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Chemical composition, antioxidant and anticholinesterase potentials of essential oil of Rumex hastatus D. Don collected from the North West of Pakistan

  • Sajjad Ahmad1,
  • Farhat Ullah1Email author,
  • Abdul Sadiq1,
  • Muhammad Ayaz1,
  • Muhammad Imran1,
  • Imdad Ali2,
  • Anwar Zeb1,
  • Farman Ullah3 and
  • Muhammad Raza Shah2
BMC Complementary and Alternative MedicineBMC series – open, inclusive and trusted201616:29

https://doi.org/10.1186/s12906-016-0998-z

Received: 1 October 2015

Accepted: 12 January 2016

Published: 25 January 2016

Abstract

Background

Ethnomedicinally Rumex hastatus D. Don has been used since long for various ailments especially in neurological disorders. The reported data and the importance of Rumex genus demonstrate the vital medicinal value of R. hastatus.

Methods

In the current investigational study, isolation of essential oil and its antioxidant and anticholinesterase assays were performed. The essential oil of R. hastatus was analyzed by GC-MS for the first time. The essential oil was evaluated for anticholinesterase and antioxidant assays. The anticholinesterase assay was conducted at various concentrations (62.5 to 1000 μg/ml) against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Similarly, the antioxidant potential was determined using DPPH and ABTS free radicals.

Results

The GC-MS analysis of essential oil showed 123 components. The result recorded for the anticholinesterase assays demonstrated a marked potential against AChE and BChE with IC50 values of 32.54 and 97.38 μg/ml respectively which were comparable with the positive control i.e., galanthamine (AChE, IC50 = 4.73 μg/ml and BChE, IC50 = 11.09 μg/ml). The antioxidant assays against DPPH and ABTS free radicals also exhibited significant scavenging potential with IC50 values of 3.71 and 6.29 μg/ml respectively, while for ascorbic acid the IC50 value was <0.1 μg/ml against both free radicals.

Conclusions

Based on the current investigational studies, it may be concluded that R. hastatus is an effective source of essential oil's components having anticholinesterase and antioxidant potentials, which after subjecting to drug development may lead to novel drug candidates against neurodegenerative disorders.

Keywords

Essential oil Acetylcholinesterase Butyrylcholinesterase Antioxidant GC-MS Free radicals Rumex hastatus

Background

A brief history of medicine demonstrates the use of herbal medicine for the effective treatment of various ailments. Herbal medicine has been used since long in various forms including the decoction, powdered sample, oleoresins, crude extracts, fixed oil, essential oil etc [1]. Various plants have been used in multiple types of food items for preservation and therapeutic effects [2]. In this regards, essential oils have been manifested by several reporters to play a major role. Essential oils have the property to attenuate the effects of free radicals, e.g, reactive oxygen species (ROS) which are derived from metabolism of oxygen and exogenous agents [3]. ROS are responsible for wide variety of diseased conditions including oxidative stress and nervous disorders [4]. Essential oils are well-known for their radicals scavenging properties and amelioration of various cognitive disorders. Among the cognitive disorders, Alzheimer’s disease (AD) is the most common in elderly people [5]. One of the best therapeutic approaches for AD is to increase the concentration of the neurotransmitter (Acetylcholine) by inhibiting the enzyme (acetylcholinesterase) responsible for its breakdown. Various drugs originated either from natural or synthetic sources are being used for the management of AD and other nervous disorders [6]. Similarly, it has also been reported that oxidative stress are responsible for wide variety of mental diseases due to neuronal degeneration and other factors. Oxidative stress is mainly developed due to increase in concentration of free radicals within the body. The free radicals have been reported by numerous researchers to possess multiple destructive properties, due to which interest has been focused to scavenge the free radicals somehow and avoid their deteriorating effects [7]. In this context, investigators are trying to explore more and more sources of natural and synthetic bioactive principles [8]. The natural drugs are being preferred over the synthetic due to their negligible harmful and deleterious effects [9]. That’s why researchers are trying to explore novel sources of natural medicine [1018]. Among the natural sources, herbal medicines have been shown promising results due to the presence of numerous secondary metabolites and essential oils. Essential oils isolated from various plants have been reported to possess marked acetylcholinesterase inhibitory and radicals scavenging potential [1921]. Traditional knowledge also demonstrates the use of essential oils for various nervous system disorders [22].

