Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland
1
Institute of General Food Chemistry, Faculty of Biotechnology and Food Sciences, Łódź University of Technology, Stefanowskiego street 4/10, 90-924 Łódź, Poland
2
Maj Institute of Pharmacology, Polish Academy of Sciences, Department of Phytochemistry, Smętna street 12, 31-343 Kraków, Poland
*
Author to whom correspondence should be addressed.
Molecules 2019, 24(23), 4418; https://doi.org/10.3390/molecules24234418
Submission received: 31 October 2019
/
Revised: 29 November 2019
/
Accepted: 2 December 2019
/
Published: 3 December 2019
(This article belongs to the Special Issue Progress in Volatile Organic Compounds Research)
Abstract
:Carpesium divaricatum Sieb. and Zucc. has long been used both as traditional medicine and seasonal food. The most extensively studied specialized metabolites synthesized by the plant are sesquiterpene lactones of germacrane-type. Low-molecular and volatile terpenoids produced by C. divaricatum, however, have never been explored. In this work, compositions of essential oils distilled from roots and shoots of C. divaricatum plants, cultivated either in the open field or in the glasshouse have been studied by GC-MS-FID supported by NMR spectroscopy. The analyses led to the identification of 145 compounds in all, 112 of which were localized in aerial parts and 80 in roots of the plants grown in the open field. Moreover, remarkable differences in composition of oils produced by aerial and underground parts of C. divaricatum have been observed. The major volatiles found in the shoots were: α-pinene (40%), nerol (4%) and neryl-isobutyrate (3%), whereas predominant components of the root oil were 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate (29%), thymyl-isobutyrate (6%) and 9-isobutyryloxythymyl-isobutyrate (6%). In the analyzed oils, seventeen thymol derivatives were identified. Among them eight compounds were specific for roots. Roots of the plants cultivated in the glasshouse were, in general, a poor source of essential oil in comparison with those of the plants grown in the open field. Chemophenetic relationships with other taxa of the Inuleae-Inulineae were also briefly discussed.
1. Introduction
Plant genera of the subtribe Inuleae-Inulinae (family Asteraceae), e.g., Inula, Pulicaria, Telekia, Dittrichia, Blumea and Chiliadenus, are known to produce essential oils containing biologically active mono- and sesquiterpenoids [1,2,3]. Essential oils from Carpesium spp. are less studied. To our knowledge, only two communications on essential oil from the herb of C. abrotanoides L., the species included in the Chinese pharmacopoeia, have been published to date [4,5]. C. divaricatum Sieb. and Zucc. is a medicinal and food plant rich in terpenoid metabolites [6,7,8,9]. Recently, hydroxycinnamates and biologically active oxylipin from aerial parts of the plant have been also described [10]. According to the recent taxonomic studies [11,12], Telekia speciosa (Schreb.) Baumg. as well as some species of the genus Inula, known as essential oil bearing plants, are closely related to C. divaricatum. However, the content and composition of essential oils from C. divaricatum has remained unknown until now. The aim of the present study was to investigate the volatile compounds from roots and aerial parts of C. divaricatum and to compare the newly generated data with those reported previously for the related species.
2. Results
Unlike in its natural habitat, in our climate C. divaricatum is an annual plant. Moreover, due to late flowering, the plants grown in the open field failed to produce seeds. Fertile seeds were obtained only from the plants cultivated in a glasshouse. Yields of essential oils produced by the aerial parts of the plants were low (<0.02%, see Table 1) and except for the variations in percentages of individual compounds, oils distilled from shoots of the field grown plants and from the aerial parts of plants cultivated in a glasshouse demonstrated some minor qualitative differences in their composition (112 versus 89 identified constituents). The major compounds found in the essential oil from shoots of C. divaricatum were: α-pinene (c. 40% of oil), nerol (2.1%–3.7%) and neryl isobutyrate (3.2%–3.9%). Identified thymol derivatives (compounds: 54, 73, 84, 85, 111, 130, 142, 148 and 149, see Figure 1) constituted c. 6% of the oil. Roots of the plant turned out to be much better source of volatile terpenoids (yield of essential oil—0.15%). In contrast to the aerial parts (Figure 2), they contained only low amount of α-pinene (up to 1.8% of the essential oil). Thymol derivatives (17 identified structures, see Figure 1) accounted for over 60% and 44% of the essential oil from roots of the garden grown plants and plants cultivated in the glasshouse, respectively. 10-Isobutyryloxy-8,9-epoxythymyl isobutyrate was the major constituent of the analyzed root oils (18.1%–29.2%).
The essential oils from C. divaricatum contained some volatiles, which were difficult to identify based on GC-MS only. Flash chromatography (FC), monitored by thin-layer chromatography (TLC), was used to obtain fractions of oils rich in components of interest (purity 19%–63%, by GC-FID). The fractions were subsequently subjected to NMR analysis and the experimental chemical shifts of the chosen volatiles were compared to the literature data (see Supplementary Material).
