International Biodeterioration & Biodegradation 65 (2011) 877e882 Contents lists available at ScienceDirect International Biodeterioration & Biodegradation journal homepage: www.elsevier.com/locate/ibiod Efficacy of karanjin and phorbol ester fraction against termites (Odontotermes obesus) Monica Verma, Subhalaxmi Pradhan, Satyawati Sharma*, S.N. Naik, Rajendra Prasad Center for Rural Development and Technology, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India a r t i c l e i n f o a b s t r a c t Article history: Received 25 February 2011 Received in revised form 25 May 2011 Accepted 28 May 2011 Available online 23 July 2011 The non-edible oil seeds of Jatropha curcas (physic nut) and Pongamia pinnata (karanja) contain some toxic components (phorbol esters in J. curcas and karanjin in P. pinnata), which may be used as biopesticides. In this study, the active components of J. curcas and P. pinnata oil were extracted and their efficacy against the termites Odontotermes obesus (Rambur), was tested. The phorbol ester fraction of J. curcas and karanjin of P. pinnata oil were found to be effective against termites. A mortality rate of 100% was achieved in 6 h with karanjin and in 12 h with phorbol ester fraction. The LC50 levels of karanjin and phorbol esters fractions were 0.038 and 0.071 g ml1, respectively, after 24 h at a 95% (0.05) confidence limit. Ó 2011 Elsevier Ltd. All rights reserved. Keywords: Jatropha curcas Pongamia pinnata Phorbol esters Karanjin Termite 1. Introduction Termites are a serious menace to both plants and wooden structures. These are the problematic pests threatening agriculture and urban environment. They cause significant losses to annual and perennial crops and damage to wooden components in buildings, especially in the semi-arid and sub-humid tropics (Verma et al., 2009). Chemical control is the only method of termite control so far. The active component of botanicals having anti-termitic properties can be extracted to prepare potent biopesticidal formulations. Among various non-edible oil seed crops, Jatropha curcas and Pongamia pinnata are widely used for biodiesel production. They can be cultivated on any type of soil and have a low moisture demand. P. pinnata, commonly known as karanja, is a forest tree belonging to the family Leguminosae. It grows abundantly along the coasts and riverbanks in Myanmar and in all parts of India, particularly in Tamil Nadu, Andhra Pradesh, and Karnataka. It possesses applications in agriculture and environmental management. The various parts of the P. pinnata tree have been used for the treatment of tumors, skin diseases, abscesses, painful rheumatic * Corresponding author. Center for Rural Development and Technology, Indian Institute of Technology Delhi, III block, Hauz Khas, New Delhi 110016, India. Tel.: þ91 11 26591116; fax: þ91 11 26591112. E-mail address: [email protected] (S. Sharma). 0964-8305/$ e see front matter Ó 2011 Elsevier Ltd. All rights reserved. doi:10.1016/j.ibiod.2011.05.007 joints, wounds, ulcers, diarrhea, etc. (Shoba and Thomas, 2001; Meera et al., 2003). The seed contains 27e39% oil, 20e30% protein, and a group of furano-flavonoids that constitutes 5e6% by weight of the oil (Bringi, 1987). The major furano-flavonoids present in the seeds are karanjin (1.25%) and pongamol (<1%). Karanjin is 3-methoxy furanoflavone and pongamol is furanodiketone. The insecticidal, nematicidal, antifungal, antibacterial, and antiviral activities of P. pinnata have been widely tested (Elanchezhiyan et al., 1993; Baswa et al., 2001; Simin et al., 2002; Kesari et al., 2010). Karanja oil and karanjin have been reported to contain piscicidal (Rangaswamy and Seshadri, 1941) and insecticidal properties against insects such as cockroaches, aphids, houseflies, and nematodes (Osmani and Naidu, 1956; Singh, 1966; Parmar, 1969; Parmar and Gulati, 1969; Mishra and Prasad, 1973). J. curcas, a tropical plant belonging to the family Euphorbiaceae, is cultivated mainly as a hedge plant in many Asian and African countries. It is a multipurpose, drought-resistant, perennial plant that is an important source for the production of biodiesel (Kumar and Sharma, 2008). The seed contains approximately 24.6% crude protein, 47.3% crude fat, and 5.54% moisture content (Akintayo, 2004). However, despite their advantages, the seeds are reported to have