Talaronoids A–D: four fusicoccane diterpenoids with an unprecedented tricyclic 5/8/6 ring system from the fungus Talaromyces stipitatus

Abstract

Talaronoids A−D (1−4), four diterpenoids with an unexpected tricyclic 5/8/6 carbon skeleton, were isolated from Talaromyces stipitatus, representing a new class of fusicoccane diterpenoids and the first examples of natural...

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

“…Fusicoccane diterpenoids, characterized by 5/8/5, 5/8/6, 5/9/4, and 5/9/5 fused carbocyclic ring systems, include the fusicoccins, cotylenins, brassicicenes, heterodimers, and homodimers [ 77 , 78 , 79 , 80 ]. They were first isolated as glycosides from the phytopathogenic fungus Fusicoccum amygdali , in 1964 [ 81 ].…”

“…Talaronoids A–D 22 – 25 , four diterpenoids with an unexpected tricyclic 5/8/6 carbon skeleton isolated from Talaromyces stipitatus , represent a new class of fusicoccane diterpenoids with a benzo[ a ]cyclopenta[ d ]cyclooctane skeleton [ 80 ]. Plausible biosynthetic pathways of talaronoids A–D 22 – 25 have been proposed starting from geranylgeranyl diphosphate with a Wagner–Meerwein rearrangement as the key step ( Scheme 3 ).…”

Biochemical Characterization of a Fungal Bifunctional Type I Diterpene Synthase Brings a Cryptic Natural Product to Light

“…Recently, a group of diterpenoids, talaronoid A 9 , B 10 , and C 11 , containing a 5-8-6 fused ring system were isolated from Talaromyces stipitatus (Figure 3). 26 Using the amino acid sequence of TndC, we identified a gene cluster in T. stipitatus harboring an assortment of genes similar to those in the tnd biosynthetic cluster (Figures S3-S5). However, when we scanned crude extracts of A. flavipes CNL-338 for the presence of 9, 10 , and 11 , the compounds were not detected.…”

Hypoestins A–D: highly modified fusicoccane diterpenoids with promising Cav3.1 calcium channel inhibitory activity from Hypoestes purpurea

“…7,8 In recent years, some rearranged fusicoccane diterpenoids with 5/9/5, 5/9/4, or 5/8/6-fused carbocyclic skeletons were also reported from fungi. [9][10][11] These compounds have been reported to exhibit remarkable anti-inflammatory, antitumor, and butyrylcholinesterase inhibitory activities. [10][11][12][13] Due to their fascinating architectures and surprising biological activities, fusicoccane diterpenoids have attracted much interest from the communities of natural product chemistry, chemical synthesis, biosynthesis, and pharmacology.…”

“…[9][10][11] These compounds have been reported to exhibit remarkable anti-inflammatory, antitumor, and butyrylcholinesterase inhibitory activities. [10][11][12][13] Due to their fascinating architectures and surprising biological activities, fusicoccane diterpenoids have attracted much interest from the communities of natural product chemistry, chemical synthesis, biosynthesis, and pharmacology. 12,[14][15][16][17] The genus Hypoestes (Acanthaceae), shrubs or herbs, contains approximately 40 species that are distributed in the tropics of the eastern hemisphere, especially in Madagascar.…”