Research Article
Received: 2022-12-20 | Revised:2023-02-10 | Accepted: 2023-02-16 | Published: 2023-02-23
Pages: 60-64
DOI: https://doi.org/10.58985/jeopc.2023.v01i02.09
Abstract
The essential oil from the Vernonia gracilis Kunth (Asteraceae) leaves collected in San Juan de Lagunillas, Venezuela was obtained by hydrodistillation and its composition was determined by GC/MS. The yield of the essential oil was 0.001 % (v/w), calculated on a dry weight basis. Twenty-four compounds were identified, representing 93.19 % of the oil. The most abundant components were β-caryophyllene (23.15 %), germacrene-D (18.68 %), bicyclogermacrene (18.31 %), α-humulene (6.38 %), caryophyllene epoxide (4.84 %) and spathulenol (4.53 %).
Keywords
Vernonia;
Vernonia gracilis, essential oil, β-caryophy-llene, germacrene D,
bicy-clegremacrene.
1. Introduction
Vernonia (family Asteraceae, tribe Vernonieae) is a genus of about 1300 species, it’s widely distributed in tropical and sub-tropical areas, especially in South America, Asia and Africa [1]. Several Vernonia species have been used in traditional medicine to treat reproductive problems, including urinary tract infections, diabetes mellitus, bacterial infections and malaria [2-6]. Various studies have reported antioxidant, anthelminthic, antimicrobial, anti-diabetes, anti-inflammatory, antitumor, analgesic, anti-plasmodial, anticancer and neuroprotective activities [7-11].
Numerous phytochemical studies of the genus Vernonia have revealed the presence of diterpenes, triterpenes, steroids, and the most frequently isolated chemical constituents are flavonoids and sesquiterpene lactones, which have been used as taxonomic markers [12-16]. Despite this extensive investigation, little is known about the composition of the genus Vernonia essential oils.
Vernonia gracilis Kunth is a synonym for Lepidaploa gracilis [17,18]. Literature surveys reveal that no phytochemical investigations have been previously conducted on the essential oil of V. gracilis, the present study was undertaken to obtain knowledge of their chemical composition.
2. Materials and methods
2.1 Plant material
Leaves of V.
gracilis were collected in May 2016 at San Juan de Lagunillas, Mérida State,
Venezuela. A voucher specimen (LCGM01) has been deposited at the MERF Herbarium
(Herbarium of the Faculty of Pharmacy and Bioanalysis in Mérida, Venezuela).
The botanical identification was made by Dr. Pablo Meléndez.
2.2 Extraction and analysis of the essential oil
Fresh leaves (1000 g) were cut into small pieces and submitted to hydrodistillation for 3 hours using a Clevenger-type apparatus. A volume of 0.1 mL of essential oil was obtained (0.001 %, v/w). The composition of the essential oil was determined by comparison of the mass spectrum of each component with Wiley GC/MS library data and also from RI data.
2.3 Gas chromatography – mass spectrometry
Gas chromatography – mass spectrometry (GC-MS) analyses were conducted on a Model 5973 Hewlett-Packard GC-MS system fitted with a HP- 5MS fused silica column (30 m x 0.25 mm i.d., film thickness 0.25 µm, Hewlett-Packard). The oven temperature program was the same as the one used for the HP-5 column for GC analysis; the transfer line temperature was programmed from 150 °C to 180 °C; source temperature, 230 °C; quadrupole temperature 150 °C; carrier gas, helium adjusted to a linear velocity of 34 cm/s; ionization energy, 70 eV; scan range, 40 to 500 amu; 3.9 scans/s. A sample of a 2 % solution of the essential oil (1.0 µL) was injected using a Hewlett-Packard ALS injector with a split ratio of 50:1. The identity of the oil components was established from their GC retention indices, by comparing their MS and those of standard components available in the laboratory, and through library search (Nist 05 and Wiley MS Data Library, 6th edn) [19, 20].
3. Results and discussion
The hydrodistillation from the leaves of V. gracilis produced 0.1 mL yellow oil with a yield of 0.001 %. The chemical composition of the oil was investigated using GC-MS technique. Twenty-four components were identified in the leaves’ oil, which represent 93.19 % of the total oil. These compounds and their retention indices (RI) and relative percentage concentrations are listed in Table 1 and Fig. 1, according to the elution order on HP-5 column.
Table 1. Percentage composition of the essential oil from leaves of Vernonia gracilis Kunth.
No. | Compounds | Composition of essential oil (%) | aRI | bRI |
1 | β-Pinene | 0.46 | 965 | 979 |
2 | Limonene | 0.16 | 1032 | 1029 |
3 | Cis-3-hexenyl 3-methylbutanoato | 0.19 | 1231 | 1235 |
4 | β-Copaene | 2.18 | 1382 | 1387 |
5 | β- Bourbonene | 0.74 | 1385 | 1388 |
6 | β-Elemene | 0.98 | 1396 | 1390 |
7 | β -Gurjunene | 0.35 | 1428 | 1433 |
8 | β-Caryophyllene | 23.15 | 1440 | 1433 |
9 | Epi-Bicyclosesquiphellandrene | 0.34 | 1448 | 1463 |
10 | α-Humulene | 6.38 | 1457 | 1465 |
11 | Alloaromadendrene | 2.10 | 1471 | 1460 |
12 | α-Amorphene | 0.75 | 1482 | 1484 |
13 | Germacrene-D | 18.68 | 1492 | 1485 |
14 | Bicyclogermacrene | 18.31 | 1502 | 1500 |
15 | Germacreno A | 0.77 | 1503 | 1509 |
16 | γ-Cadinene | 0.60 | 1513 | 1528 |
17 | d-Cadineno | 1.56 | 1526 | 1530 |
18 | Spathulenol | 4.53 | 1575 | 1578 |
19 | Caryophyllene epoxide | 4.84 | 1603 | 1588 |
20 | Viridiflorol | 1.45 | 1611 | 1610 |
21 | Humulene epoxide | 0.63 | 1609 | 1608 |
22 | Isospathulenol | 1.27 | 1624 | 1626 |
23 | α-Cadinol | 1.68 | 1661 | 1672 |
24 | T-Muurolol | 1.09 | 1658 | 1659 |
| Total Identified | 93.19 |
|
|
aRI: Retention index this work. bRI: Theoretical Retention index. | ||||
Figure 1. GC chromatogram (HP-5 column) and representative compounds of
leaves of Vernonia gracilis Kunth.
