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Article

Differences in the Determination of Volatile Organic Compounds between Chrysanthemum morifolium Ramat. and Chrysanthemum indicum L. (Wild Chrysanthemum) by HS-GC-IMS

by
Gaigai Liu
1,2,
Hao Duan
1,2,
Yue Zheng
1,2,3,
Jinhong Guo
1,2,
Diandian Wang
1,2 and
Wenjie Yan
1,2,*
1
College of Biochemical Engineering, Beijing Union University, Beijing 100023, China
2
Beijing Key Laboratory of Bioactive Substances and Functional Food, Beijing Union University, Beijing 100023, China
3
College of Food Science and Engineering, Northwest A&F University, 22 Xinong Road, Yangling, Xianyang 712100, China
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(19), 4609; https://doi.org/10.3390/molecules29194609
Submission received: 10 August 2024 / Revised: 23 September 2024 / Accepted: 25 September 2024 / Published: 27 September 2024
(This article belongs to the Special Issue Extraction, Separation and Identification of Compounds from Natural Sources—Second Edition)
Browse Figures
Versions Notes

Abstract

:
Chrysanthemums and wild chrysanthemums are herbs with high application value. As edible plants of the Asteraceae family, they have good antioxidant, anti-inflammatory and hepatoprotective properties. Chrysanthemums and wild chrysanthemums contain a wide variety of volatile organic compounds, and these volatile components are the main factors contributing to the flavor differences. Therefore, in this study, we investigated the volatile components of holland chrysanthemum from Bozhou, Anhui Province, Chu-chrysanthemum from Chuzhou, Anhui Province, Gong-chrysanthemums from Huangshan, Anhui Province, Huai-chrysanthemums from Jiaozuo, Henan Province, Hang-chrysanthemum from Hangzhou, Zhejiang Province, and wild chrysanthemum from Dabie Mountain by headspace–gas chromatography–ion mobility spectrometry (HS-GC-IMS) coupled with principal component analysis (PCA). The results showed that Chrysanthemum and wild chrysanthemum contain alcohols, esters, hydrocarbons, ketones, aldehydes, acids, camphor, pyrazines and furans. Among them, alcohols, esters and hydrocarbons accounted for more than 15%. It was hypothesized that 2-methyl-1-propanol, 2-methylbutanol, 1-hexanol in alcohols and hexyl acetate, 3-methylbutyl acetate and ethyl 2-methylpropanoate in esters might be the main reasons for the alcoholic and sweet flavors of chrysanthemum and chrysanthemum officinale. Based on the principal component analysis, cluster analysis with the Euclidean distance and similarity analysis of fingerprints, it was found that there were significant differences in the volatile components in chrysanthemums from different origins, among which the differences between Chu-chrysanthemum and Hang-chrysanthemum were the most significant. In addition, as a genus of wild chrysanthemum with the same species, it contains a richer variety of volatile organic compounds, and the content of hydrocarbons and alcohols is significantly higher than that of chrysanthemum.

1. Introduction

Chrysanthemums (Chrysanthemum morifolium Ramat.) and wild chrysanthemums (Chrysanthemum indicum L.) are perennial herbaceous plants belonging to the family Asteraceae, of which chrysanthemums are considered to be one of the most economically valuable edible flowers in the world [1]. Chrysanthemum is distributed in China, Japan, Korea and Russia and other Asian countries, and even in the Netherlands and other European countries have some distribution [2]. Wild chrysanthemum is more widely distributed, from grassland, plains to hills. At present, China is the world’s largest producer of chrysanthemum [3]. In China, chrysanthemum plantations are mainly concentrated in Henan, Anhui, Hubei and Zhejiang. In the Chinese Pharmacopoeia of the People’s Republic of China (2020 edition), chrysanthemums are mainly mentioned as Bo-chrysanthemum from Bozhou, Anhui; Chu-chrysanthemum from Chuzhou, Anhui; Gong-chrysanthemum from Huangshan, Anhui; Huai-chrysanthemum from Jiaozuo, Henan; and Hang-chrysanthemum from Hangzhou, Zhejiang, as well as [4]. Modern research has confirmed that chrysanthemum and wild chrysanthemum have significant effects in lowering blood pressure, blood lipids and blood glucose, and also have the effect of clearing the liver and brightening the eyes [5]. They can not only be used in medicine, in which chrysanthemum also has a wide range of applications in health care functional food, known as the most representative flower-derived dietary herbs [6]. However, chrysanthemums and wild chrysanthemums from different origins have significant differences in composition and pharmacological activity [7].
The current analysis of chrysanthemum-related flavors mainly focuses on ornamental chrysanthemums, and little research has been conducted on edible chrysanthemums, especially for those mentioned in the Pharmacopoeia of the People’s Republic of China (2020 edition) [4], which were not analyzed and compared in more detail. A literature search revealed that chrysanthemums from their origins are more widely used and studied [8]. Therefore, chrysanthemums and wild chrysanthemums from six different origins were analyzed for more in-depth flavor substances.
Odor is one of the main factors in identifying the quality of herbs when used as marketed or functional foods, and the volatile flavor components they contain play an important role in the acceptability of chrysanthemums and wild chrysanthemums. Chrysanthemum is usually “sweet and bitter”, while wild chrysanthemum is “aromatic and bitter” [4]. Therefore, the comparison of the volatile components of chrysanthemums and wild chrysanthemums from different origins deserves in-depth study.
Currently, flavor components are generally analyzed by sensory and instrumental techniques [9]. One is to utilize sensory perception for subjective evaluation, and to evaluate the samples accordingly by providing certain training to the relevant personnel [10]. However, it has uncertainty and can be interfered by various disturbing factors, such as the environment, the rater’s mood, and physical condition [11]. The other is the use of instruments, such as electronic noses and gas chromatography, which are more objective than subjective evaluations and have a relatively high degree of accuracy. Among them, electronic noses are used for real-time monitoring of odor fingerprints and their changes in the samples by means of electronic sensors, but electronic noses identify the compounds as a whole and cannot analyze the single components [12,13]. Chromatographic techniques, on the other hand, can qualitatively and quantitatively analyze the samples by detecting the structure of the chemical components and combining them with their relative molecular masses, which can obtain the results in a short period of time, and solve the disadvantage of the electronic nose with slightly lower reproducibility [14,15,16].
In recent years, chromatographic techniques have been improved, mainly liquid chromatography–mass spectrometry (HPLC-MS), gas chromatography–mass spectrometry (GC-MS), gas chromatography–ion mobility spectrometry (GC-IMS) and headspace–gas chromatography–ion mobility spectrometry (HS-GC-IMS) [17,18]. For the analysis of volatile and semi-volatile substances, the headspace–gas chromatography–ion mobility spectrometry (HS-GC-IMS) technique is used. This technique is not only easy to operate, but also fast, sensitive and has a higher separation efficiency than GC-MS [19]. For example, the identification of volatile components of chamomile, chrysanthemum, and chrysanthemum tea was carried out using this technique, and a total of 47 chemical substances were identified [20]. Currently, analyses of the volatile constituents of chrysanthemums have focused on related tea broths and ornamental chrysanthemums [8,21], and there has been no identification and comparison of volatile constituents between chrysanthemums and wild chrysanthemums in the Pharmacopoeia of the People’s Republic of China (2020 edition).
This study utilized a combination of HS-GC-IMS and PCA, hierarchical cluster analysis heat map to efficiently and intuitively identify and classify the volatiles in chrysanthemums and wild chrysanthemums, and more volatile organic compounds were found. In the future, in the application process of related products, we can keep the ingredients with special aroma that do not have significant irritating odor, and we can also reduce the effect of the ingredients causing irritating odor on the products by certain technical means. We hope that the present study can provide a certain theoretical basis and application value for the future screening of raw materials of chrysanthemum and wild chrysanthemum and the enhancement of the nutritional value of functional food products.

