RESUMO
A new isoquinoline quinone system and its iodinated derivatives were isolated from the ascidian tunicate Ascidia virginea Müller 1776 (Phlebobranchia: Ascidiidae). Structures were elucidated by spectroscopic methods and derivatization reactions. Ascidine A (3,7-dihydro-1,8-dihydroxy-4-(4'-hydroxyphenyl)isoquinoline-3,7-dione (1), ascidine B (3,7-dihydro-1,8-dihydroxy-4-(4'-hydroxy-3'-iodophenyl)isoquinoline-3,7-dione (2), and ascidine C (3,7-dihydro-1,8-dihydroxy-4-(4'-hydroxy-3',5'-diiodophenyl)isoquinoline-3,7-dione (3) represent a novel type of tyrosine-derived alkaloids.
Assuntos
Produtos Biológicos/química , Isoquinolinas/química , Quinonas/química , Urocordados/química , Animais , Produtos Biológicos/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Isoquinolinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Quinonas/isolamento & purificação , EspectrofotometriaRESUMO
The essential oils obtained by hydrodistillation of green and ripe fruits, herb, flowers and roots of Smyrnium olusatrum (alexanders), have been analyzed by means of GC, GC-MS, and NMR spectroscopic methods. Roots, herb and flowers are characterized by a high content of oxygenated sesquiterpenoids, most of them furanosesquiterpenoids, while green and ripe fruits are dominated by monoterpene hydrocarbons with beta-phellandrene and alpha-pinene as major constituents. The furanosesquiterpenoids, comprising a high proportion of furanodiene and isofuranogermacrene, are present in all parts of the plant. In roots and herbs furanoeremophil-1-one is the second important furanosesquiterpenoid, whereas 1beta-acetoxyfurano-4(15)-eudesmene was detected as a prominent component in green and ripe fruits. Additionally a new furanoeudesmane derivative has been isolated from the fruits. With the aid of (13)C, (1)H and 2D NMR the structure has been established as furano-4(15)-eudesmen-1-one.