New Skeletal Sesquiterpenoids, Caprariolides A−D, from Capraria biflora and Their Insecticidal Activity

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2000-11, Vol.63 (11), p.1515-1518
• Main Authors: COLLINS, Dwight O., GALLIMORE, Winklet A., REYNOLDS, William F., WILLIAMS, Lawrence A. D., REESE, Paul B.
• Format: Article
• Language: English
• Subjects: Biological and medical sciences; Capraria biflora; Chemical control; Control; Cylas formicarius; Fundamental and applied biological sciences. Psychology; General pharmacology; Insecticides - isolation & purification; Insecticides - pharmacology; Ipomoea; Magnetic Resonance Spectroscopy; Mass Spectrometry; Medical sciences; Molecular Conformation; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Phytopathology. Animal pests. Plant and forest protection; Plant Extracts - analysis; Plant Leaves - chemistry; Plant Stems - chemistry; Plants, Medicinal - chemistry; Protozoa. Invertebrates; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; sesquiterpenoids; West Indies
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np000280w

Four structurally novel isomeric sesquiterpenes have been isolated from the aerial parts of Capraria biflora. Caprariolides A (1), B (2), C (3), and D (4) have been determined by NMR spectroscopy experiments to be the (3S,5S,9R), (3R,5S,9R), (3R,5R,9R), and (3S,5R, 9R) isomers of 7-(furan-3'-yl)-3,9-dimethyl-1-oxaspiro[4. 5]dec-6-en-2-one, respectively. Both 1 and 2 were found to exhibit insecticidal activity against adult Cylas formicarius elegantulus, one of the most destructive insect pests of the sweet potato, Ipomoea sp.