Nematicidal Activity of ( E , E )-2,4-Decadienal and ( E )-2-Decenal from Ailanthus altissima against Meloidogyne javanica

Share Embed


Descrição do Produto

Subscriber access provided by Università di Cagliari

Article

Nematicidal Activity of (E,E)-2,4-decadienal and (E)-2-decenal from Ailanthus altissima against Meloidogyne javanica Pierluigi Caboni, Nikoletta G. Ntalli, Nadhem Aissani, Ivana Cavoski, and Alberto Angioni J. Agric. Food Chem., Just Accepted Manuscript • DOI: 10.1021/jf2044586 • Publication Date (Web): 05 Jan 2012 Downloaded from http://pubs.acs.org on January 17, 2012

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a free service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are accessible to all readers and citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

Journal of Agricultural and Food Chemistry is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 27

Journal of Agricultural and Food Chemistry

1

Nematicidal Activity of (E,E)-2,4-decadienal and (E)-

2

2-decenal from Ailanthus altissima against

3

Meloidogyne javanica

4

5

Pierluigi Caboni*,§, Nikoletta G. Ntalli§, Nadhem Aissani§, Ivana Cavoski§, Alberto

6

Angioni§

7 8 9

§

Department of Pharmaceutical Chemistry and Technology, University of Cagliari,

via Ospedale 72, 09124 Cagliari, Italy

10 11 12 13 14

* To whom correspondence should be addressed

15

Department of Pharmaceutical Chemistry and Technology, Via Ospedale 72, 09124

16

Cagliari (Italy)

17

Tel. +390706758617. Fax +390706758612.

18

e-mail:[email protected]

19

20

Running title: Nematicidal activity of Ailanthus altissima methanol extracts

1

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 2 of 27

21

Abstract

22

Methanol extracts of various plant parts of Ailanthus altissima were tested against the

23

root knot nematode Meloidogyne javanica. Extracts of bark (ABE), wood (AWE),

24

roots (ARE), and leaves (ALE) from A. altissima were investigated against freshly

25

hatched second stage juveniles (J2). AWE was the most active extract with EC50/3d of

26

58.9 mg/L while the ALE, ARE and ABE did not show nematicidal activity. The

27

chemical composition of the extracts of A. altissima was determined by gas

28

chromatography mass spectrometry and (E,E)-2,4-decadienal, (E)-2-undecenal, (E)-2-

29

decenal, hexanal, nonanal and furfural were the most prominent constituents. (E,E)-

30

2,4-decadienal and (E)-2-decenal, furfural showed the highest nematicidal activity

31

against M. javanica EC50/1d = 11.7, 20.43 and 21.79 mg/L respectively, while the

32

other compounds were inactive at the concentrations tested. The results obtained

33

showed that AWE and its constituents (E,E)-2,4-decadienal and (E)-2-decenal could

34

be considered as a potent botanical nematicidal agents.

35

36

KEYWORDS: GC-MS, tree of heaven, unsaturated aldehydes, Meloidogyne

37

javanica, botanical pesticide, reactive carbonyl species, (E,E)-2,4-decadienal,(E)-2-

38

decenal.

2

ACS Paragon Plus Environment

Page 3 of 27

Journal of Agricultural and Food Chemistry

39

INTRODUCTION

40

Crops infestation by root knot nematodes (RKN; Meloidogyne spp.) causes annually

41

US$ 70 billion of crop losses in fruit and vegetables production (1). Among potential

42

strategies to control these pests natural nematicides isolated from plants or

43

microorganisms are successfully used as bio-control agents to reduce non-target

44

exposure to hazardous pesticides and to face resistance development (2, 3). The

45

control of nematodes on cucumber, tomato, carrot has been done primarily by

46

fumigants such us metam sodium and 1,3-dichloropropene or by the means of a

47

biological control using bacteria such us Bacillus firmus and Bacillus chitinosporus,

48

or by using botanical extracts such us sesame stalk or oil, neem cake and crab shell

49

meal. Nematicidal application is performed before planting or during crop growth.

50

The pressure to find viable alternatives to the soil fumigant methyl bromide,

51

withdrawn in 2005 according to the Montreal Protocol on Substances that Deplete the

52

Ozone Layer, has been intensified in the recent years.

