The Chemical Composition of Cumin (Cuminum cyminum L.) Analyzed by UPLC-Q-Orbitrap MS and GC-MS

Abstract

Objective: Cumin (Cuminum cyminum L.) is an important spice widely used as a functional food and in traditional Chinese medicine. However, its chemical constituents have not been systematically reported. This study aimed to identify and analyze the chemical composition of its aqueous extracts and volatile oils. Methods: The chemical composition of cumin was systematically analyzed using ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-Orbitrap-MS) and gas chromatography-mass spectrometry (GC-MS). Results: A total of 102 compounds were identified in cumin. Of these, 62 were found in the aqueous extract, including 10 flavonoids, 7 phenylpropanoids, 5 terpenoids, 4 alkaloids, 7 organic acids, 8 fatty acids, 8 amino acids, 2 glycosides, and 10 other components. In addition, 40 compounds were characterized in the volatile oil, accounting for 98.70% of the total volatile content. These compounds include monoterpenes, sesquiterpenes, alkanes, alcohols, aldehydes, phenols, ketones, and alkylbenzenes. Conclusion: These findings expand our understanding of the chemical composition of cumin and provide a foundation for elucidating its pharmacodynamic properties.

Keywords

aqueous extract volatile oil chemical composition UPLC-Q-Orbitrap-MS GC-MS

Introduction

Cumin (Cuminum cyminum L.) is an annual or biennial plant of the genus Cuminum in the family Umbelliferae which widely distributed in India, North America, Russia, and China, with India being the largest producer of cumin in the world.¹ It is used both as a functional food and as a Traditional Chinese Medicine (TCM) (Figure 1). Cumin is a popular spice due to its rich and unique aroma. It is used in food, beverages, pharmaceuticals, perfumes and toiletries.^2,3

Figure 1.

Plant diagram A and medicinal materials diagram (seed) B of Cuminum cyminum L.

As a TCM, the medicinal properties of cumin are warm and the flavor is pungent. It has been used to treat stomach pain, dyspepsia, flatulence, hoarseness, toothache, hypertension, scorpion bites, weight loss, jaundice and diarrhoea.^2,4 It can be administered alone or in combination with other Chinese herbs.² Moreover, modern research has demonstrated various pharmacological effects of cumin, including antioxidant, antibacterial, insect-killing, anti-inflammatory, pain-relieving, antitumor, platelet disaggregating, and antiallergic activities^3,5 as well as, tension-preventive, hyperglycemic, hypoglycemic, antihyperlipidemic, bronchodilatory, immunomodulatory, contraceptive, anti-amyloidogenic,⁶ anti-osteoporotic, antifungal, aldose reductase, alpha-glucosidase,⁷ tyrosinase inhibitory, and neurovs protective properties.⁸ Relevant studies also indicate that cumin lowers blood glucose in diabetic rats and reduces plasma and tissue levels of cholesterol, phospholipids, free fatty acids, and triglycerides.^6,7,9

The primary reason cumin may help treat diseases is its close link between chemical composition and pharmacological effects. Cumin contains about 10% fatty oil, volatile oil, protein, cellulose, sugar, minerals, and elements.^10–12 Its volatile oils have been extensively studied, which cuminaldehyde identified as the major bioactive component.¹³ Additional constituents include cymene, cuminic alcohol (cuminol), γ-terpinene, safranal, limonene, eugenol, β-myrcene, α-phellandrene, β-phellandrene, and β-pinene.^11,14 To date, most research has focused on these volatile oil components,^15–17 whereas relatively little attention has been paid to the macro-polar constituents in its aqueous extract. Hence, a systematic and comprehensive analysis of its chemical composition is warranted to clarify its pharmacodynamic material basis. In this study, the aqueous extract and volatile oil of cumin were analyzed by UPLC-Q-Orbitrap MS and GC-MS to provide a complete overview of its chemical constituents. These data will aid in consistency evaluation and quality control of cumin, serving as an important reference for its development as a traditional medicine and functional food.

Materials and Methods

Instrument

Q Exactive Plus Orbitrap High Resolution LMS (Thermo Fisher), U3000 Ultra High Performance Liquid Chromatography and Automatic Sampler (Thermo Fisher), ACQUITY UPLC HSS T3, 2.1 × 100 mm, 1.8 μm column (Waters Company), Agilent 7890A gas chromatograph combined with a 7000B triple-quadrupole MS detector (Agilent, Palo Alto, CA, USA), HP-5MS capillary column (30 m × 0.25 mm ×0.25 μm), Vortex 2 Genie Vortex Mixer (Scientific Industries), 5810R Low temperature centrifuge (Eppendorf), WD-9415C ultrasonic cleaner (Beijing Liuyi Instrument Factory), AL 204 Electronic Analytical Balance (Mettler-Toledo, USA), KQ-250 Ultrasonic Cleaner (Gong Yu hua Instrument Co., Ltd); Genie G10 (C111) Ultrapure water preparation device (Inner Mongolia Jingding Yuanye Technology Co., LTD, China).

