Journal of Cereal Science 99 (2021) 103178

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Journal of Cereal Science

journal homepage: http://www.elsevier.com/locate/jcs

Analysis of the key aroma volatile compounds in rice bran during storage
and processing via HS-SPME GC/MS
Chen Gao 1, Yan Li 1, Qifeng Pan , Mingcong Fan , Li Wang , Haifeng Qian *
State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, Wuxi, 214122, China

A R T I C L E I N F O A B S T R A C T

Keywords: Rice bran is one of the most valuable nutritional byproducts of rice milling. It is known to have an unacceptable
Rice bran flavor to consumers, so the development of reliable analytical methods to determine its unpleasant volatile
Volatile flavor compounds compounds should be developed. Comparative volatile profiling of rice bran at different times of accelerated
HS-SPME GC/MS
storage was performed using solid-phase microextraction (SPME) coupled to GC/MS, and the impact of stabi­
Stabilizing methods
Electronic nose
lizing methods on the odor of rice bran was evaluated using E-nose, GC/MS and gas chromatography-
olfactometry (GC-O) analyses. Sixty-five volatile compounds were identified and classified into six groups.
Among them, the relative concentration of aldehydes increased with storage time, and hexanal was the com­
pound with the highest content. Similar behavior was exhibited by ketones and alcohols, which were connected
with early oxidation of rice bran. The main characteristic odor compounds of rice bran were vanillin, 2-methoxy-
4-vinylphenol and 5-amino-2-methoxyphenol regarding ferulic acid. Through PCA, the volatile compounds of six
kinds of rice bran were distinguished. The GC-O experiment verified that the processed products changed from
the original grassy, oily flavor to vanilla, cheese, and caramel flavors. These results comprehensively elucidate
the flavor characteristics of rice bran and provide important theoretical support for the development of rice bran
products.

1. Introduction
Rice bran, a byproduct of rice milling, is a very nutritional agricul­
tural product material with great development potential (Chen et al.,
2019). This product is rich in nutrients and bioactive components such
as dietary fiber, hypoallergenic protein, phytic acid, and poly­
saccharides (Zhang et al., 2019). It is well known that rice bran inter­
vention plays a significant role in reducing dyslipidemia, alleviating
inflammation and modulating the gut microbiota for the prevention and
control of obesity (Yucheng et al., 2020). However, the harsh taste and
undesirable flavor of rice bran make it difficult to consume. Therefore,
rice bran has been mainly used for animal feed due to its unwelcome
sensory characteristics.
Of all organoleptic properties of rice bran, odor is an important
aspect contributing to its low acceptability. The flavors of cereal prod­
ucts are complex and varied, the grain quality of which plays an
important role and determines consumer acceptance. Previous studies
have reported the contribution of aldehydes, ketones and hydrocarbons
to the existence of grain flavor. For example, C8–C9 unsaturated
aldehydes and ketones contribute raw oat grain, hay-feed, and grassy
aromas (McGorrin, 2019). Aldehydes were the dominant volatile con­
stituents of raw millet, followed by hydrocarbons (Bi et al., 2019).
However, there is little information regarding the flavor chemistry of
rice bran. Maomao Zeng et al. (2012) found that the main constituents of
volatile compounds from rice bran were esters, alkanes, alcohols, ke­
tones, aldehydes, and acids, among which aldehydes and acids
contribute to the unwelcome odor, and 1-octen-3-ol, benzaldehyde,
1-octanol, and naphthalene may be the odor-active compounds. Wei Yan
et al. (2020) also found that the aroma of fresh rice bran was acceptably
preserved with abundant amounts of aldehydes and alkanes. Moreover,
no investigations have been carried out on the volatile compound profile
of rice bran during storage.
In fact, the production of off aromas of grain is associated with
rancidity caused by lipid oxidation. Free fatty acids such as oleic acid
and linoleic acid are formed by the degradation of triglycerides by lipase
and lipoxygenase in grains (Franklin et al., 2017). These species undergo
a series of reactions with the participation of active oxygen species, and
at last, relatively unreactive volatile compounds are changed into

* Corresponding author.
E-mail address: qianhaifeng@jiangnan.edu.cn (H. Qian).
1
These authors contributed equally to this work.

