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Isolation, purification and identification of the active compound of turmeric and its potential application to control cucumber powdery mildew

Published online by Cambridge University Press:  17 May 2018

W. J. Fu ,
J. Liu ,
M. Zhang ,
J. Q. Li ,
J. F. Hu ,
L. R. Xu  and
G. H. Dai
W. J. Fu
Affiliation:
Plant Health and Natural Products Lab, Key Lab of Urban Agriculture (South), Ministry of Agriculture, School of Agriculture and Biology, Shanghai Jiao Tong University, 800 Dong Chuan Road, Shanghai 200240, PR, China
J. Liu
Affiliation:
Plant Health and Natural Products Lab, Key Lab of Urban Agriculture (South), Ministry of Agriculture, School of Agriculture and Biology, Shanghai Jiao Tong University, 800 Dong Chuan Road, Shanghai 200240, PR, China
M. Zhang
Affiliation:
Plant Health and Natural Products Lab, Key Lab of Urban Agriculture (South), Ministry of Agriculture, School of Agriculture and Biology, Shanghai Jiao Tong University, 800 Dong Chuan Road, Shanghai 200240, PR, China
J. Q. Li
Affiliation:
Plant Health and Natural Products Lab, Key Lab of Urban Agriculture (South), Ministry of Agriculture, School of Agriculture and Biology, Shanghai Jiao Tong University, 800 Dong Chuan Road, Shanghai 200240, PR, China
J. F. Hu
Affiliation:
School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 200240, PR, China
L. R. Xu
Affiliation:
Plant Health and Natural Products Lab, Key Lab of Urban Agriculture (South), Ministry of Agriculture, School of Agriculture and Biology, Shanghai Jiao Tong University, 800 Dong Chuan Road, Shanghai 200240, PR, China
G. H. Dai*
Affiliation:
Plant Health and Natural Products Lab, Key Lab of Urban Agriculture (South), Ministry of Agriculture, School of Agriculture and Biology, Shanghai Jiao Tong University, 800 Dong Chuan Road, Shanghai 200240, PR, China
*
Author for correspondence: G. H. Dai, E-mail: [email protected]
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Abstract

Cucumber powdery mildew is a destructive foliar disease caused by Podosphaera xanthii (formerly known as Sphaerotheca fuliginea) that substantially damages the yield and quality of crops. The control of this disease primarily involves the use of chemical pesticides that cause serious environmental problems. Currently, numerous studies have indicated that some plant extracts or products potentially have the ability to act as natural pesticides to control plant diseases. It has been reported that turmeric (Curcuma longa L.) and its extract can be used in agriculture due to their insecticidal and fungicidal properties. However, the most effective fungicidal component of this plant is still unknown. In the current study, the crude extract of C. longa L. was found to have a fungicidal effect against P. xanthii. Afterwards, eight fractions (Fr.1–Fr.8) were gradually separated from the crude extract by column chromatography. Fraction 1 had the highest fungicidal effect against this pathogen among the eight fractions. The active compound, (+)-(S)-ar-turmerone, was separated from Fr 1 by semi-preparative high-performance liquid chromatography and identified based on its 1H nuclear magnetic resonance (NMR) and 13C NMR spectrum data. The EC50 value of (+)-(S)-ar-turmerone was found to be 28.7 µg/ml. The compound also proved to have a curative effect. This is the first study to report that the compound (+)-(S)-ar-turmerone has an effect on controlling this disease. These results provide a basis for developing a new phytochemical fungicide from C. longa L. extract.

Keywords

(+)-(S)-ar-turmeronebiopesticidecucumber powdery mildewturmeric
Type
Crops and Soils Research Paper
Information
The Journal of Agricultural Science , Volume 156 , Issue 3 , April 2018 , pp. 358 - 366
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Copyright
Copyright © Cambridge University Press 2018 