2. Results

2.1. HS-GC-IMS Topography of Chrysanthemum and Wild Chrysanthemum Samples from Different Origins

In this study, HS-GC-IMS was used to analyze the differences in volatile organic compounds in chrysanthemums and wild chrysanthemums from different origins. The generated data were represented as 3D spectrograms with three axes representing relative migration time (X-axis), retention time (Y-axis) and signal peak intensity (Z-axis). As can be seen in Figure 1, the volatile compounds in chrysanthemums and wild chrysanthemums from different origins are very similar, but there are some differences, and it can be seen that the signal intensities shown in the red circles are slightly different.
In order to obtain a better view of these differences, these samples were compared in more detail using a top view. As shown in Figure 2, the blue color was chosen as the background color of the whole graph, and the red vertical line at the horizontal coordinate 1.0 was the RIP peak (reactive ion peak, normalized). The vertical coordinate represents the retention time (s) of the GC and the horizontal coordinate represents the relative migration time (normalized). Each point on either side of the RIP peak represents a VOC. The color represents the intensity of a substance’s peak, from blue to red, with darker colors indicating greater peak intensity. From the figure, it can be seen that there are some differences in the VOCs in different sample samples.
Although the topographic maps can show the differences in volatile compositions of chrysanthemum and wild chrysanthemum samples from different origins, it is not possible to visualize the differences in a more significant way. The spectrum of sample A was selected as the reference, and the spectra of other samples were deducted from the reference to obtain the difference comparison graph of different samples, as shown in Figure 3. If the VOC content is the same in the target sample and the reference, the background of the deduction is white, while the red color indicates that the concentration of the substance is higher in the target sample than in the reference, and the blue color indicates that the concentration of the substance is lower in the red color of the target sample than in the reference.
Comparing Figure 2 and Figure 3, it can be found that most of the signals have retention times of 50–1350 s and drift times of 1.0–2.3 ms. Moreover, in the differential contrast model plot (Figure 3), the concentration of different volatile components can be seen. Moreover, in the differential contrast model plot (Figure 3), the concentration of different volatile components can be seen. The retention times were 650–850 s and the drift times were 1.6–1.9 ms for all the samples except sample D. The darker the red color in the graph, the stronger the signal strength of the substance. The content of 4-isopropyltoluene in sample D was significantly higher than that in other samples at retention times of 1050–1150 s and drift times of 2.1–2.3 ms; the content of camphoraceous substances in sample A was significantly higher than that in other samples at retention times of 650–850 s and drift times of 1.7–1.9 ms; the content of (E, E)-2,4-octadienal was significantly higher than that in other samples at retention times of 750–850 s and drift times of 1.6–1.8 ms. The content of (E, E)-2,4-octadienal was significantly higher than that of other samples at the retention time of 750–850 s and drift time of 1.6–1.8 ms. The analysis showed that the concentration of volatile organic compounds (VOCs) contained in sample D was higher than that of samples A, B, C and E, indicating that Gong-chrysanthemum had a higher content of volatile components in these five chrysanthemum samples.

2.2. Comparative Analysis of the Fingerprints of Volatile Components in Chrysanthemum and Wild Chrysanthemum Samples from Different Origins

Fingerprinting allows a complete and clear comparison of the differences in specific volatile substances in chrysanthemums and wild chrysanthemums of different origins. As shown in Figure 4, each row of the graph represents all the signal peaks selected in a sample, and each column represents the signal peaks of the same VOC in different samples, and the color shades represent the signal strengths, and the darker the color indicates that the signal strength of the substance is stronger, and its content is higher.
The complete VOC information for each sample and the differences in VOCs between samples can be seen in Figure 4. Samples D and E had fewer species and concentrations, while sample F had the most volatiles. Wild chrysanthemum has the largest variety and content of volatiles, indicating a more distinctive flavor profile. The volatiles in the six different samples were further compared, and the fingerprints of all volatiles were analyzed, as shown in Figure 4. The results of the comparative analysis showed that the differences in the volatile substances of the six chrysanthemums were large.
2-Methyl-2-propanol, linalool, 2-butanone, 2-hexanone, formic acid geranyl ester, 1-phenylethyl acetate, and alpha-pinacol were the characteristic substances of sample A. heptanal, (2E,4E)-2,4-octadienal, 3-carene, ethyl 2-methylpropionate, Z-4-heptenal, and hexyl acetate are characteristic substances of sample B. 3-Hexanone, 1-penten-3-one, bornyl acetate, citronellal are characteristic substances of sample C. Hexanal, pentanol, 1-octen-3-ol, 2-isopropyl-3-methoxypyrazine are the characteristic substances of sample D.Acetoin,2,3-pentanedione,1-penten-3-ol,3-methyl-2-butenal,2-acetylfuran,2-heptanone, and heptanoic acid are the characteristic substances of sample E. Hexanol, benzaldehyde, citronellal, isoamyl acetate, methyl 3-methylbutyrate, ethyl 2-methylbutyrate ether are characteristic substances of sample F. Chrysanthemums and wild chrysanthemums of different origins have characteristic volatile organic compounds, mainly alcohols, aldehydes, esters and ketones. Among them, the volatiles of chrysanthemum and Gong-chrysanthemum were mainly alcohols, the volatiles of chrysanthemum were mainly aldehydes, the volatiles of Chu-chrysanthemum and Hang-chrysanthemum were mainly ketones, and the volatiles of wild chrysanthemum were mainly esters.

2.3. Cluster Analysis of Volatile Components of Chrysanthemum and Wild Chrysanthemum Samples from Different Origins

Principal Component Analysis (PCA) is a method of statistical analysis of multivariate variables. It assesses the regularity and variability among samples through certain recombined composite variables, and can express as much information as possible about the original variables by downscaling these new variables [22,23,24]. In the high-quality principal component analysis model. There are two principal components, PC1 and PC2, with an overall cumulative contribution of approximately 60% or even higher [24]. The principal component analysis of chrysanthemum and wild chrysanthemum samples in this study is shown in the PAC score plot.
As shown in Figure 5a, PC1 is 35.6% and PC2 is 23.5%, for a total cumulative contribution of 59.1%. As can be seen from Figure 5b, both samples A and D are located in the negative region of PC2 and the positive region of PC1, and both samples C and F are located in the positive region of PC2 and the negative region of PC1, which are in the same region but in different positions, and can be seen that there are more significant differences between them. The positions of B, D, E, and F are similar to the four quadrants of the coordinate axis, A is similar to the negative half-axis of the vertical axis, and the positions of B and C are in the negative half-axis and positive half-axis of the vertical axis, respectively, and there is a clear distinction between the positive and negative regions. The results showed that there were large differences in volatile constituent substances between chrysanthemums of different origins and significant differences between chrysanthemums and wild chrysanthemums. In a similar study, the flavor components of asparagus were clearly identified by analyzing the major volatile components in asparagus from different origins and different harvesting periods and the relationship between them, and significant differences between the volatile organic compounds of different asparagus were determined by combining and comparing the PCA analysis with the other two analyses [25].
Table 1 represents the Euclidean distance values between the five chrysanthemum samples and the wild chrysanthemum. From the results of the Euclidean distance analysis, it can be seen that the distances between chrysanthemum samples of different origins can be clearly distinguished. The average Euclidean distance between A and B is 14,200,000; between A and D is 10,388,888.889; between D and E is 16,566,666.667; and between E and C is 18,900,000. Therefore, E and C are the furthest away, i.e., the difference between Hang-chrysanthemum and Chu-chrysanthemum have the greatest difference. Sample E was located in the positive zone of PC2 and the positive zone of PC1, which was in a different zone from the rest of the samples, and it could be more clearly distinguished between chrysanthemums and wild chrysanthemums of different origins. However, principal component analysis failed to identify specific volatile organic compounds, and the relationship between the relevant components and treatments has not been clarified.
The combination of the HS-GC-IMS technique and PCA can visualize, quickly and accurately differentiate between differentiated substances and can determine the relationship between their main components and treatments [26]. In a similar study, sensory evaluation and principal component analysis of chrysanthemum teas from Anhui, Hunan and Hangzhou using e-tongue and PCA demonstrated that chrysanthemum teas from different origins had significant differences, especially in bitter and astringent flavors [27]. Another study examined volatile flavor compounds in the leaves of 15 taxa of Korean native chrysanthemum species and identified 45 volatile organic compounds using GC-MS [28].

