol (~10% of total sterols content) and smaller amounts of stigmasterol (<1% of total

sterols content).

The mean content of total tocopherols is ~6 mg/100 g of oil. The γ-tocopherol account for more than

90% of total tocopherols content; α-, β-, and δ-tocopherol have also been detected (Kornsteiner et al.

2006; Yang 2009).



Macadamia

The macadamia is a large evergreen tree indigenous to the coastal rainforests of Australia that belongs

to the botanical family of Proteaceae (Figure 10.3). Australia is the largest producer of macadamia nuts

followed by the United States and South Africa (Borompichaichartkul et al. 2009). There are two species, Macadamia tetraphylla and integrifolia, which produce edible nuts; these species are also known

as a rough-shell and a smooth-shell type, respectively, for their characteristic surface texture of the shells

(Koaze et al. 2002).



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Fruit and Cereal Bioactives: Sources, Chemistry, and Applications



The macadamia nut is rich in monounsaturated fatty acids, with oleic acid, which is claimed to be a

potent inhibitor of fatty acid and cholesterol synthesis (Natali et al. 2007), contributing to more than 70%

of the total fatty acids. This unsaturated fatty acid can help the decrease of cholesterol and triglyceride

levels, thus lowering the risk of heart disease (Grag et al. 2003).



Phenolics

The total phenolics content of a macadamia is about 498 mg/100 g of the nut (Yang et al. 2009). This

value is higher with respect to almonds, Brazil nuts, hazelnuts, and pistachio nuts. Moreover macadamias

have the highest bound phenolics content among nuts (~460 mg/100 g of the nut; Yang et al. 2009).



Neutral Lipids

The macadamia has a high oil content of about 75 mg/100 g of the nut (Kaijser et al. 2000; Yang 2009). The

major fraction of macadamia oil is represented by TGs accounting for about 80% of total lipids (Koaze

et al. 2001). Even if 20 TGs have been detected in macadamia oil, the 10 TGs reported in Table 10.4 accounted

for over 75% of the total TGs content (Holcapek et al. 2003; Lee et al. 2005; Rodrigues et al. 2005).

The fatty acids composition (%) of macadamia oil is reported in Table 10.5. The main fatty acid is oleic

ranging from 49.6 to 65.1%, followed by palmitoleic (17.3–30.8%) and palmitic (8.4–9.4%); together they

account for about 90% of total fatty acids content (Gummeson et al. 2000; Rodrigues et al. 2005; Yang

2009). Traces of eicosatrienoic acid (C20:3) and behenic acid (C22:0) have also been detected (Yang 2009).

Table 10.4

Content (%) of the Major Triacylglycerols of Macadamia Oil

Triacylglycerols

OOO

SOL + OOO

GOM + OOO

OPoO

OPO

PoOPo

GPoPo + POPo

OOS

POP



Holcapek et al. (2003)



Lee et al. (2003)



Rodrigues et al. (2005)



19.4

nd

19.4

16.1

9.9

8.2

6.1

nd

1.2



23.3

nd

nd

20.8

13.6

8.8

nd

6.5

5.8



nd

24.0

nd

21.6

14.4

6.7

nd

7.2

1.9



Notes: nd: not detected.

M: myristic, Po: palmitoleic, P: palmitic, L: linoleic, O: oleic, S: stearic, G: gadoleic.



Table 10.5

Fatty Acids Composition (%) of Macadamia Oil

Fatty acids

Myristic (C14:0)

Palmitic (C16:0)

Palmitoleic (C16:1)

Stearic (C18:0)

Oleic (C18:1)

Linoleic (C18:2)

Linolenic (C18:3)

Arachidic (C20:0)

Gadoleic (C20:1)

Note: nd: not detected.



Gummeson et al. (2000)

1.8

9.4

30.8

2.2

49.6

2.5

0.1

1.6

1.8



Rodrigues et al. (2005)

1.0

9.4

19.3

3.4

59.8

2.0

0.1

2.6

2.5



Yang (2009)

1.0

8.4

17.3

3.2

65.1

2.3

0.1

2.3

nd



219



Nut Bioactives



Polar Lipids

At maturity the Macadamia nut contains ~3% of polar lipids (Koaze et al. 2002). During drying and

roasting, polar lipids increase from 2 to 7% (Koaze et al. 2001). Thermal treatments are essential for the

preservation of the nuts and the development of their good flavor and taste. Among polar lipids, phospholipids (phosphatidylethanoalmine and phosphotidylcholine) are the main class accounting for ~85%

of total polar lipids, followed by cerebrosides (~7%), acylsteryl-glucosides (~6%) and steryl-glucosides

(~1%). Monoglycosyl-diglycerides have also been found in trace amounts (Koaze et al. 2002).



