Food Research International 48 (2012) 98–107

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Food Research International

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Analysis of the volatile compounds of Brazilian chilli peppers (Capsicum spp.) at two
stages of maturity by solid phase micro-extraction and gas
chromatography-mass spectrometry
Stanislau Bogusz Junior a, Arlete Marchi Tavares b, José Teixeira Filho c,
Claudia Alcaraz Zini d, Helena Teixeira Godoy a,⁎
a
Department of Food Science. Faculty of Food Engineering, Campinas State University (UNICAMP) P.O. Box 6121, Campinas, SP, Brazil
b
Horticultural Center, Campinas Agronomic institute (IAC), Campinas, SP, Brazil
c
Faculty of Agricultural Engineering, Campinas State University (UNICAMP), Campinas, SP, Brazil
d
Federal University of Rio Grande do Sul (UFRGS), Institute of Chemistry, Porto Alegre, RS, Brazil

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

Article history: The volatile fractions of three varieties of chilli peppers at two stages of maturity were characterised using
Received 2 July 2011 headspace solid phase micro-extraction (HS-SPME), gas chromatography (GC-FID) and mass spectrometry
Accepted 12 February 2012 (GC–MS). A total of 83 compounds, mostly esters and alcohols, were identified in the malagueta chilli pepper
(Capsicum frutescens), 49 compounds, mostly monoterpenes and aldehydes, were identified in the dedo-de-moça
Keywords:
chilli pepper (Capsicum baccatum var. pendulum) and 77 compounds, mostly esters and sesquiterpenes, were
Capsicum frutescens L.
C. chinense Jacq.
identified in the murupi chilli pepper (Capsicum chinense). The peak areas of the compounds were smaller in
C. baccatum (Willd) Eshbaugh the more mature samples. The samples from C. baccatum var. pendulum exhibited the greatest decrease; most
Volatile compounds of the compounds were not detected in the more mature samples.
Solid phase micro-extraction and gas © 2012 Elsevier Ltd. All rights reserved.
chromatography-mass spectrometry

1. Introduction
Chilli peppers of the genus Capsicum are very popular in many parts
of the world due to their colour, pungency and aroma (Pruthi, 1980;
Sousa et al., 2006). They are used industrially as colouring and flavouring
agents in sauces, soups, processed meats, lunches, sweets and alcoholic
beverages (Kollmannsberger, Rodrıguez-Burruezo, Nitza, & Nuez, 2011;
Pino et al., 2007). They can be consumed (in ripe and unripe stages)
fresh, dried, in conserves or in the form of pepper sauces. They are also
used in traditional medicine for their antimicrobial, anti-convulsive
and sedative properties (Cichewicz & Thorpe, 1996; Molina-Torres,
Garcia-Chávez, & Ramirez-Chávez, 1999; Otero et al., 2000).
Brazil, a centre of genetic diversity, is one of the world's largest
producers of Capsicum peppers. In the year 2005, peppers of this
genus were the second-most exported vegetable from Brazil, with an
exportation volume of 9222 tons (Embrapa, 2005). Some of the most
popular domesticated varieties cultivated in the Brazilian territory
are the malagueta (Capsicum frutescens), dedo-de-moça (Capsicum
bacccatum var. pendulum) and murupi (Capsicum chinense) peppers.
Although pungency is one of the most important attributes of Capsi-
cum fruits, several previous studies have analysed the volatile fraction
⁎ Corresponding author. Tel.: + 55 19 3521 4024; fax: + 55 19 3521 2153.
E-mail address: helena@fea.unicamp.br (H.T. Godoy).
because the chemical compounds present in this fraction directly affect
the flavour (Pino, Sauri, & Marbot, 2006; van Ruth, Boscaini, Mayr, Pugh,
& Posthumus, 2003). Moreover, the perception of the complex volatile
mixture of compounds is an important part of the consumers' selection
criteria for the acceptance of food; although differences attributed to
non-volatile components of food, such as sugars, alkaloids, salts and
acids, also play a major role in this respect. Thus the knowledge of the
composition of these volatiles compounds is an important tool for dif-
ferentiating between the types of Capsicum, and also to establish criteria
for authenticity, quality improvement, fraud prevention and assurance
of origin. In addition, the food industry has an interest in obtaining con-
centrated aroma of peppers for flavoured products without necessarily
giving pungency to food (Pino, Fuentes, & Barrios, 2011).
Some studies have described several flavour components, common
to different kinds of chilli peppers, such as, 2,3-butanedione (flavour
of caramel), 1-penten-3-one (pungent, spicy), hexanal (grassy, herbal),
3-carene (red bell pepper, lemon), ocimene (sweet, herb), octanal
(fruity), (E)-2-hexenal (sweet), (E)-3-hexenol, 2-sec-butyl-3-2-
methoxypyrazine and isobutyl-3-methoxypyrazine (green bell pepper)
(Chitwood, Pangborn, & Jennings, 1983; Mazida, Salleh, & Osmanet,
2005). However, the investigation of the composition of volatile organic
compounds present in fruits of different kinds of peppers is an issue of
continuous interest for scientific research around the world, due to
the great genetic diversity of Capsicum and due to the edaphoclimatic