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References

Ammon, HPT and Wahl, MA (1991) Pharmacology of Curcuma longa. Planta Medica 57, 1–7.CrossRefGoogle ScholarPubMed
Aratanechemuge, Y et al. (2002) Selective induction of apoptosis by ar-turmerone isolated from turmeric (Curcuma longa L.) in two human leukemia cell lines, but not in human stomach cancer cell line. International Journal of Molecular Medicine 9, 481–484.Google ScholarPubMed
Bartlett, DW et al. (2002) The strobilurin fungicides. Pest Management Science 58, 649–662.CrossRefGoogle ScholarPubMed
Bassil, KL et al. (2007) Cancer health effects of pesticides: systematic review. Canadian Family Physician 53, 1704–1711.Google Scholar
BBCH (Biologische Bundesanstallt für Land-und Forstwirtschaft) (1997) Growth Stages of Mono-and Dicotyledonous Plants: BBCH Monograph. Berlin: Blackwell Wissenschafts-Verlag.Google Scholar
Bergeron, C et al. (1995) Antifungal constituents of Chenopodium procerum. International Journal of Pharmacognosy 33, 115–119.Google Scholar
Cantrell, CL, Dayan, FE and Duke, SO (2012) Natural products as sources for new pesticides. Journal of Natural Products 75, 1231–1242.Google Scholar
Carvalho, PIN et al. (2015) Techno-economic evaluation of the extraction of turmeric (Curcuma longa L.) oil and ar-turmerone using supercritical carbon dioxide. Journal of Supercritical Fluids 105, 44–54.CrossRefGoogle Scholar
Chander, H and Kulkarni, SG (1992) Studies on turmeric and mustard oil as protectants against infestation of red flour beetle, Tribolium castaneum (Herbst.) in stored milled rice. Journal of Insect Science 5, 220–222.Google Scholar
Chowdhury, H, Walia, S and Saxena, VS (2000) Isolation, characterization and insect growth inhibitory activity of major turmeric constituents and their derivatives against Schistocerca gregaria (Forsk) and Dysdercus koenigii (Walk). Pest Management Science 56, 1086–1092.3.0.CO;2-X>CrossRefGoogle Scholar
Clough, JM (2000) The strobilurin fungicides – from mushroom to molecule to market. In Wrigley, SK, Hayes, MA, Thomas, R, Chrystal, EJT and Nicholson, N (eds), Biodiversity: New Leads for the Pharmaceutical and Agrochemical Industries. Cambridge, UK: Royal Society of Chemistry, pp. 277–282.Google Scholar
Daayf, F, Schmitt, A and Belanger, RR (1995) The effects of plant extracts of Reynoutria sachalinensis on powdery mildew development and leaf physiology of long English cucumber. Plant Disease 79, 577–580.Google Scholar
Dik, AJ and van der Staay, M (1995) The effect of Milsana on cucumber powdery mildew under Dutch conditions. Mededelingen van de Faculteit Landbouwwetenschappen, Rijksuniversiteit Gent 59, 1027–1034.Google Scholar
Duan, Y et al. (2013) Effect of phenylpyrrole fungicide fludioxonil on morphological and physiological characteristics of Sclerotinia sclerotiorum. Pesticide Biochemistry & Physiology 106, 61–67.Google Scholar
Duan, S et al. (2016) Chemical basis of the fungicidal activity of tobacco extracts against Valsa mali. Molecules 21, 1743.Google Scholar
Ferreira, LA et al. (1992) Biologically active peptides from Bothrops jararacussu venom. Agents & Actions Supplements 36, 209–214.Google Scholar
Fujiwara, M et al. (2011) Biotransformation of turmerones by Aspergillus niger. Journal of Natural Products 74, 86–89.Google Scholar
Fukino, N et al. (2013) Identification and validation of powdery mildew (Podosphaera xanthii)-resistant loci in recombinant inbred lines of cucumber (Cucumis sativus L.). Molecular Breeding 32, 267–277.CrossRefGoogle Scholar
Gafni, A et al. (2015) Biological control of the cucurbit powdery mildew pathogen Podosphaera xanthii by means of the epiphytic fungus Pseudozyma aphidis and parasitism as a mode of action. Frontiers in Plant Science 6, 132.Google Scholar
Gilardi, G et al. (2008) Efficacy of the biocontrol agents Bacillus subtilis and Ampelomyces quisqualis applied in combination with fungicides against powdery mildew of zucchini. Journal of Plant Diseases & Protection 115, 208–213.Google Scholar
Grieco, PA and Finkelhor, RS (1973) Dianions of .beta.-ketophosphonates. Two-step synthesis of (+)-ar-turmerone. Journal of Organic Chemistry 38, 2909–2910.Google Scholar
Hanke, W and Jurewicz, J (2004) The risk of adverse reproductive and developmental disorders due to occupational pesticide exposure: an overview of current epidemiological evidence. International Journal of Occupational Medicine & Environmental Health 17, 223–243.Google ScholarPubMed
Herger, G and Klingauf, F (1990) Control of powdery mildew fungi with extracts of the giant knotweed, Reynoutria sachalinensis (Polygonaceae). Mededelingen van de Faculteit Landbouwwetenschappen, Rijksuniversiteit Gent 55, 1007–1014.Google Scholar
Hernández, AF et al. (2011) Emerging human health concerns from chronic exposure to pesticide mixtures. Toxicology Letters 205, S4–S5.Google Scholar
Horsfield, A et al. (2010) Effect of fungicide use strategies on the control of early blight (Alternaria solani) and potato yield. Australasian Plant Pathology 39, 368–375.CrossRefGoogle Scholar