R. hastatus D. Don belongs to the family Polygonaceae. Various members of this family have been reported to be used against paralysis, headache and other nervous system disorders [2326]. Various solvent samples of R. hastatus have recently been reported to possess strong anticholinesterase and antioxidant potentials [26]. To date, the chemical composition of essential oil of R. hastatus has not been reported or evaluated for any pharmacological activity. Based on the literature survey and medicinal importance of R. hastatus, the current investigational study is arranged to isolate the essential oil, analyze the chemical composition and to evaluate for the anticholinesterase and antioxidant potentials, which may be a possible remedy for oxidative stress and nervous system disorder.

Methods

Plant sample collection

The aerial parts of R. hastatus were collected from the proximity of University of Malakand. The plant was identified by plant taxonomist Ali Hazrat and deposited with voucher number (1015SJ) in the herbarium of Department of Botany, Shaheed Benazir Bhutto University Sheringal, Dir (U), KPK, Pakistan. Extraction of essential oil of R. hastatus was performed by hydrodistillation using clevenger type apparatus [27]. The essential oil obtained was stored at -20 °C until required.

Chemicals and drugs

DPPH (Sigma Aldrich CHEMIE GmbH USA, code 101341986), K2S2O4 (Riedel-de Haen Germany), ABTS (Sigma Aldrich USA, code 1001551916), Gallic acid (GmbH USA), Folin Ciocalteu reagent (Merck Co. Germany). AChE (Electric eel type-VI-S, Sigma-Aldrich GmbH USA, code 1001596210), BChE (Equine serum Lyophilized Sigma-Aldrich GmbH USA, code 101292670), Acetylthiocholine iodide (Sigma-Aldrich UK, code 101303874), Butyrylthiocholine Iodide (Sigma-Aldrich Switzerland, code 101334643), DTNB (Sigma-Aldrich Germany, code 101261619), Galanthamine hydrobromide Lycoris Sp. (Sigma-Aldrich France, code G1660). K2HPO4, KH2PO4, KOH. All the chemical used were of analytical grade.

Gas Chromatography (GC) analysis

The GC analysis of essential oil was carried out via gas chromatograph Agilent USB-393752 (Agilent Technologies, Palo Alto, CA, USA) with HHP-5MS 5 % phenylmethyl siloxane capillary column (30 m × 0.25 mm × 0.25 μm film thickness; Restek, Bellefonte, PA) connected with FID detector. The oven was set at temperature of 70 °C for one minute and then increased to 180 °C at the rate of 6 °C/min for 5 min and lastly to 280 °C at the rate of 5 °C/min for 20 min. The temperature of injector and detector were maintained at 220 °C and 290 °C correspondingly. The flow rate of carrier gas i.e., Helium was 1 ml/min and the diluted samples (1/1000 in n-pentane, v/v) of 1 μl were manually injected in the split-less mode.

Gas Chromatography–Mass Spectrometry (GC-MS) analysis

The GC/MS of the essential oil was performed via USB-393752 gas chromatograph (Agilent Technologies, Palo Alto, CA, USA) with a HHP-5MS 5 % phenylmethyl siloxane capillary column (30 m × 0.25 mm × 0.25 μm film thickness; Restek, Bellefonte, PA) outfitted with an Agilent HP-5973 mass selective detector in the electron impact mode (Ionization energy: 70 eV) working under the experimental conditions as those maintained for GC.

Identification of components

The recognition of all the major constituents of oil was performed by comparing their retention times with the authentic compounds in the literature. Identification of compounds was further processed through the spectral data obtained from the Wiley and NIST libraries as well as fragmentation patterns’ comparisons of the mass spectra with data reported in literature or with those of mass spectra from literature [28, 29]. Each determination was processed in duplicate.