0963-9969/$ – see front matter © 2012 Elsevier Ltd. All rights reserved.
doi:10.1016/j.foodres.2012.02.005
 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107
effects of each producing country. In addition, the process of pepper
ripening can lead to variations in the composition of volatile compo-
nents responsible for specific flavours, as is the case of change of flo-
ral scent (3-carene) to almond, scent, and from fruity to spicy scent
(E-2-hexenal and E-2-hexenol) which had been observed in Jalapeño
peppers (Keller et al., 1981).
The analytical task of characterising the volatiles of a sample is not
simple, and different analytical methods have been developed and
employed for the analysis of fresh, dried and processed samples of pep-
pers. The most widely employed extraction methods are the simulta-
neous distillation and extraction (SDE) method and the headspace
purge and trap method. However, these methods are laborious, lengthy
and error-prone. Artefacts can be induced during the sample prepara-
tion steps by the use of different solvents and by the elimination of
these solvents to concentrate the volatiles obtained (Mazida et al.,
2005). One alternative for these methods is headspace solid phase
micro-extraction (HS-SPME). Since this is an extraction and concentra-
tion technique for volatiles that do not use solvents, the concentrations
necessary for adequate characterisation are readily attained. This meth-
od is also relatively simple and rapid and requires fewer instrumental
devices than other methods for isolating volatiles (Bogusz Junior,
Melo, Zini, & Godoy, 2011).
The goal of this study was the characterization of the chromato-
graphic profile of volatile compounds of both ripe and unripe mala-
gueta, dedo-de-moça and murupi peppers cultivated in Brazil, using
HS-SPME and gas chromatography (GC) with flame ionisation detec-
tion (FID) and GC with mass spectrometric detector (MS).To our
knowledge, this is the first report on the constituents of the volatile
fraction in Brazilian Capsicum peppers in different maturation stages.
2. Material and methods
2.1. Standards
The following pure compounds were purchased from Fluka
(Buchs, Switzerland) for use as reference standards: (E)-2-hexen-1-ol,
Fig. 1. GC-FID chromatograms of the volatile fraction of the malagueta pepper (Capsicum frutescens) by HS-SPME from (A) immature and (B) mature fruits.
99
(E)-2-hexenal, (E)-β-farnesene, 1-decanol, 1-dodecanol, 1-hexanol, 1-
octanol, 1-pentadecene, 1-tridecanol, 2-nonanone, 5-hexenol, butanal,
heptadecane, hexyl isovalerate, linalool, methyl salicylate, pentadecane,
pentane, tetradecane, undecane, α-ionone, β-pinene and γ-terpinene.
The following pure compounds were purchased from Aldrich (St. Louis,
USA) for use as reference standards: 1-hexadecene, (Z)-2-dodecenal,
(E)-2-tridecenal, 2-methoxy-3-isobutylpyrazine, 2-methyl-butanal, 2-
pentyl-furan, 3-methyl-butanal, camphene, ethyl hexanoate, eucalyptol,
heptanal, heptyl isobutyrate, hexanal, hexyl butyrate, hexyl isobutyrate,
hexyl pentanoate, isobutyl isovalerate, limonene, neral, nonanal, p-
cimene, pentanal, tridecanal, α-copaene, α-humulene, α-phellandrene,
α-pinene, α-terpinene, β-myrcene, β-caryophyllene, β-ionone, and
δ-3-carene.
2.2. Samples
The samples of malagueta, dedo-de-moça and murupi peppers
(about 2 kg of each species) were obtained from the Campinas Agro-
nomic Institute (IAC) in the city of Campinas, São Paulo, Brazil. The
genotypes selected for the study were obtained from the germplasm
bank of the Horticultural Center of the IAC — Campinas. The plants
were cultivated under similar conditions of fertilisation and irrigation
in two distinct periods one from April to July, 2008, and the other
from January to May, 2009. The plants were botanically identified at
the IAC — Campinas. The pepper samples were harvested at two
stages of maturity: the physiological stage (maximum size develop-
ment, but still immature) and the commercial stage (complete devel-
opment of both size and colour). The peppers were harvested in the
morning and immediately transported to the laboratory for analysis.
The period between harvesting and sample analysis was not longer
than 3 days.
2.2. Sample preparation
The volatiles were extracted by HS-SPME according to our previ-
ously published procedure (Bogusz Junior et al., 2011). Whole pepper
100 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107

Table 1
Characterisation of the volatile compounds in malagueta peppers (Capsicum frutescens L.) grown in two distinct years at two stages of maturation by HS-SPME, GC-FID and GC–MS.

Compound ID LTPRICal. LTPRILit. Δ 2008 2009

Immaturea,1 Maturea Immaturea Maturea

Alkanes
Undecane A 1100 1100 0 0.01b t 0.13a 0.11a
(Z)-3-tetradecene B 1421 1421 0 0.06c 0.03c 0.94a 0.46b
1-pentadecene A 1490 1489 −1 0.10a 0.06b 0.08b 0.02c
Pentadecane A 1499 1500 1 0.03b 0.05a 0.05a 0.02b
1-hexadecene A 1581 1589 8 0.06c 0.08bc 0.45a 0.17b
Hexadecane B 1598 1600 2 0.65c 1.18b 2.21a 0.74c
(Z)-7-hexadecene B 1614 1620 6 0.03b 0.06ab 0.07a 0.03b
Heptadecane A 1699 1700 1 0.13c 0.29b 0.72a 0.22bc

Alcohols
2-propanol B 474 482 8 0.10a 0.03ab 0.03ab 0.02b
1-pentanol B 765 761 −4 0.01a 0.01a 0.02a 0.01a
4-methyl-pentanol B 833 831 −2 0.38b 0.81a 0.26b 0.42b
(Z)-4-hexenol B 853 857 4 0.41a 0.02c 0.10b 0.10b
(E)-2-hexen-1-ol A 866 868 2 0.15a 0.01b 0.13a 0.01b
1-hexanol A 866 860 −6 0.09a 0.08a 0.02b 0.02b
4-butoxy-1-butanol B 1139 1135 −4 0.02a 0.01a 0.04a 0.02a
2-decanol B 1179 1178 −1 0.02a 0.01b 0.01b 0.01b
2,4-nonadien-1-ol B 1196 1200 4 0.95a 0.07c 0.91a 0.22b
1-decanol A 1260 1260 0 0.04c 0.02c 0.28a 0.08b
(Z)-6-nonen-1-ol B 1294 1290 −4 0.13b 0.19a 0.03c 0.02c
10-undecen-1-ol B 1346 1347 1 1.13a 0.35c 1.24a 0.5b
(E)-2-undecen-1-ol B 1355 1355 0 4.45a 2.67c 3.76b 1.80 d
2,2-dimethyl-1-decanol B 1363 1372 9 0.08a 0.05ab 0.07a 0.03b
1-dodecanol A 1562 1564 2 0.09b 0.08b 0.18a 0.04b
1-tridecanol A 1563 1572 9 0.04c 0.01c 0.48a 0.18b
1-tetradecanol B 1662 1656 −6 0.01a 0.01a 0.01a 0.01a
(E)-3-pentadecen-2-ol B 1677 1683 6 0.09c 0.12b 0.43a 0.14b