Drugs and Reagents

Drugs. Cumin were purchased from the Inner Mongolia Tianli Pharmaceutical Co., LTD in 2023 (Place of origin: Xinjiang, No.: 20231022). It was identified as the mature fruit of Cuminum cyminum L. by Professor Tumen Bayar from the Teaching and Research Department of Mongolian Medicine, College of Mongolian Medicine, Inner Mongolia Medical University.

Reagents. Methanol and formic acid were purchased from Thermo Fisher (Pittsburg, PA, USA). Deionized water was produced using the Milli Q Advantage A10 ultrapure water machine. n-Hexane was purchased by Tianjin Fuyu Fine Chemical Co., Ld

Sample Solution Preparation

Preparation of aqueous extract: Cumin powder (25 g) was placed in an Erlenmeyer flask with 1000 mL of distilled water and boiled for 30 min on a hot plate with constant stirring. The resulting solution was filtered with a muslin cloth, concentrated and dried completely at 60 °C in an oven. For qualitative analysis, 10.00 mg of aqueous cumin extract was diluted in 10 ml of 50% methanol, ultrasonic treatment for 30 min, centrifuged at 13000 r • min⁻¹ and the supernatant was collected for later use.

Extraction of volatile oil : Weigh 50 g of cumin powder, put it in a round bottom flask, shake and mix with 10 times water, soak and gently to boiling and maintain the micro boiling until the specified time, stop heating, place to cool the proportion of the volatile oil and calculate its yield volatile oil yield. The return was 2.5%. The extracted volatile oil was collected, dried with anhydrous sodium sulfate and then stored in the refrigerator at 4 °C. Take 1 ml of volatile oil and make it up to 10 ml with n-hexane for analysis.

UPLC-Q-Orbitrap-MS Analysis Conditions

Instrumentation and Conditions

The chromatographic separations were performed using a Waters ACQUITY UPLC HSS T3 C₁₈ column (2.1 mm × 100 mm, 1.8 μm). The flow rate was set at 0.2 mL/min. The injection volume of the samples was 10 µL. The mobile phase was composed of solvent A (ultrapure water with 0.1% formic acid) and solvent B (acetonitrile). The gradient program was as follows: 0 min, 100% A; 0∼10 min, 100→70% A; 10∼25 min, 70→60% A; 25∼30 min, 60→50%A; 30∼40 min, 50→30% A; 40∼45 min, 30→0%A; 45∼60 min, 0→100% A; 60∼70 min, 100% A.

Mass spectrometric detection was conducted on the Q Exactive PlusTM Orbitrap MS system. The detection mode is Full MS-ddMS2, positive and negative ion modes are scanned simultaneously, and the scanning range is m/z 100–1200. The other parameters were set as follows: MS1 resolution set to 70,000, MS2 resolution set to 17500, capillary voltage was 3.2 kV, capillary temperature was set to 320°C, Aux gas heater temperature was set to 350°C, Sheath gas flow rate was 40L/min, Aux gas flow rate was 15L/min, AGC Target set to 1e6, TopN was set to 5, and the collision energy triggering the MS2 scan adopts the stepped fragmentation voltage NCE, which is set to 30, 40, 50.

Data Analysis and Identification of Compounds

The chromatographic peak identification was implemented, comparing the chromatographic retention time, excimer ion peak and fragment-ion of the test sample with the standard sample, compounds with scores greater than 80 were screened by mzCloud (www.mz-cloud.com) and mzVoult (self-made database) software. Combined with the literature reports on the relevant chemical components of cumin, in the light of the exact molecular weight provided by mass spectrometry, calculated the accurate molecular formula of components, determined and assigned to each component peak. The maximum mass errors between the measured and calculated values were < 5 ppm, and the matching compounds would be generated from predicted fragments from the structure. Further analysis of the compounds was conducted by considering relevant literature and utilizing online databases such as PubChem, CNKI and PubMed.

GC-MS Analysis Conditions

Instrumentation and Conditions

The GC-MS analysis volatile oil were measured on HP-5MS capillary column (30 m × 0.25 mm ×0.25 μm) was adopted for the chromatographic separation. Helium gas was used as carrier gas at a constant flow rate of 1 ml/min and an injection volume of 1 μl in size ratio of 10:1. The ion source temperature was 270°C. The temperature program employed was as follows: starting at 40°C for 1 min, then ramping to 60°C at a rate of 5°C/min, followed by an increase to 100°C at a rate of 8°C/min, and finally reaching 280°C at a rate of 10°C/min, with a hold time of 3 min. The electron ionization (EI) source was utilized for ionization, with the analysis being ionized at 70 eV and 230°C in the ion source and solvent delay was 5 min. The scanning mass range was set from 40 to 650.

Data Analysis and Identification of Compounds

The raw data files were imported into Qualitative Analysis 10.0 software for further analysis. Peak integration and mass spectra extraction were performed using this software. The extracted mass spectra were compared to the NIST standard library for identification. Additionally, the raw data was subjected to peak extraction and peak alignment. The compounds were identified by combining relevant literature and utilizing online databases. Then, find the Kovats retention Index (RI) of the obtained volatile components from NIST (National Institute of Standards and Technology) to further identify and verify their volatile components.

