Next Article in Journal
Ameliorative Effect of Imperatorin on Dermatophagoides pteronyssinus-Induced Allergic Asthma by Suppressing the Th2 Response in Mice
Next Article in Special Issue
Synthesis and Characterization of a Multi-Walled Carbon Nanotube–Ionic Liquid/Polyaniline Adsorbent for a Solvent-Free In-Needle Microextraction Method
Previous Article in Journal
Potential of Essential Oil-Based Anticholinesterase Insecticides against Anopheles Vectors: A Review
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 27
Issue 20
10.3390/molecules27207021
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

The Difference of Volatile Compounds in Female and Male Buds of Trichosanthes anguina L. Based on HS-SPME-GC-MS and Multivariate Statistical Analysis

by
Pingping Song
,
Bo Xu
,
Zhenying Liu
,
Yunxia Cheng
and
Zhimao Chao
*
Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(20), 7021; https://doi.org/10.3390/molecules27207021
Submission received: 15 September 2022 / Revised: 7 October 2022 / Accepted: 14 October 2022 / Published: 18 October 2022
(This article belongs to the Special Issue Applications of Solid-Phase Microextraction and Related Techniques)
Browse Figures
Versions Notes

Abstract

:
Trichosanthes anguina L. (family Cucurbitaceae) is a monoecious and diclinous plant that can be consumed as a vegetable and has anti-inflammatory and antioxidant effects. The chemical composition and content of volatile compounds in female and male buds of T. anguina were explored by headspace solid-phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) technology combined with multivariate statistical analysis. The results showed that the content of the volatile compounds was different between female and male buds. 2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol and 2,2,6-trimethyl-6-vinyldihydro-2H-pyran-3(4H)-one were the main volatile compounds in both female and male buds. Based on the multivariate statistical analysis of orthogonal projections to latent structures discriminant analysis (OPLS-DA) and t-test, the content of seven compounds was significantly different between female and male buds. The content of three compounds in male buds was higher than that in female, i.e., (E)-4,8-dimethyl-1,3,7-nonatriene, 1,5,9,9-tetramethyl-1,4,7-cycloundecatriene, and (E)-caryophyllene. Conversely, the content of (Z)-4-hexen-1-ol, (Z)-3-hexenyl benzoate, (Z)-3-hexenyl salicylate, and 2-hexen-1-ol in female buds was higher than that in male buds. This is the first report on the difference in the volatile compounds between female and male buds of T. anguina, which enriches the basic research on the monoecious and diclinous plant and provides a reference for the study of plant sex differentiation.

1. Introduction

Trichosanthes anguina L. (family Cucurbitaceae), an annual climbing herb, is known as snake gourd or snake bean for its slender (up to 200 cm in length and 3 cm in diameter), twisted, and snake-like shape fruit. It is originated in India and Malaysia and commonly cultivated in tropical and subtropical areas and northern China [1]. Its tender fruit is a popular vegetable, which contains proteins, carbohydrates, cellulose, fat, and a variety of minerals [2]. The fruit, seed, and root of T. anguina can be used in traditional Chinese medicine for some effects in clearing heat and generating fluid, moisturizing the lung, eliminating dampness, and destroying parasites [3]. It has anti-inflammatory and antioxidant activities and can be used for the treatment of malaria and bronchitis [4]. In addition, two proteins of TR3 from the root and of TS3 from the seed have cytotoxic activity on cancer cell lines [5].
The seed of T. anguina contains 3% free sugar, 7% starch, 20% protein, and 43% fat oil, which consists of punicic acid, palmitic acid, stearic acid, oleic acid, and linoleic acid [6,7]. The fruit contains chlorogenic acid, isochlorogenic acid, p-coumaric acid, vanillic acid, ferulic acid, protocatechuic acid, caffeic acid, salicylic acid, phloretic acid, 3-indole acetic acid, phloroglucinol, quercetin, calcium, iron, phosphorus, folic acid, carotene, and vitamins B1, B2, and C [8,9]. The leaf contains kaempferol-3-O-β-galactoside and kaempferol-3-O-β-sophoroside [10].
Most flowering plants are bisexual plants whose flowers have both pistils and stamens. In order to avoid the decrease in the survival adaptability of offspring caused by self-inbreeding or self-mating [11], some plants evolved to unisexual; that is, there are only pistils or stamens in each flower, called female flower or male flower. The plant of which female and male flowers grow in different plants is called a dioecious plant, but in the same plant is known as a monoecious and diclinous plant. There are many differences in apparent structure, physiological function, and chemical components between female and male flowers of dioecious plants, such as Populus tomentosa (family Salicaceae) [12], Herpetospermum pedunculosum (family Cucurbitaceas), and T. kirilowii [13,14]. For monoecious and diclinous plants, the difference between female and male flowers also exists; for example, the chemical compounds from flowers of Cucurbita moschata (family Cucurbitaceas) [15] and the flower morphology of Croton sarcopetalus (family Euphorbiaceae) [16]. However, there are few comparative reports on the difference between female and male flowers of some monoecious and diclinous plants up to now.
The plant of T. anguina is one of the monoecious and diclinous plants. Its calyxes are green, five-lobed, and villous. Both female and male flowers bloom at night, but the blooming time of females is later than that of male flowers. Their corollas are pale yellowish green at the initial opening and turn white at full opening, five-lobed, and with branched and curly terminals. Female flowers are solitary and male flowers are raceme. Female flowers are 5–6 cm long and located at the top of juvenile fruit with a green pistil, two-lobed stigma, and inferior ovary. Male flowers are 3–5 cm long with three stamens and connate anthers. The female and male flowers and tender fruit are shown in Figure 1. The chemical constituents of female and male buds of T. anguina were studied, and the difference in sex was compared to make up for the deficiency of sex study of the monoecious and diclinous plants.
Solid-phase microextraction (SPME) is a sample treatment method invented by Pawliszyn and Arthur in the 1990s [17], which needs no solvent to extract the sample components. The SPME fiber is used to extract samples directly whose weight is usually less than 5 mg [18]. Headspace (HS) technology combined with SPME is a convenient extraction method. The sample is directly placed in a sealed headspace bottle, and an SPME fiber is put into the headspace bottle and located above the sample. During the heating and extraction process, volatile substances diffuse from the sample to the SPME fiber and are enriched in the fiber. This extraction method is so quick, less than one hour, and does not destroy the sample or require a liquid solvent. HS-SPME is often combined with gas chromatography-mass spectrometry (GC-MS) for widespread use in some volatile substances analysis [19,20].
The material of SPME fiber coating is crucial to the extraction, which determines the fiber’s affinity to compounds in the sample. Since the introduction of SPME, many coating materials have been employed in the analysis. Polydimethylsiloxane (PDMS) fiber could be used to determine the content of acrylamide from coffee beans [21]. Polyacrylate (PA) fiber was suitable for the quantification of sesquiterpenes in Zingiber zerumbet L. (family Zingiberaceae) volatiles [22]. Polydimethylsiloxane/divinylbenzene (PDMS/DVB) could be applied for the determination of the esters of carboxylic acids in insect lipids [23]. Carboxen/polydimethylsiloxane (CAR/PDMS) fiber was used for the analysis of volatile compounds from European ciders [24]. Divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) fiber was able to extract more chemical diverse volatile compounds, including ketones, aldehydes, alcohols, terpenoids, and others from Medicago sativa L. (family Leguminosae) compared with PDMS and CAR/PDMS fibers [25] and to analyze a variety of plants and their oils such as sweet potato, tomato, and olive oils [26,27,28]. In this study, DVB/CAR/PDMS fiber was selected due to its better ability to provide a more comprehensive chemical profile of plants and its great extraction effect in the pre-experiment.
The buds, just before blooming, were picked up as experimental samples for the detection of volatile compounds in order to avoid any contamination of external substances. The HS-SPME-GC-MS method was used to detect and identify the volatile compounds from the female and male buds of T. anguina. The multivariate statistical analysis of OPLS-DA and t-test were carried out to screen out the differential compounds between female and male buds for revealing the difference in the chemical composition of genders of monoecious and diclinous plants.