Aldehydes
Butanal A 556 558 2 0.03a 0.01a 0.01a t
2-methyl-butanal A 649 643 −6 0.01a t 0.01a t
Pentanal A 701 696 −5 0.01a t 0.01a t
Hexanal A 801 806 5 0.06a 0.01b 0.04a t
(E)-2-hexenal A 851 850 −1 0.26a 0.09b 0.24a 0.10b
(Z)-4-heptenal B 871 869 −2 0.04a 0.01a t t
Heptanal A 872 873 1 0.01a 0.01a 0.01a –
(Z)-2-decenal B 1218 1212 −6 0.02a 0.02a 0.03a 0.01a
(E)-2-dodecenal B 1447 1442 −5 2.89b 3.01b 5.47a 3.30b
(Z)-2-dodecenal B 1449 1447 −2 0.29b 0.24b 0.66a 0.24b
Myric aldehyde B 1485 1488 3 0.03b 0.09b 0.12a 0.06b
Tridecanal A 1493 1494 1 0.91b 1.00b 2.14a 0.87b
(E)-2-tridecenal A 1543 1549 6 0.08a 0.06a 0.04b 0.01b

Ketones
(E)-5-methyloct-5-en-2-one B 1040 1037 −3 t t 0.01a 0.01a
2-nonanone A 1055 1052 −3 0.05c 0.04bc 0.10a 0.07ab

Esters
Ethyl hexanoate A 968 978 10 0.02a 0.02a 0.01b 0.01b
Hexyl acetate B 978 984 6 0.43a 0.03b 0.06b 0.01b
Isobutyl isovalerate A 1007 1005 −2 0.01b t 0.06a 0.01b
Isopentyl isobutyrate B 1013 1014 1 0.01a 0.02a 0.01a 0.01a
Prenyl isobutyrate B 1060 1050 − 10 0.06a 0.01c 0.05ab 0.02bc
2-methylbutyl 2-methylbutyrate B 1100 1104 4 0.04b t 0.22a 0.06b
2-methylbutyl isovalerate B 1106 1109 3 0.32a 0.16b 0.25a 0.08b
Hexyl isobutyrate A 1113 1118 5 2.62b 1.85 d 6.86a 2.62b
7-methyl-4-octyl acetate B 1148 1154 6 0.15c 0.16c 0.46b 0.61a
Hexyl butanoate A 1157 1155 −2 0.12b 0.02 d 0.23a 0.06c
(E)-3-hexenyl butyrate B 1187 1191 4 0.31a 0.12b 0.11b 0.08b
Hexyl 2,2-dimethylpropanoate B 1201 1197 −4 8.26b 7.80b 13.81a 7.83b
Hexyl 3-methylbutanoate B 1208 1202 −6 7.02c 6.84 d 31.79b 24.16a
2-methylbutyl hexanoate B 1215 1218 3 0.50a 0.21b 0.28b 0.12c
(Z)-3-hexenyl isopentanoate B 1231 1226 −5 0.02b 0.01b 0.03a 0.01b
(Z)-3-hexenyl-2-methyl butanoate B 1232 1231 −1 1.46b 0.34 d 1.93a 0.86c
Hexyl 2-methyl butyrate B 1237 1239 2 4.44b 1.61 d 7.07a 3.68c
3-methyl-hexyl butyrate B 1242 1243 1 2.12c 0.82 d 5.64a 3.41b
Heptyl isobutanoate B 1247 1248 1 3.12a 1.95b 3.45a 1.66b
3-methyl-2-butenyl hexanoate B 1263 1273 10 0.05a 0.01a 0.09a 0.01a
(Z)-3-hexenyl pentanoate B 1284 1282 −2 0.19b 0.04 d 0.53a 0.10c
Hexyl pentanoate A 1289 1282 −7 0.54a 0.09 d 0.48b 0.29c
Butyl isohexyl carbonate B 1303 1294 −9 0.06a t 0.06a t
Heptyl 2,2-dimethylpropanoate B 1306 1297 −9 0.03b 0.02b 0.13a 0.12a
 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107 101

Table 1 (continued)
Compound ID LTPRICal. LTPRILit. Δ 2008 2009

Immaturea,1 Maturea Immaturea Maturea

Esters
Heptyl 2-methylbutyrate B 1311 1317 6 0.18c 0.16 d 0.29b 0.37a
2-methylpentyl hexanoate B 1316 1317 1 14.06b 16.98a 12.21b 8.93c
Methyl geranoate B 1330 1322 −8 0.08b 0.03c 0.17a 0.02c
2-ethylhexyl pivalate B 1335 1332 −3 0.03c 0.14c 1.08a 0.71b
Allyl heptyl carbonate B 1340 1348 8 0.11b 0.26a 0.09b 0.13b
(E)-5-decenyl acetate B 1387 1389 2 1.39a 1.71a 1.36a 0.54b
Benzyl 2-methylbutanoate B 1394 1394 0 0.09c 0.08c 0.48a 0.28b
Octyl pivalate B 1402 1396 −6 0.44a 0.14b 0.42a 0.03c
Allyl decanoate B 1463 1471 8 0.16a 0.10b 0.03c 0.04c

Monoterpenes
δ-3-carene A 1011 1014 3 0.03a t 0.01a t
(E)-β-ocimene B 1047 1041 −6 0.02c 0.03bc 0.12a 0.06b

Sesquiterpenes
β-caryophyllene A 1415 1410 −5 0.22a 0.23a 0.06b 0.08b
α-ionone A 1428 1421 −7 0.20a 0.25a 0.05b 0.03b
Cadinadiene B 1440 1440 0 0.14c 0.19b 0.22a 0.20a
α-selinene B 1475 1474 −1 4.03b 1.93 d 6.93a 2.51c
β-(E)-bergamotene A 1480 1483 3 1.26b 0.25c 1.51a 0.12 d
β-ionone A 1486 1485 −1 0.01b 0.01b 0.15a 0.08b
δ-cadinene B 1521 1518 −3 0.02b 0.01b 0.05a 0.02b