2.4. Qualitative Analysis of Volatile Components Profiles of Chrysanthemum and Wild Chrysanthemum Samples from Different Origins

Currently, 41 volatile components of floral aroma have been identified in Chrysanthemum, mainly including terpenoids and hydrocarbons, of which terpenoids accounted for 11–54% and hydrocarbons accounted for 10–59% [8,29]. Wang et al. [30] utilized HS-LPME-GC to determine the volatile components in dried chrysanthemums and identified several representative components, including cineole, camphor, borneol and caryophyllene.
In the present study, volatile organic compounds from chrysanthemums and wild chrysanthemums of different origins were analyzed using HS-GC-IMS, and the qualitative characterization information expressed is shown in Figure 6, which has the differential time as the horizontal coordinate, the resolving time as the vertical coordinate, and the numbers in red represent the number of detected peaks. A total of 114 peaks were detected and 60 compounds were identified, including 14 alcohols, 12 esters, 11 hydrocarbons, 9 ketones, 7 aldehydes, 3 acids, 2 camphorates, 1 pyrazine and 1 furan. Of 2-methyl-1-propanol, 1-hexanol, 2-hexenal, 2-methybutyl acetate, 3-methylbutyl acetate, 3-methylbutanoic acid, camphor, alpha-pinene, camphene, beta-pinene, benzaldehyde, 1-octen-3-o l, cymene, hexylacetate, gamma-terpinene, (E)-2-pentenal, 3-hexanone, 2-methyl-1-pentanol, heptanal, gamma-butyrolactone, citronellal, bornyl acetate, 22 compounds were found to be available in monomeric and dimeric forms, respectively. Of these, since some compounds migrated at different times, it is presumed that their monomers underwent a polymerization reaction to form a polymer. Migration time is often a parameter used to determine the size and shape of molecules in biochemical analysis, especially in electrophoretic techniques. Dimers and multimers will have different migration times because their molecular weights and shapes affect their migration rates during electrophoresis. For example, four compounds, myrcene, beta-piene, citronellal, alpha-pinene, have a multimeric form. Compared with previous studies, the present study identified the most diverse VOCs in Chrysanthemum and wild chrysanthemum. The specific compound information is shown in Table 2.
There are significant differences in the physical properties of the different classes of compounds, which are especially evident in the odor. The flavor will vary somewhat depending on the class and content of the compounds contained. From Table 2, it can be found that both chrysanthemum and wild chrysanthemum have a cool, pungent and strong medicinal odor, which mainly comes from the camphor-like substances contained in them. Combined with Table 3, it can be found that the chrysanthemum has more p-cymene, so it will give off a citrus flavor and wood aroma; the content of 2,4-octadienal in chrysanthemum is much higher than that of other chrysanthemums, so it has a more significant melon and pear aroma; and in wild chrysanthemums, it contains a higher amount of alpha-pinene, citronellal and alpha-thujone, with the alpha-pinene odor described as terpene, peppermint, and pine, the citronellal odor as lemon, lemongrass, and rose, and the alpha-thujone odor as cypress and menthol. These substances may be the main reason why wild chrysanthemums have a minty odor.
In summary, it can be seen that alcohols accounted for 23.3% and esters for 20% of the volatile components identified. Through relevant database queries, the 2-methyl-1-propanol odor was described as fresh, boozy and leathery, and the 1-hexanol odor was described as fresh, fruity, alcoholic, sweet and green. Gamma-butyrolactone odor was described as creamy, fatty and caramel, camphene odor was described as fruity sweet, hexyl acetate odor was described as fruity, greenish, apple, banana and sweet, 3-methylbutyl acetate odor was described as sweet, banana fruity, ethyl 2-ethylpropanoate odor was described as sweet, fruity, alcoholic and rum. Methyl propanoate odor was described as sweet, fruity, alcoholic and rum [31]. It has been hypothesized that the alcoholic flavor and sweetness imparted by chrysanthemums and wild chrysanthemums may be related to the alcohol and ester components 2-methyl-1-propanol, 2-methylbutanol, 1-hexanol, gamma-butyrolactone, camphene, hexyl acetate, 3-methylbutyl acetate and ethyl 2-methylpropanoate which are alcohol and ester components related.

2.5. Hierarchical Cluster Analysis Heat Map

To further analyze the differences in VOCs in chrysanthemum samples from different origins, hierarchical cluster analysis (HCA) thermograms were generated. HCA can be used to distinguish between different sample clusters so that the degree of variation in the composition of the test samples can be clearly seen [32].
It is clear from Figure 7 that the relative content of volatiles varies between different chrysanthemum samples. Among the chrysanthemums of different origins, the volatile substance content in the sample of C (Chu-chrysanthemum) was higher and more diversified, and the volatile substance content in E (Hang-chrysanthemum) was lower than that in chrysanthemums of other origins. As can be seen from the graph, bornyl acetate monomer and Acetone are the most abundant in C. For F (wild chrysanthemum), it had significantly higher volatiles and higher species abundance than chrysanthemum, with higher levels of citronellal dimer, alpha-pinene polymer and alpha-phellandrene than chrysanthemum. The specific differences are shown in Figure 8, which can more clearly see that alpha-phellandrene in wild chrysanthemum is much higher than that in chrysanthemum. And combined with the analysis of its qualitative results, the compositional differences between chrysanthemums and wild chrysanthemums of different origins can be more clearly visualized. In this study, HS-GC-IMS was used to analyze the VOCs in chrysanthemum samples and wild chrysanthemum from different origins with fast response and high sensitivity.

3. Materials and Methods

3.1. Sample Preparation

All chrysanthemum and wild chrysanthemum samples were obtained from the source and were dried products. The representative appearance of these products is shown in Figure 9. Huai-chrysanthemum from Jiaozuo, Henan Province, Bo-chrysanthemum from Bozhou, Anhui Province, Chu-chrysanthemum from Chuzhou, Anhui Province, Gong-chrysanthemum from Huangshan, Anhui Province, Hang-chrysanthemum from Hangzhou, Zhejiang Province, and wild chrysanthemum from Dabie Mountain were pulverized by using a pulverizer, and subsequently sifted through an 80-mesh sieve, and their powders were obtained in order, and were named A, B, C, D, E, and F. The powder was then sifted through an 80-mesh sieve, and then sieved into the powder.

3.2. The HS-GC-MS System

Six samples were analyzed by FlavourSpec® gas-phase ion mobility spectrometry (the G.A.S. Department of Shandong Hai Neng Science Instrument Co., Ltd., Jinan, China). 2.0 g of each sample was accurately weighed and placed in 20 mL headspace flasks and incubated at 80 °C and 500 r/min for 15 min, then the samples were injected with a sample volume of 500 µL and a syringe temperature of 85 °C. The samples were then analyzed by FlavourSpec® gas-phase ion mobility spectrometry (the G.A.S. Department of Shandong Hai Neng Science Instrument Co., Ltd., Jinan, China). The samples were then analyzed.
The gas chromatographic column was a MXT-5 (the G.A.S. Department of Shandong Hai Neng Science Instrument Co., Ltd., Jinan, China) capillary column (15 m × 0.53 mm × 1 μm) at 60 °C, and the carrier gas was high-purity nitrogen (purity ≥ 99.999%); the program was boosted with the initial flow rate of 2.0 mL/min for 2 min, and then the flow rate was linearly increased to 10.0 mL/min within 8 min, and then linearly increased to 100.0 mL/min within 10 min. 100.0 mL/min within 10 min. Samples were injected through a CTC-PAL 3 static headspace autosampler (the G.A.S. Department of Shandong Hai Neng Science Instrument Co., Ltd., Jinan, China), and the temperature of the injection port was guaranteed to be 80 °C. The operation was stopped after 20 min.
Then, the ion mobility mass spectrometry (IMS) separation and detection were carried out. The ionization source was a tritium source (3H); the length of the migration tube was 53 mm; the electric field strength was 500 V/cm; the temperature of the migration tube was 45 °C; the drift gas was high-purity nitrogen (purity ≥ 99.999%); the flow rate was set at 150 mL/min; and the positive ion mode was used to carry out the measurements in three sets of parallel for each sample.