https://doi.org/10.1016/j.jcs.2021.103178
Received 4 November 2020; Received in revised form 17 January 2021; Accepted 24 January 2021
Available online 28 January 2021
0733-5210/© 2021 Elsevier Ltd. All rights reserved.
C. Gao et al.
hydrocarbons, aldehydes, and ketones, leading to the unpleasant odor of
rice bran (Gam et al., 2018). Thus, one would expect that we can inhibit
the production of unwelcome odors by inhibiting enzyme activity.
Additionally, the formation of numerous additional volatile substances
that give grain products a unique flavor is promoted through the Mail­
lard reaction and via lipid oxidation during the heating process. In other
words, lipid degradation produces aldehydes and ketones that interact
with the Maillard reaction products, such as amino acids and reducing
sugars, during heat treatment (Wei et al., 2020). For instance, pyrazines,
which provide a roasted and nutty flavor to products, are reported to be
derived from the Maillard reaction between amino acids and carbohy­
drates (Bi et al., 2019). Moreover, the thermal degradation of sugars
such as fructose and glucose produces furans (e.g., furfural) (Lee et al.,
2014). To date, a variety of effective methods have been developed for
stabilizing rice bran, including extrusion cooking, microwave heating,
steaming, and oven drying (Yu et al., 2020). As the volatile profile of
isolates from stabilized rice bran has not been reported, further research
is required to better understand the changes of volatile compounds in
rice bran. Moreover, the role of odor-active compounds generated by
cooking in the sensory aspects of products manufactured from rice bran
has not been fully explored. Thus, further studies that elucidate the
relationship between the pretreatment processes and the flavor com­
pounds from rice bran are needed to facilitate a more complete utili­
zation of byproducts from grain processing.
Therefore, in this study, we combined three flavor detection tech­
niques (electronic nose, GC-MS, GC-O-MS) to obtain a better under­
standing of the odor-active compounds in rice bran samples. We
observed changes in volatile composition during short-term accelerated
storage and identified several odor-active characteristic compounds of
rice bran. Then, we determined the effect of different processing
methods on the volatile composition of rice bran and identified the role
of odor-active compounds in the sensory aspects of different rice bran
sample. We wanted to monitor the unpleasant odor rice bran and
potentially improve its odor to increase its acceptability. Our research
lays a foundation for the improving the consumption acceptability of
rice bran.
2. Experimental
2.1. Chemicals
The authentic standards for analysis, n-alkane standard was pur­
chased from Sigma-Aldrich (St. Louis, MO). The internal standards (2, 3,
5-Trimethylpyrazine) was purchased from J&K Chemicals; (Beijing,
China).
2.2. Rice bran samples preparation
Freshly prepared rice bran was obtained from a local rice processing
plant in Heilongjiang Province, China. After natural drying, all samples
were collected and stored at 4 ◦ C. Milled rice bran samples were stored
at 37 ◦ C and 75% relative humidity under atmospheric pressure in
sealed polyethylene bags for accelerated shelf-life tests.
ERB meant extruded rice bran. ERB, of which the feed moisture was
conditioned to 25 g/100g, was extruded in the condition that the
different barrel zones were set at 70, 90, 110 and 130 ◦ C, respectively,
with screw speed set at 300 rpm. The extrudates were cooled to room
temperature and then milled to powders as described afterwards. MRB
pointed to microwaved rice bran. MRB with a moisture content of 24%
was spread to a depth of 0.5 cm and performed in a microwave oven at
800w for 75s. DRB was an abbreviation of dry-heated rice bran. DRB was
roasted at 130 ◦ C for 2 h in an air oven. SRB and HRB referred to steamed
rice bran and high-pressure steamed rice bran respectively. SRB was laid
on the gauze and put into steamer for 30 min when the water was
boiling. Finally, it was dried at room temperature. HRB were steamed in
a sterilizer at 121 ◦ C, 0.1 MPa (gauge pressure) under high pressure for
2
Journal of Cereal Science 99 (2021) 103178
10 min. All samples were dried to make moisture content below 10%
and approximately 100 g of each sample were grinded using an attrition
mill. Ultimately, they were placed in a ziplock bag at 4 ◦ C and removed
periodically for sampling.
2.3. HS-SPME/GC–MS analysis
Two grams (±0.1 g) of all samples were sealed in a 20 mL headspace
vial and incubated dry in an agitator at 70 ◦ C for 5 min. Volatile com­
pounds were extracted with a SPME fiber coated with divinylbenzene/
carboxen/polydimethylsiloxane (DVB/CAR/PDMS, 50/30 μm). The
SPME sampling was performed by exposing the fibers at extraction
temperature 50 ◦ C in the headspace of the vial for 40 min under
continuous stirring, 250 rpm. After sampling, the SPME devices were
subjected to analyze on a GC-MS/MS instrument (TSQ Quantum XLS).
Following extraction, the SPME fiber was injected into the GC inlet
(250 ◦ C). The volatile compounds were desorbed at 250 ◦ C for 5 min in
splitless mode.
Volatiles of rice bran were analyzed on a gas chromatography
apparatus (TSQ Quantum XLS, Thermo Fisher Scientific, USA). A DB-
Wax capillary column (30 m × 0.25 mm × 0.25 μm film thickness;
Agilent Technologies) was used with a mass detector (TSQ Quantum
XLS). The temperature for injector and detector was set at 250 ◦ C. The
programed sequence for column was set as: the initial temperature of
40 ◦ C held for 2 min and increased at 2 ◦ C/min to 120 ◦ C; then increased
to 150 ◦ C at 5 ◦ C/min. From this point, the temperature increased at
10 ◦ C/min to 230 ◦ C, and was held for 3 min. The flow rate was 1.0 mL/
min of helium (99.999%). The mass detector was equipped and set at the
following conditions for mass spectrum collection: in the electron
impact mode at an ionization voltage of 70 eV in the 33–400 m/z scan
range; the ion source temperature was 230 ◦ C.
2.4. Identification and relative quantification of volatiles
Volatiles were identified by comparing their mass spectra and
retention time with those of authentic standard compounds. Volatiles
without authentic standards were tentatively identified by searching
NIST 08 mass spectral libraries with <80% match score used as a cut-off,
and/or by comparing the Kovats’ retention index (RI). The KIs were
calculated from the retention times of C7–C40 n-alkanes. The calculation
equation of RI was as follows:
RI(X) = [(log tR(x) − log tR(z) ) ÷ (log tR(z+1) − log tR(z) ) + Z] × 100
where tR(x), tR(z), and tR(Z+1) are the retention time of the unknown
compound x and the n-alkanes with the carbon atom numbers of Z and Z
+ 1, respectively; the compound x is eluted after the n-alkane with Z
carbon atoms and before the n-alkane with Z + 1 carbon atoms.
Volatile concentrations were calculated as described previously by
Baek(Baek and Cadwallader, 1996). Briefly, the unique extracted ion
peak area of each compound was divided by the peak area of the
extracted ion peak area of an internal standard (2,3,5-Trimethylpyrazine
for nitrogen-containing compounds). The area ratio was converted to
relative concentration of the appropriate internal standard by multi­
plying by 10 ng IS/g rice bran. Concentration was calculated using the
following equation:
extracted ion peak area
Concentration(ng / g) = [I.S. × 10ng / g]
extracted ion peak area of I.S.
2.5. Electronic nose analysis
UFGC-E-nose analysis was performed following the previous study
with minor modification (Li et al., 2020). Flavor compounds were
extracted from 2.0 g of each bran sample in a 20-mL solid-phase
microextraction vial (PDMS/DVB; Supelco Company, Bellefonte, PA,
USA) at 80 ◦ C for 20 min using a controlled thermostatic agitator
C. Gao et al. Journal of Cereal Science 99 (2021) 103178

Table 1
Average Values (mean ± relative standard deviation) (μg kg− 1) of identified and semi-quantified by HS-SPME-GC/MS among all rice bran.
No. Volatile compound (ng/g) unknown literature 0d 7d 14d Identification Odor description
RI RI methods