Phytosterols and Tocols

The total phytosterols content of cashew nut ranges from 1 to 1.9 mg/g of oil (Kaijser et al. 2000;

Phillips et al. 2005; Yang 2009). The β-sitosterol represents ~85% of total sterols content, followed by

Δ5-avenasterol (~10%), stigmasterol (~5%), and campesterol (~1%) (Kaijser et al. 2000; Yang 2009).

The mean content of total tocopherols is ~5 mg/100 g of oil. The α- and δ-tocopherol are the principal

vitamin E isomer found in the macadamia nut (Kaijser et al. 2000; Yang 2009).



Pecan

Pecans (Carya illinoinensis) (Figure 10.4), belonging to the Juglandaceae family, are an indigenous crop

of the United States. Pecans are distributed over an area of geographic and climatic variation extending

from northern Illinois and southeastern Iowa to the gulf coast of the United States (Villareal-Lozoya

et al. 2007). The United States produces more than 80% of the world’s pecans.

A pecan nut is a high-energy food (~690 kcal/100 g) as lipids [up to 75% (w/w)] and carbohydrates [up

to 18% (w/w)] make up the bulk of the seed kernel weight (Venkatachalam et al. 2007). Pecan nuts are

rich in proteins, vitamins, especially vitamin E, calcium, magnesium, potassium, zinc, fibers, and antioxidants (Taipina et al. 2009). Pecan oil is very low in saturated fatty acids (<9%), only high-oleic safflower

(4–8%) and canola (<7.0%) oils are lower (Toro-Vazquez et al. 1999). Pecan kernels may improve human

serum lipid profile and lower LDL levels, due to their high monounsaturated fatty acid content (Rajaram

et al. 2001). The presence of phenolic compounds with high antioxidant capacity in the kernel and shell

indicates that pecan can be considered an important dietary source of antioxidants, in fact the pecan has

been ranked among foods with the highest phenolic content (Wu et al. 2004).



Phenolics

The total phenolic content of pecans range from 1284 to 2016 mg of gallic acid equivalents/g of kernel,

depending on cultivar, grown location, and storage conditions (Wu et al. 2004; Kornsteiner et al. 2006;

Villareal-Lozoya et al. 2007).

Proanthocyanidins or condensed tannins have been reported in pecan kernels with a mean content of

34 mg of catechin equivalents/g of a defatted kernel (Villareal-Lozoya et al. 2007). These types of compounds have biological activities such as antioxidant and antimutagenic properties, which are affected by



Pecan (Carya illinoinensis)

Figure 10.4  (See color insert) Pecan.



220



Fruit and Cereal Bioactives: Sources, Chemistry, and Applications



the degree of polymerization, the monomer structure, and the bond type between monomers (Grimmer

et al. 1992).

The main phenolic compounds are gallic and ellagic acids, ranging from 0.6 to 1.3 mg/g and 2.5

to 4.7  mg/g of a defatted kernel, respectively. Catechin and epicatechin are present in trace amounts

(Villareal-Lozoya et al. 2007).



Neutral Lipids

Pecan nuts contain 70–75% of oil, depending on cultivars, growing conditions, maturity, variety, and past

productivity of the tree (Toro-Vazquez et al. 1999; Wakeling et al. 2001; Venkatachalam et al. 2007).

Triacylglycerols (TGs) represent the major lipid class (~96% of total lipid content; Miraliakbari and

Shahidi 2007).

In general, pecan oil is mainly composed of oleic acid (~65%), linoleic acid (~25%), and palmitic acid

(~6%) with small concentrations of palmitoleic, stearic, linolenic, and arachidic acids, which together

account for ~4% of total fatty acids content (Table 10.6). Margaric, gadoleic, behenic, and eicosatrienoic

acids have also been found in small amounts (<2%; Yang 2009).



Polar Lipids

Phospholipids are the main polar lipids class with a level of about 1 g/100 g of pecan oil. The sphingolipids content is ~0.4 mg/100 g of pecan oil. Phosphatidylcholine and phosphatidylserine are the most

abundant phospholipids (0.23–0.52 and 0.24–0.47 g/100 g of oil, respectively), followed by phosphatidylinositol (0.2–0.7 g/100 g of oil; Miraliakbari and Shahidi 2007, 2008).