3.3. Data Analysis

The calibration curves of retention time and retention index were established by GC-IMS library search software (version 1.0.3) and Laboratory Analytical Viewer (LAV), and then the retention index of the target was calculated from the retention time of the target, and then searched and compared with the GC retention index (NIST 2020) database and IMS migration time database built in the VOCal software (NIST 2020).The target was then characterized by searching and comparing the GC retention index database (NIST 2020) and the IMS migration time database built in VOCal software (NIST 2020).
Reporter, Gallery Plot and Dynamic PCA plug-ins in VOCal data processing software (the G.A.S. Department of Shandong Hai Neng Science Instrument Co., Ltd., Jinan, China) were utilized to generate three-dimensional spectra, two-dimensional spectra, difference spectra, fingerprints and PCA plots of volatile constituents, respectively, for the comparison of volatile organic compounds among samples.

4. Conclusions

Current research has confirmed that chrysanthemums are rich in antioxidant and anti-inflammatory properties, and that their effects can be maximized through consumption and medicinal use. Therefore, this paper focuses on chrysanthemums and wild chrysanthemums mentioned in the Pharmacopoeia of the People’s Republic of China (2020 edition), and analyzes the flavor substances of chrysanthemums and wild chrysanthemums of different origins involved in them. In summary, the results of this study showed that 114 peaks of volatile organic compounds (VOCs) in chrysanthemums and wild chrysanthemums from different origins were detected by HS-GC-IMS, and a total of 60 compounds including 14 alcohols, 12 esters, 11 hydrocarbons, 9 ketones, 7 aldehydes, 3 acids, 2 camphorates, 1 pyrazine, and 1 furan, were identified in this study. The following are some examples of the types of hydrocarbons. Currently, there are 26 signal peaks that have not been identified. From the results of PCA, the Euclidean distance and hierarchical cluster analysis heatmap, the use of HS-GS-IMS can completely and effectively distinguish chrysanthemums of different origins, and at the same time, more abundant volatile organic compounds were found in wild chrysanthemums, and these unknown constituents can be further characterized and determined with the help of other analytical techniques in the future.
The results of PCA analysis, cluster analysis based on the Euclidean distance and similarity analysis of fingerprints showed that chrysanthemums from different origins had their own characteristic components. The characteristic substances in Huai-chrysanthemum are 2-methyl-2-propanol, linalool, 2-butanone, 2-hexanone, geranyl formate, styralyl acetate and alpha-pinitol. Heptanal, (2E,4E)-2,4-octadienal, 3-carene, ethyl 2-methylpropanoate, Z-4-heptenal, and hexyl acetate are characteristic substances of Bo-chrysanthemum. The characteristic substances in Chu chrysanthemum are 3-hexanone, 1-penten-3-one, icicle acetate and citronellal. The characteristic substances in Gong-chrysanthemum are hexanal, pentanol, 1-octen-3-ol and 2-isopropyl-3-methoxypyrazine. Characteristic substances in Hang-chrysanthemum are ethylidene, 2,3-pentanedione, 1-penten-3-ol, 3-methyl-2-butenal, 2-acetylfuran, 2-heptanone and heptanoic acid. The characteristic substances in wild chrysanthemum are hexanol, benzaldehyde, citronellal, isoamyl acetate, methyl 3-methylbutyrate, ethyl 2-methylbutyrate and ethylene glycol monobutyl ether. And according to its chart identification, it was found that both chrysanthemum and wild chrysanthemum contain camphor-like substances, which is presumed to be the main reason why chrysanthemum and wild chrysanthemum have a strong medicinal flavor. And their volatiles are mainly alcohols and esters: 2-methyl-1-propanol, 2-methylbutanol, 1-hexanol, gamma-butyrolactone, camphene, hexyl acetate, 3-methylbutyl acetate, and ethyl 2-methylpropanoate, which may also be the main reason for their boozy and sweet flavor.
In conclusion, by characterizing the volatile substances and using the fingerprints obtained, the differences in the volatile organic compounds of chrysanthemums and wild chrysanthemums were analyzed with a view to providing a theoretical basis for the development of chrysanthemums and wild chrysanthemums in the research and the development of chrysanthemums and wild chrysanthemums in the study and development of food flavors or functional food flavors.

Author Contributions

Conceptualization, G.L.; methodology, G.L.; software, H.D. and Y.Z.; validation, G.L. and Y.Z.; formal analysis, G.L.; investigation, H.D. and D.W.; resources, G.L.; data curation, G.L.; writing—original draft preparation, G.L.; writing—review and editing, W.Y.; visualization, J.G.; supervision, W.Y. and H.D.; project administration, W.Y. and H.D.; funding acquisition, W.Y. and H.D. All authors have read and agreed to the published version of the manuscript.

Funding

This study was supported by the National Key Research and Development Program of China [2023YFF1103802].

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

The data are contained within this article. Samples of the compounds are not available from the authors.

Acknowledgments

The authors would like to thank Wenjie Yan for his guidance and financial help.

Conflicts of Interest

The authors declare no conflicts of interest.

