Chemical Characteristics of Cold-Pressed ... - ACS Publications

Subscriber access provided by UNIV OF NEW ENGLAND ARMIDALE

Article

Chemical characteristics of cold-pressed blackberry, black raspberry and blueberry seed oils and the role of the minor components in their oxidative stability Quanquan Li, Jiankang Wang, and Fereidoon Shahidi J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/acs.jafc.6b01821 • Publication Date (Web): 20 May 2016 Downloaded from http://pubs.acs.org on June 5, 2016

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

Journal of Agricultural and Food Chemistry is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 31

1

Journal of Agricultural and Food Chemistry

For submission to: Journal of Agriculture and Food Chemistry

2 3

Chemical characteristics of cold-pressed blackberry, black raspberry and blueberry seed

4

oils and the role of the minor components in their oxidative stability

5 6 7

Quanquan Li1, Jiankang Wang2, Fereidoon Shahidi1,*

8 9 10

1

11

A1B 3X9

12

2

Departments of Biochemistry, Memorial University of Newfoundland, St. John’s, NL, Canada,

Northern Lights Biotechnology Ltd., St. John’s, NL, Canada, A1C 2H3

13 14 15

*Corresponding author. Email: [email protected]; Telephone: +1 (709) 864-8552.

16 17 18 19 20 21 22

1

ACS Paragon Plus Environment


23

ABSTRACT: The chemical characteristics of cold-pressed blackberry, black raspberry, and

24

blueberry seed oils were evaluated for their fatty acid composition, positional distribution of fatty

25

acids, triacylglycerol (TAG) profile and minor components profile. The role of minor

26

components, including tocols and pigments on the oxidative stability was also investigated using

27

high temperature and fluorescent lighting induced oxidation before and after tested berry seed

28

oils were stripped of their minor components. The results indicated that all tested berry seed oils

29

contained significant levels of palmitic (C16:0), stearic (C18:0), oleic (18:1), linoleic (C18:2n−6),

30

and α-linolenic (C18:3n−3) acids, along with a favorable ratio of n−6/n−3 fatty acids (1.49−3.86);

31

palmitic, stearic, oleic and α-linolenic were predominantly distributed on the terminal positions.

32

Six triacylglycerols, namely LnLnLn, LnLLn, LLLn, LLL, OLL and OLLn, were the major

33

species detected in the tested berry seed oils. Total tocol contents were 286.3−1302.9 mg/kg,

34

which include α-, γ-, and δ-tocopherols as well as δ-tocotrienol. Oxidative stability of the three

35

berry seed oils was compromised after the removal of tocols under high temperature induced

36

oxidation, while the loss of pigments (chlorophylls) led to weak oxidative stability when exposed

37

to fluorescent lights.

38 39

KEYWORDS: blackberry see oil, black raspberry seed oil, blueberry seed oil, fatty acids,

40

positional distribution of fatty acids, triacylglycerols, tocols, tocopherols, tocotrienols, pigments,

41

chlorophylls, carotenoids, oxidative stability

42 43

2


Page 2 of 31

Page 3 of 31

44


INTRODUCTION

45

Edible oils are essential macronutrients in food and a condensed source of energy. Edible

46

oils could also benefit human health by serving as a source of essential fatty acids, fat-soluble

47

vitamins and other nutrients and non-nutrient phytochemicals. Berry seed oils, such as

48

blackberry, black raspberry, and blueberry seed oils, are considered specialty oils, which may be

49

used in different products by the food, nutraceutical and cosmetic industries. These berry seed

50

oils are abundant in oleic acid, linoleic acid, and α-linolenic acid, and thus are a rich source of

51

essential polyunsaturated fatty acids (PUFA), and their potential health benefit has led to a rapid

52

commercial development of these oils in a variety of products and applications.1

53

Edible oils are primarily composed of triacylglycerols (TAG), around 95%, and minor

54

amounts of other components, including diacylglycerols (DAG), monoacylglycerols (MAG), free

