J. Agric. Food Chem.

2005, 53, 1637−1641 1637

Identification of Potent Odorants in Different Cultivars of Snake

Fruit [Salacca zalacca (Gaert.) Voss] Using Gas
Chromatography−Olfactometry

C. H. WIJAYA,*,† D. ULRICH,§ R. LESTARI,# K. SCHIPPEL,§ AND G. EBERT#

Department of Food Technology and Human Nutrition, Faculty of Agricultural Engeneering and
Technology, Darmaga Campus, Bogor Agricultural University, Bogor 16002, Indonesia; Institute for
Plant Analysis, Federal Centre for Breeding Research on Cultivated Plants (BAZ),
Neuer Weg 22/23, D-06484 Quedlinburg, Germany; and Institute for Horticultural Sciences, Humboldt
University Berlin, Albrecht-Thaer-Weg 3, D-14195 Berlin, Germany

Three cultivars of snake fruits, Pondoh Hitam, Pondoh Super, and Gading, were freshly extracted
using liquid-liquid extraction. The aroma compounds of the three samples were analyzed by GC-
MS and GC-olfactometry using the nasal impact frequency (NIF) method. A total of 24 odor-active
compounds were associated with the aroma of snake fruit. Methyl 3-methylpentanoate was regarded
as the character impact odorant of typical snake fruit aroma. 2-Methylbutanoic acid, 3-methylpentanoic
acid, and an unknown odorant with very high intensity were found to be responsible for the snake
fruit’s sweaty odor. Other odorants including methyl 3-methyl-2-butenoate (overripe fruity, ethereal),
methyl 3-methyl-2-pentenoate (ethereal, strong green, woody), and 2,5-dimethyl-4-hydroxy-3[2]-
furanone (caramel, sweet, cotton candy-like) contribute to the overall aroma of snake fruit. Methyl
dihydrojasmonate and isoeugenol, which also have odor impact, were identified for the first time as
snake fruit volatiles. The main differences between the aroma of Pondoh and Gading cultivars could
be attributed to the olfactory attributes (metallic, chemical, rubbery, strong green, and woody), which
were perceived by most of the panelists in the Pondoh samples but were not detected in the Gading
samples. This work is a prerequisite for effective selection of salak genotypes with optimal aroma
profiles for high consumer acceptance.

KEYWORDS: Aroma; volatiles; gas chromatography-mass spectrometry; gas chromatography-

olfactometry; snake fruit; stir bar sorptive extraction

INTRODUCTION intensity, including overripe and sweaty impressions. Outside

Indonesia this kind of aroma is usually not preferred.
Salak [S. zalacca (Gaert.) Voss] has been known as snake As a promising export fruit commodity, cv. Pondoh is playing
fruit originally coming from Indonesia and other Southeast Asian very important roles. To enhance the fruit acceptance by devel-
countries. The fruit has been used as fresh fruit in these areas oping new accessions by breeding, it is important to characterize
for a long time. In Indonesia, there are about 30 cultivars of the aromatic profiles of the flesh of these fruits. The volatiles of
snake fruit, such as Pondoh and Bali. The popularity of snake unknown cultivars have already been reported (1) as well as the
fruit as a commercial fruit has increased significantly since the qualitative and quantitative changes in the volatile compounds
discovery of snake fruit cv. Pondoh in the 1980s, which was of the Pondoh cultivar during the maturation process (2).
planted at a village in Yogyakarta province. Today, three types To the best of our knowledge, the aroma impact compounds
of cv. Pondoh are known, including Pondoh Super and Pondoh responsible for the characteristic odor of this fruit still have not
Hitam. Another cultivar of snake fruit planted in Yogyakarta is been investigated. Therefore, the topic of the present investiga-
Gading. Snake fruit cv. Pondoh has different flesh characters tion is to identify the impact odorants of salak by mass
compared with snake fruit cv. Bali. Besides this positive attribute spectrometry (MS) and gas chromatography-olfactometry
the cultivar cv. Pondoh is characterized by the highest aroma (GC-O). In addition, the aroma profiles of the fresh flesh of
three cultivars of snake fruit are compared. This work is a
* Corresponding author (telephone 62-251-620069; fax 62-251-626725; prerequisite for effective selection of salak genotypes with
e-mail [email protected]). optimal aroma profiles for high consumer acceptance, that is,
† Bogor Agricultural University.
§ Federal Centre for Breeding Research on Cultivated Plants (BAZ). cultivars with typical fresh fruity aroma and low overripe and
# Humboldt University Berlin. sweaty attributes.
10.1021/jf048950h CCC: $30.25 © 2005 American Chemical Society
Published on Web 02/09/2005
1638 J. Agric. Food Chem., Vol. 53, No. 5, 2005 Wijaya et al.