Aldehydes

1 hexanal 1085 1083 508.2 ± 707.0 ± 1016.7 ± RI, MS, RS, odor grass, green
6.0c 15.4b 65.4a
2 heptanal 1188 1186 25.7 ± 34.0 ± 49.5 ± 1.5a RI, MS, RS fat, citrus, rancid
0.8c 1.7b
3 octanal 1287 1286 33.4 ± 53.6 ± 48.7 ± 1.1a RI, MS, RS, odor lemon, green, fat
1.7b 4.7a
4 nonanal 1389 1392 150.1 ± 190.5 ± 334.2 ± RI, MS, RS green, fat, citrus
1.0c 1.0b 5.6a
5 (Z)-2-heptenal 1321 1320 31.9 ± 41.1 ± 77.9 ± 5.1a RI, MS, RS, odor fatty
2.8b 6.2b
6 (E)-2-octenal 1424 1424 76.9 ± 97.5 ± 141.0 ± RI, MS, RS green, nut, fat
1.7c 3.9b 11.9a
7 (E)-2-nonenal 1528 1530 15.8 ± 14.4 ± 42.0 ± 3.7a RI, MS, RS, odor woody, fatty
1.6b 1.4b
8 2,4-decadienal 1803 1805 17.2 ± 5.9 ± 0.3c 22.5 ± 2.4a RI, MS, RS, odor fried, fat, wax
1.0b
10 3-methyl-butanal 938 939 43.3 ± 35.2 ± 23.4 ± 5.4c RI, MS, RS, odor malt
1.6a 4.0b
11 vanillin 2578 2578 ND 25.0 ± 50.8 ± 9.4a RI, MS, RS, odor sweet,vanilla, creamy,chocolate
1.1b
12 pentanal 1005 1004 16.2 ± 34.9 ± 56.1 ± 4.2a RI, MS, RS, odor almond, malt, pungent
0.7c 7.4b
13 (E,E)-2,4-heptadienal 1490 1488 ND 50.4 ± 120.4 ± RI, MS, RS green, floral, nut
6.0b 19.8a
14 (E,E)-2,4-nonadienal 1693 1691 10.9 ± ND 17.9 ± 5.2a RI, MS, RS, odor waxy
0.8b
15 (E)-2-hexenal 1217 1215 ND ND 22.6 ± 3.2a RI, MS, RS
16 furfural 1464 1462 124.1 ± 86.6 ± 90.1 ± 0.2b RI, MS, RS, odor bread, almond, sweet
2.5a 3.0b
Ketones
17 6-methyl-5-hepten-2-one 1336 1339 74.0 ± 92.2 ± 67.2 ± 7.5b RI, MS, RS, odor citrus
2.5b 3.7a
18 3,5-octadien-2-one 1516 1516 425.2 ± 362.3 ± 458.6 ± RI, MS, RS, odor fruity, fatty, mushroom
4.2b 11.7c 13.3a
19 3-octen-2-one 1413 1412 40.9 ± 48.5 ± 52.6 ± 4.8a RI, MS, RS, odor berry, nutty, fruity
1.9b 1.4a
20 6,10-dimethyl-(E)-5,9- 1864 18665 16.9 ± 3.1 ± 0.4c 30.7 ± 1.6a RI, MS, RS, odor
undecadien-2-one 1.2b
21 5,5-dimethyl-2(5H)- 1595 1590 16.1 ± 22.5 ± 29.4 ± 3.5a RI, MS, RS
furanone 3.0b 3.1b
22 dihydro-5-pentyl-2(3H)- 2015 2015 7.0 ± 0.2b 3.6 ± 0.2c 13.4 ± 1.1a RI, MS, RS
furanone
23 5-ethyl-2(5H)-furanone 1741 1755 8.7 ± 0.2c 12.8 ± 16.9 ± 1.1a RI, MS, RS, odor
0.7b
24 5-ethyldihydro-2(3H)- 1680 1679 18.0 ± 26.8 ± 32.1 ± 1.7a RI, MS, RS
furanone 1.7c 0.9b
25 1-(1-cyclohexen-1-yl)- 1586 ND ND 21.3 ± 3.6a RI, MS, RS
ethanone
26 2,6,6-trimethyl-2- 1642 1677 21.7 ± 29.6 ± 32.7 ± 3.2a RI, MS, RS musty, woody, tobacco, leafy
cyclohexene-1,4-dione 1.6b 1.3a
Alcohols
27 1-pentanol 1258 1254 83.4 ± 136.9 ± 142.5 ± RI, MS, RS, odor green
1.5b 6.7a 6.0a
28 1-octanol 1563 1566 41.0 ± 70.0 ± 122.1 ± RI, MS, RS, odor fatty, citrus
3.0c 2.3b 15.3a
29 levomenthol 1620 1626 10.4 ± ND ND RI, MS, RS
1.6a
30 (Z)-2-octen-1-ol 1610 1612 16.2 ± 24.1 ± 45.0 ± 6.8a RI, MS, RS green, citrus, vegetable, fatty
1.7b 0.8b
31 1-octen-3-ol 1455 1456 26.6 ± 87.6 ± 133.3 ± RI, MS, RS, odor raw mushroom
3.5c 1.5b 22.7a
32 1-penten-3-ol 1164 1164 ND ND 14.8 ± 1.5a RI, MS, RS
33 2-ethyl-1-hexanol 1488 1488 30.7 ± 44.8 ± 131.2 ± RI, MS, RS
1.6b 3.7b 21.7a
34 2,3-butanediol 1581 1580 ND ND 11.7 ± 0.8a RI, MS, RS fruity, creamy, buttery
35 2-furanmethanol 1635 1635 19.2 ± 30.2 ± 34.9 ± 2.7a RI, MS, RS
1.5c 1.1b
Hydrocarbons
36 dodecane 1197 84.5 ± 114.0 ± 111.9 ± RI, MS, RS, odor alkane
2.5b 9.7a 13.2a
37 tridecane 1298 343.8 ± 330.6 ± 278.2 ± RI, MS, RS
13.1a 2.0a 33.0b
(continued on next page)

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C. Gao et al. Journal of Cereal Science 99 (2021) 103178

Table 1 (continued )
No. Volatile compound (ng/g) unknown literature 0d 7d 14d Identification Odor description
RI RI methods

Aldehydes

38 tetradecane 1398 1400 577.6 ± 409.3 ± 632.5 ± RI, MS, RS, odor alkane
15.7b 25.5c 25.7a
39 pentadecane 1498 85.7 ± 68.9 ± 135.0 ± RI, MS, RS, odor waxy
2.2b 7.7b 20.5a
40 3-methyl-tridecane 1367 1366 62.4 ± 58.5 ± 61.5 ± 0.4a RI, MS, RS
1.6a 1.9b
41 2,2,4,6,6-pentamethyl- 974 950 204.1 ± 169.2 ± 58.7 ± 1.8c RI, MS, RS
heptane 3.7a 2.9b
42 2,6,10-trimethyl-dodecane 1355 202.1 ± 183.4 ± 267.7 ± RI, MS, RS
4.4b 8.4b 26.1a
Others
43 2-pentyl-furan 1232 1230 57.5 ± 94.9 ± 71.9 ± 13.4 RI, MS, RS, odor nutty, beany, buttery
3.5b 17.8a ab
44 benzaldehyde 1512 1513 24.5 ± 18.4 ± 25.9 ± 1.6a RI, MS, RS, odor nutty, bitter
2.0a 0.4b
45 2-pyrrolidinone 2135 2020 1.6 ± 0.1b 2.1 ± 0.2b 4.2 ± 0.3a RI, MS, RS
46 caprolactam 2281 4.5 ± 1.3a ND ND RI, MS, RS
47 limonene 1191 1190 69.0 ± 41.1 ± ND RI, MS, RS lemon, orange
1.8a 1.0b
48 5-amino-2-methoxyphenol 2263 12.3 ± 17.6 ± 23.2 ± 2.4a RI, MS, RS, odor dung, stable
1.4c 0.9b
49 2-Methoxy-4-vinylphenol 2194 2194 5.0 ± 0.1b 3.1 ± 0.4c 9.5 ± 0.8a RI, MS, RS, odor dry, woody, fresh, roasted
50 pantolactone 2024 2033 9.5 ± 0.5c 20.2 ± 29.6 ± 1.3a RI, MS, RS cotton candy
0.3b
51 o-xylene 1168 1169 4.2 ± 0.5b 7.6 ± 1.7a ND RI, MS, RS
52 benzyl alcohol 1872 1870 21.4 ± 39.2 ± 50.1 ± 2.6a RI, MS, RS slightly sweet
1.0c 2.8b
53 phenol 1999 1994 3.5 ± 0.2b 5.9 ± 0.0 8.2 ± 2.3a RI, MS, RS sweet, medicinal
ab
54 n-caproic acid vinyl ester 1627 ND 19.4 ± 24.7 ± 4.0a RI, MS, RS
0.5b
55 1H-pyrrole-2- 2009 2009 ND ND 7.3 ± 1.4a RI, MS, RS
carboxaldehyde
56 2,3-dihydro-benzofuran 2392 90.8 ± 74.4 ± 122.8 ± RI, MS, RS, odor sweet
1.7 ab 5.4b 30.6a
Acids
57 hexanoic acid 1847 1864 562.0 ± 914.1 ± 1595.8 ± RI, MS, RS, odor fatty, cheese, rancid
4.2c 35.8b 270.0a
58 acetic acid 1455 1450 60.6 ± 118.7 ± 328.1 ± RI, MS, RS, odor sharp pungent sour vinegar
1.8c 4.4b 26.7a
59 octanoic acid 2061 2060 24.0 ± 32.0 ± 93.1 ± 2.7a RI, MS, RS, odor sweat, cheese, oily, fatty
5.7b 3.9b
60 pentanoic acid 1736 54.7 ± 104.0 ± 139.2 ± RI, MS, RS, odor acidic and sharp, cheese-like, sour milky,
1.5c 3.6b 16.0a tobacco, with fruity nuances
61 nonanoic acid 2168 2165 22.4 ± 40.1 ± 48.9 ± 3.7a RI, MS, RS, odor green, fat, sweat, waxy
1.6c 1.7b
62 propanoic acid 1542 29.2 ± 53.1 ± 35.6 ± 4.1b RI, MS, RS pungent, rancid, soy
0.7c 2.6a
63 heptanoic acid 1956 1954 29.2 ± 55.5 ± 103.0 ± RI, MS, RS rancid, sour, sweaty
0.8b 1.2b 18.2a
64 butanoic acid 1616 1616 29.2 ± ND ND RI, MS, RS sharp acetic cheesy buttery fruity
0.9a
65 3-methyl-butanoic acid 1638 1643 29.2 ± 37.2 ± 48.1 ± 3.1a RI, MS, RS
0.10c 0.8b

