Industrial Crops and Products 36 (2012) 304307

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Industrial Crops and Products

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Tocochromanol content and composition in Jatropha curcas seeds

Pablo A. Corzo-Valladares a , Jos M. Fernndez-Martnez b , Leonardo Velasco b,
a
Bionor Transformacin S.A., AIC-Automotive Intelligence Center, Parque Empresarial Boroa, Parcela 2A-4, 48340 Amorebieta, Bizkaia, Spain
b
Instituto de Agricultura Sostenible (IAS-CSIC), Alameda del Obispo s/n, 14004 Crdoba, Spain

a r t i c l e i n f o a b s t r a c t

Article history: Physic nut (Jatropha curcas L.) is a promising seed oil source for biodiesel production. Natural antioxi-
Received 29 April 2011 dants play a major role in maintaining oxidative stability of oils and they also have important food and
Received in revised form 11 October 2011 industrial applications. Among them, tocochromanols are the most abundant in seeds. The objective
Accepted 14 October 2011
of this research was to evaluate the variation for tocochromanol content and prole in a germplasm
Available online 26 November 2011
collection of 52 accessions of J. curcas. Seeds collected in two different periods, August and November
of 2009, were analysed for tocochromanol content. Additionally, the dynamics of tocochromanol accu-
Keywords:
mulation in developing seeds was studied. Total seed tocochromanol content averaged 307.2 mg kg1 in
Germplasm
Jatropha curcas
August and 303.7 mg kg1 in November, whereas total oil tocochromanol content averaged 507.4 mg kg1
Seed development in August and 500.8 mg kg1 in November. The tocochromanol fraction was made up of 15.4% gamma-
Tocochromanols tocopherol, 83.8% gamma-tocotrienol, and 0.8% delta-tocotrienol in August and 18.0% gamma-tocopherol,
Tocopherols 80.4% gamma-tocotrienol, and 1.6% delta-tocotrienol in November. Genotype environment effects were
Tocotrienols identied for tocochromanol content but not for the proportion of major tocochromanol homologues,
which showed a high positive correlation between both environments. Developing seeds contained pri-
marily alpha-tocopherol and gamma-tocopherol at early stages of development, with gamma-tocotrienol
and delta-tocotrienol being practically undetectable. Gamma-tocotrienol content remained practically
undetectable till 66 DAP and then increased pronouncedly to nal levels of 177.1 mg kg1 (74.8% of the
total tocochromanol content). The powerful antioxidant and health-promoting properties of gamma-
tocotrienol encourages further studies on selection for the tocopherol/tocotrienol ratio in Jatropha and on
the potential of tocochromanols as high added-value products derived from Jatropha seed oil production.

2011 Elsevier B.V. All rights reserved.

1. Introduction
Presently, more than 95% of biodiesel is obtained from edible
oils, mainly rapeseed/canola (Brassica napus L.) (Gui et al., 2008).
The use of edible oils for biodiesel productions has been associ-
ated with imbalance of the food markets. For example, the rapid
expansion of EU and US vegetable oil consumption as a feedstock
for biodiesel production played a major role in raising soybean oil
prices, which doubled from 2001 to 2007 (Durrett et al., 2008).
Additionally, it has been claimed that incentives for biodiesel pro-
duction are promoting deforestation in Southeast Asia and the
Amazon by driving up crop prices (Gui et al., 2008). These prob-
lems can be partly overcome by promoting biodiesel production
from non-edible oil sources. Among them, the perennial crop physic
nut (Jatropha curcas L.) is a promising alternative because it is well
adapted to marginal areas with poor soils and low rainfall not well
suited to annual crops (Heller, 1996).
Corresponding author. Tel.: +34 957 499236; fax: +34 957 499252.
E-mail address: lvelasco@ias.csic.es (L. Velasco).
Jatropha seeds have typical oil content between 35.6% and 42.3%
(Heller, 1996) with a fatty acid prole made up of palmitic acid
(10.513.0%), stearic acid (2.32.8%), oleic acid (41.548.8%), and
linoleic acid (34.644.4%) (Martnez-Herrera et al., 2006). The oil
can be easily converted into biodiesel that meets American and
European standards (Achten et al., 2007).
Tocopherols and tocotrienols, collectively known as tocochro-
manols, are minor plant compounds that exhibit vitamin E activity.
They have a molecular structure comprising a chromanol ring with
a given number of methyl substituents and a phytyl side chain,
which is saturated in tocopherols and unsaturated in tocotrienols.
They occur in nature in four forms known as alpha, beta, gamma,
and delta, which differ in the number and position of methyl
substituents (Hunter and Cahoon, 2007). Tocopherols are mainly
present in oil seeds, nuts and cereal grains, leaves, and other green
parts of higher plants (Kamal-Eldin and Appelqvist, 1996). How-
ever, little is known about the distribution of tocotrienols in plants.
They are not found in the green parts of the plants but, rather, in
the seeds of some monocotyledonous and dicotyledonous plants
(Kamal-Eldin and Appelqvist, 1996; Horvath et al., 2006a), palm
oil (Edem, 2002) and specialized cells like latex tubers (Horvath

