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Hamberger, B.

Publications and source records attributed to Hamberger, B..

7 recordsLinked to original sources

Engineering carotenoid and steroidal glycoalkaloid depleted tomato fruit for heterologous production of high value terpenes

Plants produce specialized metabolites that function in plant defense and as attractants to pollinators and symbionts. One class of specialized metabolites are terpenoids that are synthesized from universal C5 building blocks via activities including terpene synthases, cytochromes P450, and glycosyl transferases. Some terpenes are highly valued for their use as insect repellants, fragrances, antimicrobial compounds, low calorie sweeteners, flavors, and medicines. Low abundance in target tissues, present in complex mixtures, as well as challenging extraction logistics are barriers to economic sustainable production of these compounds from their native species. While heterologous expression of terpenoid biosynthetic genes is feasible, the potential derivation of the products into conjugates via endogenous cytochromes P450 and glycosyl transferases limits this approach. In this project, we used multiplex gene editing technologies to overcome these challenges by creating novel tomato chassis with altered terpenoid biosynthetic capacity in fruit. Excluding central metabolic genes to minimalize impacts on growth and development, we selected 23 known and potential terpene-related genes expressed specifically in the fruit for gene editing. Fruit production and metabolic profiles of three chassis lines with alterations in the major classes of fruit specialized metabolites indicate loss of these genes is tolerated for fruit production. These combinatorial knockouts also showed modulation of native carbon reallocation toward endogenous sinks beneficial for a biosynthetic chassis. Establishing metabolite-modified fruit chassis demonstrates efficient combinatorial editing of entire branches of plant specialized metabolism, facilitating engineering of heterologous terpenes of industrial interest in tomato fruit.

plant biology↗

Entry Steps in the Biosynthetic Pathway to DiterpenoidAlkaloids in Delphinium grandiflorum and Aconitum plicatum

Both the terpenoid and alkaloid classes of specialized metabolites have received considerable attention for their wide range of practical applications, however, few examples have been identified of these classes intersecting. The diterpenoid alkaloids are one such example of nitrogen-containing terpenoids which are found throughout many independent plant lineages, but primarily within the Aconitum (Wolfs-Bane) and Delphinium (Larkspur) genera. While there is considerable interest in these compounds for their wide range of bioactivities, their structural complexity often precludes their production through chemical synthesis, and little progress has been made towards elucidation of their biosynthetic pathways. Here, we employ a comparative transcriptomics approach to identify six enzymatic steps in the biosynthesis of atisinium, conserved across both Delphinium grandiflorum and Aconitum plicatum. Key to this pathway is a reductase which selectively incorporates ethanolamine over ethylamine into the diterpenoid scaffold. While the majority of diterpenoid alkaloids contain an ethylamine moiety, we demonstrate through isotope labeling in Aconitum callus cultures and a computational metabolomics approach that ethanolamine is, unintuitively, the preferred source of nitrogen for these metabolites. Identification of these enzymes and production of a key intermediate in a heterologous host paves the way for biosynthetic production of this group of metabolites with promise for medicinal applications.

biochemistry↗

Rule-Based Deconstruction and Reconstruction of Diterpene Libraries: Categorizing Patterns & Unravelling the Structural Landscape

Terpenoids make up the largest class of specialized metabolites with over 180,000 reported compounds currently across all kingdoms of life. Their synthesis accentuates one of natures most choreographed enzymatic and non-reversible chemistries, leading to an extensive range of structural functionality and diversity. Current terpenoid repositories provide a seemingly endless landscape to systematically survey for information regarding structure, sourcing, and synthesis. Efforts here investigate entries for the 20-carbon diterpenoid variants and deconstruct the complex patterns into simple, categorical groups. This deconstruction approach reduces over 60,000 unique diterpenoid structures to less than 1,000 categorical structures. Furthermore, the majority of diterpene entries (over 75%) can be represented by less than 25 core skeletons. Natural diterpenoid abundance was mapped throughout the tree of life and structural diversity was correlated at an atom-and-bond resolution. Additionally, all identified core structures provide guidelines for predicting how diterpene diversity originates via the mechanisms catalyzed by diterpene synthases. Over 95% of diterpenoid structures rely on cyclization. Here a reconstructive approach is reapplied based on known biochemical rules to model the birth of compound diversity. Reconstruction enabled prediction of highly probable synthesis mechanisms for bioactive taxane-relatives, which were discovered over three decades ago. This computational synthesis validates previously identified reaction products and pathways, as well as enables predicting trajectories for synthesizing real and theoretical compounds. This deconstructive and reconstructive approach applied to the diterpene landscape provides modular, flexible, and an easy-to-use toolset for categorically simplifying otherwise complex or hidden patterns. Significance StatementWe take a deconstructive and reconstructive approach to explore the origins of the diterpene landscape. Introduction of a navigational toolset enables users to survey compound libraries in ways formerly uncharted. Their utility demonstrated here, maps out diterpene cyclization routes, critical intermediate waypoints, and guidance for how to arrive at compounds previously off-the-map. Information acquired from these tools may imply the diterpene landscape is vastly unexplored, with the plateau for discovery potentially still out of sight.

bioinformatics↗

A molecular representation system with a common reference frame for natural products pathway discovery and structural diversity tasks.