Statistic Analysis

All Data was processed and summarized using Microsoft Office Excel 2019. The Pie Chart was made using Microsoft Office Word 2019. Bar chart was drawn with Wei Sheng Xin (https://www.bioinformatics.com.cn/).

Results

UPLC-Q-Orbitrap MS Analysis of Chemical Components from Cumin Aqueous Extraction

The high resolution MS data of cumin aqueous extract were rapidly acquired using the UPLC-Q-Orbitrap-MS method. 62 compounds were systematically identified from the aqueous extract of cumin using UPLC-Q-TOF-MS in positive and negative ion modes. The total ion chromatogram was analyzed by the standards, fragmentation patterns, literature, mzCloud and mzVault database (Figure 2, Table 1). These including 10 flavonoids, 7 phenylpropanoids, 5 terpenoids, 4 alkaloids, 7 organic acids, 8 fatty acids, 8 amino acids, 2 glycosides and 10 other components. The proportion of different types of compounds is shown in Figure 3. Furthermore, representative compositions of these different chemical types were used as examples to analyze the possible fragmentation pathways and characteristic products, in conjunction with reported literature.

Figure 2.

Total ion current chromatograms of cumin aqueous extract under positive (A) and negative (B) ion modes.

Figure 3.

Types of compounds contained in cumin aqueous extract.

Table 1.

Identification of Chemical Constituents of Cumin Aqueous Extract by UPLC-Q-TOF-MS.