53

Plant secondary metabolites that have no apparent role in lie processes of plant

54

structure play an important role in plant-insects interactions (4) and therefore such

55

compounds called allelochemicals have insecticidal, hormonal, and antifeedant

56

activities against pests (2). Reynolds reported that M. incognita and other generalists

57

nematodes with a wide host range may rely almost exclusively on general plant clues

58

with right blend and concentration of semiochemicals (1). Plants may use some

59

known nematicidal cues like 2-undecanone, furfural, benzaldehyde, thymol, limonene,

60

neral, geranial and carvacrol for defending themselves against the attacker in the

61

underground (5-13). On the other hand, some nematodes can be used by plants for the

62

indirect defense against plant herbivores (14). Another role of secondary metabolites 3

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 4 of 27

63

is that of allelopathy, the inhibition of one plant’s growth by another through the

64

production and release of toxic chemicals into the environment (14). Unsaturated

65

aldehydes are known to be formed in large amounts in plant tissues in responses to

66

wounding and the subsequent action of the lipoxygenase enzyme system (LOX)

67

involving lipid oxidation (15). According to Wenke belowground volatiles produced

68

by plants facilitate interactions between roots and soil organisms (16) while

69

Hildebrand (17) suggested that LOX-mediated products including aliphatic aldehydes,

70

ketones, and alcohols are involved in plant defense.

71

The nematode cuticle is flexible and the exoskeleton resilient allowing locomotion,

72

protection and permitting growth by molting. The cuticle is composed of cross-linked

73

collagens, insoluble proteins called cuticlins, glycoprotein and lipids. The cuticle

74

collagens are encoded by a large gene family and mutation of individuals genes can

75

result in a range of defects from abnormal morphology, to larval deaths confirming a

76

crucial and essential role of the cuticle structures. Activated small molecular weights

77

carbonyls are an important class of intermediates known as reactive carbonyl species.

78

(RCS). In our search for new naturally occurring compounds we found that 2-

79

undecanone constituent of the methanol extract of Ruta chalepensis and furfural from

80

Melia azedarach exhibited strong nematicidal activity against J2 larvae of

81

Meloidogyne incognita and M. javanica (5, 6). These compounds are by products of

82

cellular metabolism including lipid peroxidation, glycation and are activated by

83

α,β,γ,δ insaturation and/or β oxo-substitution. Among the damage caused by RCS is

84

DNA damage, proteosome degradation as well as cellular and extracellular protein

85

alteration. The latter has been recently linked to skin and collagen deterioration (18).

86

RCS especially mono and di-carbonyl compounds can react with proteins to form a 4

ACS Paragon Plus Environment

Page 5 of 27

Journal of Agricultural and Food Chemistry

87

variety of adducts through a Maillard reaction. These compounds are known as

88

advanced glycation end-products.

89

A. altissima, commonly known as “tree of heaven" is a deciduous tree of the

90

Simaroubaceae family. When the leaves and flowers are crushed emit a foul smelling

91

odour. A. altissima is native to northeast and central China and was introduced in

92

Europe as street tree at the end of the 18th century. A. altissima grows rapidly and is

93

capable of reaching heights of 10-15 meters and for this reason it has become an

94

invasive species capable to colonise disturbed areas. Characteristics of this plant

95

include: the versatility of the reproductive methods, the tolerance to unfavourable

96

conditions and the potential presence of allelochemicals (14). The tree of heaven was

97

been already used in traditional medicine in many parts of Asia including China,

98

while the bark and leaves are being used for their bitter-tonic, astringent, vermifuge

99

and antitumoral properties (19). Different phytochemical studies reported the presence

100

in the plant of chemical compounds such us quassinoids, alkaloids, lipids and fatty

101

acids, volatile and phenolic compounds, flavonoids and coumarins (19). Kraus et al.

102

reported that the ailanthone extracted with methanol from A. altissima seeds turned

103

out to be a potent antifeedant and insect growth regulator (20).

104

In this work we studied the composition of methanol extracts from various part of A.

105

altissima by GC/MS. We also investigated the nematicidal activity of these extracts

106

and their components against root knot nematode M. javanica to find potential

107

botanical alternatives to the currently used synthetic nematicidal agents or model

108

compounds for the development of chemically synthesized derivatives with enhanced

109

activity and environmental compatibility.

5

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 6 of 27

110

MATERIALS AND METHODS

111

Chemicals. Standards of (E,E)-2,4-decadienal, (E)-2-undecenal, (E)-2-decenal, (E)-2-

112

octenal, nonanal, hexanal, acetic acid, furfural, 2,3-butanediol, hexanoic acid, 5-

113

hydroxymethylfurfural, heptanal of purity greater than 98%, as well as Tween 20 and

114

dimethylsulfoxide were obtained from Sigma-Aldrich (Milano, Italy). Methanol and

115

water were HPLC grade.

116

Extraction and Chemical Characterisation. Plant materials. Leaves, bark, wood of

117

A. altissima were collected before flowering in April 2011 at Cagliari (Italy), and

118

were dried in the absence of light at room temperature. Then they were sealed in

119

paper bags and stored at room temperature kept in the dark, until use. Voucher

120

specimens were deposited in the Department of Pharmaceutical Chemistry and

121

Technology, University of Cagliari for species identification.

