Jul 2026· Journal of the American Chemical Society· Vol 148 31, pp.
34002-34012
· 0 citations· 59 references
Medicine
TL;DR
Brown algal terpene synthases separate into two subgroups, with mono- and diTSs containing putative chloroplast-targeting sequences while sesquiTSs lack them, suggesting convergent compartmentalization of terpene biosynthesis with land plants.
Abstract
Brown algae of the order Dictyotales uniquely stand out among stramenopiles (heterokonts) as prolific producers of bioactive terpenoid molecules associated with chemical defense and antifouling. Although more than 200 sesquiterpenoids and diterpenoids have been reported, largely from the genera of Dictyota and Dictyopteris, their biosynthetic origin has remained unknown for decades. Leveraging de novo genome and transcriptome sequencing in the nonmodel alga Dictyota coriacea, we identified a brown algal-specific lineage of type I terpene synthases (TSs) that harbors novel catalytic motifs distinct from those characterized in plants, microbes, red algae, and metazoans. Across three brown algal species, we characterized 15 terpene synthases, including DcTS-2, which produces the diterpene alcohol dilophol, a proposed biosynthetic intermediate to the antifouling metabolite pachydictyol A. X-ray crystal structures of the monoterpene synthase DcTS-3 further revealed that the brown algal enzymes retain the canonical terpene synthase fold, and together with mutagenesis studies, suggest the catalytic role of the novel motifs defining this newly established evolutionary lineage. Brown algal terpene synthases separate into two subgroups, with mono- and diTSs containing putative chloroplast-targeting sequences while sesquiTSs lack them, suggesting convergent compartmentalization of terpene biosynthesis with land plants. Together, these findings establish the molecular basis of terpenoid biosynthesis in brown algae and highlight the challenges of adapting established biosynthetic logic to nonmodel marine algae.
ABSTRACT Ancestral marine sponges produce terpenoid‐based compounds, and recent studies have begun to reveal the genetic basis in some species, including the first report of type I terpene synthases (T1TSs) in a Bubarida sponge Obruta collector. Here, we present a further genomic and functional characterization of terpenoid biosynthesis in the isonitrile terpenoid‐rich sponge Acanthella cavernosa by integrating multi‐omics with comparative genomic, phylogenetic, and biochemical analyses. We found that A. cavernosa retains the full eukaryotic ancestral mevalonate pathway for terpene precursor biosynthesis. Their single α‐domain classical T1TSs form a basal, independently evolved lineage related to plant T1TS α‐domains, while UbiA‐type TSs drive lineage‐specific structural diversification. Notably, in contrast to the clustering of T1TSs with other biosynthetic genes observed in some corals, we did not observe such clustering in the sponge we sequenced, which is consistent with the observation in O. collector. Our findings provide additional evidence for the ancestral origin of metazoan terpenoid biosynthesis and further our understanding of early metazoan adaptive evolution, and facilitate biotechnological exploitation of sponge‐derived terpenoids.
Fangyan Chen, Bao Chen, Wenhui Zhang et al.· Advancement of science· 0 citations
Despite previous doubts about the origin of terpenes in springtails, a deep bioinformatic analysis of the genomes of 26 springtails surprisingly revealed the presence of many genes coding for microbial-type terpene synthases. Five candidate enzymes from Sinella curviseta representing different branches of a phylogenetic tree were selected for investigation, four of which were active in in vitro incubations with an enzyme-dependent substrate selectivity ranging from farnesyl (FPP) to geranylfarnesyl pyrophosphate (GFPP), with formation of multiple products in all cases. The obtained enzyme products included the new macrocycle sestersinellene, the enantiomer of a sesterterpene produced by a terpene synthase from Leucosceptrum canum and the unusual diterpene sinellene ether representing a novel skeleton, reinforcing springtails as an interesting source of terpenes. Extensive isotopic labelling experiments revealed several unusual mechanistic aspects such as the formation of a series of enantiomerically pure products besides one scalemic compound (germacrene D), as well as an unexpected stereochemical course for a reprotonation step in sinellene ether biosynthesis by ScTC2. Taken together, this study lays the foundation for future research on terpene biosynthesis in Collembola, an ancient lineage of arthropods.