References

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Molecules 29 04609 g001
Figure 1. 3D geomorphological map.
Figure 1. 3D geomorphological map.
Molecules 29 04609 g001
Molecules 29 04609 g002
Figure 2. Topographic maps of all samples. (A: Huai-chrysanthemum; B: Bo-chrysanthemum; C: Chu-chrysanthemum; D: Gong-chrysanthemum; E: Hang-chrysanthemum; F: Wild chrysanthemum cm2).
Figure 2. Topographic maps of all samples. (A: Huai-chrysanthemum; B: Bo-chrysanthemum; C: Chu-chrysanthemum; D: Gong-chrysanthemum; E: Hang-chrysanthemum; F: Wild chrysanthemum cm2).
Molecules 29 04609 g002
Molecules 29 04609 g003
Figure 3. GC-IMS difference spectrum of volatile components.
Figure 3. GC-IMS difference spectrum of volatile components.
Molecules 29 04609 g003
Molecules 29 04609 g004
Figure 4. Fingerprints of volatile components. (A: Huai-chrysanthemum; B: Bo-chrysanthemum; C: Chu-chrysanthemum; D: Gong-chrysanthemum; E: Hang-chrysanthemum; F: Wild chrysanthemum cm2).
Figure 4. Fingerprints of volatile components. (A: Huai-chrysanthemum; B: Bo-chrysanthemum; C: Chu-chrysanthemum; D: Gong-chrysanthemum; E: Hang-chrysanthemum; F: Wild chrysanthemum cm2).
Molecules 29 04609 g004
Molecules 29 04609 g005
Figure 5. (a) Fingerprint similarity based on the Euclidean distance of different samples; (b) results of the PCA analysis of six samples.
Figure 5. (a) Fingerprint similarity based on the Euclidean distance of different samples; (b) results of the PCA analysis of six samples.
Molecules 29 04609 g005
Molecules 29 04609 g006
Figure 6. Qualitative characterization information for samples.
Figure 6. Qualitative characterization information for samples.
Molecules 29 04609 g006
Molecules 29 04609 g007
Figure 7. HCA of volatile components in six samples.
Figure 7. HCA of volatile components in six samples.
Molecules 29 04609 g007
Molecules 29 04609 g008
Figure 8. Representative component difference chart.
Figure 8. Representative component difference chart.
Molecules 29 04609 g008
Molecules 29 04609 g009
Figure 9. Chrysanthemum and wild chrysanthemum appearance.
Figure 9. Chrysanthemum and wild chrysanthemum appearance.
Molecules 29 04609 g009
Table 1. Euclidean distance values between different samples.
Table 1. Euclidean distance values between different samples.
A-1A-2A-3B-1B-2B-3C-1C-2C-3D-1D-2D-3E-1E-2E-3F-1F-2F-3
A-1043,157.97109,721.81.38 × 1071.40 × 1071.42 × 1071.30 × 1071.40 × 1071.51 × 1071.08 × 1071.01 × 1071.02 × 1071.88 × 1071.86 × 1071.83 × 1071.92 × 1071.89 × 1072.10 × 107
A-243,157.97029,902.041.40 × 1071.42 × 1071.44 × 1071.30 × 1071.39 × 1071.50 × 1071.08 × 1071.01 × 1071.02 × 1071.88 × 1071.86 × 1071.83 × 1071.90 × 1071.88 × 1072.09 × 107
A-3109,721.829,902.0401.42 × 1071.44 × 1071.46 × 1071.32 × 1071.41 × 1071.51 × 1071.08 × 1071.02 × 1071.03 × 1071.90 × 1071.88 × 1071.85 × 1071.92 × 1071.89 × 1072.10 × 107
B-11.38 × 1071.40 × 1071.42 × 107010,937.9129,639.991.63 × 1071.72 × 1071.83 × 1071.84 × 1071.80 × 1071.82 × 1072.39 × 1072.37 × 1072.34 × 1071.44 × 1071.45 × 1071.60 × 107
B-21.40 × 1071.42 × 1071.44 × 10710,937.91015,802.001.63 × 1071.73 × 1071.84 × 1071.86 × 1071.82 × 1071.83 × 1072.42 × 1072.41 × 1072.37 × 1071.45 × 1071.46 × 1071.61 × 107
B-31.42 × 1071.44 × 1071.46 × 10729,639.9915,802.0001.64 × 1071.73 × 1071.83 × 1071.87 × 1071.84 × 1071.85 × 1072.46 × 1072.44 × 1072.41 × 1071.44 × 1071.46 × 1071.60 × 107
C-11.30 × 1071.30 × 1071.32 × 1071.63 × 1071.63 × 1071.64 × 1070563,573.6850,431.21.72 × 1071.73 × 1071.75 × 1071.88 × 1071.86 × 1071.83 × 1071.68 × 1071.66 × 1071.81 × 107
C-21.40 × 1071.39 × 1071.41 × 1071.72 × 1071.73 × 1071.73 × 107563,573.60140,683.21.69 × 1071.79 × 1071.82 × 1071.95 × 1071.93 × 1071.93 × 1071.74 × 1071.66 × 1071.80 × 107
C-31.51 × 1071.50 × 1071.51 × 1071.83 × 1071.84 × 1071.83 × 107850,431.2140,683.201.80 × 1071.92 × 1071.95 × 1072.06 × 1072.04 × 1072.03 × 1071.75 × 1071.67 × 1071.80 × 107
D-11.08 × 1071.08 × 1071.08 × 1071.84 × 1071.86 × 1071.87 × 1071.72 × 1071.69 × 1071.80 × 1070487,389.5506,111.11.64 × 1071.65 × 1071.67 × 1072.50 × 1072.37 × 1072.66 × 107
D-21.01 × 1071.01 × 1071.02 × 1071.80 × 1071.82 × 1071.84 × 1071.73 × 1071.79 × 1071.92 × 107487,389.5023,838.091.65 × 1071.65 × 1071.64 × 1072.51 × 1072.43 × 1072.73 × 107
D-31.02 × 1071.02 × 1071.03 × 1071.82 × 1071.83 × 1071.85 × 1071.75 × 1071.82 × 1071.95 × 107506,111.123,838.0901.67 × 1071.67 × 1071.67 × 1072.52 × 1072.44 × 1072.73 × 107
E-11.88 × 1071.88 × 1071.90 × 1072.39 × 1072.42 × 1072.46 × 1071.88 × 1071.95 × 1072.06 × 1071.64 × 1071.65 × 1071.67 × 107033,015.81145,579.72.88 × 1072.80 × 1073.16 × 107
E-21.86 × 1071.86 × 1071.88 × 1072.37 × 1072.41 × 1072.44 × 1071.86 × 1071.93 × 1072.04 × 1071.65 × 1071.65 × 1071.67 × 10733,015.81055,887.572.85 × 1072.77 × 1073.13 × 107
E-31.83 × 1071.83 × 1071.85 × 1072.34 × 1072.37 × 1072.41 × 1071.83 × 1071.93 × 1072.03 × 1071.67 × 1071.64 × 1071.67 × 107145,579.755,887.5702.81 × 1072.75 × 1073.10 × 107
F-11.92 × 1071.90 × 1071.92 × 1071.44 × 1071.45 × 1071.44 × 1071.68 × 1071.74 × 1071.75 × 1072.50 × 1072.51 × 1072.52 × 1072.88 × 1072.85 × 1072.81 × 1070202,443.5401,301.5
F-21.89 × 1071.88 × 1071.89 × 1071.45 × 1071.46 × 1071.46 × 1071.66 × 1071.66 × 1071.67 × 1072.37 × 1072.43 × 1072.44 × 1072.80 × 1072.77 × 1072.75 × 107202,443.50268,847.8
F-32.10 × 1072.09 × 1072.10 × 1071.60 × 1071.61 × 1071.60 × 1071.81 × 1071.80 × 1071.80 × 1072.66 × 1072.73 × 1072.73 × 1073.16 × 1073.13 × 1073.10 × 107401,301.5268,847.80
Table 2. Results of the qualitative analysis of six samples (odor description queried at: https://www.femaflavor.org/ (accessed on 10 August 2024)).
Table 2. Results of the qualitative analysis of six samples (odor description queried at: https://www.femaflavor.org/ (accessed on 10 August 2024)).
CategoryNo.CompoundCAS#MW(RI)(Rt [min])(Dt [a. u.])Odor
Alcohols21-Butanol71-36-374.1655.92.797 1.36641wine
32-Methyl-1-propanol a78-83-174.1625.52.583 1.17021fresh, alcoholic, leather
42-Methyl-1-propanol b78-83-174.1623.82.571 1.36774ethereal, green, tropical fruity
51-Penten-3-ol616-25-186.1683.43.005 0.94351
92-Methylbutanol137-32-688.1732.53.580 1.48024roast onion, fruity, floral, wine
121-Hexanol a111-27-3102.2874.85.990 1.32128fresh, fruity, wine, sweet, green
131-Hexanol b111-27-3102.2868.75.859 1.64064mushroom, lavender, rose, hay
371-Octen-3-ol a3391-86-4128.2987.19.219 1.15932
381-Octen-3-ol b3391-86-4128.2987.89.246 1.59633camphor
482-Methyl-2-propanol75-65-074.1538.22.060 1.15207
60(Z)-2-Penten-1-ol1576-95-086.1772.14.142 0.94409green, plastic, rubber
611-Pentanol71-41-088.1762.94.003 1.25345balsamic
722-Methyl-1-pentanol a105-30-6102.2833.15.159 1.29837pungent
732-Methyl-1-pentanol b105-30-6102.2831.35.125 1.59325
94Linalool78-70-6154.31101.212.899 1.21493thujone, menthol
lemon, lemongrass, rose
102Alpha-Terpieol10482-56-1154.31169.515.678 1.28482
104Alpha-Terpineol98-55-5154.31200.417.128 1.21709pine terpenoid, citrus, floral
green, leaf, rose
113Geranyl formate105-86-2182.31340.425.552 1.21552
Aldehydes101-Hexanal66-25-1100.2796.24.519 1.56044fresh, green, fat, fruity
bitter almond, cherry, nutty
34Benzaldehyde a100-52-7106.1965.48.474 1.15018
35Benzaldehyde b100-52-7106.1965.18.463 1.46836potato, peas
56(E)-2-Pentenal a1576-87-084.1753.83.872 1.10677