0926-6690/$ see front matter 2011 Elsevier B.V. All rights reserved.
doi:10.1016/j.indcrop.2011.10.018
 P.A. Corzo-Valladares et al. / Industrial Crops and Products 36 (2012) 304307
et al., 2006a). Information on the tocochromanol content and pro-
le of J. curcas seeds is scarce. Djenontin et al. (2006) reported a
total tocochromanol content of 199.0 mg kg1 in seeds collected
in Benin, with the tocochromanol prole made up of 10.2% alpha-
tocopherol, 12.9% beta-tocopherol, and 76.9% gamma-tocopherol.
The objective of this research was to evaluate variation for
tocochromanol content and prole in a germoplasm collection of J.
curcas.
2. Experimental
2.1. Plant materials
The study was conducted in 2009 on a germplasm collection of J.
curcas located in the experimental elds of the Estacin Experimen-
tal La Mayora (CSIC), Algarrobo-Costa, Mlaga, Spain (36 45 10 N;
4 02 36 W; Elev. 29 m). The collection was planted in 2007 and
consists of 61 accessions, though only 52 accessions were used
for the present research, as the rest of accessions did not produce
seeds. The accessions were arranged in single rows 12-m long with
a distance of 1 m between plants in the row and a row spacing of
2 m. The accessions used in the study came from Mexico (n = 4),
Guatemala (n = 26), El Salvador (n = 1), Ecuador (n = 1), Brazil (n = 2),
Peru (n = 7), Cape Verde (n = 3), Guinea Bissau (n = 1), Madagascar
(n = 1), India (n = 4), China (n = 1), and Philippines (n = 1). The plants
were periodically fertirrigated during the summer months.
2.2. Sampling
Even though the accessions showed variation for their life cycle
in the conditions of the plot, in general the plants lost their leaves
at the beginning of the winter (DecemberJanuary) and resumed
growth at the beginning of the spring (May). Flowering started
between 30 and 45 days after the beginning of the vegetative
growth, and continued till middle fall (OctoberNovember). Flow-
ering peaks for most of the accessions were recorded in June and
September, though some of the accessions only owered in the rst
date. Mature fruits corresponding to these owering peaks were
collected in August and November, respectively. Approximately
between 48 and 96 fruits per accession were collected at maturity
sampling all the plants of the accession. The seeds from all collected
fruits were bulked.
For the study of tocochromanol accumulation in developing
seeds, racemes of accession BGJC-6 were bagged before ower-
ing to avoid contamination with external pollen, using transparent
microperforated plastic bags, made of SM570Y lm (Cryovac ,
Sealed Air Corporation, Elmwood Park, NJ, USA). Each day, pistillate
(female) owers were pollinated with pollen from staminate (male)
owers of the same raceme and immediately tagged to the polli-
nation date. Seed samples were collected at 37-d intervals from
36 days after pollination (DAP) to 124 DAP. Three capsules were
sampled at each date, preferably from different plants. The seeds
were removed from the capsules, stored at 20 C, and lyophilised.
The seeds from each capsule were bulked for tocochromanol anal-
ysis. The data were t to polynomial or sigmoid curves using Origin
7.5 software (OriginLab Corporation, Northampton, MA, USA). The
tocochromanol prole of fruit shells was also monitored during
seed development.
2.3. Analysis of seed oil content
Seed oil content was determined on intact seeds by nuclear
magnetic resonance (NMR) on an Oxford 400 analyzer (Oxford Ana-
lytical Instruments Ltd., Abingdon, OX, United Kingdom). The seeds
were previously dried in the oven at 45 C for 72 h. The instrument