122

A. altissima Methanol Extracts. Dried leaves, bark, roots and wood plant parts (100 g)

123

were grinded and extracted with methanol (1:10 w/v) in a sonicator apparatus for 15

124

min, filtered through a Whatman no. 40, and centrifuged for 15 min at 13000 rpm.

125

The extract was analysed for components identification by means of GC-MS.

126

GC-MS Analysis. The chromatographic separation and identification of main

127

components of methanol extracts of Ailanthus altissima was performed on a Trace GC

128

Ultra Gas Chromatograph (Thermo Finnigan, MA, USA) coupled with a Trace DSQ

129

mass spectrometry detector, a split-splitless injector, and an Xcalibur MS platform.

130

The column was a CP-WAX 57CB from Varian (60 m, 0.25 mm i.d. and 0.25 µm film

131

thickness; Varian Inc., U.S.A.). The injector and the transfer line were at 200 °C. The

132

oven temperature was programmed as follows: 50 °C (hold 1 min) then raised to 220

133

°C (3 °C/min), and isothermally hold for 13 min. Helium was the carrier gas at 6

ACS Paragon Plus Environment

Page 7 of 27

Journal of Agricultural and Food Chemistry

134

constant flow-rate of 1 mL/min; 1 µL of each sample was injected in the splitless

135

mode (60 s). Mass spectrometry acquisition was carried out using the continuous (EI

136

positive) scanning mode from 40 to 500 amu. A. altissima methanol extracts

137

components were identified by a) comparison of their relative retention times and

138

mass fragmentation with those of authentic standards; b) computer matching against a

139

NIST98 commercial library. Quantitative analysis of each component was carried out

140

with the external standard method.

141

Effect of A. altissima extracts on J2 motility. Effects of ALE (Ailanthus Leaves

142

Extract), ABE (Ailanthus Bark Extract) and AWE (Ailanthus Wood Extract) on M.

143

javanica J2 motility were tested at the test concentration range of 15.6 to 250 mg/L for

144

EC50s calculation. Pure compounds contained in the extracts were tested individually

145

against M. javanica at the concentration range of 1 to 50 mg/L for EC50s calculation.

146

The compounds used for the paralysis experiment were: (E,E)-2,4-decadienal, (E)-2-

147

decenal, (E)-2-undecenal, (E)-2-decenal, nonanal, heptanal, hexanal, furfural, and 5-

148

hydroxymethylfurfural. Stock solutions were prepared in methanol to overcome

149

insolubility, whereas tween 90 in distilled water was used for further dilutions. Final

150

concentrations of methanol in each well never exceeded 1% v/v, since preliminary

151

experiments showed that this concentration was not toxic to nematodes. Distilled

152

water as well as a mixture of water and tween (0.3% v/v) (carrier control) served as

153

controls. In all cases, working solutions were prepared containing double the test

154

concentration and mixed in CellstarR 96-well cell culture plates (Greiner bio-one) at a

155

ratio of 1:1 v/v with suspensions of 15 J2 added to each well. Multiwell plates were

156

covered to prevent evaporation and maintained in the dark at 28◦C.

7

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 8 of 27

157

Juveniles were obtained by an Italian population of M. javanica reared for two months

158

on tomato (Solanum lycopersicum) in a glasshouse at 25+2 °C. Juveniles were

159

observed with the aid of an inverted microscope (Zeiss, 3951, West Germany) at 10×

160

after 1, 24 and 72 h and were ranked into two distinct categories: motile or paralysed.

161

Moreover, at that point, nematodes were moved to plain water after washing in tap

162

water through a 20-µm pore screen to remove the excess of extracts. Numbers of

163

motile and paralysed J2 were assessed by pricking the juvenile body with a needle and

164

they were counted.

165

Statistical Analysis. Treatments of paralysis experiments were replicated five times,

166

and each experiment was performed twice. The percentages of paralysed J2 in the

167

microwell assays were corrected by elimination of the natural death/paralysis in the

168

water

169

corrected%=[(mortality% in treatment-mortality % in control)/(100 - mortality % in

170

control)}] 100, and they were analyzed (ANOVA) combined over time. Because

171

ANOVA indicated no significant treatment by time interaction, means were averaged

172

over experiments. Corrected percentages of paralysed J2 treated with A. altissima

173

extracts or pure compounds were subjected to nonlinear regression analysis using the

174

log-logistic equation proposed by Seefeldt et al. (22): Y = C + (D - C)/{1 + exp[b

175

(log(x) - log(EC50)]}, where C = the lower limit, D = the upper limit, b = the slope at

176

the EC50, and EC50 = A. altissima extract or pure compound concentration required for

177

50% death/paralysis of nematodes after elimination of the control (natural

178

death/paralysis). In the regression equation, the A. altissima extract or pure compound

179

concentration (% w/v) was the independent variable (x) and the paralysed J2

180

(percentage increase over water control) was the dependent variable (y). The mean

control

according

to

the

Schneider

Orelli

formula

(21),

8

ACS Paragon Plus Environment

Page 9 of 27

Journal of Agricultural and Food Chemistry

181

value of the five replicates per test concentration and immersion period was used to

182

calculate the EC50 value.

