Novel cassane and cleistanthane diterpenes from Myrospermum frutescens: absolute stereochemistry of the cassane diterpene series.
Four new diterpenes (1-4) were isolated from the leaves of Myrospermum frutescens as minor constituents. Chagresnol (1), 6beta,18-diacetoxycassan-13,15-diene (2), and chagreslactone (3) possess cassane skeletons, while chagresnone (4) exhibits a cleistanthane skeleton. Molecular structures and their relative stereochemistries were elucidated using NMR spectroscopy in combination with UV, IR, and MS spectral data. Although compound 2 was previously reported as a synthetic product, we report its first isolation as a natural product. Derivative products (10-13) were obtained to test their activities against Chagas's disease. In addition, the absolute stereochemistry of the previously isolated cassane diterpene 5 from M. frutescens is presented.
Torres-Mendoza
Daniel
D
Laboratory of Tropical Bioorganic Chemistry, Faculty of Natural, Exact Sciences and Technology, Apartado 0824-10835, University of Panama, Panama City, Republic of Panama.
Ureña González
Luis David
LD
Ortega-Barría
Eduardo
E
Coley
Phyllis D
PD
Kursar
Thomas A
TA
Capson
Todd L
TL
McPhail
Kerry
K
Cubilla-Rios
Luis
L
D000818:Animals; D014355:Chagas Disease / Q000188:drug therapy*; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007887:Fabaceae / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D004224:Diterpenes; D014344:Trypanocidal Agents