Terpenes from Marine-Derived Fungi

Abstract

Terpenes from marine-derived fungi show a pronounced degree of structural diversity, and due to their interesting biological and pharmacological properties many of them have aroused interest from synthetic chemists and the pharmaceutical industry alike. The aim of this paper is to give an overview of the structural diversity of terpenes from marine-derived fungi, highlighting individual examples of chemical structures and placing them in a context of other terpenes of fungal origin. Wherever possible, information regarding the biological activity is presented.

Terretonin, ophiobolin, and drimaneterpenes with absolute configurations from an algicolous Aspergillus ustus

“…The total EtOAc-soluble fraction (35.5 g) was subjected to stepgradient silica gel column chromatography (CC) with a solvent system consisting of 0-100% petroleum ether (PE)-EtOAc to afford 14 fractions (Frs. [1][2][3][4][5][6][7][8][9][10][11][12][13][14] on the basis of TLC analysis. Fr.…”

“…They exhibit various bioactivities, including antibacterial, antifungal, antiinsectan, cytotoxicity, etc., but not much is known about their true biological and ecological functions. 1,2 Aspergillus ustus (A. insuetus) has been proven to be a prolific producer of terpenes, containing sesquiterpenes, sesterterpenes, and meroterpenes. [3][4][5][6][7] However, most of them have been assigned only relative configurations, and their absolute configurations remain unresolved.…”

Secondary Metabolites

“…Cyclization reactions of geranylgeranyl diphosphate led to many structural types of diterpenoids, presenting a large range of polarity nature, from apolar hydrocarbons such as cembrene (Villanueva and Setzer, 2010), a 14-membered ring, to fully oxidized skeleton of virescenoside ( Figure 5), isolated from marine fungus Acremonium striatisporum (Ebel, 2010). Sesterterpenes (C 25 ) may be the least common group of terpenoids.…”

Volatile communication between fungi and bacteria

“…Recent research demonstrated that microorganisms, including fungi and bacteria, are a rich source of terpenes too . In the past two decades several terpene cyclases and their related products have been characterised for several soil-derived fungi (Collado et al, 2007, Ebel, 2010, Singh et al, 2011, Dickschat, 2017. Yamada et al (2015) showed that terpenes and their cyclases are also widespread in bacteria.…”

“…Even though terpenes are generally considered to be plant metabolites, recent research shows that microorganisms are a rich source of terpenes too (Dickschat et al, 2014). An increasing number of terpenes have been reported for fungi, most of them being sesquiterpenes (Collado et al, 2007, Ebel, 2010, Dickschat, 2017. Even more recently, the growing knowledge on bacterial genomes resulted in the discovery of terpenes and their synthases in bacteria, indicating that the genetic capacity of bacteria to make terpenes is widespread (Cane & Ikeda, 2012, Song et al, 2015.…”