2. Results

2.1. Volatile Compounds of GC-MS Analysis

Both female and male fresh buds of T. anguina just before blooming were individually picked up at night. The samples were weighed as f1 0.1063 g, f2 0.1057 g, f3 0.0975 g, m1 0.0842 g, m2 0.0826 g, and m3 0.0849 g. The volatile compounds were analyzed by HS-SPME-GC-MS successfully. The total ion chromatography is shown in Figure 2. A total of 53 compounds were identified on the base of mass spectrum and retention index (RI). The relative content of these volatile compounds was calculated with peak area normalization and shown in Table 1. The total ion chromatograms of volatile compounds for three female and three male bud samples are shown in Figure 3.
2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (no. 26) (female 38.71–42.71% and male 39.62–42.64%) and 2,2,6-trimethyl-6-vinyldihydro-2H-pyran-3(4H)-one (no. 12) (female 27.44–35.82% and male 28.34–32.95%) were two compounds with the highest content of T. anguina buds.
The volatile components of female and male buds of T. anguina included alcohols, ketones, aromatic esters, non-aromatic esters, monoterpenes, sesquiterpenes, diterpenes, alkenes, oximes, heterocycles, alkanes, and acids. The detailed results are shown in Table 2. Among them, the type of heterocycles was the highest content component, with a total relative content of 69.75–75.49% for female and of 69.58–73.39% for male buds. The total content of alcohols was the second highest, with 9.48–12.36% for females and 7.59–8.89% for male buds. Interestingly, there were seven sesquiterpenes whose content in male buds (average 3.56%) was significantly higher than that in female buds (average 2.66%) with p < 0.05 in the t-test. In addition, the content of four alkenes in male buds (average 5.34%) was significantly higher than that in female buds (average 2.25%), with p < 0.05 in the t-test. These results showed that there was a significant difference between female and male buds in terms of the content of sesquiterpenes and alkenes.

2.2. Multivariate Statistical Analysis

An OPLS-DA model of multivariate statistical analysis was carried out in order to further explore the difference in volatile compounds between female and male buds. This model was verified by 200 times permutation tests. Figure 4a showed that the R2 and Q2 values generated by any random arrangement on the left end were smaller than those on the right end, the slope of the regression line was large, and the lower regression line intersected the negative half-axis of the Y-axis, indicating that the model was not overfitting and could be used to find differential compounds. The OPLS-DA score diagram (Figure 4b) showed that the points of f1−f3 of female samples and m1−m3 of male samples were separated along the t1 axis. The value of R2 was 0.944, and that of Q2 was 0.838, both of which were greater than 0.5, indicating that the model had suitable interpretation and prediction ability.
Seven compounds were screened out as differential compounds between female and male buds of T. anguina, whose VIP values were greater than 1 (Table 3), dots were far away from the origin in the S-plot (Figure 4c), and p values of t-test were less than 0.05. The content of three compounds in females was significantly lower than that in male buds, i.e., (E)-4,8-dimethyl-1,3,7-nonatriene (no. 4), 1,5,9,9-tetramethyl-1,4,7-cycloundecatriene (no. 21), and (E)-caryophyllene (no. 19). The content of (Z)-4-hexen-1-ol (no. 9), (Z)-3-hexenyl benzoate (no. 39), (Z)-3-hexenyl salicylate (no. 46), and 2-hexen-1-ol (no. 10) in female was higher than that in male buds. These seven differential compounds were marked in red in the S-plot (Figure 4c).

2.3. Heat Map

The content distribution of seven differential compounds in the female and male buds of T. anguina was visualized in the form of a heat map. Horizontal columns represented different samples (f1–3 and m1–3), and vertical columns represented different compounds (no. 4, 19, 21, 39, 46, 9, and 10). If the color of the block was red, the deeper the red was, the higher the content of the compound in the sample was; if the color was blue, the deeper the blue was, the lower the content of the compound was. As shown in Figure 5, six samples were clearly separated into two groups, i.e., all three female samples were classified into a group on the left, and three male samples were classified into a group on the right. Therefore, the different content levels of seven differential compounds in the female and male buds could be intuitively and clearly observed in Figure 5.