Phytosterols and Tocols

The total phytosterols content of the pecan nut ranges from 1.5 to 2.0 mg/g of oil (Ryan et al. 2006;

Miraliakbari and Shahidi 2008; Yang 2009). The β-sitosterol represents ~80% of total sterols content,

followed by stigmasterol (~17%) and campesterol (~3%; Yang 2009).

The total tocopherols content range from 10 to 27 mg/100 g of pecan oil (Villareal-Lozoya et al. 2007;

Miraliakbari and Shahidi 2008; Taipina et al. 2009). Variables such as genetics, environment, maturity

and storage conditions may affect tocopherol content of pecans (Rudolph et al. 1992).



Table 10.6

Mean Content (%) of the Major Fatty Acids of Pecan Oil of Different Cultivars

Cultivars

Desirablea

Kiowaa

Pawneea

Shawneea

Western Schleyb

Wichitab

Mean value

a



Palmitic

(C16:0)



Palmitoleic

(C16:1)



Stearic

(C18:0)



Oleic

(C18:1)



Linoleic

(C18:2)



Linolenic

(C18:3)



Arachidic

(C20:0)



5.65

5.48

5.34

5.53

5.65

5.90

5.59



0.03

0.03

0.03

0.06

0.05

0.03

0.04



1.72

2.30

2.49

1.93

2.51

2.29

2.21



61.63

66.36

68.18

72.43

61.80

65.68

66.01



29.21

24.69

22.38

18.55

27.98

24.59

24.56



1.23

1.12

1.03

0.98

1.23

1.19

1.13



0.06

0.07

0.10

0.09

0.13

0.09

0.09



Venkatachalam, M., Kshirsagar, H. H., Seeram, N., Heber, D., Thompson, T. E., Roux, K. H., and Sathe, S. K., Journal

of Agricultural and Food Chemistry, 55, 9899–907, 2007; Villareal-Lozoya, J. E., Lombardini, L., and CisnerosZevallos, L., Food Chemistry, 102, 1241–9, 2007.

b Wakeling, L. T., Mason, R. L., D’Arcy, B. R., and Caffin, N. A., Journal of Agricultural and Food Chemistry, 49,

1277–81, 2001; Venkatachalam, M., Kshirsagar, H. H., Seeram, N., Heber, D., Thompson, T. E., Roux, K. H., and

Sathe, S. K., Journal of Agricultural and Food Chemistry, 55, 9899–907, 2007.



221



Nut Bioactives



Pinenut

The species of genus Pinus, largely diffused both in Europe and North America, produce seeds edible

with a good level of healthy substances. The most common pine seeds consumed by humans come from

five pine tree species: the European stone pine, Pinus pinea, the Mexican Pinus cembroides, the Asiatic

Pinus koraiensis and Pinus sibirica, and the Californian Pinus monophylla (Wolff and Bayard 1995;

Wolff and Marpeau 1997). Pinus pinea is the specie principally widespread in the Mediterranean area

(Spain, Portugal, Italy, Greece, Albania, and Turkey), where there is its highest production and consumption. It is called the “Stone Pine” and the “Umbrella Nut” as the tree grows in stony ground and shaped

like an umbrella. Pine nuts (Figure 10.5), are consumed raw and roasted and as ingredients in many

traditional dishes. They contain adequate amounts of all of the essential amino acids as recommended

by FAO/WHO for an adult (Venkatachalam and Sathe 2006), and are a source of several nutrients, such

as vitamins (B1, B2, and K) and minerals especially potassium and phosphorus (Dinsmore et al. 2003;

Nergiz and Dönmez 2004). The composition of the pine nut shows variation among the species and even

some subspecies, depending on geographical and climatic conditions (Sagrero-Nieves 1992).



Phenolics

Total phenolics contents of the chloroform/methanol extract, expressed as equivalents of gallic acid,

are about 423 mg/kg of oil equivalents (Miraliakbari and Shahidi 2008). This value is comparable with

those of Brazil nuts and higher with respect to almond, hazelnut, and pistachio oils (Miraliakbari and

Shahidi 2008).



Neutral Lipids

The pine nut oil content varies from 31 to 75%, depending on the species (Wolff and Bayard 1995;

Ruggeri et al. 1998; Nergiz and Dönmez 2004; Ryan et al. 2006; Miraliakbari and Shahidi 2008, Nasri

et al. 2009). Triacylglycerols (TGs) represent the major lipid class 96%, while diacylglycerol, polar lipids,

and free fatty acids are in lesser proportions (1.95%, 0.84%, and 0.93%, respectively; Nasri and Triki

2004; Miraliakbari and Shahidi 2007). The trioctadecylglycerols are the main TGs (65.8–77.2%) represented by LLO/LOL, OLnO, LLL, LOO, and LLPi, LOPi when the unusual polymethylene-interrupted

unsaturated fatty acids with a cis-5 ethylenic bond were identified (Table 10.7).

