Chilocorine: heptacyclic alkaloid from a coccinellid beetle

• Published in: Tetrahedron Vol. 50; no. 8; pp. 2365 - 2372
• Main Authors: McCormick, Kevin D., Attygalle, Athula B., Xu, Shang-Cheng, Svatoš, Aleš, Meinwald, Jerrold, Houck, Marilyn A., Blankespoor, Curtis L., Eisner, Thomas
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 21.02.1994; Elsevier
• Subjects: Alcaloids; Analytical, structural and metabolic biochemistry; Biological and medical sciences; Chemistry; Chemistry, Organic; Fundamental and applied biological sciences. Psychology; Heterocyclic compounds, pigments; Other biological molecules; Physical Sciences; Science & Technology; (Z)-1,17-DIAMINOOCTADEC-9-ENE; COLEOPTERA; ALIPHATIC DIAMINE; Alkaloid; Coccinellidae; Molecular structure; Coleoptera; Angular nitrogen heterocycle; Arthropoda; Insecta; Polycyclic compound; Isolation; Invertebrata; NMR spectrum
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(01)86955-6

A novel heptacyclic alkaloid, for which we coin the name chilocorine, was isolated from a ladybird beetle, Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro- 9b-azaphenalene and 3,4-dimethyloctahydro- 8b-azaacenaphthylene. The proposed structure is based on mass spectrometric, ultraviolet spectroscopic, and NMR evidence. Chilocorine, a novel heptacyclic alkaloid, was isolated from a ladybird beetle, Chilocorus cacti. It has a unique structure made up of two tricyclic substructures, 2-methylperhydro-9 b-azaphenalene and 3,4-dimethyloctahydro-8 b-azaacenaphthylene.