Open Access

Biological activities and volatile constituents of Daucus muricatus L. from Algeria

  • Amel Bendiabdellah1,
  • Mohammed El Amine Dib1,
  • Nassim Djabou1, 2,
  • Hocine Allali1,
  • Boufeldja Tabti1,
  • Alain Muselli2Email author and
  • Jean Costa2
Chemistry Central Journal20126:48

DOI: 10.1186/1752-153X-6-48

Received: 27 January 2012

Accepted: 26 April 2012

Published: 30 May 2012

Abstract

Background

In order to find new bioactive natural products, the antimicrobial and antioxidant activities of essential oil components extracted from the separated organs of the Algerian medicinal and aromatic plant Daucus muricatus L. were studied.

Results

The chemical composition of essential oils obtained by hydrodistillation (HD) was investigated using Gas Chromatography–Retention Indices (GC-RI) and GC–Mass Spectrometry (GC-MS). Two types of essential oils were produced by D. muricatus: (i) The oil from roots is mainly composed by nonterpenic oxygenated compounds (59.8 g/100 g), and (ii) the aerial part oils (i.e., the leaves, stems, flowers, and umbels) was mainly composed by terpenic hydrocarbon compounds (62.3–72.2 g/100 g). The chemical composition of the volatile fraction isolated from different organs of Daucus muricatus were studied by HS–SPME/GC–RI and GC–MS after optimization of Solid Phase MicroExtraction parameters. For all organs studied, the main volatiles emitted by the plant were hydrocarbon compounds (60.7–82.2 g/100 g). Only quantitative differences between the volatiles of the separated organs studied were observed. In addition, the activity of the oil of D. muricatus against eight bacterial strains and one yeast was investigated. The oil from roots revealed active against S. aureus, while the essential oil obtained from the aerial parts was active against the yeast C. albicans.

Conclusions

Daucus muricatus essential oil seems be a promising source of natural products with potential antimicrobial activity.

Keywords

Daucus muricatus. L Essential oils HS-SPME GC/MS Antimicrobial and antioxidant activities

Background

Daucus is a genus belonging to the Apiaceae family and consists of about 600 species that are widely distributed around the world. In Algeria, the Daucus genus is represented by more than 27 species living in dry and uncultivated areas [1], and they are mostly found from Tlemcen to Mascara [1, 2]. The most prevalent of the species is Daucus carota L. (carrot) reported with eight subspecies throughout Algeria [1]. Daucus muricatus L., synonym of Artedia muricata L., Caucalis muricata L., and Platyspermum muricatum Hoffm., is widely distributed in Algeria, Spain, Portugal, Corsica, Sardinia, Sicily, Italy, the Aegean Islands, and Turkey [2]. Daucus muricatus is an annual plant 30–50 cm high, dark green, bristling at the base, with a stem thickened at the nodes and branches spreading erect. The leaves are soft and lanceolate in their periphery in segments cut into narrow strips with white flowers. The umbels opposite the leaves at the end are contracted, the fruit are large, elliptical and compressed, armed with spines expanded and confluent at the base [1, 2]. Several investigations deal with the chemical composition of essential oils of the Daucus species [327]. While no study has investigated D. muricatus essential oils, most of them have reported the chemical composition of essential oils from D. carota and its subspecies [3, 4, 616, 20, 22, 23, 2527]. However, only three studies have reported the chemical composition of essential oils from Daucus species from Algeria. The first reported the chemical composition of the essential oil of D. reboudii Coss. [17], and the other two reported the chemical composition of the oil from D. crinitus Desf. [18, 19]. Previous reports showed that the chemical composition of Daucus species was more dominated by monoterpene hydrocarbon compounds such α-pinene and sabinene [3, 4, 10, 14, 15], and occasionally by phenylpropanoids compounds such as apiol, myristicin, and isochavicol [3, 1416]. Several studies recently investigated the biological activity of Daucus essential oils [6, 10, 12, 19, 20]. However, there remain many species and subspecies of Daucus that have not yet been examined.

As part of our ongoing chemical investigation of the essential oils from the Algerian Daucus genus [18] and our search for active natural products to fight nosocomial infections, we investigated for the first time the chemical composition and biological activities of Daucus muricatus L. through the study of: (i) the volatile components of D. muricatus roots, leaves, stems, flowers, and umbels extracted by hydrodistillation and by solid phase microextraction (SPME) using gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS), (ii) the antibacterial activity of D. muricatus essential oil against nine species of microorganisms involved in nosocomial infections using paper disc diffusion and agar dilution methods.

Results and discussion

Essential oil chemical composition

GC–RI and GC–MS analysis of D. muricatus essential oils obtained from the roots, stems, leaves, flowers, and umbels that accounted for 92.8, 94.7, 94.5, 95.4, and 95.7 g/100 g of the oils, respectively and allowed the identification of 99 compounds. Their retention indices, yields, and relative concentrations expressed in g/100 g of essential oil are shown in Table 1. Among these, 39 monoterpenes, 32 sesquiterpenes, 22 nonterpenic compounds, three diterpenes, two phenylpropanoids, and one C13-isopropenoid were identified. All components were identified by comparison of their EI–MS and GC-retention indices with those of our laboratory-produced “Arômes” library, with the exception of nine components that were identified by comparison with spectral data and retention indices from the literature (see Table 1). Two types of essential oils were produced by D. muricatus. The root oils are mainly composed by oxygenated compounds (59.8 g/100 g), and the aerial part oils (i.e., the leaves, stems, flowers, and umbels) were dominated by the occurrence of hydrocarbon compounds (62.3–72.2 g/100 g). The main components of root oil were nonterpenic aliphatic compounds that accounted for 56.7 g/100 g, such as eicosane (18.6 g/100 g), undecan-2-one (10.2 g/100 g), and tridecanol (6.4 g/100 g). Conversely, the main components of aerial organs of D. muricatus were monoterpene hydrocarbons (52.0–58.5 g/100 g). For all organs studied, limonene (21.9–24.0 g/100 g) and α-pinene (9.9–21.8 g/100 g) were the main components. Their relative abundances were followed by that of sabinene (4.7–8.1 g/100 g) in stems, leaves and flowers, and trans-sabinyl acetate in umbels (12.1 g/100 g). On moving from the bottom to the top of the plant, we noted that the relative concentrations of nonterpenic compounds decreased as follows: 56.7 g/100 g in the roots, 12.5 g/100 g in the stems, 7.7 g/100 g in the leaves, 4.0 g/100 g in the flowers, and then 3.6 g/100 g in the umbels.
Table 1