305
was calibrated with unrened J. curcas oil. Seeds were then husked
to determine the percentage of husk.
2.4. Analysis of tocochromanols
Lyophilised seeds from each sample were husked and the ker-
nels ground in a laboratory mill. Around 25 mg meal were weighed
and placed into a 10 ml polypropylene test tube. Tocochromanols
were extracted overnight with 3 ml iso-octane and the extract was
analysed by high-performance liquid chromatography (HPLC) as
described by Goffman et al. (1999), using a uorescence detector
at 295 nm excitation and 330 nm emission and iso-octane/tert-
butylmethylether (94:6) as eluent at an isocratic ow rate of
1.0 ml min1 . Chromatographic separation of tocochromanols was
performed on a LiChrospher 100 diol column (250 mm 3 mm
I.D.) with 5-m spherical particles, connected to a silica guard
column (LiChrospher Si 60, 5 mm 4 mm I.D.). Tocochromanol
homologues were identied by comparison of retention times with
standards including alpha-, beta-, gamma-, and delta-tocopherol
(Cat# 613424 Calbiochem, Merck KGaA, Darmstadt, Germany),
gamma-tocotrienol (Cat#49634 Fluka, SigmaAldrich, St. Louis,
MO, USA), and delta-tocotrienol (Cat# T0452 Sigma, SigmaAldrich,
St. Louis, MO, USA). Quantitative determination of tocochromanols
was done by using external calibration curves. Total tocochromanol
content was expressed as mg kg1 dry seed weight.
2.5. Statistical analysis
Data were analysed by the General Linear Model procedure of
SPSS Statistics 17.0 software. Analysis of variance was performed
with genotypes as xed factors and years as random factors.
3. Results
Total seed tocochromanol content averaged 307.2 mg kg1
(235.9433.8 mg kg1 ) in August and 303.7 mg kg1
(279.5373.1 mg kg1 ) in November. Total oil tocochromanol
content averaged 507.4 mg kg1 (392.2707.0 mg kg1 ) in
August and 500.8 mg kg1 (430.2638.4 mg kg1 ) in November.
The tocochromanol fraction was made up of 15.4% gamma-
tocopherol (10.325.5%), 83.8% gamma-tocotrienol (73.988.8%),
and 0.8% delta-tocotrienol (0.41.1%) in August and 18.0% gamma-
tocopherol (10.432.2%), 80.4% gamma-tocotrienol (67.188.1%),
and 1.6% delta-tocotrienol (0.52.4%) in November.
Analysis of variance (Table 1) showed differences among
genotypes for total seed tocochromanol content (P < 0.05), total
oil tocochromanol content (P < 0.01), and proportion of gamma-
tocopherol and gamma-tocotrienol (P < 0.01). The effect of the
environment was signicant for tocochromanol prole (P < 0.01)
but not for seed and oil tocochromanol content. Conversely,
genotype environment interaction was signicant (P < 0.01) for
seed and oil tocochromanol content and proportion of delta-
tocotrienol, but not for the proportion of the major tocochromanol
homologues gamma-tocopherol and gamma-tocotrienol. Correla-
tion coefcients between both environments were not signicant
for seed and oil tocochromanol content, but they were signi-
cant (P < 0.01) for the proportion of gamma-tocopherol (r = 0.84),
gamma-tocotrienol (r = 0.83) and delta-tocotrienol (r = 0.50).
The analysis of correlation coefcients among tocochromanol
traits showed some differences between both environments
(Table 2). Consistent correlation coefcients expressed in both
environments included a negative correlation between gamma-
tocopherol and both gamma-tocotrienol and delta-tocotrienol
content, and a positive correlation between gamma- and
delta-tocotrienol content. Also, oil tocochromanol content was
positively correlated with seed tocochromanol content. Finally,
306 P.A. Corzo-Valladares et al. / Industrial Crops and Products 36 (2012) 304307