NO.	t_R/min	Formula	PPM	Parentions, m/z	Fragment ions, m/z	Identification	Adduction	Classification	references
1	1.414	C₆H₁₄O₆	0.23	181.07181	89.0243, 73.0294, 71.0137	D-(-)-Mannitol	[M-H]⁻¹	Glycosides	¹⁸
2	1.462	C₆H₁₂O₆	−0.62	179.0560	87.0086, 71.0137, 59.0137	D-(+)-Galactose	[M-H]⁻¹	Glycosides	¹⁹
3	1.502	C₅H₁₁NO₂	0.50	118.08633	69.0663, 59.0733	Betaine	[M + H] ^+ 1	Alkaloids	²⁰
4	1.542	C₄H₆O₅	−0.30	133.01421	133.0144, 115.0036, 89.0241, 71.0137	L-(-)-Malic acid	[M-H]⁻¹	Organic acid	²¹
5	1.545	C₄H₄O₄	−1.22	115.00354	71.0137	Fumaric acid	[M-H]⁻¹	Organic acid	²²
6	1.553	C₆H₆O₆	−0.74	173.00903	173.0091, 67.0188	trans-Aconitic acid	[M-H]⁻¹	Fatty acid	²²
7	1.569	C₆H₈O₇	0.26	191.01978	173.0092, 129.0193, 111.0087, 87.0087	Isocitric acid	[M-H]⁻¹	Organic acid	¹⁸
8	1.605	C₅H₄O₃	−1.03	111.00865	67.0188	2-Furoic acid	[M-H]⁻¹	Organic acid	²³
9	1.767	C₅H₇NO₃	0.58	130.05000	130.0499, 84.0444	Pyroglutamic acid	[M + H] ^+ 1	Amino acid	²²
10	2.413	C₆H₁₁NO₂	0.85	130.08636	130.0864, 70.0653	Pipecolic acid	[M + H] ^+ 1	Amino acid	²²
11	2.709	C₆H₅NO₂	1.19	124.03945	80.0495	Nicotinic acid	[M + H] ^+ 1	Others	²²
12	2.784	C₅H₅N₅	0.92	136.0619	136.0618, 91.0542	Adenine	[M + H] ^+ 1	Others	²⁴
13	2.785	C₄H₅N₃O	0.74	112.0506	112.0505, 95.0240, 69.0448	Cytosine	[M + H] ^+ 1	Others	²⁵
14	3.178	C₆H₆N₂O	0.88	123.0554	105.0448, 96.0444, 95.0492, 78.0339	Nicotinamide	[M + H] ^+ 1	Others	¹⁸
15	3.472	C₅H₇NO₃	0.54	130.0500	85.0478, 84.0444	L-Pyroglutamic acid	[M + H] ^+ 1	Amino acid	²³
16	3.611	C₇H₁₃NO₂	1.02	144.1021	84.0808	DL-Stachydrine	[M + H] ^+ 1	Alkaloids	²³
17	3.629	C₅H₄N₄O₃	−0.04	167.0210	167.0210, 96.0202	Uric acid	[M-H]⁻¹	Others	²²
18	4.259	C₆H₁₃NO₂	0.76	132.1020	86.0965, 69.0702	L-Norleucine	[M + H] ^+ 1	Amino acid	²⁶
19	4.978	C₉H₁₁NO₃	1.22	182.0814	182.0816, 147.0440,136.0757, 123.0440, 119.0492	L-Tyrosine	[M + H] ^+ 1	Amino acid	²¹
20	5.583	C₁₀H₁₃N₅O₄	0.36	268.1041	268.0137, 136.0618	Adenosine	[M + H] ^+ 1	Others	²¹
21	5.739	C₅H₅N₅O	0.71	152.0568	135.0301, 110.0348	Guanine	[M + H] ^+ 1	Others	²⁷
22	6.319	C₉H₁₁NO₂	0.86	166.0864	166.0859, 120.0808, 103.0542, 91.0541	L-Phenylalanine	[M + H] ^+ 1	Amino acid	²⁸
23	7.362	C₇H₆O₄	−0.29	153.0193	153.0193, 109.0294, 108.0215	2,3-Dihydroxybenzoic acid	[M-H]⁻¹	Phenylpropanoids	²¹
24	7.894	C₁₁H₉NO₂	0.31	188.0707	170.0599, 146.0599, 118.0650	trans-3-Indoleacrylic acid	[M + H] ^+ 1	Organic acid	²³
25	7.894	C₁₁H₁₂N₂O₂	0.29	205.0972	188.0705, 170.0595, 118.0651	Tryptophan	[M + H] ^+ 1	Amino acid	²⁷
26	8.487	C₇H₁₂O₅	-0.48	175.0611	131.0713, 115.0399, 85.0657	2-Isopropylmalic acid	[M-H]⁻¹	Organic acid	²³
27	8.488	C₁₀H₁₀O₄	-0.29	193.0506	193.0506, 149.0607, 93.0344	Ferulic acid	[M-H]⁻¹	Phenylpropanoids	²⁹
28	8.773	C₉H₆O₂	0.5	147.0441	147.0440, 103.0542	Coumarin	[M + H] ^+ 1	Phenylpropanoids	³⁰
29	8.776	C₉H₈O₃	0.15	163.0400	119.0501, 92.9957	3-Coumaric acid	[M-H]⁻¹	Phenylpropanoids	²³
30	8.944	C₇H₁₂O₆	-0.26	191.0561	127.0399, 109.0294, 93.0343	D-(-)-Quinic acid	[M-H]⁻¹	Phenylpropanoids	²⁰
31	8.952	C₁₁H₉NO₂	0.31	188.0707	188.0706	Indole-3-acrylic acid	[M + H] ^+ 1	Alkaloids	³⁰
32	8.962	C₁₆H₁₈O₉	-0.12	353.0877	353.0877, 191.0554, 135.0442	Chlorogenic acid	[M-H]⁻¹	Phenylpropanoids	^29,31
33	9.618	C₂₇H₃₀O₁₅	0.63	593.1516	473.1091, 353.0667	Vicenin II	[M-H]⁻¹	Flavonoids	²⁰
34	9.704	C₁₇H₂₀N₄O₆	0.02	377.1456	243.0877, 200.0820, 172.0869, 99.0442	Riboflavin	[M + H] ^+ 1	Alkaloids	²³
35	10.069	C₈H₁₅NO₃	-0.27	172.0979	130.0872, 111.0086	N-Acetyl-L-leucine	[M-H]⁻¹	Amino acid	²³
36	10.074	C₆H₁₂O₃	-0.94	131.0712	85.0657, 69.0345	2-Hydroxy-4-methylpentanoic acid	[M-H]⁻¹	Organic acid	²³
37	10.207	C₇H₆O₂	-0.64	121.0294	108.0216, 91.0187	Benzoic acid	[M-H]⁻¹	Phenylpropanoids	²³
38	11.512	C₁₆H₁₂O₆	-1.38	301.0703	286.0470, 258.0521, 229.0491, 153.0183	Diosmetin	[M + H] ^+ 1	Flavonoids	³²
39	11.743	C₂₁H₂₀O₁₁	-0.05	449.1078	153.0183	Cynaroside	[M + H] ^+ 1	Flavonoids	³³
40	12.699	C₂₁H₂₀O₁₀	-0.22	433.1129	271.0600	Apigetrin	[M + H] ^+ 1	Flavonoids	³⁴
41	12.759	C₂₁H₂₀O₁₁	0.02	447.0933	447.0925	Kaempferol-7-O-glucoside	[M-H]⁻¹	Flavonoids	²¹
42	12.95	C₂₂H₂₂O₁₁	0.25	463.1234	301.0705, 286.0470	Diosmetin-7-O-β-D-glucopyranoside	[M + H] ^+ 1	Flavonoids	³⁵
43	13.001	C₉H₁₆O₄	0.07	187.0976	187.0977, 143.0176, 125.0971, 97.0658	Azelaic acid	[M-H]⁻¹	Fatty acid	^21,22
44	13.055	C₂₁H₂₀O₁₀	-0.16	433.1129	271.0599, 153.0181, 119.0491	Apigenin-7-O-β-D-glucoside	[M + H] ^+ 1	Flavonoids	¹⁸
45	13.799	C₁₅H₂₀O₂	-0.51	233.1535	215.1429, 187.1481, 159.1168, 131.0855, 105.0699	Isoalantolactone	[M + H] ^+ 1	Terpenoids	²³
46	15.793	C₁₅H₂₂O	-0.68	219.1742	219.1742, 201.1638, 163.1117, 159.1169, 121.1012	Germacrone	[M + H] ^+ 1	Terpenoids	³⁶
47	15.85	C₁₅H₁₀O₆	-0.32	285.0404	285.0405, 241.0500, 151.0035, 133.0294, 107.0137	Luteolin	[M-H]⁻¹	Flavonoids	³³
48	18.688	C₁₅H₁₀O₅	-0.43	269.0455	269.0457, 225.0555, 201.0552, 181.0659, 159.0450, 151.0036, 117.0345, 107.0137	Apigenin	[M-H]⁻¹	Flavonoids	^33,37
49	18.533	C₁₅ H₂₀ O₃	0.22	249.1486	105.0699	Parthenolide	[M + H] ^+ 1	Terpenoids	³²
50	19.468	C₁₆H₁₂O₆	0.05	299.0562	284.0326, 256.0377, 227.0352, 151.0033	Diosmetin	[M-H]⁻¹	Flavonoids	²⁰
51	20.806	C₁₈H₃₄O₅	0.07	329.2334	229.1445, 211.1339, 171.1026, 139.1128, 99.0814	(15Z)-9,12,13-Trihydroxy-15-octadecenoic acid	[M-H]⁻¹	Fatty acid	²³
52	20.807	C₁₈H₃₀O₃	-0.71	295.2266	277.2161, 161.1322, 93.0700, 81.0700	9-Oxo-ODE (octadecadienoic acid)	[M + H] ^+ 1	Fatty acid	²³
53	29.191	C₁₇H₂₄O₃	-0.37	277.1797	249.1849, 241.1582, 231.1742	Shogaol	[M + H] ^+ 1	Others	³⁸
54	33.744	C₁₅H₂₂O₂	-0.03	235.1693	190.1589, 161.0960	Artemisinic acid	[M + H] ^+ 1	Terpenoids	²³
55	34.732	C₁₈H₃₄O₄	1.02	313.2386	201.1132, 171.1025, 127.1127	(+/-)9,10-dihydroxy-12Z-octadecenoic acid	[M-H]⁻¹	Fatty acid	²³
56	34.741	C₁₅H₂₀O₂	-0.51	233.1535	233.1534, 215.1429, 145.1011, 131.0856, 105.0700	Atractylenolide II	[M + H] ^+ 1	Terpenoids	²⁴
57	39.753	C₁₈H₃₀O₂	-0.16	279.2318	243.2115, 95.0856, 81.0700	α-Eleostearic acid	[M + H] ^+ 1	Fatty acid	²³
58	39.809	C₁₅H₂₂O₂	-0.06	235.1693	217.1587, 189.1638, 133.1012	Curcumenol	[M + H] ^+ 1	Terpenoids	³⁷
59	41.297	C₁₆H₃₃NO	-0.13	256.2635	102.0914, 88.0757	Hexadecanamide	[M + H] ^+ 1	Others	²⁴
60	47.419	C₁₈H₃₇NO	-0.29	284.2947	88.0757	Stearamide	[M + H] ^+ 1	Fatty acid	²⁴
61	48.487	C₁₈H₃₄O₂	0.09	281.2486	263.2375	Elaidic acid	[M-H]⁻¹	Fatty acid	²⁴
62	50.723	C₂₂H₄₃NO	-0.73	338.3415	135.1168, 83.0856	Erucamide	[M + H] ^+ 1	Others	²⁴