3. Discussion

As a monoecious and diclinous plant, the structure and function of female and male buds and flowers of T. anguina are quite different. The buds just before opening were collected for our experiment, which confirmed some differences in the volatile compounds between female and male buds. The results must be more accurate and reliable than those of opening flowers, which can avoid the loss of bud volatile compounds and the pollution of external substances [13]. This is the first report to study the volatile compounds from the buds and to find the differential compounds between female and male buds of T. anguina.
Diisobutyl phthalate (no. 51) is usually used as a plasticizer, which is often detected in soil, water, and air, besides in plastics. It is a detection index component of environmental pollution [54]. In this experiment, the fresh buds were treated by HS-SPME without any solvent extraction or plastics exposure. Therefore, it was suspected to be derived from the soil during growth or from the air.
(E)-4,8-Dimethyl-1,3,7-nonatriene (DMNT) is one of the floral compounds of some night-flowering plants [55]. DMNT can attract insects to pollinate [56] and has the function of attracting natural enemies of pests to avoid pest invasion [57]. The average content of DMNT in males (3.48%) was 6.14 times that in female buds (0.57%), whose content gap between genders was the largest. The results pointed out that high DMNT content in male buds was more conducive to attracting insects to pollinate and improving the reproductive capacity of T. anguina.
(E)-Caryophyllene, a bicyclic sesquiterpene, has many pharmacological effects such as anti-inflammation, antidepression, and anti-convulsion [58]. Its average content in male (2.37%) was higher than that in female buds (1.81%), which is a significant difference with p < 0.05 in the t-test between female and male buds. The result indicated that the male buds should have stronger pharmacological activities than the female buds of T. anguina.
1,5,9,9-Tetramethyl-1,4,7-cycloundecatriene was detected, whose average content in male (1.42%) was higher than that in female (1.08%) buds and had a significant difference (p < 0.05 in t-test) in genders. It was often found in volatile components from some plants, such as Zanthoxylum dissitum (family Rutaceae) and Artemisia dracunculus (family Compositae) [39,59].
(Z)-3-Hexenyl benzoate and (Z)-3-hexenyl salicylate are two (Z)-3-hexenol esters of aromatic acids. The average content of the former was 1.26% in females and 0.64% in males, and of the latter was 0.92% in female and 0.47% in male buds. Both of their content in females was about two times that in male buds. (Z)-3-Hexenyl benzoate showed specific binding to odorant-binding proteins of Halyomorpha halys and Plautia stali, which was similar to alarm pheromones of both two pests with the function of repelling [60]. The higher content of (Z)-3-hexenylbenzoate in female buds indicated that the compound might help female flowers avoid pests and protect female flowers’ pollination and development. (Z)-3-Hexenyl salicylate is a useful compound for people, often used as fragrance ingredients for fine fragrances, shampoos, toilet soaps, and household cleaners [61].
2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran-3-ol was the most abundant compound of all the volatile compounds from T. anguina buds, whose content was 38.71−42.71% and 39.62−42.64% in female and male buds, respectively. It was also the main aroma compound from pu-erh teas, a popular fermented tea that originated in Yunnan [33]. The content of 2,2,6-Trimethyl-6-vinyldihydro-2H-pyran-3(4H)-one was the second highest volatile compound in both buds of T. anguina. It also had a high content in the volatile compounds of Camellia sasanqua ‘Dongxing’ flowers (family Theaceae) [62].
The chemical components of some dioecious plants were reported to be different between females and males. The essential oils of the female and male aerial parts of Baccharis tridentata Vahl. (family Asteraceae) were explored with GC-MS analysis. α-Pinene was the main compound in the essential oil of both genders, which was presented at higher content in males (1173 ± 60 μg/L) than that in females (794 ± 40 μg/L). Conversely, the concentrations of α-phellandrene, α-terpinene, and trans-verbenol in female essential oil were higher than those in males [42]. The chemical components from female and male flowers of Schisandra chinensis (family Magnoliaceae) were differentiated with GC-MS analysis. The results showed that 16 compounds were found only in female flowers (including α-farnesene, α-pinene, and 3-carene), and 19 compounds (including p-xylene, 3-pyridinecarboxaldehyde, and 1,2-epoxydodecane) were detected only in male flowers. A number of compounds detected both in female and male flowers were quantitatively different; for example, the content of β-pinene in females was 6.36 times that in male flowers (0.70 ± 0.06% and 0.11 ± 0.01%, respectively) [51].
The plant T. kirilowii, a different species of the same genus of T. anguina, was a dioecious plant. The highest content component of T. kirilowii flowers was alcohol, the same as T. anguina buds. Some same compounds of linalool, benzyl alcohol, and (E)-linalool oxide were found both in T. anguina and T. kirilowii. However, the highest content compound in females was linalool, but in male flowers of T. kirilowii was benzyl alcohol. Some compounds, such as β-myrcene and α-ocimene, were only detected in females, and benzaldehyde was only detected in male flowers of T. kirilowii [14]. The difference between female and male flowers of T. kirilowii was larger than that between female and male buds of T. anguina. In other words, the difference in volatile compounds between the two genders from the dioecious plant was larger than that from the monoecious and diclinous plants. Dioecious plants have more advanced evolution than monoecious and diclinous plants in plant sexology [63]. From the perspective of the flowers and buds of sexual organs, the higher inequality was found based on their volatile compounds.

4. Materials and Methods

4.1. Apparatus and Materials

A Shimadzu GC-MS-QP 2010 plus gas chromatography-mass spectrometer and a Swiss CTC Combi-xt PAL three-in-one multifunctional automatic sampler were purchased from Shimadzu (Tokyo, Japan). A polyethylene glycol capillary chromatographic column INNOWAX (30 m × 0.25 mm, 0.25 µm) was purchased from Shanghai Troody Analysis Instrument Co., Ltd. (Shanghai, China). The SPME fiber 50/30 µm carboxen/polydimethylsiloxane/divinylbenzene (CAR/PDMS/DVB) was purchased from Supelco (Bellefonte, PA, USA). An ME 204/02 electronic balance was purchased from Mettler Toledo Instruments Co., Ltd. (Shanghai, China). An n-alkanes standard (C11–C32) was purchased from Sigma-Aldrich (St. Louis, MO, USA).

4.2. Sample Collection

The plant of T. anguina was planted in the courtyard of 16 Dongzhimen South Street, Dongcheng District, Beijing (39°56′18.45′′ N, 116°25′41.06′′ E, and 48 m altitude). On 6th August, just before their buds bloomed, male buds were picked from pedicels at 8 p.m., and female buds were taken from the top of their juvenile fruits at 9 p.m. The original plant was identified as Trichosanthes anguina L. (family Cucurbitaceae) by Prof. Zhimao Chao (Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences) according to the description in Flora of China (Editorial Board of Flora of China, 1984). The voucher specimens (TAF 1–3 and TAM 1–3) were deposited at the 1022 laboratory of the Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, China.

4.3. Sample Preparation

The fresh bud samples were collected and placed in 15 mL glass headspace bottles. Each headspace bottle was placed in one of the bud samples, tightly covered, weighed, and subtracted from the bottle’s body weight to obtain the sample weight. Moreover, the material of the headspace bottle gasket was polytetrafluoroethylene (PTFE). The 50/30 µm CAR/PDMS/DVB SPME fiber was aged at 260 °C for 30 min, extended through the needle, exposed into the headspace bottle to adsorb volatile compounds at 50 °C for 30 min, and immediately injected into the gas chromatography injection port at 250 °C for 3 min to desorb volatile compounds.

4.4. Chromatographic Conditions

The volatile compounds of the samples were analyzed by the GC-MS method. A GC-MS-QP 2010 plus gas chromatography-mass spectrometer was used coupled to polyethylene glycol capillary chromatographic column Agilent HP-INNOWAX (30 m × 0.25 mm, 0.25 µm). The splitless injection mode was used. The carrier gas was high-purity helium, which was used at a constant flow rate of 1.01 mL·min−1. The temperature of the injection port was set at 250 °C. The heating program was as follows: the initial temperature was 40 °C maintained for 8 min, raised to 160 °C at a rate of 3 °C·min−1, and subsequently raised to 240 °C at a rate of 10 °C·min−1 and held for 5 min.

4.5. MS Conditions

The electron ionization (EI) source was used and operated at 70 eV. The ion source temperature was 200 °C. The interface temperature was 220 °C. Moreover, the scanning range was m/z 29–350.

4.6. Data Processing

The volatile compounds from samples were identified with the mass spectrum and RI. The mass spectra obtained from the GC-MS experiments were compared with the National Institute of Standards and Technology (NIST) 14 spectrum library. The RIs were calculated according to the peak retention time of these volatile compounds and of the series of n-alkanes (C11–C32) under the same temperament condition and were compared with the values in the previous reports. The peak area normalization was carried out for semi-quantitative analysis and for comparison of the difference of the volatile compounds between female and male samples.

4.7. Statistical Analysis

OPLS-DA is a supervised discriminant analysis that can effectively distinguish the difference between groups. The experimental data were imported into SIMCA-P software (version 14.1, Umetrics, Malmö, Sweden) to establish an OPLS-DA model to distinguish the female and male buds. The experimental data were also imported into SPSS (version 19.0, IBM, America), analyzed with a t-test, and then combined with OPLS-DA results to identify the significantly different compounds of the volatile components from female and male buds of T. anguina.