Composition of the essential oils of D. muricatus (roots, leaves, stems, flowers and umbels)

      

Separated organse

 

Componentsa

lRIab

RIac

RIpd

Aerial parts

Stems

Leaves

Flowers

Umbels

Roots

Identificationf

1

Nonane

900

898

899

1.0

0.5

1.3

1.1

0.3

-

RI, MS

2

α-Thujene

932

923

1011

0.6

tr

0.2

0.7

0.1

-

RI, MS

3

α- Pinene

936

931

1016

16.7

9.9

18.9

14.3

21.8

0.5

RI, MS

4

Camphene

950

944

1056

0.3

0.2

0.2

0.2

0.8

tr

RI, MS

5

Thuja-2,4 (10) diene

946

945

1085

tr

0.2

0.1

tr

-

-

RI, MS

6

Sabinene

973

967

1111

18.9

5.1

4.7

8.1

4.6

0.2

RI, MS

7

β-pinene

978

970

1102

2.5

2.1

1.8

2.8

1.4

0.1

RI, MS

8

Myrcene

987

980

1152

1.8

2.1

2.3

1.6

2.6

-

RI, MS

9

α-Phellandrene

1002

997

1140

0.6

0.5

0.4

0.6

0.2

-

RI, MS

10

α-Terpinene

1013

1008

1158

1.1

1.1

1.1

1.5

0.8

0.1

RI, MS

11

p-Cymene

1015

1012

1147

1.3

4.4

1.4

0.9

1.4

0.1

RI, MS

12

Limonene

1025

1022

1195

14.2

22.6

21.3

24.0

21.9

0.3

RI, MS

13

(Z)-β-Ocimene

1029

1025

1215

0.1

0.1

0.1

tr

0.2

tr

RI, MS

14

γ-Terpinene

1051

1049

1239

2.6

2.4

1.6

3.1

1.1

tr

RI, MS

15

trans-Sabinene hydrate

1053

1052

1438

0.2

0.1

0.1

0.3

tr

-

RI, MS

16

Nonan-2-one

1070

1073

1392

0.1

0.6

0.1

tr

0.1

0.3

RI, MS

17

p-Cymenene

1075

1077

1420

0.6

0.7

0.1

tr

tr

0.1

RI, MS

18

Terpinolene

1082

1079

1292

0.3

0.6

0.3

0.7

0.2

0.1

RI, MS

19

Linalool

1083

1085

1392

0.1

tr

0.4

0.3

0.2

-

RI, MS

20

Undecane

1100

1100

1098

0.6

2.1

1.9

0.4

0.9

0.1

RI, MS

21

Limonene-1,2-epoxide

1117

1119

1446

0.2

0.2

0.2

0.3

0.4

0.9

RI, MS

22

trans-Pinocarveol

1126

1120

1632

0.3

0.7

0.1

0.2

0.2

0.2

RI, MS

23

trans-2-Nonenal

1135

1133

1525

0.2

1.2

0.4

0.1

0.2

1.1

RI, MS

24

Pinocarvone

1137

1135

1520

0.1

0.4

0.1

0.1

tr

0.1

RI, MS

25

Borneol

1150

1149

1670

0.1

0.2

0.1

tr

0.1

tr

RI, MS

26

Cryptone

1160

1159

1642

0.2

0.5

0.3

0.1

0.3

0.2

RI, MS

27

Terpinen-4-ol

1164

1160

1563

2.7

1.1

0.8

3.1

0.8

1.7

RI, MS

28

Decan-2-one

1176

1170

1503

0.1

0.8

0.3

0.2

0.1

0.2

RI, MS

29

α-Terpineol

1176

1177

1685

0.2

0.3

0.1

0.1

tr

tr

RI, MS

30

Myrtenol

1178

1182

1763

tr

0.5

0.1

0.1

0.2

0.7

RI, MS

31

Decanal

1188

1185

1481

tr

0.8

0.1

0.1

tr

0.2

RI, MS

32

Dodecane

1200

1199

1201

tr

0.2

0.1

tr

0.1

0.3

RI, MS

33

Citronellol

1213

1211

1724

0.1

0.1

0.1

tr

-

tr

RI, MS

34

Carvone

1214

1215

1749

tr

0.2

0.1

tr

-

tr

RI, MS

35

Pulegone

1215

1216

1602

tr

0.1

tr

tr

-

-

RI, MS

36

p-Anisaldehyde

1218

1219

2049

tr

0.6

tr

tr

0.3

-

RI, MS

37

Geraniol

1235

1235

1799

0.1

0.1

0.1

0.2

-

tr

RI, MS

38

trans-Myrtanol

1240

1236

1858

tr

0.1

0.2

0.2

0.5

-

RI, MS

39

cis-Chrysanthenyl acetate

1253

1242

1548

0.3

2.2

0.5

tr

0.1

0.2

RI, MS

40

α-Terpinen-7-al

1257

1256

1763

0.1

0.2

0.2

0.4

0.3

tr

RI, MS

41

Thymol

1267

1264

2149

tr

0.1

0.1

0.1

-

0.6

RI, MS

42

Bornyl acetate

1270

1266

1536

0.2

0.6

0.2

0.1

0.4

0.9

RI, MS

43

Undecan-2-one

1273

1270

1579

0.3

3.9

0.5

0.3

0.8

10.2

RI, MS

44

trans-Sabinyl acetate

1278

1271

1650

2.6

1.5

0.7

0.2

12.1

3.1

RI, MS, Ref1

45

Carvacrol

1278

1278

2224

tr

0.2

0.4

tr

0.1

0.5

RI, MS

46

Undecan-2-ol

1287

1285

1723

0.1

0.3

0.1

tr

-

1.2

RI, MS

47

Myrtenyl acetate

1332

1320

1701

0.1

0.1

0.2

0.1

tr

0.3

RI, MS

48

δ-Elemene

1340

1337

1535

0.2

0.5

1.7

0.1

0.2

-

RI, MS

49

Geranyl acetate

1362

1360

1715

tr

0.2

tr

2.3

-

0.2

RI, MS

50

Undecanol

1363

1365

1820

0.2

0.6

1.1

1.2

0.1

0.3

RI, MS

51

α-Copaene

1379

1377

1488

0.2

0.6

0.5

0.2

0.5

-

RI, MS

52

β-Bourbonene

1379

1383

1496

tr

0.4

0.3

0.2

0.1

-

RI, MS

53

β-Elemene

1389

1390

1570

0.3

0.3

0.1

0.2

0.5

-

RI, MS

54

Dodecanal

1389

1395

1673

tr

0.1

0.1

0.2

tr

1.9

RI, MS

55

Aristolene

1418

1420

1553

0.1

tr

0.1

0.3

0.1

 

