Identification and Characterization of a δ-Cadinol Synthase Potentially Involved in the Formation of Boreovibrins in Boreostereum vibrans of Basidiomycota

Abstract

Sesquiterpenoids are very common among natural products. A large number of sesquiterpene synthase genes have been cloned and functionally characterized. However, until now there is no report about the δ-cadinol synthase predominantly forming δ-cadinol (syn. torreyol) from farnesyl diphosphate. Sesquiterpenoids boreovibrins structurally similar to δ-cadinol were previously isolated from culture broths of the basidiomycete fungus Boreostereum vibrans. This led us to expect a corresponding gene coding for a δ-cadinol synthase that may be involved in the biosynthesis of boreovibrins in B. vibrans. Here we report the cloning and heterologous expression of a new sesquiterpene synthase gene from B. vibrans. The crude and purified recombinant enzymes, when incubating with farnesyl diphosphate as substrate, gave δ-cadinol as its principal product and thereby identified as a δ-cadinol synthase.Graphical AbstractA new sesquiterpene synthase gene was cloned from the basidiomycete fungus Boreostereum vibrans and heterologously expressed in E. coli. The purified recombinant enzyme gave δ-cadinol as its principal product from farnesyl diphosphate and thereby identified as a δ-cadinol synthase (BvCS). Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0096-4) contains supplementary material, which is available to authorized users.

Identification of sesquiterpene synthases from the Basidiomycota Coniophora puteana for the efficient and highly selective β-copaene and cubebol production in E. coli

“…To provide insights into the structural and functional diversity of STPSs from Basidiomycota, we carried out a comprehensive phylogenetic analysis. This analysis encompassed the STPS sequences of Antrodia cinnamomea [ 39 ], Armillaria gallica [ 40 ], Boreostereum vibrans [ 41 ], Coprinopsis cinereus [ 35 ], Fomitopsis pinicola [ 42 ], Lignosus rhinocerus [ 43 ] Stereum hirsutum [ 37 ] and Omphalotus olearius [ 42 ], which are all functionally characterized. The phylogenetic analysis suggests that Copu1-3 belong to the same STPS clade, sharing a 1,10-cyclization mechanism with other related enzymes in this group (Fig.…”

Sesquiterpene Cyclases from the Basidiomycete Cerrena unicolor

“…Different cyclisation mechanisms were found for the clades. Clades Armillaria gallica (ArmGa) [34], Boreostereum vibrans (BvCS) [35], Coprinopsis cinereus (Cop) [30], Coniophora puteana (Copu) [26], Formitopsis pinicola (Fompi) [25], Lignosus rhinoceros (GME) [36], Stereum hirsutum (Stehi) [27], Omphalotus olearius (Omp) [25] In Scheme 1, the initial cyclization steps performed by STS from the four clades are shown. The three types of initial cyclization's all include the loss of diphosphate and result in a primary carbocation intermediate.…”

“…Unrooted neighbor-joining phylogram of 37 experimental characterized STS. Included are STS protein sequences from Antrodia cinnamomea(AcTPS)[33], Armillaria gallica (ArmGa)[34], Boreostereum vibrans (BvCS)[35], Coprinopsis cinereus (Cop)[30], Coniophora puteana (Copu)[26], Formitopsis pinicola (Fompi)[25], Lignosus rhinoceros (GME)[36], Stereum hirsutum (Stehi)[27], Omphalotus olearius (Omp)[25], and Cerrena unicolor (Cun). Different cyclisation mechanisms were found for the clades.…”

Transcriptome analysis of polycyclic sesquiterpene biosynthesis in Leonurus sibiricus L.

“…Some known plant STSs only contain the 'DXXDD' motif as well [10]. Even more, these genes are the preferred STSs related to ylangene, copaene, gurjunene, selinene and cadinol which are all synthesized through germacrenyl cation intermediate from FPP [28][29][30][31]. Unigene4075_All and Unigene24876_All were presumed to be germacrene D synthase.…”