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CHEMISTRY AND INSECTICIDAL POTENTIAL OF PARTHENIN AND ITS TRANSFORMATION ... PDF

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CHEMISTRY AND INSECTICIDAL POTENTIAL OF PARTHENIN AND ITS TRANSFORMATION REACTION PRODUCTS AGAINST Tribolium castaneum (Herbst). Thesis Submitted to the Punjab Agricultural University in partial fulfillment of the requirements for the degree of MASTER OF SCIENCE in CHEMISTRY (Minor Subject: Biochemistry) By Ramandeep Kaur (L-2010-BS-196-M) Department of Chemistry College of Basic Sciences and Humanities © PUNJAB AGRICULTURAL UNIVERSITY LUDHIANA – 141 004 2012 CERTIFICATE I This is to certify that the thesis entitled Chemistry and insecticidal potential of parthenin and its transformation reaction products against Tribolium castaneum (Herbst) submitted for the degree of M.Sc., in the subject of Chemistry (Minor subject: Biochemistry) of the Punjab Agricultural University, Ludhiana, is a bonafide research work carried out by Ramandeep Kaur (L-2010-BS-196-M) under my supervision and that no part of this thesis has been submitted for any other degree. The assistance and help received during the course of investigation have been fully acknowledged. _________________________ MajorAdvisor Dr. (Mrs.) K. K. Chahal Professor-cum-Head Department of Chemistry Punjab Agricultural University Ludhiana - 141004 CERTIFICATE II This is to certify that the thesis entitled, Chemistry and insecticidal potential of parthenin and its transformation reaction products against Tribolium castaneum (Herbst) submitted by Ramandeep Kaur (Admn. No. L-2010-BS-196-M) to the Punjab Agricultural University, Ludhiana, in partial fulfillment of the requirements for the degree of M.Sc. in the subject of Chemistry (Minor subject: Biochemistry) has been approved by the Student’s Advisory Committee along with Head of the Department after an oral examination on the same. _ _ {Dr. (Mrs.) K. K. Chahal} {Dr. (Mrs.) K. K. Chahal} Head of the Department Major Advisor ______________________ (Dr. Gursharan Singh) Dean Postgraduate Studies Acknowledgements Firstly, I bow my head with utmost reverence before the Almighty whose eternal blessing has enabled me to accomplish this noble effort. It gives me immense pleasure to record my thanks and sense of profound gratitude to my Major Advisor Dr. (Mrs.) K. K. Chahal, Professor-cum-Head, Department of Chemistry, Punjab Agricultural University, Ludhiana, for her expert guidance, encouragement, inspiration and advice throughout my research work. It was my privilege to be guided by a person of calibre, whose blessings bring best in every one of my endeavours. Special thanks are accorded to Dr. B. R. Chhabra, Professor Adjunct for his excellent technical guidance and support. I owe my unpayable debt to the other esteemed members of my advisory committee. Dr. (Mrs.) Manpreet Kaur, Assistant Professor, Department of Chemistry, Dr. (Mrs.) Bavita Asthir Senior Biochemist, Department of Biochemistry, Dr. (Mrs.) B.K. Kang, Associate Professor, Department of Entomology, Dr. (Mrs.) S.K. Uppal ,Senior Biochemist-cum-Incharge of Sugarcane Section, Department of Plant Breeding and Genetics, for their able guidance , constructive suggestions and continuous support. I am indebted to my respected family for their constant words of encouragement, deep affection and heartful blessings that enabled me to this stage of career. Friends are always a moral support which is extremely important when one is feeling low. I take great pleasure in thanking my friends Ajay, Dalvir, Amanpal and Amit for giving me moral support, sharing the burden of my work and making things smooth. My sincerest thanks to Mr. Banjit Singh, Mr. Mukesh Kumar and Mr. Raj Singh for their invaluable and generous help in the laboratory. I feel proud to be a part of PAU, Ludhiana where I learnt a lot and spent some unforgettable moments of my life. I thankful to Punjab Agricultural University for providing merit fellowship during final year of my M.Sc. Last but not least, I duly acknowledge my sincere thanks to all who love and care for