RI, MS

56

trans-Caryophyllene

1424

1422

1586

1.8

0.6

3.8

2.4

2.1

0.3

RI, MS

57

Geranyl acetone

1429

1426

1842

0.1

0.4

0.2

0.3

0.4

0.1

RI, MS

58

β-Copaene

1430

1430

1579

tr

0.1

0.1

tr

0.4

-

RI, MS

59

α-Humulene

1455

1450

1655

0.4

0.4

0.5

0.3

0.4

0.5

RI, MS

60

β-Ionone

1468

1460

1902

0.5

0.2

0.1

0.8

0.4

-

RI, MS

61

Dodecanol

1472

1468

1754

0.2

0.2

0.2

tr

0.1

3.7

RI, MS

62

γ-Muurolene

1473

1471

1667

0.1

0.9

0.3

0.1

-

-

RI, MS

63

Germacrene D

1479

1476

1665

1.5

0.2

1.6

1.4

2.9

1.5

RI, MS

64

trans-β-Bergamotene

1480

1475

1598

tr

tr

tr

0.1

tr

0.8

RI, MS

65

6-epi-Shyobunone

1481

1480

1855

0.1

0.1

0.1

0.2

0.3

0.3

RI, MS

66

γ-Humulene

1483

1487

1682

0.2

0.4

0.2

0.4

0.1

-

RI, MS

67

Bicyclogermacrene

1494

1490

1706

0.4

0.4

0.3

0.2

0.2

-

RI, MS

68

α-Muurolene

1496

1498

1710

0.4

0.2

0.3

0.4

0.2

-

RI, MS

69

Shyobunone

1500

1501

1897

0.1

0.5

0.5

0.4

0.2

0.1

RI, MS

70

δ-Cadinene

1520

1515

1715

0.8

0.2

0.6

0.6

1.7

0.5

RI, MS

71

E-α-Bisabolene

1531

1526

1733

0.6

0.8

1.6

0.4

1.2

0.2

RI, MS

72

Isochavicol isobutyrate

1541

1538

2136

5.3

1.2

2.2

6.7

1.6

2.3

RI, MS

73

Germacrene B

1552

1555

1794

0.2

0.6

0.2

0.2

0.8

tr

RI, MS, Ref1

74

1,5-Epoxy-salvial-4(14)-ene

1561

1561

1903

0.1

0.7

0.4

0.5

0.4

3.6

RI, MS

75

Spathulenol

1572

1564

2091

0.5

1.2

1.4

0.3

0.6

-

RI, MS

76

Caryophyllene oxide

1578

1582

1943

tr

0.1

0.3

0.1

tr

0.5

RI, MS

77

Tridecanol

1580

1586

2034

-

tr

tr

tr

tr

6.4

RI, MS, Ref2

78

Viridiflorol

1590

1586

2071

0.1

0.9

0.3

0.5

0.2

 

RI, MS

79

Copaborneol

1592

1595

2142

0.5

0.8

0.3

1.5

0.1

1.4

RI, MS

80

Guaia-6,10(14)-diene-4β-ol

1610

1609

2119

1.1

2.5

2.1

6.6

0.5

0.9

RI, MS, Ref1

81

epi-Cubenol

1621

1623

2046

0.2

0.3

0.2

0.4

0.3

0.9

RI, MS

82

Cubenol

1630

1631

2001

0.5

0.2

0.2

0.3

tr

tr

RI, MS

83

τ-Muurolol

1633

1635

2156

0.5

0.7

0.3

0.6

0.7

1.4

RI, MS

84

α-Cadinol

1643

1644

2212

0.5

0.7

0.5

0.6

0.3

0.9

RI, MS

85

Isochavicol 2-methyl butyrate

1651

1654

2256

0.1

0.3

0.2

0.2

-

0.4

RI, MS

86

(Z)-α-Santalol

1669

1665

2306

0.1

0.4

0.1

0.1

0.1

-

RI, MS

87

Eudesma-4(15),7-dien-1β-ol

1671

1672

2346

0.1

0.3

0.2

0.1

0.5

1.3

RI, MS

88

(E,Z)-Farnesol

1685

1680

2313

tr

0.2

0.1

0.1

0.1

3.1

RI, MS

89

Heptadecane

1700

1699

1698

tr

0.3

0.3

0.1

0.1

0.5

RI, MS

90

Tetradecanoic acid

1761

1756

2651

tr

0.1

0.2

0.2

-

1.7

RI, MS, Ref2

91

Neophytadiene

1807

1806

1920

0.1

0.2

1.7

0.1

0.1

1.3

RI, MS, Ref1

92

Diisobutyl ester

1826

1826

2525

0.2

0.1

0.4

tr

tr

0.9

RI, MS, Ref2

93

6,10,14-Trimethylpentadecanone

1845

1842

2125

0.2

0.1

0.4

tr

0.1

1.8

RI, MS, Ref2

94

Hexadecanoic acid

1951

1956

2821

0.1

0.2

tr

tr

0.2

3.1

RI, MS, Ref1

95

Eicosane

2000

2000

1998

tr

0.1

tr

tr

0.2

18.6

RI, MS

96

(Z)-Phytol

2080

2085

2611

0.2

0.2

0.8

0.1

0.3

-

RI, MS

97

(E)-Phytol

2114

2119

2568

0.3

0.2

1.9

tr

0.1

-

RI, MS

98

Tricosane

2300

2302

2299

0.1

0.2

tr

tr

0.1

1.5

RI, MS

99

Pentacosane

2500

2498

2501

0.1

0.1

0.2

0.1

0,2

2.7

RI, MS

 

Total identification g/100g

   

90.9

93.7

93.6

98.7

95.3

90.1

 
 

