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Effects of growing region and maturity stages on oil yield and fatty acid composition of coriander (Coriandrum sativum L.) fruit
Scientia Horticulturae 120 (2009) 525–531
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Effects of growing region and maturity stages on oil yield and fatty acid composition of coriander (Coriandrum sativum L.) fruit Kamel Msaada a,*, Karim Hosni a, Mouna Ben Taarit a, Mohamed Hammami b, Brahim Marzouk a a b
Aromatic and Medicinal Plants Unit, Biotechnology Center in Borj-Cedria Technopol, BP. 901, 2050 Hammam-Lif, Tunisia Laboratory of Biochemistry, UR 08-39, Faculty of Medicine, 5019 Monastir, Tunisia
A R T I C L E I N F O
A B S T R A C T
Article history: Received 7 September 2008 Received in revised form 21 November 2008 Accepted 25 November 2008
Changes on oil yield and fatty acid profiles were studied during maturation of coriander (Coriandrum sativum L.) fruits cultivated in Menzel Temime and Oued Beja, Tunisia. Oil and petroselinic acid biosynthesis proceeded at a steady rate up to 16 DAF in Oued Beja and in 33 DAF in Menzel Temime. The first results show that a rapid oil accumulation started at newly formed fruits and continued until their full maturity. During fruit maturation, fatty acid profiles varied significantly among the growing regions and stages of maturity. Petroselinic acid had the highest amount at the 16th and the 33th DAF, in Oued Beja and Menzel Temime, respectively. In Oued Beja, at full maturity, the main fatty acids were petroselinic acid (80.90 9.45%), followed by oleic (14.79 2.25%), palmitic (3.50 0.65%) and stearic (0.49 0.09%) acids. Fatty acid profile of fruits cultivated in Menzel Temime showed that in fully ripe fruit, petroselinic acid is the main compound (80.86 7.23%) followed by oleic (14.83 2.05%), palmitic (3.27 3.12%) and stearic (0.31 0.05%) acids. In both growing region, fruit development resulted mainly in an increase of petroselinic acid and a decrease of palmitic acid. Saturated and polyunsaturated fatty acids decreased significantly and monounsaturated fatty acids increased during maturation of fruit. Oil composition at the first four stages of maturity has a healthy and nutritionally value and the last stages were with important economic and industrial applications. Coriander fruit is potentially an important source of petroselinic which have numerous industrial applications. ß 2008 Elsevier B.V. All rights reserved.
Keywords: Coriander (Coriandrum sativum L.) Umbelliferae Fruit Fatty acids composition Maturation Growing region
1. Introduction The fatty acids profile is a main determinant of the oil quality in coriander fruit mainly with percentage of oleic, linoleic and petroselinic acids. However, oils with different fatty acid composition are required depending on their use in industry or for human consumption. Oils with a high proportion of oleic acid are more stable than others and contribute to reduction in cardiovascular diseases in humans (Jacocot, 1995). On the other hand, linoleic acid is an essential fatty acid for humans and it is preferred by industries when oil hydrogenation is required. Recently, the development of new crops for the production of industrial oils is an area of significant interest both scientifically and environmentally. While methods are being developed for modifying the fatty acid content and composition of oils produced by established crops such as oilseed rape and soya beans (Murphy, 1991), another approach is to investigate alternative species as
* Corresponding author. Tel.: +216 98682044; fax: +216 79412638. E-mail addresses: [email protected] (K. Msaada), [email protected] (K. Hosni), [email protected] (M. Ben Taarit), [email protected] (M. Hammami), [email protected] (B. Marzouk). 0304-4238/$ – see front matter ß 2008 Elsevier B.V. All rights reserved. doi:10.1016/j.scienta.2008.11.033
potential sources of specialist oils. An example of such a crop is the herb plant coriander (Coriandrum sativum L.), a member of the Umbelliferae family, whose fruits contain oils with a high concentration of the monounsaturated fatty acid, petroselinic acid. This acid can be oxidatively cleaved to produce a mixture of lauric acid, a compound useful in the production of detergents, and adipic acid, a C6 dicarboxylic acid which can be utilized in the synthesis of nylon polymer (Murphy, 1991). Physical, biochemical, and physiological changes which occur during fruit development imply that intracellular variations play an important role in the different distribution of metabolites in the cells (Izzo et al., 1995). For years food analysts and plant physiologists have been interested in the effects of maturation on the chemical components in the industrial parts of fruits because of their impact in the market quality of some industrial products made with petroselinic acid derivatives. Lipid components in fruits, though occurring in minor amounts, are presumed to contribute to the development of characteristic aromas and flavours during ripening as they are considered as precursors for various volatile odorous principles of fruits (Gholap and Bandyopadhyay, 1980). Supran (1978) reported that lipids contribute to the industrial and nutritional value as well as characteristic aromas and flavours.
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Recent studies on the compositional analysis of C. sativum L. fruits have described essential oil changes during maturation (Msaada et al., 2006, 2007a, 2008a), essential oil composition of different coriander parts (Msaada et al., 2003, 2007b) and fatty acid composition (Ramadan and Mo¨rsel, 2002, 2006; Msaada et al., 2008b). Unlike fruits of other species, changes in lipids and fatty acids with respect to growing region and maturity of C. salivum L. fruit are still very scarce reported. Changes on fatty acids profile during fruit maturation have been studied, to the best of our knowledge, only by Lakshminarayana et al. (1981); Msaada (2007) and Msaada et al. (2008b). The main objective of the work presented here was to determine the influence of maturity stages and growing region on oil content and fatty acid composition. The results will be important as an indication of the potential economic utility of Coriandrum sativum L. as a raw material source for useful industrial oils components. 2. Materials and methods 2.1. Plant material The same genotype of coriander fruits were planted in the same day (10 March in 2002) and randomly collected at different ripening stages from cultivated plants in Menzel Temime (NorthEastern Tunisia; latitude 36846’17.80’’(N); longitude 10846’03.38’’(E), altitude 141.43 m) and in Oued Be´ja (NorthWestern Tunisia; 36843’30.73’’(N); longitude 9811’30.60’’(E), altitude 215 m) during May and June 2002. Air temperatures in Oued Beja and Menzel Temime were obtained from the meteorological stations located respectively in Beja and Nabeul. Both growing regions were characterized by low annual rainfall of 700 mm and mean annual temperature of 16.8 8C. Harvest period was stretched from 5 days after flowering (DAF) to 22 and 41 DAF, in Oued Beja and Menzel Temime, respectively: time required for complete maturity. The fruit’s colour and relative moisture content were adopted as a ripening criterion (Table 1). Indeed, only full green fruits were harvested at the initial stages of maturity. Greenbrown fruits were considered as indicators of the intermediate stages. Only brown fruits were selected for analysis during the final stages of maturity. Each harvest was undertaken after a decrease of moisture content by 10% (Table 1). Moisture contents were determined by heating in an air-oven at 60 8C to constant weight.
2.2. Oil extraction Three samples of coriander fruits were finely ground in an electric grinder (IKA-WERK. Type: A: 10). Twenty grams of each ground material was extracted in a soxhlet-extractor with 100 ml hexane (Analytical Reagent, LabScan, Ltd., Dublin, Ireland) for 4 h. The extraction was protected from light. The extract was then filtered and after evaporation of the solvent under reduced pressure and temperature, the oil content was determined (Table 1). 2.3. Total lipid extraction and fatty acids methylation Triplicate sub-samples of 0.5 g were extracted using the modified method of Bligh and Dyer (1959). Thus, fruit samples were kept in boiling water for 10 min to inactivate lipase (Douce, 1964) and then ground manually using a mortar and pestle. A chloroform/methanol (Analytical Reagent, LabScan, Ltd., Dublin, Ireland) mixture (1:1 v/v) was used for total lipid extraction. After washing with water and centrifugation at 3000 g for 10 min, the organic layer containing total lipids was recovered and dried under a nitrogen stream. Total fatty acids (TFA) were methylated by using sodium methoxide solution (Sigma, Aldrich) according to the method of Cecchi et al. (1985). Methyl heptadecanoate (C17:0) was used as an internal standard. Those fatty acids methyl esters (FAMEs) obtained were subsequently analyzed. 2.4. Gas chromatography The fatty acid methyl esters were analyzed on a HP 6890 gas chromatograph (Agilent Palo Alto, CA, USA) equipped with a flame ionization detector (FID). The esters were separated on a RT-2560 capillary column (100 m length, 0.25 mm i.d, 0.20 mm film thickness). The oven temperature was kept at 170 8C for 2 min, followed by a 3 8C/min ramp to 240 8C and finally held there for an additional 15 min period. Nitrogen was used as carrier gas at a flow rate of 1.2 ml/min. The injector and detector temperature were maintained at 225 8C. A comparison of the retention times of the FAMEs with those of co-injected authentic standards (Analytical Reagent, LabScan, Ltd., Dublin, Ireland) was made to facilitate identification. 2.5. Statistical analysis All extractions and determinations were conducted in triplicate. Data is expressed as mean S.D. The means were
Table 1 Harvest dates, stages as days after flowering, fruit colour and state of maturity, relative moisture and oil contents of coriander fruit during maturation. Harvest no.
Harvest dates
DAF
Fruit colour, state of maturity
Relative moisture content (%, w/w)
Oil content (%, w/w)
Tempearature 8C (mean S.D.)
