| Literature DB >> 28911420 |
Shimin Wu1, Ting Xu2, Casimir C Akoh3.
Abstract
Roasted Trichosanthes kirilowii seeds have much more intense flavor than the raw seeds, and are commonly used as food and in the preparations of many medicinal formulations. Volatile constituents in the raw and roasted T. kirilowii seeds were separated by simultaneous distillation and extraction, and analyzed by gas chromatography-mass spectrometry on two capillary gas chromatography columns of different polarities (DB-WAX and HP-1). A total of 40 volatile compounds were identified in the raw seeds, with pentanal, 2-pentanol, styrene, (Z)-2-heptenal, (+)-calarene, and α-muurolene being the predominant compounds; 40 volatile compounds were also identified in the roasted seeds, with 3-methylbutanal, ethanol, 2-butanol, 2,3-butanediol, (E,E)-2,4-nonadienal, and 2-isopropyl-5-methyl-9-methylene-bicyclo[4.4.0]dec-1-ene being the most abundant compounds. A total of 15 compounds, mostly aldehydes, were common in both seeds. Roasting of T. kirilowii seeds resulted in a significant decrease in the levels of sesquiterpenes and short-chain aliphatic aldehydes. By contrast, high concentrations of 3-methylbutanal, ethanol, 2-butanol, and alkyl pyrazines were generated, which was responsible for the unique flavor of the roasted seeds. The study results may be useful for optimizing the roasting process and oil processing of T. kirilowii seeds.Entities:
Keywords: Pyrazines; Roasting; Sesquiterpenes; Trichosanthes kirilowii seeds; Volatile compounds
Year: 2014 PMID: 28911420 PMCID: PMC9354876 DOI: 10.1016/j.jfda.2013.12.005
Source DB: PubMed Journal: J Food Drug Anal Impact factor: 6.157
Volatile constituents of raw Trichosanthes kirilowii seeds.
| No. | Compounds | Retention indices | Identification | Percentage of total area (%) | |
|---|---|---|---|---|---|
|
| |||||
| DB-WAX | HP-1 | ||||
| 1 | 1-(1-Methylethyl)-cyclopentene | 927 | n.d. | C | 0.69 |
| 2 | Pentanal | 984 | <700 | A | 19.84 |
| 3 | 2-Methyl-butanoic acid ethyl ester | 1059 | 841 | A | 2.84 |
| 4 | Hexanal | 1086 | 779 | A | 4.08 |
| 5 | Undecane | 1099 | 1099 | A | 0.39 |
| 6 | 3-Pentanol | 1110 | <700 | A | 1.93 |
| 7 | 2-Pentanol | 1124 | <700 | A | 6.39 |
| 8 | ( | 1161 | 811 | B | 0.55 |
| 9 | 3-Methyl-2-butenal | 1199 | 750 | A | 0.54 |
| 10 | 3-Methyl-1-butanol | 1209 | 718 | A | 0.91 |
| 11 | ( | 1219 | 829 | A | 0.50 |
| 12 | 2-Pentyl-furan | 1236 | 977 | A | 0.46 |
| 13 | 1-Pentanol | 1254 | 752 | A | 2.03 |
| 14 | Styrene | 1260 | 875 | A | 6.58 |
| 15 | ( | 1324 | 932 | A | 7.72 |
| 16 | 6-Methyl-5-hepten-2-one | 1341 | n.d. | C | 0.28 |
| 17 | 1-Hexanol | 1356 | 872 | A | 0.40 |
| 18 | 2,2-Dimethyl-propanoic acid heptyl ester | 1390 | 1260 | B | 0.33 |
| 19 | Nonanal | 1394 | 1084 | A | 0.38 |
| 20 | ( | 1430 | 1028 | A | 0.30 |
| 21 | 1-Octen-3-ol | 1455 | 966 | A | 0.33 |