55

fatty acids (FFA), phospholipids, tocols (tocopherols and tocotrienols), sterols, pigments, among

56

others.2 The fatty acids present in TAG are saturated, monounsaturated, or polyunsaturated, and

57

the degree of unsaturation is a main factor that dictates the oxidative stability of the oils. The

58

oxidative stability is also influenced by the positional distribution of fatty acids in the TAG, as

59

well as the minor components in oils and their storage conditions. The minor components, such

60

as tocols including tocopherols and tocotrienols, may play a role in protecting oils from

61

oxidation by serving as free radical scavengers, and their mechanisms of action in retarding

62

oxidation have been well-studied.3-5 In addition to neutralize free radicals, they may form

63

chelation complexes with transition metals, reducing peroxides, and stimulate antioxidative

64

defense enzymes in the body.6 Pigments, such as chlorophylls, can act as photosensitizers when

65

exposed to light, which leads to rapid oxidation of edible oils.7

3



66

Oxidative stability of cold-pressed blackberry, black raspberry and blueberry seed oils

67

has not been thoroughly studied, and the antioxidant/prooxidant effects of minor components in

68

the berry seed oils tested have been reported. In addition, there is no literature about the TAG

69

profiles of cold-pressed berry seed oils or their impact on oxidative stability. Therefore, the

70

objectives of this study were to characterize the cold-pressed berry seed oils by determining their

71

fatty acid composition, positional distribution of fatty acids, TAG profile and their minor

72

components, as well as to assess the effects of minor components on oxidative stability of the

73

oils.

74 75 76

MATERIALS AND METHODS

77

Materials. Cold-pressed seed oils of blackberry, black raspberry and blueberry were kindly

78

provided by Fruit Smart®, Inc. (Grandview, WA, USA).

79

thiobarbituric acid (2-TBA), gallic acid (3,4,5-trihydroxybenzoic acid), silicic acid powder (mesh

80

size: 100-200, acid-wash) and activated charcoal were obtained from Sigma Chemical Co. (St.

81

Louis, MO, USA). Tocopherols and Tocotrienols were kindly provided by Planning &

82

Development Department of Eisai Food & Chemical Co., Ltd. (Tokyo, Japan). Hexane,

83

acetonitrile, methanol, ethanol, sulfuric acid, isooctane, isopropanol, 1-butanol and all other

84

chemicals were obtained from Fisher Scientific Co. (Nepean, ON, Canada). All solvents were of

85

ACS grade.

86 87

4


Folin-Ciocalteu reagent, 2-

Page 4 of 31

Page 5 of 31


88

Methods

89

The Removal of Minor Components from Berry Seed Oils Using Column Chromatography.

90

Blackberry, black raspberry and blueberry seed oils were stripped of their minor components

91

according to the method described by Abuzaytoun and Shahidi with minor modifications.8 A

92

chromatographic column (3.4 cm internal diameter x 40 cm length) was packed sequentially with

93

45 g of activated silicic acid, followed by 45g of charcoal and another 45g of activated silicic

94

acid. The silicic acid (100 g), before introduction to the solvent, was activated by washing three

95

times with a total of 3 L of distilled water. After each treatment, the silicic acid was left to settle

96

for 30 min, and then liquid was discarded. The silicic acid was then washed with methanol and

97

the supernatant discarded.

98

Oil (60 g) was diluted with an equal volume of hexane and passed through the

99

chromatographic column. The solvent in the stripped oils was evaporated under vacuum at 50 °C,

100

and traces of the solvent were removed by flushing with nitrogen. The column-stripped oils were

101

then transferred into 10 mL glass vials, flushed with nitrogen, and kept at -80 °C for up to one

102

month prior to performing subsequent experiments.

