Identification of volatile organic compounds generated ... · PDF fileSchematic diagram of the...
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Sample Red chili powder (fresh, medium-infected and high-infected) Commercial chili powder (12 products) Solvent-free solid injector Instrument Agilent Technologies 6890A equipped with a 5973 MSD Column HP-5MS (30 m x 0.25 mm i.d, 0.5μm film thickness, Agilent, (USA) Column flow 1 mL/min (He) Oven temp. 50℃ (4 min) – 4℃/min – 250℃ (1 min) Injector temp. 250℃ Ion source temp. 230℃ Quadruple temp. 150℃ In this study, the volatiles organic compounds generated from fresh and infected red pepper powder were characterized using solvent-free solid injection (SFSI) coupled with Gas Chromatogram-mass spectrometry(GC-MS), in order to investigate adulteration in commercial red pepper powder. Jae-Han Shim a* , Ah-Young Ko a , Md. Musfiqur Rahman, A a . M. Abd El-Aty b , Jin Jang a , Jeong-Heui Choi a , M. I. R Mamun a a Natural Products Chemistry Laboratory, Biotechnology Research Institute, Chonnam National University, Gwangju, Republic of Korea b Department of Pharmacology, Faculty of Veterinary Medicine, Cairo University, 12211-Giza, Egypt Table 1. Volatile organic compounds generated from healthy and infected chili powder using solvent-free solid injection and gas chromatography/mass spectrometry. • Chili peppers in the genus Capsicum are native plants of America, and very popular in several parts of the world. Due to their unique spicy, pungent taste, color, and natural flavoring, they have become an emblematic ingredient in many regional cuisines. Chili contains large amounts of vitamins A, B, C, and small amounts of carotene, which make it a good source of vitamins. • • Volatile organic compounds (VOCs) are generally correlated with flavor and fragrance in foodstuffs and are important factors to evaluate consumer acceptance or rejection of food products. In addition, volatile compounds possess aromatic, anti-fungal, insecticidal, biological signaling, and therapeutic properties. Therefore, investigating VOCs is important to assess food quality, authenticity, purity, and origin. Homepage : http://altair.chonnam.ac.kr/~jhshim E-mail : [email protected] Identification of volatile organic compounds generated from healthy and infected powdered chili using solvent-free solid injection coupled with GC/MS: Application to adulteration Abstract Introduction Sample Preparation and vaporization Solvent-free solid injector vaporization procedures GC/MS analytical conditions Volatile compounds emitted from pepper powder Fig. 2. Schematic diagram of the solvent-free solid injector (SFSI). In order to distinguish between VOCs generated in healthy and infected chili powder, SFSI technique was used. A total of 43 compounds were confirmed in healthy, medium-infected and severely infected chili powder. Trimethylamine and isosorbide were useful as biomarkers for identifying infected chili and could be used to investigate adulteration in chili powder. The coupling of SFSI-GC/MS was an effective technique for the rapid analysis and characterization of VOCs in chili power. Conclusions To investigate adulteration in commercial chili powder, the volatile organic compounds of healthy and infected powdered chili pepper were characterized using a solvent-free solid injector (SFSI) coupled with gas chromatography/mass spectrometry (GC/MS). Except for one compound (capillary compound for blank), 43 compounds were identified in healthy and infected chili powder. Specifically, 31, 36, and 41 compounds were identified in healthy, medium-infected, and severely infected chili powder. Among these compounds, acetic acid (13.77%), propanal (2.477%), N-methylpyrrole (1.986%), and 2-methyl-propanal (1.768%) were leading volatiles in the healthy chili powder. In contrast, infected chili powder contained 9,12-octadecadienoic acid, ethyl ester (15.984%), acetic