Diterpenes from Salvia broussonetii Transformed Roots and Their Insecticidal Activity

• Published in: Journal of agricultural and food chemistry Vol. 53; no. 13; pp. 5200 - 5206
• Main Authors: Fraga, Braulio M, Díaz, Carmen E, Guadaño, Ana, González-Coloma, Azucena
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 29.06.2005; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Animals; antifeedants; antifeeding activity; Biological and medical sciences; biosynthesis; Chemistry; Chemistry, Applied; CHO Cells - drug effects; Coleoptera; Control; Cricetinae; Diterpenes - isolation & purification; Diterpenes - toxicity; diterpenoids; Food Science & Technology; Fundamental and applied biological sciences. Psychology; genetic transformation; hairy root culture; insecticidal properties; Insecticides - isolation & purification; Integrated pest control; Leptinotarsa decemlineata; Life Sciences & Biomedicine; pesticidal plants; Physical Sciences; Phytopathology. Animal pests. Plant and forest protection; Plant Roots - chemistry; Protozoa. Invertebrates; Rhizobium rhizogenes; roots; Salvia; Salvia - chemistry; Salvia broussonetii; Science & Technology; Spodoptera; Spodoptera littoralis; tissue culture; ANTIOXIDANT ACTIVITY; LABIATAE; hairy root cultures; iguestol; COMPONENTS; diterpenes; TRITERPENES; TERPENOIDS; antifeedants; ICETEXANE; Salvia broussonetii; brussonol; ABIETANE DITERPENOIDS; COVARIANCE; CULTURES; cytotoxicity; CONSTITUENTS; Hairy root; Insecticide; Root; Pesticides; Cytotoxicity; Plant part; Labiatae; Dicotyledones; Angiospermae; Antifeedant; Diterpene; Spermatophyta; Salvia
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf058045c

The new diterpenes brussonol (1) and iguestol (6α,11-dihydroxy-12-methoxy-abieta-8,11,13-triene) (2) with an icetexane and a dehydroabietane skeleton, respectively, have been isolated from hairy root cultures of Salvia broussonetii. Other previously known diterpenes, 7-oxodehydroabietane, 11-hydroxy-12-methoxyabietatriene, taxodione, inuroyleanol, ferruginol, deoxocarnosol 12-methyl ether, cryptojaponol, pisiferal, sugiol, isomanool, 14-deoxycoleon U, 6α-hydroxydemethylcryptojaponol, demethylsalvicanol, and demethylcryptojaponol, were also obtained from these roots. The insect antifeedant and toxic effects of several of these compounds were investigated against the insect pests Spodoptera littoralis and Leptinotarsa decemlineata. Additionally, their comparative cytotoxic effects were tested on insect Sf9 and mammalian CHO cells. Demethylsalvicanol (4) was a moderate antifeedant to L. decemlineata, whereas brussonol (1) was inactive. 14-Deoxycoleon U (15) was the strongest antifeedant, whereas demethylcryptojaponol (11) was toxic to this insect. None of these compounds had antifeedant or negative effects on S. littoralis ingestion or weight gains after oral administration. Demethylcryptojaponol (11) was cytotoxic to mammalian CHO and insect Sf9 cell lines, followed by the icetexane derivative brussonol (1), with moderate cytotoxicity in both cases. The remainder of the test compounds showed a strong selective cytotoxicty to insect Sf9 cells, with demethylsalvicanol (4) being the most active. Keywords: Salvia broussonetii; hairy root cultures; diterpenes; brussonol; iguestol; antifeedants; cytotoxicity