Oued Beja 1 2 3 4 5 6 7 8
04 06 08 10 12 15 17 21
June 2002 June2002 June 2002 June 2002 June 2002 June 2002 June 2002 June 2002
5 7 9 11 13 16 18 22
Unripe, fully green Unripe, fully green Unripe, fully green Unripe, green-brown Half ripe, green-brown Half ripe, green-brown Half ripe, green-brown Fully ripe, brown
90.50 0.60a 80.50 0.60b 70.50 0.60c 60.50 0.60d 50.50 0.60e 40.50 0.60f 30.50 1.70g 20.50 0.60h
2.70 0.20a 14.40 0.40b 15.40 0.70c 17.30 0.30d 22.60 0.70e 24.70 0.80f 25.60 0.60g 25.80 0.40g
26.23 3.45h 28.85 4.06fg 28.64 4.75f 29.78 5.02e 31.83 5.64d 32.75 4.98c 33.89 5.81b 34.43 5.64a
Menzel Temime 1 2 3 4 5 6 7
23 30 04 07 14 21 30
April 2002 April 2002 May 2002 May 2002 May 2002 May 2002 May 2002
5 12 16 19 26 33 41
Unripe, fully green Unripe, fully green Unripe, fully green Unripe, green-brown Half ripe, green-brown Half ripe, green-brown Fully ripe, brown
92.30 0.30a 82.30 2.20b 72.30 1.20c 62.30 2.60d 52.30 2.30e 42.30 1.10f 32.30 2.60g
3.30 0.30a 4.70 0.70b 10.30 0.60c 13.00 1.40d 24.10 0.60e 25.60 0.70f 25.90 1.00fg
21.53 2.36g 23.70 2.59f 24.62 3.12e 25.67 3.46cd 25.78 3.78c 26.45 4.11ab 26.87 4.23a
Values in the same row with different superscripts (a–h) are significantly different at P < 0.05.
K. Msaada et al. / Scientia Horticulturae 120 (2009) 525–531
compared by using the one-way and multivariate analysis of variance (ANOVA) followed by Duncan’s multiple range tests. The differences between individual means were deemed to be significant at P < 0.05. A principal component analysis (PCA) was performed in order to discriminate between different maturity stages on the basis of their fatty acids composition. Correlation coefficients were also calculated based on fatty acids composition during fruit maturation in Oued Beja and Menzel Temime regions. All analyses were performed by the ‘‘Statistica v 5.1’’ software (Statsoft, 1998).
Table 2 Effects of maturity stages [MS], growing region [R] and [MS] [R] interaction on fatty acid composition, oil and moisture contents. Variables
Factors
C16:0 (palmitic acid)
[MS] 22 [R] 3 [MS] [R] 14
C16:1n-7 (palmitoleic acid)
[MS] 22 [R] 3 [MS] [R] 14
114.54 162.69 174.73
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
9589.88 3184.19 2077.84
0.0000 0.0000 0.0000
***
C18:0 (stearic acid)
3. Results and discussion 3.1. Oil content The changes in oil content during coriander fruit maturation cultivated in Oued Beja and Menzel Temime are presented in Table 1. Significant changes (P < 0.05) were observed among the studied regions for oil content during fruit development and maturity. In Oued Beja fruits, oil content increase approximately by a factor of five from the 5th DAF; 2.70 0.20% to reach 14.40 0.40% at the 7th DAF representing the first phase of oil accumulation, the second phase started from 9th DAF (15.40 0.70%) to 16th DAF (24.70 0.80%) and the last phase of fruit maturation (from 18 to 22 DAF) was characterized by a relatively stationary rate of oil accumulation. At full maturity, oil content was maximal (25.80 0.40%). Concerning Menzel Temime fruits, there are also three episode of oil accumulation, but the differences were in the days after full blooming. However, the first episode began from 5 DAF (3.30 0.30%) to 16 DAF (10.30 0.60%), in the second phase, oil content increased significantly (P < 0.05) from 13.00 1.40% (19 DAF) to 24.10 0.60% (26 DAF). The final phase was marked by a slow accumulation of oil (25.60 0.70% at 33 DAF and 25.90 1.00% at 41 DAF). In both regions, oil accumulation follows three distinguished phases. Similar results were found by Msaada et al. (2008b) in Charfine area in 2005. Oil accumulation in coriander fruits may be regulated by the intervention of the enzymatic system ‘‘Fatty Acid Synthetase’’ (FASynthetase), which operates differently during fruit ripening. Thus, at the first and the second phase, the FA-Synthetase system was induced, and oil accumulation was accelerated. At the stationary phase, enzymes were inactive, probably by retro-inhibition, and the rate of oil accumulation was reduced. The obtained results suggested a regional effect on oil accumulation. However, oil content was moderately influenced by the maturity stages [MS] (P < 0.05), more affected by the growing region [R] (P < 0.01) and the highest effect (P < 0.001) was obtained by the [MS] [R] interaction (Table 2). In both regions and at full fruit ripeness, the oil content was maximal and its value was similar to others reports dealing with mature coriander fruit (Ramadan and Mo¨rsel, 2002; Msaada, 2007; Msaada et al., 2008b). The evolutionary trend in oil accumulation in coriander fruit was significantly different from those of other species notably Perilla frutescense of the lamiaceae family (Ichihara and Suda, 2003). According to the latter authors, very slow accumulation of lipids in P. frutescense seeds was observed during the first stages of maturity. While the maximal rate of lipid accumulation was obtained between 15 and 20 DAF. Stability in lipids accumulation was reported as the characteristic fact of the last phase of P. frutescense seeds maturation (from 20 to 31 DAF). Similar to P. frutescense seeds, a comparable trend in lipid accumulation have been observed in oilseed rape (Brassica napus) seeds. In this species, rapid accumulation of lipids was observed between 25 and 35 DAF while a weak lipid accumulation was seen during the first and the last stages of maturity (Vigeolas et al., 2003).
527
d.f. F-value
C18:1n-12 (petroselinic acid)
[MS] 22 [R] 3 [MS] [R] 14
C18:1n-9 (oleic acid)
[MS] 22 [R] 3 [MS] [R] 14
C18:2n-6 (linoleic acid)
C18:3n-6 (g-linolenic acid)
C20:0 (arachidic acid)
C18:3n-3 (a-linolenic acid)
C20:1n-9 (gadoleic acid)
0.377 0.720 0.550
P
Singification
0.9946 NS 0.5397 NS 0.8913 NS *** ***
*** ***
1.14 0.3169 NS 2.41 0.0703 NS 0.3115 0.5855 NS 60177.5 49162.7 116598.3
0.0000 0.0000 0.0000
*** *** ***
[MS] 22 [R] 3 [MS] [R] 14
2683.15 1354.48 2193.56
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
183.68 329.57 225.61
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
730.14 2590.64 2649.53
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
111.77 148.71 102.14
0.0000 0.0000 0.0000
***
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
8493.4 20051.7 18429.6
*** ***
*** ***
*** ***
*** ***
*** ***
[MS] 22 [R] 3 [MS] [R] 14
7.36 17.45 25.17
0.0000 0.0000 0.0000
***
C22:6n-3 (docosahexenoic [MS] 22 acid) [R] 3 [MS] [R] 14
1013.01 218.23 2809.29
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
22.61 1.68 291.08
0.0254 0.0011 0.0001
*
[MS] 22 [R] 3 [MS] [R] 14
3.77 605.31 4.39
0.0231 0.0042 0.0007
*
C22:1n-9 (erucic acid)
Oil content
Moisture content
*** ***
*** ***
** ***
** ***
*
P < 0.05. P < 0.01. *** P < 0.001. **
3.2. Fatty acids profile 3.2.1. Oued Beja region The first results showed that coriander fruit cultivated in Oued Beja matured in short period: 22 DAF (Table 3) compared to the Menzel Temime period: 41 DAF (Table 4) and in Charfine area, fruits matured in 55 DAF (Msaada et al., 2008b). There are considerable variations among the fatty acid profiles for the eight stages of maturity (Table 3). A total of 12 different fatty acids were identified in percentages of the TFA of the fruit oil, but not all stages of maturity had all fatty acids. In newly formed fruit (5 DAF), the MUFAs represent 76.49 6.75% of TFA with oleic and petroselinic acids contribution of 36.29 4.26% and 40.20 5.02%, respectively. During fruit development, these values reached 14,79 2.25% and 80.90 9.45%, respectively at the final stage of maturity followed
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Table 3 Variations in fatty acids composition (as a percent of TFA) of total lipids during coriander fruit maturation cultivated in Oued Beja. No.
Fatty acid
Days after flowering (DAF) 5
1 C16:0 (palmitic acid) 2 C16:1n-7 (palmitoleic acid) 3 C18:0 (stearic acid) 4 C18:1n-12 (petroselinic acid) 5 C18:1n-9 (oleic acid) 6 C18:2n-6 (linoleic acid) 7 C18:3n-6 (g-linolenic acid) 8 C20:0 (arachidic acid) 9 C18:3 n-3 (a-linolenic acid) 10 C20:1n-9 (gadoleic acid) 11 C22:1 n-9 (erucic acid) 12 C22:6 n-3 (docosahexenoic acid) Saturated fatty acids (SFA) Monounsaturated fatty acids (MUFA) Polyunsaturated fatty acids (PUFA) SFA/PUFA ratio
7 a
9 c
15.98 2.35 0.59 0.11f 40.20 5.02h 36.29 4.26a 16.86 3.24f 0.08 0.02e tr tr tr tr tr 16.57 3.42a 76.49 6.75f 16.94 2.75b 0.98 0.04c
5.87 0.38 0.06 0.01bc 1.54 0.58a 75.21 8.21f 0.13 0.04f 15.76 3.12b 0.29 0.07b 0.83 0.13a 0.20 0.03b 0.10 0.02b tr 8.24 1.45b 75.5 7.02g 16.25 3.00c 0.51 0.08d
11 b
6.06 0.96 0.20 0.03a 1.15 0.42b 68.54 7.52g 4.03 0.76d 16.86 3.85a 0.33 0.07a 0.29 0.07c 1.42 0.15a 0.16 0.07a 0.36 0.09a 0.61 0.10 a 7.5 1.75c 73.29 6.89h 18.61 4.15a 0.40 0.06e
13 e
3.90 0.52 0.14 0.02ab 0.75 0.09cd 80.31 9.75c 0.13 0.05f 14.06 2.94d 0.25 0.05cd 0.26 0.09c 0.20 0.04b tr tr tr 4.91 075e 80.58 8.65d 14.51 2.41e 0.34 0.07f
16 d
4.35 0.84 0.20 0.04a 0.80 0.12c 79.22 7.23e 0.23 0.08e 14.63 2.38c 0.22 0.04d 0.33 0.08b 0.02 0.00c 0.01 c tr tr 5.48 0.91d 79.66 6.73e 14.87 2.81d 0.37 0.06fg
18 f
22 g
3.60 0.68 0.19 0.03a 0.67 0.11e 81.26 9.56a 0.21 0.07e 13.63 2.12e 0.26 0.06bc 0.15 0.06d 0.02 0.00c tr tr tr 4.42 0.82ef 81.66 9.42c 13.65 2.21f 0.32 0.03h
3.16 0.48 0.22 0.05a 0.69 0.10de 79.99 7.26d 15.09 2.36b 0.52 0.09g 0.27 0.04bc 0.04 0.00e 0.02 0.00c tr tr 3.89 0.63eg 95.30 10.06b 0.81 0.08g 4.80 0.43b
3.50 0.65f 0.15 0.04ab 0.49 0.09g 80.90 9.45b 14.79 2.25c 0.04 0.01h 0.10 0.01e 0.03 0.00ef tr tr tr tr 4.02 0.79e 95.84 9.78a 0.14 0.05h 28.71 3.15a
Fatty acids percentages in the same line with different superscripts (a–h) are significantly different at P < 0.05. tr < 0.01%; (–): not detected.
