Nor-guanacastepene pigments from the Chilean mushroom Cortinarius pyromyxa. (September 2019)

• Record Type: Journal Article
• Authors: Lam, Yen T.H.; Palfner, Götz; Lima, Celia; Porzel, Andrea; Brandt, Wolfgang; Frolov, Andrej; Sultani, Haider; Franke, Katrin; Wagner, Christoph; Merzweiler, Kurt; Wessjohann, Ludger A.; Arnold, Norbert
• Is Part Of: Phytochemistry. Volume 165(2019)
• Publication Date: 2019-09
• Subjects: Cortinarius pyromyxa M. M. Moser & E. Horak -- Cortinariaceae -- Fungal fruiting bodies -- Diterpenoids -- Phylogeny -- Nor-guanacastepenes -- Pyromyxones; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2019.05.021
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: For the first time, the pigment composition of basidiocarps from the Chilean mushroom Cortinarius pyromyxa was studied under various aspects like phylogeny, chemistry and antibiotic activity. A molecular biological study supports the monotypic position of C. pyromyxa in subgenus Myxacium, genus Cortinarius . Four undescribed diterpenoids, named pyromyxones A-D, were isolated from fruiting bodies of C. pyromyxa . Their chemical structures were elucidated based on comprehensive one- and two-dimensional NMR spectroscopic analysis, ESI-HRMS measurements, as well as X-ray crystallography. In addition, the absolute configurations of pyromyxones A-D were established with the aid of JH, H, NOESY spectra and quantum chemical CD calculation. The pyromyxones A-D possess the undescribed nor -guanacastane skeleton. Tested pyromyxones A, B, and D exhibit only weak activity against gram-positive Bacillus subtilis and gram-negative Aliivibrio fischeri as well as the phytopathogenic fungi Botrytis cinerea, Septoria tritici and Phytophthora infestans. Graphical abstract: Image 1 Highlights: Four undescribed diterpenoids were isolated from Cortinarius pyromyxa . The isolated diterpenoids possess the undescribed nor -guanacastane skeleton. Pyromyxones A, B, and D exhibit weak antibacterial and antifungal activity. Chemical and morphological studies support the monotypic position of C. pyromyxa .