Essential oil yield% (w/w)

   

0.2

0.04

0.03

0.09

0.12

0.02

 
 

Monoterpene hydrocarbons

   

61.6

52,0

54.5

58.5

57.1

1.5

 
 

Oxygenated monoterpenes

   

8.2

10.2

5.3

9.2

16.5

9.1

 
 

Sesquiterpene hydrocarbons

   

7.2

6.6

12.2

7.5

11.4

3.8

 
 

Oxygenated sesquiterpenes

   

4.4

9.6

7,0

12.3

4.3

14.4

 
 

Phenylpropanoids

   

5.4

2.2

2.5

7,0

1.9

3.3

 
 

Oxygenated diterpenes

   

0.5

0.4

2.7

0.1

0.4

-

 
 

Diterpenes hydrocarbons

   

0.1

0.2

1.7

0.1

0.1

1.3

 
 

Non-terpenic compounds

   

3.5

12.5

7.7

4,0

3.6

56.7

 

a Order of elution is given on apolar column (Rtx-1), b Retention indices of literature on the apolar column (lRIa) reported from König et al., 2001.,c Retention indices on the apolar Rtx-1 column (RIa), d Retention indices on the polar Rtx-Wax column (RIp), e Quantification was carried out using RFs relative to tridecane as internal standard, g/100 g: concentration expressed in g/100 g of essential oil are given on the apolar column except for components with identical RIa (concentrations are given on the polar column), tr = trace (<0,05 g/100 g), f RI: Retention Indices; MS: Mass Spectrometry in electronic impact mode; Ref1,: compounds identified from literature data König et al., 2001, Ref2,: compounds identified from literature data NIST Chemistry WebBook.

HS-SPME analysis

The volatiles emitted from the D. muricatus roots, leaves, stems, umbels, and flowers were investigated using HS–SPME under optimized parameters. The optimization of the HS–SPME sampling parameters was conducted using fresh plant material based on the sum of the total peak areas obtained using GC–FID. The maximum sum of the total peak area was acquired for an equilibrium and extraction temperature of 70°C, an equilibrium time of 60 min, and an extraction time of 30 min. The GC–RI and GC–MS analysis identified 78 components: 42 monoterpenes, 18 nonterpenic compounds, 16 sesquiterpenes, and two phenylpropanoids (Table 2). Identification of 74 components was conducted by comparing their EI–MS and retention indices with those in our laboratory-produced “Arômes” library, and four components were identified by comparing their EI–MS data and their apolar retention indices with those reported in the literature and in commercial libraries. Regarding the organ contribution to the aromatic plant fingerprint, it should be noted that the volatile constituents were more abundant in the leaves than in the other parts of the plant. Our analysis showed that the chemical composition of the HS fractions obtained from different organs was qualitatively similar but differed by the relative amounts of the main components. Relative to D. muricatus oil, the main volatiles emitted by plant were hydrocarbon compounds (60.7–82.2%) for all organs studied. More precisely, the sum of hydrocarbon monoterpenes (33.6%–64.1%) and hydrocarbon nonterpenic compounds (6.4%–25.5%) was higher than that of oxygenated compounds, which never accounted for more than 23.9 g/100 g. The main volatile components of roots were terpinolene (10.2%), bornyl acetate (9.7%), p-cymene (9.1%), α-pinene (8.7%), and undecane (7.2%). The relative amounts of terpinolene (0.4%–1.3%) and p-cymene (3.1%–3.4%) were lower in the aerial organs, and the main volatile emitted by leaves, flowers and umbels was limonene (30.6%, 19.1%, and 28.1%, respectively). In the stems, limonene (13.3%) was present in lower amounts than undecane (16.9%), which was identified as a major component. In addition, undecane was produced in appreciable amounts in leaves, flowers, and umbels (6.1%, 3.6%, and 7.4%, respectively). They were accompanied by α-pinene, which accounted for 8.1% in stems and always more than 13.1% in leaves, flowers and umbels. With these hydrocarbon compounds, we noted the occurrence of trans-sabinyl acetate, which had a relatively higher concentration in umbels (9.6%) than in the other aerial organs (2.6%–3.8%). The chemical differences observed between the essential oils and the volatile fractions extracted using HD and SPME, respectively, can be explained by the fact that the first technique is based on the liquid quasi-total extraction of plant volatiles, and the latter technique is controlled by a solid/gas equilibrium step. During hydrodistillation, the most volatile and water soluble compounds are lost in the gaseous phase and in the hydrolate, respectively, whereas, with HS extraction, it is the fiber affinity of each compound that monitors the sampling of the volatiles. As a consequence, it should be noted that 23 compounds (1a–1e, 5a, 8a, 9a, 13a, 14a, 19a, 20a, 21a, 22a, 22b, 27a, 27b, 29a, 38a, 47a, 51a, 54a, and 65a) were only identified in the volatile fractions extracted using HS–SPME.
Table 2

Chemical composition of D. muricatus volatile fractions extracted by HS-SPME

     