ND: indicates not detected.

Identification methods: retention index (RI), mass spectra data (MS), reference standard compound (RS), and odor description (odor).
a, b, c
Means within a row with different superscripts significantly differ (P < 0.05), n = 3.

operated at a constant agitation speed of 500 rpm. Subsequently, they
were subjected to analysis by a UFGC-E-nose system (Heracles II, Alpha
M.O.S.; Toulouse, France) equipped with two DB-5/DB-1701 capillary
columns (2 m × 100 μm).
The analytical procedure was optimized by Alpha M.O.S. software.
Three thousand microliters of the extracts were injected(200 ◦ C) using a
headspace injection needle into the UFGC-E-nose system for 13 s at a
flow rate of 30 mL/min with an aid of 10 kPa hydrogen N7.0 carrier gas.
The trap system was maintained at 60 ◦ C for 18 s to adsorb, pre­
concentrate, and focalize the volatiles of the headspace. The flow rates
of the injector and trap were set at 30 and 10 mL/min, respectively. The
volatiles were introduced into the columns with an initial pressure of 80
kPa. The initial column temperature was 50 ◦ C and hold for 2 s; after
that, it was raised to 80 ◦ C at 1 ◦ C/s, finally it was raised to 250 ◦ C at
2 ◦ C/s and then hold for 60 s. The signal was acquired using an FID
detector (260 ◦ C) at a total acquisition time of 177 s and a digitalization
cycle of 0.01 s.
2.6. Gas chromatography-mass spectrometry/olfactory analysis
The GC separation consisted of GCMS-QP2010 instrument equipped
with a flame ionization detector (FID) and an ODP-2 Olfactory Detector
Port (Shimadzu, Kyoto, Japan). This system allowed us to simulta­
neously obtain a FID signal for the quantitation and the odor

4
C. Gao et al. Journal of Cereal Science 99 (2021) 103178

Fig. 1. Sum of rice bran volatile compounds under different storage time (A), heat map visualization of changes in volatile compounds identified in rice bran during
storage (B), GC-MS data for the rice bran in the different storage stages, PLS-DA score scatter plot (C), Important volatiles (VIP > 1.0) identified by PLS-DA(D).

characteristics of each compound detected by sniffing port. GC effluent (hydrogen) was 2 mL/min. The oven temperature was firstly increased
was split 3:1 among the FID and sniffing port. Samples were separated from 50 ◦ C (2 min), ramped at 5 ◦ C/min to 230 ◦ C, with a final holding
on the DB-5 analytical fused silica capillary column (60 m × 0.25 mm × time of 5 min; the injector and FID detector temperatures were set at 250
0.25 μm, Agilent, Santa Clara, CA). The flow rate of carrier gas and 200 ◦ C, respectively. Moist air was pumped into the sniffing port at

5
C. Gao et al.
Fig. 2. Key aldehydes in stored rice bran volatile compounds: hexanal (A), octanal (B), nonanal (C), (E)-2-nonenal (D), 2,4-decadienal (E) and 3-methyl-butanal (F).
Data are shown as Mean ± SEM of three independent experiments for all panels, * p < 0.05; ** p < 0.01; *** p < 0.001; ns, not significant (Student’s t-test).
50 mL/min to quickly remove the odorant eluted from sniffing port.
Each of the panelists was trained before sensory analysis in order to
get familiar with the odor description and aroma intensity (AI) of each
selected compound. The odor-active compounds perceived by six pan­
elists (three females and three males) were recorded as the time for onset
and end while sniffing the effluent. The panelists were also required to
note the perceived odor characteristic and intensity. With the same time,
the computer automatically recorded the retention time and sniffing
time of odor-active compound individually. The aroma intensities (AIs)
were evaluated using 3-point intensity scale from 1 to 3 corresponding
to weak, moderate and extreme intensities. The experiment was con­
ducted in triplicate by each panelist. Finally, the aroma intensity was the
average from six panelists. The relative standard deviation of AI and
statistically significant differences have been investigated in the
experiment.
2.7. Statistical analysis
Results are presented as the mean ± standard deviation from tripli­
cate analyses. Changes in volatiles in rice bran during storage were
determined by one-way analysis of variance. The quantitative descrip­
tive sensory analysis and aroma intensity of GC-O were submitted to
variance analysis (ANOVA). For subsequent multivariate statistical
analysis, the results of GC–MS were standardized due to a wide range of
counts for active volatile compounds. Principal component analysis
(PCA), partial least squares discriminant analysis (PLS-DA) and VIP
scores were conducted using MetaboAnalyst 4.0. Line and bar charts
were drawn using GraphPad Prism 8.
6
Journal of Cereal Science 99 (2021) 103178
3. Results and discussion
3.1. Volatile identification in fresh rice bran
A total of sixty-five volatile compounds were identified in fresh and
stored rice bran. These included 16 aldehydes, 10 ketones, 7 hydrocar­
bons, 9 alcohols, 9 acids and 14 additional compounds (Table 1). With
reference to the raw samples, these compounds were generally consid­
ered to originate from proteins, free amino acids, carbohydrates, tri­
glycerides, or their derivatives, in addition to the photosynthesis and
metabolism of vitamins and minerals (Zhao et al., 2020). As shown in
Fig. 1A, among these compounds, hydrocarbons were the dominant
volatile constituents of fresh rice bran. Straight-chain and cyclic alkanes
are recognized as endogenous to plants and originate from the decar­
boxylation of long-chain fatty acids (Kunst and Samuels, 2003). How­
ever, most alkenes had a high flavor threshold and had no significant
effect on the overall flavor profile. The second most common substances
in fresh rice bran were aldehydes. Among them, the contents of
straight-chain aldehydes, especially those of hexanal and nonanal, were
highest (Table 1). Grinding caused a certain degree of fat oxidation, and
the above two typical products were derived from oleic acid and linoleic
acid (Xiao et al., 2014). The total amount of ketones was comparable to
that of aldehydes. In fact, the formation of ketones can also be attributed
to the oxidative degradation of unsaturated fatty acids. 3,5-Octadie­
n-2-one, whose content was significantly higher than those of the
other compounds, was one of the major lipid oxidation products from
unsaturated fatty acids and could be used as an indicator of lipid
oxidation for perilla seed powder (Son et al., 2020). Alcohols and acids
only accounted for a small portion of the volatile compounds. In addi­
tion to aldehydes and ketones, alcohols were also generated mainly by
the thermal oxidation of lipids. The degradation of carbohydrates could
also produce high amounts of alcohols (Yan et al., 2020). However,
C. Gao et al. Journal of Cereal Science 99 (2021) 103178

