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Volatile Constituents of Emilia sonchifolia from India

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  • ICMR-National Institute of Traditional Medicine (Formerly Regional Medical Research Centre)

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The volatile constituents were isolated by hydro-distillation of the aerial parts of Emilia sonchifolia (L.) DC. (Asteraceae). The constituents were analyzed for the first time by gas chromatography equipped with flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Forty-three compounds were identified, representing 96.3% of the total oil. The major constituents were γ-muurolene (32.1%) and β-caryophyllene (22.7%). The other minor constituents were (E)-β-ocimene (4.0%), α-muurolene (3.9%), δ-cadinene (3.7%) and epi-α-cadinol (3.7%). The oil was found to be rich in sesquiterpene hydrocarbon (67.6%) type constituents.
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Volume 13. Issue 10. Pages 1235-1418. 2018
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The School of Pharmacy & Biomedical Sciences,
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Volatile Constituents of Emilia sonchifolia from India
Rajesh K. Joshi
Department of Phytochemistry, ICMR-National Institute of Traditional Medicine, Nehru Nagar, Belagavi,
Karnataka-590 010, India
joshirk_natprod@yahoo.com
Received: January 11th, 2016; Accepted: August 28th, 2018
The volatile constituents were isolated by hydro-distillation of the aerial parts of Emilia sonchifolia (L.) DC. (Asteraceae). The constituents were analyzed
for the first time by gas chromatography equipped with flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry
(GC/MS). Forty-three compounds were identified, representing 96.3% of the total oil. The major constituents were γ-muurolene (32.1%) and β-caryophyllene
(22.7%). The other minor constituents were (E)-β-ocimene (4.0%), α-muurolene (3.9%), δ-cadinene (3.7%) and epi-α-cadinol (3.7%). The oil was found to be
rich in sesquiterpene hydrocarbon (67.6%) type constituents.
Keywords: Emilia sonchifolia, Asteraceae, γ-Muurolene, β-Caryophyllene, Volatile constituents, GC/MS.
Emilia sonchifolia (L.) DC. (Asteraceae) is an annual sub-erect herb
grows up to 60 cm tall [1] and widely distributed throughout India
as a weed in the cultivated fields and wasteland area [2]. In
traditional medicine, the leaves juice of E. sonchifolia is used for
the treatment of eye inflammations, night blindness, cuts and
wounds, sore ears, infantile tympanites and bowel complaints [3a].
In Chinese traditional medicine, the leaves of this plant is used
against for fever and dysentery [3b]. In African folk medicine, the
tea made from the leaves of E. sonchifolia is used for the treatment
of dysentery [3c]. The flower heads are chewed and kept in the
mouth for about 10 minutes to prevent tooth decay [3d]. This plant
has astringent, depurative, diuretic, expectorant, febrifuge and
sudorific properties [3d]. Diverse biological activities Viz.,
cytotoxic, antitumor [4a], anti-inflammatory, analgesic [4b],
antinociceptive [4c], modulatory effects [4d], antiviral [4e],
erythropoietic and hepatoprotective [4f] of the E. sonchifolia have
been reported. The non-volatile compounds rhamnetin,
isorhamnetin, quercetin, luteolin, tricin-7-O-β-D-glucopyranoside,
8-(2"-pyrrolidinone-5"-yl)-quercetin, 5,2',6'-trihydroxy-7,8-
dimethoxyflavone-2'-O-β-D-glucopyranoside, succinic acid, fumaric
acid, p-hydroxybenzoic acid, 4-hydroxy isophthalic acid, 3,4-
dihydroxycinnamic acid, esculetin, isowedelolactone and uracil
have been identified from ethanolic extract of E. sonchifolia [5a].
The compounds pyrrolizidine alkaloids viz., senkirkine, doronine
[5b], senecionine, seneciphylline, integerrimine, senkirkine,
otosenine, neosenkirkine, petasitenine, acetylsenkirkine, acetyl
petasitenine, desacetyldoronine, and doronine have been identified
from E. sonchifolia, which exhibited hepatotoxic activity [5c]. The
aim of this study was to explore and generate terpenoid profile of E.
sonchifolia. To the best of author's knowledge, this is the first report
on the volatile constituents of E. sonchifolia.
Forty-three compounds were identified according to their mass
spectra and their relative retention indices determined in a non-polar
stationary phase capillary column, comprising 96.3% of the total oil
constituents. The identified compounds are listed in Table 1 in
elution order from the BP-1 column, along with the percentage
composition of each component and its retention index. The major
compounds were identified as γ-muurolene (32.1%) and β-
caryophyllene (22.7%). The other minor constituents were
(E)-β- ocimene (4.0%), α-muurolene (3.9%), δ-cadinene (3.7%) and
Table 1: Volatile constituents of E. sonchifolia.
