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Structural analysis reveals the conformation of an antifeedant neo-clerodane diterpene from Teucrium tomentosum, highlighting potential natural insect-control properties.
A neo-clerodane diterpene, 15-hydroxy-15,16-epoxy-6α-neo-cleroda-3,13(16),14-triene-18,19:20,12-diolide, C20H22O6, showing antifeedant activity against lepidopterous pests, has been isolated from Teucrium tomentosum and characterized by NMR and X-ray crystallographic methods. The crystallographic studies reveal that the cyclohexene and cyclohexane rings adopt a half-chair and a chair conformation, respectively. The furan ring exhibits rotational disorder. The molecules in the crystal structure are stabilized by a network of O—H⋯O and C—H⋯O hydrogen bonds.
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Devi et al. (2003) studied this question.
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