Anticholinesterase assays

Anticholinesterase (AChE and BChE inhibitions) activity was performed for the essential oil of R. hastatus by spectrophotometric analysis following the method of Ellman's assay [30]. The substrates used were acetylthiocholine iodide and butyrylthiocholine iodide. Briefly, 5 μL of 0.03 U/mL AChE and 0.01 U/mL BChE were taken in a cuvette and 205 μL of essential oil having concentration of 62.5–1000 μg/mL were transferred to them using micropipette. Similarly, 5 μLof DTNB was also added to this afterwards. The mixtures obtained were kept in water bath for 15 min at the temperature of 30 °C. After incubation, 5 μL of the Substrates were added to the mixture to optimize the reaction. A double beam spectrophotometer was used to measure the reaction time at 412 nm via a double beam spectrophotometer (Thermo electron corporation USA). Absorption values were obtained for 4 min. Meanwhile, the yellow colored mixtures indicated the formation of 5-thio-2-nitrobenzoate anion as a reaction product of thiocholines and DTNB. White assay was also performed without enzymes and plant samples to check the non-enzymatic hydrolysis of substrate. The mixture which contained all the components excluding essential oil was marked as control. Percent enzyme activity and percent inhibition were recorded as follows.
$$ \mathrm{V} = \frac{\varDelta \mathrm{Abs}}{\varDelta \mathrm{t}} $$
$$ \%\ \mathrm{enzyme}\ \mathrm{activity} = \frac{\mathrm{V}}{{\mathrm{V}}_{\max }}\times 100 $$
$$ \%\ \mathrm{enzyme}\ \mathrm{inhibition}=100-\%\ \mathrm{enzyme}\ \mathrm{activity} $$

(Where V symbolizes the rate of reaction in the presence of inhibitor and Vmax stands for rate of reaction without inhibitor)

DPPH radical scavenging assay

The DPPH radical scavenging potential was evaluated for essential oil of R. hastatus following previously described procedure [31]. DPPH solution (0.004 %) was prepared in methanol to get a deep violet colored solution. Similarly, stock solution of essential oil was prepared in ethanol having concentration of 1 mg/mL. The stock solution was serially diluted to get the concentrations of 62.5 to 1000 μg/mL. Afterwards, 0.1 mL of each concentration was added to the 3 mL of DPPH solution. The mixture obtained was incubated at 23 °C for 30 min in dark. After incubation the absorbance of each sample were recorded at the wavelength of 517 nm using double beam spectrophotometer. Ascorbic acid was used as positive control. All the samples were processed in triplicates and the percent activity was recorded as mean ± SEM. The percent radical scavenging potential was figured out using the following formula;
$$ \%\ \mathrm{scavenging}=\frac{\mathrm{absorption}\ \mathrm{of}\ \mathrm{control}-\mathrm{absorption}\ \mathrm{of}\ \mathrm{test}\ \mathrm{sample}}{\mathrm{absorption}\ \mathrm{of}\ \mathrm{control}}\times 100 $$

ABTS radical scavenging assay

The 2, 2-azinobis [3-ethylbenzthiazoline]-6-sulfonic acid (ABTS) free radicals scavenging assay of the essential oil was evaluated followed standard procedure [11]. ABTS solution 7 mM and potassium persulfate solution 2.45 mM were prepared and mixed thoroughly. The solution prepared was put in dark overnight for the production of free radicals. After incubation time the absorbance of solution was adjusted at 745 nm to 0.7 by the addition of 50 % methanol. Test samples having volume of 300 μl was taken in a test tube and 3 mL ABTS solution was added to it. The solution was transferred to the cuvette and absorbance values were taken for six minutes using double beam spectrophotometer. Ascorbic acid was used as positive control. All the samples were run in triplicate and percent ABTS radical scavenging potential was figured out using the following formula;
$$ \%\ \mathrm{scavenging}\ \mathrm{activity}=\frac{\mathrm{control}\ \mathrm{absorbance}-\mathrm{sample}\ \mathrm{absorbance}}{\mathrm{control}\ \mathrm{absorbance}}\times 100 $$

Estimation of IC50 values

The median inhibitory concentration i.e., IC50 values of AChE, BChE, DPPH and ABTS were determined by a linear regression analysis of the percent inhibition versus the concentrations of test samples through MS Excel program.

Statistical data analysis

All the tests were conducted in triplicate and the values were tabulated as mean ± S.E.M. Significant difference of the percent inhibition of various test samples was analyzed via two way ANOVA following Bonferroni’s post test using GraphPad Prism software in which the P < 0.05 were considered significant.