Table 1
Analysis of variance (mean squares) for total tocochromanol content (TTC) in seeds (mg kg1 seed), total tocochromanol content in oil (mg kg1 oil), and proportion of
individual tocochromanols (% of total tocochromanols) in 52 Jatropha curcas L. accessions studied over two environments, summer and autumn of 2009.

Degrees of freedom TTC in seeds TTC in oil Gamma-tocopherol Gamma-tocotrienol Delta-tocotrienol

Genotype 51 2358.6* 48,232.9** 33.9** 31.4** 0.2 ns

Environment 1 1806.0 ns 17,450.0 ns 319.4** 512.2** 22.6**
GxE 34 1284.6** 10,603.9** 5.4 ns 5.0 ns 0.1**
Error 87 199.6 526.4 5.5 5.1 0.04

ns: not signicant.

*
signicant at p < 0.05.
**
signicant at p < 0.01.

delta-tocotrienol content was negatively correlated with seed
tocochromanol content. Oil tocochromanol content showed a
strong negative correlation with oil content in November, but
the correlation was not signicant in August. Seed tocochromanol
content was positively correlated with gamma-tocopherol con-
tent and negatively correlated with gamma-tocotrienol content in
November. Oil tocochromanol content was negatively correlated
with the proportion of gamma-tocotrienol in August.
The analysis of the pattern of accumulation of tocochromanol
homologues during seed development revealed that developing
seeds contained primarily alpha-tocopherol (18.2 mg kg1 ; 35.0%
of total tocochromanols) and gamma-tocopherol (30.4 mg kg1 ;
64.4%) at early stages of development (36 DAP), with gamma-
tocotrienol and delta-tocotrienol being practically undetectable.
Gamma-tocopherol content showed an initial decrease at 42 DAP
and a slight increase at nal stages of seed maturation to reach
nal levels of 46.1 mg kg1 (20.1%) at 124 DAP. Gamma-tocotrienol
content remained practically undetectable till 66 DAP and then
increased pronouncedly to nal levels of 177.1 mg kg1 (74.8%) at
124 DAP (Fig. 1). Alpha-tocopherol content remained unchanged
from 39 DAP (12.3 mg kg1 ) to 124 DAP (10.5 mg kg1 ), though its
weight in the tocochromanol fraction was considerably reduced
(from 26.6 to 4.4%) due to the accumulation of the gamma-
tocopherol and gamma-tocotrienol homologues.
4. Discussion
Jatropha seeds contain high levels of tocochromanols, mainly
in the gamma-tocotrienol form. Total tocochromanol content in
Jatropha seeds, around 300 mg kg1 seed is similar to the lev-
els found in major oilseeds such as rapeseed/canola (Goffman
and Becker, 2002), sunower (Velasco et al., 2010), and soy-
bean (Britz et al., 2008). The present study suggested that total
tocochromanol content in Jatropha seeds is mainly affected by
genotype environment interaction, whereas such an interaction
was not detected for the proportion of the major tocochromanol
homologues, gamma-tocopherol and gamma-tocotrienol, which
resulted in a high positive correlation between the values obtained
in both environments. In canola, both the tocopherol content and
the tocopherol prole (alpha- to gamma-tocopherol ratio) were
mainly inuenced by genotype environment effects, showing
both traits similar heritabilities (Marwede et al., 2004). Conversely,
the main effects of genotype and environment on tocopherol con-
tent were more pronounced than the effect of their interaction
in sunower (Velasco et al., 2002), soybean (Whent et al., 2009)
and peanut (Isleib et al., 2008). Studies on cereal crops containing
both tocopherol and tocotrienol homologues in seeds such as wheat
(Lampi et al., 2010), oats and barley (Peterson and Qureshi, 1993)
and rice (Bergman and Xu, 2003) concluded predominance of the
main effects of genotypes and environments over their interaction
on the content of individual tocochromanol homologues as well as
total tocochromanol content, though the effects on the tocochro-
manol prole were not studied.
Tocochromanol prole of Jatropha seeds is dominated by
gamma-tocotrienol. To our knowledge, this compound had not
been identied previously in Jatropha seeds. A previous publication
described the presence of high levels of gamma-tocopherol (76.9%)
in Jatropha seeds collected in Benin, West Africa (Djenontin et al.,
2006). Our results, including 52 accessions from several countries of
America, Africa and Asia, identied genetic variation for tocopherol
prole, but in all cases gamma-tocotrienol was the predominant
tocochromanol derivative, with a maximum proportion of gamma-
tocopherol of 25.5%. High levels of tocotrienols are found in the
latex of the rubber tree (Hevea brasiliensis [Willd. Ex A. Juss.] Mull.
Arg.), a member of the Euphorbiaceae family to which Jatropha
spp. belongs (Horvath et al., 2006a). Conversely, no tocotrienols are

Table 2
Correlation coefcients among oil content (% kernel), total seed tocochromanol con- 200
-1
tent (Seed TC; mg kg1 kernel), total oil tocochromanol content (Oil TC; mg kg1 Gamma-Tocopherol (mg kg ) 2
Tocochromanol content (mg kg-1)

180 -1
R =0.95
oil) and proportion of gamma-tocopherol (Gamma-T), gamma-tocotrienol (Gamma- Gamma-Tocotrienol (mg kg )
T3), and delta-tocotrienol (Delta-T3), expressed in % of total tocochromanols, in 160
seeds collected in August and November of 2009 from a germplasm collection of 52
accessions of Jatropha curcas L. 140