by palmitic (3.50 0.65%), stearic (0.49 0.09%), palmitoleic (0.15 0.04%), g-linolenic (0.10 0.01%), linoleic (0.04 0.01%) and arachidic (0.03 0.00%) (Table 3). Petroselinic acid was the major fatty acid at all stages of maturity. The percentage of saturated fatty acids (SFA), mainly that of palmitic acid decreased significantly (P < 0.05) from 16.57 3.42% on the 5th DAF to 4.02 0.79% when fruit was fully ripened (Table 3). As for linoleic acid, its rate of accumulation was stable during 16 DAF and decreased drastically at full fruit ripeness to reach 0.04 0.01%. Quantitative fatty acids accumulation began from the 5th DAF; however, the most important variation was noted for petroselinic acid. At the stage 16 DAF, palmitoleic, gadoleic, erucic and docosahexaenoic acid were not detected and petroselinic reach a highest amount (81.26 9.56%). Lakshminarayana et al. (1981) also report that petroselinic acid was in maximum amount (79.8%) at 40 DAF before 10 DAF from full maturation. This is in agreement with results obtained later in Charfine area (Msaada et al., 2008b). The ratio of saturated fatty acids to unsaturated fatty acids (SFA/PUFA), increased significantly during fruit ripening. At full ripening, this ratio was 28.71 3.15 (Table 3). In mature fruits, opposite results were found in coriander (0.379) and niger (0.370) by Ramadan and Mo¨rsel (2006). Correlation coefficients between oil and moisture contents and individual fatty acids components in Oued Beja region were calculated. Oil content was negatively correlated with moisture
content (r = 0.94) and positively correlated with palmitoleic acid (r = 0.76), and both were significant at P < 0.01. Fruit maturation periods give opposite results for palmitic and petroselinic acids. As palmitic acid decreased, petroselinic acid increased as evidenced by a strong negative correlation coefficient (r = 0.98, P < 0.01). This is in agreement with the results obtained by Lakshminarayana et al. (1981) and Msaada et al. (2008b). The data, however, elucidate that palmitic acid is the precursor of petroselinic acid as reported by Cahoon et al. (1992). Principal component analysis (PCA) was carried out in order to determine the relationship between the different ripening stages on the basis of their fatty acids composition. A better discrimination was revealed on the two-dimensional visualization of the plotted scores, where the two PC accounted for 79.12% of total variance. As shown in Fig. 1, the first axis explained about 74.49% of the total variance and was positively correlated with all ripening stages. However, according to the second axis which explains 4.63% of the total variance, two principal clusters could be distinguished: one negatively correlated with this axis and contained the stages 18 and 22 DAF. The second cluster was positively correlated with the last axis and grouped the stages 7, 11, 13 and 16 DAF. Within this cluster, stages corresponding of 18 and 22 DAF formed the first cluster and 7, 11, 13 and 16 DAF formed the second one, suggesting
Table 4 Variations in fatty acids composition (as a percent of TFA) of total lipids during coriander fruit maturation cultivated in Menzel Temime. No.
Fatty acid
Days after flowering (DAF) 5
1 C16:0 (palmitic acid) 2 C16:1n-7 (palmitoleic acid) 3 C18:0 (stearic acid) 4 C18:1n-12 (petroselinic acid) 5 C18:1n-9 (oleic acid) 6 C18:2n-6 (linoleic acid) 7 C18:3n-6 (g-linolenic acid) 8 C20:0 (arachidic acid) 9 C18:3n-3 (a-linolenic acid) 10 C20:1n-9 (gadoleic acid) Saturated fatty acids (SFA) Monounsaturated fatty acids (MUFA) Polyunsaturated fatty acids (PUFA) SFA/PUFA ratio
12 b
11.31 1.64 – 1.16 0.12b 56.32 3.22f 16.66 2.94d 13.00 2.36a 0.31 0.08d 1.23 0.42a tr tr 13.7 2.56b 72.98 8.87g 13.31 2.32a 1.03 0.04g
16 a
14.30 1.85 0.34 0.11a 1.76 0.14a 46.27 3.86g 29.96 5.23a 0.39 0.08b 6.51 0.87a 0.21 0.08bc 0.07 0.01b 0.19 0.02b 16.27 3.21a 76.76 7.74f 6.97 1.02b 2.33 0.08f
19 c
10.19 1.25 0.19 0.09b 0.90 0.15c 58.96 4.01e 25.91 4.26b 0.06 0.01b 3.46 0.57b 0.05 0.01c 0.07 0.01b 0.22 0.04a 11.14 2.01c 85.28 6.97e 3.59 0.95c 3.10 0.63de
26 d
8.32 0.94 0.09 0.01c 0.74 0.21d 65.31 5.32d 22.59 3.01c 0.04 0.00b 0.11 0.01f 0.03 0.00c 2.74 0.81a 0.04 0.01c 9.09 1.78d 88.03 7.65d 2.89 0.85d 3.15 0.45d
Fatty acids percentages in the same line with different superscripts (a–g) are significantly different at P < 0.05. tr < 0.01%; (–): not detected.
33 e
3.76 0.45 0.09 0.01c 0.46 0.16e 80.24 6.25c 14.65 2.36f 0.11 0.01b 0.63 0.12c 0.04 0.01c 0.02 0.00d – 4.26 0.58e 94.98 8.99c 0.76 0.05e 5.61 1.58c
41 f
3.46 3.36 0.11 0.04c 0.40 0.08ef 81.44 6.38a 13.87 1.58g 0.19 0.02b 0.21 0.08e 0.23 0.05bc 0.09 0.01b – 4.09 0.56f 95.42 8.98b 0.49 0.04g 8.35 1.89a
3.27 3.12h 0.19 0.08b 0.31 0.05e 80.86 7.23b 14.83 2.05e 0.30 0.09b 0.21 0.09e 0.02 0.00c tr tr 3.6 0.24g 95.88 9.65a 0.51 0.06f 7.06 1.56b
K. Msaada et al. / Scientia Horticulturae 120 (2009) 525–531
Fig. 1. Principal component analysis scatter plot of the different ripening stages based on their fatty acids composition (Oued Beja).
similar composition both in quality and in quantity. It is worth mentioning that the fatty acids profiles at 16 and 22 DAF were closely comparable. As a consequence, it seems that a period of 16 DAF was sufficient to the morphological and physiological maturation of coriander fruits. At this stage of maturity, production of petroselinic acid is in maximum and could have numerous industrial applications. 3.2.2. Menzel Temime region Changes in fatty acids are of special importance to the quality of the oil. In the present study, fatty acid accumulation patterns resulting from fruit development duration were observed. The results presented in Table 4 showed that fatty acids composition changed significantly during fruit development. However, petroselinic acid is the main component at all stages of maturity and varied significantly (P < 0.05) among them. At full maturity, petroselinic (80.86 7.23%), oleic (14.83 2.05%), palmitic (3.27 3.12%), staric (0.31 0.05%), linoleic (0.30 0.09%), glinolenic (0.21 0.09%), palmitoleic (0.19 0.08%) and arachidic (0.02 0.00%) acids were the main compounds, other fatty acids (alinolenic and godoleic acids) were detected at a level less than 0.01% (Table 4), at this stage, the oil quality has an important industrial application. At the first stage of maturity (5 DAF), petroselinic acid (56.32 3.22%), oleic acid (16.66 2.94%), linoleic (13.00 2.36%), palmitic (11.31 1.64%), arachidic (1.23 0.42%), stearic (1.16 0.12%) and g-linolenic (0.31 0.08%) acids were the major fatty acids, a-linolenic and gadoleic acids were present in the oil in
Fig. 2. Principal component analysis scatter plot of the different ripening stages based on their fatty acids composition (Menzel Temime).
