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Journal articles on the topic 'Terpene biosynthesis'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Sayari, Mohammad, Magrieta A. van der Nest, Emma T. Steenkamp, Saleh Rahimlou, Almuth Hammerbacher, and Brenda D. Wingfield. "Characterization of the Ergosterol Biosynthesis Pathway in Ceratocystidaceae." Journal of Fungi 7, no. 3 (2021): 237. http://dx.doi.org/10.3390/jof7030237.

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Terpenes represent the biggest group of natural compounds on earth. This large class of organic hydrocarbons is distributed among all cellular organisms, including fungi. The different classes of terpenes produced by fungi are mono, sesqui, di- and triterpenes, although triterpene ergosterol is the main sterol identified in cell membranes of these organisms. The availability of genomic data from members in the Ceratocystidaceae enabled the detection and characterization of the genes encoding the enzymes in the mevalonate and ergosterol biosynthetic pathways. Using a bioinformatics approach, fu

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Chekan, Jonathan R., Shaun M. K. McKinnie, Joseph P. Noel, and Bradley S. Moore. "Algal neurotoxin biosynthesis repurposes the terpene cyclase structural fold into anN-prenyltransferase." Proceedings of the National Academy of Sciences 117, no. 23 (2020): 12799–805. http://dx.doi.org/10.1073/pnas.2001325117.

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Prenylation is a common biological reaction in all domains of life wherein prenyl diphosphate donors transfer prenyl groups onto small molecules as well as large proteins. The enzymes that catalyze these reactions are structurally distinct from ubiquitous terpene cyclases that, instead, assemble terpenes via intramolecular rearrangements of a single substrate. Herein, we report the structure and molecular details of a new family of prenyltransferases from marine algae that repurposes the terpene cyclase structural fold for theN-prenylation of glutamic acid during the biosynthesis of the potent

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Helfrich, Eric J. N., Geng-Min Lin, Christopher A. Voigt, and Jon Clardy. "Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering." Beilstein Journal of Organic Chemistry 15 (November 29, 2019): 2889–906. http://dx.doi.org/10.3762/bjoc.15.283.

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Terpenoids are the largest and structurally most diverse class of natural products. They possess potent and specific biological activity in multiple assays and against diseases, including cancer and malaria as notable examples. Although the number of characterized terpenoid molecules is huge, our knowledge of how they are biosynthesized is limited, particularly when compared to the well-studied thiotemplate assembly lines. Bacteria have only recently been recognized as having the genetic potential to biosynthesize a large number of complex terpenoids, but our current ability to associate genet

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Kemper, Katarina, Max Hirte, Markus Reinbold, Monika Fuchs, and Thomas Brück. "Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems." Beilstein Journal of Organic Chemistry 13 (May 8, 2017): 845–54. http://dx.doi.org/10.3762/bjoc.13.85.

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With over 50.000 identified compounds terpenes are the largest and most structurally diverse group of natural products. They are ubiquitous in bacteria, plants, animals and fungi, conducting several biological functions such as cell wall components or defense mechanisms. Industrial applications entail among others pharmaceuticals, food additives, vitamins, fragrances, fuels and fuel additives. Central building blocks of all terpenes are the isoprenoid compounds isopentenyl diphosphate and dimethylallyl diphosphate. Bacteria like Escherichia coli harbor a native metabolic pathway for these isop

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Wang, Xin, Wei Liu, Changpeng Xin, et al. "Enhanced limonene production in cyanobacteria reveals photosynthesis limitations." Proceedings of the National Academy of Sciences 113, no. 50 (2016): 14225–30. http://dx.doi.org/10.1073/pnas.1613340113.

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Terpenes are the major secondary metabolites produced by plants, and have diverse industrial applications as pharmaceuticals, fragrance, solvents, and biofuels. Cyanobacteria are equipped with efficient carbon fixation mechanism, and are ideal cell factories to produce various fuel and chemical products. Past efforts to produce terpenes in photosynthetic organisms have gained only limited success. Here we engineered the cyanobacterium Synechococcus elongatus PCC 7942 to efficiently produce limonene through modeling guided study. Computational modeling of limonene flux in response to photosynth

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Agliassa, Chiara, and Massimo Maffei. "Origanum vulgare Terpenoids Induce Oxidative Stress and Reduce the Feeding Activity of Spodoptera littoralis." International Journal of Molecular Sciences 19, no. 9 (2018): 2805. http://dx.doi.org/10.3390/ijms19092805.

