Flavonoids from two Lonchocarpus species of the Yucatan Peninsula

• Published in: Phytochemistry (Oxford) Vol. 60; no. 5; pp. 533 - 540
• Main Authors: Borges-Argáez, Rocı́o, Peña-Rodrı́guez, Luis M., Waterman, Peter G.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.07.2002; Elsevier
• Subjects: 4-diol; Biochemistry & Molecular Biology; Biological and medical sciences; Chalcone; Chemical constitution; Fabaceae - chemistry; Fabaceae - classification; Flavan-3; Flavones; Flavonoids; Flavonoids - analysis; Flavonoids - chemistry; Fundamental and applied biological sciences. Psychology; Leguminosae-Papilionoideae; Life Sciences & Biomedicine; Lonchocarpus xuul; Lonchocarpus yucatanensis; Magnetic Resonance Spectroscopy; Mexico; Molecular Structure; Plant physiology and development; Plant Sciences; Plant Structures - chemistry; Science & Technology; Mexico; Flavonoids; Flavones; Lonchocarpus xuul; Lonchocarpus yucatanensis; Flavan-3; Leguminosae-Papilionoideae; Chalcone; chalcone; flavones; leguminosae-papilionoideae; flavonoids; flavan-3,4-diol; STEM; Root; Molecular structure; Bark; Plant leaf; Flavonoid; Leguminosae; Dicotyledones; Angiospermae; Flavone derivatives; Isolation; Spermatophyta
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(02)00131-0

Leaves, stem bark and root of Lonchocarpus xuul and Lonchocarpus yucatanensis were studied separately. A chalcone, 2′,4-dimethoxy-6′-hydroxylonchocarpin ( 1 ), and the flavones 5,4′-dihydroxy-3′-methoxy-(6:7)-2,2-dimethylpyranoflavone ( 2) and 5,4′-dimethoxy-(6:7)-2,2-dimethylpyrano-flavone ( 3), together with the known carpachromene ( 4), were isolated from the leaves of both species. Similarly, the previously reported flavans xuulanin ( 5) and 3β-methoxyxuulanin ( 6), together with the novel 3β,4β,5-trimethoxy-4′-hydroxy-(6:7)-2,2-dimethylpyranoflavan ( 7), 3-hydroxy-4,5-dimethoxy-(6:7)-2,2-dimethyl-pyranoflavan ( 8), and 3,4-dihydroxy-5-methoxy-(6:7)-2,2-dimethylpyranoflavan ( 10), were isolated from the stem bark and root of both species. Finally, the known 2′,4′-dihydroxy-3′-(3-methylbut-2-enyl) chalcone ( 13) was obtained from the root of L. xuul only. The structures of the various metabolites were established by interpretation of their spectroscopic data. Leaves, stem and root bark of Lonchocarpus xuul and L. yucatanensis (Leguminosae) have yielded two flavones and three 3,4- cis-oxygenated flavons, typified by 7. All these compounds have an additional (6:7) pyran ring system.