Diterpenes Specially Produced by Fungi: Structures, Biological Activities, and Biosynthesis (2010–2020)

Abstract

Fungi have traditionally been a very rewarding source of biologically active natural products, while diterpenoids from fungi, such as the cyathane-type diterpenoids from Cyathus and Hericium sp., the fusicoccane-type diterpenoids from Fusicoccum and Alternaria sp., the guanacastane-type diterpenoids from Coprinus and Cercospora sp., and the harziene-type diterpenoids from Trichoderma sp., often represent unique carbon skeletons as well as diverse biological functions. The abundances of novel skeletons, biological activities, and biosynthetic pathways present new opportunities for drug discovery, genome mining, and enzymology. In addition, diterpenoids peculiar to fungi also reveal the possibility of differing biological evolution, although they have similar biosynthetic pathways. In this review, we provide an overview about the structures, biological activities, evolution, organic synthesis, and biosynthesis of diterpenoids that have been specially produced by fungi from 2010 to 2020. We hope this review provides timely illumination and beneficial guidance for future research works of scholars who are interested in this area.

An acetonic extract and secondary metabolites from the endolichenic fungus Nemania sp. EL006872 exhibit immune checkpoint inhibitory activity in lung cancer cell

“…Here, the effects of an ELF extract and isolated secondary metabolites on immune checkpoints in non-small lung cancer cells were investigated. This study identified (Figure 7 Radianspenes C and D, and dahliane D, are secondary metabolites (diterpenoids) found in fungi (Zhang and Feng, 2022). A previous study showed that radianspene C from Coprinus radians showed cytotoxic effect on MDA-MB-435 human breast cancer cells with an IC 50 value of 0.91 μM (Ou et al, 2012).…”

“…Radianspenes C and D, and dahliane D, are secondary metabolites (diterpenoids) found in fungi ( Zhang and Feng, 2022 ). A previous study showed that radianspene C from Coprinus radians showed cytotoxic effect on MDA-MB-435 human breast cancer cells with an IC 50 value of 0.91 μM ( Ou et al, 2012 ).…”

“…Endolichenic fungi secondary metabolites can be classified into the different chemical groups, steroids, terpenoids, xanthones, quinones, peptides, sulphur-containing chromenones, etc ( Yang et al, 2018b ; Padhi et al, 2019b ). More than 40,000 terpenoid compounds have been isolated from natural sources and, especially, diterpenoids can be found in all areas of life, and are secondary metabolites of fungi and plants ( Zhang and Feng, 2022 ). Due to their structural diversity and bioactivity, diterpenoids may be potential alternative therapies.…”

Natural Sesquiterpenoids, Diterpenoids, Sesterterpenoids, and Triterpenoids with Intriguing Structures from 2017 to 2022

“…Structurally, they have mainly cyclic carbon skeleton especially tri‐ and tetracyclic ring systems. [ 79 ] The main carbon skeletons and their transformation between each other have been shown in Figure 12. Importantly, compounds of this family show diverse biological activities, including anti‐tumor, anti‐renal fibrosis, antimicrobial, and neurotrophic effects.…”

Biochemical and Genetic Basis of Guanacastane Diterpene Biosynthesis in Basidiomycete Fungi

“…Diterpenoids, derived from the universal precursor geranylgeranyl diphosphate (GGPP), are a diverse class of structurally complex and biologically important natural products mainly produced by plants, fungi, bacteria, and marine invertebrates. − Their structural complexity and diversity are mainly generated by diterpene synthases (DTSs), which can synthesize cyclic molecules with multiple stereogenic centers from the acyclic precursor GGPP in a single reaction. − Thus, numerous DTSs have been identified and characterized to understand the basis for the production of such diverse molecular architectures. The main classes of DTSs were described as class I and II terpene synthases, depending on the reaction mechanisms and amino acid sequences.…”