ID = identification by A = mass spectrum and linear retention index agreed with the standards; B = mass spectrum and linear retention index agreed with the literature data.
LTPRICalc. = retention indexes obtained using a 5% phenyl/95% dimethylpolysiloxane capillary column.
LTPRILit. = retention indexes from the literature obtained using a 5% phenyl/95% dimethylpolysiloxane capillary column.
Δ = differences between the calculated retention indexes and those from the literature; LTPRILit—LTPRI Calc.
T = trace level (area less than 0.01).
– = not detected.
Different letters in the same row indicate significant difference by Tukey test at p ≤ 0.05.
a
Peak area divided by 106, obtained by GC-FID (detector response factors equal to unity); the results are presented as the mean of triplicate experiments.
1
Data for the identification of compounds in the volatile fraction from immature malagueta chilli peppers harvested in 2008 were previously reported by Bogusz Jr., Melo, Zini,
and Godoy, 2011.

fruits were ground in a blender in 100 g batches, and 1.00 g aliquots
of the ground material were weighed into 15.0 mL SPME flasks with
screw tops and PTFE/silicon septa (Supelco — Bellefonte, PA, USA).
The fibre used in this study was 50/30 μm divinylbenzene/carboxen/
polydimethylsiloxane (DVB/CAR/PDMS) obtained from Supelco
(Bellefonte, PA, USA) and conditioned before use according to the
manufacturer's instructions. The volatiles were extracted under the
following optimised conditions: equilibration for 15 min followed
by extraction for 80 min, at 40 °C. After extraction, the fibre was
placed in the injector of the gas chromatograph, and the analytes
were desorbedin in the splitless mode at 250 °C for 1.0 min. After
each extraction and desorption procedure, the fibre was recondi-
tioned for 15 min at 250 °C, according to the manufacturer's recom-
mendations, to guarantee clean blank runs and good quality of the
SPME extraction procedures. All of the samples were analysed in
triplicate, and the results are presented as the mean values. The rel-
ative standard deviation (RSD%) of the volatile compounds from
these peppers and the sum of the peak areas of all identified com-
pounds was below 10%, which indicated that the extraction method
performed well.
2.3. Gas chromatography (GC-FID)
To obtain the peak areas of the volatile compounds from the peppers
without needing to calculate correction factors for the responses from the
mass detector, the samples were also injected into a Varian 3800 GC
coupled to a flame ionisation detector (FID), using the “Star Chromatogra-
phy” Workstation (version 4.5). A fused silica HP-5 MS capillary column
(5% phenyl/95% dimethylpolysiloxane) (30 m×0.25 mm i.d.×0.25 μm
of film thickness) from Supelco (Bellefonte, PA, USA) was used to separate
the volatile compounds. The instrumental conditions used were as
follows: injector (mode and temperature), splitless, for 1.0 min at
250 °C; stripping gas, hydrogen at 1.0 mL.min− 1; oven, 40 °C, increased
to 240 °C at 3 °C min− 1 and remained at this temperature for 4 min;
and detector temperature, 250 °C.
2.4. Gas chromatography–mass spectrometry (GC–MS)
The GC–MS analyses were conducted on a Shimadzu GC-17A/QP-
5000 (Japan) instrument using a fused silica HP-5 MS capillary column
(5% phenyl/95% dimethylpolysiloxane) (30 m × 0.25 mm i.d.× 0.25 μm
of film thickness) from J&W Scientific (USA). The instrumental parame-
ters used were as follows: injector, splitless mode for 1.0 min at 250 °C;
stripping gas, helium at 1.0 mL.min− 1; oven, 40 °C, increased to 240 °C
at 3 °C min− 1 and remained at this temperature for 4 min; interface
temperature, 240 °C; electronic ionization at 70 eV; quadrupole mass
analyzer; and mass range 35–350 m/z.
The Van den Dool and Kratz linear temperature programmed re-
tention indexes (LTPRI) of the volatile compounds were calculated
by subjecting a mixture of aliphatic hydrocarbons (C6–C20) (Poly-
Science, Illinois, USA) to extraction in an SPME flask and injection
under the same conditions as the pepper samples (Van Den Dool &
Kratz, 1963). The LTPRI below C6 were obtained by extrapolation of
the LTPRI curve. The compounds were identified by comparing the
LTPRI and the mass spectra obtained from the samples with the
LTPRI and mass spectra obtained from the standards, the literature
data (Adams, 2007) and NIST 2005, using criteria of at least 85% sim-
ilarity for the mass spectra and maximum variation of the retention
indices of ±10.
Because the extraction and concentration functions of SPME result
from partitioning and the equilibria of the volatiles between the
ground sample, the headspace and the fibre and because each distinct
102 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107
chemical component has its own partition coefficient, attempts to
quantify or semi-quantify the components present in the sample
must take into account the individual equilibrium of each chemical
component (Nongonierma, Cayot, Le Quéré, Springett, & Voilley,
2006). Given the complexity of the samples, the number of identified
compounds and the goal of this research, the values for the peak areas
obtained by GC-FID presented in the results below (treating the cor-
rection factors of the detector response as equal to unity) do not rep-
resent the true quantities of the volatiles in the samples and are only
a parameter for comparing the maturation-related variations in the
volatile compounds of a single sample.
3. Results and discussion
3.1. Volatiles of the malagueta pepper
The GC-FID chromatograms of the volatile fraction of immature
(A) and mature (B) malagueta peppers are shown in Fig. 1. The
peak areas from the GC-FID analysis and the corresponding GC–MS
identification results are shown in Table 1.
In total, 83 compounds from the following chemical classes were
identified in the malagueta pepper samples: esters (40%), alcohols
(22%), aldehydes (16%), alkanes (10%), sesquiterpenes (8%), mono-
terpenes (2%) and ketones (2%). The predominance of volatile esters
in chilli peppers is in agreement with the results found in other
varieties of C. frutescens as in the case of laotilan, tabasco and
pebre chilli peppers, which had esters as their major volatile com-
pounds (Rodríguez-Burruezo et al., 2010).
Clear changes can be seen in the peak areas of the volatiles from
fruits harvested at different stages of maturity. The general tendency
of the peak areas to decrease as the fruits mature is consistent with
earlier studies of fruits from the genus Capsicum (2007; Forero,
Quijano, & Pino, 2009, Pino et al., 2006).
The malagueta pepper samples contained 33 esters, including
compounds such as 2-methylpentyl hexanoate, hexyl 2,2-dimethyl
propanoate and hexyl 3-methyl butanoate. The sensory description
Fig. 2. GC-FID chromatograms of the volatile fraction of dedo-de-moça peppers (Capsicum baccatum var. pendulum) by HS-SPME from (A) immature and (B) mature fruits.
of most of these compounds possessed potent fruity notes
(Pherobase, 2011; Pino et al., 2011). These esters have been previously
identified in habanero peppers from México (C. chinense Jacq. cv.
Habanero) and in piquín peppers (C. annuum L. var glabriusculum)
from Colombia (Forero et al., 2009; Pino et al., 2007). Tabasco pep-
pers analysed by sniffing revealed that several esters contribute to
the quality and intensity of the odour, and in particular ethyl hexyl
methylpentanoates/butanoates. On the other hand, phenolic ester
methyl salicylate showed moderate contribution to the odour of
C. peppers laotilan, pebrera and tabasco (Rodríguez-Burruezo
et al., 2010).
The composition of the esters found in malagueta peppers differed
greatly from those found in green peppers and paprika, for which
only a small number of esters were reported (Cremer & Eichner,
2000; Kim et al., 2007; Luning, Rijk, Wichers, & Roozen, 1994;
Mazida et al., 2005; van Ruth et al., 2003). The only alcohols and alde-
hydes of sensory importance that were common to both malagueta
peppers and green peppers (C. annuum cv. Masurka) were 1-
hexanol, 2-hexanol, hexanal and (E)-2-hexenal (Luning et al., 1994).
Because alcohols have a higher odour threshold, however, the impor-
tance of alcohols in the aroma of foods is small relative to that of alde-
hydes. The aromas of many of the 13 aldehydes identified in the
malagueta peppers, such as butanal, hexanal and pentanal, have
been described as green, pungent or herbaceous. Other aldehydes
identified in the malagueta peppers, such as (Z)-2-decenal, myrac
aldehyde, (E)-2-tridecenal and tetradecanal, have aromas that have
been described as aldehydic/floral (Good Scents, 2011, Pino et al.,
2006; Luning et al., 1994; Chitwood et al., 1983).
Seven sesquiterpenes and two monoterpenes were identified in the
malagueta peppers. Of these, δ-3-carene is significant because it is an
important component of the aroma of green peppers (Schwab &
Roscher, 1997). Carotenoid degradation products, such as α-ionone
and β-ionone, were also found. These compounds exhibit very low
aroma threshold values and have been described as floral/fruity
(Flavornet, 2011; Schwab & Roscher, 1997). The β-ionone was reported
like high intensity for odour quality in laotilan peppers from Laos and
 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107 103