Min Wang, Clément Schneider, Zarley Rebholz et al.· Angewandte Chemie· 0 citations
Covering: primarily from 2011 to 2026Terpenoids are an ancient and immensely diverse class of natural products. Since their emergence more than two billion years ago alongside early biological membranes, terpenoid metabolism has undergone a vast expansion in both structure and function, which directly contributed to the ecological success of terrestrial plants. Biosynthetically derived from two isomeric five-carbon isoprenoid precursors, plant terpenoids include hemi-, mono-, sesqui-, di-, sester-, tri-, tetra-, and poly-, and mero-terpenoids, that exhibit extensive variation in chain length, structural scaffolds, and functional decoration. This large chemical space is generated via dynamic metabolic networks, in which functionally versatile enzymes - most notably scaffold-forming terpene synthases and tailoring cytochrome P450 monooxygenases - are assembled into combinatorial pathway modules to yield complex bioactive terpenoid structures. Lineage-specific expansion of the underlying gene families, driven by recurrent genome and gene duplications followed by functional divergence, have facilitated the evolution of both conserved and specialized metabolic branches and natural products. Functionally, conserved terpenoids act as phytohormones, signaling molecules, and pigments governing plant growth and development, whereas typically species-specific specialized terpenoids mediate dynamic plant-environment interactions, including pest and pathogen defenses, allelopathy, pollinator attraction, root-microbiome communication, and abiotic stress tolerance. Advances in genomics, metabolomics, and synthetic biology continue to accelerate the discovery of terpenoid structures, pathways, and functions at an ever-increasing pace. Elucidating the mechanisms that generate this diversity, and the multifaceted roles that terpenoids play in plant ecology and physiology not only deepens our understanding of the evolutionary history of terrestrial plants, but also unlocks new opportunities for biotechnological innovation, spanning terpenoid-derived therapeutics, biofuels, fragrances, polymers, agrochemicals, and many other bioproducts.
G. Wyatt, Farida Yasmin, Aubanie R. Donaldson et al.· Natural product reports (Pri...· 0 citations
A decoupled evolutionary strategy between upstream precursor supply and downstream diversification in triterpenoid biosynthesis in R. roxburghii is suggested, providing a valuable genomic resource and a prioritized set of candidate genes for future metabolic engineering and quality improvement of this functional fruit crop.
Hua-Yue Zhang, Yuezhu Wang, Ming-Jie Li et al.· Plant physiology and biochem...· 0 citations
Terpene synthases (TPS) play a vital role in the
biosynthesis of secondary metabolites involved in plant
defense, development and stress response. Piper
nigrum (black pepper), a commercially important spice
crop, produces diverse terpenoids, yet the genetic basis
of these biosynthetic pathways remains underexplored.
In this study, we identified and characterized a terpene
synthase gene (PnTPS) from P. nigrum using a
biocomputational and molecular approach. Specific
primers were designed from the PnTPS gene sequence
retrieved from the NCBI database and used for PCR
amplification in leaf and stem tissues. The amplified
product was sequenced and the resulting gene was
identified as PCARF which is likely involved in the
biosynthesis of caryophyllene, a key sesquiterpene
compound associated with stress tolerance and
antimicrobial activity.
Functional domain analysis via ScanProsite revealed
the presence of a ferredoxin type iron sulphur binding
domain, characteristic of certain terpene synthases.
This study provides the molecular evidence linking a
PnTPS-derived gene to caryophyllene biosynthesis in
P. nigrum, highlighting its potential role in plant
defense. The findings pave the way for functional
validation and genetic improvement strategies aimed at
enhancing biotic stress resistance in black pepper.
Aparna K. S., Jaysree R. C., Geethalakshmi Sundararaman· Research journal of biotechn...· 0 citations
Thujopsene, a 3/6/6 tricyclic sesquiterpene, is widely distributed in the essential oils of various plants with diverse biological activities, such as antibacterial, antifungal, and antitermite properties. Here, we identified a sesquiterpene synthase (NdSTS) from the fungus Nemania diffusa that catalyzes the formation of thujopsene and thujopsan-2β-ol, as demonstrated by both in vivo and in vitro assays. This study represents the first report of a thujopsene-type sesquiterpene synthase originating from a fungal source. In addition, NdSTS displays broad substrate promiscuity and is able to utilize GPP as a substrate to produce the acyclic monoterpene alcohol geraniol in vitro. Furthermore, protein modeling combined with site-directed mutagenesis identified seven residues that are essential for the catalytic activity of NdSTS. Overall, this work expands our understanding of the catalytic diversity of fungal terpene synthases and provides novel genetic resources for thujopsene biosynthesis.
Yuxin Zhou, Jiatong Zeng, Beilin Meng et al.· Journal of Agricultural and...· 0 citations