MATERIALS AND METHODS Chemstation via an A/D converter as square signals. The six single
sniffing runs were accumulated to one coincident response chromato-
Snake Fruit Samples. Two cultivars of Pondoh snake fruits called gram, a so-called NIF profile (5), using a specially designed macro
Pondoh Super and Pondoh Hitam, and also a local cultivar called (6). The resulting NIF profile can be handled by the HP Chemstation,
Gading, at a stage of 5.5-6 months after pollination were collected for instance, to integrate peaks. Odors detected by only one or two
from the growers at Sleman, Yogyakarta. The fruits were transported judges were considered as olfactorical noise and rejected. Odor-active
by plane to Germany and were analyzed immediately after arrival. components were defined as those that were detected at identical
Overall Sensory Evaluation. The overall flavor impressions of the retention times by at least three panelists. It is known that the perception
three salak cultivars were defined by an experienced panel. After tasting and description of odor qualities is highly individualized. Therefore,
of the fresh peeled fruit flesh, the sensory impressions were fixed in after the sniffing session, an open discussion with the six panelists was
an open discussion with the six panelists with the aim of describing held with the aim of describing the odors using identical terms.
the flavor using identical terms.
Isolation of Volatiles by Liquid-Liquid Extraction. The flesh (200
RESULTS AND DISCUSSION
g) of each cultivar was homogenized for 1 min in 300 mL of NaCl
solution (18.6% w/v). The homogenate was centrifuged at 4 °C for 30 Overall Sensory Evaluation. The overall sensory description
min at 3000 rpm to give a supernatant. To obtain a clear juice, the of the fresh snake fruits was evaluated by a panel. The aroma
supernatant was filtered through filter paper. A portion (250 mL) of was characterized with the following characteristics: fruity,
the filtrate was subjected to a fluid-fluid extractor apparatus (3) after
chemical, cheesy, overripe banana-like, earthy, caramel, pleas-
the addition of an internal standard. The volatile compounds were
extracted by 30 mL of 1,1,1-trichlorofluoromethane (Freon F11) from ant, vanilla, thinner, and unpleasant. The taste impressions were
the aqueous solution for 20 h at room temperature. The Freon fraction described as chemical, unpleasant, nutty, apricot, thinner, and
was concentrated with a Vigruex column directly before analyses. astringent (especially the Gading cultivar). It seemed that salak
Isolation of Volatiles by Stir Bar Sorptive Extraction (SBSE). had an interestingly uniquee exotic flavor, especially for the
An aliquot of 10 mL of supernatant prepared as mentioned above was non-native consumer. Generally, the impression of overripe,
pipetted in a 20 mL glass headspace vial and saturated by adding 3 g cheesy, and sweaty character and astringent taste might be a
of solid NaCl. A stir bar (0.5 mm film thickness, 10 mm length; Gerstel constraint for the acceptability of snake fruit, especially for
GmbH, Mühlheim an der Ruhr, Germany) coated with PDMS was used. European consumers. Therefore, salak genotypes with a light
The stir bar was placed in the 20 mL vial. The vial was sealed with a fruity, pleasant aroma in combination with low astringent taste
crimp cap and stirred at 300 rpm at room temperature for 45 min. After should have best preference.
removal from the sample, the stir bar was rinsed with distilled water,
dried with a tissue, and transferred in a glass thermal desorption tube
Identification of Aroma-Active Compounds. Constituents
for GC-MS analysis. of the snake fruit extracts that could be identified by the GC-
Gas Chromatography-Mass Spectrometry. For liquid samples a MS were in agreement with the published ones (1, 2). The
Hewlett-Packard GC-MS system (GC 5890 plus and MSD 5972) chromatograms of Freon extracts are very detailed and contain
equipped with a split-splitless injector at 250 °C was used. SBSE was more than 100 discrete peaks. The components were dominated
carried out with a system from Gerstel GmbH. The GC-MS was by the carboxylic acids and their methyl esters. Methyl