183

Scanning Electronic Microscopy Analysis. The physical mechanism that (E,E)-2,4-

184

decacadienal and furfural used to interact with the external nematode cuticle was

185

observed by SEM in the environmental mode (1-20 Torr). Freshly hatched nematodes

186

were treated for 24 hours by immersion in a 100 µL solution containing 100 mg/L of

187

the test compounds. Thereafter, a topographic visualization by using a FEI Quanta

188

200 microscope (FEI) was performed.

189

9

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 10 of 27

190

RESULTS AND DISCUSSION

191

Mass spectrometry coupled to gas chromatography is a useful analytical platform for

192

the chemical characterisation of plant extracts because it allows the identification of a

193

large number of plant metabolites. A major disadvantage of this technique is that

194

analytes used must be derivatized to improve the volatility to the injection port. In this

195

work Ailanthus altissima methanol extracts were directly injected in the GC/MS

196

neither employing derivatization nor any purification steps. Using a CP-WAX 57CB

197

Carbowax column we were able to separate polar and medium polar plant secondary

198

metabolites such us (E,E)-2,4-decadienal, (E)-2-undecenal, (E)-2-decenal, (E)-2-

199

decenal, hexanal, nonanal, acetic acid, furfural, 2,3-butanediol, hexanoic acid, 5-

200

hydroxymethylfurfural (Table 1). We also tried to chemically characterize the

201

methanol extract by LCMS TOF but aldehydes were not detected due to their

202

volatility and low ionization efficiency during atmospheric pressure ionization.

203

Among unsaturated aldehydes identified in A. altissima extracts, (E,E)-2,4-decadienal,

204

(E)-2-decenal and furfural were the most active against J2 with EC50/1d of 11.70 and

205

20.43 mg/L respectively, while (E)-2-octenal, nonanal, heptanal and hexanal did not

206

provoke paralysis on J2s (Table 2). Interestingly, 1 hour post J2 immersion in test

207

solutions EC50s were calculated even lower (7.5 and 11.75 mg/L for (E,E)-2,4-

208

decadienal and (E)-2-decenal), but this activity was characterised as nematostatic

209

rather than nematicidal since to some extend J2 regained their movement later.

210

Moreover, no fumigant activity of plant methanol extracts or pure compounds was

211

detected. The activity of (E,E)-2,4-decadienal, (E)-2-decenal against M. javanica is

212

rather high if compared with the nematicidal activity of fosthiazate (EC50/1d=15.9

213

mg/L). 10

ACS Paragon Plus Environment

Page 11 of 27

Journal of Agricultural and Food Chemistry

214

Αccording to the GC-MS analysis (Figure 1), AWE afforded (E,E)-2,4-decadienal,

215

(E)-2-decenal, hexanal, nonanal, acetic acid, furfural, 2,3-butanediol, 2-decenal, 2-

216

undecenal, hexanoic acid, and 5-hydroxymethylfurfural (Table 1), while ALE, ARE

217

and ABE afforded nonanal, acetic and hexanoic acid and 2,3-dihydro-3,5-dihydroxy-

218

6-methyl-4H-pyran-4-one. As a result of the GC-MS analysis fourteen plant

219

metabolites, accounting for 82.6 % of the methanol extract were identified. Not taking

220

into account plant compound bioavailability nor synergetic effect when AWE was

221

tested against M. javanica a clear dose response relationship was established and

222

significant paralysis of J2 was evident after three days of exposure with an EC50/3d

223

value calculated at 58.9 mg/L (Table 3). This value is rather low considering the

224

activities of Ruta chalepensis methanol extracts against M. incognita exhibiting an

225

EC50 value of 1001 mg/L after 1 day of J2 immersion in test solutions (5) as well as

226

Plantago lanceolata with an EC50 of 43.7% after 2 days of immersion (22).

227

This is the first report of the irreversible nematicidal activity of unsaturated aldehydes

228

as constituents of A. altissima against M. javanica. According to our results (E,E)-2,4-

229

decadienal, (E)-2-decenal were the principal nematicidal constituents of AWE.