anti-nutritional factors such as phorbol esters, saponin, phytate, trypsin inhibitor, and cyanogenic glucosides (Makkar et al., 1997; Rakshit et al., 2008). Extracts from J. curcas seeds and leaves possess molluscicidal, insecticidal, and fungicidal properties (Nwosu and Okafor, 1995; Liu et al., 1997; Solsoloy and Solsoloy, 878 M. Verma et al. / International Biodeterioration & Biodegradation 65 (2011) 877e882 1997). The high concentration of phorbol esters present in J. curcas seeds has been identified as the main component responsible for the toxicity (Adolf et al., 1984; Makkar et al., 1997). The purpose of this study was to extract and identify the phorbol esters fraction from Jatropha and the karanjin from karanja and to test their efficacy against termites. 2. Materials and methods 2.1. Procurement of sample The J. curcas and P. pinnata seeds were collected from Gujarat, India, and the IIT Delhi campus, India, respectively. The samples were cleaned manually to remove all foreign materials. The seeds were initially dried in the sun for two days and then in a hot-air oven at 80 C. The samples were weighed after cooling in a dessicator repeatedly until constant weight was attained after 24 h. 2.2. Extraction of oil from seeds Seed kernels (50 g) of both karanja and jatropha were ground separately for 1 min and sieved through a 2-mm sieve. For oil content determination (AOAC, 1984) the ground kernels were extracted in soxhlet apparatus using petroleum ether (boiling point 60e80 C). The extract was concentrated by rotary evaporator and the oil was cooled and weighed. 2.3. Extraction of toxic fraction and estimation of phorbol ester by HPLC Extraction of the phorbol esters fraction (Gandhi et al., 1995) from J. curcas oil was done by the solventesolvent extraction method. The seed oil was extracted in a methanolewater (9:1) mixture using a separating funnel. The combined methanolewater layer was evaporated in a rotary evaporator. A viscous oily fraction was separated from the aqueous solution after concentration. It was again extracted with diethyl ether. The combined ether layer was washed with water and evaporated. A brown viscous mass was obtained and thin layer chromatography (TLC) of that fraction was done for qualitative determination of toxic constituents. The phorbol esters fraction of oil was dissolved in tetrahydrofuran (THF) for determination of phorbol esters by HPLC. The phorbol esters fraction of J. curcas seed oil was analyzed with a high-performance liquid chromatography (Waters 600 HPLC) system equipped with a reverse phase C18 column (Waters Spherisorb, 5 mm, 250 mm 4 mm i.d.), a Waters 2998 photodiode array detector, a Waters 600 HPLC quaternary pump, a Waters inline degasser, and Empower software. The column temperature was controlled at 25 C and the flow rate was 1.3 ml min1. The solvents used were 1.75 ml Ophosphoric acid (85%) in 1 L distilled water (A) and acetonitrile (B). All solvents were filtered and degassed by a Waters inline degasser. The gradient used was as follows: 0e10 min, 60% A and 40% B; 10e40 min, 50% A and 50% B; 40e55 min, 25% A and 75% B; 55e60 min,100% B and then the column was adjusted to the starting condition (60% A and 40% B). The peaks were integrated at 280 nm and the results were expressed as equivalent to phorbol-12-myristate 13-acetate (Sigma Chemicals), which appeared at 51 min. Each analysis was conducted in triplicate. 2.4. Extraction of karanjin from P. pinnata The crude karanjin fraction was extracted from P. pinnata oil by the solventesolvent extraction method as described by Gandhi and Cherian (2000). One hundred grams of the oil was dissolved in 100 ml of petroleum ether (40e60 C) and extracted repeatedly with 100 ml of aqueous methanol (methanolewater 9:1 v/v) until the alcoholic layer was colorless. The combined methanolewater layer was concentrated in a rotary evaporator and a viscous paste was obtained. The aqueous methanolic extract of P. pinnata oil was purified by column chromatography. The adsorbent silica gel of 100e200 mesh was packed in the glass column by preparing the slurry in hexane. The slurry of extract mixed with silica gel was placed above the adsorbent and the column was initially eluted in n-hexane and the polarity of the solvent was increased by adding ethyl acetate. The eluents were collected at frequent intervals and the purity was checked by TLC. The fraction obtained from column chromatography containing karanjin was crystallized in acetone and pure crystals were obtained by vacuum filtration and repeated washing with cold acetone (stored at 4 C). The compound was identified by physical characteristics and spectral data. The 1H NMR (nuclear magnetic resonance) spectra of the compound were carried out on a Brucker 300-MHz instrument (Brucker DPX 300, Rheinstetten, Germany). 