equipped with a Gerstel TDU and CIS4. Thermal desorption and cold 3-methylpentanoate, methyl 3-methyl-2-pentenoate, methyl
injection were carried out under typical SBSE conditions described in 3-hydroxy-3-methylbutanoate, 2-methylbutanoic acid, and 3-
ref 4. The MS detector temperature was 280 °C. A polar column (HP methylpentanoic acid were found as the major components. The
INNOWax, 0.25 mm i.d. × 30 m length × 0.5 µm film thickness) was other esters that were abundantly detected included methyl
used with the following temperature program: 45 °C held for 5 min,
3-methyl-2-butenoate, methyl 3-hydroxy-3-methyl pentanoate,
then raised to 200 °C at a rate of 2 °C/min, and held for 30 min. The
flow rate of the carrier gas (He) was 1.0 mL/min. A volume of 1 µL
methyl hexanoate, and methyl 3-hydroxy-3-methylbutanoate.
of each sample was injected with the split ratio of 1:3 and 1:50, The last two, however, were found only in smaller amounts in
respectively. For compound identification the Wiley and NIST libraries Gading cultivar. Some alcohols, furanones, and aldehydes also
were used. could be found among the identified compounds. Some terpenes,
Gas Chromatography-Olfactometry. Instrument and Operation. although in small amount, could also be detected using SBSE
The sniffing sessions were conducted in an air-conditioned room (22 sample preparation. One big and one medium peak remained
°C). A Hewlett-Packard GC 6890 series II gas chromatograph equipped unknown. Pondoh Super and Pondoh Hitam showed similar
with a polar fused silica column (HP INNOWax, 0.25 mm i.d. × 15 m patterns in their chromatograms. The Gading cultivar had slight
length × 1.0 µm film thickness) was used with split injection. Both differences, especially for the ratio of several components.
injector and FID temperatures were at 250 °C. The oven program was Figure 1 shows the NIF profile (top) versus the FID gas
the following for all runs: 45 °C for 5 min, then raised to 210 °C at a
chromatogram (bottom, inverted) of a snake fruit extract. The
rate of 10 °C/min, and finally held for 5 min. Each sniffing run
continued for 25 min. Hydrogen was used as the carrier gas at a flow importance of the olfactometric analysis in the study of the
rate of 1 mL/min. A volume of 1 µL of snake fruit extract was injected aromatic profile again was proved here (7, 8). Some evidence
at a split flow of 5 mL/min. The column outlet was connected either showed that minor compounds might be able to play an
with the FID via transfer line (monitor run) or with the sniffing port important role in influencing the flavor. Many of the major
equipped with a heated transfer line of identical length and a glass compounds such as methyl 3-hydroxy-3-butanoate, methyl
funnel. The complete sniffing session for one variety consists of two hexanoate, methyl 3-methylhydroxypentanoate, or the large
FID analyses, one with a boiling point sample for calculation of unknown peak produced little to no olfactory responses. On the
retention indices and one monitor run with the salak extract for retention other hand, some of the intense olfactory responses were found
time adjustment to the GC-MS run of the same extract. After the column in regions with little FID signals, that is, peaks 1, 3, 6, 17, 18,
outlet had been switched to the sniffing port, six separate runs followed,
and 20 and some others. As shown on the mirrored signal
carried out by six trained panelists.
between the FID and olfactory response (Figure 1), this
Data Processing. To determine potentially odor-active compounds
of the snake fruit extracts, the nasal impact frequency (NIF) method technique even allowed the detection of components that were
(5) was performed with modifications (6). Panelists recorded the unable to be detected by the FID. For example, peak 8, with
perception of an odor by pressing a button as long as the smell could cooked potato aroma description, usually corresponded to the
be received. Moreover, each panelist was encouraged to describe the presence of methional. No peak in the FID chromatogram
odor quality of each perception. The signals were registered by the HP correlated with this compound. This phenomenon has been
Snake Fruit GCO J. Agric. Food Chem., Vol. 53, No. 5, 2005 1639