Flavonoids

There were two types of flavonoids including flavonoid aglycone compounds and flavonoid glycoside compounds. It is well known that the main MS behavior of flavonoid aglycones was RDA fragmentation pathway and losses of small molecules or radicals^39,40 like -CH₃, -CO, -CO₂, -CH₂ and -H₂O. For flavonoid glycosides, the cleavage at glycosidic linkages could happen in both positive and negative ion modes, that is mainly forms high-abundance flavonoid aglycones by continuously losing sugar groups.^41,42 We identified the 10 flavonoids, here took apigenin and luteolin as examples to describe the fragment patterns and possible fragmentation pathways of these components, respectively. Using negative ion mode, compound 48 exhibited a [M-H]⁻ signal at m/z 269.0455. The possible elemental composition of the compound is C₁₅H₁₀O₅, and the main fragment ions include m/z 225.0555, 201.0552, 181.0659, 159.0405, 117.0345, etc, in which m/z 225.0555 is derived from the loss of a neutral CO₂ molecule at the excimer ion peak and then the loss of a CO₂ to m/z 181.0659 fragment ion. The m/z 201.0552 ions are derived by hydrogen rearrangement after the loss of excimer ion peaking C₃O₂, but its structure is unstable and easy to lose C₂H₂O to form a stable conjugated ion m/z 159.0405, and m/z 159.0405 can lose C₂H₂O to form fragmentation ion m/z 117.0345. The fragment information is basically consistent with the literature report 50. So it was identified as the compound is apigenin. The secondary mass spectrum and possible cleavage pathway was shown in Figure 4A. Compound 47 exhibited a [M-H]⁻ signal at m/z 285.0404, the cleavage fragments of RDA from the flavonoid mother nucleus were also founded at m/z 151.0035 and m/z 133.0294 fragments. Its C the loss of CO and O in the ring results in a characteristic ion fragment³³ m/z 241.0500. Through database search, it is speculated that the compound is luteolin. The secondary mass spectrum and possible cleavage pathway was shown in Figure 4B.