Structures of 11 components remained unresolved, due to the small available amounts of the compounds, insufficient to perform full spectral analysis. MS spectra and retention indices of the compounds are shown in Supplementary Material.
3. Discussion
Though the essential oil content in aerial parts of C. divaricatum was very low, the occurrence of α-pinene (40% of the oil) is worth to note. The compound demonstrated anxiolytic and moderate anti-inflammatory effect in mice [13,14]. Essential oils obtained from plants of different provenience can markedly vary in their composition. Aerial parts of Pulicaria gnaphalodes (Vent.) Boiss., collected in four different locations, contained extremely different quantities of α-pinene (0.0–34.1% of the essential oil) [15]. Thus, some data on the composition of essential oils from C. divaricatum plants grown in their natural habitat would be of interest, to establish whether or not the high α-pinene content is typical of C. divaricatum aerial parts. Not much is known from the literature on essential oils from plants of the genus Carpesium. To date, only two studies on volatiles from the whole herb of C. abrotanoides have been published [4,5]. However, the authors managed to identify 14–44 components of the oils and neither α-pinene nor thymol derivatives have been detected. The major constituents were β-bisabolene (7.3–24.7%), caryophyllene-oxide (c. 13%) and eudesma-5,11(13)-dien-8,12-olide (c. 22%). Volatile constituents from other species of the Inuleae-Inulinae subtribe are better investigated. Thymol and its derivatives seem to be widespread within the plants of the subtribe, except for Blumea spp. [16,17,18]. The genus Pulicaria comprises species with essential oils rich in thymol and its methyl ether, like Pulicaria vulgaris Gaertn. [19] and Pulicaria sicula (L.) Moris [15] together with some species devoid of thymol derivatives [20]. The content of thymol derivatives in essential oil from aerial parts of C. divaricatum (6.4%) is similar to those detected in oils from aerial parts of other species of the subtribe, e.g., Schizogyne sericea (L.F.) DC. [21,22], Telekia speciosa (Schreb.) Baumg. [23,24] and Limbarda crithmoides (L.) Dumort. (formerly Inula crithmoides L.) [25]. Structural diversity of the compounds was also similar, with numerous thymol esters.
Essential oils from roots of the Inuleae-Inulinae plants have rarely been studied. Literature data on a few species are available, including Dittrichia viscosa (L.) Greuter (formerly Inula viscosa (L.) Aiton) [26], Inula racemosa Hook. f. [27,28], Inula helenium L. [1], Pulicaria mauritanica Coss. [29] and T. speciosa [24,30]. The common feature of essential oils from I. helenium, I. racemosa and T. speciosa is a very high content of eudesmane-type sesquiterpene lactones (up to 82%). Such composition of essential oils seems to be correlated with a presence of resin canals in roots of the plants. Thymol derivatives were not described as constituents of essential oil from roots of I. racemosa. The compounds, however, were found in the oils from the remaining species. Juvenile roots of I. helenium and I. viscosa contained higher amounts of the monoterpenoids than the old ones [26,31]. Two derivatives of thymol methyl ether constituted nearly 80% of the volatile fraction from I. viscosa roots [26]. Thymol, thymol methyl ether and eight thymyl ester derivatives accounted for c. 5.5% of the essential oil from roots of T. speciosa. P. mauritanica root oil contained c. 16% of the structurally related compounds. Though there are no any data on essential oils from roots of Carpesium spp., some thymol derivatives were described as constituents of methanol extract from aerial parts of C. divaricatum [32]. All of the compounds were found in essential oils from the plants analyzed in this study. Volatile fraction from roots of C. divaricatum is exceptional, in respect of both thymol derivatives content (over 60%) and their structural diversity (17 compounds; for MS spectra see Supplementary Material). 10-Isobutyryloxy-8,9-epoxy-thymyl isobutyrate, major constituent of the analyzed essential oil, demonstrated moderate activity against Staphylococcus aureus and Candida albicans [33].
4. Materials and Methods
4.1. General Experimental Procedures
GC-MS-FID analyses of essential oils and their fractions were performed on a Trace GC Ultra Gas Chromatograph coupled with DSQII mass spectrometer (Thermo Electron, Waltham, MA, USA). Simultaneous GC-FID and GC-MS analysis were performed using a MS-FID splitter (SGE Analytical Science, Ringwood, VIC, Australia). Mass range was 33–550 amu, ion source-heating: 200 °C; ionization energy: 70 eV. One microliter of essential oil solution (80% v/v) diluted in pentane:diethyl ether was injected in split mode at split ratios (50:1). Operating conditions: capillary column Rtx-1 MS (60 m × 0.25 mm i.d., film thickness 0.25 μm), and temperature program: 50 °C (3 min)—300 °C (30 min) at 4 °C/min. Injector and detector temperatures were 280 °C and 300 °C, respectively. Carrier gas was helium (constant pressure: 300 kPa). The relative composition of each essential oil sample was calculated from GC peak areas according to total peak normalization—the most popular method used in the essential oil analysis. 1H-NMR (250 MHz) and 13C-NMR (62.90 MHz) spectra for components of essential oils were recorded with a Bruker DPX 250 Avance spectrometer in CDCl3, with TMS as an internal standard.