4.8. Heat Map

After data were imported into the Metabo Analyst 5.0 website, the heat map was generated to visualize the distribution of different compounds in different samples so that readers could intuitively observe the content gap of these compounds in female and male samples.

5. Conclusions

In this study, HS-SPME-GC-MS combined with multivariate statistical analysis was used to explore some differences in volatile compounds of T. anguina buds, and it was found that there was a significant difference between female and male buds. A total of 53 volatile compounds were identified by GC-MS. There were the same volatile compounds from female and male buds, but their content was different. Based on multivariate statistical analysis, seven different compounds were screened out. Among them, the content of (E)-4,8-dimethyl-1,3,7-nonatriene, (E)-caryophyllene, and 1,5,9,9-tetramethyl-1,4,7-cycloundecatriene from male was higher than that from female buds, and the content of (Z)-4-hexen-1-ol, (Z)-3-hexenyl benzoate, (Z)-3-hexenyl salicylate, and 2-hexen-1-ol from male was lower than that from female buds. Further comparison between the monoecious and diclinous plant of T. anguina and the dioecious plant of T. kirilowii, an opinion suggested that the difference of volatile compounds between female and male buds of the monoecious and diclinous plant was smaller than that of the dioecious plant. This opinion was consistent with the evolutionary view of plant sex [63].
This is the first report that the difference in volatile compounds between female and male buds of T. anguina was analyzed. Furthermore, a comparison between monoecious and diclinous plants and dioecious plants was first carried out.

Author Contributions

Data curation, P.S.; Formal analysis, B.X.; Funding acquisition, Z.C.; Investigation, P.S.; Methodology, Z.L.; Resources, Z.C.; Validation, B.X. and Y.C.; Visualization, Y.C.; Writing—original draft, P.S.; Writing—review and editing, Z.C. All authors have read and agreed to the published version of the manuscript.

Funding

Thanks for the support of China Agriculture Research System of the Ministry of Finance and the Ministry of Agriculture and Rural Areas (CARS-21).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

All the relevant data have been provided in the manuscript. The authors will provide additional details if required.