Table 2
Characterisation of the volatile compounds in dedo-de-moça peppers (Capsicum baccatum L. var. Pendulum (Willd) Eshbaugh) grown in two distinct years at two stages of matu-
ration by HS-SPME, GC-FID and GC–MS.

Compound ID LTPRICal. LTPRILit. Δ 2008 2009

Immaturea Maturea Immaturea Maturea

Alkanes
Pentane A 498 500 2 1.12a 0.68c 0.87b 0.50 d
Isooctane B 691 687 −4 0.29a 0.32a t 0.14b
2-methyl-tridecane B 1365 1365 0 0.82b – 1.51a –
Tetradecane A 1401 1400 −1 0.02a – t –
pentadecane A 1501 1500 −1 1.07b – 1.47a –

Alcohols
(E)2,3-methylpenta-2,4-dienol B 843 836 −7 0.36a – 0.40a –
5-hexenol A 848 839 −9 31.06b – 35.11a –
1-hexanol A 867 860 −7 0.17b – 0.36a –

Aldehydes
2-methyl-propanal B 553 543 − 10 1.39a – 0.26b –
butanal A 604 607 3 0.55a – 0.38b –
3-methyl-butanal A 650 643 −7 0.68b 0.30c 0.80a 0.32c
2-methyl-butanal A 661 662 1 0.18a – 0.19a –
pentanal A 701 696 −5 0.34a – 0.33a –
3-methyl-2-butenal B 753 754 1 0.13a – 0.15a –
Hexanal A 801 806 5 25.63b 0.38c 29.13a 0.28c
Heptanal A 905 901 −4 0.21b – 0.34a –
Nonanal A 1108 1104 −4 0.26a – 0.30b –
(E)-2-dodecenal B 1442 1448 6 0.24b – 0.33a –

Ketones
1-penten-3-one B 688 687 −1 0.53a – 0.56a –

Esters
Methyl isopentanoate B 773 773 0 2.49a – 2.86a –
Methyl tiglate B 844 841 −3 0.37b – 0.57a –
Hexyl 2-methyl butyrate B 1217 1218 1 0.35a 0.04c 0.29b t
Hexyl isovalerate A 1244 1243 −1 0.26b 0.12 d 0.35a 0.14c
Allyl decanoate B 1465 1471 6 0.62a – 0.43b –

Monoterpenes
δ -3-carene B 919 919 0 0.54b – 0.69a –
α-pinene A 931 935 4 0.34a 0.11b 0.37a 0.12b
Camphene A 945 950 5 0.54b – 0.76a –
Sabinene B 971 972 1 1.24a – 1.23a –
β-pinene A 973 976 3 0.83a – 0.82a –
β-myrcene A 991 987 −4 1.47b – 2.11a –
α- phellandrene A 1003 1003 0 0.07 – t –
α-terpinene A 1008 1007 −1 1.91a – 1.69b –
p-ocimene A 1023 1025 2 0.23b – 0.32a –
Limonene A 1027 1028 1 5.45b 0.57c 6.17a 0.66c
Eucalyptol A 1029 1027 −2 1.6b 0.58c 2.11a 0.59c
(E)-sabinene hydrate B 1057 1051 −6 0.64a 0.04c 0.46b t
γ-terpinene A 1067 1058 −9 0.02 – t –
1,4(8)-p-menthadiene B 1087 1086 −1 0.11b – 0.17a –
Linalool A 1102 1097 −5 0.78a – 0.69b –
β-terpineol B 1146 1153 7 0.01 – t –
Terpinen-4-ol B 1177 1172 −5 0.10a – 0.03b –