Compound RI % Identification
α-Pinene 918 2.6 RI, MS, CI
Camphene 928 0.2 RI, MS, CI
Sabinene 946 t RI, MS, CI
β-Pinene 949 1.2 RI, MS
Limonene 996 0.3 RI, MS
(Z)-β-Ocimene 1003 1.8 RI, MS
(E)-β-Ocimene 1014 4.0 RI, MS
Terpinolene 1056 0.5 RI, MS, CI
Terpin-4-ol 1149 0.4 RI, MS, CI
α-Terpineol 1162 0.3 RI, MS, CI
Methyl chavicol 1166 t RI, MS, CI
β-Cyclocitral 1190 0.3 RI, MS
cis-Pulegol 1193 0.4 RI, MS
(E)-Anethole 1268 t RI, MS, CI
(1E)-1Ethylidene-1H-indene 1275 t RI, MS
Isobornyl acetate 1280 t RI, MS
Thymol 1284 t RI, MS, CI
δ-Elemene 1358 1.4 RI, MS
(Z)-β-Damascenone 1392 1.0 RI, MS
Cyclosativene 1394 0.4 RI, MS
α-Copaene 1404 0.3 RI, MS
β-Cubebene 1419 0.3 RI, MS
β-Elemene 1421 1.3 RI, MS
β-Caryophyllene 1454 22.7 RI, MS, CI
β-Gurjunene 1463 0.4 RI, MS
γ-Elemene 1469 0.2 RI, MS
Demethoxy-ageratochromene 1475 3.5 RI, MS
α-Humulene 1490 0.2 RI, MS
(E)-β-Farnesene 1499 0.3 RI, MS
γ-Muurolene 1524 32.1 RI, MS, CI
epi-Cubebol 1536 0.7 RI, MS, CI
α-Muurolene 1544 3.9 RI, MS, CI
α-Bulnesene 1547 0.3 RI, MS
(E,E)-α-Farnesene 1556 0.1 RI, MS
δ-Cadinene 1569 3.7 RI, MS
Caryophyllene oxide 1625 2.8 RI, MS, CI
1, 10-di-epi-Cubenol 1666 0.3 RI, MS
10 epi-γ-Eudesmol 1668 0.1 RI, MS
epi-α-Cadinol 1678 3.7 RI, MS
α-Muurolol 1702 2.1 RI, MS
(E)-Amyl cinnamaldehyde 1789 0.9 RI, MS
7,14-Anhydro-amorpha-4,9-diene 1808 0.5 RI, MS
Hexadecanoic acid 2026 1.1 RI, MS
Monoterpene hydrocarbons 10.6
Oxygenated monoterpenes 1.4
Sesquiterpene hydrocarbons 67.6
Oxygenated sesquiterpenes 10.2
Others 6.5
Total identified 96.3
RI=Retention index relative to C8-C25n-alkanes on BP-1column, MS=NIST and Wiley
library and the literature, t=trace (<0.1%), CI=Co-injection of commercial samples.
epi-α-cadinol (3.7%). The oil was found to be rich in sesquiterpene
hydrocarbons (67.6%), followed by monoterpene hydrocarbons
NPC Natural Product Communications 2018
Vol. 13
No. 10
1355 - 1356
1356 Natural Product Communications Vol. 13 (10) 2018 Joshi
(10.6%), oxygenated sesquiterpenes (10.2%), others (includes
phenyl derivatives and long-chain hydrocarbons compounds)
(6.5%) and oxygenated monoterpenes (1.4%).
According to the literature, the presence of γ-muurolene in essential
oils showed anticancer [6a] and antimicrobial activity [6b]. Also, β-
caryophyllene has anticancer activity [7a], local anesthetic [7b] and
peripheral effects [7c]. Hence, E. sonchifolia could be a good
source of γ-muurolene and β-caryophyllene, which are the main
constituents of the oil. Further studies are required to investigate
biological activities of the essential oil of this plant.
Experimental
Plant material: The aerial parts of E. sonchifolia were collected in
September 2014 from Belagavi (N 15.88668; E 74.52353),
Karnataka, India at an elevation of ~800 m. The plant was identified
by at ICMR-National Institute of Traditional Medicine (NITM),
Belagavi where a voucher specimen (RMRC-1269) has been
deposited.