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Terpenoids are toxic compounds produced by plants as a defense strategy against insect herbivores. We tested the effect of Origanum vulgare terpenoids on the generalist herbivore Spodoptera littoralis and the response of the plant to herbivory. Terpenoids were analyzed by GC-FID and GC-MS and quantitative gene expression (qPCR) was evaluated on selected plant genes involved in both terpene biosynthesis. The insect detoxification response to terpenes was evaluated by monitoring antioxidant enzymes activity and expression of insect genes involved in terpene detoxification. O. vulgare terpenoid b

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He, Xueying, Huan Wang, Jinfen Yang, Ke Deng, and Teng Wang. "RNA sequencing on Amomum villosum Lour. induced by MeJA identifies the genes of WRKY and terpene synthases involved in terpene biosynthesis." Genome 61, no. 2 (2018): 91–102. http://dx.doi.org/10.1139/gen-2017-0142.

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Amomum villosum Lour. is an important Chinese medicinal plant that has diverse medicinal functions, and mainly contains volatile terpenes. This study aims to explore the WRKY transcription factors (TFs) and terpene synthase (TPS) unigenes that might be involved in terpene biosynthesis in A. villosum, and thus providing some new information on the regulation of terpenes in plants. RNA sequencing of A. villosum induced by methyl jasmonate (MeJA) revealed that the WRKY family was the second largest TF family in the transcriptome. Thirty-six complete WRKY domain sequences were expressed in respons

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Oldfield, Eric, and Fu-Yang Lin. "Terpene Biosynthesis: Modularity Rules." Angewandte Chemie International Edition 51, no. 5 (2011): 1124–37. http://dx.doi.org/10.1002/anie.201103110.

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9

Lancaster, Jason, Ashot Khrimian, Sharon Young, et al. "De novo formation of an aggregation pheromone precursor by an isoprenyl diphosphate synthase-related terpene synthase in the harlequin bug." Proceedings of the National Academy of Sciences 115, no. 37 (2018): E8634—E8641. http://dx.doi.org/10.1073/pnas.1800008115.

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Insects use a diverse array of specialized terpene metabolites as pheromones in intraspecific interactions. In contrast to plants and microbes, which employ enzymes called terpene synthases (TPSs) to synthesize terpene metabolites, limited information from few species is available about the enzymatic mechanisms underlying terpene pheromone biosynthesis in insects. Several stink bugs (Hemiptera: Pentatomidae), among them severe agricultural pests, release 15-carbon sesquiterpenes with a bisabolene skeleton as sex or aggregation pheromones. The harlequin bug, Murgantia histrionica, a specialist

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10

Ichikawa, Yoshiyasu, Toshiki Yamasaki, Keisuke Nakanishi, Yutaro Udagawa, Seijiro Hosokawa, and Toshiya Masuda. "Bioinspired Synthesis of the Central Core of Halichonadin H: The Passerini Reaction in a Hypothetical Biosynthesis of Marine Natural Products." Synthesis 51, no. 11 (2019): 2305–10. http://dx.doi.org/10.1055/s-0037-1610867.

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A pathway is proposed for the biosynthesis of the unique homodimeric terpene, halichonadin H. The proposed biosynthetic pathway involves two key Passerini reactions of eudesmane-type terpene isocyanides. The Passerini reaction of a model terpene isocyanide and formaldehyde afforded an α-hydroxy acetamide, which was further subjected to oxidation and a second Passerini reaction. This reaction sequence furnished an α-hydroxy malonamide connected with two identical terpene units which is the identical structural motif found in halichonadin H.

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Jin, Jieyang, Shangrui Zhang, Mingyue Zhao та ін. "Scenarios of Genes-to-Terpenoids Network Led to the Identification of a Novel α/β-Farnesene/β-Ocimene Synthase in Camellia sinensis". International Journal of Molecular Sciences 21, № 2 (2020): 655. http://dx.doi.org/10.3390/ijms21020655.

