Terpenoids from Microliabum polymnioides

• Published in: Phytochemistry (Oxford) Vol. 65; no. 18; pp. 2557 - 2560
• Main Authors: Díaz, Oscar J., Gil, Roberto, Novara, Lázaro J., Sosa, Virginia E., de la Fuente, Juana R.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.09.2004; Elsevier
• Subjects: Asteraceae; Biochemistry & Molecular Biology; chemical structure; Chemotaxonomy; dihydrozaluzanin; guaianolides; Lactones - chemistry; Lactones - isolation & purification; Liabeae; Liabum; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Melastomataceae - chemistry; Microliabum; Microliabum polymnioides; Modified guaianolide; noreudesman; Noreudesmanolide; phytochemicals; plant extracts; Plant Sciences; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; sesquiterpenoid lactones; spectral analysis; stereochemistry; Terpenes - chemistry; Terpenes - isolation & purification; terpenoids; Microliabum; Liabeae; Liabum; Modified guaianolide; Asteraceae; Chemotaxonomy; Noreudesmanolide; noreudesmanolide; modified guaianolide; LIABUM-FLORIBUNDUM; GUAIANOLIDES; DERIVATIVES; chemotaxonomy; SESQUITERPENE LACTONES
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2004.08.009

11αH,13-dihydrozaluzanin E ( 1), and a noreudesmanolide: 1 β-hydroxy-4-oxo-11βH-4-noreudesman-6,12-olide ( 2) were isolated and characterized from Microliabum polymnioides, together with related known sesquiterpenolides and the results used for chemotaxanomical classification. The phytochemical study of M. polymnioides led to the isolation of two sesquiterpene lactones namely: 11αH-dihydrozaluzanin E and 1β-hydroxy-4-oxo-11βH-4-noreudesman-6,12-olide. Their structures were determined by spectroscopic methods. The relative stereochemistry was established by a combination of coupling constant analysis, NOESY correlations and molecular modeling. Three related known sesquiterpene lactones were also identified, and these data were used for chemotaxonomical purposes.