Configurational analysis of cubebins and bicubebin from Aristolochia lagesiana and Aristolochia pubescens

• Published in: Phytochemistry (Oxford) Vol. 67; no. 7; pp. 735 - 742
• Main Authors: de Pascoli, Inara C., Nascimento, Isabele R., Lopes, Lucia M.X.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.04.2006; Elsevier
• Subjects: 4-Butyrolactone - chemistry; 4-Butyrolactone - pharmacology; Agronomy. Soil science and plant productions; Aristolochia; Aristolochia - chemistry; Aristolochia lagesiana; Aristolochia pubescens; Aristolochiaceae; Bicubebin; Biochemistry & Molecular Biology; Biological and medical sciences; Butyrolactol; chemical constituents of plants; Chemical constitution; chemical structure; Circular Dichroism; Cubebin; dibenzylbutyrolactone lignan; Fundamental and applied biological sciences. Psychology; Generalities. Genetics. Plant material; Genetic resources, diversity; Genetics and breeding of economic plants; Life Sciences & Biomedicine; Lignan; lignans; Lignans - chemistry; Lignans - isolation & purification; Lignans - pharmacology; Magnetic Resonance Spectroscopy; Molecular Conformation; Plant Extracts - chemistry; Plant material; Plant physiology and development; Plant Sciences; Plants, Medicinal; Science & Technology; spectral analysis; stereochemistry; Brazil; Butyrolactol; Lignan; Aristolochiaceae; Aristolochia pubescens; Aristolochia lagesiana; Cubebin; Bicubebin; (+)-BURSERAN; CONJUGATE-ADDITION; WOOD; butyrolactol; DIBENZYLBUTYROLACTONE; lignan; cubebin; (-)-CUBEBIN; CHEMISTRY; bicubebin; LIGNANS; CONSTITUENTS; Molecular structure; Isolation; Low temperature
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2006.01.019

(8 S,8′ R,9 S)-, (8 R,8′ R,9 R)-, and (8 R,8′ R,9 S)-cubebins, together with (8 R,8′ R,8″ R,8‴ R,9 R,9″ S) bicubebin, were isolated from Aristolochia lagesiana and Aristolochia pubescens. Their structures were determined by spectroscopic methods, including 1H and 13C NMR spectroscopy at low temperatures, and by chemical transformations. (8 S,8′ R,9 S)-, (8 R,8′ R,9 R)-, and (8 R,8′ R,9 S)-cubebins, together with (8 R,8′ R,8″ R,8‴ R,9 R,9″ S)-bicubebin, were isolated from Aristolochia lagesiana and Aristolochia pubescens. Their structures were determined by spectroscopic methods, including 1H and 13C NMR spectroscopy at low temperatures, and by chemical transformations.