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Terpenoids play vital roles in tea aroma quality and plants defense performance determination, whereas the scenarios of genes to metabolites of terpenes pathway remain uninvestigated in tea plants. Here, we report the use of an integrated approach combining metabolites, target gene transcripts and function analyses to reveal a gene-to-terpene network in tea plants. Forty-one terpenes including 26 monoterpenes, 14 sesquiterpenes and one triterpene were detected and 82 terpenes related genes were identified from five tissues of tea plants. Pearson correlation analysis resulted in genes to metabo

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Keszei, Andras, Curt L. Brubaker, and William J. Foley. "A molecular perspective on terpene variation in Australian Myrtaceae." Australian Journal of Botany 56, no. 3 (2008): 197. http://dx.doi.org/10.1071/bt07146.

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The terpenoid-dominated essential oils in Australian Myrtaceae mediate many ecological interactions and are important industrially. Of all the significant essential oil-producing families, Myrtaceae is the only one for which there is no molecular information on terpene biosynthesis. Here we summarise available knowledge on terpene biosynthesis and its relevance to the Myrtaceae to provide a foundation for ecological and genetic studies of chemical diversity. There are several steps in the terpene biosynthesis pathway that have potential for influencing the oil yield, profile and composition of

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13

Fontana, Angelo, Annabella Tramice, Adele Cutignano, Giuliana d'Ippolito, Margherita Gavagnin, and Guido Cimino. "Terpene Biosynthesis in the NudibranchDoriopsillaareolata." Journal of Organic Chemistry 68, no. 6 (2003): 2405–9. http://dx.doi.org/10.1021/jo026131v.

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14

Shin, Kyong-Oh, Myong-Yong Park, Cho-Hee Seo, et al. "Terpene Alcohols InhibitDe NovoSphingolipid Biosynthesis." Planta Medica 78, no. 05 (2012): 434–39. http://dx.doi.org/10.1055/s-0031-1298155.

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15

Oldfield, Eric, and Fu-Yang Lin. "ChemInform Abstract: Terpene Biosynthesis: Modularity Rules." ChemInform 43, no. 17 (2012): no. http://dx.doi.org/10.1002/chin.201217266.

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Peramuna, Anantha, Hansol Bae, Carmen Quiñonero López, Arvid Fromberg, Bent Petersen, and Henrik Toft Simonsen. "Connecting moss lipid droplets to patchoulol biosynthesis." PLOS ONE 15, no. 12 (2020): e0243620. http://dx.doi.org/10.1371/journal.pone.0243620.

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Plant-derived terpenoids are extensively used in perfume, food, cosmetic and pharmaceutical industries, and several attempts are being made to produce terpenes in heterologous hosts. Native hosts have evolved to accumulate large quantities of terpenes in specialized cells. However, heterologous cells lack the capacity needed to produce and store high amounts of non-native terpenes, leading to reduced growth and loss of volatile terpenes by evaporation. Here, we describe how to direct the sesquiterpene patchoulol production into cytoplasmic lipid droplets (LDs) in Physcomitrium patens (syn. Phy

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17

Sommano, Sarana Rose, Chuda Chittasupho, Warintorn Ruksiriwanich, and Pensak Jantrawut. "The Cannabis Terpenes." Molecules 25, no. 24 (2020): 5792. http://dx.doi.org/10.3390/molecules25245792.

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Terpenes are the primary constituents of essential oils and are responsible for the aroma characteristics of cannabis. Together with the cannabinoids, terpenes illustrate synergic and/or entourage effect and their interactions have only been speculated in for the last few decades. Hundreds of terpenes are identified that allude to cannabis sensory attributes, contributing largely to the consumer’s experiences and market price. They also enhance many therapeutic benefits, especially as aromatherapy. To shed light on the importance of terpenes in the cannabis industry, the purpose of this review

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18

Bansal, Ravindra, and Prasun Kumar Mukherjee. "The Terpenoid Biosynthesis Toolkit of Trichoderma." Natural Product Communications 11, no. 4 (2016): 1934578X1601100. http://dx.doi.org/10.1177/1934578x1601100401.