529
trace (<0.01%) like at the final stage of maturity, palmitoleic acid is not detected in the oil The ratio of saturated to polyunsaturated fatty acids (SFA/PUFA) increased significantly (P < 0.05) during fruit maturation from 0.98 0.04 at the initial stage of fruit maturity (5 DAF) to 7.06 1.56 at full fruit maturity. As shown in Fig. 2 the first axis explained a great proportion of the variation (67.61% of total variance) and was positively correlated with all ripening stages. On the basis of axis 2 which explains 1.85% of total variance, only one cluster was distinguished and formed by the last stages of fruit maturity (26, 33 and 41 DAF) suggesting a similar fatty acid composition both in quality and in quantity. The first stages (5, 12, 16 and 19 DAF) of maturity were clearly distinguished from this group. It is noticed that the fatty acid profiles at 26, 33 and 41 DAF have the same fatty acid composition (Fig. 2). A strong negative correlations between oil content and petroselinic acid (r = 0.96 P < 0.01) and between oil content and palmitic acid (r = 0.95 P < 0.01) were determined, the correlation coefficient obtained between petroselinic and palmitic acids was r = 0.96 indicating a reverted relationship between them. This is also in agreement with the results obtained by Lakshminarayana et al. (1981) and Msaada et al. (2008b). Linoleic and oleic acid are known as essential fatty acids and are precursors of omega-3 and omega-6 polyunsaturated fatty acids, and there are detected with considerable levels during the four first stages of maturity (5, 7, 9 and 11 DAF for Oued Beja and 5, 12, 16 and 19 for Menzel Temime) occurring to coriander fruit an important nutritional value. At the last stages of maturity, these fatty acids decreased, and petroselinc acid had the highest percentages and could have many applications in industry. In both Oued Beja and Menzel Temime regions and during fruit ripening SFA and PUFA decreased, whereas MUF increased significantly (P < 0.05). Jameison and Reid (1969) and Peiretti et al. (2004) also reported variations in the proportions of PUFA during the growth cycle of borage. Interest in the PUFA, as healthpromoting nutrients, has expanded dramatically in recent years. A rapidly growing literature illustrates the benefits of PUFA in alleviating cardiovascular, inflammatory, heart diseases, atherosclerosis, autoimmune disorder, diabetes and other diseases (Finley and Shahidi, 2001; Riemersma, 2001). The fatty acids composition and the high amounts of PUFA in the first stages of fruit ripening make the coriander lipids importance for a variety of healthy applications. Except for two values for petroselinic acid cited in the literature with a high value of 91% (Thies, 1993) and a rather low value of 52% (Guidotti et al., 2006), the level of petroselinic acid detected in this work is quite similar to that formerly found in high level, namely 81.26 9.56% and 81.44 6.38% in Oued Beja and Menzel Temime, respectively. In general, oil plants – except those genetically modified or breed strains – are able to accumulate more than 80% of one fatty acid due to oil crop biochemistry (Murphy, 1994). However, the fatty acid profile estimated in the present investigation was slightly different from the literature values that vary considerably. For example, in the present study, no lauric acid was found as reported by Subbaram and Young (1967) and no myristic acid (C14:0) was detected as mentioned by (Weber et al., 1997). Although g-linolenic acid (GLA) was identified in lower levels, a great deal of interest has been placed on the few oils that contain GLA, which is elongated to C20: 3n-6, dihomo-g-linolenic acid (DHGLA) (Lo´pez-Alonso and Garcı´a Maroto, 2000). Dihomo-gamma-linolenic acid is the precursor of the 1-series prostaglandins and undergoes further unsaturation leading to C20:4n-6, the precursor of the 2-series prostaglandins (O’Keefe, 1998). g-Linolenic acid has been recognized as essential for the human diet (WHO/FAO, 1977), while DHGLA has been found to possess anti-viral and anti-cancer inhibitors (Jareonkitmongkol et al.,
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1993). Dihomo-gamma-linolenic acid is present in fish oils as a result of bioaccumulation through the food chain (Lo´pez-Alonso and Garcı´aMaroto, 2000). Dihomo-gamma-linolenic acid is naturally synthesized only by some algae-like micro-organisms and some fungi, although a so-called D4-desaturase gene has been cloned from the coriander endosperm (Harwood, 1996). In the two studied regions, the level of petroselinic acid increase significantly during fruit maturation process, but in some points this level decrease, for example, in Oued Beja the decrease is between 7–9 DAF, 11–13 DAF and 16–18 DAF and in Menzel Temime this decrease was observed between 5–12 DAF and 33–41 DAF. This fact could be due to the variations in temperature (Table 1) affecting the enzymatic activity. Moreover, D4 palmitoylACP-desaturase, 3-ketoacyl-ACP synthase and petroselinoyl-ACPthiosterase involved in the biosynthesis of petroselinic acid were sensible to temperature fluctuations (Cahoon et al., 1992). From a biochemical standpoint, our results are consistent with Cheesebrough (1989) who showed that some of the enzymes involved in the fatty acid synthesis pathway are influenced by temperature fluctuations. Their study indicated that temperatures >35 8C nearly abolished oleoyl and linoleoyl desaturase activities, stearoyl-ACP desaturase activity decreased six-fold between 20 and 35 8C and palmitoyl-ACP elongation showed little change with respect to temperature variation. 3.3. Effects of growing region, stage of maturity and [R] [SM] on fatty acid profile The combined analysis of variance (Table 2) indicated that palmitoleic, stearic, oleic, linoleic, g-linolenic, arachidic, alinolenic, godoleic, erucic and docosahexenoic acids were highly (P < 0.001) affected by stage of maturity, the growing region and the stage of maturity growing region interaction. These factors were not significant for petroselinic and palmitic acid. Stability of the later fatty acids could be due the relationship existing between them in the metabolic pathway (Cahoon et al., 1992). These significant effects could be due to the difference in environmental factors between the two studied regions like mean daily temperature (Table 1), photoperiod, quality of soil, plant diseases, altitude above sea level.. However, studies conducted in controlled environments have shown that temperature (Wolf et al., 1982) and precipitation (Dornbos and Mullen, 1992) are environmental factors that have a major impact on soybean fatty acid levels in the seed. Moreover, factors such as planting date (Wilcox and Cavins, 1992; Schnebly and Fehr, 1993; Carrubba et al., 2006), cultural practices, soil type, or weed, disease or insect pressure also could affect fatty acid content but these factors were not investigated in this study. Acknowledgements This work is dedicated to the memory of Professor Bechir TRITAR (Faculte´ des Sciences Tunis) who passed away in June 1998. We are also grateful to personal in meteorological stations in Beja and Nabeul for given us mean daily temperature. References Bligh, E.G., Dyer, W.J., 1959. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37, 911–917. Cahoon, E.B., Shanklin, J., Ohlrogge, J.B., 1992. Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco. Proc. Nat. Acad. Sci. U.S.A. 89, 11184–11188. Carrubba, A., la Torre, R., Saiano, F., Alonzo, G., 2006. Effect of sowing time on coriander performance in a semiarid mediterranean environment. Crop Sci. 46, 437–447. Cecchi, G., Biasini, S., Castano, J., 1985. Me´thanolyse rapide des huiles en solvant. Note de laboratoire. Rev. Fr. Corps Gras. 4, 163–164.
Cheesebrough, T.M., 1989. Changes in the enzymes for fatty acid synthesis and desaturation during acclimation of developing soybean seeds to altered growth temperature. Plant Physiol. 90, 760–764. Dornbos, D.L., Mullen, R.E., 1992. Soybean seed protein and oil contents and fatty acid composition adjustments by drought and temperature. J. Am. Oil Chem. Soc. 69, 228–231. Douce, R., 1964. Identification et dosage de quelques glyce´rophospholipides dans les souches normales et tumorales de scorsome`res cultive´es in vitro. C. R. Acad. Sci. Paris 259, 3066–3068. Finley, J.W., Shahidi, F., 2001. The chemistry, processing and health benefits of highly unsaturated fatty acids: an overview. In: John, W.J., Shahidi, F. (Eds.), Omega-3 Fatty Acids, Chemistry, Nutrition and Health Effects. 1–13. American Chemical Society, Washington, pp. 258–279. Gholap, A.S., Bandyopadhyay, C., 1980. Fatty acid biogenesis in ripening mango (Magnifera indica L. var. ‘Alphonso’). J. Agric. Food Chem. 28, 839–841. Guidotti, M., Ravasio, N., Psaro, R., Gianotti, E., Coluccia, S., Marchese, L., 2006. Epoxidation of unsaturated FAMEs obtained from vegetable source over Ti (IV)grafted silica catalysts: a comparison between ordered and non-ordered mesoporous materials. J. Mol. Cat. A. Chem. 250, 218–225. Harwood, J.L., 1996. Recent advances in the biosynthesis of plant fatty acids. Biochem. Biophys. Acta 1301, 7–56. Ichihara, K., Suda, Y., 2003. Lipid biosynthesis in developing perilla seeds. Phytochemistry 63, 139–143. Izzo, R., Scartazza, A., Masia, A., Galleschi, L., Quartacci, M.F., Navari-Izzo, F., 1995. Lipid evolution during development and ripening of peach fruits. Phytochemistry 39, 1329–1334. Jacocot, B., 1995. El aceite de oliva: alimento medicinal. de aceites y grasas. Oleaginosos 19, 149–152. Jameison, G.R., Reid, E.H., 1969. The leaf lipids of some members of the Boraginaceae family. Phytochemistry 8, 1489–1492. Jareonkitmongkol, S., Sakuradani, E., Shimizu, S., 1993. A novel D5-desaturasedefective mutant of Mortierella alpina 1S–4 and its dihomo-g-linolenic acid productivity. Appl. Environ. Microbiol. 59, 300–304. Lakshminarayana, G., Rao, K.V.S.A., Devi, K.S., Kaimal, T.N.B., 1981. Changes in fatty acids during maturation of Coriandrum sativum seeds. J. Am. Oil Chem. Soc. 58, 838–839. Lo´pez-Alonso, D., Garcı´a-Maroto, F., 2000. Plants as ‘chemical factories’ for the production of polyunsaturated fatty acids. Biotechnol. Adv. 18, 481–497. Msaada, K., 2007. Evolution de la composition des huiles essentielles, des acides gras et des glyce´rolipides de Coriandrum sativum L. au cours de la maturation. Variation selon l’organe, la re´gion et la saison. The`se de Doctorat en Sciences Biologiques, Faculte´ des Sciences de Tunis, 219 pp. Msaada, K., Dhifi, W., Chahed, T., Marzouk, B., 2003. 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Msaada, K., Hosni, K., Ben Taarit, M., Ouchikh, O., Marzouk, B., 2008a. Variations in essential oil composition during maturation of coriander (Coriandrum sativum L.) fruits. J. Food Biochem., in press. Msaada, K., Hosni, K., Ben Taarit, M., Chahed, T., Hammami, M., Marzouk, B., 2008b. Changes in fatty acid composition of coriander (Coriandrum sativum L.) fruit during maturation. Ind. Crops Prod., in press. Murphy, D.J., Richards, D., Taylor, R., Capdevielle, J., Guillemot, J.C., Grison, R., Fairbairn, D., Bowra, S., 1994. Manipulation of seed oil content to produce industrial crops. In: Murphy, D.J. (Ed.), Second European Symposium on Industrial Crops and Products, vol. 3, Pisa, Italy, 22–23 November 1993, Designer Oil Crops, VCH, Weinheim, Ind. Crops Prod. (special issue) 17–27. Murphy, D.J., 1991. Designer oilseed crops: genetic engineering of new oilseed crops for edible and non-edible applications. Agro-Industry Hi-Tech. 2, 5–9. O’Keefe, S.F., 1998. Nomenclature and classification of lipids. In: Akoh, C.C., Min, D.B. (Eds.), Food lipids, chemistry nutrition and biotechnology. Marcel Dekker, New York, USA, pp. 8. Peiretti, P.G., Palmegiano, G.B., Salamano, G., 2004. Quality and fatty acid content of borage (Borago officinalis L.) during the growth cycle. Ital. J. Food Sci. 2, 177– 184. Ramadan, M.F., Mo¨rsel, J.T., 2002. Oil composition of coriander (Coriandrum sativum L.) fruit-seeds. Eur. Food Res. Technol. 215, 204–209. Ramadan, M.F., Mo¨rsel, J.T., 2006. Screening of the antiradical action of vegetable oils. J. Food Comp. Anal. 19, 838–842. Riemersma, R.A., 2001. The demise of the n-6 to n-3 fatty acid ratio? A dossier. Eur. J. Lip. Sci. Technol. 103, 372–373. Schnebly, S.R., Fehr, W.R., 1993. Effect of years and planting dates on fatty acid composition of soybean genotypes. Crop Sci. 33, 716–719. Statsoft, 1998. STATISTICA for Windows (Computer Program Electronic Manual). StatSoft Inc., Tulsa, OK.