Figure 4.

The secondary mass Spectrum and possible cleavage pathway of apigenin (A) and luteolin (B).

Phenylpropanoids

A total of 7 phenylpropanoids were identified. The cleavage characteristics of secondary mass spectrometry were mainly the loss of neutral molecules such as H₂O, CH₂O₂ and CO₂. Here took chlorogenic acid was taken as example to describe the fragment patterns and possible fragmentation pathways of these components.⁴² Using negative ion mode, compound 32 exhibited a [M-H]⁻ signal at m/z 353.0877, the possible elemental composition of the compound is C₁₆H₁₈O_9. In the secondary mass spectra, the fragment ion m/z 191.0554 [M-H-C₉H₆O₃]⁻ was formed after losing the quinic acid component, or the fragment ion m/z 135.0452 [M-H-C₇H₁₀O₅-CO₂]⁻ was formed after losing the caffeic acid component and then further losing CO₂. The cleavage pathway of the compound was consistent with that reported in the literature.³⁷ Compound 54 was identified as chlorogenic acid and its possible cleavage pathway is shown in Figure 5.

Figure 5.

The secondary mass Spectrum and possible cleavage pathway of chlorogenic acid.

Amino Acids

Amino acids are a class of compounds containing amino and carboxyl groups. Generally, the characteristic fragments of the parent ions H₂O and COOH₂ corresponding to 18 and 46 are lost,^43,44 and some amino acids will lose NH₃ corresponding to 17. In this study, we have identified the 8 amino acids, here took L-Tyrosine as an example, to describe the fragment patterns and possible fragmentation pathways of these components. The molecular ion peak given by quasi-positive ions is m/z 182.0816 [M + H]⁺, the possible elemental composition of the compound is C₉H₁₁NO₃, and the ion fragments are 136.0757 [M + H-CH₂O₂]⁺ and 119.0492 [M + H-CH₂O₂-NH₃]⁺ respectively. Therefore, combined with mass spectrometry information and related literature,^21,45 it was speculated that it may be L-Tyrosine. The specific secondary spectrum and possible cleavage pathway is shown in Figure 6.

Figure 6.

The secondary mass Spectrum and possible cleavage pathways of L-tyrosine.

Terpenoids

A total of 5 terpenoids were identified. The lactone ring cracking is the most basic cleavage pathway in the mass spectrometry behavior of lactone compounds. In ESI multistage mass spectrometry, the lactone ring is opened first, CO₂, H₂ is removed, and then C₂H₄, C₃H₆ are lost step by step.⁴ Here took germacrone as example to describe the fragment patterns and possible fragmentation pathways of these components. Using positive ion mode, compound 46 exhibited a [M + H]⁺ signal at m/z 219.1742, the possible elemental composition of the compound is C₁₅H₂₂O. The fragment ion m/z 201.1638 is formed by the loss of a neutral molecule of H₂O from m/z 219.1742. During subsequent collision-induced cracking, fragmentation ions m/z 163.1117 and 159.1169 are produced. Therefore, it is speculated that it may be germacrone.⁴⁶ The specific secondary spectrum and possible cleavage pathway is shown in Figure 7.

Figure 7.

The secondary mass Spectrum and possible cleavage pathways of parthenolide.

GC-MS Analysis of Volatile Components from Cumin

Samples were injected according to the GC-MS conditions and a total ion chromatogram of the volatiles in cumin was obtained. The obtained data were searched against and matched with the mass spectrometry database by the National Institute of Standards and Technology (NIST 2017). The relative percentage was calculated by the peak area normalization method.⁴⁷ A total of 40 chemical components were identified in cumin volatile oil, accounting for 98.70% of the total peak area. These compounds included 16 monoterpenes, 5 sesquiterpenes, 8 alkanes, 3 alcohols, 4 aldehydes, 2 phenols, 1 ketone, and 1 alkylbenzene compound (Figure 8). Additionally, the volatile oil extract of cumin was found to have the highest percentage of cuminaldehyde (42.88%), γ-terpinene (12.29%), γ- terpinen-7-al (11.50%), o-cymene (7.9%), and β-pinene (11.41%), as shown in Figure 9 and Table 2.

Figure 8.

Comparison of the contents of various compounds in the volatile components of cumin.

Figure 9.

Total ion current chromatograms of volatile components cumin.

Table 2.