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The widely used biotechnologically important fungi belonging to the genus Trichoderma are rich sources of secondary metabolites. Even though the genomes of several Trichoderma spp. have been published, and data are available on the genes involved in biosynthesis of non-ribosomal peptide synthetases and polyketide synthases, no genome-wide data are available for the terpenoid biosynthesis machinery in these organisms. In the present study, we have identified the genes involved in terpene biosynthesis in the genomes of three Trichoderma spp., viz., T. virens, T. atroviride and T. reesei. While t

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Allemann, Rudolf K. "Chemical wizardry? The generation of diversity in terpenoid biosynthesis." Pure and Applied Chemistry 80, no. 8 (2008): 1791–98. http://dx.doi.org/10.1351/pac200880081791.

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Terpene synthases catalyze the conversion of linear prenyl-diphosphates to a multitude of hydrocarbon skeletons with often high regio- and stereoselectivity. These remarkable enzymes all rely on a shared fold for activity, namely, the class I terpene cyclase fold. Recent work has illuminated the catalytic strategy used by these enzymes to catalyze the arguably most complex chemical reactions found in Nature. Terpene synthases catalyze the formation of a reactive carbocation and provide a template for the cyclization reactions while at the same time providing the necessary stability of the carb

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20

Hedhili, Sabah, Vincent Courdavault, Nathalie Giglioli-Guivarc’h, and Pascal Gantet. "Regulation of the terpene moiety biosynthesis of Catharanthus roseus terpene indole alkaloids." Phytochemistry Reviews 6, no. 2-3 (2007): 341–51. http://dx.doi.org/10.1007/s11101-006-9021-5.

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21

Heddergott, C., A. M. Calvo, and J. P. Latgé. "The Volatome of Aspergillus fumigatus." Eukaryotic Cell 13, no. 8 (2014): 1014–25. http://dx.doi.org/10.1128/ec.00074-14.

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ABSTRACT Early detection of invasive aspergillosis is absolutely required for efficient therapy of this fungal infection. The identification of fungal volatiles in patient breath can be an alternative for the detection of Aspergillus fumigatus that still remains problematic. In this work, we investigated the production of volatile organic compounds (VOCs) by A. fumigatus in vitro , and we show that volatile production depends on the nutritional environment. A. fumigatus produces a multiplicity of VOCs, predominantly terpenes and related compounds. The production of sesquiterpenoid compounds wa

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Awakawa, Takayoshi. "Unique Reaction in Bacterial Terpene Indole Biosynthesis." Journal of Synthetic Organic Chemistry, Japan 76, no. 5 (2018): 410–13. http://dx.doi.org/10.5059/yukigoseikyokaishi.76.410.

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23

Wang, Guodong, Li Tian, Naveed Aziz, et al. "Terpene Biosynthesis in Glandular Trichomes of Hop." Plant Physiology 148, no. 3 (2008): 1254–66. http://dx.doi.org/10.1104/pp.108.125187.

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Chang, Jye, and James W. Hanover. "Geographic variation in the monoterpene composition of black spruce." Canadian Journal of Forest Research 21, no. 12 (1991): 1796–800. http://dx.doi.org/10.1139/x91-247.

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Monoterpene composition of the cortical oleoresin of black spruce (Piceamariana (Mill.) B.S.P.) was determined for 33 seed sources growing in a replicated plantation in southern Michigan. Four of the nine measured monoterpenes differed significantly among origins. 3-Carene and terpinolene were high, but α-pinene was low in the Manitoba and Saskatchewan seed sources. A cluster analysis of the data separated the populations into western and eastern groups. Black spruce is more similar to red spruce (Picearubens Sarg.) than to white spruce (Piceaglauca (Moench) Voss) in terpene composition. Signi

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Chen, Zequn, Xiwu Qi, Xu Yu, et al. "Genome-Wide Analysis of Terpene Synthase Gene Family in Mentha longifolia and Catalytic Activity Analysis of a Single Terpene Synthase." Genes 12, no. 4 (2021): 518. http://dx.doi.org/10.3390/genes12040518.