103 104

Fatty Acid Composition. The fatty acid compositions of non-stripped and column stripped berry

105

seed oils were analyzed by gas chromatography-flame ionization detection (GC-FID). Fatty acids

106

were converted to fatty acid methyl esters (FAMEs) using 6% sulfuric acid in methanol,

107

according to the method of Wanasundara and Shahidi.9 FAMEs were analyzed using a Hewlett-

108

Packard 5890 series II gas chromatograph (Agilent, Palo Alto, CA, USA) equipped with a fused

5



109

capillary column. Results were expressed as weight percentage of each fatty acid in total fatty

110

acids.

111 112

Triacylglycerol Profiles. The high performance liquid chromatography–photodiode array

113

detection–atmospheric pressure chemical ionization-mass spectrometry (HPLC-DAD-APCI-MS)

114

determination of triacylglycerols (TAG) in tested seed oils was conducted according to the

115

method of Lisa and Holcapek with minor modifications.10 Berry seed oils were dissolved in

116

acetonitrile/2-propanol (1:1, v/v) to obtain a 3% (w/v) solution. The elution system was as

117

follows: 0 min, 100% A; 106 min, 31% A; 120 min, 100% A.

118 119

Positional Distribution of Fatty Acids

120

a. Selective Hydrolysis by Using Pancreatic Lipase. The oil samples were hydrolyzed using

121

pancreatic lipase as described by Christie with minor modifications.11 The oil (25 mg) was

122

weighed into a glass tube, and then 5.0 mL of Tris-HCl buffer (1.0 M, pH 8.0), 0.5 mL of

123

calcium chloride (2.2%), and 1.25 mL of sodium taurocholate (0.05%) were added. Porcine

124

pancreatic lipase (5.0 mg; EC 3.11.3) was added into the mixture after it had been kept in a water

125

bath for 5.0 min at 40 °C. The glass tube was subsequently placed in a gyratory water bath

126

shaker at 250 rpm under a blanket of nitrogen for 1 h at 40 °C. The enzymatic reaction was

127

stopped by adding 5.0 mL of ethanol, followed by the addition of 5.0 mL of 6.0 M HCl.

128

b. Extraction and Separation of Hydrolytic Products. Diethyl ether (50 mL in total) was used to

129

extract the hydrolytic products three times, and then the extract was washed twice with distilled

6


Page 6 of 31

Page 7 of 31


130

water and dried over anhydrous sodium sulfate followed by the removal of the solvent under

131

reduced pressure at 30 °C. The hydrolytic products were separated on silica gel thin-layer

132

chromatographic plates (Sigma-Aldrich, St. Louis, MO, USA). The plates were developed using

133

a mixture of hexane/diethyl ether/acetic acid (70:30:1, v/v/v) for 45−55 min. The free fatty acid

134

bands were scraped off and lipids extracted into diethyl ether, which were then used for fatty

135

acid analysis as described by Wanasundara and Shahidi.9

136 137

c. Fatty Acid Compositional Analysis of Hydrolytic Products. Fatty acid composition and

138

positional distribution of the products were determined following their conversion to the

139

corresponding methyl esters. A Hewlett-Packard 5890 series II gas chromatograph (Agilent, Palo

140

Alto, CA, USA) equipped with a Supelcowax-10 column (30 m length, 0.25 mm diameter, 0.25

141

µm film thickness; Supelco Canada Ltd., Oakville, ON, Canada) was used to analyze the FAMEs.

142

The FAMEs were identified by comparing their retention times with those of a known standard

143

mixture. Positional distribution of fatty acids at sn-1,3 positions was calculated as (% fatty acid

144

at sn-1,3 positions/% fatty acid in triacylglycerols) × 100.

145 146

Determination of Tocols. Tocol content in blackberry, black raspberry, and blueberry seed oils

147

were determined by reverse phase high performance liquid chromatography-mass spectrometry

148

(HPLC-MS). The analysis was performed using an Agilent 1100 HPLC system (Agilent

149

Technologies, Palo Alto, CA, USA), equipped with a UV-diode array detector (UV-DAD).