4.2. Plant Material
Seeds of Carpesium divaricatum Sieb. and Zucc, provided by the Research Center for Medicinal Plant Resources, National Institute of Biomedical Innovation, Tsukuba (Japan), were sown in the end of March 2015, into multipots with garden soil. In the stage of 4–5 mature leaves, the plants were transferred to plastic pots with a substrate composed of garden soil, peat and sand (2:1:1, v/v). Plants were grown in a glasshouse of the Garden of Medicinal Plants, Maj Institute of Pharmacology PAS in Krakow, under controlled conditions (temperatures by day 18–38 °C; by night 12–18 °C), without any chemical treatment. In the third week of May, the plants were divided into two groups. First group was left in the glasshouse for further growth and the second one was transplanted into the open field. Data on cultivation conditions (type of soil, average annual temperature, annual rainfall and agrotechnical procedures applied) are available elsewhere [34]. Aerial parts and roots of the plants were collected in the beginning of flowering period (August/September) and dried under shade at room temperature. Voucher specimen (3/15) was deposited in the collection kept at the Garden of Medicinal Plants, Institute of Pharmacology, Kraków, Poland. The dry plant material was stored no longer than five months.
4.3. Isolation of Essential Oil
Essential oils from aerial (dried leaf, branches, flowers) and underground parts (dried roots) of C. divaricatum were obtained by hydrodistillation using a Clevenger-type apparatus. Each hydrodistillation was conducted for 4 h using 100–300 g of plant material. The yellowish essential oils were dried over anhydrous magnesium sulphate, and stored at 4 °C in the dark, until tested and analyzed.
4.4. Isolation and NMR Analysis of Volatile Components
To isolate the volatiles of interest, the essential oils from aerial parts (i.e., dried leaves with petioles, stems and flowers, 504 mg) and from roots (dried plant material, 973 mg) of the plants grown in the open field were separately flash-chromatographed (FC) on a glass column (500 × 30 mm) filled with silica gel 60 (0.040–0.063 mm, Merck, EM Science, NJ USA), starting the elution with n-hexane and gradually increasing the polarity by addition of diethyl ether. The elution was accelerated by means of pressurized nitrogen (flow rate 100 mL/min). The separation was monitored by TLC and GC-MS. Twenty fractions (1a–20a) of essential oil distilled from the aerial parts of the plant and twenty fractions (1b–20b) of root essential oil were obtained and analyzed by GC-MS-FID. Structures of 11 volatiles from the following fractions were confirmed using NMR spectroscopy (1H and/or 13C; see Supplementary Material): 1a: (42 mg) neryl-isobutyrate (26%); 13a: (22mg) (E)-nerolidol (25%); 15a: (22 mg) τ-cadinol (21%); 17a: (58 mg) nerol (25%); 18a: (48 mg) α-cadinol (23%); 3b: (17 mg) thymol-methyl-ether (33%); 7b: (32 mg) thymyl isobutyrate (57%); 8b: (51 mg) 6-methoxythymyl-isobutyrate (62%); 13b: (13 mg) caryophyllene-oxide (52%); 14b: (36%) 10-isobutyryloxy-8,9-didehydrothymyl-isobutyrate (46%); 15b: (65 mg) 9-isobutyryloxythymyl-isobutyrate (55%); 17b: (53 mg) 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate (63%); 18b: (25 mg) nerol (43%).
4.5. Identification of Essential Oil Constituents
Constituents of the essential oils were identified based on their MS spectra and their comparison with those from mass spectra libraries: NIST 2012, Wiley Registry of Mass Spectral Data 8th edition and MassFinder 4.1, along with the relative retention indices (RI) on DB-1 column (available from MassFinder 4.1) and on Rtx-1MS column found in the literature [35]. Isolated compounds were also identified by the comparison of their 1H-NMR and 13C-NMR spectral data with those of the compounds isolated previously in our laboratory or those from the literature.
5. Conclusions
This was the first study on composition of essential oils from C. divaricatum. Aerial parts of C. divaricatum occurred to be a poor source of volatiles. Essential oil from roots of the plant was rich in thymyl ester derivatives of various structures. As some of the compounds, according to the literature [36], demonstrated moderate antibacterial, antifungal and anti-inflammatory activities, the essential oil from roots of C. divaricatum as well as its components are worth further studies.
Supplementary Materials
The following are available online: Figure S1: Mass spectra and retention indices (RI) together with chemical structures of thymol derivatives detected in C. divaricatum essential oils, Figure S2: Mass spectra and experimental retention indices (RI) of unidentified compounds from C. divaricatum essential oils, Figure S3: Results of NMR analyses of crude fractions (obtained by flash chromatography) from C. divaricatum essential oils.
Author Contributions
Conceptualization, A.S.; methodology, A.W.-B. and A.S.; investigation, A.W.-B., J.M., A.S.; resources, A.W.-B., J.M., A.S.; data curation, A.W.-B. and A.S.; writing—original draft preparation, A.W.-B., J.M., A.S.; writing—review and editing, A.S.; project administration, A.S.