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Terpenoids are a wide variety of natural products and terpene synthase (TPS) plays a key role in the biosynthesis of terpenoids. Mentha plants are rich in essential oils, whose main components are terpenoids, and their biosynthetic pathways have been basically elucidated. However, there is a lack of systematic identification and study of TPS in Mentha plants. In this work, we genome-widely identified and analyzed the TPS gene family in Mentha longifolia, a model plant for functional genomic research in the genus Mentha. A total of 63 TPS genes were identified in the M. longifolia genome sequen

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Fowler, Daniel J., John TG Hamilton, Andrew J. Humphrey, and David O'Hagan. "Plant terpene biosynthesis. The biosynthesis of linalyl acetate in Mentha citrata." Tetrahedron Letters 40, no. 19 (1999): 3803–6. http://dx.doi.org/10.1016/s0040-4039(99)00532-8.

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Zhu, Jianhua, Pu Wang, Minghua Qian, Chuxin Liang, Jiachen Zi, and Rongmin Yu. "Effect of Levopimaradiene on Terpene Trilactones Biosynthesis and Gene Expression Profiling in Ginkgo biloba Cells." Natural Product Communications 12, no. 7 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200701.

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Ginkgolides (GKs) and Bilobalide (BB) are rare terpene trilactones obtained from Ginkgo biloba, but their biosynthetic pathway is still unclear. In this paper, effects of levopimaradiene (LP) on increasing the production of terpene trilactones of G. biloba dedifferentiated cells (DDCs) and cambial meristematic cells (CMCs) were reported. The productions of ginkgolide A (GA) and ginkgolide B (GB) were 1.61 and 1.32 folds larger than that of the control groups when G. biloba DDCs was treated with LP, and the productions of ginkgolide C (GC) and BB reached 234 and 161 μg L−1 after treated with LP

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Chen, Lijia, Hui Tong, Mingxuan Wang, et al. "Effect of Enzyme Inhibitors on Terpene Trilactones Biosynthesis and Gene Expression Profiling in Ginkgo biloba Cultured Cells." Natural Product Communications 10, no. 12 (2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001205.

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The biosynthetic pathway of terpene trilactones of Ginkgo biloba is unclear. In this present study, suspension cultured cells of G. biloba were used to explore the regulation of the mevalonic acid (MVA) and methylerythritol 4-phosphate (MEP) pathways in response to specific enzyme inhibitors (lovastatin and clomazone). The results showed that the biosynthesis of bilobalide was more highly correlated with the MVA pathway, and the biosynthesis of ginkgolides was more highly correlated with the MEP pathway. Meanwhile, according to the results, it could be speculated that bilobalide might be a pro

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Awakawa, Takayoshi. "Enzymatic reactions in teleocidin B biosynthesis." Journal of Natural Medicines 75, no. 3 (2021): 467–74. http://dx.doi.org/10.1007/s11418-021-01504-2.

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AbstractThe teleocidin B family members are terpene indole compounds isolated from Streptomyces bacteria, and they strongly activate protein kinase C (PKC). Their unique structures have attracted many researchers in the natural product chemistry and pharmacology fields, and numerous isolation and bioactivity studies have been conducted. The accumulated information has facilitated the identification of the enzymatic reactions in teleocidin biosynthesis, and new developments in structural biology have strongly aided efforts to clarify the finer points of these reactions. This review describes th

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Pan, Xinli, Nicole Domin, Sebastian Schieferdecker, Hirokazu Kage, Martin Roth, and Markus Nett. "Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling." Beilstein Journal of Organic Chemistry 13 (November 17, 2017): 2458–65. http://dx.doi.org/10.3762/bjoc.13.242.

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The genome of the predatory bacterium Herpetosiphon aurantiacus 114-95T harbors a number of biosynthesis genes, including four terpene cyclase genes. To identify the terpenes biosynthesized from H. aurantiacus 114-95T, we fed the strain with 13C-labeled glucose and, subsequently, searched for characteristic mass shifts in its metabolome. This approach led to the discovery of a new natural product, of which the isotope pattern is indicative for a diterpene originating from the methylerythritol phosphate pathway. After large-scale fermentation of H. aurantiacus 114-95T, the putative diterpene wa

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Chen, Xinlu, Tobias G. Köllner, Wangdan Xiong, Guo Wei, and Feng Chen. "Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum." Beilstein Journal of Organic Chemistry 15 (November 28, 2019): 2872–80. http://dx.doi.org/10.3762/bjoc.15.281.