acid (11.249%), hexadecanoic acid, methyl ester (3.3%), N-methylpyrrole (3.221%), and 2-furanmethanol (2.629%) as major compounds. Trimethylamine and isosorbide were detected in both medium and severely infected chilli, but not in healthy chili. This means that these compounds could be used as biomarkers to distinguish between healthy and infected chili. The proposed technique was applied to 12 commercial chili powders, and trimethylamine and isosorbide were detected in six samples. These results suggest that a contaminated chili that was added to a healthy one could be successfully identified by a combination of the SFSI and GC/MS. Keywords: Healthy; Infected; Red pepper powder; Chili; Adulteration; Solid injector; Sample preparation, gas chromatography-mass spectrometry Objectives Materials and Methods Glass crusher Silicone seals Glass capillary Outlet of vaporized sample Supporting bar (1) (2) (3) (4) (5) (6) Fig. 1. Infected red pepper and adulterated red pepper powder. Fig. 3. Solvent-free solid injector (SFSI) vaporization procedures. Red pepper powder sample (1 mg) Put in a soft glass capillary tube Seal both ends of the tube Place the tube in a SFSI Coupled with a GC/MS Pre-heating time 7 min GC/MS analysis Preparation Vaporization Results Fig. 4. Representative gas chromatography/mass spectrometry chromatograms (full scan mode) of the volatile organic compounds (A) blank sample, (B) healthy, (C) medium- infected, and (D) severely infected (E) commercial chili powders. No. RT Compound Blank Fresh Infected (M) Infected (H) Relative area (%) 1 1.721 Propanal - 2.477 2.167 1.160 2 1.773 Trimethylamine - - 0.332 0.473 3 1.861 Acetic acid, methyl ester - 1.345 1.261 0.709 4 2.015 Propanal, 2-methyl- - 1.768 1.412 0.658 5 2.197 2,3-Butanedione - 0.855 1.147 0.359 6 2.270 2-Butanone - 0.641 0.568 0.296 7 2.342 Furan, 2-methyl- - 1.324 0.969 0.443 8 2.827 Acetic acid - 13.777 11.249 7.419 9 2.897 Butanal, 3-methyl- - 1.318 1.154 0.565 10 3.031 Butanal, 2-methyl- - 1.215 0.979 0.493 11 3.182 2-Propanone, 1-hydroxy- - 0.624 0.553 0.402 12 3.506 2,3-Pentanedione - 0.276 0.181 0.115 13 4.489 N,N-Dimethyl-2-aminoethanol - 0.310 0.686 0.606 14 4.629 N-Methylpyrrole - 1.986 3.221 1.631 15 4.894 Pyridine - - 0.125 0.080 16 4.998 Pyrrole - 0.116 0.245 0.238 17 7.200 Pyrazine, methyl- - 0.190 0.324 0.559 18 7.613 Unknown compound 1 - 0.615 0.374 - 19 8.619 2-Furanmethanol - 1.429 2.629 1.221 20 9.083 Unknown compound 2 - 0.576 0.978 0.390 21 10.780 Pyrazine, 2,6-dimethyl- - 0.413 0.392 0.414 22 10.947 Butyrolactone - 1.011 1.297 0.822 23 13.014 2-Furancarboxaldehyde, 5-methyl- - 1.039 0.396 0.085 24 15.813 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- - 0.294 0.303 0.200 25 16.367 2-Pyrrolidinone, 1-methyl- - 0.179 0.496 0.261 26 16.490 Benzeneacetaldehyde - 0.151 - 0.228 27 17.273 Ethanone, 1-(1H-pyrrol-2-yl)- - 0.490 0.568 1.155 28 17.910 2-Pyrrolidinone - - - 0.914 29 18.440 Phenol, 2-methoxy-/Phenol, o-methoxy- - 0.342 0.289 0.866 30 18.734 Acetoglyceride - - - 1.339 31 19.427 Maltol - 1.174 - 0.887 32 20.438 Unknown compound 3 - - 2.122 0.959 33 23.272 1,2-Benzenediol - - 0.352 - 34 26.843 Isosorbide - - 0.539 1.051 35 34.721 2-Propanone, 1-(4-hydroxy-3-methoxyphenyl)- - 0.461 0.379 0.175 36 40.338 Tetradecanoic acid, methyl ester, - - - - 0.302 37 45.874 Hexadecanoic acid, methyl ester - - 0.629 1.340 3.300 38 46.312 Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2- methylpropyl)- - - 0.525 0.430 0.598 39 46.986 Unkown compound 4 - 12.566 1.167 1.116 1.595 40 50.260 9,12-Octadecadienoic acid (Z,Z)-, methyl ester 12.566 - 1.062 3.539 15.984 41 50.323 Unkown compound 5 - - - 1.602 3.994 42 50.866 Octadecanoic acid, methyl ester - - - 0.398 1.108 43 51.757 9,12-Octadecadienoic acid, ethyl ester - - - - 0.751 44 52.242 Hexadecanamide - - - - 0.463
Transcript of Identification of volatile organic compounds generated ... · PDF fileSchematic diagram of the...
