13-Deoxyitol A, a new insecticidal isoryanodane diterpene from the seeds of Itoa orientalis

Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University, Wushan, Guangzhou, People's Republic of China.
Fitoterapia (Impact Factor: 2.35). 04/2009; 80(5):286-9. DOI: 10.1016/j.fitote.2009.03.006
Source: PubMed


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 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 insect bioassay. 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.
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    ABSTRACT: Covering: January 2009 to December 2010.
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    ABSTRACT: Three new phenolic constituents, itolide A (1), itolide B (2), itoside P (3), and 1D-3-deoxy-3-hydroxymethyl-myo-inositol (4), which is described herein for the first time as a natural product, were isolated along with four other known compounds (5 to 8) from the methanol extract of the seeds of Itoa orientalis Hemsl by the activity-guided fractionation. Their structures were determined by spectroscopic means. Compounds 1 to 8 exhibited antifungal activities against Sclerotium rolfsii with IC₅₀ values ranging from 60.12 to 240.00 μM and against Rhizoctonia solani with IC₅₀ values ranging from 45.34 to 233.14 μM, respectively, and compounds 1, 2, 5 exhibited cytotoxic activity against Tn5B1-4 insect cell line with EC₅₀ values of 203.68, 93.41 and 40.37 μM, respectively.
    No preview · Article · Dec 2011 · Fitoterapia
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