Seed TC Oil TC Gamma-T Gamma-T3 Delta-T3 120

August harvest 100

Oil content 0.12 ns 0.17 ns 0.06 ns 0.06 ns 0.10 ns 80 2
R =0.65
Seed TC 0.92** 0.00 ns 0.03 ns 0.46**
Oil TC 0.11 ns 0.13 ns 0.46** 60
Gamma-T 0.99** 0.46**
40
Gamma-T3 0.42**
20
November harvest
Oil content 0.24 ns 0.72** 0.11 ns 0.12 ns 0.02 ns 0
Seed TC 0.85** 0.420* 0.40* 0.42* 20 40 60 80 100 120 140
Oil TC 0.24 ns 0.22 ns 0.30 ns
Gamma-T 0.99** 0.64**
Days after pollination
Gamma-T3 0.56**
Fig. 1. Gamma-tocopherol and gamma-tocotrienol content (mg kg1 ) in developing
ns: not signicant. seeds of Jatropha curcas accession BGJC-6 from 36 to 124 days after pollination.
*
signicant at p < 0.05. The data points were t to polynomial (gamma-tocopherol) or sigmoid (gamma-
**
signicant at p < 0.01. tocotrienol) functions.
 P.A. Corzo-Valladares et al. / Industrial Crops and Products 36 (2012) 304307
found in the seeds of castor (Ricinus communis L.), also a member
of the Euphorbiaceae (Velasco et al., 2005). Horvath et al. (2006a)
identied no taxonomic relationship associated to the presence of
tocotrienols in the analysis of 41 dicotyledonous species, though
these compounds were found to have an important chemotaxo-
nomic role in the Orobanchaceae (Velasco et al., 2000).
Tocotrienols have a restricted distribution in plants. Though
cereal grains are the major sources of tocotrienols in human
nutrition, palm oil is the richest food source of tocotrienols
(Zielinski, 2009). Unrened palm oil contains around 1000 mg kg1
tocochromanols, 80% of them being tocotrienols mainly in the
gamma-tocotrienol form (Gunstone and Harwood, 2007). Other oils
with high proportion of tocotrienols in the tocochromanol fraction
are grapeseed (Crews et al., 2006) and coconut oil (Syvoja et al.,
1986).
Tocopherols and tocotrienols have a common biosynthetic path-
way that diverges at the step where a polyprenyl side chain
is attached to homogentisic acid (HGA) (reviewed by Mne-
Saffran and DellaPenna, 2010). At this point, condensation
of HGA and phytyl-diphosphate (Phytyl-PP) forms 2-methyl-
6-phytyl-benzoquinol (MPBQ), the committed intermediate of
the four tocopherol homologues, whereas tocotrienol biosynthe-
sis results from the condensation of HGA and geranylgeranyl
diphosphate (GGPP) into 2-methyl-6-geranylgeranyl-benzoquinol
(MGGBQ), the committed intermediate of tocotrienols. The results
of this research showed that tocopherols were present and
tocotrienols practically absent at the initial steps of seed devel-
opment. During seed development, tocopherol content increased
only slightly, from 48.6 to 56.6 mg kg1 , but tocotrienol content
increased dramatically, from 1.2 to 179.6 mg kg1 , indicating that
the tocotrienol biosynthetic pathway is much more active than
the tocopherol pathway during Jatropha seed development. Simi-
lar observations have been made in grape seeds, where tocopherol
levels decreased from 97.6 mg kg1 at 10 days after owering
(DAF) to 20.4 mg kg1 at 120 DAF, whereas tocotrienol levels
increased from zero at initial stages to 54 mg kg1 at 120 DAF,
with tocotrienol accumulation being particularly active from 60
DAF (Horvath et al., 2006b).
Like tocopherols, tocotrienols are compounds with vitamin
E activity. Several studies have concluded that tocotrienols
exert higher antioxidant activity than tocopherols (Packer et al.,
2001; Chandan et al., 2006; Harinantenaina, 2009). Additionally,
tocotrienols possess more powerful hypocholesterolemic and anti-
tumor properties than tocopherols (Zielinski, 2009). Because of the
importance of tocotrienols as antioxidants, the role of the toco-
pherol/tocotrienol ratio in Jatropha oil may inuence its oxidative
stability. The present research revealed the existence of genetic
variation for tocochromanol prole in Jatropha germplasm, which
anticipates the possibility of selection for different levels of the
tocopherol/tocotrienol ratio in this species. Also, the high levels
of tocotrienols in Jatropha seeds should encourage further studies
on the losses of these compounds during oil rening and the possi-
bility to recover them as high added-value products derived from
Jatropha seed oil production.
Acknowledgments
The authors wish to thank the Estacin Experimental La Mayora
(CSIC) for facilities provided during the execution of this research
and Alberto Merino and Manuel Gonzlez for technical support. The
research was funded by Bionor Transformacin S.A.
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