150

Separation was achieved on a C-18 column (4.6mm× 250mm coupled with a guard column,

7



151

Sigma). Tocols were eluted using a gradient solvent system containing methanol-acetonitrile-

152

isopropanol. Fifty microliters of each tocol standard and oil samples were used and detection was

153

followed at 295nm. The mobile phase started with methanol/acetonitrile/isoproponol (41:59:0,

154

v/v/v) at a flow rate of 0.8 ml/min and maintained for 15 min. The mobile phase was then

155

gradually changed to methanol/acetonitrile/isoproponol (16.5:23.5:60, v/v/v) from 15 to 25 min,

156

followed by gradual increase to 100% isoproponol from 25 to 35 min, which lasted 10 min. In

157

order to recondition the column, the mobile phase was changed to its initial state,

158

methanol/acetonitrile/isoproponol (41:59:0, v/v/v) in 5 min, and was kept there for 10 min. All

159

analyses were performed by using mass spectrometric detector system (LC-MSD-Trap-SL,

160

Agilent, Palo Alto, CA, USA) and alternating ion atmospheric pressure chemical ionization

161

(APCI). The operating conditions used were 121 V for the fragments, drying temperature of

162

350°C, APCI temperature of 400°C, nebulizer pressure of 60 psi, drying gas flow of 7 liter/min.

163

Tocopherol and tocotrienol concentrations in samples were calculated based upon standard

164

curves and expressed as (mg/kg of oil).

165 166

Measurement of Pigments. Pigments, present in the stripped and non-stripped oil samples were

167

determined by measuring the absorbance at 550-710nm for chlorophylls and their derivatives,

168

and 430-460 nm for carotenoids.8 The oil sample was mixed with hexane (1:1, v/v) and

169

transferred into cuvettes, and the absorbance was read using a 8453A UV-Visible

170

spectrophotometer (Agilent Technologies, Palo Alto, CA, USA).

171

8


Page 8 of 31

Page 9 of 31


172

Oxidative Stability Tests of the Original Berry Seed Oils and Their Stripped Counterparts

173

under Accelerated Oxidation Conditions Using Schaal Oven and Fluorescent Lighting. The

174

oxidative stability of stripped and non-stripped seed oils was examined under Schaal oven

175

conditions and fluorescent lighting respectively. The oxidative stability of the oils was

176

determined under Schaal oven (model 2, Precision Scientific Co., Chicago, IL, USA) conditions

177

at 60°C for 7 days. Each day (24 h) of storage under such conditions is equivalent to 1 month of

178

storage at ambient temperatures. Oil samples were removed from the oven after 1, 3, 5 and 7

179

days. For photooxidation under fluorescent lighting, samples were kept in a rectangular

180

polyethylene box (70 cm length × 35 cm width × 25 cm height) equipped with two 40 W cool

181

white fluorescent lights, which were suspended approximately 10 cm above the surface of the oil

182

containers.8 The fluorescent radiation was at a level of 2650 Lux, and the temperature inside the

183

container was 27±1 °C. Oil samples were removed from the light box after 1, 3, 6, 12, 24, 48,

184

and 72 h. The caps of sample containers were all wrapped with Parafilm, and kept at -80 °C for

185

oxidative stability tests within a month.

186

Conjugated dienes (CD) of the oil samples were determined according to the IUPAC

187

method.12 CD was calculated according to the equation below where A represents absorbance of

188

the solution at 234 nm, C is the concentration of the solution in g/100 mL, and d is the cell length

189

in 1 cm.

190 191

CD = A/(c × d)

192

9



193

Oil samples (0.05-0.20g) were analyzed for their contents of thiobarbituric acid reactive

194

substances (TBARS) according to the AOCS method.13 The intensity of the resultant colored

195

complex was measured at 532 nm using 8453A UV-Visible spectrophotometer (Agilent

196

Technologies, Palo Alto, CA, USA). The values of TBARS were reported using a standard line

197

prepared with 1,1,3,3-tetramethoxypropane as precursor of malondialdehyde (MDA).

Page 10 of 31

198 199

Statistical analysis and data interpretation. All the experiments were performed in triplicate.