Results and discussion

In the current investigational study the radical scavenging potential of volatile oil was studied based on spectrophotometric analysis. The sources of free radicals employed were DPPH and ABTS, which have maximum absorbance values at 517 nm and 745 nm respectively. After getting scavenged by antioxidant compounds the colors of DPPH (violet) and ABTS (blue) solution change into yellow. Change in the color results in decrease of absorbance values which is directly proportional to the amount of radical scavenging compounds in the solution [32, 33].

Similarly, the anticholinesterase activity is based on the hydrolysis of acetylthiocholine iodide and butyrylcholine iodide by the formation of the yellow 5-thio-2- nitrobenzoate anion as a result of the reaction of DTNB with thiocholines, catalyzed by enzymes at a wavelength of 412 nm using spectrophotometer or microplate reader. Acetylthiocholine iodide and butyrylthiocholine iodide work as substrate of the reaction, while the DTNB is utilized for the measurement of cholinesterase activity. The percent inhibition of enzymatic activity is calculated from the rate of change in absorption of the reaction mixture [34].

The available literature on etiology of diseases demonstrate multiple causative agents responsible for specific disease [35]. In the context of Alzheimer’s disease, numerous investigators have reported the role of various causative agents along with various successful approaches [36]. Like all neurodegenerative disorders, the free radicals have a prominent role in the induction and progression of AD [37]. By avoiding or attenuating the causative agents one can hinder the progression of a specific disease. In case of neurodegenerative disorders, the scavenging of free radicals can be a vital target. Various researchers have demonstrated the effective role of natural antioxidants especially the essential oils to combat the free radicals [38]. Similarly, one of the most widely employed treatment strategies for AD i.e., the inhibition of AChE to increase the concentration of neurotransmitter is highly recommended [39]. In this regard, essential oils are being investigated by advanced researchers with better results. Essential oils obtained from various plants possess marked anti-Alzheimer’s potential due to the presence of wide variety of valuable compounds in it [40, 41]. The anticholinesterase potential of essential oil of Rumex hastatus has been summarized in the Table 1, while the Table 2 shows various parameters of the compounds present in the essential oil of this plant. The GC-MS analysis of essential oil of R. hastatus demonstrates a total of 123 components as shown in Table 3. The anticholinesterase activity of essential oil of R. hastatus might be due to its hydrophobic nature because of the good affinity of hydrophobic active site of AChE [42, 43]. Some of the most common components of essential oils i.e., palmitic acid, myristic acid, pelargic acid, capric acid, docosane, cetane, velleral, acetone, methyl palmitate, widdrol, isolongifolol, ophytadiene, drimenol and levulinic acid have been found in the essential oil of R. hastatus. Some of these components have been reported previously by other investigators to possess antioxidant and anticholinesterase potentials [4449]. The percent antioxidant potential of essential oil is illustrated in the Fig. 1. The peaks given in the Table 2 shows various volatile compounds like 5-ethyl-2(5H)-furanone, trimethylacetic anhydride, cyclooctanone, 5-methyl-3-heptanol, methyl 2-vinylbutanoate, 2-(p-methylphenyl)-2-nitropropne, azelaaldehydic acid, 2,4,6-trimethyloctane and trans-3-nonen-2-one with retention times of 6.447, 6.818, 10.958, 11.363, 11.761, 12.97, 13.171, 13.308, 15.063 and 19.213 min respectively. Going to the detail of various components of essential oil of R. hastatus, it is clear that the marked anticholinesterase potential shown by essential oil is observed due to the presence of wide variety of compounds in it. Essential oil demonstrated 74.90, 71.70, 67.26, 61.64, 54.32 % AChE inhibition at 1000, 500, 250, 125, 62.5 μg/ml respectively. Similarly, the BChE inhibition exhibited by essential oil was recorded as 71.32, 66.33, 46.32, 52.73, 57.00 % at 1000, 500, 250, 125, 62.5 μg/ml respectively. The essential oil attain IC50 values of 32.54 and 97.38 μg/ml for AChE and BChE inhibitions respectively. The anticholinesterase potential shown by essential oil goes parallel with the positive control which is also obvious from the Fig. 2 (a & b) with the correlation coefficient of 0.961 and 0.988 for essential oil versus AChE and BChE respectively. Apart from the anticholinesterase potential of essential oil, the antioxidant potential of essential oil of various plants has been reported with discrimination by various investigators [50, 51]. In our current investigational study, the free radicals scavenging assay of essential oil of R. hastatus against DPPH and ABTS was significant and almost comparable with the positive control. From Fig. 1, it is clear that essential oil exhibited marked potential with IC50 of 3.71 and 6.29 μg/ml against DPPH and ABTS respectively, which is also comparable with the previously reported literature. The previously reported data of R. hastatus verifies its anticholinesterase and antioxidant potentials which may be linked to the current investigational studies [26].
Table 1