Hitam cultivar, possibly due to its higher threshold compared

to the existing amount.
Cheesy, sweaty, stinky wet cloth or socky, overripe fruit, and
sour butter categories were the predominant characters in these
results. 2-Methylbutanoic acid (13, 14) and 3-methylpentanoic
acid were two of the more intense aroma compounds active in
all cultivars, which might be responsible for this kind of
character. Together with 3-hexenoic acid and presumably
another carboxylic acid with a longer chain (higher boiling
point), they are responsible for the unpleasant aroma of the snake
fruit claimed as sweaty odor already by Suprijadi et al. (2). The
lack of corresponding flavor notes of 3-methylpentanoic acid,
which has been reported as herbaceous (11), remains as a
question. It is possible that the accompanying peak, 3-methyl-
2-butenoic acid, was also responsible for the observed olfactory
responses. In the future, reducing this category of aroma should
be a challenge in improving the acceptability of snake fruit.
Caramel, sweet, warm, and burnt characters were also well-
detected aroma categories. The presence of 4-hydroxy-2,5-
Figure 1. Comparison of NIF profile and FID chromatogram (monitor run)
dimethyl-3(2H)-furanone (Furaneol), although this component
of salak cv. Pondoh Hitam (S1). Compound numbers refer to Table 1.
has been detected only as a small peak by FID detection,
provided a strong cotton candy aroma (9, 14-16). The other
previously reported (7). Because methional has a very low compound that should be responsible for this aroma impression
olfactory threshold of 0.2 ng/L in water (7), it might be was 4,5-dimethyldihydro-2(3H)-furanone. This compound has
recognized by the panelists even in very low concentration. This been described as warm, woody, smoke, burnt caramel, and
small olfactory active peak might be beneath the large methyl sharp spicy.
3-hydroxy-3-methylbutanoate peak. The GC-MS spectrum
Furthermore, it is interesting to note that almost all panelists
indicated that this large nearest peak has more than one
detected a specific strong aroma like lovage (very similar to
compound.
the well-known liquid seasoning produced by Maggi Corp.).
A similar effect occurred at the high boiling point area, such
This compound has been suspected as an artifact, but it has
as peaks 23 and 24, which have strong olfactory intensity but
been proven by blank runs that the origin is the fruit homoge-
do not correlate with any peaks. In the case of peaks 21 and
nate. It seems likely that methyl anthranilate corresponds to this
22, the compounds are tentatively identified by using the result
olfactory impact. The presence of this compound in fruit is not
of SBSE as well as the aroma description in comparison with
surprising (12). The reported odor description of this compound,
the previously reported data (9-11). The SBSE was used in
however, which is described as fruity, grape (10), or foxy (9),
parallel with the liquid extraction for MS identification. In
prevents a positive identification.
general, chromatograms after SBSE give similar results but with
more detailed chromatograms in the region of high retention Also, the olfactory peak 3 was identified tentatively. This
times. Therefore, it was possible to identify the substances peak corresponded well with a compound identified as methyl
methyl dihydrojasmonate (21) and isoeugenol (22) in SBSE pentanoate. However, on the basis of the olfactory perception
extracts but not in liquid extracts. (10) such as metallic, chemical, rubber, and strong green, these
The result of GC-O is summarized in Table 1. The unique characters are more likely to come from the smaller peak, (E)-
flavor of snake fruit might be due to these various characters 2-methyl-2-butenal.
of olfactory responses. The responses were varied from pleasant Flowery was also important in the whole aroma composition
notes, such as flowery, fruity, and sweet caramel, to unpleasant of snake fruits. There are two types of flowery: one is perfumery
note, such as cheesy, stinky wet cloth, and sweaty, and also flowery, as shown by peak 21 (methyl dihydrojasmonate), and
light flavor notes including green, fresh, and cooked potato as the other is heavy flowery (stinky flowery), like the olfactory
well as heavy ones such as overripe, warm, spicy, pungent, and response at peaks 12 and 24. The existence of sulfur compounds
woody. such as tetrahydro-2-methylthiophene (peak 12) in this fruit
Methyl 3-methylpentanoate (fruity, sweet, typical snake fruit) should contribute to its specific characteristic flavor. There
was found to be the compound that is responsible for the snake were also mixed notes of flowery, spicy, and smoke (tobacco)
fruit flavor because most of panelists were able to recognize it aroma that are probably due to the presence of isoeugenol (12).
with a similar impression, “typical salak”. This compound has The presence of these compounds has not been reported before
been also reported by Supriyadi et al. (2) as having snake fruit (1, 2).
character odor quality. The other compound, methyl 3-methyl- It should be noted that some peaks are still unknown. As
2-pentenoate, which was reported also as having snake fruit mentioned before, the cheesy sweaty odor was very intense
character (2), could also be detected by most of the panelists, during the GC-O measurement. Because it had a longer after-
although its role as a fruit character odorant seems to be odor, it may be covering the olfactory response of the other
questionable because unspecific aroma descriptors (woody, surrounding compounds. The presence of a large number of
solvent-like or chemical, strong green, stale/spoilage) were methyl esters of C5 and C6 branched-chain alkanoic, alkenoic,
obtained. Another olfactory peak that contributes to typical snake and hydroxyalkanoic acids with their isomers (1, 2) is another
fruit aroma might be methyl 3-methylbutanoate, which has been challenge to obtaining all of the olfactometry descriptions. In
described as snake fruit-like and cheesy typical snake fruit (12). fact, this phenomenon is rarely found even in some tropical
It was clearly recognizable in the Pondoh Super cultivar but fruits reported previously (8, 17-19). Most of the unknown
not in the Gading cultivar and almost undetected in the Pondoh compounds are present at low concentrations but have high odor
1640 J. Agric. Food Chem., Vol. 53, No. 5, 2005 Wijaya et al.