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Contents lists available at ScienceDirect
Scientia Horticulturae journal homepage: www.elsevier.com/locate/scihorti
Effects of growing region and maturity stages on oil yield and fatty acid composition of coriander (Coriandrum sativum L.) fruit Kamel Msaada a,*, Karim Hosni a, Mouna Ben Taarit a, Mohamed Hammami b, Brahim Marzouk a a b
Aromatic and Medicinal Plants Unit, Biotechnology Center in Borj-Cedria Technopol, BP. 901, 2050 Hammam-Lif, Tunisia Laboratory of Biochemistry, UR 08-39, Faculty of Medicine, 5019 Monastir, Tunisia
A R T I C L E I N F O
A B S T R A C T
Article history: Received 7 September 2008 Received in revised form 21 November 2008 Accepted 25 November 2008
Changes on oil yield and fatty acid profiles were studied during maturation of coriander (Coriandrum sativum L.) fruits cultivated in Menzel Temime and Oued Beja, Tunisia. Oil and petroselinic acid biosynthesis proceeded at a steady rate up to 16 DAF in Oued Beja and in 33 DAF in Menzel Temime. The first results show that a rapid oil accumulation started at newly formed fruits and continued until their full maturity. During fruit maturation, fatty acid profiles varied significantly among the growing regions and stages of maturity. Petroselinic acid had the highest amount at the 16th and the 33th DAF, in Oued Beja and Menzel Temime, respectively. In Oued Beja, at full maturity, the main fatty acids were petroselinic acid (80.90 9.45%), followed by oleic (14.79 2.25%), palmitic (3.50 0.65%) and stearic (0.49 0.09%) acids. Fatty acid profile of fruits cultivated in Menzel Temime showed that in fully ripe fruit, petroselinic acid is the main compound (80.86 7.23%) followed by oleic (14.83 2.05%), palmitic (3.27 3.12%) and stearic (0.31 0.05%) acids. In both growing region, fruit development resulted mainly in an increase of petroselinic acid and a decrease of palmitic acid. Saturated and polyunsaturated fatty acids decreased significantly and monounsaturated fatty acids increased during maturation of fruit. Oil composition at the first four stages of maturity has a healthy and nutritionally value and the last stages were with important economic and industrial applications. Coriander fruit is potentially an important source of petroselinic which have numerous industrial applications. ß 2008 Elsevier B.V. All rights reserved.
Keywords: Coriander (Coriandrum sativum L.) Umbelliferae Fruit Fatty acids composition Maturation Growing region
1. Introduction The fatty acids profile is a main determinant of the oil quality in coriander fruit mainly with percentage of oleic, linoleic and petroselinic acids. However, oils with different fatty acid composition are required depending on their use in industry or for human consumption. Oils with a high proportion of oleic acid are more stable than others and contribute to reduction in cardiovascular diseases in humans (Jacocot, 1995). On the other hand, linoleic acid is an essential fatty acid for humans and it is preferred by industries when oil hydrogenation is required. Recently, the development of new crops for the production of industrial oils is an area of significant interest both scientifically and environmentally. While methods are being developed for modifying the fatty acid content and composition of oils produced by established crops such as oilseed rape and soya beans (Murphy, 1991), another approach is to investigate alternative species as
* Corresponding author. Tel.: +216 98682044; fax: +216 79412638. E-mail addresses: [email protected] (K. Msaada), [email protected] (K. Hosni), [email protected] (M. Ben Taarit), [email protected] (M. Hammami), [email protected] (B. Marzouk). 0304-4238/$ – see front matter ß 2008 Elsevier B.V. All rights reserved. doi:10.1016/j.scienta.2008.11.033
potential sources of specialist oils. An example of such a crop is the herb plant coriander (Coriandrum sativum L.), a member of the Umbelliferae family, whose fruits contain oils with a high concentration of the monounsaturated fatty acid, petroselinic acid. This acid can be oxidatively cleaved to produce a mixture of lauric acid, a compound useful in the production of detergents, and adipic acid, a C6 dicarboxylic acid which can be utilized in the synthesis of nylon polymer (Murphy, 1991). Physical, biochemical, and physiological changes which occur during fruit development imply that intracellular variations play an important role in the different distribution of metabolites in the cells (Izzo et al., 1995). For years food analysts and plant physiologists have been interested in the effects of maturation on the chemical components in the industrial parts of fruits because of their impact in the market quality of some industrial products made with petroselinic acid derivatives. Lipid components in fruits, though occurring in minor amounts, are presumed to contribute to the development of characteristic aromas and flavours during ripening as they are considered as precursors for various volatile odorous principles of fruits (Gholap and Bandyopadhyay, 1980). Supran (1978) reported that lipids contribute to the industrial and nutritional value as well as characteristic aromas and flavours.
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Recent studies on the compositional analysis of C. sativum L. fruits have described essential oil changes during maturation (Msaada et al., 2006, 2007a, 2008a), essential oil composition of different coriander parts (Msaada et al., 2003, 2007b) and fatty acid composition (Ramadan and Mo¨rsel, 2002, 2006; Msaada et al., 2008b). Unlike fruits of other species, changes in lipids and fatty acids with respect to growing region and maturity of C. salivum L. fruit are still very scarce reported. Changes on fatty acids profile during fruit maturation have been studied, to the best of our knowledge, only by Lakshminarayana et al. (1981); Msaada (2007) and Msaada et al. (2008b). The main objective of the work presented here was to determine the influence of maturity stages and growing region on oil content and fatty acid composition. The results will be important as an indication of the potential economic utility of Coriandrum sativum L. as a raw material source for useful industrial oils components. 2. Materials and methods 2.1. Plant material The same genotype of coriander fruits were planted in the same day (10 March in 2002) and randomly collected at different ripening stages from cultivated plants in Menzel Temime (NorthEastern Tunisia; latitude 36846’17.80’’(N); longitude 10846’03.38’’(E), altitude 141.43 m) and in Oued Be´ja (NorthWestern Tunisia; 36843’30.73’’(N); longitude 9811’30.60’’(E), altitude 215 m) during May and June 2002. Air temperatures in Oued Beja and Menzel Temime were obtained from the meteorological stations located respectively in Beja and Nabeul. Both growing regions were characterized by low annual rainfall of 700 mm and mean annual temperature of 16.8 8C. Harvest period was stretched from 5 days after flowering (DAF) to 22 and 41 DAF, in Oued Beja and Menzel Temime, respectively: time required for complete maturity. The fruit’s colour and relative moisture content were adopted as a ripening criterion (Table 1). Indeed, only full green fruits were harvested at the initial stages of maturity. Greenbrown fruits were considered as indicators of the intermediate stages. Only brown fruits were selected for analysis during the final stages of maturity. Each harvest was undertaken after a decrease of moisture content by 10% (Table 1). Moisture contents were determined by heating in an air-oven at 60 8C to constant weight.