Fig. 3. Key alcohols, furans and characteristic odor active volatile compounds in stored rice bran volatile compounds: 1-octanal (A), 1-octen-3-ol (B), 1-pentanol (C),
2-pently-furan (D), 2,3-dihydro-benzofuran (E), 2-methoxy-4-vinylphenol (F), 5-amino-2-methoxyphenol (G) and vanillin (H). Data are shown as Mean ± SEM of
three independent experiments for all panels, * p < 0.05; ** p < 0.01; *** p < 0.001; ns, not significant (Student’s t-test).

these compounds had a smaller impact than that of aldehydes and ke­ rice bran samples, and its increased level may be the result of hexanal
tones on the bran aroma owing to their higher odor thresholds. oxidation.
The PLS-DA analysis was performed to investigate the contribution
of key aroma compounds on sensory attributes of the rice bran fla­
3.2. Changes in volatile composition of rice bran during storage
vouring models. The differences among three rice bran samples had
been distinctly identified in the PLS-DA score plots as shown in Figue 1C
Changes in the volatile composition during storage are shown in
which exhibited a total variance of 98.8% (PLS1, 83.2%; PLS2, 13.1%)
Table 1. The storage period influenced the volatile levels in rice bran (p
with plot satisfaction values for X variables of 0.988 (R2X) and predic­
< 0.05). A heat map is depicted in Fig. 1B, where clear differences can be
tion accuracy of 0.992 (Q2). The variable importance for projection
observed in the samples. Seven new volatile compounds formed during
(VIP) values were calculated from the PLS regression model of the three
14 days of storage. The contents of aldehydes gradually increased,
samples of different storage times (Fig. 1C). The VIP scores for the 15
becoming the dominant compound class. After 14 days, the amounts of
aroma compounds were >1. These compounds worked as indicators for
aldehydes increased 1-fold in rice bran. Among aldehydes, saturated
the discrimination of rice bran during storage (VIP > 1 and p < 0.05).
aldehydes such as hexanal and nonanal maintained high contents and
According to the threshold value in the literature, we calculated the OAV
fast accumulation rates, while the contents of unsaturated aldehydes
value of these compounds and we selected the substances with the OAV
such as (Z)-2-heptenal, (E)-2-octenal, (E, E)-2,4-nonadienal and 2,4-dec­
value greater than one from the 15 substances in Fig. 1D and the com­
adienal were relatively low. Many unsaturated aldehydes were found in
mon aroma compounds of cereals in literature. Then we found some
the reaction system, had high reactivity and were prone to retro-aldol
characteristic substances of rice husk or bran which were reported in the
reactions to produce many kinds of saturated aldehydes (Adams et al.,
literature we had for future analysis (Figs. 2–3).
2011). Notably, (E, E)-2,4-heptadienal was newly found, and its content
As demonstrated in Fig. 2, several common saturated aldehydes as
doubled during storage. Linoleic acid (C18:2) is one of the main fatty
well as unsaturated aldehydes all had low thresholds (0.027–40 ppb)
acids in rice bran. Linoleic acid is oxidized to form 9-OOOH and
(He et al., 2020). Sjovall et al. detected C6–C9 saturated aldehydes in oat
13-OOOH hydrogen peroxides, which are further degraded to form al­
flour that was stored for 18 weeks at 32 ◦ C and identified the major
dehydes such as (E,E)-2,4-decadienal, 2-octenal, and hexanal (Jayasena
volatile compounds as hexanal and nonanal (McGorrin, 2019). In pre­
et al., 2013). Additionally, the rate of increase of hexanal was greater
vious studies, these aldehydes were also regarded as main odor com­
than that of nonanal because of the fatty acid composition as well. Thus,
pounds. (E)-2-Nonenal and hexanal were also reported to be rancid
for rice bran, hexanal may be an early oxidation marker (Gan et al.,
defects with the highest sensory significance in virgin olive oil (Neu­
2005). The contents of alcohols, ketones and acids also increased. 1-Hex­
gebauer et al., 2020). With extended storage from 0 days to 14 days, the
anol and 1-pentanol are secondary oxidation products of linoleic acid.
sour and rancid odor of the tested rice bran samples was much stronger
1-Pentanol is a lipoxygenase-initiated reaction product, along with
because of the abovementioned aldehydes. 3-Methylbutanal, which
2-ethyl-1-hexanol, 2-pentylfuran and heptanal (Lee et al., 2014). Hy­
provided a malt odor, decreased in the rice bran after 14 days of storage.
droperoxides of glycerides produced in oxidized fats can also change the
This was consistent with a previous report (Lee et al., 2014).
degradation pathway to produce reducing alcohols (Mottram, 1998).
Fig. 3A–E reflected trends in contents of several key alcohols and
Furthermore, acids are produced by further oxidation of aldehydes.
furans. The level of 1-pentanol increased over time. A similar trend was
Hexanoic acid was found to be the most abundant acid detected in the

7
C. Gao et al. Journal of Cereal Science 99 (2021) 103178

Fig. 4. PCA score plot (A) and PCA loading plot (B) based on representative lipid oxidation volatile products and odor-active compounds in stored rice bran. PCA
score plot for the differentiation of six stabilized samples: E-nose (C) and GC-MS (D). URB: untreated rice bran; ERB: extruded rice bran; MRB: microwaved rice bran;
DRB: dry heated rice bran; SRB: steamed rice bran; HRB: high pressure steamed rice bran.

