Terpene synthases are widely distributed in bacteria

Abstract

Odoriferous terpene metabolites of bacterial origin have been known for many years. In genome-sequenced Streptomycetaceae microorganisms, the vast majority produces the degraded sesquiterpene alcohol geosmin. Two minor groups of bacteria do not produce geosmin, with one of these groups instead producing other sesquiterpene alcohols, whereas members of the remaining group do not produce any detectable terpenoid metabolites. Because bacterial terpene synthases typically show no significant overall sequence similarity to any other known fungal or plant terpene synthases and usually exhibit relatively low levels of mutual sequence similarity with other bacterial synthases, simple correlation of protein sequence data with the structure of the cyclized terpene product has been precluded. We have previously described a powerful search method based on the use of hidden Markov models (HMMs) and protein families database (Pfam) search that has allowed the discovery of monoterpene synthases of bacterial origin. Using an enhanced set of HMM parameters generated using a training set of 140 previously identified bacterial terpene synthase sequences, a Pfam search of 8,759,463 predicted bacterial proteins from public databases and in-house draft genome data has now revealed 262 presumptive terpene synthases. The biochemical function of a considerable number of these presumptive terpene synthase genes could be determined by expression in a specially engineered heterologous Streptomyces host and spectroscopic identification of the resulting terpene products. In addition to a wide variety of terpenes that had been previously reported from fungal or plant sources, we have isolated and determined the complete structures of 13 previously unidentified cyclic sesquiterpenes and diterpenes.terpene synthase | bacteria | heterologous expression

Crystallization and X-ray diffraction analysis of a putative bacterial class I labdane-related diterpene synthase

“…However, compared with the presence and production of other terpenoids with a different number of isoprene (C 5 ) units, from which they are biosynthetically derived, bacterial diterpenoids (C 20 ) are relatively uncommon (Yamada et al, 2015). As a consequence of their structural and stereochemical diversity, diterpenoids exhibit a broad range of biological activities, including antibiotic, fungicidal, antiinflammatory and tumorstatic activities, amongst others (Rasoamiaranjanahary et al, 2003;Toyomasu et al, 2007;De Boer & Leeuwen, 2012;Janke et al, 2014).…”

“…(NCBI accession No. WP_019525557.1) and contains the typical DDXXXE motif and the NSE triad ND(L/I/V)-XSXXXE ( Table 1) that have been found in class I terpene synthases (Christianson, 2006;Yamada et al, 2015). Both motifs together bind the trinuclear Mg 2+ cluster, which triggers the departure of the substrate pyrophosphate leaving group to generate inorganic pyrophosphate (PP i ) and a highly reactive allylic carbocation that can undergo rapid isomerization and cyclization (Christianson, 2006).…”

Volatile communication between fungi and bacteria

“…3C; CPter91_2617 and CPter291_2730). Terpene cyclases are widely distributed in bacteria, but mostly characterised in Streptomyces species (Cane & Ikeda, 2012, Yamada et al, 2015. To date only one terpene cyclase from Proteobacteria has been functionally characterised, the 2-methylenebornane synthase from Pseudomonas fluorescens Pf0-1 (Chou et al 2011).…”

“…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. Thus we can conclude that many soil microbes harbor genes encoding such terpene synthases.…”

The ecological role of volatile mediated interactions belowground

“…However, recent studies revealed that terpenes can be produced by all kingdoms of life including prokaryotes (Takamatsu et al 2011;Yamada et al 2012;Yamada et al 2015;Song et al 2015b;Chen et al 2016). Recently, Yamada et al (2015) described a powerful bioinformatics method based on the use of Hidden Markov Models (HMMs) and Protein Families Database (PFAM) search that has allowed the discovery of terpene synthases of bacterial origin and showed that phylogenetically different bacteria can be a rich source of terpenes. Both the number, the wide distribution, and the structural diversity of terpenes provide enormous potential for mediating significant chemical interactions and communication belowground.…”