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Terpene synthases (TPSs) are pivotal enzymes for the production of diverse terpenes, including monoterpenes, sesquiterpenes, and diterpenes. In our recent studies, dictyostelid social amoebae, also known as cellular slime molds, were found to contain TPS genes for making volatile terpenes. For comparison, here we investigated Physarum polycephalum, a plasmodial slime mold also known as acellular amoeba. Plasmodia of P. polycephalum grown on agar plates were found to release a mixture of volatile terpenoids consisting of four major sesquiterpenes (α-muurolene, (E)-β-caryophyllene, two unidentif

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Tantillo, Dean J. "Biosynthesis via carbocations: Theoretical studies on terpene formation." Natural Product Reports 28, no. 6 (2011): 1035. http://dx.doi.org/10.1039/c1np00006c.

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Hong, Young J., and Dean J. Tantillo. "A potential energy surface bifurcation in terpene biosynthesis." Nature Chemistry 1, no. 5 (2009): 384–89. http://dx.doi.org/10.1038/nchem.287.

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Fellermeier, Monika, Maja Raschke, Silvia Sagner, et al. "Studies on the nonmevalonate pathway of terpene biosynthesis." European Journal of Biochemistry 268, no. 23 (2001): 6302–10. http://dx.doi.org/10.1046/j.0014-2956.2001.02585.x.

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Dickschat, Jeroen S. "Modern Aspects of Isotopic Labellings in Terpene Biosynthesis." European Journal of Organic Chemistry 2017, no. 33 (2017): 4872–82. http://dx.doi.org/10.1002/ejoc.201700482.

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Araki, Yasuko, Takayoshi Awakawa, Motomichi Matsuzaki, et al. "Complete biosynthetic pathways of ascofuranone and ascochlorin inAcremonium egyptiacum." Proceedings of the National Academy of Sciences 116, no. 17 (2019): 8269–74. http://dx.doi.org/10.1073/pnas.1819254116.

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Ascofuranone (AF) and ascochlorin (AC) are meroterpenoids produced by various filamentous fungi, includingAcremonium egyptiacum(synonym:Acremonium sclerotigenum), and exhibit diverse physiological activities. In particular, AF is a promising drug candidate against African trypanosomiasis and a potential anticancer lead compound. These compounds are supposedly biosynthesized through farnesylation of orsellinic acid, but the details have not been established. In this study, we present all of the reactions and responsible genes for AF and AC biosyntheses inA. egyptiacum, identified by heterologou

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Piechulla, Birgit, Nancy Magnus, Marie Chantal Lemfack, and Stephan Von Reuss. "Neue Klasse von Methyltransferasen mit Zyklisierungsaktivität." BIOspektrum 27, no. 1 (2021): 31–33. http://dx.doi.org/10.1007/s12268-021-1506-8.

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AbstractMicroorganisms release small volatile metabolites with unique structures, e. g. the polymethylated homosesquiterpene sodorifen from Serratia plymuthica. Two unusual enzymes with novel features are involved in its biosynthesis, a C-methyltransferase with cyclization activity and a terpene synthase that accepts a non-canonical monocyclic C16 substrate. The novel class of methyltransferases represents an alternative route that enlarges terpene diversity.

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Zhang, Zhiqiang, Wei Liu, Zongbin Ma, Wei Zhu, and Lin Jia. "Transcriptional characterization and response to defense elicitors of mevalonate pathway genes in cotton (Gossypium arboreum L.)." PeerJ 7 (November 20, 2019): e8123. http://dx.doi.org/10.7717/peerj.8123.

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The mevalonate (MVA) pathway is responsible for the biosynthesis of cytosolic terpenes including gossypol and its derivatives, which play an important role in the cotton plant’s defense against pathogens and herbivores. In this study, we identified and cloned 17 potentially functional genes encoding enzymes that catalyze the six steps of the MVA pathway in Gossypium arboreum. Expression pattern analysis by qRT-PCR demonstrated that these genes had tissue-specific expression profiles and were most prevalently expressed in roots. Moreover, these genes were up-regulated in response to several eli

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Chen, Xinlu, Tobias G. Köllner, Qidong Jia, et al. "Terpene synthase genes in eukaryotes beyond plants and fungi: Occurrence in social amoebae." Proceedings of the National Academy of Sciences 113, no. 43 (2016): 12132–37. http://dx.doi.org/10.1073/pnas.1610379113.