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Raj, M.N.; Prasanna, K.P.; Peter, K.V. Snake gourd. Genet. Improv. Veg. Crop 1993, 223, 259–264. [Google Scholar]
  2. Ojiako, O.A.; Igwe, C.U. The Nutritive, Anti-Nutritive and Hepatotoxic Properties of Trichosanthes anguina (Snake Tomato) Fruits from Nigeria. Pak. J. Nutr. 2008, 7, 85–89. [Google Scholar] [CrossRef]
  3. Zong, J.; Cao, H.B. Nutrition and Scientific Consumption of 68 Special Vegetables; Jindun Press: Beijing, China, 2013; p. 36. [Google Scholar]
  4. Sandhya, S.; Vinod, K.R.; Chandra Sekhar, J.; Aradhana, R.; Nath, V.S. An updated review on Tricosanthes cucumerina L. Int. J. Pharm. Sci. Rev. Res. 2010, 1, 56–60. [Google Scholar]
  5. Churiyah, W.S. Antiproliferative protein from Trichosanthes cucumerina L. var anguina (L.) Haines. Biotropia Southeast Asian J. Trop. Biol. 2010, 17, 8–16. [Google Scholar]
  6. Takagi, T.; Itabashi, Y. Occurrence of mixtures of geometrical isomers of conjugated octadecatrienoic acids in some seed oils: Analysis by open-tubular gas liquid chromatography and high performance liquid chromatography. Lipids 1981, 16, 546–551. [Google Scholar] [CrossRef]
  7. Ali, M.A.; Sayeed, M.A.; Islam, M.S.; Yeasmin, M.S.; Khan, G.; Muhamad, I.I. Physicochemical and antimicrobial properties of Trichosanthes anguina and Swietenia mahagoni seeds. Bull. Chem. Soc. Ethiop. 2011, 25, 427–436. [Google Scholar] [CrossRef] [Green Version]
  8. Chao, Z.M. Review on chemical constituents of Trichosanthes. China J. Chin. Mater. Med. 1990, 15, 49–51. [Google Scholar]
  9. Venkataramaiah, C.; Rao, K.N. Studies on Indolyl-3-acetic Acid Oxidase and Phenolic Acid Pattern in Cucurbitaceous Fruits. Z. Pflanzenphysiol. 1983, 111, 459–463. [Google Scholar] [CrossRef]
  10. Yoshizaki, M.; Fujino, H.; Masuyama, M.; Arisawa, M.; Morita, N. A chemotaxonomic study of flavonoids in the leaves of six Trichosanthes species. Phytochemistry 1987, 26, 2557–2558. [Google Scholar] [CrossRef]
  11. Benesh, D.P.; Weinreich, F.; Kalbe, M.; Milinski, M. Lifetime inbreeding depression, purging, and mating system evolution in a simultaneous hermaphrodite tapeworm. Evolution 2014, 68, 1762–1774. [Google Scholar] [CrossRef]
  12. Xu, B.; Wu, C.; Li, Z.; Song, P.; Chao, Z. 1H NMR Combined with Multivariate Statistics for Discrimination of Female and Male Flower Buds of Populus tomentosa. Molecules 2021, 26, 6458. [Google Scholar] [CrossRef]
  13. Liu, Z.; Fang, Y.; Wu, C.; Hai, X.; Xu, B.; Li, Z.; Song, P.; Wang, H.; Chao, Z. The Difference of Volatile Compounds in Female and Male Buds of Herpetospermum pedunculosum Based on HS-SPME-GC-MS and Multivariate Statistical Analysis. Molecules 2022, 27, 1288. [Google Scholar] [CrossRef]
  14. Sun, W.; Chao, Z.; Wang, C.; Wu, X.; Tan, Z. [Difference of volatile constituents contained in female and male flowers of Trichosanthes kirilowii by HS-SPME-GC-MS]. China J. Chin. Mater. Medica 2012, 37, 1570–1574. [Google Scholar]
  15. Li, C.Q.; Lu, Y.; Li, X.Z.; Xing, H.; Kang, W.Y. Volatile constituents from flower of Tianmian Cucurbita moschata Duch. by head-space solid micro-extraction coupled with GC-MS. Sci. Technol. Food Ind. 2012, 33, 151–156. [Google Scholar]
  16. Freitas, L.; Bernardello, G.; Galetto, L.; Paoli, A.A.S. Nectaries and reproductive biology of Croton sarcopetalus (Euphorbiaceae). Bot. J. Linn. Soc. 2001, 136, 267–277. [Google Scholar] [CrossRef]
  17. Hawthorne, S.B.; Miller, D.J.; Pawliszyn, J.; Arthur, C.L. Solventless determination of caffeine in beverages using solid-phase microextraction with fused-silica fibers. J. Chromatogr. A 1992, 603, 185–191. [Google Scholar] [CrossRef]
  18. Zaitsev, V.N.; Zui, M.F. Preconcentration by solid-phase microextraction. J. Anal. Chem. 2014, 69, 715–727. [Google Scholar] [CrossRef]
  19. Sven, U. Solid-phase microextraction in biomedical analysis. J. Chromatogr. A 2000, 902, 167–194. [Google Scholar]
  20. Xu, L.; Liu, H.; Ma, Y.; Wu, C.; Li, R.; Chao, Z. Comparative study of volatile components from male and female flower buds of Populus × tomentosa by HS-SPME-GC-MS. Nat. Prod. Res. 2019, 33, 2105–2108. [Google Scholar] [CrossRef]
  21. Wawrzyniak, R.; Jasiewicz, B. Straightforward and rapid determination of acrylamide in coffee beans by means of HS-SPME/GC-MS. Food Chem. 2019, 301, 125264. [Google Scholar] [CrossRef]
  22. Bhavya, M.L.; Ravi, R.; Naidu, M.M. Development and validation of headspace Solid-Phase microextraction coupled with gas chromatography (HS-SPME-GC) method for the analysis of Zingiber zerumbet L. Nat. Prod. Res. 2021, 35, 1221–1225. [Google Scholar] [CrossRef] [PubMed]
  23. Cerkowniak, M.; Boguś, M.I.; Włóka, E.; Stepnowski, P.; Gołębiowski, M. Application of headspace solid-phase microextraction followed by gas chromatography coupled with mass spectrometry to determine esters of carboxylic acids and other volatile compounds in Dermestes maculatus and Dermestes ater lipids. Biomed. Chromatogr. 2018, 32, e4051. [Google Scholar] [CrossRef] [PubMed]
  24. Nešpor, J.; Karabín, M.; Štulíková, K.; Dostálek, P. An HS-SPME-GC-MS Method for Profiling Volatile Compounds as Related to Technology Used in Cider Production. Molecules 2019, 24, 2117. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  25. Yang, D.-S.; Lei, Z.; Bedair, M.; Sumner, L.W. An Optimized SPME-GC-MS Method for Volatile Metabolite Profiling of Different Alfalfa (Medicago sativa L.) Tissues. Molecules 2021, 26, 6473. [Google Scholar] [CrossRef]
  26. Zhang, R.; Tang, C.; Jiang, B.; Mo, X.; Wang, Z. Optimization of HS-SPME for GC-MS Analysis and Its Application in Characterization of Volatile Compounds in Sweet Potato. Molecules 2021, 26, 5808. [Google Scholar] [CrossRef]
  27. Lee, J.H.J.; Jayaprakasha, G.K.; Rush, C.M.; Crosby, K.M.; Patil, B.S. Production system influences volatile biomarkers in tomato. Metabolomics 2018, 14, 99. [Google Scholar] [CrossRef]
  28. Cecchi, L.; Migliorini, M.; Giambanelli, E.; Cane, A.; Mulinacci, N.; Zanoni, B. Volatile Profile of Two-Phase Olive Pomace (Alperujo) by HS-SPME-GC–MS as a Key to Defining Volatile Markers of Sensory Defects Caused by Biological Phenomena in Virgin Olive Oil. J. Agric. Food Chem. 2021, 69, 5155–5166. [Google Scholar] [CrossRef]