230

Interestingly the other aldehydes or ketones were not found nematicidal against RKN

231

(data not shown). Our results clearly indicate that α,β,γ,δ-unsaturated C10 aldehydes

232

are generally more potent nematicidal than their shortest C chain counterparts versus

233

M. javanica in vitro experiments. Kim reported that α,β-unsaturated aldehyde 2-

234

decenal showed the highest nematicidal activity at 200 mg/L against the pine wood

235

nematode (Bursaphelenchus xylophilus) if compared with other non unsaturated C8-

236

C10 aldehydes (24). On the other hand, Andersen et al. reported that C9 unsaturated

237

aldehydes i.e. (E)-2-nonenal and (E,Z)-nonadienal showed the strongest antifungal

238

activity against Alternaria alternata if compared with shortest chain aldehydes 11

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 12 of 27

239

concluding that the effectiveness is due to the their increased propensity to react with

240

thiols and amino groups of the target fungi (25).

241

Understanding the mode of action of the α,β and α,β,γ,δ-unsaturated C10 aldehydes is

242

of practical importance for developing new formulations and delivery systems for

243

nematode control. We observed that nematodes treated with aldehydes and ketones

244

were paralyzed in a straight shape, in a similar way as reported by Kim that treated

245

nematodes with plant essential oils (24), while Kong et al reported that pine wood

246

nematode treated with muscle activity blockers levamisole or morantal tartrate were

247

paralyzed in semi-circular and coiling shapes respectively (26). Moreover, we have

248

recently reported of the circular shape paralysis of J2s after immersion with the

249

organoposphorous fosthiazate (5).

250

Aliphatic aldehydes and in a lesser extent ketones are relatively reactive compounds.

251

The carbonyl carbon is an electrophilic site and reacts with primary amines and thiols

252

resulting in the formation of substituted imines called Schiff bases and hemiacetals

253

respectively. Aldehydes bringing one or two insaturations become even more reactive

254

being easily the site of nucleophilic attack. Taking into account the reactivity of

255

α,β,γ,δ-unsaturated aldehydes and E-SEM experiment photographs of the external

256

nematode cuticle following treatment with (E,E)-2,4-decadienal and furfural at 100

257

mg/L led us to hypothesized of the reaction of α,β,γ,δ-aldehydes with the nematode

258

cuticle through a Michael addiction. This reaction consists of a nucleophilic addition

259

of a cuticle amino or thiol group to an α,β-unsaturated carbonyl. This interaction leads

260

to evident cuticle damage and leakage of the internal fluid nematode material (Figure

261

2). Similar nematode cuticle damages were reported for Panagrellus redivivus caused

262

by a unique fungal structure on the vegetative hyphae of Coprinus comatus. The latter

263

was also able to produce potent nematicidal toxins such us 5-mehylfuran-3-carboxylic 12

ACS Paragon Plus Environment

Page 13 of 27

Journal of Agricultural and Food Chemistry

264

acid and 5-hydroxy-3,5-dimethylfuran-2(5H)-one (27, 28). Moreover, Luo et al.

265

observed that the fungus Stropharia rugosoannulata produced a severe mechanical

266

damage on the cuticle of nematodes Panagrellus redivivus and Bursaphelenchus

267

xylophilus through finger-like projections called acanthocytes (29).

268

The exact mechanism underlying the interaction of unsaturated aldehydes with the

269

nematode cuticle is still unclear. Currently, we are investigating the interaction of

270

aldehydes with the nematode cuticle trough a proteomic approach to well understand

271

protein glycation.

272 273

ABBREVIATIONS USED

274

GC-MS, gas chromatography-mass spectrometry; AWE, A. altissima wood

275

methanolic extract; ALE, A. altissima leaves methanolic extract, ABE, A. altissima

276

bark methanolic extract, ARE, A. altissima roots methanolic extract.

277 278

ACKNOWLEDGEMENTS

279

Special thanks to Dr. Marco Oggianu for performing ESEM analysis and Barbara

280

Liori for helpful suggestions.

281

13

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 14 of 27

282

LITERATURE CITED

283

(1) Reynolds A.M.; Dutta T.K.; Curtis R.S.C.; Power S.J.; Gaur H.S.; Kerry B.R.

284

Chemotaxis can take plant-parasitic nematodes to the source of a chemo-attractant via

285

the shortest possible routes. J. R. Soc. Interface. 2011, 8, 568-577.

286

(2) Isman, M.B. Botanical insecticides, deterrents, and repellents in modern

287

agriculture and an increasingly regulated world. Annu. Rev. Entomol. 2006, 51, 45-

288

66.

289

(3) Tian, B.; Yang, J.; Zhang, K.Q. Bacteria used in the biological control of plant

290

parasitic nematodes: populations, mechanisms of action, and future prospects. FEMS

291

Microbiol. Ecol. 2007, 61, 197-213.

292

(4) Rice. E.L. Allelopathy NY, Academic Press 1984.