Identification of Chemical Constituents of Volatile oil Components in Cumin by GC-MS.

NO.	t_R/min	Compound	Molecular formula	Molecular weight	Relative amount (%)	CAS No.	Kovats’ RI	Classification
1	10.514	α-Phellandrene	C₁₀H₁₆	136	0.27	99-83-2	1005	Monoterpene
2	10.700	α-Pinene	C₁₀H₁₆	136	0.62	80-56-8	939	Monoterpene
3	11.941	β- Phellandrene	C₁₀H₁₆	136	0.71	555-10-2	1030	Monoterpene
4	12.010	β-Pinene	C₁₀H₁₆	136	11.41	127-91-3	979	Monoterpene
5	12.458	β-Myrcene	C₁₀H₁₆	136	0.52	123-35-3	992	Monoterpene
6	12.934	3-Carene	C₁₀H₁₆	136	0.04	13466-78-9	1007	Monoterpene
7	13.327	o-Cymene	C₁₀H₁₄	134	7.90	527-84-4	1020	Monoterpene
8	13.424	D-Limonene	C₁₀H₁₆	136	0.58	138-86-3	1032	Monoterpene
9	13.486	Eucalyptol	C₁₀H₁₈O	154	2.93	470-82-6	1032	Monoterpene
10	14.189	γ-Terpinene	C₁₀H₁₆	136	12.29	99-85-4	1060	Monoterpene
11	14.727	Undecane	C₁₁H₂₄	156	0.04	1120-21-4	1100	Alkane
12	15.099	Linalool	C₁₀H₁₈O	154	0.19	78-70-6	1098	Monoterpene
13	15.568	2-Cyclohexen-1-ol	C₁₀H₁₈O	154	0.05	822-67-3	883	Alcohols
14	15.934	Isopinocarveol	C₁₀H₁₆O	152	0.10	6712-79-4	1136	Monoterpene
15	16.465	Trans-2-Caren-4-ol	C₁₀H₁₆O	152	0.20	4017-82-7	1222	Alcohols
16	16.651	Terpinene-4-ol	C₁₀H₁₈O	154	0.20	562-74-3	1177	Monoterpene
17	16.796	D-verbenone	C₁₀H₁₄O	150	0.05	80-57-9	1195	Monoterpene
18	16.892	α- Terpinene	C₁₀H₁₈O	154	0.27	99-86-5	1017	Monoterpene
19	16.954	3-P-Menthen-7-al	C₁₀H₁₆O	152	3.79	27841-22-1	1196.5	Aldehydes
20	17.795	Cuminaldehyde	C₁₀H₁₂O	148	37.21	122-03-2	1246.5	Aldehydes
21	17.947	1,3-bis(1,1-dimethylethyl)-Benzene	C₁₄H₂₂	190	0.19	1014-60-4	－	Alkylbenzene
22	18.044	Tetradecane	C₁₄H₃₀	198	0.07	629-59-4	1400	Alkane
23	18.154	P-Meth-2-en-7-ol	C₁₀H₁₈O	154	0.06	19898-87-4	1268	Alcohols
24	18.312	Phellandral	C₁₀H₁₆O	152	0.38	21391-98-0	1267	Monoterpene
25	18.464	Cuminaldehyde	C₁₀H₁₄O	150	5.67	536-60-7	1291	Aldehydes
26	18.561	γ-Terpinene-7-al	C₁₀H₁₄O	150	11.50	22580-90-1	1297	Aldehydes
27	18.685	Thymol	C₁₀H₁₄O	150	0.12	89-83-8	1289	Phenols
28	19.871	γ-Muurolene	C₁₅H₂₄	204	0.19	30021-74-0	1451	Sesquiterpene
29	20.457	Caryophyllene	C₁₅H₂₄	204	0.08	87-44-5	1414	Sesquiterpene
30	20.795	β-Famesene	C₁₅H₂₄	204	0.14	18794-84-8	1459	Sesquiterpene
31	20.912	α-Caryophyllene	C₁₅H₂₄	204	0.05	6753-98-6	1452	Sesquiterpene
32	21.160	Acoradien	C₁₅H₂₄	204	0.10	24048-44-0	1483	Alkane
33	21.519	2,4-Di-tert-butulphenol	C₁₄H₂₂O	206	0.19	96-76-4	1509	Phenols
34	21.882	2,6,10,15-tetramethyl-Heptadecane	C₂₁H₄₄	296	0.07	54833-48-6	－	Alkane
35	22.698	Carotol	C₁₅H₂₆O	222	0.05	465-28-1	1612.3	Sesquiterpene
36	23.519	8-Heptadecene	C₁₇H₃₄	238	0.09	54290-12-9	1670.	Alkene
37	23.643	Heptadecane	C₁₇H₃₆	240	0.12	629-78-7	2231	Alkane
38	25.442	Muscone	C₁₆H₃₀O	238	0.05	541-91-3	1867	Ketones
39	26.008	2,6,10,14-tetramethyl-phytan-Hexadecane	C₂₀H₄₂	282	0.14	638-36-8	1811	Alkane
40	28.014	Heptacosane	C₂₇H₅₆	380	0.07	593-49-7	2700	Alkane

*Kovats’ RI taken from NIST.