Funding
This research received no external funding.
Acknowledgments
We are greatly indebted to the workers of the Garden of Medicinal Plants, Maj Institute of Pharmacology PAS in Kraków, for cultivation of plants.
Conflicts of Interest
The authors declare no conflict of interest.
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Sample Availability: Samples of the compounds are not available from the authors. |
Figure 1.
Structures of thymol derivatives identified in essential oils from roots of Carpesium divaricatum. 50: thymol-methyl-ether; 54: thymol; 73: 6-methoxythymol-methyl-ether; 84: 8,9-didehydrothymyl-isobutyrate; 85: thymyl-isobutyrate; 111: thymyl-2-methylbutyrate; 130: 6-methoxythymyl-isobutyrate; 131: 6-methoxy-8,9-didehydrothymyl-isobutyrate; 132: 10-isobutyryloxy-8,9-didehydrothymol-methyl-ether; 142: 9-isobutyryloxythymyl-isobutyrate; 143: 10-isobutyryloxy-8,9-didehydrothymyl-isobutyrate; 146: 7-Isobutyryloxythymyl-isobutyrate; 147: 9-(2-methylbutyryloxy)-thymyl-isobutyrate; 148: 10-(2-methylbutyryloxy)-8,9-didehydrothymyl-isobutyrate; 149: 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate; 151: 10-(2-methylbutyryloxy)-8,9-epoxythymyl-isobutyrate; 152: 10-isovaleryloxy-8,9-epoxythymyl-isobutyrate.
Figure 1.
Structures of thymol derivatives identified in essential oils from roots of Carpesium divaricatum. 50: thymol-methyl-ether; 54: thymol; 73: 6-methoxythymol-methyl-ether; 84: 8,9-didehydrothymyl-isobutyrate; 85: thymyl-isobutyrate; 111: thymyl-2-methylbutyrate; 130: 6-methoxythymyl-isobutyrate; 131: 6-methoxy-8,9-didehydrothymyl-isobutyrate; 132: 10-isobutyryloxy-8,9-didehydrothymol-methyl-ether; 142: 9-isobutyryloxythymyl-isobutyrate; 143: 10-isobutyryloxy-8,9-didehydrothymyl-isobutyrate; 146: 7-Isobutyryloxythymyl-isobutyrate; 147: 9-(2-methylbutyryloxy)-thymyl-isobutyrate; 148: 10-(2-methylbutyryloxy)-8,9-didehydrothymyl-isobutyrate; 149: 10-isobutyryloxy-8,9-epoxythymyl-isobutyrate; 151: 10-(2-methylbutyryloxy)-8,9-epoxythymyl-isobutyrate; 152: 10-isovaleryloxy-8,9-epoxythymyl-isobutyrate.
Figure 2.
Gas chromatograms of essential oils from aerial parts and roots of Carpesium divaricatum. The numbering of the compounds corresponds to that in Table 1.
Figure 2.
Gas chromatograms of essential oils from aerial parts and roots of Carpesium divaricatum. The numbering of the compounds corresponds to that in Table 1.
Table 1.
Chemical composition of essential oils from aerial parts and roots of Carpesium divaricatum.
Table 1.
Chemical composition of essential oils from aerial parts and roots of Carpesium divaricatum.
| No | Compound | Amount (%) | RI c exp. | RI d lit. | Identification Method | |||
|---|---|---|---|---|---|---|---|---|
| Aerial Parts | Roots | |||||||
| OF a | G b | OF a | G b | |||||
| 1 | hexanal | - | - | 0.1 | - | 771 | 771 | RI e, MS f |
| 2 | (E)-hex-2-enal | 0.2 | - | - | - | 825 | 832 | RI, MS |
| 3 | hexan-1-ol | 0.1 | - | tr. | - | 852 | 837 | RI, MS |
| 4 | tricyclene | tr. | - | - | - | 917 | 927 | RI, MS |
| 5 | α-thujene | 0.1 | - | - | - | 922 | 932 | RI, MS |
| 6 | α-pinene | 40.2 | 21.8 | 0.1 | 1.8 | 930 | 936 | RI, MS |