me. _____________ (Ramandeep Kaur) Title of the Thesis : Chemistry and insecticidal potential of parthenin and its transformation reaction products against Tribolium castaneum (Herbst) Name of the Student : Ramandeep Kaur and Admission No. L-2010-BS-196-M Major Subject : Chemistry Minor Subject : Biochemistry Name and Designation : Dr. (Mrs.) K. K. Chahal of Major Advisor Professor- cum-Head Degree to be Awarded : M.Sc. Year of Award of Degree : 2012 Total Pages in Thesis : 73 + VITA Name of University : Punjab Agricultural University, Ludhiana-141 04 ABSTRACT The present investigation deals with Chemistry and insecticidal potential of parthenin and its transformation reaction products against Tribolium castaneum (Herbst).The shade dried and powdered leaves of Parthenium hysterophorous were extracted in chloroform using Soxhlet extraction method. Parthenin was isolated by column chromatography using chloroform:acetone (5%) solution as the eluent. Parthenin was subjected to reaction with diazoester which resulted into the formation of two compounds- pyrolysis product and diazoester adduct. Parthenin on reactions with dry hydrochloric acid gas and formic acid gets converted into anhydroparthenin. Parthenin on irradiation with microwave gets converted into anhydroparthenin. Parthenin and its derivatives were 1 characterised on the basis of melting point, TLC, FT-IR and H NMR. Parthenin and its derivatives were tested for their bioefficacy against adults of Tribolium castaneum (Herbst) by releasing them in wheat grains spiked with various concentrations of test compounds viz. -1 1,000, 2,000, 4,000, 5,000, 10,000 and 20,000 μg g of wheat respectively. The observations of mortality were noted every 24 hours till complete or constant mortality was obtained. The corrected per cent mortality was calculated using Abbott’s formula. All the compounds -1 exhibited complete mortality at the spiking level of 10,000 and 20,000μg g . Parthenin was found to be most potent followed by anhydroparthenin, pyrolysis product and diazoester adduct. Key words: Parthenium hyseterophorous, Bioefficacy, Tribolium castaneum, Soxhlet extraction. _ _ Signature of Major Advisor Signature of the Student Koj pRbMD dw isrlyK : pwrQinn Aqy ausdy pRXog duAwrw bdly hoey auqpwdW dI trWeIbolIAm kYstyinAm dy ivru`D rswieixk Aqy kItnSk Xogqw[ ividAwrQI dw nwm Aqy : rmndIp kOr dwKlw nM. (AYl-2010-bI.AYs.-196-AYm) mu`K ivSw : rswiex ivigAwn inmn ivSw : jIv-rswiex ivigAwn mu`K slwhkwr dw nwm Aqy : fw. ky.ky. cihl Ahudw pRoPYsr Aqy mu`KI ifgrI : AYm.AYs.sI. ifgrI imlx dw swl : 2012 Koj pRbMD iv`c ku`l pMny : 73 + vItw XUnIvristI dw nwm : pMjwb KyqIbwVI XUnIvristI, luiDAwxw - 141004 Swr-AMS mOjUdw AiDAYn “pwrQinn Aqy ausdy pRXog duAwrw bdly hoey auqpwdW dI tRweIbolIAm kYstyinAm dy ivru`D rswiexik Aqy kItnwSk Xogqw” isrlyK hyT Aml iv`c ilAWdw igAw[ AiDAYn smyN kIqy gey qzrby dOrwn pwrQInIAm ihstIroPors dy CwvyN sukwey Aqy pIsy hoey p`iqAW dw Ark kloroPwrm iv`c sOksly~t ivDI duAwrw k`iFAw igAw[ kwlm kromYtogrwPI duAwrw pwrQinn nUM kloroPwrm: AYsIton (5%) dy Gol nwl v`K kIqw igAw[ pwrQinn dI ikirAw fweIAYjoAYstr nwl krvweI geI ijsdy is`ty vjoN do Xojk-pweIrolweIiss prOfkt Aqy fweIAYjoAYstr Af`kt bxy[ fRweI hweIfRokloirk AYisf gYs Aqy Pwrimk AYisf nwl ikirAw krky pwrQinn AYnhweIfRopwriQinn iv`c bdl geI[ pwrQinn qy mweIkRovyv ikrnW pwaux nwl ieh AYnhweIfRopwrQinn iv`c pirvriqq ho geI[ pwrQinn Aqy ausdy ivauqpMnw nUM ipGlw ibMdU, tI.AYl.sI., AYP.tI.AweI.Awr. Aqy pRoton AYn.AYm.Awr. ivDIAW duAwrw jWicAw igAw[ pwrQinn Aqy iesdy ivauqpMnw dw jYivk-kuSlqw prIKx tRweIbolIAm kYstynIAm dy iKlwP kxk dy dwixAW qy v`K-v`K mwqrw iv`c prIiKk imSrx lgw ky jo ik kRmvwr 1000, 2000, 4000, -1 5000, 10000 Aqy 20000 μg g hn, kIqw igAw[ mOq dr dw inrIKx hr 24 GMitAW bwAd kiqI igAw jdoN q`k ik pUrx jW siQr mrnSIlqw pRwpq nhIN ho geI[ korYkitf prsYNt mortYiltI nUM AY~bt PwrmUly duAwrw k`iFAw igAw[ 10000 Aqy 20000 mweIkRo gRwm/gRwm GxqwvW qy swry imSrxw duAwrw pUrn mOq dr drsweI geI[ mOjUd AiDAYn dy is`itAW qoN ieh q`Q swhmxy Awey ik AYnhweIfRopwrQinn, pwierOiliss profkt, fweIjoAYstR Af`kt dy mukwbly pwrQinn sB qoN v`D pRBwvSwlI sI[ mu`K