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Insecticidal and Cytotoxic Agents of Thevetia Thevetioides Seed

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Insecticidal and Cytotoxic Agents of Thevetia Thevetioides Seed Purchased by U. S. Dept. 01 AgrlcultlUe for Official Use Neriifolin and 2' -Acetylneriifolin: Insecticidal and Cytotoxic Agents of 1 Thevetia thevetioides Seeds ,2 J. L. McLAUGHLIN, B. FREEDMAN, R. G. POWELL, AND C. R. SMITH, JR. Northern Regional Research Center, Agric. Res., SEA, USDA, Peoria, IL 61604 Reprillted from the JOURNAL OF ECONOMIC ENTOMOLOGY Neriifolin and 2' -Acetylneriifolin: Insecticidal and Cytotoxic Agents of 1 Thevetia thevetioides Seeds ,2 J. L. McLAUGHLIN, B. FREEDMAN, R. G. POWELL, AND C. R. SMITH, JR. Northern Regional Research Center, Agric. Res., SEA, USDA, Peoria, IL 61604 ABSTRACT J. Ecan. Enlama!. 73: 398-402 (1980) A bioassay procedure utilizing the European com borer, Ostrinia nubilalis (Hiibner), has been used to guide the phytochemical fractionation of active extracts of the seeds of a yellow oleander, Thevetia thevetioides (HBK.) K. Schum. (Apocynaceae). The known cardiotonic glycosides, neriifolin and 2'-acetylneriifolin, were crystallized as the active insecticidal agents, giving LDso determinations of 30 ppm and 192 ppm, respectively, when incorporated into the com borer diet. These compounds also exhibited cytotoxic activities of 2.2x 10-2 and 3.3 x 10-2 fLg/ml, respectively, in the KB (human nasopharynx epidermoid carcinoma) in vitro system. The glucoside of f3-sitosterol also was isolated but it lacked insecticidal activity. Freedman et al. (1979) reported that ethanol extracts Materials and Methods of the seeds of a Mexican yellow oleander, Thevetia Plant Material thevetioides (HBK.) K. Schum. (Apocynaceae) were lethal (100% larval mortality) when incorporated into Seeds of T. thevetioides were collected in September the diet of the European com borer, Ostrinia nubilalis 1977 in Mexico for the USDA Medicinal Plant Re­ (Hiibner). sources Laboratory through which voucher specimens Toxicity of Thevetia species to higher animals, in­ (B-171053, PR-48977, colI. no. ES-106) are preserved. cluding humans, is well documented (Kingsbury 1964) The seeds were pulverized in a Wiley mill. and is attributed to cardiotonic glycosides (Zechner European Com Borer Bioassay 1966) whose steroidal aglycone is digitoxigenin (Cruz Com borer larvae were reared from eggs supplied by et al. 1977). In many tropical areas of the world, where the Com Insects Res. Unit, USDA, Ankeny, lA. Bioas­ the plants are both endemic and naturalized, Thevetia says were performed, essentially as described by Freed­ species have several folkloric medicinal uses (Watt and man et al. (1979), using plastic jelly cups each contain­ Breyer-Brandwijk 1962), including the treatment of tu­ ing five 7-day-old larvae and 4.0±0.1 g of diet mixed mors (Hartwell 1967, Martinez 1969). with the appropriate dose of treatment material. Crude In India, extracts of Thevetia leaves are used as a extracts were tested at 40 mg/cup, the 1st column frac­ pediculicide (Atal and Kapur 1977); in Mexico, the tions at 5 mg/cup, subsequent column fractions at 2 mg/ milky juice is applied to the mange (itch mites) (Mar­ cup, mother liquors at 1 mg/cup, and crystalline isolates tinez 1969); and powdered seeds of Thevetia act as a at a range of 2-0.03125 mg/cup. protectant of stored seeds against insect infestations Each treatment was replicated 4 times. Mortalities (Pandey et al. 1977). Several papers report effectiveness were determined at 5 and 9 days by counting survivors. as well as ineffectiveness of Thevetia powders and ex­ Activities are expressed as percent mortality at 9 days tracts against a variety of insect species (McIndoo 1945, adjusted for control mortality by Abbott's formula; con­ Jacobson 1958, 1975, Deshmukh and Borle 1975). trols were run concurrently for the various solvents Without reporting experimental data, Gattefosse (1949) (acetone, ethanol, or petroleum ether) used to apply the attributed t'le insecticidal activity of T. neriifolia Juss. treatments to the diet. Estimations of LDso values were (synonym: T. peruviana (Pers.) Schum.) to the glyco­ made using the standard probit analysis ofDaum (1970). side, thevetin, and to another unidentified material of even greater toxicity; he also proposed that these ma­ Cytotoxicity Bioassay terials be developed as a new agricultural insecticide. Activity of preliminary extracts and crystalline com­ Our purpose was to isolate and characterize the in­ pounds against KB cells in vitro was determined by secticidal compound(s) of Thevetia. The com borer contractors for the National Cancer Institute employing bioassay was used as a guide to the phytochemical frac­ standard protocols (Geran et al. 1972). Isolated com­ tionation of the active ethanol extracts of the seeds of pounds are considered active if the