| 7 | camphene | 0.3 | - | - | - | 940 | 950 | RI, MS |
| 8 | sabinene | tr. | - | - | - | 944 | 973 | RI, MS |
| 9 | 6-methylhept-5-en-2-one | 0.2 | 0.2 | - | - | 962 | 978 | RI, MS |
| 10 | β-pinene | 0.5 | 0.3 | - | tr. | 966 | 978 | RI, MS |
| 11 | 2-pentylfuran | 0.4 | 0.3 | 0.2 | - | 976 | 981 | RI, MS |
| 12 | trans-2-(pent-2-enyl)furan | 0.1 | 0.1 | - | - | 984 | 984 | RI, MS |
| 13 | α-phellandrene | - | - | tr. | - | 991 | 1002 | RI, MS |
| 14 | δ-car-3-ene | tr. | - | - | - | 1005 | 1010 | RI, MS |
| 15 | m-cymene | 0.2 | tr. | tr. | - | 1006 | 1013 | RI, MS |
| 16 | p-cymene | - | - | tr. | - | 1007 | 1015 | RI, MS |
| 17 | β-phellandrene | - | - | tr. | - | 1014 | 1023 | RI, MS |
| 18 | limonene | 0.2 | tr. | - | 0.1 | 1018 | 1025 | RI, MS |
| 19 | γ-terpinene | 0.1 | 0.2 | - | - | 1047 | 1051 | RI, MS |
| 20 | trans-linalool oxide (furanoid) | tr. | - | tr. | - | 1055 | 1058 | RI, MS |
| 21 | camphen-6-ol | tr. | - | - | - | 1066 | 1082 | RI, MS |
| 22 | terpinolene | tr. | tr. | - | - | 1077 | 1082 | RI, MS |
| 23 | n-nonanal | - | 0.1 | - | - | 1080 | 1076 | RI, MS |
| 24 | linalool | 2.1 | 3.4 | 0.1 | tr. | 1083 | 1086 | RI, MS |
| 25 | 145/89/143/115 M? | 0.1 | - | - | - | 1091 | - | RI, MS |
| 26 | limona ketone | - | - | tr. | - | 1100 | 1105 | RI, MS |
| 27 | α-campholenal | 0.6 | 0.1 | - | - | 1101 | 1105 | RI, MS |
| 28 | cis-p-menth-2-en-1-ol | 0.1 | tr. | 0.1 | 0.1 | 1104 | 1108 | RI, MS |
| 29 | trans-p-menth-2-en-1-ol | - | - | 0.1 | 0.1 | 1119 | 1116 | RI, MS |
| 30 | trans-pinocarveol | 0.7 | 0.2 | - | - | 1120 | 1126 | RI, MS |
| 31 | cis-verbenol | - | tr. | - | - | 1121 | 1132 | RI, MS |
| 32 | trans-verbenol | 0.3 | 0.2 | - | - | 1124 | 1134 | RI, MS |
| 33 | 2-hydroxy-3-methyl- benzaldehyde | - | - | 0.1 | 0.2 | 1126 | 1135 | RI, MS |
| 34 | (E)-non-2-enal | 0.1 | tr. | 0.1 | 0.2 | 1133 | 1136 | RI, MS |
| 35 | nerol oxide | - | - | 0.2 | 1.0 | 1134 | 1137 | RI, MS |
| 36 | pinocarvone | 0.5 | 0.1 | - | - | 1135 | 1137 | RI, MS |
| 37 | p-mentha-1,5-dien-8-ol | 0.1 | 0.2 | - | - | 1143 | 1138 | RI, MS |
| 38 | geijeren | 0.4 | tr. | 4.2 | 3.1 | 1148 | 1139 | RI, MS |
| 39 | terpinen-4-ol | 0.7 | 0.9 | - | - | 1159 | 1164 | RI, MS |
| 40 | myrtenal | - | tr. | - | - | 1165 | 1172 | RI, MS |
| 41 | α-terpineol | 0.8 | 0.7 | 0.1 | 0.1 | 1171 | 1176 | RI, MS |
| 42 | cis-piperitol | - | - | tr. | tr. | 1176 | 1181 | RI, MS |
| 43 | myrtenol | 0.1 | - | - | - | 1177 | 1178 | RI, MS |
| 44 | n-decanal | 0.6 | 1.2 | - | - | 1182 | 1180 | RI, MS |
| 45 | trans-piperitol | - | - | tr. | tr. | 1186 | 1193 | RI, MS |
| 46 | 2-ethenyl-3-methyloanisol | 0.2 | - | 0.7 | 0.9 | 1190 | 1196 | RI, MS |
| 47 | β-cyclocitral | 0.2 | 0.3 | - | - | 1193 | 1195 | RI, MS |
| 48 | trans-carveol | 0.1 | - | - | - | 1195 | 1200 | RI, MS |
| 49 | nerol | 3.7 | 2.1 | 1.4 | 1.2 | 1210 | 1210 | 1H, RI, MS |
| 50 | thymol methyl ether | - | - | 0.4 | 0.1 | 1211 | 1215 | 1H, RI, MS |
| 51 | geraniol | 0.2 | 0.4 | - | - | 1233 | 1235 | RI, MS |
| 52 | α-jonene | 0.1 | - | - | - | 1241 | 1258 | RI, MS |