Anticholinesterase activity of essential oil of Rumex hastatus at various concentrations

Samples

Enzymes

Conc. μg/ml

Conc. μg/ml

Conc. μg/ml

Conc. μg/ml

Conc. μg/ml

IC50 μg/ml

62.5

125

250

500

1000

EO

AChE

54.32 ± 1.33

61.64 ± 1.60

67.26 ± 1.24

71.70 ± 1.63

74.90 ± 0.52

32.54

EO

BChE

46.32 ± 3.50

52.73 ± 0.78

57.00 ± 2.80

66.33 ± 0.49

71.32 ± 4.8

97.38

Gal

AChE

72.08 ± 1.04

78.58 ± 1.12

83.70 ± 1.60

89.00 ± 1.15

96.65 ± 1.34

04.73

Gal

BChE

66.87 ± 1.27

73.67 ± 0.88

79.95 ± 2.01

86.62 ± 1.67

91.61 ± 0.43

11.09

Data is expressed as Mean ± SEM; EO and Gal are abbreviated for Essential oil and Galanthamine respectively

Table 2

Parameters of various components of essential oil of Rumex hastatus

RT (min)

Height

Height (%)

Area

Area (%)

Area Sum %

Base Peak m/z

Width

6.447

254413

18.51

620057

20.82

5.87

83

0.127

6.818

324110

23.59

626045

21.02

5.93

57.1

0.077

10.958

430958

31.36

822529

27.61

7.79

55.1

0.074

11.363

250143

18.2

592697

19.9

5.61

59.1

0.09

11.761

278058

20.23

665761

22.35

6.31

59.1

0.094

12.97

177060

12.88

399792

13.42

3.79

43.1

0.097

13.171

312841

22.77

664487

22.31

6.29

55.1

0.08

13.308

1E + 06

100

3E + 06

100

28.21

57.1

0.1

15.063

159790

11.63

336861

11.31

3.19

55.1

0.08

19.213

450356

32.77

782083

26.26

7.41

133.1

0.064

Table 3

List of components of essential oil of Rumexhastatus

S.No

Compound Label

Common name

RT

Formula

Hits (DB)

1.

Trans-dideuterioxy-cyclopentene

NF

5.757

C5H6D2O2

10

2.

1-Nonen-4-ol

NF

5.884

C9H18O

10

3.

Ethyl 2-hydroxybutyrate

NF

6.169

C6H12O3

10

4.

2(5H)-Furanone, 5-ethyl

NF

6.445

C6H8O2

10

5.

Pentanoic acid, 4-oxo

Levulinic acid

6.68

C5H8O3

10

6.

2,2-Dimethylpropanoic anhydride

Trimethylacetic anhydride

6.819

C10H18O3

10

7.

Heptanoic acid

Enanthic acid

7.117

C7H14O2

10

8.

Ethanethioic acid, S-(2-methylpropyl) ester

NF

7.374

C6H12OS

10

9.

4-Octanol, 7-methyl

NF

7.511

C9H20O

10

10.

4-(Tetrahydrofuranyl-2-oxy)-4-methyl-2-pentanone

NF

7.619

C10H18O3

10

11.

Cyclopropane, 1,2-dimethyl-1-pentyl

NF

7.698

C10H20

10

12.

n-Nonanal

Nonanal

7.852

C9H18O

10

13.

Cyclooctanone

NF

8.275

C8H14O

10

14.

1,4,4-Trimethylcyclohexa-2-en-1-ol

NF

8.494

C9H16O

10

15.

3-Octanol, 2-methyl

NF

8.716

C9H20O

10

16.

2-Oxatricyclo[3.3.1.1(3,7)]decane, 1-methyl-

NF

9.116

C10H16O

10

17.

Succinimide, N-methoxy

NF

9.338

C5H7NO3

10

18.

4-Heptanol, 2-methyl

NF

9.547

C8H18O

10

19.