Sesquiterpenes
Patchulane B 1291 1293 2 0.18a 0.07b t t
δ-elemene B 1337 1338 1 0.68a – 0.63b –
α-copaene A 1375 1375 0 0.53b 0.10c 0.94a 0.09c
β-caryophyllene A 1418 1418 0 8.23b 3.22 d 11.7a 5.27c
Humulene A 1452 1454 2 0.63b 0.12c 0.97a 0.14c
Germacrene D B 1480 1480 0 0.99a – 0.66b –
Cadinene B 1523 1528 5 0.34b – 0.88a –

Pyrazine
2-methoxy-3-isobutylpyrazine A 1182 1181 −1 0.94b 0.05c 1.27a 0.03c

ID = identification by A = mass spectrum and linear retention index agreed with the standards; B = mass spectrum and linear retention index agreed with the literature data.
LTPRICalc. = retention indexes obtained using a 5% phenyl/95% dimethylpolysiloxane capillary column.
LTPRILit. = retention indexes from the literature obtained using a 5% phenyl/95% dimethylpolysiloxane capillary column.
Δ = differences between the calculated retention indexes and those from the literature; LTPRILit - LTPRI Calc.
T = trace level (area less than 0.01).
– = not detected.
Different letters in the same row indicate significant difference by Tukey test at p ≤ 0.05.
a
Peak area divided by 106, obtained by GC-FID (detector response factors equal to unity); the results are presented as the mean of triplicate experiments.
104 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107
pebrera pepper from Spain, whereas the compound α-ionone
showed moderate importance for odour quality these two varieties
of C. frutescens (Rodríguez-Burruezo et al., 2010)
Significantly, no methoxypyrazine compounds were identified
in the malagueta samples. Methoxypyrazines have an extremely
low odour threshold values (0.002 ng.L − 1), are the most important
flavour compounds in green peppers, and are responsible for their
characteristic green aroma (Forero et al., 2009; Luning et al., 1994;
Mazida et al., 2005; Pherobase, 2011; Pino et al., 2006).
3.2. Volatiles of the dedo-de-moça pepper
The GC-FID chromatograms of the volatile fraction of immature
(A) and mature (B) dedo-de-moça peppers are shown in Fig. 2. The
peak areas from the GC-FID analysis and the corresponding GC–MS
identification results are shown in Table 2.
The chromatograms and the peak areas obtained by GC-FID dem-
onstrate that most of the volatile compounds decreased drastically
and some volatile compounds decreased to the point they cannot be
detected during the maturation process.
In total, 49 compounds from the following chemical classes were
identified in the dedo-de-moça pepper samples: monoterpenes (34%),
aldehydes (18%), sesquiterpenes (14%), esters (12%), alkanes (10%),
alcohols (8%), ketones (2%) and methoxypyrazines (2%). This number
of volatile compounds found in Brazilian dedo de-moça pepper was
lower than that found in other varieties of Capsicum. Colombian piquin
pepper (Capsicum annum L. var. Glabriusculum) presented 140 com-
pounds identified (mostly esters); Spanish aji peppers (C. baccatum)
showed 119 volatiles identified (mostly esters and terpenes) and
Spanish rocoto pepper (Capsicum pubescens) had 76 volatiles tentatively
identified (mainly terpenes) (Forero et al., 2009; Kollmannsberger et al.,
2011; Rodríguez-Burruezo, Kollmannsberger, González-Mas, Nitz, &
Nuez, 2010).
Compared to the malagueta peppers, the dedo-de-moça peppers
contained fewer esters and more terpenes. Four compounds with pre-
viously described sensory attributes in Capsicum were among the al-
dehydes identified in the dedo-de-moça peppers: 3-methylbutanal
Fig. 3. GC-FID chromatograms of the volatile fraction of murupi peppers (Capsicum chinense) by HS-SPME from (A) immature and (B) fruits.
(fruity), 2-methylbutanal (green), hexanal (herbaceous) and nonanal
(mushroom-like) (Luning et al., 1994; Pherobase, 2011). These com-
pounds have been shown to be important for the odour of green pep-
pers of the variety C. annuum cv. Masurka (Luning et al., 1994). Unlike
the malagueta peppers, the dedo-de-moça peppers did contain a
methoxypyrazine, specifically 2-methoxy-3-isobutylpyrazine. Analy-
sis by sniffing pointed out that this is one of the pyrazines that has
a greater impact on the quality and odour intensity of several varie-
ties of C. baccatum, C. pubescens and C. annum (Kollmannsberger
et al., 2011; Rodríguez-Burruezo et al., 2010). The drastic decrease
of the peak areas of the identified compounds in the more mature
samples suggests that the immature dedo-de-moça peppers have a
more complex aroma than the mature specimens.
3.3. Volatiles of the murupi pepper
The GC-FID chromatograms of the volatile fraction of immature
(A) and mature (B) murupi peppers are shown in Fig. 3. The differ-
ences in the number and in the areas of volatile compounds between
the two stages of maturation of murupi peppers were not as obvious
as those observed for the dedo-de-moça peppers.The peak areas from
the GC-FID analysis and the corresponding GC–MS identification re-
sults are shown in Table 3. In total, 77 volatile compounds from the
following chemical classes were identified in the murupi pepper sam-
ples: esters (35%), sesquiterpenes (21%), alcohols (16%), aldehydes
(12%), monoterpenes (12%), alkanes (3%) and furan ether (1%). The
number of volatile compounds found in murupi peppers was lower
than that found in farolillo pepper (C. chinense) from Ecuador, in
which 155 volatiles were identified (mostly esters). Cachuca pepper
(C. chinense Jacq.) from Cuba presented 136 volatiles (mostly esters)
and piquín pepper (C. annuum var. glabriusculum) from Colombia
showed 140 volatiles (mostly esters) (Forero et al., 2009; Pino et al.,
2011; Rodríguez-Burruezo et al., 2010).
Similar to the malagueta peppers, the murupi peppers contained
an assortment of linear and branched esters, which contribute “po-
tent fruity notes” to the sensory description of the aroma
(Pherobase, 2011; Pino et al., 2011; Rodríguez-Burruezo et al.,
 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107 105

Table 3
Characterisation of the volatile compounds in murupi peppers (Capsicum chinense Jacq.) grown in two distinct years at two stages of maturation by HS-SPME, GC-FID and GC–MS.