The identified products may be divided into four different groups: monoterpenes (0.62 %), oxygenated monoterpenes (0.19 %), sesquiterpenes (76.89 %) and oxygenated sesquiterpenes (15.49 %). The main components of the leaves’ oil were β-caryophyllene (23.15 %), germacrene-D (18.68 %), bicyclogermacrene (18.31 %), α-humulene (6.38 %), caryophyllene epoxide (4.84 %) and spathulenol (4.53 %). This is the first report on the volatile compounds of V. gracilis, the present data could not be compared with other analysis of the same species.
There are several reports on the oil composition of the plants of the genus Vernonia described in other parts of the world (Vietnam, Brazil, India and Nigeria) [21]. Most of them are characterized by the presence of monoterpenoids and sesquiterpenoids. The preliminary chemical analysis of the essential oils of Vernonia has been performed earlier the major components were β-caryophyllene (28.50 %), caryophyllene oxide (16.60 %), α-copaene (9.00 %) and α-humulene (7.10 %) from the leaves of V. patula [21] and the essential oil was obtained from V. chalybaea showing it was rich in β-caryophyllene (39.06 %) and bicyclogermacrene (19.69 %) [22]. The major components found in the essential oil from aerial parts of V. scorpiodes were β -caryophyllene (30.60 %), germacrene D (27.30 %), and bicyclogermacrene (8.50 %) [23]. On the other hand, the major components of the essential oils from the aerial parts of V. amygdalina and from the roots of V. cinerea were α-muurolol (45.70 %) and α-muurolene (30.70 %), respectively [24, 25]. The principal components of the essential oil analysis of V. crotonoides were α-cadinol (14.10 %), spathulenol (9.80 %), caryophyllene oxide (5.90 %), and epi-α-cadinol (5.30 %) [26].
The major constituents reported in the essential oils from different organs of V. condensata were the leaf oil β-caryophyllene (18.35 %), γ-muurolene (16.41 %) and α-humulene (6.03). Linalol (12.13 %), 10-epi-italicene ether (8.88 %), myrcene (7.68 %), and 2-δ-carene (6.86 %) were in the stem oil. The monoterpenes 1,8-cineole (11.03 %), thymol (7.68 %) and linalool (6.30 %) were the major constituents reported in the flower oil [27].
It is well known that sesquiterpenes compounds, as identified in the present study, predominate in the essential oils of the genus Vernonia. These differences are mainly due to variations in the ecological conditions, genetic and environmental factors, such as temperature, moisture, the soil, the harvest period, geographical position, seasonal variations and the vegetative cycle are important [28, 29].
4. Conclusions
In the current investigation, the chemical composition of essential oil of fresh leaves of Vernonia gracilis (Asteraceae) collected in Mérida, Venezuela was evaluated. The essential oil is dominated by the presence of sesquiterpenes (76.89 %) and oxygenated sesquiterpenes (15.49 %). The main components were β-caryophyllene (23.15 %), germacrene-D (18.68 %) and bicyclogermacrene (18.31 %). To our knowledge, this is the first time that the chemical composition of the essential oil of the leaves V. gracilis of has been reported and this compounds may also aid in future chemotaxonomic research of this species.
Authors’ contributions
Conceptualization, L.R.F.; Methodology, L.R.F.; Software, L.R.F.; Validation, A.P.C., Formal analysis, A.P.C.; Y.O.D.; Investigation, A.P.C., R.A.Z., Y.O.D.; Resources, A.P.C., R.A.Z., Y.O.D; Data curation, R.A.Z.; Writing – original draft preparation, A.P.C., Y.O.D.; Writing – review & editing, A.P.C., R.A.Z., Y.O.D.
Acknowledgements
All authors are grateful to the Research Institute “Dr. Alfredo Nicolás Usubillaga del Hierro”, Faculty of Pharmacy and Bioanalysis, University of Los Andes, Mérida 5101, Venezuela.
Funding
This research received no specific grant from any funding agency.
Conflicts of interest
The authors declare no conflict of interest.
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Abstract
The essential oil from the Vernonia gracilis Kunth (Asteraceae) leaves collected in San Juan de Lagunillas, Venezuela was obtained by hydrodistillation and its composition was determined by GC/MS. The yield of the essential oil was 0.001 % (v/w), calculated on a dry weight basis. Twenty-four compounds were identified, representing 93.19 % of the oil. The most abundant components were β-caryophyllene (23.15 %), germacrene-D (18.68 %), bicyclogermacrene (18.31 %), α-humulene (6.38 %), caryophyllene epoxide (4.84 %) and spathulenol (4.53 %).
Abstract Keywords
Vernonia;
Vernonia gracilis, essential oil, β-caryophy-llene, germacrene D,
bicy-clegremacrene.
This work is licensed under the
Creative Commons Attribution
4.0
License (CC BY-NC 4.0).
Editor-in-Chief
This work is licensed under the
Creative Commons Attribution 4.0
License.(CC BY-NC 4.0).