Discussion

UPLC-Q-TOF-MS and GC-MS are highly efficient analytical techniques, known for their high sensitivity, precision, resolution, and rapid data acquisition capabilities, which have been effectively applied to analyze the complex chemical profiles of herbal plants. These methods enhance detection accuracy in the analysis of complex samples and are also used for the simultaneous determination of various components in TCM.³⁴

Cumin is not only widely used in TCM,⁴⁸ but also holds significant value in Mongolian and Uyghur medicinal practices, where it has been employed for the treatment of various diseases.⁴⁹ Current research on cumin's chemical composition has primarily focused on its volatile oils, with a particular emphasis on cuminaldehyde and other monoterpenes.¹⁰ However, there is a lack of detailed reports on the identification of highly polar substances such as aqueous and alcoholic extracts of cumin. Therefore, this study establishes UPLC-Q-Orbitrap MS and GC-MS analysis methods to comprehensively characterize the chemical constituents of cumin, integrating various databases and related literature.

In this study, a total of 102 compounds were identified in cumin, of which 62 were systematically identified from the aqueous extract using UPLC-Q-Orbitrap-MS. These include 10 flavonoids, 7 phenylpropanoids, 5 terpenoids, 4 alkaloids, 7 organic acids, 8 fatty acids, 8 amino acids, 2 glycosides and 10 other components. Among these, apigenin, a flavonoid component, is commonly found in the Umbelliferae family of plants and is known for its diverse biological and therapeutic properties, such as antioxidant, anti-inflammatory, anticancer, and antimicrobial effects.⁵⁰ According to relevant literature, apigenin also alleviates nephropathy, pancreatic β-cell dysfunction, genitourinary dysfunction, cardiomyopathy, and liver dysfunction in diabetes.^46,51 Therefore, apigenin may serve as a potential lead component for future studies on aqueous cumin extracts.

The GC-MS analysis of cumin's volatile oil revealed components accounting for 98.70% of the total peak area. These include monoterpenes, sesquiterpenes, alkanes, alcohols, aldehydes, phenols, ketones, and alkylbenzenes. As the primary active substance in cumin, the chemical composition and content of its volatile oil provide a scientific basis for its comprehensive utilization. Cuminaldehyde, the main component of cumin, exhibits anti-injury and anti-neuropathic effects on chronic compression nerve injury by stimulating opioid receptors, modulating the L-arginine /NO/ guanyyl cyclase /cGMP pathway, and inhibiting inflammatory cytokines.⁵² Additionally, cuminaldehyde demonstrates antibacterial and anticancer activities.^13,45 In summary, cuminaldehyde possesses broad pharmacological activities, high research value, and extensive application prospects.

The various types and sources of active ingredients in TCM can achieve comprehensive multi-component, multi-pathway, and multi-target therapy through synergistic or complementary effects. To conduct multi-mechanism and multi-target studies on TCM, it is essential to systematically investigate the chemical composition of these medicines. Only through a comprehensive understanding of the material basis of these medicines can further research be pursued. However, this study has some limitations; it primarily focused on the identification and analysis of chemical components and did not include basic research on blood components or pharmacodynamic substances.

Conclusion

The composition of TCM is complex and diverse, making it insufficient to evaluate quality control based solely on a single component. The quality control of TCM has evolved from “micro-analysis” of individual components to “macro-analysis” of the entire system. In this study, UPLC-Q-TOF MS and GC-MS analytical methods were established to systematically analyze the chemical composition of cumin, providing a foundation for exploring its biological activities, potential applications, compatibility, and pharmacological mechanisms in various fields, including pharmaceuticals, cosmetics, and functional foods.

Footnotes

Authors’ Contributions

Yanqiu Bai, Qier Mu, Junni Qi, Chula Sa contributed significantly to query papers and paper analysis. Yanqiu Bai organized the data and wrote the manuscript. Chula Sa helpd perfom the anlysis with constructive discussions All authors contributed to the study's conception and design.

Declaration of Conflicting Interests

The authors declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Ethical Approval

Ethical approval is not applicable for this article.

Funding

The authors disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This work was supported by Scientific and Technological Innovative Research Team for Inner Mongolia Medical University of Bioanalysis of Mongolian medicine's (No.YKD2022TD037), University Youth Science and Technology Talent Program (No.NJYT23135), The Inner Mongolia Medical University Mongolian Pharmacy “First-class Discipline” scientific research project (No. MYX2023-R17). The Inner Mongolia Medical University “First-class Discipline” construction innovation team project (No. 2024MYYLXK006).

ORCID iDs

Yanqiu Bai

Qier Mu

Junni Qi

Chula Sa

Statement of Human and Animal Rights

This article does not contain any studies with human or animal subjects.

Statement of Informed Consent

There are no human subjects in this article and informed consent is not applicable.

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