observed for 1-octanol and 1-octen-3-ol, the latter of which is an active
alcohol and contributed a mushroom smell to these products. 1-Octen-3-
ol was recognized as the source of the unpleasant smell of rice bran and
was connected with linoleic acid (Zeng et al., 2012; Zhang et al., 2019).
2-Pentyl-furan is an oxidation product of linoleic acid and linoleic acid
and was responsible for an undesirable fruity, green, earthy, beany odor
with a 6 ppb threshold value. 2-Pentylfuran was formed in a lip­
oxygenase reaction along with 1-pentanol (Choi et al., 2019).
In addition to the aforementioned unpleasant volatile compounds
that formed and accumulated during the storage of rice bran, the con­
centrations of various volatile compounds that gave rice bran its char­
acteristic flavor changed during storage. Fig. 3 depicts that the contents
of all of these characteristic flavor compounds increased after 14 days of
storage. There were some compounds derived from phenolic compounds
or lignin degradation, such as 2-methoxy-4-vinylphenol (spice or clove),
5-amino-2-methoxyphenol or vanillin (vanilla). The structure of vanillin
is similar to that of guaiacol, except a CH2 moiety of the latter is
substituted with an oxygen atom (Choi et al., 2019). Vanillin originates
from lignin degradation in the presence of air and can be formed by
thermal degradation of ferulic acid. 2-Methoxy-4-vinylphenol was ob­
tained from the thermal decarboxylation of ferulic acid, which is the
most abundant phenolic acid in rice bran (Arsa et al., 2019).
Unsaturated double bonds of 2-methoxy-4-vinylphenol, are oxidized
and replaced by amine groups to form 5-amino-2-methoxyphenol. The
increase in the contents of these characteristic substances was mainly
related to the content of guaiacol. In a previous study, an increased
guaiacol content could be explained by the bioconversion of ferulic acid,
a major phenolic compound in rice bran, to guaiacol during storage
(Choi et al., 2018).
3.3. PCA and PLS analysis
On the basis of all stored samples, PCA was performed on the volatile
compound data (Fig. 4A). The principle components 1 (76.2%) and 2
(19.1%) has the accumulating contribution of 95.30%, which is much
larger than 80%, with a discrimination index value of 95. As storage
proceeded, the samples were distributed distinctly in different regions in
the PCA loading plot. Volatile profiles in late storage periods (2 weeks)
were separated from volatile profiles from early storage periods (0
weeks). Along the PC1 axis, early storage periods clustered on the left
side, whereas late storage periods clustered on the right side.
The PCA loading plot (Fig. 4B) indicated that the compounds formed
during storage drove the separation. Raw rice bran samples were
correlated with octanal, 1-pentanol and 2-pentyl-furan, indicating their

8
 C. Gao et al.
Table 2
GC-O identified odor-active compounds in rice bran samples with the method of aroma intensity.
Compound Aroma description Aroma intensity

RI Identification URB RSD ERB RSD MRB RSD DRB RSD SRB RSD HRB RSD
(%) (%) (%) (%) (%) (%)

3-methyl-butanal Malt 655 AD, RI, Std 0.67a 28.87% 0.97a 5.77% - 0.83a 28.87% - -
Pentanal pungent, fermented 697 AD, RI, Std 0.98a 25.17% 0.93a 5.77% - 1.10a 10.00% - 0.33b 15.28%
Hexanal grass, green 780 AD, RI, Std 2.17a 28.87% 1.60b 52.92% 1.07c 11.55% 0.77c 25.17% 0.67c 28.87% -
o-xylene sweet 898 AD, RI, Std - - - - 0.47a 5.77% -
Octanal lemon, green, fat 1004 AD, RI, Std 1.43a 40.41% 1.50a 10.00% - 1.20 ab 20.00% 0.93b 11.55% -
1-penten-3-ol Green 680 AD, RI, Std 0.43a 11.55% - - - - -
2-pentyl-furan nutty, buttery 996 AD, RI, Std 2.33a 57.74% 1.34bc 15.10% 2.20a 20.00% 1.50b 50.00% 0.83cd 15.28% 0.53d 5.77%
1-pentanol oily, citrus 767 AD, RI, Std 1.03a 15.28% 0.43b 5.77% - 0.90a 10.00% - -
(E)-2-heptenal fatty, nutty 960 AD, RI, Std - 1.13b 11.55% - 2.17a 15.28% - 1.03b 15.28%
6-methyl-5-hepten-2-one popcorn 988 AD, RI, Std 1.27bc 11.55% 1.15c 5.03% - 1.20bc 26.46% 1.43b 11.55% 1.93a 11.55%
3-octen-2-one nut, caramel 1036 AD, RI, Std 1.90a 10.00% - - 1.23b 25.17% - 1.07b 11.55%
1-octen-3-ol raw mushroom 978 AD, RI, Std - - - - - 1.03a 5.77%
acetic acid Sour 606 AD, RI, Std 2.07b 11.55% 1.33c 15.28% 1.00d 20.00% 2.20b 20.00% 1.37c 11.55% 2.93a 11.55%
trans-3-nonen-2-one licorice, oily 1135 AD, RI, Std - - - 1.10a 10.00% 0.80b 20.00% 1.13a 11.55%
benzaldehyde almond, nut 961 AD, RI, Std - - - 1.17a 15.28% - 0.77b 25.17%
(E)-2-nonenal grass，fat，cucumber 1161 AD, RI, Std 1.00c 0.00% - - 1.63b 32.15% 1.60b 10.00% 2.03a 5.77%
9

1-octanol moss, grass 1078 AD, RI, Std 0.43b 20.82% 0.53b 5.77% - 1.03a 15.28% - 0.93a 5.77%
3,5-octadien-2-one fat, mushroon, green, cucunber 1052 AD, RI, Std 1.93a 11.55% 1.90a 10.00% - 1.07b 5.77% - 1.53a 50.33%
5-methyl-2-furancarboxaldehyde sweet, bready 955 AD, RI, Std - - - 1.47a 5.77% - -
(E,E)-2,4-nonadienal rancid, oily, nut 1215 AD, RI, Std - - 1.47c 5.77% 2.53a 50.33% 2.07b 11.55% 1.07d 11.55%
5-ethyldihydro-2(3H)-furanone sweet 1068 AD, RI, Std 1.93a 11.55% 1.93a 5.77% 1.23b 25.17% 1.17b 15.28% 2.03a 15.28% 2.03a 5.77%
pentanoic acid cheese-like, sour milky, fruity 926 AD, RI, Std 1.07b 11.55% 0.63c 5.77% 0.63c 5.77% 1.27b 25.17% 0.70c 10.00% 1.77a 25.17%
nuances
(E,E)-2,4-decadienal nutty, melon, oily 1337 AD, RI, Std - - 0.85b 13.61% 0.83b 28.87% 0.83b 15.28% 2.30a 26.46%
hexanoic acid fatty, rancid 1010 AD, RI, Std 2.17b 28.87% - 2.18b 17.56% 2.20b 26.46% 2.53a 5.77%
(E)-6,10-dimethyl-5,9-undecadien-2- waxy, almond 1425 AD, RI, Std 2.03b 5.77% 1.57c 11.55% 1.90b 17.32% 2.83a 15.28% - 2.93a 11.55%
one
heptanoic acid rancid, sour, sweaty 1074 AD, RI, Std - - 0.53c 5.77% 1.03b 5.77% 1.03b 15.28% 1.47a 5.77%
Maltol caramel 1085 AD, RI, Std - - - - - 0.67a 41.63%
octanoic acid sweat, cheese 1182 AD, RI, Std 0.43d 5.77% 0.52d 2.89% 0.93c 11.55% - 1.17b 15.28% 1.37a 15.28%
nonanoic acid fat 1273 AD, RI, Std 1.07b 11.55% 1.40a 17.32% 1.03b 15.28% 0.65c 13.23% 1.07b 11.55% 1.07b 23.09%
2-methoxy-4-vinylphenol peanut, roasted 1323 AD, RI, Std - - - - - 1.20a 20.00%

Journal of Cereal Science 99 (2021) 103178

2,3-dihydro-benzofuran sweet, green 1226 AD, RI, Std 0.77c 25.17% 1.33b 20.82% 1.33b 15.28% 1.53b 5.77% 1.63b 15.28% 2.93a 11.55%
Vanillin vanilla 1403 AD, RI, Std - - - - - 1.03a 5.77%