Jilani, G and Saxena, RC (1990) Repellent and feeding deterrent effects of turmeric oil, sweetflag oil, neem oil, and a neem-based insecticide against lesser grain borer (Coleoptera: Bostrychidae). Journal of Economic Entomology 83, 629–634.Google Scholar
Kanavouras, K et al. (2011) A case report of motor neuron disease in a patient showing significant level of DDTs, HCHs and organophosphate metabolites in hair as well as levels of hexane and toluene in blood. Toxicology & Applied Pharmacology 256, 399–404.Google Scholar
Kavková, M and Curn, V (2005) Paecilomyces fumosoroseus (Deuteromycotina: Hyphomycetes) as a potential mycoparasite on Sphaerotheca fuliginea (Ascomycotina: Erysiphales). Mycopathologia 159, 53–63.CrossRefGoogle ScholarPubMed
Kim, MK, Choi, GJ and Lee, HS (2003) Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. Journal of Agricultural & Food Chemistry 51, 1578–1581.CrossRefGoogle Scholar
Kiss, L et al. (2010) Microcyclic conidiogenesis in powdery mildews and its association with intracellular parasitism by Ampelomyces. European Journal of Plant Pathology 126, 445–451.CrossRefGoogle Scholar
Konstantinidou-Doltsinis, S and Schmitt, A (1998) Impact of treatment with plant extracts from Reynoutria sachalinensis (F. Schmidt) Nakai on intensity of powdery mildew severity and yield in cucumber under high disease pressure. Crop Protection 17, 649–656.CrossRefGoogle Scholar
London, L et al. (2012) Neurobehavioral and neurodevelopmental effects of pesticide exposures. NeuroToxicology 33, 887–896.CrossRefGoogle ScholarPubMed
Ma, Q et al. (2005) Effect of oligosaccharide on the resistance induction of cucumber against Sphaerotheca fuliginea. Journal of Northwest Sci-Tech University of Agriculture and Forestry 33, 79–81.Google Scholar
Nave, S et al. (2010) Protodeboronation of tertiary boronic esters: asymmetric synthesis of tertiary alkyl stereogenic centers. Journal of the American Chemical Society 132, 17096–17098.CrossRefGoogle ScholarPubMed
Pang, Q et al. (2015) Effects of turmeric root extract on the control of cucumber powdery mildew. China Plant Protection 35, 63–66.Google Scholar
Parrón, T et al. (2011) Association between environmental exposure to pesticides and neurodegenerative diseases. Toxicology & Applied Pharmacology 256, 379–385.CrossRefGoogle ScholarPubMed
Petsikos-Panayotarou, N et al. (2002) Management of cucumber powdery mildew by new formulations of Reynoutria sachalinensis (F. Schmidt) Nakai extract. Zeitschrift Für Pflanzenkrankheiten Und Pflanzenschutz 109, 478–490.Google Scholar
Pfender, WF (2006) Interaction of fungicide physical modes of action and plant phenology in control of stem rust of perennial ryegrass grown for seed. Plant Disease 90, 1225–1232.Google Scholar
Romero, D et al. (2007) The iturin and fengycin families of lipopeptides are key factors in antagonism of Bacillus subtilis toward Podosphaera fusca. Molecular Plant-Microbe Interactions 20, 430–440.Google Scholar
Rowe, BJ and Spilling, CD (2003) Stereospecific Pd (0)-catalyzed arylation of an allylic hydroxy phosphonate derivative: formal synthesis of (S)-(+)-ar-turmerone. The Journal of Organic Chemistry 68, 9502–9505.Google Scholar
Sakugawa, H et al. (2012) Protective and curative effects of foliar-spray Fenton solutions against cucumber (Cucumis sativus, L.) powdery mildew. Journal of Environmental Science & Health Part A Toxic/Hazardous Substances & Environmental Engineering 47, 1909–1918.Google Scholar
Sauter, H, Steglich, W and Anke, T (1999) Strobilurins: evolution of a new class of active substances. Angewandte Chemie International Edition 38, 1328–1349.3.0.CO;2-1>CrossRefGoogle ScholarPubMed
Su, HCF, Horvat, R and Jilani, G (1982) Isolation, purification, and characterization of insect repellents from Curcuma longa L. Journal of Agricultural & Food Chemistry 30, 290–292.Google Scholar
Tang, R, Wang, X and Zhang, X (2005) Extract and compound analysis of activity fractions against powdery mildew of cucumber from Rheum palmatum. Journal of Anhui Agricultural University 32, 441–443.Google Scholar
Tripathi, P and Dubey, NK (2004) Exploitation of natural products as an alternative strategy to control postharvest fungal rotting of fruit and vegetables. Postharvest Biology & Technology 32, 235–245.CrossRefGoogle Scholar
Varo, A et al. (2017) Screening water extracts and essential oils from Mediterranean plants against Verticillium dahliae in olive. Crop Protection 92, 168–175.Google Scholar
Wurms, K et al. (1999) Effects of milsana and benzothiadiazole on the ultrastructure of powdery mildew haustoria on cucumber. Phytopathology 89, 728–736.Google Scholar
Zaker, M (2016) Natural plant products as eco-friendly fungicides for plant diseases control – a review. The Agriculturists 14, 134–141.Google Scholar
Zhang, ZY et al. (2008) Protective effect of Robinia pseudoacacia Linn1 extracts against cucumber powdery mildew fungus, Sphaerotheca fuliginea. Crop Protection 27, 920–925.CrossRefGoogle Scholar