643-Methyl-2-butenal107-86-884.1783.74.322 1.35879Fruity
sweet, woody, almond, bready
sweet, caramel, nutty, tobacco
712-Furaldehyde98-01-196.1833.15.159 1.0866
80(Z)-4-Heptenal6728-31-0112.2902.26.627 1.14558
83Heptanal a111-71-7114.2904.66.690 1.34951pungent, ether
aldehyde, fatty, green herbs,
84Heptanal b111-71-7114.2905.46.709 1.69633
Acids203-Methylbutanoic acid a503-74-2102.1839.45.276 1.22389sour, foot sweat, cheese
citrus, rose, woody, blueberry
floral, lilac, terpene
213-Methylbutanoic acid b503-74-2102.1839.45.276 1.49027
95Heptanoic acid111-14-8130.21104.313.015 1.36945
103Beta-citronellal106-23-0154.31176.816.011 1.35488
Hydrocarbon142-Hexenal a505-57-798.1852.25.524 1.1752sweet almonds, fruity, leaves, apples, plums, vegetables
Terpene, Mint, Pine
152-Hexenal b505-57-798.1854.45.568 1.51461
24Alpha-pinene a7785-70-8136.2932.87.464 1.2099
25Alpha-pinene b7785-70-8136.2935.77.548 1.29564
29Beta-pinene a127-91-3136.29778.866 1.2148resin, green
30Beta-pinene b127-91-3136.2978.78.924 1.63805
36Alpha-phellandrene99-83-2136.21013.510.039 1.67dill
39Delta-3-carene13466-78-9136.21009.79.931 1.72659citrus, lemon, woody
fresh, citrus, terpene,
40p-Cymene a99-87-6134.2104310.924 1.30429
41p-Cymene b99-87-6134.21042.510.906 1.72029woody, spice
oil, wood, terpenes, lemon,
46Gamma-terpinene a99-85-4136.21075.111.972 1.21183
47Gamma-terpinene b99-85-4136.21074.411.949 1.70654lime, herbs
green grassy, faint banana
52n-Pentanal110-62-386.1698.73.162 1.42093
57(E)-2-pentenal b1576-87-084.1751.93.844 1.35879potato, peas
fatty, sour, sweat
97(E,E)-2,4-Octadienal30361-28-5124.21120.413.628 1.77684
99Citronellal a2385-77-5154.31155.415.060 1.21008mung bean
100Citronellal b2385-77-5154.31157.615.155 1.85234lemon, lemongrass, rose
Ketones511-Penten-3-one1629-58-984.1674.92.939 1.30743strong pungent odors
1Acetone67-64-158.1513.91.935 1.11983fresh, apple, pear
62-Butanone78-93-372.1584.82.323 1.24445fruity, camphor
336-Methyl-5-hepten-2-one110-93-0126.2994.99.505 1.1714citrus, fruity, moldy, ketone
532-Butanone 3-hydroxy513-86-088.17103.296 1.3279butter, cream
cream, caramel, nuts, cheese
542,3-Pentandione600-14-6100.1706.73.256 1.22835
623-Hexanone a589-38-8100.27784.232 1.16011fruity, grape, sweet, rum
633-Hexanone b589-38-8100.27784.232 1.47481
662-Hexanone591-78-6100.2795.94.516 1.49481fruity, fungal, meaty, buttery
fruity, slight medicinal fragrance
782-Heptanone110-43-0114.28956.443 1.63381
93Alpha-thujone546-80-5152.21104.913.038 1.86cream, fat, caramel
Esters7Ethyl 2-methylpropanoate97-62-1116.2763.34.010 1.55185sweet, fruity, alcoholic, rummy
83-Methyl-butanoic acid methyl ester556-24-1116.2772.64.148 1.53037strong apple, pineapple
11Ethyl 2-methylbutanoate7452-79-1130.28475.422 1.64923Apple fruity
162-Methybutyl acetate a624-41-9130.2881.56.135 1.29836
172-Methybutyl acetate b624-41-9130.2881.56.135 1.73373sweet, banana, fruity
183-Methylbutyl acetate a123-92-2130.2886.56.245 1.30409
193-Methylbutyl acetate b123-92-2130.2888.76.295 1.75091
44Hexyl acetate a142-92-7144.2103210.584 1.38451fruity, green, apple, banana, sweet
45Hexyl acetate b142-92-7144.21031.210.561 1.91656
49Methyl acetate79-20-974.1544.12.091 1.19021Ethereal
cream, fat, caramel
85Gamma-butyrolactone a96-48-086.1920.27.108 1.08306
86Gamma-butyrolactone b96-48-086.1919.57.089 1.2989
gardenia
1051-Phenylethyl acetate93-92-5164.21203.317.270 1.05594
108Bornyl acetate a76-49-3196.31265.920.653 1.20966herbal, pine leaf
109Bornyl acetate b76-49-3196.31263.720.525 2.18845
112Isopulegyl acetate89-49-6196.31276.621.292 1.37376mint
Pyrazine982-Isopropyl-3-methoxy pyrazine25773-40-4152.21110.913.261 1.24178fatty, green, pear, melon
Polymers26Alpha-pinene c7785-70-8136.2932.57.457 1.66557Terpene, Mint, Pine
42Myrcene c-1123-35-3136.2996.99.575 1.71354must, spice, balsamic
lemon, lemongrass, rose
resin, green
43Myrcene c-2123-35-3136.2996.29.552 2.14292
101Citronellal c2385-77-5154.31153.214.965 2.19099
31Beta-pinene c-1127-91-3136.2977.48.880 2.17894
32Beta-pinene c-2127-91-3136.2978.18.902 2.55809
Furan792-Acetylfuran1192-62-7110.1894.56.431 1.11134pear, banana, fruity, slight medicinal fragrance
Camphor22Camphor a464-49-3152.21136.614.274 1.34427cool, pungent, strong medicinal taste
23Camphor b464-49-3152.21133.214.133 1.84416
27Camphene a79-92-5136.2951.28.018 1.20745woody, camphor
28Camphene b79-92-5136.2951.28.018 1.72926
Note: RI, retention index; Rt, retention time; Dt, drift time. a: monomer; b: dimer; c: polymer.
Table 3. Table of differences in the content of constituents between chrysanthemum and wild chrysanthemums.
Table 3. Table of differences in the content of constituents between chrysanthemum and wild chrysanthemums.
SampleABCDEF
Citronellal b2825.063 ± 311.7673029.415 ± 90.2089504.174 ± 150.2581130.174 ± 83.035594.981 ± 25.34919,935.519 ± 625.756
Citronellal a4240.191 ± 152.916212.55 ± 134.10510,979.493 ± 212.3474286.946 ± 620.8151913.36 ± 15.6643553.182 ± 23.644
Citronellal c59.693 ± 5.994107.97 ± 5.4661083.988 ± 22.26677.333 ± 9.38668.877 ± 5.5371807.551 ± 37.552
(E)-2-Pentenal b1544.384 ± 10.7221012.83 ± 12.5221023.602 ± 3.2931541.005 ± 30.9071500.362 ± 59.3131024.219 ± 50.792
(E)-2-Pentenal a396.835 ± 1.324335.796 ± 3.928100.316 ± 3.366535.949 ± 14.15203.75 ± 4.235177.514 ± 2.932
(E,E)-2,4-Octadienal1192.651 ± 26.98214,708.422 ± 63.505898.056 ± 63.246556.223 ± 12.682338.393 ± 114.0529917.439 ± 148.389
Alpha-pinene b1402.402 ± 3.4981371.06 ± 9.9381166.338 ± 26.8071633.6 ± 31.4231079.45 ± 6.869791.856 ± 16.939
Alpha-pinene a4071.159 ± 11.1783786.45 ± 29.145877.256 ± 40.2823940.424 ± 25.8013500.888 ± 62.5412875.96 ± 55.359
Alpha-pinene c11,442.659 ± 111.61310,791.332 ± 34.418366.991 ± 195.3569223.346 ± 60.5143766.755 ± 121.37116,081.79 ± 400.241
Linalool4402.249 ± 34.6662754.093 ± 21.0223484.353 ± 83.6912132.124 ± 79.75787.952 ± 18.9091691.72 ± 53.114
(Z)-2-Penten-1-ol316.707 ± 3.598287.878 ± 6.144191.349 ± 5.996517.487 ± 14.231367.465 ± 2.067108.935 ± 5.568
(Z)-4-Heptenal635.594 ± 33.2841245.405 ± 6.179273.128 ± 4.053610.033 ± 27.153546.022 ± 29.61277.641 ± 21.204
1-Butanol1715.981 ± 12.4014728.318 ± 35.543075.394 ± 45.5041393.119 ± 37.331574.953 ± 63.1724988.075 ± 194.39
1-Hexanal3724.348 ± 37.9973130.357 ± 62.5561158.475 ± 295.2153339.963 ± 341.334918.021 ± 111.3951249.278 ± 106.966
1-Hexanol b196.601 ± 8.151788.773 ± 16.713283.705 ± 4.958434.067 ± 7.79959.811 ± 1.8731584.674 ± 81.02
1-Hexanol a644.557 ± 5.216616.344 ± 10.039574.513 ± 6.981036.935 ± 23.295318.547 ± 7.136463.043 ± 14.268
1-Octen-3-ol b1053.852 ± 20.271000.329 ± 17.311851.294 ± 27.082118.039 ± 24.059202.776 ± 12.171785.737 ± 31.121
1-Octen-3-ol a1369.518 ± 9.3251615.156 ± 5.5631554.763 ± 4.2132254.018 ± 44.9021096.426 ± 89.6171737.718 ± 109.048
1-Pentanol538.727 ± 16.025541.481 ± 4.803454.079 ± 10.98647.792 ± 17.66358.871 ± 1.603461.167 ± 5.109
1-Penten-3-ol300.365 ± 7.087367.502 ± 8.734182.029 ± 11.154519.26 ± 15.326503.944 ± 6.752274.31 ± 8.462
1-Penten-3-one554.95 ± 4.081035.61 ± 8.5173173.32 ± 80.688623.15 ± 26.815584.78 ± 7.5821668.652 ± 128.461
1-Phenylethyl acetate3392.28 ± 23.2112290.869 ± 8.9871352.088 ± 35.3731584.211 ± 4.7071751.044 ± 37.7271370.581 ± 23.111
2,3-Pentandione159.694 ± 6.152334.943 ± 1.868254.51 ± 5.717279.47 ± 7.116647.531 ± 3.991182.076 ± 10.645