2.2. Oil extraction Three samples of coriander fruits were finely ground in an electric grinder (IKA-WERK. Type: A: 10). Twenty grams of each ground material was extracted in a soxhlet-extractor with 100 ml hexane (Analytical Reagent, LabScan, Ltd., Dublin, Ireland) for 4 h. The extraction was protected from light. The extract was then filtered and after evaporation of the solvent under reduced pressure and temperature, the oil content was determined (Table 1). 2.3. Total lipid extraction and fatty acids methylation Triplicate sub-samples of 0.5 g were extracted using the modified method of Bligh and Dyer (1959). Thus, fruit samples were kept in boiling water for 10 min to inactivate lipase (Douce, 1964) and then ground manually using a mortar and pestle. A chloroform/methanol (Analytical Reagent, LabScan, Ltd., Dublin, Ireland) mixture (1:1 v/v) was used for total lipid extraction. After washing with water and centrifugation at 3000 g for 10 min, the organic layer containing total lipids was recovered and dried under a nitrogen stream. Total fatty acids (TFA) were methylated by using sodium methoxide solution (Sigma, Aldrich) according to the method of Cecchi et al. (1985). Methyl heptadecanoate (C17:0) was used as an internal standard. Those fatty acids methyl esters (FAMEs) obtained were subsequently analyzed. 2.4. Gas chromatography The fatty acid methyl esters were analyzed on a HP 6890 gas chromatograph (Agilent Palo Alto, CA, USA) equipped with a flame ionization detector (FID). The esters were separated on a RT-2560 capillary column (100 m length, 0.25 mm i.d, 0.20 mm film thickness). The oven temperature was kept at 170 8C for 2 min, followed by a 3 8C/min ramp to 240 8C and finally held there for an additional 15 min period. Nitrogen was used as carrier gas at a flow rate of 1.2 ml/min. The injector and detector temperature were maintained at 225 8C. A comparison of the retention times of the FAMEs with those of co-injected authentic standards (Analytical Reagent, LabScan, Ltd., Dublin, Ireland) was made to facilitate identification. 2.5. Statistical analysis All extractions and determinations were conducted in triplicate. Data is expressed as mean S.D. The means were
Table 1 Harvest dates, stages as days after flowering, fruit colour and state of maturity, relative moisture and oil contents of coriander fruit during maturation. Harvest no.
Harvest dates
DAF
Fruit colour, state of maturity
Relative moisture content (%, w/w)
Oil content (%, w/w)
Tempearature 8C (mean S.D.)
Oued Beja 1 2 3 4 5 6 7 8
04 06 08 10 12 15 17 21
June 2002 June2002 June 2002 June 2002 June 2002 June 2002 June 2002 June 2002
5 7 9 11 13 16 18 22
Unripe, fully green Unripe, fully green Unripe, fully green Unripe, green-brown Half ripe, green-brown Half ripe, green-brown Half ripe, green-brown Fully ripe, brown
90.50 0.60a 80.50 0.60b 70.50 0.60c 60.50 0.60d 50.50 0.60e 40.50 0.60f 30.50 1.70g 20.50 0.60h
2.70 0.20a 14.40 0.40b 15.40 0.70c 17.30 0.30d 22.60 0.70e 24.70 0.80f 25.60 0.60g 25.80 0.40g
26.23 3.45h 28.85 4.06fg 28.64 4.75f 29.78 5.02e 31.83 5.64d 32.75 4.98c 33.89 5.81b 34.43 5.64a
Menzel Temime 1 2 3 4 5 6 7
23 30 04 07 14 21 30
April 2002 April 2002 May 2002 May 2002 May 2002 May 2002 May 2002
5 12 16 19 26 33 41
Unripe, fully green Unripe, fully green Unripe, fully green Unripe, green-brown Half ripe, green-brown Half ripe, green-brown Fully ripe, brown
92.30 0.30a 82.30 2.20b 72.30 1.20c 62.30 2.60d 52.30 2.30e 42.30 1.10f 32.30 2.60g
3.30 0.30a 4.70 0.70b 10.30 0.60c 13.00 1.40d 24.10 0.60e 25.60 0.70f 25.90 1.00fg
21.53 2.36g 23.70 2.59f 24.62 3.12e 25.67 3.46cd 25.78 3.78c 26.45 4.11ab 26.87 4.23a
Values in the same row with different superscripts (a–h) are significantly different at P < 0.05.
K. Msaada et al. / Scientia Horticulturae 120 (2009) 525–531
compared by using the one-way and multivariate analysis of variance (ANOVA) followed by Duncan’s multiple range tests. The differences between individual means were deemed to be significant at P < 0.05. A principal component analysis (PCA) was performed in order to discriminate between different maturity stages on the basis of their fatty acids composition. Correlation coefficients were also calculated based on fatty acids composition during fruit maturation in Oued Beja and Menzel Temime regions. All analyses were performed by the ‘‘Statistica v 5.1’’ software (Statsoft, 1998).
Table 2 Effects of maturity stages [MS], growing region [R] and [MS] [R] interaction on fatty acid composition, oil and moisture contents. Variables
Factors
C16:0 (palmitic acid)
[MS] 22 [R] 3 [MS] [R] 14
C16:1n-7 (palmitoleic acid)
[MS] 22 [R] 3 [MS] [R] 14
114.54 162.69 174.73
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
9589.88 3184.19 2077.84
0.0000 0.0000 0.0000
***
C18:0 (stearic acid)
3. Results and discussion 3.1. Oil content The changes in oil content during coriander fruit maturation cultivated in Oued Beja and Menzel Temime are presented in Table 1. Significant changes (P < 0.05) were observed among the studied regions for oil content during fruit development and maturity. In Oued Beja fruits, oil content increase approximately by a factor of five from the 5th DAF; 2.70 0.20% to reach 14.40 0.40% at the 7th DAF representing the first phase of oil accumulation, the second phase started from 9th DAF (15.40 0.70%) to 16th DAF (24.70 0.80%) and the last phase of fruit maturation (from 18 to 22 DAF) was characterized by a relatively stationary rate of oil accumulation. At full maturity, oil content was maximal (25.80 0.40%). Concerning Menzel Temime fruits, there are also three episode of oil accumulation, but the differences were in the days after full blooming. However, the first episode began from 5 DAF (3.30 0.30%) to 16 DAF (10.30 0.60%), in the second phase, oil content increased significantly (P < 0.05) from 13.00 1.40% (19 DAF) to 24.10 0.60% (26 DAF). The final phase was marked by a slow accumulation of oil (25.60 0.70% at 33 DAF and 25.90 1.00% at 41 DAF). In both regions, oil accumulation follows three distinguished phases. Similar results were found by Msaada et al. (2008b) in Charfine area in 2005. Oil accumulation in coriander fruits may be regulated by the intervention of the enzymatic system ‘‘Fatty Acid Synthetase’’ (FASynthetase), which operates differently during fruit ripening. Thus, at the first and the second phase, the FA-Synthetase system was induced, and oil accumulation was accelerated. At the stationary phase, enzymes were inactive, probably by retro-inhibition, and the rate of oil accumulation was reduced. The obtained results suggested a regional effect on oil accumulation. However, oil content was moderately influenced by the maturity stages [MS] (P < 0.05), more affected by the growing region [R] (P < 0.01) and the highest effect (P < 0.001) was obtained by the [MS] [R] interaction (Table 2). In both regions and at full fruit ripeness, the oil content was maximal and its value was similar to others reports dealing with mature coriander fruit (Ramadan and Mo¨rsel, 2002; Msaada, 2007; Msaada et al., 2008b). The evolutionary trend in oil accumulation in coriander fruit was significantly different from those of other species notably Perilla frutescense of the lamiaceae family (Ichihara and Suda, 2003). According to the latter authors, very slow accumulation of lipids in P. frutescense seeds was observed during the first stages of maturity. While the maximal rate of lipid accumulation was obtained between 15 and 20 DAF. Stability in lipids accumulation was reported as the characteristic fact of the last phase of P. frutescense seeds maturation (from 20 to 31 DAF). Similar to P. frutescense seeds, a comparable trend in lipid accumulation have been observed in oilseed rape (Brassica napus) seeds. In this species, rapid accumulation of lipids was observed between 25 and 35 DAF while a weak lipid accumulation was seen during the first and the last stages of maturity (Vigeolas et al., 2003).
527
d.f. F-value
C18:1n-12 (petroselinic acid)
[MS] 22 [R] 3 [MS] [R] 14
C18:1n-9 (oleic acid)
[MS] 22 [R] 3 [MS] [R] 14
C18:2n-6 (linoleic acid)
C18:3n-6 (g-linolenic acid)
C20:0 (arachidic acid)
C18:3n-3 (a-linolenic acid)
C20:1n-9 (gadoleic acid)
0.377 0.720 0.550
P
Singification
0.9946 NS 0.5397 NS 0.8913 NS *** ***
*** ***
1.14 0.3169 NS 2.41 0.0703 NS 0.3115 0.5855 NS 60177.5 49162.7 116598.3
0.0000 0.0000 0.0000
*** *** ***
[MS] 22 [R] 3 [MS] [R] 14
2683.15 1354.48 2193.56
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
183.68 329.57 225.61
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
730.14 2590.64 2649.53
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
111.77 148.71 102.14
0.0000 0.0000 0.0000
***
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
8493.4 20051.7 18429.6
*** ***
*** ***
*** ***
*** ***
*** ***
[MS] 22 [R] 3 [MS] [R] 14
7.36 17.45 25.17
0.0000 0.0000 0.0000
***
C22:6n-3 (docosahexenoic [MS] 22 acid) [R] 3 [MS] [R] 14
1013.01 218.23 2809.29
0.0000 0.0000 0.0000
***
[MS] 22 [R] 3 [MS] [R] 14
22.61 1.68 291.08
0.0254 0.0011 0.0001
*
[MS] 22 [R] 3 [MS] [R] 14
3.77 605.31 4.39
0.0231 0.0042 0.0007
*
C22:1n-9 (erucic acid)
Oil content
Moisture content
*** ***
*** ***
** ***
** ***
*
P < 0.05. P < 0.01. *** P < 0.001. **
3.2. Fatty acids profile 3.2.1. Oued Beja region The first results showed that coriander fruit cultivated in Oued Beja matured in short period: 22 DAF (Table 3) compared to the Menzel Temime period: 41 DAF (Table 4) and in Charfine area, fruits matured in 55 DAF (Msaada et al., 2008b). There are considerable variations among the fatty acid profiles for the eight stages of maturity (Table 3). A total of 12 different fatty acids were identified in percentages of the TFA of the fruit oil, but not all stages of maturity had all fatty acids. In newly formed fruit (5 DAF), the MUFAs represent 76.49 6.75% of TFA with oleic and petroselinic acids contribution of 36.29 4.26% and 40.20 5.02%, respectively. During fruit development, these values reached 14,79 2.25% and 80.90 9.45%, respectively at the final stage of maturity followed
K. Msaada et al. / Scientia Horticulturae 120 (2009) 525–531
528
Table 3 Variations in fatty acids composition (as a percent of TFA) of total lipids during coriander fruit maturation cultivated in Oued Beja. No.