200

One way ANOVA (analysis of variance) and Tukey’s standardized test were performed at a level

201

of p0.05) from each

334

other. The trend of TBARS formation during the photooxidation was not as clear as those for

335

primary oxidation products as indicated in their CD values. The Results also indicated that non-

336

stripped blackberry and blueberry seed oils had better stability than other oils.

337 338 339 340 341

ACKNOWLEDGEMENT One of us (FS) thanks the Natural Sciences and Engineering Research Council (NSERC) of Canada for financial support in the form of a discovery grant.

342 343 344

REFERENCES

16


Page 17 of 31


345

(1) Parry, J.; Su, L.; Luther, M.; Zhou, K.; Yurawecz, M. P.; Whittaker, P.; Yu, L. Fatty acid

346

composition and antioxidant properties of cold-pressed marionberry, boysenberry, red

347

raspberry, and blueberry seed oils. J. Agric. Food Chem. 2005, 53, 566-573.

348 349 350 351

(2) Shahidi, F.; Shukla, V. Nontriacylglycerol constituents of fats and oils. Inform 1996, 7, 12271232. (3) Traber, M. G.; Atkinson, J. Vitamin E, antioxidant and nothing more. Free Radical Biol. Med. 2007, 43, 4-15.

352

(4) Liu, M.; Wallin, R.; Wallmon, A.; Saldeen, T. Mixed tocopherols have a stronger inhibitory

353

effect on lipid peroxidation than alpha-tocopherol alone. J. Cardiovasc. Pharmacol. 2002, 39,

354

714-721.

355 356 357 358 359 360 361 362 363 364

(5) Alasalvar, C.; Wanasundara, U.; Zhong, Y.; Shahidi, F. Functional lipid characteristics of cherry laurel seeds (Laurocerasus officinalis Roem.). J. Food. Lipids 2006, 13, 223-234. (6) Parker, T. D.; Adams, D.; Zhou, K.; Harris, M.; Yu, L. Fatty acid composition and oxidative stability of Cold-pressed edible seed oils. J. Food Sci. 2003, 68, 1240-1243. (7) Fakourelis, N.; Lee, E. C.; Min, D. B. Effects of chlorophyll and β‐carotene on the oxidation stability of olive oil. J. Food Sci. 1987, 52, 234-235. (8) Abuzaytoun, R.; Shahidi, F. Oxidative stability of algal oils as affected by their minor components. J. Agric. Food Chem. 2006, 54, 8253-8260. (9) Wanasundara, U. N.; Shahidi, F. Positional distribution of fatty acids in triacylglycerols of seal blubber oil. J. Food Lipids 1997, 4, 51-64.

17



365

(10)

Lísa, M.; Holčapek, M. Triacylglycerols profiling in plant oils important in food industry,

366

dietetics and cosmetics using high-performance liquid chromatography–atmospheric pressure

367

chemical ionization mass spectrometry. J. Chromatogr. A 2008, 1198, 115-130.

368 369 370 371 372 373 374

(11)

Christie, W. W. Structural analysis of lipids by means of enzymatic hydrolysis. In Lipid

Analysis; Christie, W. W.; Ed.; Pergamon Press: New York, NY, 1982; pp.155–166. (12)

IUPAC, in Standard Methods and Recommended Practices of the American Oil

Chemists' Society, AOCS, Champaign, IL, 4th edn., 1987. (13)

AOCS, in Official Methods and Recommended Practices of the American Oil Chemists'

Society, AOCS, Champaign, IL, 4th edn., 1990. (14)

Parry, J.; Su, L.; Luther, M.; Zhou, K.; Yurawecz, M. P.; Whittaker, P.; Yu, L. Fatty acid

375

composition and antioxidant properties of cold-pressed marionberry, boysenberry, red

376

raspberry, and blueberry seed oils. J. Agric. Food Chem. 2005, 53, 566-573.