Table 1. Results of GCO Analyses

NIF cultivara
no. RTb (min) RIc compound odor description identd S1 S3 S4
1 3.25 1011 methyl 2-methylbutanoate fruity, fresh 1, 2, 3 5 4 4
2 3.46 1020 methyl 3-methylbutanoate cheesy, snake-fruit like 1, 3 1 4 nd
3 4.63 1085 2-methyl-2-butenal metallic, rubbery, green 1, 3 5 5 nd
4 5.34 1127 methyl 3-methylpentanoate fruity, sweet, typical snake-fruit 1, 2, 3 5 5 6
5 6.16 1184 methyl 3-methyl-2-butenoate overripe fruit, fruity, green/ethereal 1, 3 5 5 6
6 6.66 1209 unknown pyrazine, metallic, chemical, woody, strong green 4 5 nd
7 7.63 1262 methyl 3-methyl-2-pentenoate ethereal, woody, strong green, spoilaged 1, 2, 3 5 6 5
8 10.24 1463 methional cooked potato 2 4 5 4
9 10.59 1478 unknown ester (m/z 41, 55, 87) fruity, sweet, typical snake-fruit (weak) 1 3 2 3
10 12.13 1591 4,5-dimethyldihydro-2(3H)-furanone warm, woody, burnt caramel, sharp spicy 1, 2 3 5 4
11 12.78−13.24 1658 2-methylbutanoic acid cheesy, unpleasant overripe, sweaty, sour, buttery 1, 2, 3 5 6 6
12 13.75 1741 tetrahydro-2-methyl thiophene stinky flowery, almond, stale 1 5 6 3
13 14.16 1780 3-methylpentanoic acid, 3-methyl- unpleasant riped cheese, rancid, pungent 1, 3 5 5 6
2-butenoic acid
14 14.80−14.93 1835 2-methyl-2-butenoic acid marzipan, unpleasant 1, 2, 3 3 3 1
15 15.28−15.36 1890 phenylethyl alcohol flowery, floral, drop acid (honey), fragrant 1, 2, 3 3 3 nd
16 15.54 1909 (E)-3-hexenoic acid stinky wet cloth, sharp pungent, vinegar, sweaty 1, 2, 3 3 5 4
17 16.54 2020 2,5-dimethyl-4-hydroxy-3(2H)-furanone caramel, sweet, cotton candy 1, 2, 3 4 5 4
18 17.29 2113 unknown chemical, burnt 3 1 3
19 17.71 2215 unknown spicy, clove, Christmas cake nd 2 4
20 18.04 2226 methyl anthranilate strong, lovage, celery leaves, “Maggi” 1, 2, 3 6 5 3
21 18.38 2276 methyl dihydrojasmonate flowery, perfumery 2, 4 2 3 3
22 19.27 2378 isoeugenol spicy, cooked meals, smoky 2, 4 3 3 5
23 21.54 >2600 unknown vanilla-like 3 2 nd
24 21.67 >2600 unknown stinky flowery, silage 5 5 5

