Phlegmacaritones A and B, a Pair of Serratane-Related Triterpenoid Epimers with an Unprecedented Carbon Skeleton from Phlegmariurus carinatus

A pair of novel serratane-related triterpenoid epimers, phlegmacaritones A (1) and B (2), possessing an unprecedented 15,30-lactone-14,15-seco skeleton, six new serratane-type triterpenoids, phlegmanols G-L (3-5 and 14-16), and 16 known compounds were isolated from the whole plant of Phlegmariurus carinatus. The structures of the new metabolites were established on the basis of comprehensive spectroscopic data analysis and electronic circular dichroism calculations. A possible biosynthetic pathway for phlegmacaritones A (1) and B (2) was proposed. All compounds were submitted to cytological profiling on a cell line derived from a patient with Parkinson's disease. Phlegmacaritone B (2) induced a distinct phenotypic profile with alterations in α-tubulin, mitochondria, and autophagosomal and early endosomal features.