Sample
Red chili powder
(fresh, medium-infected and high-infected)
Commercial chili powder (12 products)
Solvent-free solid injector
Instrument Agilent Technologies 6890Aequipped with a 5973 MSD
Column HP-5MS (30 m x 0.25 mm i.d, 0.5μm film thickness, Agilent, (USA)
Column flow 1 mL/min (He)
Oven temp. 50℃ (4 min) – 4℃/min – 250℃ (1 min)
Injector temp. 250℃
Ion source temp. 230℃
Quadruple temp. 150℃
In this study, the volatiles organic compounds generated fromfresh and infected red pepper powder were characterized usingsolvent-free solid injection (SFSI) coupled with GasChromatogram-mass spectrometry(GC-MS), in order toinvestigate adulteration in commercial red pepper powder.
Jae-Han Shima*, Ah-Young Koa, Md. Musfiqur Rahman, Aa. M. Abd El-Atyb, Jin Janga, Jeong-Heui Choia, M. I. R Mamuna
aNatural Products Chemistry Laboratory, Biotechnology Research Institute, Chonnam National University, Gwangju, Republic of KoreabDepartment of Pharmacology, Faculty of Veterinary Medicine, Cairo University, 12211-Giza, Egypt
Table 1. Volatile organic compounds generated from healthy andinfected chili powder using solvent-free solid injection andgas chromatography/mass spectrometry.
• Chili peppers in the genus Capsicum are native plants ofAmerica, and very popular in several parts of the world. Dueto their unique spicy, pungent taste, color, and naturalflavoring, they have become an emblematic ingredient inmany regional cuisines. Chili contains large amounts ofvitamins A, B, C, and small amounts of carotene, whichmake it a good source of vitamins.
•• Volatile organic compounds (VOCs) are generally correlated
with flavor and fragrance in foodstuffs and are importantfactors to evaluate consumer acceptance or rejection of foodproducts. In addition, volatile compounds possess aromatic,anti-fungal, insecticidal, biological signaling, and therapeuticproperties. Therefore, investigating VOCs is important toassess food quality, authenticity, purity, and origin.
Homepage : http://altair.chonnam.ac.kr/~jhshim E-mail : [email protected]
Identification of volatile organic compounds generated from healthy and infected powdered chili using solvent-free solid injection coupled with GC/MS: Application to adulteration
Abstract
Introduction
Sample Preparation and vaporization
Solvent-free solid injector vaporization procedures
GC/MS analytical conditions
Volatile compounds emitted from pepper powder
Fig. 2. Schematic diagram of the solvent-free solid injector (SFSI).
In order to distinguish between VOCs generated inhealthy and infected chili powder, SFSI technique wasused.A total of 43 compounds were confirmed in healthy,medium-infected and severely infected chili powder.Trimethylamine and isosorbide were useful asbiomarkers for identifying infected chili and could beused to investigate adulteration in chili powder.The coupling of SFSI-GC/MS was an effectivetechnique for the rapid analysis and characterization ofVOCs in chili power.
Conclusions
To investigate adulteration in commercial chili powder, the volatile organic compounds of healthy and infected powdered chili pepper were characterized using a solvent-free solidinjector (SFSI) coupled with gas chromatography/mass spectrometry (GC/MS). Except for one compound (capillary compound for blank), 43 compounds were identified in healthy andinfected chili powder. Specifically, 31, 36, and 41 compounds were identified in healthy, medium-infected, and severely infected chili powder. Among these compounds, acetic acid(13.77%), propanal (2.477%), N-methylpyrrole (1.986%), and 2-methyl-propanal (1.768%) were leading volatiles in the healthy chili powder. In contrast, infected chili powder contained9,12-octadecadienoic acid, ethyl ester (15.984%), acetic acid (11.249%), hexadecanoic acid, methyl ester (3.3%), N-methylpyrrole (3.221%), and 2-furanmethanol (2.629%) as majorcompounds. Trimethylamine and isosorbide were detected in both medium and severely infected chilli, but not in healthy chili. This means that these compounds could be used asbiomarkers to distinguish between healthy and infected chili. The proposed technique was applied to 12 commercial chili powders, and trimethylamine and isosorbide were detected in sixsamples. These results suggest that a contaminated chili that was added to a healthy one could be successfully identified by a combination of the SFSI and GC/MS.