293

(5) Ntalli, N. G.; Manconi F.; Leonti M.; Maxia A.; Caboni P. Aliphatic ketones from

294

Ruta chalepensis (Rutaceae) induce paralysis on root knot nematodes. J. Agric. Food

295

Chem. 2011, 59, 7098-7103.

296

(6) Ntalli, N. G.; Vargiu, S.; Menkissoglu-Spiroudi, U.; Caboni, P. Nematicidal

297

Carboxylic Acids and Aldehydes from Melia azedarach Fruits. J Agric Food Chem.

298

2010, 58, 11390–11394.

299

(7) Bauske E.M.; Rodríguez-Kábana R.; Estaun V.; Kloepper J.W.; Robertson D.G.;

300

Weaver C.F.; King P.S. Management of Meloidogyne incognita on cotton by use of

301

botanical aromatic compounds. Nematropica. 1994, 24, 143–150.

302

(8) Oka Y.; Nacar S.; Putievsky E.; Ravid U.; Yaniv Z.; Spiegel Y. Nematicidal

303

activity of essential oils and their components against the root-knot nematode.

304

Phytopathology 2000, 90710–715

305

(9) Rohloff V.J. Volatiles from rhizomes of Rhodiola rosea L. Phytochem 2002, 59,

306

655–661. 14

ACS Paragon Plus Environment

Page 15 of 27

Journal of Agricultural and Food Chemistry

307

(10) Kokalis-Burelle N.; Martinez-Ochoa N.; Rodríguez-Kabana R.; Kloepper J.W.

308

Development of multicomponent transplant mixes for suppression of Meloidogyne

309

incognita on tomato (Lycopersicum esculentum). J Nematol. 2002, 34,362–369.

310

(11) Bertoli A.; Pistelli L.; Morelli I.; Fraternale D.; Giamperi L.; Ricci D. Volatile

311

constituents of different parts (roots, stems and leaves) of Smyrnium olusatrum L.

312

Flavour Fragr J. 2004, 19, 522–525.

313

(12) Weissteiner S.; Schütz S. Are different volatile pattern influencing host plant

314

choice of belowground living insects. Mitt Dtsch. Ges Allg. Angew Ent. 2006, 15, 51–

315

55.

316

(13) van Tol R.W.H.M.; van der Sommen A.T.C.; Boff M.I.C.; van Bezooijen J.;

317

Sabelis M.W.; Smits P.H. Plants protect their roots by alerting the enemies of grubs.

318

Ecol Lett. 2001 4, 292–294.

319

(14) Heisey R.M. Allelopathy and the secret life of Ailanthus altissima. Arnoldia –

320

Suffolk County (MA), 1997, 28-36.

321

(15) Andersen R.A.; Hamilton-Kemp T.R.; Hildebrand D.F.; McCracken C.T.;

322

Collins R.W.; Fleming P.D. Structure-antifungal activity relationship among volatile

323

C6 and C9 aliphatic aldehydes, ketones, and alcohols. J. Agric. Food Chem. 1994, 42,

324

1563-1568.

325

(16) Wenke K.; Kai M.; Piechulla B. Belowground volatiles facilitate interactions

326

between plant roots and soil organism. Planta 2010, 231, 499-506.

327

(17) Hildebrand D.F. Lipoxygenases. Physiol. Plant. 1989, 76, 249-253.

328

(18) Roberts, M.J.; Wondrak G.T.; Laurean D.C.; Jacobson M.K.; Jacobson E.L.;

329

DNA damage by carbonyl stress in human skin cells. Mutat. Res-Fund. Mol. M. 2003,

330

522, 45-56.

15

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 16 of 27

331

(19) De Martino L.; De Feo V. Chemistry and biological activities of Ailanthus

332

altissima Swingle: A review. Phcog. Rev. 2008, 2, 339-350.

333

(20) Kraus W.; Koll-Weber M.; Maile R.; Wunder T.; Vogler B. Biologically active

334

constituents of tropical and subtropical plants. Pure Appl. Chem. 1994, 66, 2347-

335

2352.

336

(21) Puntener W. Manual for Field Trials in Plant Protection, 2nd ed.; Ciba Geigy:

337

Basel, Switzerland, 1981; pp 205

338

(22) Seefeldt, S.S.; Jensen, J.E.; Fuerst, E.P. Log-logistic analysis of herbicide rate

339

response relationships. Weed Technol. 1995, 9, 218–227.

340

(23) Meyer S.L.; Zasada I.A.; Roberts D.P.; Vinyard B.T.; Lakshman D.K.; Lee J.K.;

341

Chitwood D.J.; Carta L.K. Plantago lanceolata and Plantago rugelii extracts are toxic

342

to Meloidogyne incognita but not to Certain Microbes. J Nematol. 2006, 38, 333-338.