Ethanone, 1-(methylphenyl)

Methylacetophenone

9.712

C9H10O

10

20.

Decanal

NF

10.099

C10H20O

10

21.

3-Heptanol, 2,4-dimethyl

NF

10.328

C9H20O

10

22.

Cyclooctanone

NF

10.957

C8H14O

10

23.

1-Decyne (CAS) $$ Octylacetylene

NF

11.165

C10H18

10

24.

3-Heptanol, 5-methyl

NF

11.364

C8H18O

10

25.

Nonanoic acid

Pelargic acid

11.456

C9H18O2

10

26.

ETHYL AMYL CARBINOL

NF

11.763

C8H18O

10

27.

CIS-SABINENE HYDRATE

NF

11.96

C10H18O

10

28.

1,8-Bisoxiranylnonane

NF

12.047

C13H24O2

10

29.

3-Heptanone, 4-methyl

NF

12.817

C8H16O

10

30.

Methyl 2-vinylbutanoate

NF

12.972

C7H12O2

10

31.

trans-3-Nonen-2-one

NF

13.171

C9H16O

10

32.

Octane, 2,4,6-trimethyl

NF

13.309

C11H24

10

33.

2H-Pyran-2-one, 6-heptyltetrahydro

Delta.-laurolactone

13.471

C12H22O2

10

34.

Decanoic acid

Capric acid

13.601

C10H20O2

10

35.

3-Octanol

NF

14.002

C10H22O

10

36.

Ethyl 3,3-dimethylbutyrate

NF

14.246

C8H16O2

1

37.

5-Hexenal

NF

14.547

C6H10O

10

38.

2-Pentenoic acid, 4-hydroxy

NF

14.878

C5H8O3

10

39.

Nonanoic acid, 9-oxo-, methyl ester

Azelaadehydic acid

15.065

C10H18O3

10

40.

Thiophene, 2-methoxy

NF

15.345

C5H6OS

3

41.

Octanoic acid, 8-hydroxy

NF

15.49

C8H16O3

10

42.

Oxirane, octyl

NF

15.604

C10H20O

10

43.

Butane, 1,1'-oxybis[3-methyl

NF

15.875

C10H22O

5

44.

3-Hydroxy-4-methoxystyrene

NF

16.153

C9H10O2

7

45.

Octanoic Acid

n-Caprylic acid

16.355

C8H16O2

10

46.

3-Hexanol, 3,5-dimethyl

NF

16.55

C8H18O

10

47.

2-Tridecen-1-ol, (E)

NF

16.643

C13H26O

10

48.

1-Isopropyl-4,7-dimethyl-1,2-dihydronaphthalene

Alpha-Calcorene

16.877

C15H20

10

49.

4-(5',5'-dimethyl-2'-methylidene-3',8'-dioxabicyclo[5.1.0]oct-4-ylidene)-2-b…

NF

17.084

C13H18O3

5

50.

9-Methyl-S-octahydrophenanathracene

NF

17.192

C15H20

10

51.

Z-10-Tetradecen-1-ol acetate

NF

17.373

C16H30O2

10

52.

Dodecanamide, N,N-bis(2-hydroxyethyl)

NF

17.737

C16H33NO3

10

53.

5,8-Dimethyl-1,2,3,4-tetrahydro-1-naphthol

NF

17.847

C12H16O

3

54.

3-Hexen-1-ol, benzoate, (Z)

NF

17.917

C13H16O2

10

55.

Nonanoic acid

Pelargic acid

18.014

C9H18O2

10

56.

Nonanedioic acid, monomethyl ester

NF

18.153

C10H18O4

10

57.

(-)-Caryophyllene oxide

Caryophyllene oxide

18.311

C15H24O

10

58.

(+-)-Andirolactone

Andirolactone

18.513

C11H14O2

10

59.

Ledol

NF

18.64

C15H26O

10

60.

(. + -.)-2-Methyl-6-p-tolyl-4-heptanol (diastereoisomer II)

NF

18.693

C15H24O

9

61.

Propanal, 2,2-dimethyl

NF

18.777

C5H10O

1

62.

2,6,10-Trimethylundecan-(5E)-2,5,9-trien-4-one

NF

18.869

C14H22O

10

63.