Keywords: Healthy; Infected; Red pepper powder; Chili; Adulteration; Solid injector; Sample preparation, gas chromatography-mass spectrometry
Objectives
Materials and Methods
Glass crusherSilicone seals
Glass capillary
Outlet of vaporized sample
Supporting bar
(1) (2) (3)
(4) (5) (6)
Fig. 1. Infected red pepper and adulterated red pepper powder.
Fig. 3. Solvent-free solid injector (SFSI) vaporization procedures.
Red pepper powder sample (1 mg)
Put in a soft glass capillary tube
Seal both ends of the tube
Place the tube in a SFSI
Coupled with a GC/MS
Pre-heating time 7 min
GC/MS analysis
Preparation
Vaporization
Results
Fig. 4. Representative gas chromatography/mass spectrometrychromatograms (full scan mode) of the volatile organiccompounds (A) blank sample, (B) healthy, (C) medium-infected, and (D) severely infected (E) commercial chilipowders.
No. RT Compound
Blank Fresh Infected (M)
Infected (H)
Relative area (%)
1 1.721 Propanal - 2.477 2.167 1.160
2 1.773 Trimethylamine - - 0.332 0.473
3 1.861 Acetic acid, methyl ester - 1.345 1.261 0.709
4 2.015 Propanal, 2-methyl- - 1.768 1.412 0.658
5 2.197 2,3-Butanedione - 0.855 1.147 0.359
6 2.270 2-Butanone - 0.641 0.568 0.296
7 2.342 Furan, 2-methyl- - 1.324 0.969 0.443
8 2.827 Acetic acid - 13.777 11.249 7.419
9 2.897 Butanal, 3-methyl- - 1.318 1.154 0.565
10 3.031 Butanal, 2-methyl- - 1.215 0.979 0.493
11 3.182 2-Propanone, 1-hydroxy- - 0.624 0.553 0.402
12 3.506 2,3-Pentanedione - 0.276 0.181 0.115
13 4.489 N,N-Dimethyl-2-aminoethanol - 0.310 0.686 0.606
14 4.629 N-Methylpyrrole - 1.986 3.221 1.631
15 4.894 Pyridine - - 0.125 0.080
16 4.998 Pyrrole - 0.116 0.245 0.238
17 7.200 Pyrazine, methyl- - 0.190 0.324 0.559
18 7.613 Unknown compound 1 - 0.615 0.374 -
19 8.619 2-Furanmethanol - 1.429 2.629 1.221
20 9.083 Unknown compound 2 - 0.576 0.978 0.390
21 10.780 Pyrazine, 2,6-dimethyl- - 0.413 0.392 0.414
22 10.947 Butyrolactone - 1.011 1.297 0.822
23 13.014 2-Furancarboxaldehyde, 5-methyl- - 1.039 0.396 0.085
24 15.813 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- - 0.294 0.303 0.200
25 16.367 2-Pyrrolidinone, 1-methyl- - 0.179 0.496 0.261
26 16.490 Benzeneacetaldehyde - 0.151 - 0.228
27 17.273 Ethanone, 1-(1H-pyrrol-2-yl)- - 0.490 0.568 1.155
28 17.910 2-Pyrrolidinone - - - 0.914
29 18.440 Phenol, 2-methoxy-/Phenol, o-methoxy- - 0.342 0.289 0.866
30 18.734 Acetoglyceride - - - 1.339
31 19.427 Maltol - 1.174 - 0.887
32 20.438 Unknown compound 3 - - 2.122 0.959
33 23.272 1,2-Benzenediol - - 0.352 -
34 26.843 Isosorbide - - 0.539 1.051
35 34.721 2-Propanone, 1-(4-hydroxy-3-methoxyphenyl)- - 0.461 0.379 0.175
36 40.338 Tetradecanoic acid, methyl ester, - - - - 0.302
37 45.874 Hexadecanoic acid, methyl ester - - 0.629 1.340 3.300
38 46.312 Pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl)- - - 0.525 0.430 0.598
39 46.986 Unkown compound 4 - 12.566 1.167 1.116 1.595
40 50.260 9,12-Octadecadienoic acid (Z,Z)-, methyl ester 12.566 - 1.062 3.539 15.984
41 50.323 Unkown compound 5 - - - 1.602 3.994
42 50.866 Octadecanoic acid, methyl ester - - - 0.398 1.108
43 51.757 9,12-Octadecadienoic acid, ethyl ester - - - - 0.751
44 52.242 Hexadecanamide - - - - 0.463
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