2-Butanone1698.224 ± 6.728970.721 ± 11.3181183.41 ± 17.581952.998 ± 47.8591598.619 ± 43.321081.831 ± 18.825
2-Butanone 3-hydroxy2055.259 ± 46.8213284.344 ± 20.4832123.28 ± 37.7773107.221 ± 25.0085591.911 ± 35.1041650.921 ± 9.038
2-Furaldehyde200.482 ± 2.28272.379 ± 2.57650.859 ± 1.60187.573 ± 5.129181.367 ± 3.03742.454 ± 4.959
2-Heptanone264.123 ± 8.224223.118 ± 4.825375.322 ± 5.07599.625 ± 1.981343.407 ± 37.936330.095 ± 18.373
2-Hexanone505.35 ± 14.317483.251 ± 3.935455.531 ± 36.455432.012 ± 7.946294.856 ± 12.802393.94 ± 3.457
2-Hexenal b5160.485 ± 51.2063688.567 ± 31.3393575.651 ± 39.0548273.701 ± 52.2962189.332 ± 35.9592782.315 ± 52.51
2-Hexenal a743.456 ± 25.5881753.04 ± 11.586403.135 ± 8.843542.754 ± 12.88522.099 ± 10.233806.048 ± 5.454
2-Isopropyl-3-methoxy pyrazine1497.287 ± 11.9552573.201 ± 42.7931696.038 ± 45.63210,858.284 ± 114.531420.291 ± 40.884840.125 ± 22.759
2-Methybutyl acetate b1334.981 ± 17.9041339.061 ± 7.665685.082 ± 28.844152.724 ± 10.61448.278 ± 2.8711005.383 ± 53.198
2-Methybutyl acetate a724.646 ± 6.442756.985 ± 3.711495.039 ± 9.392341.205 ± 9.359126.668 ± 1.881522.369 ± 12.799
2-Methyl-1-pentanol b68.645 ± 3.064163.215 ± 4.00684 ± 4.61873.949 ± 3.16717.563 ± 0.43214.544 ± 14.1
2-Methyl-1-pentanol a277.903 ± 3.554349.819 ± 7.307290.779 ± 5.553351.659 ± 16.56171.349 ± 3.495312.84 ± 8.539
2-Methyl-1-propanol b272.323 ± 3.729278.319 ± 5.837267.338 ± 1.555300.509 ± 6.00674.069 ± 1.923232.508 ± 13.88
2-Methyl-1-propanol a524.472 ± 16.296632.126 ± 5.693598.552 ± 5.415839.38 ± 26.266386.994 ± 13.268556.119 ± 30.345
2-Methyl-2-propanol1069.7 ± 7.409541.516 ± 0.593746.286 ± 1.98803.986 ± 18.411510.687 ± 11.152940.697 ± 24.328
2-Methylbutanol1325.873 ± 7.0931607.571 ± 11.0851076.535 ± 6.4151219.632 ± 15.172268.532 ± 7.9421693.174 ± 51.495
3-Hexanone b606.673 ± 17.751684.135 ± 13.4511238.309 ± 56.229210.639 ± 4.873134.987 ± 0.7711475.418 ± 75.564
3-Hexanone a412.421 ± 13.386912.889 ± 16.892617.404 ± 16.624267.355 ± 8.084311.278 ± 4.975262.989 ± 8.16
3-Methyl-2-butenal2614.625 ± 43.8272484.74 ± 99.6315757.293 ± 947.5382023.336 ± 508.3229940.402 ± 842.6866269.529 ± 435.626
3-Methylbutanoic acid b954.148 ± 99.641852.211 ± 19.2691882.101 ± 86.3771103.04 ± 25.177845.929 ± 10.8471784.733 ± 92.792
3-Methylbutanoic acid a787.781 ± 55.271383.964 ± 14.384505.373 ± 34.926947.641 ± 39.816907.718 ± 9.952776.635 ± 9.241
3-Methylbutyl acetate b170.946 ± 8.875164.962 ± 5.20269.952 ± 2.65527.028 ± 2.58524.298 ± 4.321582.069 ± 54.463
3-Methylbutyl acetate a233.319 ± 21.051229.359 ± 4.58114.067 ± 6.64161.848 ± 10.73562.241 ± 2.71395.959 ± 5.334
2-Acetylfuran137.379 ± 7.036443.635 ± 17.858697.362 ± 22.76313.253 ± 3.4881058.682 ± 37.403369.625 ± 8.148
Acetone9937.83 ± 23.00611,941.912 ± 23.63112,158.292 ± 80.71910,257.431 ± 251.3110,405.129 ± 65.24511,318.299 ± 89.473
Alpha-phellandrene253.622 ± 14.6941073.087 ± 11.035511.084 ± 18.506679.988 ± 27.402441.449 ± 10.1396735.333 ± 192.996
Alpha-terpieol2359.078 ± 59.811357.65 ± 19.441952.215 ± 1.466690.553 ± 11.704645.298 ± 12.3693967.721 ± 52.078
Alpha-terpineol7167.358 ± 41.731343.755 ± 8.9742397.673 ± 98.381597.043 ± 83.792175.126 ± 20.1761067.31 ± 46.124
Alpha-thujone654.039 ± 16.3741123.151 ± 34.743547.913 ± 22.677554.919 ± 42.3041817.227 ± 84.15117,396.78 ± 165.955
Benzaldehyde b920.376 ± 14.175952.486 ± 0.8851088.496 ± 18.2521023.338 ± 33.251374.142 ± 8.272179.382 ± 46.044
Benzaldehyde a976.783 ± 10.8711113.11 ± 6.734952.394 ± 18.1521333.735 ± 21.054939.441 ± 26.309985.417 ± 19.907
Beta-citronellal332.559 ± 32.39425.507 ± 16.0611488.985 ± 51.464195.047 ± 20.866147.069 ± 6.58874.15 ± 21.093
Beta-pinene b2528.678 ± 18.2062559.66 ± 7.982994.272 ± 17.6223252.752 ± 35.3672154.97 ± 42.1012051.414 ± 80.244
Beta-pinene a2826.033 ± 48.4973255.064 ± 25.0523359.369 ± 48.13709.292 ± 37.4424172.802 ± 53.5982207.279 ± 34.857
Beta-pinene c-16196.205 ± 39.5414718.965 ± 67.3454100.127 ± 169.1143302.962 ± 54.286771.942 ± 28.4917101.551 ± 122.436
Beta-pinene c-2943.207 ± 17.128360.358 ± 20.508308.354 ± 21.18212.635 ± 9.503116.688 ± 10.2251263.187 ± 66.259
Bornyl acetate b1565.311 ± 14.112501.45 ± 31.8255115.825 ± 375.8091812.541 ± 42.723260.377 ± 19.1611840.328 ± 88.389
Bornyl acetate a11,124.535 ± 16.5586353.636 ± 59.41515,289.999 ± 9.13811,729.532 ± 167.0381527.121 ± 92.6029451.247 ± 72.889
Camphene b593.797 ± 1.099506.467 ± 13.3841078.246 ± 7.095192.453 ± 15.30288.527 ± 4.018965.494 ± 129.185
Camphene a10,965.884 ± 33.30210,833.183 ± 10.4999553.585 ± 209.2358785.027 ± 47.3594858.39 ± 107.67110,498.42 ± 126.534
Camphor b20,266.817 ± 138.83623,749.914 ± 93.34123,022.477 ± 95.7729162.253 ± 224.6373669.357 ± 57.58721,994.788 ± 458.43
Camphor a6133.533 ± 103.5995189.051 ± 30.2454393.395 ± 51.5736498.457 ± 59.2194455.203 ± 75.983915.589 ± 17.663
Delta-3-carene132.514 ± 9.2742366.018 ± 10.661669.33 ± 21.83118.453 ± 4.696261.679 ± 11.3631462.493 ± 58.672
Ethyl 2-methylbutanoate138.249 ± 8.577489.096 ± 11.198182.273 ± 2.251260.743 ± 9.78468.223 ± 3.4022621.915 ± 169.078
Ethyl 2-methylpropanoate318.692 ± 7.984917.68 ± 3.255220.792 ± 7.268265.075 ± 7.6278.928 ± 0.942426.274 ± 28.982
Gamma-butyrolactone b930.888 ± 69.772359.555 ± 7.488354.153 ± 24.311422.583 ± 28.419186.657 ± 5.559453.242 ± 8.58
Gamma-butyrolactone a909.139 ± 25.648372.019 ± 6.16424.385 ± 6.689900.071 ± 25.937572.773 ± 1.669351.585 ± 6.624
Gamma-terpinene b556.677 ± 4.606210.187 ± 5.344651.832 ± 14.062131.27 ± 2.89538.058 ± 1.628721.183 ± 39.372
Gamma-terpinene a5081.537 ± 40.313943.89 ± 51.4825366.795 ± 63.7663392.369 ± 56.998858.552 ± 7.4295846.44 ± 86.406
Geranyl formate8583.753 ± 62.08241.205 ± 14.802381.155 ± 78.127450.238 ± 75.432231.62 ± 48.438436.755 ± 86.56
Heptanoic acid162.129 ± 12.607286.251 ± 3.1791.055 ± 2.416109.447 ± 5.27872.165 ± 3.46162.626 ± 3.213
Hexyl acetate b358.53 ± 18.941418.931 ± 4.567315.414 ± 8.372375.405 ± 10.132306.776 ± 2.619192.307 ± 11.945
Hexyl acetate a146.962 ± 8.044142.352 ± 4.388390.6 ± 7.076151.54 ± 9.0511756.449 ± 22.052157.767 ± 5.354
Isopulegyl acetate117.503 ± 4.234593.248 ± 21.458423.447 ± 14.71779.057 ± 3.19937.441 ± 4.691154.621 ± 15.865
Methyl acetate338.277 ± 12.2541013.593 ± 3.847967.783 ± 7.581368.183 ± 10.435277.988 ± 1.689421.014 ± 12.501
Methyl-5-hepten-2-one375.606 ± 12.3491347.956 ± 53.871585.792 ± 56.2281140.322 ± 45.541602.273 ± 64.2049405.44 ± 157.669
Myrcene c-11210.857 ± 10.697925.157 ± 5.002819.306 ± 5.759976.111 ± 24.42867.97 ± 7.341887.19 ± 37.47
Myrcene c-28948.613 ± 36.2418451.142 ± 20.4868279.251 ± 2.7611,074.886 ± 48.8937918.744 ± 80.6096485.896 ± 50.106
n-Pentanal1266.865 ± 16.8351709.672 ± 8.8381456.214 ± 38.665633.634 ± 13.947705.014 ± 34.152779.038 ± 32.353
p-Cymene b261.845 ± 11.725506.495 ± 10.205311.848 ± 16.235176.002 ± 3.382202.759 ± 3.6541236.11 ± 67.634
p-Cymene a2142.683 ± 6.5972304.334 ± 9.3631738.314 ± 16.0981788.107 ± 49.6582005.642 ± 24.1611753.989 ± 24.705
Heptanal b12,368.913 ± 142.879742.773 ± 27.73310,713.188 ± 44.569971.672 ± 52.5232469.909 ± 48.3110,366.861 ± 179.679
Heptanal a9664.966 ± 241.8517205.739 ± 74.516620.843 ± 140.6077293.801 ± 84.5355992.317 ± 40.6226642.647 ± 139.93
3-Methyl-butanoic acid methyl ester721.335 ± 8.925549.814 ± 3.547426.946 ± 21.264227.048 ± 12.816130.986 ± 3.9692287.457 ± 119.615
Note: a: monomer; b: dimer; c: polymer.
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MDPI and ACS Style