Isolation of volatile constituents: The fresh plant material (500 g)
was hydro-distilled using a Clevenger type apparatus for 3h. The oil
was dried over anhydrous Na2SO4 and the solvent was removed
under vacuum in a vial and stored at -4°C until analysis the oil yield
was 0.05%, v/w.
Analysis of volatile constituents: The volatile constituents were
analyzed by using a Varian 450 (TG-5, 30 m × 0.25 mm i.d., 0.25
μm film thickness) Gas Chromatograph under the experimental
conditions reported earlier [8a]. The oven temperature was
programmed from 60-220°C at 3°C/min, using nitrogen as carrier
gas. The injector temperature was 230°C and the detector (FID)
temperature 240°C. GC-MS utilized a Thermo Scientific Trace
Ultra GC interfaced with a Thermo Scientific ITQ 1100 mass
spectrometer fitted with a BP-1 (SGE Analytical Science) fused
silica capillary column (30 m × 0.25 mm; 0.25 μm film thickness).
The oven temperature range was 60-220°C at 3°C /min using
helium as carrier gas at 1.0 mL/min. The injector temperature was
230°C, and the injection volume 0.1 μL in n-hexane, with a split
ratio of 1:50. MS were taken at 70 eV with a mass range of m/z 40-
450. The MS parameters were those reported earlier [8b].
Identification of the components: Identification of constituents
were made on the basis of retention index (RI, determined with
reference to a homologous series of n-alkanes C8-C25, under
identical experimental conditions), MS library search (NIST 08 MS
Library (Version 2.0 f; Thermo Fisher Scientific Austria) and
WILEY MS 9th Edition (Thermo Fisher Scientific Austria), and by
comparing with MS literature data [9] and co-injection of
commercial samples purchased from Sigma-Aldrich, India. The
relative amounts of individual components were calculated based on
the GC peak area (FID response) without using a correction factor.
Acknowledgments - The author is grateful to the Indian Council of
Medical Research (ICMR), New Delhi, India for providing the
necessary facilities, and thankful to Mr. Mahesh B. Wagharwadi,
Multi Tasking Staff (MTS), Department of Phytochemistry, ICMR-
NITM, Belagavi for collection of plant, processing and extraction of
the oil.
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Natural Product Communications
2018
Volume 13, Number 10
Contents
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... The essential oil was dissolved in a 1% solution of equal-ratio nhexane:dichloromethane and the composition of C zeylanicum oil was analysed with a Varian 450 gas chromatograph (GC) fitted with a fused silica capillary BP-1 column (30 m × 0.25 mm inner diameter, 0.25-μm film thickness; SGE Analytical Science, now Trajan, Chester, UK), using previously described experimental settings. [25][26][27] The programmed oven temperature was 60-220 °C at 3 °C min −1 , with N 2 as the carrier gas. The injector temperature was fixed at 230 °C, whereas the flame ionization detector (FID) temperature was set at 240 °C. ...
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The hydrodistilled essential oil obtained from leaves of Cinnamomum zeylanicum Blume (Lauraceae) collected throughout the year was examined using gas chromatography fitted with flame ionization detector (GC‐FID) and gas chromatography connected with mass spectrometry (GC‐MS). The variation in essential oil yield was found to be in the range of 1.1–1.4% (w/w). Between 28 and 40 components, representing 97.92 ± 0.15% of the total oil, were identified. The chief compound was identified as eugenol, varying from 60.24 ± 0.42 to 89.82 ± 0.55%. The other constituents were eugenyl acetate (ranging from 0.10 ± 0.01 to 19.87 ± 0.52%), α‐phellandrene (ranging from 0.76 ± 0.04 to 6.23 ± 0.13%), benzyl benzoate (ranging from 0.91 ± 0.05 to 5.03 ± 0.20%), linalool (ranging from 1.11 ± 0.04 to 3.25 ± 0.08%), and β‐caryophyllene (ranging from 0.50 ± 0.01 to 2.92 ± 0.10%). The essential oils collected throughout the year were found to be rich in phenyl derivative constituents (88.49 ± 0.97%). The biosynthesis and conversion of eugenyl acetate to eugenol appeared as the leaves of C. zeylanicum reached maturity. It was noticed that when leaves were immature, in July and August during the full rainy season, the content of eugenyl acetate was found to be highest, as compared with mature leaves in the other months, with the exception of February (flowering season). Variation between eugenol and eugenyl acetate levels were observed in the essential oil of Cinnamomum zeylanicum leaves. When leaves were immature, in July and August during the full rainy season, the content of eugenyl acetate was found to be highest, as compared with mature leaves in the other months, with the exception of February (flowering season). The period between March and June, when the level of eugenol is higher than 85%, useful in the food industry and other medicinal purposes..