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Terpenes are structurally diverse natural products involved in many ecological interactions. The pivotal enzymes for terpene biosynthesis, terpene synthases (TPSs), had been described only in plants and fungi in the eukaryotic domain. In this report, we systematically analyzed the genome sequences of a broad range of nonplant/nonfungus eukaryotes and identified putative TPS genes in six species of amoebae, five of which are multicellular social amoebae from the order of Dictyosteliida. A phylogenetic analysis revealed that amoebal TPSs are evolutionarily more closely related to fungal TPSs tha

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Miao, Wen, Jiaqiang Luo, Junda Liu, Kate Howell, and Pangzhen Zhang. "The Influence of UV on the Production of Free Terpenes in Vitis vinifera cv. Shiraz." Agronomy 10, no. 9 (2020): 1431. http://dx.doi.org/10.3390/agronomy10091431.

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Terpenes contribute to the desirable flavour and aroma of grapes and wine. The biosynthesis of these plant secondary metabolites is influenced by both physiological and environmental factors, such as grapevine phenological stage and sunlight exposure. In this study, we investigated the influence of ultraviolet (UV) at different grapevine phenological stages on free terpenes in grape at harvest. Two types of transparent polymer films were applied to grape bunches to eliminate both UV-A and UV-B or only eliminate UV-B, followed by the identification and quantification of terpenes using headspace

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Malmierca, M. G., S. P. McCormick, R. E. Cardoza, E. Monte, N. J. Alexander, and S. Gutiérrez. "Trichodiene Production in a Trichoderma harzianum erg1-Silenced Strain Provides Evidence of the Importance of the Sterol Biosynthetic Pathway in Inducing Plant Defense-Related Gene Expression." Molecular Plant-Microbe Interactions® 28, no. 11 (2015): 1181–97. http://dx.doi.org/10.1094/mpmi-06-15-0127-r.

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Trichoderma species are often used as biocontrol agents against plant-pathogenic fungi. A complex molecular interaction occurs among the biocontrol agent, the antagonistic fungus, and the plant. Terpenes and sterols produced by the biocontrol fungus have been found to affect gene expression in both the antagonistic fungus and the plant. The terpene trichodiene (TD) elicits the expression of genes related to tomato defense and to Botrytis virulence. We show here that TD itself is able to induce the expression of Botrytis genes involved in the synthesis of botrydial (BOT) and also induces terpen

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Xu, Meimei, P. Ross Wilderman, and Reuben J. Peters. "Following evolution's lead to a single residue switch for diterpene synthase product outcome." Proceedings of the National Academy of Sciences 104, no. 18 (2007): 7397–401. http://dx.doi.org/10.1073/pnas.0611454104.

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There have been few insights into the biochemical origins of natural product biosynthesis from primary metabolism. Of particular interest are terpene synthases, which often mediate the committed step in particular biosynthetic pathways so that alteration of their product outcome is a key step in the derivation of novel natural products. These enzymes also catalyze complex reactions of significant mechanistic interest. Following an evolutionary lead from two recently diverged, functionally distinct diterpene synthase orthologs from different subspecies of rice, we have identified a single resid

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Trapp, Susan C., and Rodney B. Croteau. "Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications." Genetics 158, no. 2 (2001): 811–32. http://dx.doi.org/10.1093/genetics/158.2.811.

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Abstract Terpenoids are the largest, most diverse class of plant natural products and they play numerous functional roles in primary metabolism and in ecological interactions. The first committed step in the formation of the various terpenoid classes is the transformation of the prenyl diphosphate precursors, geranyl diphosphate, farnesyl diphosphate, and geranylgeranyl diphosphate, to the parent structures of each type catalyzed by the respective monoterpene (C10), sesquiterpene (C15), and diterpene synthases (C20). Over 30 cDNAs encoding plant terpenoid synthases involved in primary and seco

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Pemberton, Ryan P., Young J. Hong, and Dean J. Tantillo. "Inherent dynamical preferences in carbocation rearrangements leading to terpene natural products." Pure and Applied Chemistry 85, no. 10 (2013): 1949–57. http://dx.doi.org/10.1351/pac-con-12-11-22.

