Diterpenoids of macromycetes

Abstract

This review surveys the chemical and biological literature dealing with the isolation, structure elucidation and bioactivity of diterpenoids from the fruiting bodies of macromycetes, concentrating on work that has appeared in the literature up to December 2007. In addition, this paper examines the research of diterpenoids produced by macromycetes grown in mycelial culture and the culture conditions for the fermentation of macromycetes.

Biosynthesis of Terpenoid Natural Products in Fungi

“…The scarcity of diterpene synthase homologs in our genome survey seems to be supported by the relatively small number of diterpenoid compounds characterized from Basidiomycota [194] compared to the large number of sesquiterpenoid natural products isolated from these fungi. However, the assumption that diterpenoids do not play a major role in the natural products portfolio of Basidiomycota may not be correct.…”

“…2). Few labdane diterpenoids have been isolated from Basidiomycota [194], which could mean that this class of diterpenoid metabolites does not play a significant role in these fungi.…”

“…Most of the well-known medicinal mushrooms [37] have not been genome sequenced, but a large number of the known diterpenoids from Basidiomycota have been isolated from these mushrooms (e.g. Cyathus helence [bird's nest fungus], Hericium erinaceum [lion's mane fungus], Sarcodon scabrosus [bitter tooth fungus]) [194]. Furthermore, our genome searches were carried out with known fungal diterpene synthase sequences, including the full chimeric sequences of fungal monofunctional enzymes, such as PaFS.…”

Anti-inflammatory and cytotoxic cyathane diterpenoids from the medicinal fungus Cyathus africanus

“…In particular, the species belonging to the genus Cyathus (Nidulariaceae family) are recognized as prolific producers of bioactive cyathane diterpenoids with a unique [5][6][7] tricyclic ring skeleton. Cyathane diterpenoids represent a group of natural products with great diversity in both structure and bioactivity [2][3][4]. Since the first discovery of cyathin A 3 and allocyathin B 3 from the liquid culture of Cyathus helenae in 1972 [5], a number of cyathane diterpenoids have been isolated from the fruiting bodies of mushroom Sarcodon scabrous [6][7][8][9][10][11][12][13][14], Sarcodon glaucopus [15,16], and Sarcodon cyrneus [17,18], the culture of fungi C. helenae [5,[19][20][21], Cyathus africanus [22], Cyathus earlei [23], Cyathus striatius [24], Strobilurus tenacellus [25] and Hericium erinaceum [26][27][28][29][30][31][32][33].…”

Genome Mining for Fungal Secondary Metabolic Gene Clusters

“…Conspicuously absent in sequenced Basidiomycota genomes are genes that could encode diterpene synthases, although some mushroom-forming fungi (including the pleuromutilin antibiotic producing fungus Clitiopilus passeckerianus [109]) have been reported to produce diterpenoids [110]. Ascomycota on the other hand are known to be prolific producers of bioactive diterpenoids and several biosynthetic gene clusters have been characterized.…”