Method of identification: RI: retention index; Std: confirmed by authentic standards; AD: aroma descriptor.
-: not perceived.
a, b, c
Means within a row with different superscripts significantly differ (P < 0.05), n = 3.
C. Gao et al.
potential as early markers. Hexanal, nonanal, (E)-2-nonenal, 2-methoxy-
4-vinylphenol, and 2,4-decadienal were on the right side of the PC1 axis.
These volatile compounds contributed greatly to the day 7 samples. 1-
Octen-3-ol, 1-octanol and vanillin were closely connected with the day
14 samples.
3.4. PCA of E-nose and GC-MS data from stabilized rice bran
For the E-nose results, the PCA diagram (Fig. 4C) summarized the
overall relations between the attributes and samples. PC1 and PC2
explained 94% of the total variance. This reflected great differences
between raw and processed rice bran samples. Among the five stabilized
samples, DRB and ERB had unique odors that were not similar to those of
the other samples. The odors of the remaining three samples were
relatively similar. This was consistent with the PCA results of the GC-MS
data. As shown in Fig. 4D, the first two principal components (PC1 and
PC2) explained 40.2% and 21% of the data variance, respectively. The
raw samples were located in the negative region of both the PC1 and PC2
axes and were separate from the other samples. Furthermore, different
treated groups were obviously classified. The extruded and roasted
samples were located in the negative region of the PC1 axis and the
positive region of the PC2 axis. The microwave cooked and steamed
samples were located in the positive region of the PC1 axis were located
at the boundary of the PC2 axis. Finally, the high-pressure steamed
samples were located in the first quadrant alone.
The distinct treatment methods resulted in distinguishable flavor
profiles, which might be caused by the complex mechanism of the
Maillard reaction in the multicomponent system of rice bran. In the
Maillard reaction, moisture is an important factor that impacts the di­
rection of the reaction and the levels of volatile compounds generated
via this pathway. This was one reason why the aroma profiles of the
roasted and steamed samples were different. Because both high-pressure
steaming and atmospheric steaming involved moisture, the contents of
aldehydes, ketones, and alcohols showed a significant downward trend
due to their diffusion into the water phase and possible biotransforma­
tion reactions after wet heat treatment. On the other hand, the enzyme-
inactivating effect of lipase and lipoxygenase was also an important
factor affecting odor (McGorrin, 2019). This effect delayed the process
of lipid oxidation to a certain extent.
3.5. GC-O results for stabilized rice bran samples
The results of olfactometric analysis are summarized in Table 2.
Application of GC− O to rice bran revealed 20, 17, 12, 25, 17 and 25
volatile compounds in the six samples. The differences in AI of volatile
compounds of the samples were mainly caused by concentration dif­
ferences of these compounds. The AIs of the compounds ranged from 0.3
to 2.9. Among these compounds, aldehydes were the largest class of
aroma compounds in the samples. As presented in Table 2, the DRB and
HRB samples possessed the most odor-active compounds among all
samples. The Maillard reaction played a key role in the development of
these compounds. Robert J. McGorrin (2019) proposed that additional
flavors in toasted oat cereals were attributed to pyrazines, pyrroles,
furans, and sulfur-containing compounds, which were products of
nonenzymatic browning.
A total of 9 aldehydes were identified and are summarized in Table 2.
These aldehydes included 3-methyl-butanal, pentanal, hexanal, (E)-2-
heptenal, octanal, (E,E)-2,4-nonadienal, (E,E)-2,4-decadienal, vanillin
and benzaldehyde. Aldehydes were generally associated with green,
grass, nutty and fatty notes in the sensory descriptions from panelists
(Table 2). The results were consistent with those of previous in­
vestigations that showed aldehydes with six to ten carbons as being
perceived as having green, fatty or tallow aromas. Green aroma is
sometimes referred to as a fresh note, and the chemicals related to this
aroma are predominantly C6 alcohols and aldehydes and are typically
unsaturated (Zhu et al., 2018). However, an excessively high aldehyde
10
Journal of Cereal Science 99 (2021) 103178
concentration can also produce an unpleasant greasy and rancid taste.
After the dry heat treatment process, the aroma intensity of saturated
aldehydes except hexanal increased because of the promotion of fatty
acid oxidation. Volatilization of the formed hexanal during heat treat­
ment may also be the reason for the decrease in its content. Volatile
secondary products such as (E,E)-2,4-nonadienal and (E,E)-2,4-deca­
dienal contributed to almond and nutty notes to rice bran (Josephson
and Lindsay, 1987). The slight increase in these aromas may contribute
to maintaining the freshness of rice bran products since they often
present green and floral flavors at low levels. The aldehydes generated
corresponding acids through further oxidation, and these acids had
cheese, sweet, sour, and fat aromas. The intensity of these odor active
substances became stronger during storage.
In addition to aldehyde compounds, ketones and alcohols were also a
significant class of aroma active compounds found in the rice bran
samples. In particular, the AIs of 5-ethyldihydro-2(3H)-furanone and 1-
octen-3-ol were increased after high pressure treatment (Xia et al.,
2017). It is known that high-pressure treatment can reveal the flavor of
some substances. For instance, maltol, vanillin, 2-methoxy-4-vinylphe­
nol and 2,3-dihydro-benzofuran provided rice bran with an acceptable
odor (caramel, vanilla) after high-pressure treatment. In conclusion, the
processed rice bran changed from the original grassy, oily flavor to va­
nilla, cheese, and caramel flavor after stabilization.
4. Conclusion
Sixty-five volatile compounds in rice bran stored for up to 14 days
were detected by HS-SPME with GC–MS, including aldehydes, ketones,
alcohols, hydrocarbons and acids. The relative concentration of alde­
hydes increased with storage time, and hexanal was the component with
the highest content. Similar behavior was exhibited for ketones and al­
cohols, all of which were connected with early oxidation of rice bran.
The main characteristic odor compounds of rice bran were vanillin, 2-
methoxy-4-vinylphenol and 5-amino-2-methoxyphenol regarding
ferulic acid, which increased during storage for up to 2 weeks. In the
PCA plot, 1-octen-3-ol was highly correlated with rice bran samples after
long-term storage, and octanal was highly correlated with rice bran
samples after short-term storage. After stabilizing, the volatile com­
pounds of six kinds of rice bran were distinguished through PCA. The
Maillard reaction played a key role in the production of these com­
pounds, and moisture was an important factor that influenced the di­
rection of these reaction. The GC-O experiment verified that the
processed rice bran changed from the original grassy, oily flavor to va­
nilla, cheese, and caramel flavors.
CRediT authorship contribution statement
Chen Gao: Investigation, Writing - original draft. Yan Li: Investi­
gation. Qifeng Pan: Data curation. Mingcong Fan: Software. Li Wang:
Supervision. Haifeng Qian: Writing - review & editing.
Declaration of competing interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
the work reported in this paper.
Acknowledgements
This work was supported by the Ministry of Science & Technology of
China (2020YFC1606804)and the grants from the National Natural
Science Foundation of China (32072254).
C. Gao et al. Journal of Cereal Science 99 (2021) 103178

