Hydroxygeranyllinalool Glycosides from Tobacco Exhibit Antibiosis Activity in the Tobacco Budworm [Heliothis virescens (F.)]

• Published in: Journal of agricultural and food chemistry Vol. 45; no. 6; pp. 2299 - 2308
• Main Authors: Snook, Maurice E, Johnson, Albert W, Severson, Ray F, Teng, Quincy, White, Robert A, Sisson, Verne A, Jackson, D. Michael
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.06.1997; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Agronomy. Soil science and plant productions; Biological and medical sciences; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; Chemistry; Chemistry, Applied; COMPOSICION QUIMICA; COMPOSITION CHIMIQUE; DITERPENOIDE; DITERPENOIDS; DITERPENOS; ESTRUCTURA QUIMICA; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Genetics and breeding of economic plants; INSECTICIDAL PROPERTIES; INSECTICIDAS; INSECTICIDE; INSECTICIDES; Life Sciences & Biomedicine; Pest animals; Pest resistance; Physical Sciences; Science & Technology; STRUCTURE CHIMIQUE; Varietal selection. Specialized plant breeding, plant breeding aims; 16-hydroxygeranyllinalool glycosides; Nicotiana; LEAVES; COMPONENTS; FEMALES; HOST; diterpene glycosides; MULTIPLE QUANTUM NMR; SPECTROSCOPY; VOLATILES; LEPIDOPTERA; NOCTUIDAE; Heliothis virescens (F); antibiosis; Entomology; Insecta; Stimulant plant; Biochemistry; Pest; Phytophagous; Dicotyledones; Insect resistance; Angiospermae; Carbohydrate; Chemical composition; Glycoside; Solanaceae; Terpenoid; Heliothis virescens; Biochemical analysis; Genotype; Plant leaf; Antibiosis; Biological activity; Biological compound; Animal plant relation; Arthropoda; Genetic improvement; Lepidoptera; Plant origin; Pest resistance; Spermatophyta; Noctuidae; Invertebrata; Heteroside
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf960748u

Leaves of Tobacco Introduction TI-165 were found to be resistant to tobacco budworm [Heliothis virescens (F.)] attack. HPLC profiles of leaf extracts showed that TI-165 had relatively high levels of two components (A and B) that were absent in susceptible varieties. Compounds A and B were isolated from TI-165 by a combination of preparative C18, silicic acid column, and centrifugal thin-layer chromatography. They were identified as diterpene glycosides:  compound A, 16-hydroxygeranyllinalyl-3-O-[α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranoside-16-O-[α-l-rhamnopyranosyl(1→6)]-β-d-glucopyranoside; compound B, 16-hydroxygeranyllinalyl-3-O-[α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranoside-16-O-[α-l-rhamnopyranosyl(1→6)]-[α-l-rhamnopyranosyl(1→4)]-β-d-glucopyranoside (hydroxygeranyllinalool glycosides). Budworm bioassays with whole tobacco leaves and purified mixtures of A and B showed significant correlation between larval weights and levels of A and B. HPLC analyses of freeze-dried leaves of 68 Nicotiana species indicated that 26 species had high levels of diterpene glycosides identical to or related to A and B. Keywords: Nicotiana; Heliothis virescens (F.); antibiosis; 16-hydroxygeranyllinalool glycosides; diterpene glycosides