Molecular connectivity and hydrophobicity in the study of antifeedant activity of clerodane diterpenoids

Feeding deterrent activities of twelve clerodane diterpenoids towards Tenebrio molitor (Coleoptera: Tenebrionidae) larvae have been correlated using molecular connectivity indexes ( 3 χ c , 4 χ ν c , 0 ΔX) and hydrophobicity constants (log K'w) obtained by reverse-phase liquid chromatography (RPLC). The equations obtained suggest that both the degree of branching and the electronic characteristics of the compounds under study have a dominant role in the observed antifeedant activity. The information obtained from the correlations should be useful in designing more potent analogues

[1]  V. Martín,et al.  Deoxybartemidiolide, a clerodane-type diterpene from Baccharis artemisioides , 1989 .

[2]  Lemont B. Kier,et al.  A Differential Molecular Connectivity Index , 1991 .

[3]  J. Frenz,et al.  Modeling octanol—water partition coefficients by reversed-phase liquid chromatography , 1989 .

[4]  L B Kier,et al.  Structure-activity studies on hallucinogenic amphetamines using molecular connectivity. , 1977, Journal of medicinal chemistry.

[5]  M. Bentley,et al.  Structure‐activity studies of modified citrus limonoids as antifeedants for Colorado potato beetle larvae, Leptinotarsa decemlineata , 1988 .

[6]  C. Horváth,et al.  Surface silanols in silica-bonded hydrocarbonaceous stationary phases : II. Irregular retention behavior and effect of silanol masking , 1981 .

[7]  A. K. Picman Biological activities of sesquiterpene lactones , 1986 .

[8]  T Braumann,et al.  Determination of hydrophobic parameters by reversed-phase liquid chromatography: theory, experimental techniques, and application in studies on quantitative structure-activity relationships. , 1986, Journal of chromatography.

[9]  K. C. Jones,et al.  Grindelane diterpenoid acids from Grindelia humilis: Feeding deterrency of diterpene acids towards aphids , 1981 .

[10]  M. A. Patrick,et al.  A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography. , 1988, Journal of medicinal chemistry.

[11]  T. M. Odell,et al.  Antifeedant diterpenes for the gypsy moth larvae from Kalmia latifolia: isolation and characterization of ten grayanoids. , 1980 .

[12]  S. Ley,et al.  The antifeedant activity of clerodane diterpenoids from Teucrium , 1989 .

[13]  R. Kaliszan High Performance Liquid Chromatographic Methods and Procedures of Hydrophobicity Determination , 1990 .

[14]  H. Wagner,et al.  New furanoid ent-clerodanes from Baccharis tricuneata , 1978 .

[15]  M. Randic Characterization of molecular branching , 1975 .