The high differences in the distribution of TGs, indicates that the TG content can vary among populations of the same species—even if they come from neighboring geographic areas—of different species,

and overall is influenced by the experimental conditions (Imbs and Long 1996; Nergiz and Dönmez

2004, Nasri et al. 2009; Adhikari et al. 2010).

Concerning the fatty acids composition, the presence of an uncommon series of polyunsaturated fatty

acids has been highlighted. Conifer nuts contain a series of C18 and C20 polyunsaturated fatty acids

in which the first double bond is in the Δ5 position, and the successive double bond is in the Δ9 or

Δ11 position (Wolff and Bayard 1995). Pinolenic (cis-5, cis-9, cis12 18:3) acids exerting diverse physiological functions are used for the prevention or amelioration of hypercholesterolemia, thrombosis, and



Pine nut (Pinus pinea)

Figure 10.5  (See color insert) Pine nut.



222



Table 10.7

TGs Distribution (% of Total TGs Content) in Pine Nuts of Different Origin and Species

Turkey



TGsb



Tunisia



Spain



France



Greece



Italy



Turkey



TGsc



Commercial

Pine Nut Oil



OLnO

LOL

LLL

PLO

OOO

POO

PLL

SLO

OLnL

SOO

PLnO

LPP

PLnL

OPP

POS

OSS

SLS

PSS



23.50

18.60

10.80

10.60

10.30

5.38

5.32

3.39

2.23

1.87

1.23

0.87

0.83

0.77

0.46

0.28

0.25

0.14



LLO

LOO

LLL

PLO

OLnO

POO

OOO

SOO

OLnL

LPP

OPP

LLLn

PLL

PLnLn

PLnL

POS

LLS

SLS



24.38

17.82

14.80

11.31

7.93

7.53

6.74

2.13

1.79

1.06

0.93

0.66

0.63

0.61

0.59

0.48

0.34

0.21



24.63

19.20

13.30

10.86

7.11

7.61

7.12

2.55

1.79

1.12

0.92

0.40

0.72

0.57

0.59

0.65

0.30

0.30



23.50

19.40

11.13

11.45

7.49

8.04

8.03

2.68

2.34

0.89

0.95

0.41

0.89

0.49

0.73

0.77

0.34

0.38



23.63

19.38

11.42

10.84

7.33

7.74

8.29

2.45

2.60

1.15

0.95

0.55

0.87

0.54

0.74

0.69

0.38

0.37



24.22

18.32

13.56

10.75

7.40

7.70

7.59

2.31

2.16

1.11

0.99

0.55

0.72

0.57

0.69

0.64

0.35

0.28



24.05

18.39

13.58

11.22

7.51

7.80

7.31

2.27

1.93

1.22

1.05

0.56

0.68

0.51

0.59

0.61

0.28

0.24



LLPi

OLL/LOL

LOPi

OOPi/OPiO

LLL

OLO/LOO

POL/PLO/OPL

PLL/LPL

OOO

PLPi/LPiP/LPPi

others

 

 

 

 

 

 

 



24.70

17.00

17.00

8.80

8.40

7.20

3.60

3.50

3.20

2.10

3.00

 

 

 

 

 

 

 



Nergiz, C. and Dönmez, I.. Food Chem., 86. 365–8. 2004.

Nasri, N., Tlili, N., Ammar, K. B., Khaldi. A., Fady. B., and Triki. S., International Journal of Food Sciences and Nutrition. 60 (S1), 161–9, 2009.

c Adhikari, P.. Zhu. XM., Gautam, A.. Shin. J. A., and Hu. J. N.. Food Chem., 119, 1332–8, 2010.

a



b



Fruit and Cereal Bioactives: Sources, Chemistry, and Applications



TGsa



223



Nut Bioactives

Table 10.8

Principal Fatty Acids of Pine Nut Oil and Related Rangea

Fatty Acids

C14

C16

C16:1

C17

C18

C18:1 9

C18:1 11

C18:2 5,9

C18:2 9,12

C18:3 5,9,12

C18:3 9,12,15

C20

C20:1 11

C20:2 5,11

C20:2 11,14

C 20:3 5,11,14

C22

C24

Total

Sum of Δ5

TSb

TMb

TPb



%

0.05

4.59

0.22

0.05

2.34

24.28

0.90

2.05

48.52

14.80

0.57

0.76

0.95

0.36

0.75

3.22

0.12

1.51

106.01

20.43

9.41

26.34

70.26



Range

0.00–0.05

3.27–6.49

0.09–0.35

0.03–0.05

1.60–3.47

14.37–38.60

0.22–2.03

0.14–3.62

44.84–59.60

0.35–21.78

0.17–1.51

0.40–1.33

0.74–1.37

0.10–0.76

0.49–0.99

0.90–7.09

0.11–0.13

0.00–3.02



 



