Pteridanoside, the first protoilludane sesquiterpene glucoside as a toxic component of the neotropical bracken fern Pteridium aquilinum var. caudatum

✍ Scribed by Uvidelio Francisco Castillo; Youji Sakagami; Miguel Alonso-Amelot; Makoto Ojika

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 361 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00728-0

✦ Synopsis

Chromatographic fractionation, monitored by brine shrimp bioassay, led to the isolation of the first protoilludane-type sesquiterpene glucoside, pteridanoside (5), from a bioactive hot-water extract of the neotropical bracken fern Pteridium aquilinum var. caudatum (Dennstaedtiaceae). The enzymatic hydrolysis of 5 yielded its aglycon, pteridanone ( ), and D-glucose. The absolute stereostructure of 5 was confirmed by the CD spectroscopic analysis of 6. Pteridanoside (5) exhibited toxicity (LC50 of 250 gg/ml at 24 h and 62.5 lag/ml at 48 h) toward brine shrimp, while the aglycon 6 did not.