7-oxabicyclo[4.1.0]heptane, 1-(1,3-dimethyl-1,3-butadienyl)-2,2,6-trimethyl-

NF

19.004

C15H24O

10

64.

Octanoic acid, 6,6-dimethoxy-, methyl ester

NF

19.087

C11H22O4

10

65.

2-(p-methylphenyl)-2-nitropropane

NF

19.212

C10H13NO2

10

66.

Azelaic Acid

Anchoic acid

19.589

C9H16O4

4

67.

cis-9-oxabicyclo[6.1.0]non-2-ene

NF

19.736

C8H12O

10

68.

1-Buten-3-one, 1-(2-carboxy-4,4-dimethylcyclobutenyl)

NF

19.864

C11H14O3

10

69.

Campherenone

Campherenone

20.056

C15H24O

10

70.

11-Hexadecyn-1-ol

NF

20.231

C16H30O

10

71.

Cyclodecene, 1-ethyl-2-methyl-

NF

20.385

C13H24

10

72.

1,3-Dioxolane-4,5-dicarboxylic acid, 2,2-dimethyl-, dimethyl ester

NF

20.627

C9H14O6

5

73.

10-(1-Methylallyl)tricyclo[6.3.1.0(2,7)]dodeca-2(7),3,5-trien-10-ol

NF

20.768

C16H20O

4

74.

2-Acetoxy-1,1,10-trimethyl-6,9-epidioxydecalin

NF

20.894

C15H24O4

10

75.

Farnesyl Acetone C

Farnesyl Acetone

21.18

C18H30O

10

76.

17-Octadecynoic acid

NF

21.401

C18H32O2

10

77.

Tetradecanoic acid

Myristic acid

21.82

C14H28O2

10

78.

Driminol

Drimenol

22.167

C15H26O

10

79.

2,2,6-Trimethyl-1-(3-methylbuta-1,3-dienyl)-7-oxabicyclo[4.1.0]heptan-3-ol

NF

22.272

C14H22O2

10

80.

1,3,5-trimethyl-6-methyliden-tricyclo[3.2.1.0(2,7)]oct-3-en-8-endo-ol

NF

22.677

C12H16O

9

81.

1-Methyl-2-acetyl-6-methoxy-3,4-dihydronaphthalene

NF

22.933

C14H16O2

10

82.

N-(1-Cyanoethyl)(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-ylmethanesulfonamide

NF

23.386

C13H20N2O3S

10

83.

5-(ethylamino)-1,6-dimethyl-2(1H)-quinolinone

NF

23.511

C13H16N2O

10

84.

(-)-Isolongifolol

Isolongifolol

23.926

C15H26O

10

85.

Neophytadiene

Neophytadiene

24.02

C20H38

10

86.

Naphthalene, 1-(1,1-dimethylethyl)-7-methoxy-

NF

24.123

C15H18O

2

87.

2-Pentadecanone, 6,10,14-trimethyl

NF

24.218

C18H36O

10

88.

2,5,8-Trimethyltricyclo[5.3.1.1(3,9)]dodecane-2-anti,8-tnti-diol

NF

24.561

C15H26O2

3

89.

Pentadecanoic acid

Pentadecyclic acid

24.74

C15H30O2

10

90.

9,19-Cycloergost-24(28)-en-3-ol, 4,14-dimethyl-, acetate

NF

25.047

C32H52O2

4

91.

8-Keto-10-dehydrobrominated-.beta.-snyderol

NF

25.298

C15H22O2

2

92.

Widdrol

Widdrol

25.848

C15H26O

10

93.

2,4,7,9-Tetramethyl-5-decyne-4,7-diol

NF

26.036

C14H26O2

4

94.

Phenol, 2-methyl-4-(1,1,3,3-tetramethylbutyl)

NF

26.54

C15H24O

10

95.

Benzene, 1,1'-(1,2-diethyl-1,2-ethanediyl)bis[4-methoxy-

NF

26.548

C20H26O2

10

96.

(1R,3S)-2,2,3-Trimethyl-6-methylidenecyclohexane-1-carbaldehyde

NF

26.624

C11H18O

5

97.

Hexadecanoic acid, methyl ester

Methyl palmitate

26.732

C17H34O2

10

98.

1-Hexadecen-3-ol, 3,5,11,15-tetramethyl-

NF

27.371

C20H40O

10

99.