Compound ID LTPRICal. LTPRILit. Δ 2008 2009

Immaturea Maturea Immaturea Maturea

Alkanes
6-methyl-1-octene B 849 842 −7 0.24a 0.13b 0.21a 0.16b
(E)-7-methyl-3-octene B 851 860 9 0.50a 0.50a 0.31b 0.31b
Tetradecane A 1400 1400 0 1.38 d 3.64b 3.95a 2.63c

Alcohols
3-methyl-1-pentanol B 835 826 −9 t 0.22c 0.88a 0.66b
1-hexanol A 869 865 −4 t 0.25a 0.02c 0.14b
1-octanol A 1059 1057 −2 t 1.32 t t
4-butoxy-1-butanol B 1144 1135 −9 0.73a 0.68b t t
(E,Z)-2,6-nonadien-1-ol B 1155 1160 5 9.82a 2.41b 2.22c 1.01 d
2-decen-1-ol B 1260 1266 6 0.87b 0.59c 1.59a 0.89b
1-decanol A 1278 1272 −6 t t t t
10-undecen-1-ol B 1339 1346 7 0.33 d 0.42c 0.8b 0.94a
(E)-2-undecen-1-ol B 1362 1355 −7 2.42b 2.66a 2.59a 1.87c
2,2-dimethyl-1-decanol B 1370 1372 2 1.42 d 10.33a 6.94c 9.17b
(E)-2-dodecenol B 1445 1455 10 6.07c 6.06c 11.16b 13.55a
(E)-11-tetradecen-1-ol B 1660 1664 4 0.30bc 0.01c 0.55b 8.83a

Aldehydes
3-methyl-butanal A 650 643 −7 t t 0.15b 0.19a
Pentanal A 701 707 6 t t 0.26a 0.11b
Hexanal A 802 806 4 t t 0.51a 0.17b
(E)-2-hexenal A 852 855 3 t 0.13 t t
(Z)-2-nonenal B 1105 1112 7 t 0.16c 0.63a 0.42b
Dodecanal B 1390 1389 −1 50.14a 34.74b 26.27c 13.47 d
(Z)-2-dodecenal A 1455 1447 −8 47.12b 54.23a 11.75c 5.47 d
Tridecanal A 1502 1494 −8 10.19a 5.63b 2.67c 1.79 d
(E)-2-tridecenal B 1553 1546 −7 3.05b 6.24a 2.93b 0.67c

Esters
Hexyl ethanoate B 979 984 5 t 1.27c 3.09a 2.59b
Ter-butyl pentanoate B 1004 999 −5 t 0.69a 0.25b 0.10c
Heptyl acetate B 1085 1083 −2 t 0.22 t t
2-methylbutyl2-methylbutanoate B 1101 1095 −6 t 0.11c 1.04b 8.68a
3-methylbutyl 3-methylbutyrate B 1107 1109 2 1.19c 2.36a 1.53b 1.11c
Pentyl 3-methylbutanoate B 1111 1118 7 t t 0.48b 0.82a
Hexyl isobutyrate A 1114 1118 4 t 3.1b 21.25a 20.34a
Isononyl acetate B 1150 1151 1 t 8.09a 5.20b 3.08b
Hexyl butyrate A 1158 1155 −3 t 0.75b 1.15c 0.85a
(E)-3-hexenyl butyrate B 1191 1192 1 0.25a 0.06b t t
Methyl salicylate A 1193 1192 −1 t t 7.35a 1.3b
Hexyl 2,2-dimethylpropanoate B 1202 1197 −5 41.28b 46.58c 121.02a 53.48b
2-ethylbutyl hexanoate B 1216 1218 2 t t 1.35a 0.20b
(Z)-3-hexenyl isovalerate B 1234 1238 4 67.60a 27.33b 24.94c 7.22 d
(Z)-3-hexenyl-2-methyl butanoate B 1238 1239 1 248.18a 160.84b 123.60c 76.86 d
Hexyl 2-methylbutanoate B 1248 1243 −5 225.97a 176.12b 4.16c 4.21c
Hexyl 3-methylbutanoate B 1249 1243 −6 4.61a 2.33b 0.29c 0.24c
Heptyl isobutyrate A 1253 1248 −5 t t t t
(Z)-6-nonenyl acetate B 1295 1290 −5 10.63a 3.08 d 8.61b 6.17c
Butyl 4-methylpentyl carbonate B 1304 1294 − 10 1.77c 1.77c 2.15b 3.96a
2-methylpentyl hexanoate B 1321 1317 −4 3.79 d 14.15c 35.68b 20.5a
Allyl heptyl carbonate B 1342 1348 6 17.20a 12.88b 10.43c 5.56 d
(E)-2-hexenyl hexanoate B 1359 1369 10 7.40b 5.04 d 12.55a 6.63c
Octyl pivalate B 1405 1396 −9 7.32c 4.58 d 183.5a 168.65b
Octyl pentanoate B 1416 1417 1 21.95a 16.32b 9.92 d 13.76c
Octyl isopentanoate B 1448 1441 −7 23.60c 14.32 d 60.17a 35.24b
Allyl decanoate B 1472 1471 −1 17.56b 38.36a 0.58c 0.77c