Fatty acid
Days after flowering (DAF) 5
1 C16:0 (palmitic acid) 2 C16:1n-7 (palmitoleic acid) 3 C18:0 (stearic acid) 4 C18:1n-12 (petroselinic acid) 5 C18:1n-9 (oleic acid) 6 C18:2n-6 (linoleic acid) 7 C18:3n-6 (g-linolenic acid) 8 C20:0 (arachidic acid) 9 C18:3 n-3 (a-linolenic acid) 10 C20:1n-9 (gadoleic acid) 11 C22:1 n-9 (erucic acid) 12 C22:6 n-3 (docosahexenoic acid) Saturated fatty acids (SFA) Monounsaturated fatty acids (MUFA) Polyunsaturated fatty acids (PUFA) SFA/PUFA ratio
7 a
9 c
15.98 2.35 0.59 0.11f 40.20 5.02h 36.29 4.26a 16.86 3.24f 0.08 0.02e tr tr tr tr tr 16.57 3.42a 76.49 6.75f 16.94 2.75b 0.98 0.04c
5.87 0.38 0.06 0.01bc 1.54 0.58a 75.21 8.21f 0.13 0.04f 15.76 3.12b 0.29 0.07b 0.83 0.13a 0.20 0.03b 0.10 0.02b tr 8.24 1.45b 75.5 7.02g 16.25 3.00c 0.51 0.08d
11 b
6.06 0.96 0.20 0.03a 1.15 0.42b 68.54 7.52g 4.03 0.76d 16.86 3.85a 0.33 0.07a 0.29 0.07c 1.42 0.15a 0.16 0.07a 0.36 0.09a 0.61 0.10 a 7.5 1.75c 73.29 6.89h 18.61 4.15a 0.40 0.06e
13 e
3.90 0.52 0.14 0.02ab 0.75 0.09cd 80.31 9.75c 0.13 0.05f 14.06 2.94d 0.25 0.05cd 0.26 0.09c 0.20 0.04b tr tr tr 4.91 075e 80.58 8.65d 14.51 2.41e 0.34 0.07f
16 d
4.35 0.84 0.20 0.04a 0.80 0.12c 79.22 7.23e 0.23 0.08e 14.63 2.38c 0.22 0.04d 0.33 0.08b 0.02 0.00c 0.01 c tr tr 5.48 0.91d 79.66 6.73e 14.87 2.81d 0.37 0.06fg
18 f
22 g
3.60 0.68 0.19 0.03a 0.67 0.11e 81.26 9.56a 0.21 0.07e 13.63 2.12e 0.26 0.06bc 0.15 0.06d 0.02 0.00c tr tr tr 4.42 0.82ef 81.66 9.42c 13.65 2.21f 0.32 0.03h
3.16 0.48 0.22 0.05a 0.69 0.10de 79.99 7.26d 15.09 2.36b 0.52 0.09g 0.27 0.04bc 0.04 0.00e 0.02 0.00c tr tr 3.89 0.63eg 95.30 10.06b 0.81 0.08g 4.80 0.43b
3.50 0.65f 0.15 0.04ab 0.49 0.09g 80.90 9.45b 14.79 2.25c 0.04 0.01h 0.10 0.01e 0.03 0.00ef tr tr tr tr 4.02 0.79e 95.84 9.78a 0.14 0.05h 28.71 3.15a
Fatty acids percentages in the same line with different superscripts (a–h) are significantly different at P < 0.05. tr < 0.01%; (–): not detected.
by palmitic (3.50 0.65%), stearic (0.49 0.09%), palmitoleic (0.15 0.04%), g-linolenic (0.10 0.01%), linoleic (0.04 0.01%) and arachidic (0.03 0.00%) (Table 3). Petroselinic acid was the major fatty acid at all stages of maturity. The percentage of saturated fatty acids (SFA), mainly that of palmitic acid decreased significantly (P < 0.05) from 16.57 3.42% on the 5th DAF to 4.02 0.79% when fruit was fully ripened (Table 3). As for linoleic acid, its rate of accumulation was stable during 16 DAF and decreased drastically at full fruit ripeness to reach 0.04 0.01%. Quantitative fatty acids accumulation began from the 5th DAF; however, the most important variation was noted for petroselinic acid. At the stage 16 DAF, palmitoleic, gadoleic, erucic and docosahexaenoic acid were not detected and petroselinic reach a highest amount (81.26 9.56%). Lakshminarayana et al. (1981) also report that petroselinic acid was in maximum amount (79.8%) at 40 DAF before 10 DAF from full maturation. This is in agreement with results obtained later in Charfine area (Msaada et al., 2008b). The ratio of saturated fatty acids to unsaturated fatty acids (SFA/PUFA), increased significantly during fruit ripening. At full ripening, this ratio was 28.71 3.15 (Table 3). In mature fruits, opposite results were found in coriander (0.379) and niger (0.370) by Ramadan and Mo¨rsel (2006). Correlation coefficients between oil and moisture contents and individual fatty acids components in Oued Beja region were calculated. Oil content was negatively correlated with moisture
content (r = 0.94) and positively correlated with palmitoleic acid (r = 0.76), and both were significant at P < 0.01. Fruit maturation periods give opposite results for palmitic and petroselinic acids. As palmitic acid decreased, petroselinic acid increased as evidenced by a strong negative correlation coefficient (r = 0.98, P < 0.01). This is in agreement with the results obtained by Lakshminarayana et al. (1981) and Msaada et al. (2008b). The data, however, elucidate that palmitic acid is the precursor of petroselinic acid as reported by Cahoon et al. (1992). Principal component analysis (PCA) was carried out in order to determine the relationship between the different ripening stages on the basis of their fatty acids composition. A better discrimination was revealed on the two-dimensional visualization of the plotted scores, where the two PC accounted for 79.12% of total variance. As shown in Fig. 1, the first axis explained about 74.49% of the total variance and was positively correlated with all ripening stages. However, according to the second axis which explains 4.63% of the total variance, two principal clusters could be distinguished: one negatively correlated with this axis and contained the stages 18 and 22 DAF. The second cluster was positively correlated with the last axis and grouped the stages 7, 11, 13 and 16 DAF. Within this cluster, stages corresponding of 18 and 22 DAF formed the first cluster and 7, 11, 13 and 16 DAF formed the second one, suggesting
Table 4 Variations in fatty acids composition (as a percent of TFA) of total lipids during coriander fruit maturation cultivated in Menzel Temime. No.
Fatty acid
Days after flowering (DAF) 5
1 C16:0 (palmitic acid) 2 C16:1n-7 (palmitoleic acid) 3 C18:0 (stearic acid) 4 C18:1n-12 (petroselinic acid) 5 C18:1n-9 (oleic acid) 6 C18:2n-6 (linoleic acid) 7 C18:3n-6 (g-linolenic acid) 8 C20:0 (arachidic acid) 9 C18:3n-3 (a-linolenic acid) 10 C20:1n-9 (gadoleic acid) Saturated fatty acids (SFA) Monounsaturated fatty acids (MUFA) Polyunsaturated fatty acids (PUFA) SFA/PUFA ratio
12 b
11.31 1.64 – 1.16 0.12b 56.32 3.22f 16.66 2.94d 13.00 2.36a 0.31 0.08d 1.23 0.42a tr tr 13.7 2.56b 72.98 8.87g 13.31 2.32a 1.03 0.04g
16 a
14.30 1.85 0.34 0.11a 1.76 0.14a 46.27 3.86g 29.96 5.23a 0.39 0.08b 6.51 0.87a 0.21 0.08bc 0.07 0.01b 0.19 0.02b 16.27 3.21a 76.76 7.74f 6.97 1.02b 2.33 0.08f
19 c
10.19 1.25 0.19 0.09b 0.90 0.15c 58.96 4.01e 25.91 4.26b 0.06 0.01b 3.46 0.57b 0.05 0.01c 0.07 0.01b 0.22 0.04a 11.14 2.01c 85.28 6.97e 3.59 0.95c 3.10 0.63de
26 d
8.32 0.94 0.09 0.01c 0.74 0.21d 65.31 5.32d 22.59 3.01c 0.04 0.00b 0.11 0.01f 0.03 0.00c 2.74 0.81a 0.04 0.01c 9.09 1.78d 88.03 7.65d 2.89 0.85d 3.15 0.45d
Fatty acids percentages in the same line with different superscripts (a–g) are significantly different at P < 0.05. tr < 0.01%; (–): not detected.