377

Page 18 of 31

(15)

Bushman, B. S.; Phillips, B.; Isbell, T.; Ou, B.; Crane, J. M.; Knapp, S. J. Chemical

378

composition of caneberry (rubus spp.) seeds and oils and their antioxidant potential. J. Agric.

379

Food Chem. 2004, 52, 7982-7987.

380

(16)

Van Hoed, V.; De Clercq, N.; Echim, C.; Andjelkovic, M.; Leber, E.; Dewettinck, K.;

381

Verhé, R. Berry seeds: A source of specialty oils with high content of bioactives and

382

nutritional value. J. Food Lipids 2009, 16, 33-49.

383

(17)

Aronson, W. J.; Glaspy, J. A.; Reddy, S. T.; Reese, D.; Heber, D.; Bagga, D. Modulation

384

of omega-3/omega-6 polyunsaturated ratios with dietary fish oils in men with prostate cancer.

385

Urology 2001, 58, 283-288.

18


Page 19 of 31

386 387 388


(18)

Cave Jr. W. T. Dietary n-3 (omega-3) polyunsaturated fatty acid effects on animal

tumorigenesis. FASEB J. 1991, 5, 2160-2166. (19)

Hu, F. B.; Bronner, L.; Willett, W. C.; Stampfer, M. J.; Rexrode, K. M.; Albert, C. M.;

389

Manson, J. E. Fish and omega-3 fatty acid intake and risk of coronary heart disease in

390

women. J. Am. Med. Assoc. 2002, 287, 1815-1821.

391

(20)

Narayanan, B. A.; Narayanan, N. K.; Reddy, B. S. Docosahexaenoic acid regulated genes

392

and transcription factors inducing apoptosis in human colon cancer cells. Int. J. Oncol. 2001,

393

19, 1255-1262.

394

(21)

Watkins, B. A.; Li, Y.; Allen, K. G.; Hoffmann, W. E.; Seifert, M. F. Dietary ratio of (n-

395

6)/(n-3) polyunsaturated fatty acids alters the fatty acid composition of bone compartments

396

and biomarkers of bone formation in rats. J. Nutr. 2000, 130, 2274-2284.

397

(22)

Neff, W.; Mounts, T.; Rinsch, W. Oxidative stability as affected by triacylglycerol

398

composition and structure of purified canola oil triacylglycerols from genetically modified

399

normal and high stearic and lauric acid canola varieties. LWT-Food Sci. Technol. 1997, 30,

400

793-799.

401 402 403

(23)

Neff, W.; Mounts, T.; Rinsch, W.; Konishi, H. Photooxidation of soybean oils as affected

by triacylglycerol composition and structure. J. Am. Oil Chem. Soc. 1993, 70, 163-168. (24)

Neff, W.; Mounts, T.; Rinsch, W.; Konishi, H.; El-Agaimy, M. Oxidative stability of

404

purified canola oil triacylglycerols with altered fatty acid compositions as affected by

405

triacylglycerol composition and structure. J. Am. Oil Chem. Soc. 1994, 71, 1101-1109.

19



406

(25)

Lakshminarayana, G.; Rao, T. C.; Ramalingaswamy, P. Varietal variations in content,

407

characteristics and composition of mango seeds and fat. J. Am. Oil Chem. Soc. 1983, 60, 88-

408

89.

409 410 411

(26)

Ali, M.; Gafur, M.; Rahman, M.; Ahmed, G. Variations in fat content and lipid class

composition in ten different mango varieties. J. Am. Oil Chem. Soc. 1985, 62, 520-523. (27)

Bakowska-Barczak, A. M.; Schieber, A.; Kolodziejczyk, P. Characterization of Canadian

412

black currant (ribes nigrum L.) seed oils and residues. J. Agric. Food Chem. 2009, 57, 11528-

413

11536.

414 415 416

(28)

Neff, W. E.; List, G. R.; Byrdwell, W. C. Effect of triacylglycerol composition on

functionality of margarine basestocks. LWT-Food Sci. Technol. 1999, 32, 416-424. (29)

Bakowska-Barczak, A. M.; Schieber, A.; Kolodziejczyk, P. Characterization of

417

Saskatoon berry (amelanchier alnifolia nutt.) seed oil. J. Agric. Food Chem. 2009, 57, 5401-

418

5406.