| 22 | Acetic acid | 1458 | <700 | A | 0.41 |
| 23 | Copaene | 1486 | 1370 | B | 2.77 |
| 24 | Benzaldehyde | 1521 | 933 | A | 0.85 |
| 25 | β-Cubebene | 1535 | 1419 | B | 0.42 |
| 26 | (+)-Calarene | 1585 | 1440 | A | 16.59 |
| 27 | ( | 1643 | 1238 | A | 0.45 |
| 28 | Acetophenone | 1648 | 1034 | B | 0.75 |
| 29 | 2,4-Nonadienal | 1663 | 1169 | B | 1.64 |
| 30 | 2-Hydroxybenzaldehyde | 1675 | 1009 | A | 1.22 |
| 31 | Germacrene D | 1683 | 1469 | A | 0.75 |
| 32 | ( | 1699 | 1185 | A | 4.49 |
| 33 | α-Muurolene | 1719 | 1487 | B | 5.93 |
| 34 | Cadina-1(10),4-diene | 1753 | 1514 | B | 0.29 |
| 35 | ( | 1765 | 1269 | A | 0.34 |
| 36 | 2,4-Decadienal | 1808 | 1288 | A | 1.41 |
| 37 | Benzyl alcohol | 1875 | 1031 | A | 0.81 |
| 38 | β-Ionol | 1936 | 1401 | B | 0.48 |
| 39 | δ-Cadinol | 2193 | 1623 | B | 0.48 |
| 40 | 2,3-Dihydrobenzofuran | 2391 | 1224 | A | 1.13 |
n.d. = not detected.
The reliability of the proposed identification has been indicated according to the following: A, mass spectrum and retention indices on both the polar and nonpolar columns agreed with those of the standards, computer database, and literature; B, mass spectrum and retention indices on both the polar and nonpolar columns agreed with values from the computer database and the literature; C, mass spectrum and retention index on a polar column agreed with the values from the computer database and the literature.
Volatile constituents of roasted Trichosanthes kirilowii seeds.
| No. | Compounds | Retention indices | Identification | Percentage of total area (%) | |
|---|---|---|---|---|---|
|
| |||||
| DB-WAX | HP-1 | ||||
| 1 | 3-Methylbutanal | 923 | <700 | A | 7.60 |
| 2 | Ethanol | 940 | <7002 | A | 10.58 |
| 3 | Pentanal | 984 | <700 | A | 4.28 |
| 4 | 2-Butanol | 1030 | <700 | A | 11.67 |
| 5 | Hexanal | 1085 | 779 | A | 1.52 |
| 6 | 2-Ethoxy-propane | 1092 | <700 | B | 0.44 |
| 7 | 2-Pentanol | 1123 | <700 | A | 0.48 |
| 8 | 2-Ethoxy-butane | 1153 | <700 | B | 2.07 |
| 9 | 2-Heptanone | 1184 | 873 | A | 0.41 |
| 10 | 4-Methyl-2-pentanol | 1199 | 739 | A | 0.50 |
| 11 | 2-Hexanol | 1210 | 779 | A | 0.44 |
| 12 | 1-Pentanol | 1254 | 752 | A | 0.37 |
| 13 | 3-Hydroxy-2-butanone | 1285 | <700 | A | 4.35 |
| 14 | 2-Heptanol | 1306 | 889 | A | 1.13 |
| 15 | 2,5-Dimethyl-pyrazine | 1320 | 885 | A | 1.41 |
| 16 | ( | 1324 | 932 | A | 1.33 |
| 17 | 2-Ethyl-5-methyl-pyrazine | 1383 | 970 | A | 0.60 |
| 18 | 2-Ethyl-6-methyl-pyrazine | 1389 | 977 | A | 1.14 |
| 19 | Nonanal | 1394 | 1083 | A | 0.43 |
| 20 | 2,3,5-Trimethyl-pyrazine | 1399 | 980 | A | 1.67 |
| 21 | 3-Ethyl-2,5-dimethyl-pyrazine | 1444 | 1056 | A | 2.20 |
| 22 | Acetic acid | 1457 | <700 | A | 0.93 |
| 23 | 2-Ethyl-3,5-dimethyl-pyrazine | 1460 | 1060 | A | 0.60 |
| 24 | Copaene | 1486 | 1370 | B | 1.46 |
| 25 | 2,3,5-Trimethyl-6-ethylpyrazine | 1491 | 1135 | B | 1.02 |