a Salak cultivars: S1, cv. Pondoh Hitam; S2, cv. Pondoh Super; S3, cv. Pondoh Gading. nd, not detected. b Retention time at GC-O. c Retention index. d Substance
identification: 1, MS library search; 2, aroma descriptors; 3, reference data; 4, SBSE-MS and library search.

impacts (extremely low odor thresholds). The unknown sub-

stance at peak 6 in Figure 1 is eluted on the wax column in
front of an ester peak (methyl 3-hexenoate). The sensory
description as pyrazin-like, metallic, chemical, and green refer
to a compound of the pyrazine group. Unknown 12 appears as
a defined peak with the following mass fragmentation (m/z and
intensity): 29 (35%), 41 (52%), 43 (38%), 55 (46%), 87 (100%),
115 (7%). Identification by library search was not successful.
The four unknown compounds 18, 19, 23, and 24 belong to
odor impressions that appear in chromatogram regions with no
defined peaks. Therefore, an expedient mass fragmentation is
not available. Further detailed studies regarding substance
identification should be carried out.
Aroma Differences among Cultivars. The NIF profiles of
the three cultivars are shown in Figure 2. Pondoh cultivars,
consisting of Pondoh Hitam and Pondoh Super, have similar
profiles. The Gading cultivar gave a cleaner chromatogram
compared to the other two. The Pondoh cultivars revealed more
crowded chromatograms, especially at the lower impact re-
sponse. The main differences between the aroma of Pondoh and Figure 2. NIF profiles of three different salak cultivars. Smell responses
Gading cultivars could be attributed to the peaks 2, 3, 6, 15, with a nasal impact below NIF ) 2 were excluded (olfactory noise). Salak
and 23, which were perceived by almost of the panelists in the cultivars: S1, cv. Pondoh Hitam; S2, cv. Pondoh Super; S3, cv. Pondoh
Pondoh samples but were not detected in the Gading sample. Gading. Compound numbers refer to Table 1.
According to the olfactory results, they contributed metallic, In summary, the significant aroma of snake fruit is not the
chemical, rubber-like, strong green, woody, flowery, and vanilla- result of one odor impression. Numerous potent odorants are
like characters to the Pondoh cultivars. responsible for the overall flavor impression (18). The results,
The main differences between the Pondoh cultivars are compared with those obtained by instrumental analysis, con-
showen by the presence of peak 2, which contributes to the tribute to our present knowledge of the aroma composition in
salak typical character. This olfactory response could be detected snake fruits.
clearly by panelists in Pondoh Super but not in Pondoh Hitam. More effort should be aimed at the characterization of
This response also has not been detected at all in the Gading unidentified compounds by using different stationary phases and
cultivar. The obtained response is related to methyl 2-meth- preparative separation to improve their ability to be detected
ylbutanoate. Higher availability of this compound in Pondoh by GC-MS. This could lead to identification of compounds with
Super might be related to the stronger snake fruit specific extremely low detection thresholds that could not be detected
character of this cultivar. in this study. Nevertheless, the obtained knowledge will permit
Snake Fruit GCO J. Agric. Food Chem., Vol. 53, No. 5, 2005 1641

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