  29. An, H.M.; Ou, X.C.; Xiong, Y.F.; Zhang, Y.B.; Li, J.; Li, Q.; Li, Q.; Li, S.; Huang, J.A. Study on the characteristic aroma components of jasmine tea. J. Tea Sci. 2020, 40, 225–237. [Google Scholar]
  30. Carriero, G.; Brunetti, C.; Fares, S.; Hayes, F.; Hoshika, Y.; Mills, G.; Tattini, M.; Paoletti, E. BVOC responses to realistic nitrogen fertilization and ozone exposure in silver birch. Environ. Pollut. 2016, 213, 988–995. [Google Scholar] [CrossRef]
  31. Conde-Martínez, N.; Sinuco, D.C.; Osorio, C. Chemical studies on curuba (Passiflora mollissima (Kunth) L. H. Bailey) fruit flavour. Food Chem. 2014, 157, 356–363. [Google Scholar] [CrossRef]
  32. Falahati, M.; Sepahvand, A.; Mahmoudvand, H.; Baharvand, P.; Jabbarnia, S.; Ghojoghi, A.; Yarahmadi, M. Evaluation of the antifungal activities of various extracts from Pistacia atlantica Desf. Curr. Med. Mycol. 2015, 1, 25–32. [Google Scholar] [CrossRef] [PubMed]
  33. Nian, B.; Jiao, W.W.; He, M.Z.; Liu, Q.T.; Zhou, L.X.; Jiang, B.; Zhang, Z.Y.; Liu, M.L.; Ma, Y.; Chen, L.J.; et al. Determination and comparison of biochemical components and aroma substances in the pu-erh teas with mellow flavor and floral-fruity aroma. Mod. Food Sci. Technol. 2020, 36, 241–248. [Google Scholar]
  34. Wang, G.-C.; Sun, X.-L.; Cai, X.-M.; Chen, Z.-M. Effects of tea plant volatiles on foraging behavior of Xysticus ephippiatus Simon. Chin. J. Eco-Agric. 2012, 20, 612–618. [Google Scholar] [CrossRef]
  35. Zhang, H.; Zhou, D.; Luo, Y.; Wang, J.; Zong, S. Identification of volatile compounds emitted by Artemisia ordosica (Artemisia, Asteraceae) and changes due to mechanical damage and weevil infestation. Z. Naturforsch. C J. Biosci. 2013, 68, 313. [Google Scholar] [CrossRef] [PubMed]
  36. Wei, J.-F.; Yin, Z.-H.; Kang, W.-Y. Volatiles of Lysimachia Paridiformis Var. Stenophylla, Lysimachia Fortumei and Lysimachia Chikungensis by HS-SPME-GC-MS. Afr. J. Tradit. Complement. Altern. Med. 2014, 11, 70–75. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  37. Marín-San Román, S.; Carot, J.M.; Sáenz de Urturi, I.; Rubio-Bretón, P.; Pérez-Álvarez, E.P.; Garde-Cerdán, T. Optimization of thin film-microextraction (TF-SPME) method in order to determine musts volatile compounds. Anal. Chim. Acta. 2022, 1226, 340254. [Google Scholar] [CrossRef] [PubMed]
  38. Wang, H.Y.; Zhang, W.; Dong, J.H.; Wu, H.; Wang, Y.H.; Xiao, H.X. Optimization of SPME-GC-MS and characterization of floral scents from Aquilegia japonica and A. amurensis flowers. BMC Chem. 2021, 15, 26. [Google Scholar] [CrossRef]
  39. Qader, K.O.; Salah, T.F.M.; Rasul, A.A. GC-MS analysis of essential oil Extract from leaves and stems of tarragon (Artemisia dracunculus L.). J. Biol. Agric. Healthc. 2017, 7, 50–57. [Google Scholar]
  40. Cao, Y.; Wang, J.; Germinara, G.S.; Wang, L.; Yang, H.; Gao, Y.; Li, C. Behavioral Responses of Thrips hawaiiensis (Thysanoptera: Thripidae) to Volatile Compounds Identified from Gardenia jasminoides Ellis (Gentianales: Rubiaceae). Insects 2020, 11, 408. [Google Scholar] [CrossRef]
  41. Zhang, T.; Bao, F.; Yang, Y.; Hu, L.; Ding, A.; Ding, A.; Wang, J.; Cheng, T.; Zhang, Q. A Comparative Analysis of Floral Scent Compounds in Intraspecific Cultivars of Prunus mume with Different Corolla Colours. Molecules 2019, 25, 145. [Google Scholar] [CrossRef]
  42. Minteguiaga, M.; Fariña, L.; Cassel, E.; Fiedler, S.; Catalán, C.A.N.; Dellacassa, E. Chemical compositions of essential oil from the aerial parts of male and female plants of Baccharis tridentata Vahl. (Asteraceae). J. Essent. Oil Res. 2021, 33, 299–307. [Google Scholar] [CrossRef]
  43. Jagannath, S.; Konappa, N.; Lokesh, A.; Bhuvaneshwari; Dasegowda, T.; Udayashankar, A.C.; Chowdappa, S.; Cheluviah, M.; Satapute, P.; Jogaiah, S. Bioactive compounds guided diversity of endophytic fungi from Baliospermum montanum and their potential extracellular enzymes. Anal. Biochem. 2021, 614, 114024. [Google Scholar] [CrossRef] [PubMed]
  44. Shi, M.Z.; Li, J.Y.; Chen, Y.T.; Fang, L.; Wei, H.; Fu, J.W. Plant volatile compounds of the Invasive Alligatorweed, Alternanthera philoxeroides (Mart.) Griseb, infested by Agasicles hygrophila Selman and Vogt (Coleoptera: Chrysomelidae). Life 2022, 12, 1257. [Google Scholar] [CrossRef]
  45. Günther, J.; Lackus, N.D.; Schmidt, A.; Huber, M.; Stödtler, H.-J.; Reichelt, M.; Gershenzon, J.; Köllner, T.G. Separate Pathways Contribute to the Herbivore-Induced Formation of 2-Phenylethanol in Poplar. Plant Physiol. 2019, 180, 767–782. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  46. Omarini, A.; Dambolena, J.S.; Lucini, E.; Mejía, S.J.; Albertó, E.; Zygadlo, J.A. Biotransformation of 1,8-cineole by solid-state fermentation of Eucalyptus waste from the essential oil industry using Pleurotus ostreatus and Favolus tenuiculus. Folia Microbiol. 2016, 61, 149–157. [Google Scholar] [CrossRef]
  47. Kaya, M.; Merdivan, M.; Tashakkori, P.; Erdem, P.; Anderson, J.L. Analysis of Echinacea flower volatile constituents by HS-SPME-GC/MS using laboratory-prepared and commercial SPME fibers. J. Essent. Oil Res. 2019, 31, 91–98. [Google Scholar] [CrossRef]
  48. Panahi, Y.; Ghanei, M.; Hadjiakhoondi, A.; Ahmadi-Koulaei, S.; Delnavazi, M.-R. Free Radical Scavenging Principles of Salvia reuterana Boiss. Aerial Parts. Iran J. Pharm. Res. 2020, 19, 283–290. [Google Scholar] [CrossRef]
  49. Badra, Z.; Herrera, S.L.; Cappellin, L.; Biasioli, F.; Dekker, T.; Angeli, S.; Tasin, M. Species-Specific Induction of Plant Volatiles by Two Aphid Species in Apple: Real Time Measurement of Plant Emission and Attraction of Lacewings in the Wind Tunnel. J. Chem. Ecol. 2021, 47, 653–663. [Google Scholar] [CrossRef]
  50. Akinkunmia, E.O.; Oladeleb, A.; Eshoa, O.; Oduseguna, I. Effects of storage time on the antimicrobial activities and composition of lemon grass oil. J. Appl. Res. Med. Aromat. Plants 2016, 3, 105–111. [Google Scholar] [CrossRef]
  51. Sowndhararajan, K.; Kim, J.-H.; Song, J.E.; Kim, M.; Kim, S. Chemical components of male and female flowers of Schisandra chinensis. Biochem. Syst. Ecol. 2020, 92, 104121. [Google Scholar] [CrossRef]
  52. Wei, H.S.; Qin, J.H.; Cao, Y.Z.; Li, K.B.; Yin, J. Two classic OBPs modulate the responses of female Holotrichia oblita to three major ester host plant volatiles. Insect Mol. Biol. 2021, 30, 390–399. [Google Scholar] [CrossRef] [PubMed]