Sbd: pwrQinAm ihstIroPors, jYivk kuSlqw, tRweIbolIAm kYstynIAm, soks lYt AYsktRykSn __________________ ______________ pRmu`K slwhkwr dy hsqwKr ividAwrQI dy hsqwKr CONTENTS CHAPTER TOPIC PAGE I. INTRODUCTION 1-4 I. REVIEW OF LITERATURE 5-24 I. MATERIAL AND METHODS 25-32 IV. RESULTS AND DISCUSION 3-57 V. SUMMARY 58-60 REFERENCES 61-73 VITA CHAPTER – I INTRODUCTION Wheat (Triticum aestivum L.) of Family Gramineae is an important staple foodstuff in North India. Post-harvest losses of wheat are due to biotic (insects, molds, rodents and birds) as well as abiotic (temperature, relative humidity and moisture content of the grains) factors. Among the biotic processes, insect pests are the major agent, which cause considerable losses in terms of quality and quantity of food grains. The damage caused by insect pests to wheat grain has been estimated at 10 to 20 percent (Ramzan et al 1991, Khan et al 2010). Tribolium castaneum has been found to be one of major insect pest of wheat according to surveys conducted (Mahmood et al 1996, Ghizdavu and Deac 1994, Khalil and Irshad 1994, Desimpelaere 1996, Bandyopadhyay and Ghosh 1999). Red flour beetle, T. castaneum (Herbst) is one of the major insect pests of stored grains with cosmopolitan distribution (Ghizdavu and Deac 1994, Desimpelaere 1996, Abro 1996, Wong et al 1996 and Hulasare et al 2003). Although, T.castaneum is considered a pest of flour and other milled cereal products and is also considered as a secondary pest in stored wheat (Le Cato 1975, Hamed and Khattak1985, Irshad and Talpur 1993). A single larva can attack 88 grains during its life time which leads to a considerable loss of quality and viability of grain (Atanasov 1978). Apart from loss of weight and quality of food grains, insects of genus Tribolium secrete a variety of toxic quinones which are known to be carcinogenic. Presence of Tribolium species in the food grains give pungent smell and infested flour becomes dirty yellow in colour (El-Mofty et al 1989) which affect baking quality of flour (Flogliazza and Pagani 2003). To prevent the loss during storage, farmers usually rely on synthetic chemical insecticides. Methyl bromide was used as fumigant in past. Its use has been restricted due to ozone layer depletion (Zhang and Van Epenhuijsen 2004).These problems lead to increasingly stringent environment regulation of pesticides (Isman 2006, Pavela 2007). At present there is an urgent need to develop safer, more environmentally friendly and efficient alternatives that have the potential to replace synthetic pesticides. Among the various alternatives, use of natural plant products called allelochemicals offer a new approach for the management of noxious weeds and pests in sustainable manner (Macias et al 2001).Their toxicities as well as repellent effects on the pests were of special interest during the last decade. Plant essential oils are alternative to synthetic pesticides possess insecticidal, ovicidal, repellent and ovipositional activities against various stored product insects (Chiasson et al 2004, Tripathi and Kumar 2007,Tripathi et al 2009, Aboua et al 2010). Secondary metabolites are known to exhibit a broad spectrum of biological activities. Among them, sesquiterpene lactones are most widely distributed in the members of family Compositae. Sesquiterpenes containing α-methylene-γ-lactone moiety have attracted a great deal of interest to explore their role as cytotoxic agents (Liu et al 2008), anticancer agents (Zhang et al 2005), anti-inflammatory agents (Hall et al 1979), antioxidants (Jung et al 2004) and plant growth regulators (Chhabra et al 1998). Due to their ability to undergo a Michael reaction with biological nucleophiles, α-methylene-γ-lactone has been reported to possess biological activity (Macias et al 1996). Due to their biologically active nature, these compounds have been investigated the most for their chemistry, mechanistic pathways, chemical transformations and synthesis (Rodriguez et al 1976). The possibility that they can provide a lead in the search for new plant growth regulators have helped in isolation and partial synthesis of