References Li, Q., Sun, H., Zhang, M., Wu, T., 2020. Characterization of the flavor compounds in
wheat bran and biochemical conversion for application in food. J. Food Sci. 85,
1427–1437.
Adams, A., Kitryte, V., Venskutonis, R., De Kimpe, N., 2011. Model studies on the pattern
McGorrin, R.J., 2019. Key aroma compounds in oats and oat cereals. J. Agric. Food
of volatiles generated in mixtures of amino acids, lipid-oxidation-derived aldehydes,
Chem. 67, 13778–13789.
and glucose. J. Agric. Food Chem. 59, 1449–1456.
Mottram, D.S., 1998. Flavour formation in meat and meat products: a review. Food
Arsa, S., Theerakulkait, C., Cadwallader, K.R., 2019. Quantitation of three strecker
Chem. 62, 415–424.
aldehydes from enzymatic hydrolyzed rice bran protein concentrates as prepared by
Neugebauer, A., Granvogl, M., Schieberle, P., 2020. Characterization of the key odorants
various conditions. J. Agric. Food Chem. 67, 8205–8211.
in high-quality extra virgin olive oils and certified off-flavor oils to elucidate aroma
Baek, H.H., Cadwallader, K.R., 1996. Volatile compounds in flavor concentrates
compounds causing a rancid off-flavor. J. Agric. Food Chem. 68, 5927–5937.
produced from Crayfish-processing byproducts with and without protease treatment.
Son, Y., Lee, K.Y., Gu, S., Park, J.Y., Choi, S.G., Kim, H.J., 2020. Quality changes in
J. Agric. Food Chem. 44, 3262–3267.
perilla seed powder related to storage duration and temperature. J. Food Sci.
Bi, S., Wang, A., Wang, Y., Xu, X., Luo, D., Shen, Q., Wu, J., 2019. Effect of cooking on
Technol. 57, 263–273.
aroma profiles of Chinese foxtail millet (Setaria italica) and correlation with sensory
Wei, C.K., Ni, Z.J., Thakur, K., Liao, A.M., Huang, J.H., Wei, Z.J., 2020. Aromatic effects
quality. Food Chem. 289, 680–692.
of immobilized enzymatic oxidation of chicken fat on flaxseed (Linum usitatissimum
Chen, Y., Ma, Y., Dong, L., Jia, X., Liu, L., Huang, F., Chi, J., Xiao, J., Zhang, M.,
L.) derived Maillard reaction products. Food Chem. 306, 125560.
Zhang, R., 2019. Extrusion and fungal fermentation change the profile and
Xia, Q., Mei, J., Yu, W., Li, Y., 2017. High hydrostatic pressure treatments enhance
antioxidant activity of free and bound phenolics in rice bran together with the
volatile components of pre-germinated brown rice revealed by aromatic
phenolic bioaccessibility. LWT (Lebensm.-Wiss. & Technol.) 115.
fingerprinting based on HS-SPME/GC-MS and chemometric methods. Food Res. Int.
Choi, S., Seo, H.S., Lee, K.R., Lee, S., Lee, J., 2018. Effect of cultivars and milling degrees
91, 103–114.
on free and bound phenolic profiles and antioxidant activity of black rice. Applied
Xiao, L., Lee, J., Zhang, G., Ebeler, S.E., Wickramasinghe, N., Seiber, J., Mitchell, A.E.,
Biological Chemistry 61, 49–60.
2014. HS-SPME GC/MS characterization of volatiles in raw and dry-roasted almonds
Choi, S., Seo, H.S., Lee, K.R., Lee, S., Lee, J., Lee, J., 2019. Effect of milling and long-term
(Prunus dulcis). Food Chem. 151, 31–39.
storage on volatiles of black rice (Oryza sativa L.) determined by headspace solid-
Yan, W., Liu, Q., Wang, Y., Tao, T., Liu, B., Liu, J., Ding, C., 2020. Inhibition of lipid and
phase microextraction with gas chromatography-mass spectrometry. Food Chem.
aroma deterioration in rice bran by infrared heating. Food and Bioprocess
276, 572–582.
Technology.
Franklin, L.M., Chapman, D.M., King, E.S., Mau, M., Huang, G., Mitchell, A.E., 2017.
Yu, C.W., Hu, Q.R., Wang, H.W., Deng, Z.Y., 2020. Comparison of 11 rice bran
Chemical and sensory characterization of oxidative changes in roasted almonds
stabilization methods by analyzing lipase activities. J. Food Process. Preserv. 44, 14.
undergoing accelerated shelf life. J. Agric. Food Chem. 65, 2549–2563.
Yucheng, Z., Xingrong, J., Wenye, C., Juan, Y., Zhigao, W., Aluko, R.E., Rong, H., 2020.
Gam, D.H., Jo, J.M., Jung, H.J., Kim, J.W., 2018. Optimization of extraction conditions
Rice bran attenuated obesity via alleviating dyslipidemia, browning of white
of antioxidant activity and bioactive compounds from rice bran by response surface
adipocytes and modulating gut microbiota in high-fat diet-induced obese mice. Food
methodology. Applied Chemistry for Engineering 29, 726–733.
& Function 11, 2406–2417.
Gan, H.L., Man, Y.B.C., Tan, C.P., NorAini, I., Nazimah, S.A.H., 2005. Characterisation of
Zeng, M., Zhang, L., He, Z., Qin, F., Tang, X., Huang, X., Qu, H., Chen, J., 2012.
vegetable oils by surface acoustic wave sensing electronic nose. Food Chem. 89,
Determination of flavor components of rice bran by GC-MS and chemometrics.
507–518.
Analytical Methods 4.
He, C., Li, Z., Liu, H., Zhang, H., Wang, L., Chen, H., 2020. Characterization of the key
Zhang, X., Zhang, M., Dong, L., Jia, X., Liu, L., Ma, Y., Huang, F., Zhang, R., 2019.
aroma compounds in Semnostachya menglaensis Tsui by gas chromatography-
Phytochemical profile, bioactivity, and prebiotic potential of bound phenolics
olfactometry, odor activity values, aroma recombination, and omission analysis.
released from rice bran dietary fiber during in vitro gastrointestinal digestion and
Food Res. Int. 131, 108948.
colonic fermentation. J. Agric. Food Chem. 67, 12796–12805.
Jayasena, D.D., Ahn, D.U., Nam, K.C., Jo, C., 2013. Flavour chemistry of chicken meat: a
Zhao, Q., Xue, Y., Shen, Q., 2020. Changes in the major aroma-active compounds and
review. Asian-Australas. J. Anim. Sci. 26, 732–742.
taste components of Jasmine rice during storage. Food Res. Int. 133, 109160.
Josephson, D.B., Lindsay, R.C., 1987. Retro-aldol related degradation of 2,4-decadienal
Zhu, J., Wang, L., Xiao, Z., Niu, Y., 2018. Characterization of the key aroma compounds
in the development of staling flavors in fried foods. J. Food Sci. 52, 1186–1190.
in mulberry fruits by application of gas chromatography-olfactometry (GC-O), odor
Kunst, L., Samuels, A.L., 2003. Biosynthesis and secretion of plant cuticular wax. Prog.
activity value (OAV), gas chromatography-mass spectrometry (GC-MS) and flame
Lipid Res. 42, 51–80.
photometric detection (FPD). Food Chem. 245, 775–785.
Lee, J., Xiao, L., Zhang, G., Ebeler, S.E., Mitchell, A.E., 2014. Influence of storage on
volatile profiles in roasted almonds (Prunus dulcis). J. Agric. Food Chem. 62,
11236–11245.

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