EDso is ~4 fLg/mI. T. thevetioides. Concurrently, certain extracts and frac­ Chromatographic Methods tions also were found to exhibit significant cytotoxic Column chromatography was performed in appropri­ activity against KB (human nasopharynx epidermoid ately sized columns using silica gel (Hi-Flosil, 60/200 carcinoma) cells (Geran et aI. 1972), and we wished to mesh, Applied Science Laboratories, State College, PA) determine if the final insecticidal isolates also might be packed in chloroform slurries. Column fractions were the active cytotoxic agents. assayed with TLC on silica gel (silica gel 60 F254 , 0.25­ mm precoated plates, EM Laboratories, Elmsford, NY). The TLC solvent system was chloroform-methanol (9:1), ~on of firm names or trade products does not imply endorsement or and the developed chromatograms were visualized with recommendation by the USDA over other fIrms or similar products not mentioned. , Received for publication Jan. 14. 1980. chromic acid-sulfuric acid char (Stahl 1969). 398 June 1980 McLAUGHLIN ET AL.: INSECTICIDAL AND CYTOTOXIC AGENTS OF Thevetia 399 Characterization Methods and 100% methanol in chloroform. A total of ninety 25­ Melting points were determined with a Fisher-Johns ml fractions was collected and combined after TLC. melting point apparatus and are uncorrected. Infrared Significant activities (at 2 mg/cup) were detected in frac­ spectra were recorded in chloroform on a Perkin-Elmer tion 2:20-26 (2.28 g, 54.5%) and fraction 2:27-32 (0.32 model 700 IR spectrometer. 90 MHz IH and proton de­ g,56.7%). coupled 13C nrm spectra were obtained in deuterochlo­ Fraction 2:20-26 (2.27 g) was then chromatographed roform using a Brunker WH-90 instrument with tetra­ on a 2.0x60-cm column of silica gel (42.9 g) developed methylsilane as the internal reference. Authentic samples with 250-ml portions of 0, 0.5, 1.0, 1.5, 2.0, 2.5, 5, of neriifolin and 2'acetylneriifolin were supplied by Dr. 25, and 100% methanol in chloroform. A total of ninety­ Jose Iriarte, Research Division, Syntex SA, Mexico 10, one 25-ml fractions was collected and combined after D.F. Mexico. TLC. The most significant larvicidal activity (at 2 mg/ cup) was found in fraction 3:36-46 (1.50 g, 72.9%). Isolation Procedures and Results Fraction 3:36-46 (1.49 g) was chromatographed on Extraction ofPlant Material a 2.0x60-cm column of silica gel (42.7 g) developed A total of 18.75 kg of the powdered plant material successively with 250-ml portions of chloroform-meth­ was extracted for 6 h with hexane in a large pilot plant anol mixtures containing 0,0.25,0.5,0.75, 1.0, 1.5, Soxhlet extractor, and the inactive hexane extract was 2, 5, and 100% methanol. A total of ninety-one 25-ml discarded. The dried marc was then extracted (Soxhlet) fractions was again collected and combined after TLC for 6 h with ethanol, and the ethanol extract was con­ analysis. The most significant activity (at 2 mg/cup) was densed to a syrup (1.09 kg) under vacuum in a rotary found in fraction 4:57-64 (1.24 g, 87.3%). evaporator. A portion (435.2 g) of the ethanol extract Fraction 4:57-64 crystallized upon standing and was (corn borer activity, 94.0%) was treated with 8 liter of recrystallized from ethyl ether, yielding 0.40 g, mp water and was partitioned 3 times with 8-liter portions 211°-214°C. After further recrystallization, 0.38 g was of chloroform. The freeze-dried residue (204.0 g) from obtained, mp 220°-222°C. This compound was active the aqueous layer was inactive, whereas the syrup re­ with an LD50 of 0.77 mg/cup (192 ppm in the diet, slope maining after vacuum evaporation of the combined chlo­ 0.83) with 95% limits from 0040 to 2.17 mg/cup. The roform layers was very active (100%). activity of the mother liquor (36.5% at 1 mg/cup) was The entire chloroform residue (199.6 g) was parti­ entirely due to the presence of this compound and in­ tioned between hexane and methanol-water (9: I) (750 dicated the absence of more potent compounds in this ml each); each layer was backwashed twice with two fraction. This active crystalline isolate was subsequently 250-ml portions of the respective immiscible solvents. identified as 2'-acetylneriifolin (Fig. 1). The hexane residue (155.9 g) was inactive, whereas the isolation ofNeriijolin from Fractions I :31-34 and methanol-water residue was highly active (100% at 40 1:35-39 mg/cup). Fraction 1:31-34 (8.20 g) was chromatographed on Chromatography ofActive Crude Extract a 4.5x67-cm column of silica gel (205 g) developed The entire methanol-water residue (49.2 g) was chro­ with 500-ml portions of 0,2.5, 5, 7.5, 10, 12.5, 15, matographed on a 6x72-cm column containing 467 g 25, 50, and 100% methanol in chloroform. A total of ofsilica gel. Development was made with one-liter por­ 100 fifty-ml fractions was collected and combined ac­ tions of solvent mixtures containing 0, 5, 10, 15, 25, cording to TLC analyses.
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