419 420

Page 20 of 31

(30)

Blekas, G.; Tsimidou, M.; Boskou, D. Contribution of α-tocopherol to olive oil stability.

Food Chem. 1995, 52, 289-294.

20


Page 21 of 31


Table 1. Fatty acid composition of the original blackberry, black raspberry, and blueberry seed oils and their stripped counterparts. FA(%) C16:0

BKSO 3.3±0.2

SBKSO 3.4±0.1

BRSO 2.0±0.0

SBRSO 1.9±0.0

BESO 5.2±0.2

SBESO 4.9±0.5

C18:0

1.6±0.3

1.7±0.2

0.6±0.0

0.6±0.0

1.3±0.0

1.2±0.4

C18:1

14.4±0.5 15.4±0.3

9.7±0.1

10.5±0.1 22.2±0.6 22.5±0.1

C18:2 n-6

63.4±1.3 63.6±0.5 53.4±0.0 54.7±0.2 41.9±0.4 43.0±0.7

C18:3 n-3

16.5±0.4 13.4±0.1 33.7±0.1 30.4±0.1 28.1±1.5 27.6±0.5

∑SFA

4.9

5.1

2.6

2.5

6.5

6.1

∑MUFA

14.4

15.4

9.7

10.5

22.2

22.5

∑PUFA

79.9

77

87.1

85.1

70

70.6

∑n-3

16.5

13.4

33.7

30.4

28.1

27.6

n-6/n-3

3.8

4.7

1.6

1.8

1.5

1.6

BKSO, blackberry seed oil; SBKSO, stripped blackberry seed oil; BRSO, black raspberry seed oil; SBRSO, stripped black raspberry seed oil; BESO, blueberry seed oil; SBESO, stripped blueberry seed oil; SFA, saturated fatty acids; MUFA, monounsaturated fatty acids; and PUFA, polyunsaturated fatty acids

21



Table 2. Triacylglycerol (TAG) composition (relative concentration percentage) of the original blackberry, black raspberry and blueberry seed oils. TAG (%)

BKSO

BRSO

BESO

LnLnLn

3.78±0.16b

13.25±0.15a

7.65±0.22c

LnLLn

12.90b±1.23b 24.29a±0.12a 17.96±0.44c

LLLn

20.16±2.47b

23.83±0.09a

16.81±0.41c

LnOLn

2.95±0.22c

4.98±0.02b

8.18±0.20a

LnLnP

0.97±0.21 b

0.60±0.01b

2.58±0.06a

LLL

20.16±2.17a

12.78±0.09b

6.27±0.15 c

OLLn

7.83±0.90 b

7.23±0.07b

13.24±0.33a

LnLP

2.69±0.23b

1.48±0.06b

4.51±0.11a

SLnLn

0.58±0.02 a

nd

0.90±0.02a

OLL

9.27±0.85a

4.31±0.11c

6.09±0.15b

OLnO

1.10±1.89b

nd

2.82±0.07a

LLP

3.65±0.54a

1.28±0.06c

2.37±0.06b

SLLn

2.11±0.28a

0.83c±0.03c

1.64±0.04 b

LnOP

n.d

nd

1.37±0.04

OLO

1.85±0.02b

0.66±0.04b

2.09±0.05a

SLL

2.64±0.18a

nd

2.10±0.06a

SOLn

n.d

0.42±0.06

n.d

OOO

0.10±0.21a

nd

0.10±0.01a

ALL

0.27±0.01

nd

n.d

22


Page 22 of 31

Page 23 of 31


SLO

0.54±0.32a

nd

0.45±0.0a

Total

95.92

95.92

97.13

nd, not detected; values in the same row with different superscripts are significantly different (p

Chemical Characteristics of Cold-Pressed ... - ACS Publications

Recommend Documents