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Chemical composition and antimicrobial activity of Teucrium capitatum L. subsp. lusitanicum essential oil was investigated for the first time in the present study. Qualitative and quantitative analyses of the chemical composition by gas chromatography and mass spectrometry (GC–FID and GC–MS) revealed the presence of 60 compounds representing 97.6% of the whole constituents. The main compounds were germacrene D (47.1%), spathulenol (5.8%), α-selinene (5.3%), germacrene A (2.9%), δ cadinene (2.8%) and cubenol (2.7%). In vitro, the antimicrobial activity was investigated against five bacterial strains along with the yeast Candida albicans using broth microdilution assay. T. capitatum subsp. lusitanicum essential oil showed significant activity against the gram-positive bacteria Staphylococcus aureus (MIC = MBC = 78 µg mL−1), Bacillus subtilis (MIC = MBC = 156 µg mL−1) and the yeast C. albicans (MIC =MFC = 156 µg mL−1). The great potential of antimicrobial effects is most likely due to the very high percentage of sesquiterpene hydrocarbons particularly to germacrene D, for which the antimicrobial properties have been previously reported.
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E)-β-caryophyllene (BCP) is a natural sesquiterpene hydrocarbon present in hundreds of plant species. BCP possesses several important pharmacological activities, ranging from pain treatment to neurological and metabolic disorders. These are mainly due to its ability to interact with the cannabinoid receptor 2 (CB2) and the complete lack of interaction with the brain CB1. A systematic analysis of plant species with essential oils containing a BCP percentage > 10% provided almost 300 entries with species belonging to 51 families. The essential oils were found to be extracted from 13 plant parts and samples originated from 56 countries worldwide. Statistical analyses included the evaluation of variability in BCP% and yield% as well as the statistical linkage between families, plant parts and countries of origin by cluster analysis. Identified species were also grouped according to their presence in the Belfrit list. The survey evidences the importance of essential oil yield evaluation in support of the chemical analysis. The results provide a comprehensive picture of the species with the highest BCP and yield percentages.
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This study was carried out to compare for the first time, the chemical composition and antimicrobial activities of essential oils from two Ballota species growing wild in different regions of Tunisia. The volatile oils obtained by hydro-distillation of Ballota bullata Pomel and Ballota nigra L. subsp. uncinata (Fiori & Beg.) Patzak were analyzed by gas chromatography (GC) and gas chromatography mass spec- � trometry (GC/MS) to investigate the variations in chemical profiles. The results showed a significant difference in terms of essential oil yields and characteristic aroma. Valerianol (18.3%), a-muurolol (7.9%) and spathulenol (7.1%) were identified as the major odorants in B. bullata, while B. nigra subsp. uncinata oil was mainly composed of hexadecanoic acid (31.8%) and linoleic acid (17.9%). In addition, oxygenated sesquiterpenes were found to be the principal constituents of B. bullata essential oil (42.1%), whereas long chain oxygenated hydrocarbons form the main class in B. nigra (49.7%). Moreover, the antimicrobial activities were tested in vitro against five bacteria: Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica, Staphylococcus aureus and Bacillus subtilis and the yeast Candida albicans. B. bullata essential oil showed stronger antibacterial effects comparing to B. nigra oil. Consequently, B. bullata essential oil holds promising antimicrobial potential, confirming its traditional medical use.
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The aim of the present study was to investigate and identify the essential oil constituents of Leucas indica (L.) R.Br. (Lamiaceae). The chemical composition of the hydro-distilled essential oil was obtained from the flowering aerial parts of L. indica for the first time. The oil was analyzed by gas chromatography equipped with flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). Fifty-six compounds were identified, representing 99.1% of the total oil. The main constituents were β-caryophyllene (51.1%) and α-caryophyllene (10.2%). The oil was found to be rich in sesquiterpene hydrocarbons (71.8%).
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The essential oil obtained from the aerial parts of Croton bonplandianus Baill. was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). A total of 37 compounds have been identified, representing 96.2% of the total oil. The main constituents were identified as beta-caryophyllene (16.7%), germacrene D (14.7%), borneol (8.3%), Z-beta-damascenone (6.(%), isobornyl acetate (6.2%), alpha-humulene (6.1%), germacrene A (5.2%) and caryophyllene oxide (4.5%). The oil was rich in sesquiterpene hydrocarbons (60.1%).
Flora of Ranga Reddi District Andhra Pradesh, India
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Chemical composition and antimicrobial activity of the essential oil of Anaphalis nubigena var. monocephala
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Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel
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