Researchers have uncovered hundreds of thousands of natural products, many of which contribute to medicine, materials, and agriculture. However, missing knowledge of the biosynthetic pathways to these products hinders their expanded use. Nucleotide sequencing is key in pathway elucidation efforts, and analyses of natural products molecular structures, though seldom discussed explicitly, also play an important role by suggesting hypothetical pathways for testing. Structural analyses are also important in drug discovery, where many molecular representation systems - methods of representing molecular structures in a computer-friendly format - have been developed. Unfortunately, pathway elucidation investigations seldom use these representation systems. This gap is likely because those systems are primarily built to document molecular connectivity and topology, rather than the absolute positions of bonds and atoms in a common reference frame, the latter of which enables chemical structures to be connected with potential underlying biosynthetic steps. Here, we present a unique molecular representation system built around a common reference frame. We tested this system using triterpenoid structures as a case study and explored the systems applications in biosynthesis and structural diversity tasks. The common reference frame system can identify structural regions of high or low variability on the scale of atoms and bonds and enable hierarchical clustering that is closely connected to underlying biosynthesis. Combined with phylogenetic distribution information, the system illuminates distinct sources of structural variability, such as different enzyme families operating in the same pathway. These characteristics outline the potential of common reference frame molecular representation systems to support large-scale pathway elucidation efforts. Significance StatementStudying natural products and their biosynthetic pathways aids in identifying, characterizing, and developing new therapeutics, materials, and biotechnologies. Analyzing chemical structures is key to understanding biosynthesis and such analyses enhance pathway elucidation efforts, but few molecular representation systems have been designed with biosynthesis in mind. This study developed a new molecular representation system using a common reference frame, identifying corresponding atoms and bonds across many chemical structures. This system revealed hotspots and dimensions of variation in chemical structures, distinct overall structural groups, and parallels between molecules structural features and underlying biosynthesis. More widespread use of common reference frame molecular representation systems could hasten pathway elucidation efforts.

biochemistry↗

CYP76BK1 orthologs catalyze furan and lactone ring formation in clerodane diterpenoids across the mint family

The Lamiaceae (mint family) is the largest known source of furanoclerodanes, a subset of clerodane diterpenoids with broad bioactivities including insect antifeedant properties. The Ajugoideae subfamily, in particular, accumulates significant numbers of structurally related furanoclerodanes. The biosynthetic capacity for formation of these diterpenoids is retained across most Lamiaceae subfamilies, including the early-diverging Callicarpoideae which forms a sister clade to the rest of Lamiaceae. VacCYP76BK1, a cytochrome P450 monooxygenase from Vitex agnus-castus, was previously found to catalyze the formation of the proposed precursor to furan and lactone-containing labdane diterpenoids. Through transcriptome-guided pathway exploration, we identified orthologs of VacCYP76BK1 in Ajuga reptans and Callicarpa americana. Functional characterization demonstrated that both could catalyze the oxidative cyclization of clerodane backbones to yield a furan ring. Subsequent investigation revealed a total of ten CYP76BK1 orthologs across six Lamiaceae subfamilies. Through analysis of available chromosome-scale genomes, we identified four CYP76BK1 members as syntelogs within a conserved syntenic block across divergent subfamilies. This suggests an evolutionary lineage that predates the speciation of the Lamiaceae. Functional characterization of the CYP76BK1 orthologs affirmed conservation of function, as all catalyzed furan ring formation. Additionally, some orthologs yielded two novel lactone ring moieties. The presence of the CYP76BK1 orthologs across Lamiaceae subfamilies closely overlaps with the distribution of reported furanoclerodanes. Together, the activities and distribution of the CYP76BK1 orthologs identified here support their central role in furanoclerodane biosynthesis within the Lamiaceae family. Our findings lay the groundwork for biotechnological applications to harness the economic potential of this promising class of compounds. Significance StatementThe discovery and functional characterization of CYP76BK1 orthologs across diverse Lamiaceae subfamilies revealed novel chemistry and their central role in furanoclerodane biosynthesis, providing insights into the metabolic landscape and dynamic evolution of this plant family over approximately 50 million years. These findings pave the way for targeted biosynthetic engineering efforts and the sustainable production of furanoclerodane compounds, offering promising prospects for agricultural and pharmaceutical applications.