| 53 | cuminol | tr. | - | 0.3 | 0.3 | 1245 | 1266 | RI, MS |
| 54 | thymol | 0.1 | - | 0.1 | 0.1 | 1258 | 1267 | RI, MS |
| 55 | carvacrol | 0.9 | - | 0.3 | 0.3 | 1264 | 1278 | RI, MS |
| 56 | dihydroedulan II | 0.1 | 0.1 | - | - | 1278 | 1290 | RI, MS |
| 57 | (E,E)-deca-2,4-dienal | 0.1 | - | - | 0.1 | 1286 | 1291 | RI, MS |
| 58 | 4,6-dimethyl-2,3-2H- benzofuran-2-one | - | - | 0.2 | 0.2 | 1317 | - | RI, MS |
| 59 | 7αH-silphiperfol-5-ene | 0.5 | 0.1 | 0.7 | 2.5 | 1323 | 1329 | RI, MS |
| 60 | presilphiperfol-7-ene | 0.2 | - | 0.2 | 0.3 | 1332 | 1342 | RI, MS |
| 61 | 7βH-silphiperfol-5-ene | 0.9 | 0.1 | 1.1 | 3.4 | 1342 | 1352 | RI, MS |
| 62 | α-cubebene | tr. | 0.1 | - | - | 1344 | 1355 | RI, MS |
| 63 | α-longipinene | 0.2 | tr. | 0.3 | 0.4 | 1348 | 1360 | RI, MS |
| 64 | (E)-tridec-6-en-4-yn | 0.2 | 0.1 | - | - | 1363 | - | RI, MS |
| 65 | viburtinal | - | - | 0.5 | 1.2 | 1367 | - | RI, MS |
| 66 | longicyclene | 0.4 | - | 0.3 | 0.4 | 1371 | 1372 | RI, MS |
| 67 | cyclosativene | 0.4 | - | - | - | 1372 | 1378 | RI, MS |
| 68 | α-copaene | - | 0.5 | - | - | 1375 | 1379 | RI, MS |
| 69 | silphiperfol-6-ene | - | - | 0.3 | 0.4 | 1376 | 1379 | RI, MS |
| 70 | modephene | 0.2 | - | 0.3 | 1.0 | 1377 | 1383 | RI, MS |
| 71 | α-isocomene | 0.4 | 0.3 | 0.4 | 1.3 | 1383 | 1389 | RI, MS |
| 72 | 137/121/95/136 M204 | 0.6 | 0.1 | 0.5 | 0.8 | 1391 | - | RI, MS |
| 73 | 6-methoxythymol methyl-ether | 2.1 | 0.5 | 2.7 | 1.4 | 1394 | 1398 | RI, MS |
| 74 | β-isocomene | 0.6 | 0.2 | 0.7 | 2.0 | 1402 | 1411 | RI, MS |
| 75 | α-cedrene | 0.1 | - | tr. | tr. | 1409 | 1418 | RI, MS |
| 76 | α-gurjunene | - | tr. | - | - | 1410 | 1418 | RI, MS |
| 77 | α-santalene | 1.0 | 0.5 | 0.6 | 0.8 | 1413 | 1422 | RI, MS |
| 78 | trans-geranylacetone | 0.3 | 0.3 | - | - | 1423 | 1430 | RI, MS |
| 79 | trans-α-bergamotene | 0.6 | 0.1 | 0.3 | 0.2 | 1428 | 1434 | RI, MS |
| 80 | epi-β-santalene | 1.5 | 0.4 | 0.9 | 0.8 | 1438 | 1446 | RI, MS |
| 81 | α-himachalene | 0.5 | 0.1 | - | - | 1441 | 1450 | RI, MS |
| 82 | aromadendrene | 0.2 | - | 0.3 | 0.4 | 1442 | 1449 | RI, MS |
| 83 | α-humulene | 0.1 | - | tr. | tr. | 1446 | 1455 | RI, MS |
| 84 | 8,9-didehydrothymyl- isobutyrate | 0.9 | 0.2 | 1.6 | 0.8 | 1461 | 1458 | RI, MS |
| 85 | thymyl-isobutyrate | 2.0 | 1.0 | 6.3 | 3.5 | 1467 | 1462 | 1H, RI, MS |
| 86 | β-jonone | 0.9 | 1.5 | - | - | 1468 | 1468 | RI, MS |
| 87 | neryl isobutyrate | 3.2 | 3.9 | 4.1 | 3.9 | 1475 | 1468 | 1H, RI, MS |
| 88 | γ-himachalene | 0.3 | 0.1 | - | - | 1480 | 1479 | RI, MS |
| 89 | 123/93/94/121 M204 | 0.8 | 0.1 | 0.5 | 0.7 | 1484 | - | RI, MS |
| 90 | (3E,6Z)-α-farnesene | 1.8 | 5.5 | - | - | 1487 | 1475 | RI, MS |
| 91 | α-terpinyl isovalerate | - | - | 0.2 | 0.7 | 1489 | 1488 | RI, MS |
| 92 | γ-muurolene | tr. | 0.2 | - | - | 1493 | 1494 | RI, MS |
| 93 | elixene (4-isopropylidene-1-vinyl-o- menth-8-ene) | - | - | 0.2 | 0.2 | 1498 | 1493 | RI, MS |
| 94 | ledene | 1.5 | 2.2 | tr. | 0.2 | 1499 | 1491 | RI, MS |
| 95 | α-muurolene | - | 1.1 | - | - | 1500 | 1496 | RI, MS |
| 96 | (E,E)-α-farnesene | 0.7 | 1.1 | - | - | 1502 | 1498 | RI, MS |
| 97 | β-bisabolene | 1.6 | 0.6 | 0.5 | 0.4 | 1507 | 1503 | RI, MS |