  53. Eseyin, O.A.; Sattar, M.A.; Rathore, H.; Aigbe, F.; Afzal, S.; Ahmad, A.; Lazhari, M.; Akthar, S. GC-MS and HPLC profiles of phenolic fractions of the leaf of Telfairia occidentalis. Pak. J. Pharm. Sci. 2018, 31, 45–50. [Google Scholar] [PubMed]
  54. Gao, D.-W.; Wen, Z.-D. Phthalate esters in the environment: A critical review of their occurrence, biodegradation, and removal during wastewater treatment processes. Sci. Total Environ. 2016, 541, 986–1001. [Google Scholar] [CrossRef]
  55. Azuma, H.; Toyota, M.; Asakawa, Y. Intraspecific Variation of Floral Scent Chemistry in Magnolia kobus DC. (Magnoliaceae). J. Plant Res. 2001, 114, 411–422. [Google Scholar] [CrossRef]
  56. Svensson, G.P.; Hickman, M.O., Jr.; Bartram, S.; Boland, W.; Pellmyr, O.; Raguso, R.A. Chemistry and geographic variation of floral scent in Yucca filamentosa (Agavaceae). Am. J. Bot. 2005, 92, 1624–1631. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  57. Li, W.; Lin, Y.J.; Zhou, F. The recent research progress on DMNT and TMTT in plants. J. Plant Prot. 2018, 45, 946–953. [Google Scholar]
  58. Francomano, F.; Caruso, A.; Barbarossa, A.; Fazio, A.; La Torre, C.; Ceramella, J.; Mallamaci, R.; Saturnino, C.; Iacopetta, D.; Sinicropi, M.S. β-(E)-Caryophyllene: A sesquiterpene with countless biological properties. Appl. Sci. 2019, 9, 5420. [Google Scholar] [CrossRef] [Green Version]
  59. Wang, C.-F.; Yang, K.; You, C.-X.; Zhang, W.-J.; Guo, S.-S.; Geng, Z.-F.; Du, S.-S.; Wang, Y.-Y. Chemical Composition and Insecticidal Activity of Essential Oils from Zanthoxylum dissitum Leaves and Roots against Three Species of Storage Pests. Molecules 2015, 20, 7990–7999. [Google Scholar] [CrossRef]
  60. Wang, Z.; Yang, F.; Sun, A.; Song, J.; Shan, S.; Zhang, Y.; Wang, S. Expressional and functional comparisons of five clustered odorant binding proteins in the brown marmorated stink bug Halyomorpha halys. Int. J. Biol. Macromol. 2022, 206, 759–767. [Google Scholar] [CrossRef]
  61. Lapczynski, A.; McGinty, D.; Jones, L.; Letizia, C.S.; Api, A.M. Fragrance material review on cis-3-hexenyl salicylate. Food Chem. Toxicol. 2007, 45, S402–S405. [Google Scholar] [CrossRef]
  62. Wang, J.; Li, X.L.; Yin, H.F.; Fan, Z.Q.; Li, J.Y. Volatile components in different floral organs and flowering stages of Camellia sasanqua ‘Dongxing’. J. Yunnan Agric. Univ. Nat. Sci. 2018, 33, 904–910. [Google Scholar]
  63. Husband, B.C.; Schemske, D.W. Evolution of the magnitude and timing of inbreeding. Evolution 1996, 50, 54. [Google Scholar] [CrossRef] [PubMed]
Molecules 27 07021 g001 550
Figure 1. The female flower (a), male flower (b), and tender fruit (c) of T. anguina.
Figure 1. The female flower (a), male flower (b), and tender fruit (c) of T. anguina.
Molecules 27 07021 g001
Molecules 27 07021 g002 550
Figure 2. GC-MS total ion chromatogram of volatile compounds of sample f2.
Figure 2. GC-MS total ion chromatogram of volatile compounds of sample f2.
Molecules 27 07021 g002
Molecules 27 07021 g003 550
Figure 3. GC-MS total ion chromatograms of volatile compounds from female and male buds of T. anguina.
Figure 3. GC-MS total ion chromatograms of volatile compounds from female and male buds of T. anguina.
Molecules 27 07021 g003
Molecules 27 07021 g004 550
Figure 4. OPLS−DA arranges the verification diagram (a), scores (R2 = 0.944; Q2 = 0.838) (b), and S−plot (c) between female and male buds of T. anguina. The numbers of the S−plot in Figure (c) were consistent with the no. in Table 1.
Figure 4. OPLS−DA arranges the verification diagram (a), scores (R2 = 0.944; Q2 = 0.838) (b), and S−plot (c) between female and male buds of T. anguina. The numbers of the S−plot in Figure (c) were consistent with the no. in Table 1.
Molecules 27 07021 g004
Molecules 27 07021 g005 550
Figure 5. The heatmap of the differential compounds in female and male buds of T. anguina. The numbers of the heat map were consistent with the no. in Table 1.
Figure 5. The heatmap of the differential compounds in female and male buds of T. anguina. The numbers of the heat map were consistent with the no. in Table 1.
Molecules 27 07021 g005
Table
Table 1. Volatile compounds of GC-MS analysis of female and male T. anguina buds.
Table 1. Volatile compounds of GC-MS analysis of female and male T. anguina buds.
No.RICompoundMFFragment
(m/z)		CASRelative Content/%Reports
FemaleMale
f1f2f3m1m2m3
112143-Methyl-1-butanolC5H12O87/70/57/55123-51-32.002.672.292.582.412.30-
21239(E)-3,7-Dimethyl-
1,3,6-octatriene		C10H16136/121/93/773779-61-10.210.180.120.090.130.19Jasmine tea [29]
312561-Chloro-3-methylbutaneC5H11Cl106/91/42/27107-84-60.230.300.320.210.190.23-
41311(E)-4,8-Dimethyl-1,3,7-
nonatriene		C11H18150/135/69/5319945-61-00.580.620.502.244.633.57Grevillea robusta [30]
51322(Z)-3-Hexenyl acetateC8H14O282/67/543681-71-80.230.410.270.210.170.21Passiflora mollissima [31]
61341(Z)-2-Hexenyl acetateC8H14O2142/100/67/5556922-75-90.410.690.400.430.370.49-
713591-HexanolC6H14O101/84/69/56111-27-30.410.540.610.560.470.59-
81375(E,Z)-2,6-Dimethylocta-
2,4,6-triene		C10H16136/121/105/797216-56-00.130.110.050.070.090.14Pistacia atlantica [32]
91389(Z)-4-Hexen-1-olC6H12O100/82/67/55928-91-61.902.192.111.291.311.40-
1014122-Hexen-1-olC6H12O100/82/57928-95-01.061.131.030.810.750.86Olive oil [28]
111443(E)-2-Methyl-2-vinyl-
(1-hydroxy-1-
methylethyl)tetrahydrofuran		C10H18O2111/94/68/5934995-77-20.500.510.430.410.370.40Pu-erh tea [33]
1214732,2,6-Trimethyl-6-vinyldihydro-
2H-pyran-3(4H)-one		C12H20O3168/110/82/6833933-72-130.2835.8227.4428.9128.3432.95-
131480(E)-2-Hexenyl butyrateC10H18O2170/155/71/5553398-83-70.070.080.070.060.060.05Longjing tea [34]
1414848-Isopropyl-1,3-dimethyltricyclo
[4.4.0.0(2,7)]dec-3-ene		C15H24204/161/119/
105/81/55		138874-68-70.070.070.050.070.100.10Artemisia ordosica [35]
151493(Z)-3-Hexenyl pentanoateC11H20O2103/82/67/5535852-46-10.090.130.240.090.050.06Lysimachia paridiformis [36]
161506(E)-2-Hexenyl pentanoateC11H20O2184/169/85/5756922-74-80.190.220.410.200.160.16-
1715268,8-Dimethoxyoct-2-yl 2-
formyl-4,6-dimethoxybenzoate		C20H30O7209/193/165/71312305-58-10.180.180.250.200.230.18-
1815563,7-Dimethyl-1,6-octadien-3-olC10H18O136/121/
93/71/55		78-70-60.030.020.020.020.010.01La Rioja grape [37]
191588(E)-4,11,11-Trimethyl-
8-methylene-bicyclo
[7.2.0]undec-4-ene		C15H24205/189/161/
133/107/93/69		87-44-51.791.921.732.102.522.49Aquilegia japonica [38]