plant biology↗

Chromosome-scale Salvia hispanica L. (Chia) genome assembly reveals rampant Salvia interspecies introgression

Salvia hispanica L. (Chia), a member of the Lamiaceae, is an economically important crop in Mesoamerica, with health benefits associated with its seed fatty acid composition. Chia varieties are distinguished based on seed color including mixed white and black (Chia pinta) and black (Chia negra). To facilitate research on Chia and expand on comparative analyses within the Lamiaceae, we generated a chromosome-scale assembly of a Chia pinta accession and performed comparative genome analyses with a previously published Chia negra genome assembly. The Chia pinta and negra genome sequences were highly similar as shown by a limited number of single nucleotide polymorphisms and extensive shared orthologous gene membership. There is an enrichment of terpene synthases in the Chia pinta genome relative to the Chia negra genome. We sequenced and analyzed the genomes of 20 Chia accessions with differing seed color and geographic origin revealing population structure within S. hispanica and interspecific introgressions of Salvia species. As the genus Salvia is polyphyletic, its evolutionary history remains unclear. Using large-scale synteny analysis within the Lamiaceae and orthologous group membership, we resolved the phylogeny of Salvia species. This study and its collective resources further our understanding of genomic diversity in this food crop and the extent of inter-species hybridizations in Salvia. PLAIN LANGUAGE SUMMARYChia pinta is an economically important crop due to the high fatty acid present in the seeds. There are multiple types of Chia based on the seeds color including mixed which and black (Chia pinta), black (Chia negra), and white (Chia blanca). We generated a genome assembly of Chia pinta and compared it to existing genome assemblies. While the assemblies are highly similar there are key differences in terpene synthase composition between Chia pinta and Chia negra. We also sequenced 20 other Chia accessions with different seed color and geographic origin to determine a population structure within Chia. We generated genomic resources to further our understanding of this food crop. ABBREVIATIONSBGC Biosynthetic gene cluster BUSCO Benchmarking Universal Single Copy Orthologs GO Gene ontology SNP Single nucleotide polymorphism TIR Terminal inverted repeat TPS Terpene synthase WGS Whole genome shotgun

genomics↗

Current production as a rapid response expression reporter under micro-oxic and anoxic conditions

Inducible gene expression is crucial for regulating cellular processes and production of compounds within cellular pathways. Yet, inducing gene expression is only the first step to utilizing cellular processes for an applied purpose such as biosensors. Detecting when gene expression occurs is central to understanding the overall mechanism of the process as well as maximizing the process. Fluorescent proteins have been established as the primary tool for detecting gene expression in inducible systems. This study proposes electricity production as an alternate tool in reporting gene expression. Using a model organism for electricity production, Shewanella oneidensis MR-1, current was shown to be an efficient reporter for gene expression and comparable to superfolder green fluorescent protein (GFP). Through regulation of the lac operator and T7 promoter, current production was induced by isopropyl {beta}-D-1-thiogalactopyranoside (IPTG) addition. IPTG addition induced translation of GFP and the MtrB protein, which complemented a {triangleup}mtrB strain of S. oneidensis MR-1 and restored current production. This inducible system generated reproducible current in 18 minutes in both micro-oxic and anoxic conditions. These results show that current is a fast reporter for gene expression.\n\nFinancial DisclosureThe team was supported by the following departments and colleges at Michigan State University: College of Natural Science, College of Engineering, Biochemistry and Molecular Biology Department and Plant Research Laboratory. The team also received support from the DOE Great Lakes Bioenergy Research Center (DOE Office of Science BER DE-FC02-07ER64494) and startup funding from the Department of Molecular Biology and Biochemistry, Michigan State University and support from Michigan State University AgBioResearch (MICL02454) (to B.H.). This work was also supported by NSF CAREER (Award #1254238) to T.A.W. MSU Alpha Chi Sigma also supported the team.\n\nCompeting InterestsThe authors declare that no competing interests exist.\n\nEthics StatementN/A\n\nData AvailabilityAll data will be supplied upon request by the corresponding author.\n\nThis work was assessed during the iGEM/PLOS Realtime Peer Review Jamboree on 23rd February 2018 and has been revised in response to the reviewers comments.

synthetic biology↗