Separated organse

Componentsa

lRIab

RIac

Aerial parts

Stems

Leaves

Flowers

Umbels

Roots

1a

Heptane

700

700

2.6 ± 0.07

7.9 ± 0.28

1.3 ± 0.11

1.1 ± 0.15

0.3 ± 0.04

0.2 ± 0.01

1b

3-Methyl butanol

709

705

0.3 ± 0.01

0.7 ± 0.01

0.2 ± 0.01

0.4 ± 0.01

0.2 ± 0.01

0.1 ± 0.01

1c

3-Methyl-pentan-2-ol

754

760

0.4 ± 0.14

0.4 ± 0.01

0.2 ± 0.01

0.5 ± 0.09

0.4 ± 0.01

0.7 ± 0.01

1d

Hexanal

780

771

0.2 ± 0.01

0.4 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

0.3 ± 0.06

1.4 ± 0.07

1

Nonane

900

898

0.5 ± 0.07

0.5 ± 0.02

1.1 ± 0.22

0.4 ± 0.01

tr

0.1 ± 0.01

1e

Artemisiatriene

923

921

0.2 ± 0.01

-

-

0.3 ± 0.06

0.1 ± 0.01

-

2

α-Thujene

932

923

0.1 ± 0.01

-

0.1 ± 0.01

0.5 ± 0.04

0.1 ± 0.01

-

3

α-Pinene

936

931

13.2 ± 0.74

8.1 ± 0.36

16.1 ± 0.89

13.1 ± 0.97

15.5 ± 1.1

8.7 ± 0.14

4

Camphene

950

944

0.2 ± 0.01

tr

0.1 ± 0.01

0.3 ± 0.01

0.3 ± 0.08

0.4 ± 0.01

5a

Butyl butyrate

970

966

0.2 ± 0.01

-

0.2 ± 0.01

0.2 ± 0.01

0.2 ± 0.01

0.1 ± 0.01

6

Sabinene

973

967

2.9 ± 0.21

1.4 ± 0.14

2.3 ± 0.45

6.5 ± 0.33

1.5 ± 0.46

0.3 ± 0.01

7

β-Pinene

978

970

0.9 ± 0.06

0.7 ± 0.02

1.2 ± 0.56

1.1 ± 0.51

1.1 ± 0.13

1.6 ± 0.21

8

Myrcene

987

980

2.9 ± 0.13

1.5 ± 0.14

3.2 ± 0.21

2.9 ± 0.12

3.9 ± 0.66

0.1 ± 0.01

8a

Yomogi alcohol

991

981

0.4 ± 0.07

0.7 ± 0.01

0.4 ± 0.01

0.4 ± 0.01

0.4 ± 0.05

-

9

α-Phellandrene

1002

997

1.5 ± 0.13

-

3.1 ± 0.16

2 ± 0.29

1.1 ± 0.29

-

9a

3-Carene

1010

1005

0.1 ± 0.01

-

0.1 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

0.4 ± 0.01

10

α-Terpinene

1013

1008

0.8 ± 0.06

-

0.3 ± 0.01

2.8 ± 0.22

0.2 ± 0.01

0.1 ± 0.01

11

p-Cymene

1015

1012

3.2 ± 0.32

3.4 ± 0.12

3.1 ± 0.51

3.4 ± 0.51

3.2 ± 0.11

9.1 ± 0.76

12

Limonene

1025

1022

22.4 ± 1.28

13.3 ± 0.56

30.6 ± 0.99

19.1 ± 0.77

28.1 ± 0.82

6.9 ± 0.35

13

(Z)-β-Ocimene

1029

1025

0.2 ± 0.01

0.4 ± 0.01

0.1 ± 0.01

0.2 ± 0.02

0.1 ± 0.01

0.3 ± 0.01

13a

(E)-β-Ocimene

1041

1031

0.1 ± 0.01

0.1 ± 0.01

0.2 ± 0.02

0.2 ± 0.01

0.1 ± 0.01

0.3 ± 0.01

14

γ-Terpinene

1051

1049

3.2 ± 0.09

4.1 ± 0.54

2.5 ± 0.22

5.1 ± 0.55

1.3 ± 0.35

1.2 ± 0.01

14a

Octanol

1063

1052

0.3 ± 0.01

tr

0.6 ± 0.01

0.4 ± 0.08

0.3 ± 0.05

-

16

Nonan-2-one

1070

1073

0.6 ± 0.07

0.7 ± 0.02

0.5 ± 0.01

0.6 ± 0.08

0.6 ± 0.09

0.2 ± 0.01

17

p-Cymenene

1075

1077

0.3 ± 0.06

-

0.2 ± 0.01

0.4 ± 0.06

0.7 ± 0.03

3.1 ± 0.13

18

Terpinolene

1082

1079

0.7 ± 0.06

0.6 ± 0.01

0.9 ± 0.07

1.3 ± 0.23

0.4 ± 0.01

10.2 ± 0.86

19

Linalool

1083

1085

1.4 ± 0.08

3.2 ± 0.28

0.5 ± 0.01

1.1 ± 0.29

0.9 ± 0.1

0.2 ± 0.01

19a

α-Thujone

1089

1086

0.5 ± 0.04

1.8 ± 0.09

tr

0.5 ± 0.02

0.4 ± 0.02

0.1 ± 0.01

20

Undecane

1100

1100

8.9 ± 0.76

16.9 ± 0.89

6.1 ± 0.38

3.6 ± 0.14

7.4 ± 0.69

7.2 ± 0.26

20a

3-Octyl acetate

1113

1103

1.8 ± 0.12

0.7 ± 0.06

0.2 ± 0.01

0.3 ± 0.01

0.2 ± 0.01

0.2 ± 0.01

21a

Camphor

1123

1119

1.1 ± 0.07

2.9 ± 0.16

0.7 ± 0.01

0.6 ± 0.06

0.2 ± 0.01

0.5 ± 0.01

22

trans-Pinocarveol

1126

1120

0.4 ± 0.01

0.7 ± 0.01

0.3 ± 0.02

0.4 ± 0.01

0.6 ± 0.02

0.1 ± 0.01

22a

Citronellal

1129

1130

0.1 ± 0.01

tr

0.1 ± 0.01

0.1 ± 0.01

0.4 ± 0.05

-

22b

cis-Verbenol

1132

1132

0.1 ± 0.01

-

0.1 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

-

24

Pinocarvone

1137

1135

0.1 ± 0.01

-

0.1 ± 0.01

0.1 ± 0.01

0.2 ± 0.02

0.7 ± 0.01

25

Borneol

1150

1149

0.5 ± 0.08

0.9 ± 0.01

0.4 ± 0.01

0.3 ± 0.04

0.4 ± 0.01

-

26

Cryptone

1160

1159

0.5 ± 0.06

0.5 ± 0.01

0.5 ± 0.08

0.4 ± 0.01

0.7 ± 0.09

3.8 ± 0.11

27

Terpinene-4-ol

1164

1160

1.4 ± 0.18

2.1 ± 0.43

0.9 ± 0.06