Benzo[e]isobenzofuran-1,4-dione,1,3,4,5,5a,6,7,8,9,9a-decahydro-6,6,9a-trime…

NF

27.585

C15H20O3

10

100.

Hexadecanoic acid

Palmitic acid

27.984

C16H32O2

10

101.

Butane-1,1-dicarbonitrile, 1-cyclohexyl-3-methyl-

NF

28.431

C13H20N2

10

102.

2-Methyl-2-propyl-2,5-dihydrofuran

NF

28.552

C8H14O

10

103.

5A-Methyl-3,8-dimethylene-2-oxododecahydrooxireno[2',3':6,7]naphtho[1,2-b]fu…

NF

28.643

C20H24O5

10

104.

4-(3,7,7-Trimethyl-2-oxabicyclo[3.2.0]hept-3-en-1-yl)but-3-en-2-one

NF

28.98

C13H18O2

10

105.

Cyclobutanecarboxylic acid, 2-methyloct-5-yn-4-yl ester

NF

29.064

C14H22O2

10

106.

Cyclooctenone, dimer

NF

29.439

C16H24O2

10

107.

Undecane, 6-cyclohexyl-

NF

29.639

C17H34

10

108.

2,4,5,7-Tetramethyl-2,6-octadiene

NF

30.471

C12H22

10

109.

Cyclohexane, 1,2,3,4,5,6-hexaethyl

NF

30.77

C18H36

10

110.

Cyclopentanone, 3-methyl-2-(2-pentenyl)-

NF

31.291

C11H18O

10

111.

2-Propanon

Acetone

31.44

C3H6O

10

112.

beta.-Ionol $$ 3-Buten-2-ol, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-

NF

31.703

C13H22O

10

113.

Velleral

Velleral

32.121

C15H20O2

10

114.

2-Hydrazino-2-imidazoline

NF

32.733

C3H8N4

10

115.

2H-cyclopropa[g]benzofuran, 4,5,5A,6,6A,6B-hexahydro-4,4,6b-trimethyl-2-(1-m…

NF

33.658

C15H22O

10

116.

Hexadecane

Cetane

37.132

C16H34

10

117.

Docosane

Docosane

38.808

C22H46

10

118.

4,4-6-Trimethyl-7-oxabicyclo[4.1.0]heptan-2-one

NF

39.247

C9H14O2

10

119.

1,2-Benzenedicarboxylic acid, bis(2-ethylhexyl) ester

NF

39.623

C24H38O4

10

120.

4-Allyl-1-ethoxy-3-phenylbenzo[c]-(1,2)-oxaphosphinine - 1-Oxide

NF

40.4

C19H19O3P

3

121.

Hexadecane

Cetane

41.915

C16H34

10

122.

Undecane, 3,8-dimethyl-

NF

44.76

C13H28

10

123.

4-Methyl-7-ethylizidine $$ 8-Methyl-5-ethylindolizidine

NF

58.237

C11H21N

10

Fig. 1

Antioxidant potential of essential of Rumex hastatus against DPPH and ABTS

Fig. 2

a. Regression and correlation of percent BChE inhibition of essential oil Vs Galanthamine. b. Regression and correlation of percent AChE inhibition of essential oil Vs Galanthamine

Fig. 3

Structures of some important components of essential oil of Rumex hastatus

Fig. 4

GC-MS Chromatogram of essential oil of Rumex hastatus

Some important components of essential oil and the chromatogram have been given in Figs. 3 and 4 respectively.

Conclusion

Essential oil isolated for the first time from the R. hastatus and its chemical composition demonstrates that R. hastatus is a source of valuable volatile components. Based on the anticholinesterase and antioxidant results of essential oil, it can be concluded that R. hastatus plant may be an effective source of compounds which may lead to possible palliative therapy and cure of oxidative stresses and neurodegenerative diseases.

Declarations

Acknowledgements

All authors are thankful to Dr. Ali Hazrat, Department of Botany, Shaheed Benazir Bhutto University Sheringal, Dir (U), Pakistan for the identification of plant.

Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.

Authors’ Affiliations

(1)
Department of Pharmacy, University of Malakand
(2)
International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry University of Karachi
(3)
Department of Pharmacy, Kohat University of Science &Technology

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Copyright

© Ahmad et al. 2016

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