2.5. Toxicological studies on termites 2.5.1. Test insect Adult workers of the subterranean termite Odontotermes obesus were collected from the Indian Institute of Technology, Delhi campus, 0.50 0.40 Phorbol esters AU 0.30 0.20 0.10 0.00 0.00 5.00 10.00 15.00 20.00 25.00 30.00 35.00 40.00 45.00 50.00 55.00 60.00 65.00 Minutes Fig. 1. The figure represents the HPLC chromatogram of phorbol esters. The phorbol esters (Four peaks) appeared between retention time (tR) 40e46 min. The estimation of phorbol ester content was done by using Waters 600 HPLC system equipped with a reverse phase C18 column (Waters Spherisorb, 5 mm, 250 mm 4 mm i.d.), a photodiode array detector. The column temperature was kept at 25 C and the flow rate was 1.3 ml min1. The solvents used were 1.75 ml O-phosphoric acid (85% v/v) in 1 L distilled water (A) and acetonitrile (B). M. Verma et al. / International Biodeterioration & Biodegradation 65 (2011) 877e882 879 2.5.2. Bioassay The no-choice bioassay method (Kang et al., 1990) was employed to evaluate termiticidal activity. Karanjin and phorbol esters fractions extracted from P. pinnata and J. curcas oil, respectively, were tested for termite mortality at different concentrations, i.e., 0.5, 0.25, 0.05, 0.025, and 0.005 g ml1. Dilution of karanjin and phorbol esters fractions was done by using acetone and diethyl ether, respectively. A moistened, extract-treated cellulose filter paper disc (dia 4.5 cm) was placed at the bottom of the petri plate (dia 5 cm). Ten termites were introduced into each petri plate. Three replicates were made for each concentration and 200 ml extract of each concentration was loaded onto the filter paper. A filter paper disc treated with solvent only was used as the control. The solvent was removed from treated filter paper by air-drying at room temperature. In blank controls, discs were treated with distilled water only. A starvation control was also set up (Blaske and Hertel, 2001) in petri plates containing only sand, to observe whether the termites were dying of starvation or due to the effect of treatment. In the case of the chemical control, a commonly used termiticide, chlorpyriphos EC 20 (C9H11Cl3NO3PS), was used at the recommended dose. The petri plates with covers were then placed in an incubator at 25 1 C and 80 5% relative humidity. A few drops of water were periodically dripped onto the filter paper disc, which was kept inside the petri plate. The mortality was recorded for 72 h. 1 2 2.5.3. Statistical analysis After 24 h, the LC50 was determined from the data obtained with a concentration range between 0.5 and 0.005 g ml1 using the probit analysis method (Statplus, 2007). Analysis of variance (ANOVA) was performed on all experimental data and means were compared using Duncan’s multi-range test with SPSS 10.0 software. The significance level was p < 0.05. 3. Results and discussion Fig. 2. Thin layer chromatography was done on silica gel coated plate. The plate was developed in solvent system hexane: diethyl ether: acetic acid (85:15:1 v/v). The spots were detected by iodine vapor staining. 3.1. Identification and quantification of phorbol esters and acclimatized for 24 h in laboratory conditions before use (Bhonde et al., 2001). They were maintained at 25 1 C and 80 5% relative humidity in a plastic container with dried pinewood and filter paper as a food source. Phorbol esters are the major toxic constituents present in the active fraction extracted from J. curcas oil. The phorbol esters (four peaks) appeared between 41 and 48 min in the LC analysis (Fig. 1). The quantity of phorbol esters in the present study was 3.17 mg g1 Fig. 3. 1H NMR (Nuclear Magnetic Resonance) analysis was performed on a Bruker 300 MHz (Bruker DPX 300, Rheinstetten, Germany) spectrometer using CDCl3 as solvent and tetramethylsilane (TMS) as internal standard. 