1.8 ± 0.36

1.1 ± 0.15

0.1 ± 0.01

27a

Myrtenal

1172

1163

0.1 ± 0.01

tr

0.1 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

0.3 ± 0.02

27b

Estragole

1175

1169

1.1 ± 0.09

1.1 ± 0.58

1.3 ± 0.29

1.7 ± 0.12

0.6 ± 0.08

-

29

α-Terpineol

1176

1177

0.4 ± 0.05

0.5 ± 0.04

0.4 ± 0.08

0.4 ± 0.03

0.5 ± 0.01

0.2 ± 0.01

29a

Verbenone

1184

1178

0.3 ± 0.01

0.7 ± 0.01

0.1 ± 0.01

0.2 ± 0.01

0.1 ± 0.01

-

31

Decanal

1188

1185

0.1 ± 0.01

-

0.1 ± 0.01

0.1 ± 0.01

0.2 ± 0.01

-

33

Citronellol

1213

1211

1.1 ± 0.14

1.1 ± 0.22

1.1 ± 0.33

0.9 ± 0.06

1.5 ± 0.23

0.1 ± 0.01

34

Carvone

1214

1215

0.7 ± 0.07

1.1 ± 0.09

0.5 ± 0.01

0.6 ± 0.04

0.6 ± 0.02

0.1 ± 0.01

35

Pulegone

1215

1216

0.3 ± 0.01

0.8 ± 0.02

0.2 ± 0.01

0.2 ± 0.01

0.1 ± 0.01

-

37

Geraniol

1235

1235

0.2 ± 0.01

tr

0.1 ± 0.01

0.4 ± 0.02

0.1 ± 0.01

0.8 ± 0.05

38

trans-Myrtanol

1240

1236

0.1 ± 0.01

0.1 ± 0.01

tr

0.1 ± 0.01

0.3 ± 0.01

-

38a

Geranial

1244

1239

0.1 ± 0.01

tr

0.1 ± 0.01

0.1 ± 0.01

tr

-

39

cis-Chrysanthenyl acetate

1253

1242

0.1 ± 0.01

tr

0.1 ± 0.01

tr

0.1 ± 0.01

-

42

Bornyl acetate

1270

1266

0.6 ± 0.05

1.2 ± 0.11

0.4 ± 0.05

0.5 ± 0.06

0.6 ± 0.04

9.7 ± 0.55

43

Undecan-2-one

1273

1270

0.6 ± 0.08

0.8 ± 0.04

0.6 ± 0.08

0.4 ± 0.03

0.5 ± 0.01

0.3 ± 0.01

44

trans-Sabinyl acetate

1278

1271

5.1 ± 0.47

3.8 ± 0.26

2.6 ± 0.12

3.5 ± 0.38

9.6 ± 0.53

 

47a

Neryl acetate

1342

1335

2.0 ± 0.31

2.4 ± 0.36

3.4 ± 0.65

1.3 ± 0.35

0.9 ± 0.1

0.3 ± 0.01

48

δ-Elemene

1340

1337

0.3 ± 0.02

0.7 ± 0.06

0.3 ± 0.05

0.1 ± 0.01

tr

0.1 ± 0.01

49

Geranyl acetate

1362

1360

0.1 ± 0.01

tr

tr

0.2 ± 0.01

tr

0.2 ± 0.01

50

Undecanol

1363

1365

0.1 ± 0.01

tr

tr

tr

tr

1.9 ± 0.01

51

α-Copaene

1379

1377

0.7 ± 0.01

1.1 ± 0.12

0.4 ± 0.02

0.6 ± 0.03

0.9 ± 0.08

0.4 ± 0.01

51a

Daucene

1380

1379

0.5 ± 0.02

0.9 ± 0.08

0.1 ± 0.01

0.2 ± 0.01

0.7 ± 0.01

0.7 ± 0.06

54

Dodecanal

1389

1395

0.2 ± 0.01

0.3 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

1.3 ± 0.01

54a

Tetradecane

1400

1399

0.1 ± 0.01

0.2 ± 0.02

0.1 ± 0.01

0.1 ± 0.01

tr

-

56

trans-Caryophyllene

1424

1422

2.3 ± 0.23

1.4 ± 0.13

3.1 ± 0.25

3.8 ± 0.26

1.2 ± 0.15

1.9 ± 0.18

58

β-Copaene

1430

1430

0.3 ± 0.02

0.4 ± 0.01

0.6 ± 0.05

0.3 ± 0.01

0.3 ± 0.01

0.4 ± 0.01

59

α-Humulene

1455

1450

0.4 ± 0.05

-

0.1 ± 0.01

0.9 ± 0.08

0.1 ± 0.01

0.1 ± 0.01

61

Dodecanol

1472

1468

tr

tr

tr

tr

tr

3.4 ± 0.28

62

γ-Muurolene

1473

1471

1.3 ± 0.13

0.5 ± 0.01

0.6 ± 0.01

1.5 ± 0.42

1.9 ± 0.21

4.3 ± 0.16

63

Germacrene D

1479

1476

0.4 ± 0.04

0.5 ± 0.06

0.2 ± 0.01

0.4 ± 0.02

0.3 ± 0.01

0.2 ± 0.01

64

trans-β-Bergamotene

1480

1475

tr

tr

tr

tr

tr

0.5 ± 0.03

65

6-epi-Shyobunone

1481

1480

0.1 ± 0.01

tr

0.1 ± 0.01

0.2 ± 0.01

0.2 ± 0.01

-

65a

β-Selinene

1486

1481

0.2 ± 0.01

0.2 ± 0.01

0.2 ± 0.02

0.1 ± 0.01

0.2 ± 0.03

0.5 ± 0.02

69

Shyobunone

1500

1501

0.1 ± 0.01

tr

0.1 ± 0.01

0.1 ± 0.01

0.1 ± 0.01

0.7 ± 0.01

70

δ-Cadinene

1520

1515

0.6 ± 0.04

0.5 ± 0.01

0.3 ± 0.04

0.1 ± 0.01

1.3 ± 0.16

0.9 ± 0.07

71

(E)-α-Bisabolene

1531

1526

1.1 ± 0.31

0.5 ± 0.02

1.4 ± 0.12

0.9 ± 0.1

1 ± 0.45

0.4 ± 0.01

72

Isochavicol isobutyrate

1541

1538

0.3 ± 0.05

tr

0.3 ± 0.01

0.9 ± 0.06

0.1 ± 0.01

0.1 ± 0.1

76

Caryophyllene oxide

1578

1582

0.2 ± 0.01

-

0.1 ± 0.01

0.4 ± 0.01

0.1 ± 0.01

0.7 ± 0.01

77

Tridecanol

1580

1586

tr

tr

tr

tr

tr

1.1 ± 0.07

87

Eudesma-4(15),7-dien-1β-ol

1671

1672

tr

-

tr

tr

tr

0.6 ± 0.01

89

Heptadecane

1700

1699

0.4 ± 0.13

-

1.3 ± 0.65

0.2 ± 0.01

0.2 ± 0.01

-

 