33 e
3.76 0.45 0.09 0.01c 0.46 0.16e 80.24 6.25c 14.65 2.36f 0.11 0.01b 0.63 0.12c 0.04 0.01c 0.02 0.00d – 4.26 0.58e 94.98 8.99c 0.76 0.05e 5.61 1.58c
41 f
3.46 3.36 0.11 0.04c 0.40 0.08ef 81.44 6.38a 13.87 1.58g 0.19 0.02b 0.21 0.08e 0.23 0.05bc 0.09 0.01b – 4.09 0.56f 95.42 8.98b 0.49 0.04g 8.35 1.89a
3.27 3.12h 0.19 0.08b 0.31 0.05e 80.86 7.23b 14.83 2.05e 0.30 0.09b 0.21 0.09e 0.02 0.00c tr tr 3.6 0.24g 95.88 9.65a 0.51 0.06f 7.06 1.56b
K. Msaada et al. / Scientia Horticulturae 120 (2009) 525–531
Fig. 1. Principal component analysis scatter plot of the different ripening stages based on their fatty acids composition (Oued Beja).
similar composition both in quality and in quantity. It is worth mentioning that the fatty acids profiles at 16 and 22 DAF were closely comparable. As a consequence, it seems that a period of 16 DAF was sufficient to the morphological and physiological maturation of coriander fruits. At this stage of maturity, production of petroselinic acid is in maximum and could have numerous industrial applications. 3.2.2. Menzel Temime region Changes in fatty acids are of special importance to the quality of the oil. In the present study, fatty acid accumulation patterns resulting from fruit development duration were observed. The results presented in Table 4 showed that fatty acids composition changed significantly during fruit development. However, petroselinic acid is the main component at all stages of maturity and varied significantly (P < 0.05) among them. At full maturity, petroselinic (80.86 7.23%), oleic (14.83 2.05%), palmitic (3.27 3.12%), staric (0.31 0.05%), linoleic (0.30 0.09%), glinolenic (0.21 0.09%), palmitoleic (0.19 0.08%) and arachidic (0.02 0.00%) acids were the main compounds, other fatty acids (alinolenic and godoleic acids) were detected at a level less than 0.01% (Table 4), at this stage, the oil quality has an important industrial application. At the first stage of maturity (5 DAF), petroselinic acid (56.32 3.22%), oleic acid (16.66 2.94%), linoleic (13.00 2.36%), palmitic (11.31 1.64%), arachidic (1.23 0.42%), stearic (1.16 0.12%) and g-linolenic (0.31 0.08%) acids were the major fatty acids, a-linolenic and gadoleic acids were present in the oil in
Fig. 2. Principal component analysis scatter plot of the different ripening stages based on their fatty acids composition (Menzel Temime).
529
trace (<0.01%) like at the final stage of maturity, palmitoleic acid is not detected in the oil The ratio of saturated to polyunsaturated fatty acids (SFA/PUFA) increased significantly (P < 0.05) during fruit maturation from 0.98 0.04 at the initial stage of fruit maturity (5 DAF) to 7.06 1.56 at full fruit maturity. As shown in Fig. 2 the first axis explained a great proportion of the variation (67.61% of total variance) and was positively correlated with all ripening stages. On the basis of axis 2 which explains 1.85% of total variance, only one cluster was distinguished and formed by the last stages of fruit maturity (26, 33 and 41 DAF) suggesting a similar fatty acid composition both in quality and in quantity. The first stages (5, 12, 16 and 19 DAF) of maturity were clearly distinguished from this group. It is noticed that the fatty acid profiles at 26, 33 and 41 DAF have the same fatty acid composition (Fig. 2). A strong negative correlations between oil content and petroselinic acid (r = 0.96 P < 0.01) and between oil content and palmitic acid (r = 0.95 P < 0.01) were determined, the correlation coefficient obtained between petroselinic and palmitic acids was r = 0.96 indicating a reverted relationship between them. This is also in agreement with the results obtained by Lakshminarayana et al. (1981) and Msaada et al. (2008b). Linoleic and oleic acid are known as essential fatty acids and are precursors of omega-3 and omega-6 polyunsaturated fatty acids, and there are detected with considerable levels during the four first stages of maturity (5, 7, 9 and 11 DAF for Oued Beja and 5, 12, 16 and 19 for Menzel Temime) occurring to coriander fruit an important nutritional value. At the last stages of maturity, these fatty acids decreased, and petroselinc acid had the highest percentages and could have many applications in industry. In both Oued Beja and Menzel Temime regions and during fruit ripening SFA and PUFA decreased, whereas MUF increased significantly (P < 0.05). Jameison and Reid (1969) and Peiretti et al. (2004) also reported variations in the proportions of PUFA during the growth cycle of borage. Interest in the PUFA, as healthpromoting nutrients, has expanded dramatically in recent years. A rapidly growing literature illustrates the benefits of PUFA in alleviating cardiovascular, inflammatory, heart diseases, atherosclerosis, autoimmune disorder, diabetes and other diseases (Finley and Shahidi, 2001; Riemersma, 2001). The fatty acids composition and the high amounts of PUFA in the first stages of fruit ripening make the coriander lipids importance for a variety of healthy applications. Except for two values for petroselinic acid cited in the literature with a high value of 91% (Thies, 1993) and a rather low value of 52% (Guidotti et al., 2006), the level of petroselinic acid detected in this work is quite similar to that formerly found in high level, namely 81.26 9.56% and 81.44 6.38% in Oued Beja and Menzel Temime, respectively. In general, oil plants – except those genetically modified or breed strains – are able to accumulate more than 80% of one fatty acid due to oil crop biochemistry (Murphy, 1994). However, the fatty acid profile estimated in the present investigation was slightly different from the literature values that vary considerably. For example, in the present study, no lauric acid was found as reported by Subbaram and Young (1967) and no myristic acid (C14:0) was detected as mentioned by (Weber et al., 1997). Although g-linolenic acid (GLA) was identified in lower levels, a great deal of interest has been placed on the few oils that contain GLA, which is elongated to C20: 3n-6, dihomo-g-linolenic acid (DHGLA) (Lo´pez-Alonso and Garcı´a Maroto, 2000). Dihomo-gamma-linolenic acid is the precursor of the 1-series prostaglandins and undergoes further unsaturation leading to C20:4n-6, the precursor of the 2-series prostaglandins (O’Keefe, 1998). g-Linolenic acid has been recognized as essential for the human diet (WHO/FAO, 1977), while DHGLA has been found to possess anti-viral and anti-cancer inhibitors (Jareonkitmongkol et al.,
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1993). Dihomo-gamma-linolenic acid is present in fish oils as a result of bioaccumulation through the food chain (Lo´pez-Alonso and Garcı´aMaroto, 2000). Dihomo-gamma-linolenic acid is naturally synthesized only by some algae-like micro-organisms and some fungi, although a so-called D4-desaturase gene has been cloned from the coriander endosperm (Harwood, 1996). In the two studied regions, the level of petroselinic acid increase significantly during fruit maturation process, but in some points this level decrease, for example, in Oued Beja the decrease is between 7–9 DAF, 11–13 DAF and 16–18 DAF and in Menzel Temime this decrease was observed between 5–12 DAF and 33–41 DAF. This fact could be due to the variations in temperature (Table 1) affecting the enzymatic activity. Moreover, D4 palmitoylACP-desaturase, 3-ketoacyl-ACP synthase and petroselinoyl-ACPthiosterase involved in the biosynthesis of petroselinic acid were sensible to temperature fluctuations (Cahoon et al., 1992). From a biochemical standpoint, our results are consistent with Cheesebrough (1989) who showed that some of the enzymes involved in the fatty acid synthesis pathway are influenced by temperature fluctuations. Their study indicated that temperatures >35 8C nearly abolished oleoyl and linoleoyl desaturase activities, stearoyl-ACP desaturase activity decreased six-fold between 20 and 35 8C and palmitoyl-ACP elongation showed little change with respect to temperature variation. 3.3. Effects of growing region, stage of maturity and [R] [SM] on fatty acid profile The combined analysis of variance (Table 2) indicated that palmitoleic, stearic, oleic, linoleic, g-linolenic, arachidic, alinolenic, godoleic, erucic and docosahexenoic acids were highly (P < 0.001) affected by stage of maturity, the growing region and the stage of maturity growing region interaction. These factors were not significant for petroselinic and palmitic acid. Stability of the later fatty acids could be due the relationship existing between them in the metabolic pathway (Cahoon et al., 1992). These significant effects could be due to the difference in environmental factors between the two studied regions like mean daily temperature (Table 1), photoperiod, quality of soil, plant diseases, altitude above sea level.. However, studies conducted in controlled environments have shown that temperature (Wolf et al., 1982) and precipitation (Dornbos and Mullen, 1992) are environmental factors that have a major impact on soybean fatty acid levels in the seed. Moreover, factors such as planting date (Wilcox and Cavins, 1992; Schnebly and Fehr, 1993; Carrubba et al., 2006), cultural practices, soil type, or weed, disease or insect pressure also could affect fatty acid content but these factors were not investigated in this study. Acknowledgements This work is dedicated to the memory of Professor Bechir TRITAR (Faculte´ des Sciences Tunis) who passed away in June 1998. We are also grateful to personal in meteorological stations in Beja and Nabeul for given us mean daily temperature. References Bligh, E.G., Dyer, W.J., 1959. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37, 911–917. Cahoon, E.B., Shanklin, J., Ohlrogge, J.B., 1992. Expression of a coriander desaturase results in petroselinic acid production in transgenic tobacco. Proc. Nat. Acad. Sci. U.S.A. 89, 11184–11188. Carrubba, A., la Torre, R., Saiano, F., Alonzo, G., 2006. Effect of sowing time on coriander performance in a semiarid mediterranean environment. Crop Sci. 46, 437–447. Cecchi, G., Biasini, S., Castano, J., 1985. Me´thanolyse rapide des huiles en solvant. Note de laboratoire. Rev. Fr. Corps Gras. 4, 163–164.
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