Liu, G.; Duan, H.; Zheng, Y.; Guo, J.; Wang, D.; Yan, W. Differences in the Determination of Volatile Organic Compounds between Chrysanthemum morifolium Ramat. and Chrysanthemum indicum L. (Wild Chrysanthemum) by HS-GC-IMS. Molecules 2024, 29, 4609. https://doi.org/10.3390/molecules29194609

AMA Style

Liu G, Duan H, Zheng Y, Guo J, Wang D, Yan W. Differences in the Determination of Volatile Organic Compounds between Chrysanthemum morifolium Ramat. and Chrysanthemum indicum L. (Wild Chrysanthemum) by HS-GC-IMS. Molecules. 2024; 29(19):4609. https://doi.org/10.3390/molecules29194609

Chicago/Turabian Style

Liu, Gaigai, Hao Duan, Yue Zheng, Jinhong Guo, Diandian Wang, and Wenjie Yan. 2024. "Differences in the Determination of Volatile Organic Compounds between Chrysanthemum morifolium Ramat. and Chrysanthemum indicum L. (Wild Chrysanthemum) by HS-GC-IMS" Molecules 29, no. 19: 4609. https://doi.org/10.3390/molecules29194609

APA Style

Liu, G., Duan, H., Zheng, Y., Guo, J., Wang, D., & Yan, W. (2024). Differences in the Determination of Volatile Organic Compounds between Chrysanthemum morifolium Ramat. and Chrysanthemum indicum L. (Wild Chrysanthemum) by HS-GC-IMS. Molecules, 29(19), 4609. https://doi.org/10.3390/molecules29194609

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