343

(24) Kim J.; Seo S.M.; Lee S.G.; Shin S.C.; Park I.K. Nematicidal activity of plant

344

essential oils and components from Coriander (Coriandrum sativum), oriental

345

sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii), essential oils

346

against pie wood nematode (Bursaphelenchus xylophilus). J. Agric. Food Chem.

347

2008, 56, 7316-7320.

348

(25) Andersen R.A.; Hamilton-Kemp T.R.; Hildebrand D.F.; McCracken C.T.;

349

Collins R.W.; Fleming P.D. Structure-antifungal activity relationship among volatile

350

C6 and C9 aliphatic aldehydes, ketones, and alcohols. J. Agric. Food Chem. 1994, 42,

351

1563-1568.

352

(26) Kong J.O.; Lee S.M.; Moon Y.S.; Lee S.G.; Ahn Y.J. Nematicidal activity of

353

plant

354

Aphelenchoididae). J. Asia-Pacific Entomol. 2006, 9, 173-178.

essential

oils

against

Bursaphelenchus

xylophilus

(Nematoda

16

ACS Paragon Plus Environment

Page 17 of 27

Journal of Agricultural and Food Chemistry

355

(27) Luo H.; Mo M.H.; Huang X.W.; Li X.; Zhang K.Q. Coprinus comatus: a

356

basidiomycete fungus forms novel spiny structures and infects nematodes. Mycologia.

357

2004, 96, 1218-1225.

358

(28) Luo H.; Liu Y.; Fang L.; Li X.; Tang N.; Zhang K. Coprinus comatus damages

359

nematode cuticle mechanically with spiny ball and produces potent toxins to

360

immobilize nematodes. Appl. Environ. Microb.. 2007, 3916-3923.

361

(29) Luo H.; Li X.; Li G.; Pan Y.; Zhang K. Acanthocytes of Stropharia

362

rugosoannulata function as a nematode-attacking device. Appl. Environ. Microb..

363

2006, 2982-2987

17

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

364 365 366 367

Page 18 of 27

Table 1. Composition of AWE, ALE, ARE, and ABE Extracts Determined by GCMS Analysis, Listed in Order of Elution. Identification Was Done by Comparison of Mass Spectra of Commercial Standards with the Respective Data of NIST Library in Total Ion Current (TIC) and the Literature, anc=not calculated.

18

ACS Paragon Plus Environment

Page 19 of 27

Journal of Agricultural and Food Chemistry

compound

tR

EIMS

(min)

m/z (amu), (abundance)

mol. wt.

AWE

ALE

ABE

ARE

(mg/kg)

(mg/kg)

(mg/kg)

(mg/kg)

____________________________________________________________________________________________________________________ hexanal

10.88 56 (100%); 72(63%); 82(47%)

100.2

179

-

nonanal

22.71 57 (100%); 82 (51%); 70 (49%)

142.2

61.1

53

(E)-2-octenal

24.27 70 (100%); 55 (82%); 83 (70%)

126.1

44.7

acetic acid

25.59 60 (100%); 69 (10%)

60.0

furfural

25.84 95 (100%); 94 (91%); 59 (13%)

-

-

76

58

-

-

-

108

271

419

280

96.1

1.38

-

-

-

[R-(R*,R*)]-2,3-butanediol 28.73 60 (100%); 75 (80%)

90.1

7.36

-

-

-

[S-(R*,R*)]-2,3-butanediol

30.20 57 (100%); 75 (60%); 72 (20%)

90.1

14.7

-

-

-

2-decenal

32.89 70 (100%); 55 (77%); 83 (65%)

154.2

33.2

-

-

-

2-undecenal

36.99 70 (100%); 83 (73%); 55 (62%)

168.3

37.7

-

-

-

(E,Z)-2,4-decadienal

37.52 81 (100%); 83 (28%); 67 (17%)

152.2

68.6

-

-

-

(E,E)-2,4-decadienal

39.20 81 (100%); 83 (19%); 67 (18%)

152.2

124

-

-

-

hexanoic acid

40.55 56 (100%); 73 (79%); 87 (24%)

116.2

48

4.0

11.9

13.3

144.1

nc

n.c.

n.c.

2,3-dihydro-3,5-dihydroxy- 54.52 97 (100%); 126 (79%); 69 (31%) 6-methyl-4H-pyran-4-one

n.c.