880 M. Verma et al. / International Biodeterioration & Biodegradation 65 (2011) 877e882 Table 1 Mortality % of Termite with Karanjin. Treatments % Mortality of termite workers Karanjin (g/ml) 1h 0.5 0.25 0.05 0.025 0.005 Blank control Solvent control Starvation control Chemical controla 46.67 36.67 0.0 0.0 0.0 0.0 0.0 0.0 100.0 3h 4.7b 4.7c 0.0d 0.0d 0.0d 0.0d 0.0d 0.0d 0.0a 53.33 40.0 6.67 0.0 0.0 0.0 0.0 10.0 100.0 6h 4.7b 0.0c 4.7d 0.0e 0.0e 0.0e 0.0e 0.0d 0.0a 100.0 43.33 10.00 6.67 0.0 0.0 0.0 10.0 100.0 12 h 0.0a 4.7b 0.0c 4.7c 0.0d 0.0d 0.0d 0.0c 0.0a 100.0 60.0 33.33 20.00 13.33 0.0 0.0 10.0 100.0 24 h 0.0a 8.2b 4.7c 8.2d 4.7de 0.0f 0.0f 0.0e 0.0a 100.0 96.67 43.33 26.67 20.00 0.0 0.0 16.67 100.0 48 h 0.0a 4.7a 12.4b 4.7c 8.2c 0.0d 0.0d 4.7c 0.0a 100.0 100.0 70.0 36.67 23.33 0.0 0.0 16.67 100.0 72 h 0.0a 0.0a 8.2b 4.7c 4.7d 0.0e 0.0e 4.7d 0.0a 100.0 100.0 83.33 63.33 36.67 0.0 0.0 20.0 100.0 0.0a 0.0a 4.7b 4.7c 4.7d 0.0f 0.0f 0.0e 0.0a Mean Standard Deviation (SD) on three determinations. Values (means of 3 replicates) in each column not sharing a common letter differ significantly (p < 0.05) from each other (Duncan’s multi-range test). a Chlorpyriphos recommended dose 0.02%. in oil. However, the phorbol esters content has been found to vary from 0.87 to 3.32 mg g1 in different varieties of J. curcas seed (Makkar et al., 1997). Hass and Mittelbach (2000) reported a level of 0.31% of phorbol esters in J. curcas oil, and Aregheore et al. (2003) reported 0.13 mg g1 phorbol esters in J. curcas meal. 3.2. Identification of karanjin Thin layer chromatography of karanjin, isolated from P. pinnata oil, is given in Fig. 2. Karanjin (3-methoxy furano-(20 , 30 :7, 8)-flavone), a colorless crystal with a melting point of 162 C, isolated by column chromatography, was confirmed from the physical characteristics and the 1H NMR spectral data (Fig. 3) and was found to be in accordance with the reported values (Siddiqui and Zaman, 1998). 3.3. Toxicological studies The LC50 of karanjin and phorbol ester fractions was found to be 0.038 g ml1 and 0.071 g ml1, respectively, at 24 h and a 95% (0.05) confidence limit. Table 1 shows the toxicity of different concentrations of karanjin on O. obesus. One hundred percent mortality of termites was observed within 6 h with 0.5 g ml1 of karanjin, while in the case of a 0.25 g ml1 concentration, 100% mortality was achieved in 48 h. At a level of 0.005 g ml1, karanjin was not very effective, showing only 13.33% mortality in 12 h. In a blank control, all the termites were alive even after a 72-h period. Similarly, in the case of a solvent control, no mortality occurred. In a starvation control, only 20% mortality was seen in 72 h. In a chemical control, all the termites died within an hour. Karanjin has been reported to suppress the ecdysone hormone and to inhibit cytochrome P450 in insects and mites (Copping, 2004). The cytochrome P450 mono-oxygenases of insects have a significant role in growth, development, insecticide resistance, tolerance to plant toxins, and metabolism of endogenous compounds (Hodgson, 1985b; Scott et al., 1998; Feyereisen, 1999). The biosynthesis of these enzymes is induced by the toxins in the food (Berenbaum et al., 1990; Frank and Fogleman, 1992; Hung et al., 1995). They metabolize the insecticides by detoxification or by activating a molecule (Wilkinson and Brattsten, 1972; Agosin, 1985; Hodgson, 1985a). This process is so fast in some insects that the insecticide is metabolized long before reaching its molecular targets (Taylor and Feyereisen, 1996) leading to resistance to insecticides. Piperonyl butoxide is the most commonly used P450 mono-oxygenase inhibitor (Berge et al., 1998). Karanjin was examined as a P450 inhibitor along with other flavones in the housefly and found to be the most potent inhibitor of this enzyme (Scott et al., 2000). The mixture of karanja oil and piperonyl butoxide was tested as pyrethrum synergists against the housefly and the mixture was observed to be more economical than piperonyl butoxide used alone (Parmar, 1974). These studies suggest that suppression of the ecdysone hormone and inhibition of the cytochrome P450 enzyme in insects might be the reason for the bioactivity of karanjin against termites. The results of this study pertaining to the biopesticidal value of karanjin are also supported by others who have observed the effectiveness of karanja oil and karanjin against the mosquito (Renapurkar et al., 2001), cockroach (Osmani and Naidu, 1956; Parmar and Gulati, 1969), housefly (Osmani and Naidu, 1956), and mustard aphid (Singh, 1966). Karanja cake completely controlled the root knot diseases of tomato in larger doses (Singh, 1965). The synergistic combination of Pongamia glabra and Anona squamosa in equal proportion was toxic to the mosquito larvae of the three prominent vectors, namely Anopheles stephensi, Aedes aegypti, and Culex quinquefasciatus (George and Vincent, 2005). The toxicity of the phorbol esters fractions against termites is shown in Table 2. The highest concentration of the phorbol esters Table 2 Mortality % of Termite with Phorbol esters. Treatments % Mortality of termite workers Phorbol esters fraction (g/ml) 1h 3h 6h 12 h 24 h 48 h 72 h 0.5 0.25 0.05 0.025 0.005 Blank control Solvent control (Methanol) Starvation control Chemical controla 36.67 4.7b 10.0 0.0c 0.0 0.0d 0.0 0.0d 0.0 0.0d 0.0 0.0d 0.0 0.0d 0.0 0.0b 100.0 0.0a 50.0 0.0b 26.67 4.7c 0.0 0.0e 0.0 0.0e 0.0 0.0e 0.0 0.0e 0.0 0.0e 10.0 0.0d 100.0 0.0a 63.33 4.7b 36.67 4.7c 6.67 4.7d 0.0 0.0e 0.0 0.0e 0.0 0.0e 0.0 0.0e 10.0 0.0b 100.0 0.0a 100.0 0.0a 46.67 4.7b 16.67 9.4c 13.33 4.7c 0.0 0.0d 0.0 0.0d 0.0 0.0d 10.0 0.0c 100.0 0.0a 100.0 0.0a 76.67 4.7b 26.67 9.4c 20.0 0.0cd 13.33 4.7de 0.0 0.0f 0.0 0.0f 10.0 0.0e 100.0 0.0a 100.0 0.0a 86.67 4.7b 36.67 9.4c 33.33 4.7c 20.0 0.0d 0.0 0.0e 0.0 0.0e 13.33 4.7d 100.0 0.0a 100.0 0.0a 100.0 0.0a 66.67 9.4b 50.0 0.0c 33.33 4.7d 0.0 0.0f 0.0 0.0f 20.0 0.0e 100.0 0.0a Mean Standard Deviation (SD) on three determinations. Values (means of 3 replicates) in each column not sharing a common letter differ significantly (p < 0.05) from each other (Duncan’s multi-range test). a Chlorpyriphos recommended dose 0.02%. M. Verma et al. / International Biodeterioration & Biodegradation 65 (2011) 877e882 fraction (0.5 g ml1) showed 100% mortality of O. obesus in 12 h. However, with 0.25 g ml1, maximum mortality (100%) was achieved in 72 h. With 0.05, 0.025, and 0.005 g ml1 concentrations of the phorbol esters fraction 66.67, 50, and 33.33% mortality was seen in 72 h. Chemical control was found to be most effective, showing 100% mortality in 1 h. No mortality was detected in blank and solvent controls throughout the test period (72 h) while in the case of the starvation control, 20% mortality was observed. The toxicity of phorbol esters may be due to its interference with the normal functions of the metabolic activities of insects (Goel et al., 2007). The results are in agreement with Acda (2009), where J. curcas oil was tested against Philippine milk termites (Coptotermes vastator Light). The study revealed that J. curcas oil showed an antifeedant effect, reduced tunneling activity, repellent activity, and increased termite mortality. The toxic effects of J. curcas oil and phorbol esters were also reported by Solsoloy and Solsoloy (1997); the emulsifiable concentrate formulation of crude oil was toxic against corn weevil (Callosubruchus chinensis), bean weevil (Sitophilus zeamays), and housefly (Musca domestica). The LD50 of the formulation were determined to be 0.91% and 1.92% for corn weevil and bean weevil, respectively. In the case of the housefly, chronic toxicity was observed. The pupae that developed from the treated maggots were smaller than normal ones, which led to very small adults with wrinkled wings, resulting in a 40e60% population reduction. Solsoloy (1993) suggested J. curcas as a promising alternative to deleterious chemicals after testing the oil on cotton insect pests, cotton bollworm (Helicowerpa armigera), and cotton flower weevil (Amorphoidea lata), and also reported that the oil did not affect the population of beneficial insects when compared with chemical spray. The crude oil was found to be more efficient than the methanolic extract to control the sorghum pests stem borers (Sesamia calamistis and Busseola fusca) (Mengual, 1997). It has also been reported that a significant increase in anti-termitic activity may be achieved by enhancing the toxic components of jatropha through extraction using organic solvents (Liu et al., 1997; Rug et al., 1997; Acda, 2009). 4. Conclusions Both karanjin and phorbol ester fractions were found to be toxic against termites (O. obesus), with karanjin being the more effective. 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