Total identification (%)

  

97.8

95.4

99.1

94.3

97.6

90.6

 

GC-FID Total area 105

  

103

22

154

108

107

68

 

Monoterpene hydrocarbons

  

52.9

33.6

64.1

59.3

57.8

42.8

 

Oxygenated monoterpenes

  

20.6

25.6

14.4

16

20.5

17.6

 

Sesquiterpene hydrocarbons

  

8.1

5.8

7.2

8.7

7.2

10.4

 

Oxygenated sesquiterpenes

  

0.4

-

0.3

0.7

0.4

2.0

 

Phenylpropanoids

  

0.3

-

0.3

0.9

0.1

0.1

 

Non-terpenic compounds

  

15.5

30.4

12.8

8.7

11.6

17.7

a Order of elution is given on apolar column (Rtx-1). Numbers correspond to those in Table 1. The volatile components identified exclusively from the HS-fractions were affected by a letter, b Retention indices of literature on the apolar column (lRIa) reported from König et al., 2001., c Retention indices on the apolar Rtx-1 column (RIa), d Percentages (means of three analyses) obtained by GC-FID (on RTX-1: apolar column) under optimized HS-SPME parameters: temperature: 70°C, equilibrium time: 120 min; extraction time: 30 min.

Antimicrobial activity (assay disk)

Preliminary screening of the antimicrobial activity in vitro of the essential oils from D. muricatus species against nine pathogenic microorganisms were studied using the filter paper disc agar-diffusion technique. The results showed variation in the antimicrobial properties of the plant essential oil (Table 3). The essential oil showed strong activity (inhibition zone >20 mm), moderate activity (inhibition zone <20–12 mm), and no inhibition (zone <12 mm). The highest activity (diameter of inhibition zone 22 mm) was demonstrated against S. aureus by the essential oil of the root, while the lowest (diameter of inhibition zone 6 mm) was demonstrated against E. coli by oil from the aerial parts. Other hand, C. albicans, B. cereus and L. monocytogenes were also prone to growth inhibition with diameter zones of inhibition ranging from 12 to 16 mm. Rest of the bacterial strains (B. subtilis, E. faecalis, P. aeruginosa, K. pneumonia and E. coli) showed no inhibition, with diameter of zones of inhibition ranging from 8 to 10 mm (Table 3).
Table 3

Antimicrobial activity of D. muricatus essential oil

Microorganisms

Disc diffusion assay (mm)

MIC (μg/ml)

 

Roots

Aerial parts

Roots

Aerial parts

Gram-positive bacterium

    

B. subtilis

9

8

> 6000

> 6000

L. monocytogenes

14

13

65

250

B. cereus

15

12

65

250

S. aureus

22

10

8

> 6000

P. aeruginosa

9

10

> 6000

> 6000

E. faecalis

10

8

> 6000

> 6000

Gram-negative bacterium

    

K. pneumoniae

9

8

> 6000

> 6000

E. coli

8

6

> 6000

> 6000

Yeast

    

C. albicans

12

16

95

45

Minimum inhibitory concentrations (MIC)

The in-vitro antibacterial activities of essential oil from the roots and aerial parts of D. muricatus against the employed bacteria were assessed qualitatively and quantitatively by the presence or absence of inhibition zones. The noted antibacterial and antifungal effects of the two are presented in Table 3. In general, the roots oil showed higher activity against bacteria than oil of aerial parts. The most prominent inhibitory action of roots oil was observed against S. aureus with a MIC of 0.8 μg/ml. However, B. cereus and L. monocytogenes showed moderate activity with MIC values of 65 μg/ml. As for the antifungal effect, the aerial parts oil was found to be effective against the pathogenic yeast C. albicans (MIC = 45 μg/ml) and an average activity antimicrobial on the B. cereus and L. monocytogenes with a MIC of 250 μg/ml. It should be noted that the highest tested concentration (6000 μg/ml) of had no effect on other growth of microorganisms. Various chemical compounds isolated by hydrodistillation of oils from D. muricatus have direct activity against many species of bacteria, such as terpenes and a variety of aliphatic hydrocarbons (alcohols, aldehydes and ketones). The lipophilic character of their hydrocarbon skeleton and the hydrophilic character of their functional groups are of main importance in the antimicrobial action of essential oils components. Therefore, a rank of activity has been proposed as follows: phenols > aldehydes > ketones > alcohols > esters > hydrocarbons [28]. The activity of the roots oil could be explained at least partially by its content of undecan-2-one (10.2%). This ketone was previously proved to have antimicrobial and nematicidal activity [29, 30]. The higher activity of the roots oil compared to the aerial parts oil could be attributed to this fact. Another major class of this oil, aliphatic alcohols was, likewise, previously reported as an antimicrobial compound and was reported to possess strong to moderate activities against several bacteria [31].

Conclusion

Volatiles isolated from separated organs of D. muricatus by HS–SPME and hydrodistillation were investigated using GC–RI and GC–MS. Concerning the essential oils, oil from D. muricatus roots was mainly composed of oxygenated compounds, while oil from aerial parts (i.e., the leaves, stems, flowers, and umbels) was dominated by hydrocarbon compounds. Moreover, the study of the volatiles sampled by HS–SPME showed that the chemical composition of the HS fractions obtained from different organs was qualitatively similar but differed by the relative concentrations of the main components. It is interesting to note that the sample preparation method impacted quantitatively on the GC profile of D. muricatus volatiles. The antimicrobial properties of D. muricatus essential oils tested on nine microorganisms species showed that oil from roots was active against S. aureus, while essential oil obtained from aerial parts was active against the yeast C. albicans.

Experimental

Plant material and oil isolation

Separated organs (stems, leaves, flowers, umbels and roots) from D. muricatus were collected in Bensekrane forest area (North West of Tlemcen, Algeria) [287 m, 35 °07′N 1 °22′O] on September 2009. Voucher specimens were deposited in the herbarium of the Tlemcen University Botanical Laboratory (Voucher number: UBL 128.09). A portion of each organ was stored at 4°C for eventual further studies. The oils were isolated by hydrodistillation (400–450 g of plant per sample) for 6 h using a Clevenger-type apparatus [32] according to the European Pharmacopoeia and yielded 0.02% for roots and 0.03-0.12% for aerial parts w/w of oil.