| 98 | γ-cadinene | 1.1 | 3.2 | - | - | 1511 | 1507 | RI, MS |
| 99 | cameronan-7α-ol | - | - | tr. | 0.1 | 1513 | 1513 | RI, MS |
| 100 | α-photosantalol | - | - | 0.1 | 0.2 | 1514 | 1514 | RI, MS |
| 101 | isolongifolan-8-ol | - | - | 0.1 | 0.5 | 1517 | 1515 | RI, MS |
| 102 | cis/trans-calamenene | 0.2 | 0.4 | 0.2 | 0.3 | 1526 | 1517 | RI, MS |
| 103 | δ-cadinene | 1.4 | 5.3 | - | - | 1520 | 1520 | RI, MS |
| 104 | β-cadinene | 0.1 | 0.3 | - | - | 1523 | 1526 | RI, MS |
| 105 | 9-methoxycalamenene | 0.1 | - | - | - | 1524 | - | RI, MS |
| 106 | 147/162/121/177 M206 | - | - | tr. | 0.1 | 1531 | - | RI, MS |
| 107 | 121/163/93/134 M218 | - | - | 0.2 | 0.1 | 1534 | - | RI, MS |
| 108 | α-cadinene | 0.3 | 0.5 | - | - | 1535 | 1534 | RI, MS |
| 109 | (E)-α-bisabolene | 0.1 | 0.2 | 0.1 | 0.7 | 1536 | 1530 | RI, MS |
| 110 | (E)-nerolidol | 2.2 | 8.6 | 0.6 | 0.6 | 1543 | 1553 | 1H, RI, MS |
| 111 | thymyl-2-methylbutyrate | 0.1 | - | 0.2 | 0.2 | 1546 | - | RI, MS |
| 112 | neryl-α-methylbutyrate | 1.7 | 1.6 | 3.6 | 3.4 | 1551 | 1565 | RI, MS |
| 113 | neryl isovalerate | 1.6 | 1.3 | 2.3 | 1.8 | 1557 | 1579 | RI, MS |
| 114 | caryophyllene oxide | 0.4 | 0.4 | 1.1 | 2.1 | 1565 | 1578 | 1H, RI, MS |
| 115 | viridiflorol | 0.5 | 1.4 | - | - | 1577 | 1592 | RI, MS |
| 116 | isoaromadendreneepoxide | 0.3 | 0.1 | - | - | 1584 | 1590 | RI, MS |
| 117 | ledol | 0.3 | 0.5 | - | - | 1588 | 1600 | RI, MS |
| 118 | humulene II epoxide | - | - | 0.4 | 1.1 | 1595 | 1602 | RI, MS |
| 119 | 1,10-di-epi-cubenol | 0.1 | 0.2 | - | - | 1597 | 1615 | RI, MS |
| 120 | 135/146/159/71 M218 | - | - | 0.2 | 0.3 | 1602 | - | RI, MS |
| 121 | muurola-4,10(14)-dien-1β-ol | 0.2 | 0.2 | - | - | 1605 | 1620 | RI, MS |
| 122 | gossonorol | - | - | 0.1 | 0.1 | 1613 | 1626 | RI, MS |
| 123 | 1-epi-cubenol | 0.2 | 0.5 | - | - | 1614 | 1623 | RI, MS |
| 124 | α-acorenol | tr. | - | 0.4 | 0.5 | 1620 | 1623 | RI, MS |
| 125 | τ-cadinol | 1.4 | 4.1 | - | - | 1625 | 1633 | 1H, RI, MS |
| 126 | τ-muurolol | 0.3 | 0.4 | - | - | 1628 | 1633 | RI, MS |
| 127 | β-eudesmol | 0.6 | 0.2 | 3.4 | 3.8 | 1631 | 1641 | RI, MS |
| 128 | α-cadinol | 1.3 | 3.8 | 0.4 | 0.3 | 1638 | 1643 | 1H, RI, MS |
| 129 | 5β,7βH,10α-eudesm-11-en- 1α-ol | - | - | 0.3 | - | 1653 | - | RI, MS |
| 130 | 6-methoxythymyl isobutyrate | 0.9 | 0.7 | 3.8 | 4.9 | 1657 | 1658 | 1H,13C, RI, MS |
| 131 | 6-methoxy-8,9-didehydrothymyl isobutyrate | tr. | - | 0.4 | 0.2 | 1665 | 1676 | RI, MS |
| 132 | 10-isobutyryloxy-8,9- didehydrothymol-methyl-ether | - | - | 0.4 | 0.3 | 1666 | 1684 | 1H,13C, RI, MS |
| 133 | α-bisabolol | 0.1 | 0.4 | 0.3 | 1.3 | 1668 | 1683 | RI, MS |
| 134 | 145/162/71/115 M232 | - | - | 0.3 | 0.5 | 1681 | - | RI, MS |
| 135 | aromadendrene oxide | 0.1 | 0.1 | - | - | 1702 | 1672 | RI, MS |
| 136 | 135/148/133/91 M236 | - | - | 0.1 | 0.1 | 1725 | - | RI, MS |
| 137 | 135/164/71/91 M234 | - | - | 0.2 | 0.1 | 1733 | - | RI, MS |
| 138 | fenantrene (artifact) | 0.1 | 0.3 | - | - | 1741 | 1744 | RI, MS |
| 139 | diisobutylphtalate (artifact) | 0.9 | 2.5 | 0.3 | 0.6 | 1817 | 1819 | RI, MS |