| 26 | Pyrrole | 1518 | 743 | A | 0.36 |
| 27 | Benzaldehyde | 1521 | 928 | A | 0.45 |
| 28 | 2-Methyl-5-(2-propenyl)-pyrazine | 1537 | 1073 | B | 0.52 |
| 29 | 2,3-Butanediol | 1541 | 806 | B | 5.18 |
| 30 | 2-Isopropyl-5-methyl-9-methylene-bicyclo[4.4.0]dec-1-ene | 1584 | 1419 | B | 7.35 |
| 31 | Benzeneacetaldehyde | 1643 | 1005 | A | 2.09 |
| 32 | Acetophenone | 1648 | 1034 | B | 0.69 |
| 33 | 2,4-Nonadienal | 1663 | 1168 | A | 1.45 |
| 34 | ( | 1698 | 1184 | A | 5.50 |
| 35 | α-Amorphene | 1719 | 1487 | B | 2.82 |
| 36 | ( | 1765 | 1269 | A | 0.49 |
| 37 | 2,4-Decadienal | 1808 | 1287 | A | 1.54 |
| 38 | Benzothiazole | 1948 | 1185 | B | 1.68 |
| 39 | 2-Methoxy-4-vinylphenol | 2193 | 1278 | B | 0.39 |
| 40 | 2,3-Dihydrobenzofuran | 2390 | 1224 | A | 0.72 |
n.d. = not detected.
The reliability of the proposed identification has been indicated according to the following: A, mass spectrum and retention indices on both polar and nonpolar columns agreed with those of the standards, computer database, and literature; B, mass spectrum and retention indices on both polar and nonpolar columns agreed with values from the computer database and the literature; C, mass spectrum and retention index on a polar column agreed with the values from the computer database and the literature.
Fig. 1Typical gas chromatography–mass spectrometry chromatograms of volatile constituents from the (A) raw and (B) roasted Trichosanthes kirilowii seeds. The number of major compounds and the peak identification are shown in Tables 1 and 2.
Quantitative comparison on disappearance, decrease, and generation of volatile classes and most abundant compounds between the raw and roasted Trichosanthes kirilowii seeds.
| Chemical classes | Relative amount (%) | Decreasing/increasing times | |
|---|---|---|---|
|
| |||
| Raw seeds | Roasted seeds | ||
| Aldehydes | 44.31 | 26.68 | −1.66 |
| Predominant three aldehydes | 31.60 | 17.38 | −1.82 |
| Alcohols | 13.76 | 30.35 | +2.21 |
| Predominant three alcohols | 10.35 | 27.43 | +2.65 |
| Hydrocarbons | 34.41 | 11.63 | −2.96 |
| Sesquiterpenes | 26.75 | 11.63 | −2.30 |
| Heterocyclic compounds | 1.59 | 11.32 | +7.12 |
| Pyrazines | n.d. | 9.16 | n |
| Esters | 3.17 | n.d. | d |
| Acids | 0.41 | 0.93 | +2.27 |
| Ketones | 1.03 | 1.10 | +1.07 |
| Ethers | n.d. | 2.51 | n |
n.d. = not detected.
Times were calculated using the bigger relative amount divided by the smaller relative amount. The symbols +, −, n, and d denote increasing, decreasing, newly generated, and disappeared, respectively.
The predominant three aldehydes were pentanal, (Z)-2-heptenal, and (E,E)-2,4-nonadienal for the raw seeds, and 3-methylbutanal, (E,E)-2,4-nonadienal, and pentanal for the roasted seeds.
The predominant three alcohols were 2-pentanol, 1-pentanol, and 3-pentanol for the raw seeds, and ethanol, 2-butanol, and 2,3-butanediol for the roasted seeds.