Ether
2-pentyl-furan A 991 993 2 t t 0.29a 0.23b
Monoterpenes
α-pinene A 932 935 3 5.39a 0.71b t t
sabinene B 973 972 −1 9.32a 1.32b 0.10c 0.17c
β-pinene A 975 976 1 8.32a 1.33b t t
β -myrcene A 993 987 −6 2.69a 1.48b t t
α-phellandrene A 1005 1002 −3 2.58a 1.22b t t
δ -3-carene A 1010 1014 4 8.91a 1.97b t t
Limonene A 1027 1028 1 1.54b 1.62a 1.34c 1.51ab
(E)-β-ocimene B 1051 1046 −5 3.05a 2.33b t 0.31c
Neral A 1223 1220 −3 0.50c 0.02 d 1.47b 10.03a

(continued on next page)

106 S. Bogusz Junior et al. / Food Research International 48 (2012) 98–107

Table 3 (continued)
Compound ID LTPRICal. LTPRILit. Δ 2008 2009

Immaturea Maturea Immaturea Maturea

Sesquiterpenes
α-cubebene B 1355 1349 −6 18.42a 13.73c 14.61b 10.13 d
α-ylangene B 1376 1375 −1 0.64a 0.40b 0.37c 0.19 d
α-copaene A 1381 1375 −6 6.63b 7.34a 5.44c 5.43c
β-caryophyllene A 1424 1428 4 4.86b 2.56c 5.50a 5.68a
(E)-β-farnesene A 1435 1440 5 1.67a 1.39b 1.22c 0.70 d
α-humulene A 1460 1454 −6 1.29b 1.4a 0.46c 0.31 d
(E)-β-bergamotene B 1465 1467 2 13.16c 9.36 d 22.44a 14.32b
α-clovene B 1474 1468 −6 2.58a 1.71b 0.15c 0.28c
Germacrene-D B 1486 1480 4 159.36a 121.3b 122.34b 71.87c
β-ionone B 1488 1485 3 17.68b 15.16c 23.09a 14.32 d
Valencene B 1490 1491 1 6.17b 4.16c 14.53a 6.4b
β-himachalene A 1507 1503 −4 5.99b 8.06a 5.64c 3.74 d
β-sesquiphellandrene B 1521 1525 4 0.56b 0.64a t t
Zonarene B 1523 1527 4 1.19a 1.68b 1.80a 1.87a
ω-cadinene B 1531 1526 −5 2.88c 3.52b 3.56b 4.03a
(E)-cadina-1,4-diene B 1540 1536 −4 1.14a 1.14a 1.07a 0.88b

ID = identification by A = mass spectrum and linear retention index agreed with the standards; B = mass spectrum and linear retention index agreed with the literature data.
LTPRICalc. = retention indexes obtained using a 5% phenyl/95% dimethylpolysiloxane capillary column.
LTPRILit. = retention indexes from the literature obtained using a 5% phenyl/95% dimethylpolysiloxane capillary column.
Δ = differences between the calculated retention indexes and those from the literature; LTPRILit - LTPRI Calc.
t = trace level (area less than 0.01).
– = not detected.
Different letters in the same row indicate significant difference by Tukey test at p ≤ 0.05.
a
Peak area divided by 106, obtained by GC-FID (detector response factors equal to unity); the results are presented as the mean of triplicate experiments.

2010). Among the esters found in murupi peppers, the presence of
the group of hexyl esters 2/3methybutanoates should be highlighted,
as they are present as major compounds, these esters have been
reported as important for the fruity aroma, sweet and exotic in C. chi-
nense (Kollmannsberger et al., 2011).The greater number of esters in
the murupi pepper relative to the dedo-de-moça pepper may explain
why the aroma of murupi peppers is described as more agreeable and
fruity than that of dedo-de-moça peppers (Flament, 2002; Moya-
Léon, Vergara, Bravo, Montes, & Moggia, 2006).
The murupi peppers contained a furan ether, 2-pentyl-furan, that
was not observed in the malagueta and dedo-de-moça peppers. This
compound, which has a low aroma threshold value with buttery
and aniseed oil notes, showed greater peak areas in the second year
of harvest (Bandeira, Toci, Trugo, & Farah, 2009).
Interestingly, no ketones were found in the murupi peppers.
Short-chain ketones (C5–C11), especially the methyl ketones, are po-
tent flavour molecules and are thought to be the precursors of some
of the secondary alcohols found in fruit aromas (Strohalm, Dregus,
Wahl, & Engel, 2007).
The compounds δ-3-carene and neral were identified among the
terpenes present in the murupi peppers. The first compound was
also found in the malagueta peppers, but the second was only found
in the murupi peppers. Neral confers agreeable citrus notes, even in
small concentrations, and likely contributes to the flavour of this
type of pepper (Perez-Cacho & Rouseff, 2008). Neral was found in
malagueta peppers and δ-3-carene was detected only in murupi
peppers. Major contributions were observed for the sesquiterpenes
germacrene-D (oily, green, woody) and β-ionone (violets, floral, rasp-
berry, woody), and these data are in agreement with those found for
other varieties of C. chinense, such as farolillo pepper and cachuca pep-
per. Contribution of β-ionone was especially important for the inten-
sity and odour quality of these Capsicum peppers. (Pherobase, 2011;
Rodríguez-Burruezo et al., 2010).
4. Conclusions
In summary, 168 compounds were identified in the volatile frac-
tion of three distinct Brazilian Capsicum pepper varieties. Although
many of these compounds have been previously identified in other
vegetable species, none had been previously reported in unripe and
ripe dedo-de-moça and murupi pepper, and in ripe malagueta pepper
varieties. Characterisation of the volatiles by GC–MS revealed com-
plex chemical compositions with important differences between the
varieties, with esters predominating in the malagueta pepper, mono-
terpenes in the dedo-de-moça pepper and sesquiterpenes in the mur-
upi pepper. Furthermore, the peak areas of the volatiles in each of the
peppers investigated in this study decreased in more mature speci-
mens. The most dramatic loss of volatiles was observed for the
dedo-de-moça peppers.
Appendix A. Supplementary data
Supplementary data to this article can be found online at doi:10.
1016/j.foodres.2012.02.005.
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