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An introduction to the application of quantum chemical dynamics calculations to mechanistic problems in the field of terpene biosynthesis is provided. A bare bones introduction to the fundamentals of chemical dynamics is followed by a brief account of previous applications to terpene-forming carbocation reactions, a discussion of questions in this field that dynamics calculations may help answer, and a description of current problems to which dynamics calculations are being applied.

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Okoth, Dorothy A., Joachim J. Hug, Ronald Garcia, Cathrin Spröer, Jörg Overmann, and Rolf Müller. "2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene–Nucleoside." Molecules 25, no. 11 (2020): 2676. http://dx.doi.org/10.3390/molecules25112676.

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Myxobacteria represent an under-investigated source for biologically active natural products featuring intriguing structural moieties with potential applications, e.g., in the pharmaceutical industry. Sorangiadenosine and the here-discovered 2-hydroxysorangiadenosine are myxobacterial sesquiterpene–nucleosides with an unusual structural moiety, a bicyclic eudesmane-type sesquiterpene. As the biosynthesis of these rare terpene–nucleoside hybrid natural products remains elusive, we investigated secondary metabolomes and genomes of several 2-hydroxysorangiadenosine-producing myxobacteria. We repo

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Hare, Stephanie R., and Dean J. Tantillo. "Dynamic behavior of rearranging carbocations – implications for terpene biosynthesis." Beilstein Journal of Organic Chemistry 12 (February 29, 2016): 377–90. http://dx.doi.org/10.3762/bjoc.12.41.

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This review describes unexpected dynamical behaviors of rearranging carbocations and the modern computational methods used to elucidate these aspects of reaction mechanisms. Unique potential energy surface topologies associated with these rearrangements have been discovered in recent years that are not only of fundamental interest, but also provide insight into the way Nature manipulates chemical space to accomplish specific chemical transformations. Cautions for analyzing both experimental and theoretical data on carbocation rearrangements are included throughout.

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Kries, Hajo, Lorenzo Caputi, Clare E. M. Stevenson, et al. "Structural determinants of reductive terpene cyclization in iridoid biosynthesis." Nature Chemical Biology 12, no. 1 (2015): 6–8. http://dx.doi.org/10.1038/nchembio.1955.

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Awakawa, Takayoshi, Lihan Zhang, Toshiyuki Wakimoto, et al. "A Methyltransferase Initiates Terpene Cyclization in Teleocidin B Biosynthesis." Journal of the American Chemical Society 136, no. 28 (2014): 9910–13. http://dx.doi.org/10.1021/ja505224r.

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Darragh, Kathy, Anna Orteu, Daniella Black, et al. "A novel terpene synthase controls differences in anti-aphrodisiac pheromone production between closely related Heliconius butterflies." PLOS Biology 19, no. 1 (2021): e3001022. http://dx.doi.org/10.1371/journal.pbio.3001022.

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Plants and insects often use the same compounds for chemical communication, but not much is known about the genetics of convergent evolution of chemical signals. The terpene (E)-β-ocimene is a common component of floral scent and is also used by the butterfly Heliconius melpomene as an anti-aphrodisiac pheromone. While the biosynthesis of terpenes has been described in plants and microorganisms, few terpene synthases (TPSs) have been identified in insects. Here, we study the recent divergence of 2 species, H. melpomene and Heliconius cydno, which differ in the presence of (E)-β-ocimene; combin

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Abdallah, Ingy I., and Wim J. Quax. "A Glimpse into the Biosynthesis of Terpenoids." KnE Life Sciences 3, no. 5 (2017): 81. http://dx.doi.org/10.18502/kls.v3i5.981.

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<p>Terpenoids represent the largest class of natural products with a diverse array of structures and functions. Many terpenoids have reported therapeutic properties such as antimicrobial, anti-inflammatory, immunomodulatory and chemotherapeutic properties making them of great interest in the medical field. Also, they are widely used in the flavors and fragrances industries, in addition to being a source of biofuels. Terpenoids suffer from low natural yields and complicated chemical synthesis, hence the need for a more sustainable production method. Metabolic engineering provide an excell

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