Conformational Behavior and Absolute Stereostructure of Two Phytotoxic Nonenolides from the Fungus Phoma herbarum

✍ Scribed by José Fausto Rivero-Cruz; Genoveva Garcı́a-Aguirre; Carlos M. Cerda-Garcı́a-Rojas; Rachel Mata

• Book ID: 104202815
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 147 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00469-5

✦ Synopsis

AbstractÐBioactivity-directed fractionation of extracts from the fungus Phoma herbarum led to the isolation of two new phytotoxic nonenolides: (7S,8S,9R)-7,8-dihydroxy-9-propyl-5-nonen-9-olide ( 1) and (2R,7S,8S,9R)-2,7,8-trihydroxy-9-propyl-5-nonen-9-olide (2), which were named herbarumins I and II, respectively. The stereostructures were elucidated by spectroscopic methods and a combination of molecular modeling, NOESY and 1 H± 1 H coupling constant data, which revealed that in CDCl 3 solution, 1 exists in one preferred conformation, while 2 exhibits a conformational equilibrium. Compounds 1 and 2 caused signi®cant inhibition of radicle growth of seedlings of Amaranthus hypochondriacus.