5-hydroxymethylfurfural 61.59 144 (100%); 101 (48%);73 (28%) 126.1 70 55 ____________________________________________________________________________________________________________________ 19

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 20 of 27

Table 2. EC50 and R2 Values of Individual Compounds against Meloidogyne javanica Calculated at 1 hour and 1 day after Immersion in Test Solutionsa

1 hour

1 day

______________________ R2

EC50 compound

________________________

(mg/L)

EC50

R2

(mg/L)

(E,E)-2,4-decadienal

7.53

0.98a

11.70

0.97

(E)-2-decenal

11.75

0.98

20.43

0.93

(E)-2-undecenal

>25

-

>25

-

(E)-2-octenal

n.a.

-

>25

-

nonanal

>50

-

n.a.

-

heptanal

n.a.

-

n.a.

-

hexanal

n.a.

-

n.a.

-

furfural

>25

-

21.79

0.98

5-hydroxy-methylfurfural

>25

-

>25

-

fosthiazate

>25

-

15.9

0.98

_______________________________________________________________________________ a

If R2 values are not presented and the EC50 values have not been calculated, they were outside the test concentration range and they are estimated higher than the upper concentration level (25 mg/L). n.a. not active in the range 25-1000 mg/L.

20

ACS Paragon Plus Environment

Page 21 of 27

Journal of Agricultural and Food Chemistry

Table 3. EC50 and R2 Values of Ailanthus altissima Extracts (ALE, ABE, AWE and ARE) against Meloidogyne javanica Calculated after 3 Days of Immersion in Test Solutionsa and Respective Concentration of Each Extract Provoking 100 % Paralysis.

3 days

4 days

___________________________

________________________

EC50 extract a

R2

(mg/L)

100% mortality

100% mortality

(mg/L)

(mg/L)

_______________________________________________________________________________ AWE

58.9

0.91

500

31.2

ABE

>250

-

625

312

ALE

>250

-

>2500

>2500

ARE

>250

-

>2500

>2500

________________________________________________________________________________________________________________________________________

a

A. altissima methanolic extracts of: AWE = wood; ALE = leaves; ABE = bark: ARE = roots.

21

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 22 of 27

List of figure captions of the paper entitled:

Figure 1. GC-MS chromatograms of A. altissima methanol extracts. Peaks A). (1) hexanal, (2) nonanal, (3) (E)-2-octenal, (4) acetic acid, (5) furfural, (6) (E,Z)-2,3-butanediol, (7) (E,E)-2,3butanediol, (8) (E)-2-decenal, (9) (E)-2-undecenal, (10) (E,Z)-2,4-decedienal, (11) (E,E)-2,4decedienal, (12) hexanoic acid, (13) 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (14) 5hydroxymethylfurfural. Peaks B). (1) nonanal, (2) acetic acid, (3) 2-nonanol, (4) 1-octanol, (5) hexanoic acid. Peaks C) (1) nonanal, (2) acetic acid, (3) hexanoic acid (4) 2,3-dihydro-3,5dihydroxy-6-methyl-4H-pyran-4-one (5) 5-hydroxymethylfurfural. Peaks D) (1) nonanal, (2) acetic acid, (3) decanal, (4) hexanoic acid. Figure 2. E-SEM topographical images from immersion treatment of J2 with water A) and B), C) and D) furfural at 100 mg/L, while E) and F) were treatment with (E,E)-2,4-decadienal at 100 mg/L. Degradation of the external cuticle of M. incognita juveniles is evidenced by the leakage of internal fluids D) E) and F).

22

ACS Paragon Plus Environment

Page 23 of 27

Journal of Agricultural and Food Chemistry

Figure 1 100 90

A wood

8

80

14

11

70

13

1 60

12

2

50

10 7

40

9

6

30

4 3 5

20 10 0 10

15

20

25

30

35 40 Time (min)

45

50

55

60

65

45

50

55

60

65

100 90

B root

80 70

2

60 50

5 40 30

3 20

4

1

10 0 10

15

20

25

30

35 40 Time (min)

23

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

Page 24 of 27

4

100 90

C leaves

80 70 60 50

5

2

40 30

3

20

1

10 0 10

15

20

25

30

35 40 Time (min)

45

50

55

60

65

45

50

55

60

65

3

100 90 80

D bark 70 60

2

50 40

1

30

4

20 10 0 10

15

20

25

30

35 40 Time (min)

24

ACS Paragon Plus Environment

Page 25 of 27

Journal of Agricultural and Food Chemistry

Figure 2

25

ACS Paragon Plus Environment

Journal of Agricultural and Food Chemistry

A

B

C

D

E

F

Page 26 of 27

26

ACS Paragon Plus Environment

Page 27 of 27

Journal of Agricultural and Food Chemistry

Degradation of the external cuticle of M. javanica with evident leakage of its internal fluids after treatment with (E,E)-2,4-decadienal at 100 mg/L

ACS Paragon Plus Environment

Lihat lebih banyak...

Comentários

Copyright © 2017 DADOSPDF Inc.