Data reported by Wolff, R., and Bayard, C. C., J. Am. Oil Chem. Soc.,

72, 1043–6, 1995; Nergiz, C. and Dönmez, I., Food Chem., 86, 365–8,

2004; Venkatachalam, M. and Sathe, S. K., J. Agric. Food Chem., 54,

4705–14, 2006; Miraliakbari, H. and Shahidi, F., J. Food Lipids, 15,

81–96, 2007; Adhikari, P., Zhu, XM., Gautam, A., Shin, J. A., and Hu,

J. N., Food Chem., 119, 1332–8, 2010.

b TS: total saturated fatty acids; TM: total monounsaturated fatty acids;

TP: total polyunsaturated fatty acids.

a



hypertension (Sugano et al. 1994). The distribution of fatty acids, as well as for TGs, is influenced by

the species. Table 10.8 reports the distribution of the principal fatty acids of pine nut oil belonging to

different species. In most species oleic and linoleic acids are the principal acids accounting for about

70% followed by the pinoleic acid (about 17%). In Pinus pinea oleic, linoleic acids account for about

81%, followed by palmitic acid (about 6%). Moreover, in all species, the sum of all Δ5 unsaturated fatty

acids is high (about 23%) and the polyunsaturated fatty acids content is more than threefold higher with

respect to monounsaturated fatty acids, while in Pinus pinea the sum of all Δ5 unsaturated fatty acids

is about 3% and the ratio between polyunsaturated/ monounsaturated fatty acids is about 1.4 (Wolff

and Bayard 1995; Nergiz and Dönmez 2004, Venkatachalam and Sathe 2006; Miraliakbari and Shahidi

2007; Adhikari et al. 2010).



Polar Lipids

Sphingolipids are the main polar lipids with a level of about 0.28–0.57 g/100 g of pine nut oil.

Phosphatidylcholine and phosphatidylserine are the most abundant phospholipids (0.14–0.37 and



224



Fruit and Cereal Bioactives: Sources, Chemistry, and Applications



0.15–0.33 g/100 g of oil, respectively), followed by phosphatidylinositol (0.07–0.19 g/100 g of oil;

Miraliakbari and Shahidi 2007, 2008).



Phytosterols and Tocols

Sterols in pine nut oil range from 0.14 to 0.43 g/100 g of oil (Phillips et al. 2005; Miraliakbari and

Shahidi 2007; Nasri et al. 2007; Adhikari et al. 2010). The principal phythosterols are β-sitosterol (mean

content 0.172 g/100 g of oil, range 0.112–0.320), campesterol (mean content 0.031 g/100 g of oil, range

0.017–0.660), and Δ5-avenasterol (mean content 0.026 g/100 g of oil, range 0.007–0.040), followed by

stigmasterol, sitostanol. The presence of 22-nordehydrocholesterol, campestanol, Δ7-campesterol, clerosterol, Δ5,24 stigmastadienol, Δ7-avenasterol, cholesterol and others were reported also but in a minor

amount. The high level of Δ7-avenasterol in pine nuts from Greece, Italy, and Turkey is useful to discriminate the nuts from this origin (Miraliakbari and Shahidi 2007; Nasri et al. 2007).

Pine nut oil contains high levels of tocopherols, with a wide range of concentration from about 30 to

170 mg/100 g of oil. Seed coming from Spain has the highest level of tocopherols, while the ones

from Turkey have the lowest content The most frequent form of tocopherol is the γ-tocopherol (range

250–1680 mg/kg of oil), followed by the α-form (range 9–166 mg/kg), the β-form (about 23 mg/kg)

and δ-forms (range 22–59 mg/kg) (Miraliakbari and Shahidi 2007, 2008; Nasri et al. 2009; Adhikari

et al. 2010).



References

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Chemistry Society Perkin Transactions 2:2142–6.

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Chemists’ Society 38:450–2.

Fang, F., Ho, C., Sang, S., and Rosen, R. T. 2005. Determination of sphingolipids in nuts and seeds by a single

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