2016303-Acetoxy-2,2,6-trimethyl-
6-vinyltetrahydropyran		C12H20O3197/179/155/
137/94/68/55		67674-42-40.380.730.340.530.360.58-
2116601,5,9,9-Tetramethyl-1,4,7-
cycloundecatriene		C15H24204/189/161/
147/121/93/80		515812-15-41.101.150.981.231.541.49Artemisia dracunculus [39]
221670(Z)-3-Hexenyl tiglateC11H18O2101/83/67/5567883-79-80.080.100.040.160.290.29Gardenia jasminoides [40]
231675(E)-2-Hexenyl hexanoateC12H22O2198/169/99/7153398-86-00.130.130.140.080.060.06Longjing tea [34]
241733Benzyl acetateC9H10O2150/128/91/79140-11-40.260.160.280.240.210.20Prunus mume [41]
2517531-Isopropyl-7-methyl-4-
methylene-1,2,3,4,4a,5,6,8a-
octahydronaphthalene		C15H24204/161/10524268-39-10.450.450.350.450.560.60Baccharis tridentata [42]
2617752,2,6-Trimethyl-6-
vinyltetrahydro-2H-pyran-3-ol		C10H18O2170/152/137/
109/94/68		14049-11-742.7138.7141.7142.6440.5939.62Pu-erh tea [33]
271783Methyl N-hydroxy
benzenecarboximidate		C8H9NO2151/133/105/7367160-14-90.450.360.910.580.480.38Endophytic fungi from Baliospermum montanum [43]
2817971-(2-Butoxyethoxy)ethanolC8H18O3132/100/75/5754446-78-50.090.070.070.070.050.05-
291812(3E,7E)-4,8,12-Trimethyltrideca-
1,3,7,11-tetraene		C16H26218/203/175/
137/95/69/53		62235-06-70.350.340.340.230.160.23Invasive alligatorweed [44]
301880PhenylmethanolC7H8O108/91/79/65100-51-61.330.681.360.941.060.74Prunus mume [41]
3119132-PhenylethanolC8H10O122/91/77/6560-12-82.812.184.872.332.831.64Populus trichocarpa [45]
3219317,11,15-Trimethyl-3-
methylenehexadec-1-ene		C20H38278/263/137/
123/95/68/57		504-96-10.170.110.400.280.330.25Herpetospermum pedunculosum [13]
331949BenzothiazoleC7H5NS135/108/95/6995-16-90.250.230.260.240.290.24Tomato [27]
3420221,3,3-Trimethyl-2-
oxabicyclo[2.2.2]octan-6-ol		C10H18O2170/143/126/
108/93/71		60761-00-40.240.090.190.230.140.17Pleurotus ostreatus and Favolus tenuiculus [46]
3520263,7-Dimethylocta-
1,6-dien-3-yl formate		C11H18O2182/165/136/
121/93/69		115-99-10.120.090.130.100.060.06-
362048Isopentyl 2-hydroxybenzoateC12H16O3208/193/165/
138/120/92		87-20-70.200.230.390.270.110.15-
372053(E)-3,7,11-Trimethyldodeca-
1,6,10-trien-3-ol		C15H26O189/161/107/
93/69		40716-66-30.140.100.150.140.130.11Echinacea flower [47]
382078Hexyl benzoateC13H18O2206/123/105/776789-88-40.600.580.710.670.440.42Salvia reuterana [48]
392128(Z)-3-Hexenyl benzoateC13H16O2105/82/6725152-85-61.281.031.480.820.580.52Apple [49]
4021316,10,14-Trimethyl
pentadecan-2-one		C18H36O250/165/137/
109/95/71/58		502-69-20.300.260.170.260.220.53-
4121414-(3,3-Dimethyloxiran-2-yl)-2-
(oxiran-2-yl)butan-2-ol		C10H18O3143/102/
84/69/55		1365-19-10.150.050.110.120.060.10Lemon grass oil [50]
422151(E)-2-Hexenyl benzoateC13H16O2204/105/7776841-70-80.640.320.560.450.430.33-
4321731,6-Dimethyl-4-propan-2-yl-
3,4,4a,7,8,8a-hexahydro-
2H-naphthalen-1-ol		C15H26O204/189/161/
147/119/105		5937-11-10.200.140.200.270.360.35-
442213Hexyl 2-hydroxybenzoateC13H18O3222/138/120/92259-76-30.090.080.110.190.110.12-
4522364-Isopropyl-1,6-dimethyl-
1,2,3,4,4a,7,8,8a-
octahydronaphthalen-1-ol		C15H26O204/161/121/9581-34-50.050.020.060.080.100.11Schisandra chinensis [51]
462288(Z)-Hex-3-en-1-yl 2-
hydroxybenzoate		C13H16O3220/138/120/
82/67/55		65405-77-81.060.691.000.610.420.37Ulmus pumila [52]
4722962,3-Dihydroxypropyl acetateC5H10O4134/103/74106-61-60.060.110.030.060.130.06-
4823494,4,7a-Trimethyl-5,6,7,7a-
tetrahydrobenzofuran-2(4H)-one		C11H16O2180/137/111/6715356-74-80.060.050.070.090.060.07-
4923841-Methyl-4-[(2Z)-6-
methylhepta-2,5-dien-2-yl]-7-
oxabicyclo[4.1.0]heptane		C15H24O107/93/79/55121467-35-40.010.010.010.010.010.01-
502446Benzoic acidC7H6O2122/105/77/5165-85-00.060.060.070.060.060.05Telfairia occidentalis [53]
512556Diisobutyl phthalateC16H22O4281/167/149/5784-69-50.090.110.090.090.110.10-
522743Di(phenethyl) diglycolateC20H22O5342/104/7784-69-50.790.331.500.981.750.56-
532817Benzyl 2-hydroxybenzoateC14H12O3228/109/91/65118-58-10.710.250.541.391.380.66-
RI: retention index; MF: molecular formula.
Table
Table 2. The relative content of different types of volatile compounds in female and male T. anguina buds.
Table 2. The relative content of different types of volatile compounds in female and male T. anguina buds.
Type of CompoundsNumber of CompoundsRelative Content/%p-Value
f1f2f3 f ¯ m1m2m3 m ¯
Alcohols89.639.4812.3610.498.608.897.598.360.10
Ketones10.300.260.170.240.260.220.530.340.42
Non-aromatic esters91.381.961.731.691.391.351.441.390.16
Aromatic esters115.903.966.915.595.915.773.615.100.69
Monoterpenes40.950.70.80.820.850.630.740.740.47
Sesquiterpenes72.712.712.552.663.123.783.773.560.02
Diterpenes10.170.110.40.230.280.330.250.290.55
Alkenes52.372.41.992.253.866.555.625.340.02
Oximes10.450.360.910.570.580.480.380.480.63
Heterocycles473.6275.4969.7572.9572.3269.5873.3971.760.59
Alkanes10.230.300.320.280.210.190.230.210.07
Acids10.060.060.070.060.060.060.050.060.23
Table
Table 3. Differential volatile compounds between female and male buds of T. anguina.
Table 3. Differential volatile compounds between female and male buds of T. anguina.
SectionNo.CompoundVIP
A4(E)-4,8-Dimethyl-1,3,7-nonatriene3.68
A19(E)-Caryophyllene1.57
A211,5,9,9-Tetramethyl-1,4,7-cycloundecatriene1.25
B9(Z)-4-Hexen-1-ol1.81
B39(Z)-3-Hexenyl benzoate1.60
B46(Z)-3-Hexenyl salicylate1.30
B102-Hexen-1-ol1.10
A: higher in males than in females; B: higher in females than in males.
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Share and Cite

MDPI and ACS Style

Song, P.; Xu, B.; Liu, Z.; Cheng, Y.; Chao, Z. The Difference of Volatile Compounds in Female and Male Buds of Trichosanthes anguina L. Based on HS-SPME-GC-MS and Multivariate Statistical Analysis. Molecules 2022, 27, 7021. https://doi.org/10.3390/molecules27207021

AMA Style

Song P, Xu B, Liu Z, Cheng Y, Chao Z. The Difference of Volatile Compounds in Female and Male Buds of Trichosanthes anguina L. Based on HS-SPME-GC-MS and Multivariate Statistical Analysis. Molecules. 2022; 27(20):7021. https://doi.org/10.3390/molecules27207021

Chicago/Turabian Style

Song, Pingping, Bo Xu, Zhenying Liu, Yunxia Cheng, and Zhimao Chao. 2022. "The Difference of Volatile Compounds in Female and Male Buds of Trichosanthes anguina L. Based on HS-SPME-GC-MS and Multivariate Statistical Analysis" Molecules 27, no. 20: 7021. https://doi.org/10.3390/molecules27207021

Article Metrics

Back to TopTop