| 140 | hexahydrofarnesylacetone | 0.2 | 0.8 | - | - | 1820 | 1830 | RI, MS |
| 141 | alantolactone | 0.1 | - | 0.2 | tr. | 1854 | 1878 | RI, MS |
| 142 | 9-isobutyryloxythymyl- isobutyrate | 0.2 | 0.8 | 5.6 | 5.7 | 1879 | 1891 | 1H,13C, RI, MS |
| 143 | 10-isobutyryloxy-8,9- didehydrothymyl-isobutyrate | - | - | 3.0 | 3.1 | 1882 | 1891 | RI, MS |
| 144 | (5E,9E)-farnesylacetone | 0.1 | 0.2 | - | - | 1889 | 1895 | RI, MS |
| 145 | dibutylphtalate (artifact) | 0.2 | 1.8 | - | - | 1906 | 1909 | RI, MS |
| 146 | 7-isobutyryloxythymyl- isobutyrate | - | - | 0.6 | 0.7 | 1914 | 1924 | RI, MS |
| 147 | 9-(2-methylbutyryloxy)thymyl-isobutyrate | - | - | 1.0 | 1.4 | 1964 | 1970 | RI, MS |
| 148 | 10-(2-methylbutyryloxy)-8,9- didehydrothymyl-isobutyrate | 0.1 | 0.4 | 0.3 | 0.4 | 1967 | 1970 | RI, MS |
| 149 | 10-isobutyryloxy-8,9- epoxythymyl-isobutyrate | 0.2 | 0.6 | 29.2 | 18.1 | 2002 | 2036 | 1H,13C,RI,MS |
| 150 | 71/177/150/135 M290 | - | - | 0.9 | 0.5 | 2048 | - | RI, MS |
| 151 | 10-(2-methylbutyryloxy)-8,9- epoxythymyl-isobutyrate | - | - | 4.4 | 3.6 | 2077 | 2056 | RI, MS |
| 152 | 10-isovaleroxy-8,9- epoxythymyl-isobutyrate | - | - | 0.3 | 0.1 | 2097 | 2122 | RI, MS |
| 153 | fitol | 0.3 | 1.7 | - | - | 2098 | - | RI, MS |
| 154 | 57/177/71/85 M304 | - | - | 0.1 | 0.1 | 2149 | - | RI, MS |
| 155 | tricosane | 0.1 | 0.2 | - | - | 2286 | 2300 | RI, MS |
| 156 | tetracosane | 0.1 | - | - | - | 2386 | 2400 | RI, MS |
| 157 | pentacosane | 0.6 | 0.3 | - | - | 2489 | 2500 | RI, MS |
| 158 | hexacosane | tr. | - | - | - | 2589 | 2600 | RI, MS |
| 159 | heptacosane | 0.2 | 0.1 | - | - | 2685 | 2700 | RI, MS |
| Sum of Identified | 96.7 | 97.5 | 94.3 | 91.7 | ||||
| Yield of Essential Oil (%) | 0.016 | 0.014 | 0.150 | 0.059 | ||||
a Essential oils isolated from aerial parts and roots of Carpesium divaricatum cultivated in the open field. b Essential oils isolated from aerial parts and roots of Carpesium divaricatum cultivated in a greenhouse. c Experimental retention index measured on non-polar column. d Literature retention index from non-polar column. e Identification based on retention index. f Identification based on mass spectrum. Tr.—<0.05%.
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Wajs-Bonikowska, A.; Malarz, J.; Stojakowska, A. Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland. Molecules 2019, 24, 4418. https://doi.org/10.3390/molecules24234418
AMA Style
Wajs-Bonikowska A, Malarz J, Stojakowska A. Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland. Molecules. 2019; 24(23):4418. https://doi.org/10.3390/molecules24234418
Chicago/Turabian StyleWajs-Bonikowska, Anna, Janusz Malarz, and Anna Stojakowska. 2019. "Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland" Molecules 24, no. 23: 4418. https://doi.org/10.3390/molecules24234418
APA StyleWajs-Bonikowska, A., Malarz, J., & Stojakowska, A. (2019). Composition of Essential Oils from Roots and Aerial Parts of Carpesium divaricatum, a Traditional Herbal Medicine and Wild Edible Plant from South-East Asia, Grown in Poland. Molecules, 24(23), 4418. https://doi.org/10.3390/molecules24234418