some of the most potent compounds in which structural features other than α-methylene-γ-lactone moiety are significant which keep the field open for further chemical studies. Parthenium hysterophorous L. is rich source of α-methylene-γ-lactone containing sesquiterpenoids. This annual or biennial herbaceous plant originated from tropical America but has spread throughout the world’s tropical areas. It can grow and reproduce itself any time of the year. During a favorable growing season, four or five successive generations of seedlings can emerge at the same site. Low temperature considerably reduces plant growth, mainly flowering and seed production by reducing leaf area index, relative growth rate, net assimilation rate, and leaf area duration (Pandey et al 2003). The weed grows fast and comfortably on alkaline to neutral clay soils. However, its growth is slow and less prolific on a wide range of other soil types (Rezene et al 2005). It has become a serious problem in many parts of the world due to its threat to agricultural activities, biodiversity and human health and has also been labelled as a useless weed. The weed is particularly problematic in India and Australia where it was first noticed in the 1950s and has continued to spread at an alarming rate (Navie et al 1996). In South Africa, the weed first invaded the warmer and wetter eastern parts of the country in the 1880s, and is currently spreading to several prominent game reserves, including Hluhluwe-I Mfolozi and the Kruger National Park (KNP) (Strathie et al 2005). P. hysterophorus is a known invader of disturbed areas such as roadsides, agricultural fields and wastelands (Navie et al 1996). Characteristics that make the weed such an effective invader include tolerance of a wide range of ecological and climatic conditions, a fast growth rate, high fecundity and efficient utilization of resources (Hedge and Patil 1982). The plant, however, is a folk remedy (Towers et al 1977) against various afflictions: 2 SOURCE USES Barbados Flowers and leaves used for inflammation eczema, skin rashes. Cuba Common name Escobar Amarga, medicinal plant, febrifuge, bitter and corroborant (Roig 1953). Gaudeloupe Febrifuge, used for herpes and rheumatic pains. Guadeloupe and Common names Absinthe batard, herbe, a pian, metricaire allude to Martinique cure of female ailments (Duss 1972). Guyana Used for skin eruptions. Jamaica Supposed to be used in resolutive baths and infusions and for treatment of wounds. Country people use it to prepare a decoction for colds and to make a bath for fleas on dogs. The plant is said to contain bitter glucosides. The plant is still used for ‘bush baths’ in the Kingston area and perhaps, elsewhere as well. Trinidad Used, along with other herbs, in the preparation of bush baths for cleansing the skin. Mexico Analgesic properties, particularly in muscular rheumatism. Used by aztecs as remedy against headache and ulcerated sores (Herz et al 1962). U. S. Virgin Used for muscular strains, analgesic, vermifuge and heart trouble. Islands United states In Montgomery, Ala, it was purposed to be efficacious as a skin tonic by older people. The aqueous extracts of this allelopathic weed are important as potential agents to be manipulated for biological control of pathogenic fungi, only when these extracts are used at lower concentrations; whereas, at higher concentrations, a potent increase in biomass production may prove to be beneficial for mass production of mycoherbicides to control the weeds of economically important crops. Parthenin has been reported to be located in various plant parts with especially high concentrations occurring in trichomes on the leaves (Kanchan 1975, McFadyen 1995, Reinhardt et al 2004). On the molecular level, sesquiterpene lactone biosynthesis is regulated at the transcriptional level, and these compounds generally originate from the mevalonic acid pathway. It has been suggested that all terpenes originate from the common precursor, isopentenyldiphosphate. Reinhardt et al (2004) determined that one trichome type in 3

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