An Unusual Series of Thiomethylated Canthin‐6‐ones from the North American Mushroom Boletus curtisii

Abstract

Keywords: Natural products / Canthin-6-ones / Indole alkaloids / Chiral sulfoxides / Quantum chemical calculations A unique set of thiomethylated canthin-6-one derivatives was isolated from Boletus curtisii. The bright yellow color of this mushroom is caused by two optically active canthin-6-one sulfoxides for which the names curtisin and 9-deoxycurtisin are proposed. The structures of the new compounds were established by MS and NMR methods and the absolute con-

Solution Phase and Nanoparticular Biosynthetically Inspired Interconnections in the Canthin‐6‐one β‐Carboline Series and Study of Phenotypic Properties on C. elegans

“…Since then, several dozen derivatives have been found in natural sources, mainly plants of the Rutaceae and Simaroubaceae families, but also from the Malvaceae, Amaranthaceae, Caryophyllaceae, and Zygophyllaceae families 3. More recently, these natural products have also been found in fungi ( Boletus curtisii Berk) 4. Centered on the canthin‐6‐one scaffold, a range of diverse functionalities are encountered in nature characterized principally by oxidation patterns exemplified by 2 , one the most highly oxygenated analogs isolated to date.…”

Fruitful Decades for Canthin-6-ones from 1952 to 2015: Biosynthesis, Chemistry, and Biological Activities

“…The canthin-6-one alkaloids, a subclass of β-carboline alkaloids with an additional D ring, have been isolated from various plants, principally those in the Rutaceae [1,2,3,4,5,6,7,8] and Simaroubaceae [9,10,11,12,13,14,15,16,17] families, but also those in the Amaranthaceae [18], Caryophyllaceae [19] and Zygophyllaceae [20] families, and more recently from fungi [21] and marine organisms [22]. Canthin-6-one ( 1 ) (Figure 1) was first isolated in 1952 by Haynes et al [23] from the Australian tree Pentaceras australis .…”

Ralfuranone Thioether Production by the Plant Pathogen Ralstonia solanacearum

“…In particular, a methyl thioether is a rare but erratically occurring feature among prokaryotic and eukaryotic secondary metabolites. Among the known examples are bacterial compounds such as lincomycin,14 urdamycin E,15 cytosaminomycin A,16 and the fungal canthinones 17. Although the lincomycin biosynthesis gene cluster has been cloned, and an S ‐adenosyl‐ L ‐methionine (SAM)‐dependent enzyme was proposed to catalyze the thioether formation, there is no experimental evidence for this reaction 14.…”