Unique Biosynthesis of Sesquarterpenes (C<sub>35</sub>Terpenes)

Sato, Tsutomu

doi:10.1271/bbb.130180

Cited by 27 publications

(26 citation statements)

References 38 publications

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“…YtpB catalyses the first committed step in C 35 terpenoid biosynthesis (Fig. ) (Sato et al ., ; Sato, ). The first C 35 terpenes identified in the Bacilli were isolated from spore preparations and designated as sporulenes (Bosak et al ., ; Kontnik et al ., ).…”

Section: Resultsmentioning

confidence: 96%

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Accumulation of heptaprenyl diphosphate sensitizes Bacillus subtilis to bacitracin: implications for the mechanism of resistance mediated by the BceAB transporter

Kingston

Zhao

Cook

et al. 2014

Molecular Microbiology

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Heptaprenyl diphosphate (C35-PP) is an isoprenoid intermediate in the synthesis of both menaquinone and the sesquarterpenoids. We demonstrate that inactivation of ytpB, encoding a C35-PP utilizing enzyme required for sesquarterpenoid synthesis, leads to an increased sensitivity to bacitracin, an antibiotic that binds undecaprenyl pyrophosphate (C55-PP), a key intermediate in cell wall synthesis. Genetic studies indicate that bacitracin sensitivity is due to accumulation of C35-PP, rather than the absence of sesquarterpenoids. Sensitivity is accentuated in a ytpB menA double mutant, lacking both known C35-PP consuming enzymes, and in a ytpB strain overexpressing the HepST enzyme that synthesizes C35-PP. Conversely, sensitivity in the ytpB background is suppressed by mutation of hepST or by supplementation with 1,4-dihydroxy-2-naphthoate, a co-substrate with C35-PP for MenA. Bacitracin sensitivity results from impairment of the BceAB and BcrC resistance mechanisms by C35-PP: in a bceAB bcrC double mutant disruption of ytpB no longer increases bacitracin sensitivity. These results suggest that C35-PP inhibits both BcrC (a C55-PP phosphatase) and BceAB (an ABC transporter that confers bacitracin resistance). These findings lead to a model in which BceAB protects against bacitracin by transfer of the target, C55-PP, rather than the antibiotic across the membrane.

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Section: Resultsmentioning

confidence: 96%

“…This precursor (Fig. ) has recently been designated as baciterpenol A (Sato, ). The roles of C 35 terpenoids (designated as sesquarterpenes; Sato et al ., ) are largely unexplored, although a minor role in H 2 O 2 resistance was reported (Bosak et al ., ).…”

Section: Resultsmentioning

confidence: 99%

Accumulation of heptaprenyl diphosphate sensitizes Bacillus subtilis to bacitracin: implications for the mechanism of resistance mediated by the BceAB transporter

Kingston

Zhao

Cook

et al. 2014

Molecular Microbiology

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“…The terpenoids are sorted into classes depending on the number of isoprene units: monoterpenoids (C 10 ), sesquiterpenoids (C 15 ), diterpenoids (C 20 ), triterpenoids (C 30 ), and tetraterpenoids (C 40 ), as shown in Figure 1 (Smanski et al, 2012; Sato, 2013). IDP and DMADP are condensed to the C 10 -compound geranyl diphosphate (GDP) by geranyl diphosphate synthase (GDS) in the plastid.…”

Section: The Biosynthetic Pathways Of Pharmaceutical Terpenoids In Mementioning

confidence: 99%

Plant Metabolic Engineering Strategies for the Production of Pharmaceutical Terpenoids

Tang

2016

Front. Plant Sci.

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Pharmaceutical terpenoids belong to the most diverse class of natural products. They have significant curative effects on a variety of diseases, such as cancer, cardiovascular diseases, malaria and Alzheimer’s disease. Nowadays, elicitors, including biotic and abiotic elicitors, are often used to activate the pathway of secondary metabolism and enhance the production of target terpenoids. Based on Agrobacterium-mediated genetic transformation, several plant metabolic engineering strategies hold great promise to regulate the biosynthesis of pharmaceutical terpenoids. Overexpressing terpenoids biosynthesis pathway genes in homologous and ectopic plants is an effective strategy to enhance the yield of pharmaceutical terpenoids. Another strategy is to suppress the expression of competitive metabolic pathways. In addition, global regulation which includes regulating the relative transcription factors, endogenous phytohormones and primary metabolism could also markedly increase their yield. All these strategies offer great opportunities to enhance the supply of scarce terpenoids drugs, reduce the price of expensive drugs and improve people’s standards of living.

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“…Unlike squalene for the synthesis of triterpenoids or the prenyl diphosphate precursors for that of hemi‐, mono‐, sesqui‐ or diterpenes, the C 40 tetraterpene precursor does not undergo carbocation rearrangements and remains mostly linear. Other, rarer classes of terpenes are the C 25 sesterterpenes and the C 35 sesquarterpenes which have been reviewed elsewhere and will therefore not be discussed here (Sato, ; Wang et al ., ). Finally, terpene moieties can also be coupled to moieties originating from other biosynthetic pathways, giving rise to the meroterpenoids.…”

Section: Terpenoid Biosynthesismentioning

confidence: 99%

Synthetic biology for production of natural and new‐to‐nature terpenoids in photosynthetic organisms

et al. 2016

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SUMMARYWith tens of thousands of characterized members, terpenoids constitute the largest class of natural compounds that are synthesized by all living organisms. Several terpenoids play primary roles in the maintenance of cell membrane fluidity, as pigments or as phytohormones, but most of them function as specialized metabolites that are involved in plant resistance to herbivores or plant-environment interactions. Terpenoids are an essential component of human nutrition, and many are economically important pharmaceuticals, aromatics and potential next-generation biofuels. Because of the often low abundance in their natural source, as well as the demand for novel terpenoid structures with new or improved bioactivities, terpenoid biosynthesis has become a prime target for metabolic engineering and synthetic biology projects. In this review we focus on the creation of new-to-nature or tailor-made plant-derived terpenoids in photosynthetic organisms, in particular by means of combinatorial biosynthesis and the activation of silent metabolism. We reflect on the characteristics of different potential photosynthetic host organisms and recent advances in synthetic biology and discuss their utility for the (heterologous) production of (novel) terpenoids.

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Unique Biosynthesis of Sesquarterpenes (C₃₅Terpenes)

Cited by 27 publications

References 38 publications

Accumulation of heptaprenyl diphosphate sensitizes Bacillus subtilis to bacitracin: implications for the mechanism of resistance mediated by the BceAB transporter

Accumulation of heptaprenyl diphosphate sensitizes Bacillus subtilis to bacitracin: implications for the mechanism of resistance mediated by the BceAB transporter

Plant Metabolic Engineering Strategies for the Production of Pharmaceutical Terpenoids

Synthetic biology for production of natural and new‐to‐nature terpenoids in photosynthetic organisms

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Unique Biosynthesis of Sesquarterpenes (C35Terpenes)

Cited by 27 publications

References 38 publications

Accumulation of heptaprenyl diphosphate sensitizes Bacillus subtilis to bacitracin: implications for the mechanism of resistance mediated by the BceAB transporter

Accumulation of heptaprenyl diphosphate sensitizes Bacillus subtilis to bacitracin: implications for the mechanism of resistance mediated by the BceAB transporter

Plant Metabolic Engineering Strategies for the Production of Pharmaceutical Terpenoids

Synthetic biology for production of natural and new‐to‐nature terpenoids in photosynthetic organisms

Contact Info

Product

Resources

About

Unique Biosynthesis of Sesquarterpenes (C₃₅Terpenes)