13-Deoxyitol A, a new insecticidal isoryanodane diterpene from the seeds of Itoa orientalis
ABSTRACT A new isoryanodane diterpene, 13-deoxyitol A (1), together with a known isoryanodane diterpene, itol A (2), was isolated from the methanol extract of the seeds of Itoa orientalis. Its structure was determined by spectroscopic means. Compounds 1 and 2 showed antifeedant and contact toxic activities against various insect pests.
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ABSTRACT: Background Destructive impacts of insecticides on non targeted populations necessitate the development of an eco friendly pest control method. Streptomyces spp. are rich source of bioactive secondary metabolites which may provide valuable alternatives to chemical insect-control agents as they can be less toxic and readily biodegradable. Because of its potent biocontrol attributes, ethyl acetate extract of Streptomyces hydrogenans DH16, a soil isolate, was tested to assess its anti-insect potential against polyphagous noctuid, Spodoptera litura.ResultsThe secondary metabolites in the ethyl acetate extract of S. hydrogenans DH16 exhibited larvicidal and growth inhibitory activities. The results indicated that highest concentration of 1600 ¿g/ml was significantly effective as 70% larval, 66.66% prepupal and 100% pupal mortality was noticed. The metabolites also prolonged the larval developmental period. The LC50 and LC90 values were 1337.384 and 2070.516 ¿g/ml, respectively for the insect. Negative effects of S. hydrogenans were also observed on development of the insect. Significant decline in adult emergence, adult longevity, fecundity and % hatching was recorded at higher concentrations along with morphological abnormalities as compared to control. Significant decrease in relative growth and consumption rate, efficiency of ingested and digested food and increase in approximate digestibility in larvae reared on diet supplemented with ethyl acetate extract accounts for the toxic as well as anti-nutritive nature of extract.Conclusion Secondary metabolites in the fermentation broth from S. hydrogenans were toxic to the larvae at higher concentrations whereas lower concentrations significantly reduced the reproductive potential of S. litura. Therefore, these metabolites show considerable potential for incorporation in pest management programmes as new biopesticidal formulation.BMC Microbiology 08/2014; 14(1):227. DOI:10.1186/s12866-014-0227-1 · 2.98 Impact Factor
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ABSTRACT: Three new diterpenoids with unprecedented carbon skeletons, cinncassiols F (1) and G (2) and 16-O-β-d-glucopyranosyl-19-deoxycinncassiol G (3), a new isoryanodane diterpenoid, 18-hydroxyperseanol (4), six known isoryanodane diterpenoids, 5–10, and a known ryanodane diterpenoid, 11, were isolated from the stem bark of Cinnamomum cassia. Compound 1 possesses an 11,13:12,13-diepoxy-6,11-epoxy:12,13-disecoisoryanodane diterpenoid skeleton bearing ketal and hemiketal functionalities, whereas compounds 2 and 3 feature an 11,12-secoisoryanodane diterpenoid skeleton with an 11,6-lactone moiety. The structures of the four new diterpenoids, 1–4, and their absolute configurations were established using HRESIMS, NMR, ECD, single-crystal X-ray diffraction, and chemical methods. Compounds 2 and 11 significantly inhibited the proliferation of murine T cells induced by ConA.Journal of Natural Products 08/2014; 77(8):1948–54. DOI:10.1021/np500465g · 3.95 Impact Factor
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ABSTRACT: BACKGROUND: Considerable attention has been paid to actinomycetes, especially the secondary metabolites obtained from Streptomyces species, as the best alternatives to chemicals as biological control agents for polyphagous pests such as Helicoverpa armigera and Spodoptera litura. On the basis of their novel biocontrol attributes, novel polyketide metabolite isolated from marine Streptomyces sp. AP-123 exhibited significant antifeedant, larvicidal and growth inhibitory activities against polyphagous pests. RESULTS: Leaf disc no-choice method was used for the bioassay. We reported that the polyketide metabolite exhibited significant antibacterial and antifungal activity against Gram positive, Gram negative bacteria and filamentous fungi. The polyketide metabolite presented significant antifeedant activities against H. armigera (78.51%) and S. litura (70.75%) at 1000 ppm concentration. The metabolite also exhibited high larvicidal activities against H. armigera (63.11%) and S. litura (58.22%) and the LC50 values were 645.25 ppm for H. armigera and 806.54 ppm for S. litura. The metabolite also prolonged the larval--pupal duration of the insects at all the tested concentrations. CONCLUSIONS: The activities of the polyketide metabolite were concentration dependent for both the insects therefore it could be used as an agent to prepare new pesticidal formulations.BMC Microbiology 05/2013; 13(1):105. DOI:10.1186/1471-2180-13-105 · 2.98 Impact Factor