HS-SPME conditions

The single organs of D. muricatus (stems, leaves, flowers, umbels and roots separately) were cut roughly with scissors (1–2 cm long) before subjection to HS-SPME. The SPME device (Supelco) coated with divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS, 30 μm) was used for extraction of the plant volatiles. Optimization of conditions was carried out using fresh organs of the plant (1 g in a 20 mL vial) and based on the number and the sum of total peak areas measured on GC-FID. Temperature, equilibration time and extraction time were selected after nine experiments combining four temperatures (30, 50, 70 and 90°C), four equilibration times (20, 40, 60 and 80 min) and three extraction times (15, 30 and 45 min). After sampling, SPME fibre was inserted into the GC and GC-MS injection ports for desorption of volatile components (5 min), both using the splitless injection mode. Before sampling, each fibre was reconditioned for 5 min in the GC injection port at 260°C. HS-SPME and subsequent analyses were performed in triplicate. The coefficient of variation (1.6% < CV < 17.8%) calculated on the basis of total area obtained from the FID-signal for the samples indicated that the HS-SPME method produced reliable results.

Gas chromatography

GC analyses were carried out using a Perkin–Elmer (Waltham, MA, USA) Autosystem XL GC apparatus equipped with a dual flame ionization detection system and a fused-silica capillary columns (60 m x 0.22 mm I.D., film thickness 0.25 μm), Rtx-1 (polydimethylsiloxane). The oven temperature was programmed from 60°C to 230°C at 2°C/min and then held isothermally at 230°C for 35 min. Injector and detector temperatures were maintained at 280°C. Samples were injected in the split mode (1/50), using helium as the carrier gas (1 mL/min); the injection volume was 0.2 μL. Retention indices (RI) of the compounds were determined from a software from Perkin-Elmer. Component relative concentrations were calculated based on GC peak areas without using correction factors.

Gas chromatography–mass spectrometry

Samples were analyzed with a Perkin–Elmer Turbo mass detector (quadrupole), coupled to a Perkin–Elmer Autosystem XL, equipped with the fused-silica capillary columns Rtx-1 and Rtx-Wax (ion source temperature 150°C; energy ionization 70 eV). EI mass spectra were acquired over the mass range 35–350 Da (scan time: 1 s). Other GC conditions were the same as described under GC except split 1/80.

Component identification

Identification of the components was based (i) on the comparison of their GC retention indices (RI) on non polar and polar columns, determined relative to the retention time of a series of n-alkanes with linear interpolation, with those of authentic compounds or literature data [33, 34]; and (ii) on computer matching with commercial mass spectral libraries [3335] and comparison of spectra with those of our personal library.

Component quantification

Quantification of essential oil components was expressed using relative concentration in g/100 g of essential oil. The procedure included the calcul of FID response factors (RFs) relative to an internal standard. We carried out a methodology reported in the literature [36] and improved in our laboratory [37]. The application of this analytical procedure allowed the determination of the oil component relative concentrations expressed in g/100 g of essential oil. Relative amounts of individual components obtained during HS-SPME experiments, were calculated on the basis of their GC peak areas on the Rtx-1 capillary column, without FID response factor correction.

Bacterial and yeast strains and media

The bacterial strains used in this study, i.e. Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Enterococcus faecalis, Listeria monocytogenes, Bacillus cereus (Gram positive), Escherichia coli and Klebsiella pneumoniae (gram negative) were isolated at the Medical Reanimation Department of the Hospital University Center of Tlemcen in Algeria. The yeast Candida albicans was isolated at the Dermatology Department of the same hospital. Bacterial strains preserved in nutrient agar at 4°C, were revivified in nutrient solution and incubated at 37 ± 1°C during 18 to 24 h. 0.1 mL of each culture was added to 10 mL BHIB (Brain Heart Infusion Broth, pronadisa Hispanalab). C. albicans preserved at 4°C in the Sabouraud agar supplemented with chloramphenicol was revivified in nutrient solution and incubated at 30 ± 1°C during 24 to 48 h. 0.1 mL of each culture was added to 10 mL sterile physiological water. For antimicrobial assay, bacterial strains were grown on Mueller-Hinton Agar (MHA, Pronadisa Hispanalab) while C. albicans was grown on Sabouraud Dextrose Agar + chloramphenicol (SDA, Merck). Bacterial and yeast inoculate reached microbial densities in the range 106 to 107 cfu/mL.

Antimicrobial activity

Paper-disc diffusion method

Antibacterial activities of essential oil from root and all aerial parts of the plant were assessed using the paper disk agar diffusion method according to Rios [38]. Absorbent disks (Whatman disk 6-mm diameter) were impregnated with 20 μl of oil, to concentration of 5 mg mL-1, and then placed on the surface of inoculated plates (90 mm) and incubated at 37°C for 24 h. Negative controls were prepared using a disk impregnated with the same solvent as that used to dissolve the plant oils. Antimicrobial activity was assessed by measuring the inhibition zone. All the tests were performed in triplicate.

Dilution-agar method

A dilution agar method was used to determine the Minimum Inhibitory Concentrations (MIC). Stock solutions were obtained by dissolving extracts in dimethylsulfoxide (DMSO 1%). Serial dilutions were made to obtain concentrations ranging from 0 to 100 μg mL-1 of the essential oil. Each mixture was added to Mueller–Hinton agar for bacteria [39, 40]. The Petri dishes contained a sterile solution of DMSO and the culture medium, respectively. After incubation at 37°C for 24 h for bacteria and at 30°C for 48 h for the yeast. The experiments were performed in triplicate.

Declarations

Acknowledgments

The authors are grateful to Prof. M. Bouazza (Botanical Laboratory, Biology Department, Aboubekr Belkaïd University) for the identification of the vegetable matter, and are indebted to the Agence Universitaire de la Francophonie (AUF) for providing a research grand of N.D., and the Ministère des Affaires Etrangères et Européennes throughout the research program "Partenariat Hubert Curien Tassili".

Authors’ Affiliations

(1)
Laboratoire des Substances Naturelles et Bioactives, Université de Tlemcen
(2)
UMR CNRS 6134, Laboratoire Chimie des Produits Naturels, Campus Grimaldi, Université de Corse

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