Plant diterpenoid metabolism for manufacturing the biopharmaceuticals of tomorrow: prospects and challenges

A (–)-kolavenyl diphosphate synthase catalyzes the first step of salvinorin A biosynthesis in Salvia divinorum

(2017) Xiaoyue Chen et al.   JOURNAL OF EXPERIMENTAL BOTANY

cis or trans with class II diterpene cyclases

(2017) Meirong Jia et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Biosynthesis of the psychotropic plant diterpene salvinorin A: Discovery and characterization of theSalvia divinorumclerodienyl diphosphate synthase

(2017) Kyle A. Pelot et al.   PLANT JOURNAL

The terpene synthase gene family inTripterygium wilfordiiharbors a labdane-type diterpene synthase among the monoterpene synthase TPS-b subfamily

(2017) Nikolaj L. Hansen et al.   PLANT JOURNAL

Functional Diversification of Kaurene Synthase-Like Genes in Isodon rubescens

(2017) Baolong Jin et al.   PLANT PHYSIOLOGY

Biosynthesis of the microtubule-destabilizing diterpene pseudolaric acid B from golden larch involves an unusual diterpene synthase

(2017) Sibongile Mafu et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Biosynthesis of the oxygenated diterpene nezukol in the medicinal plant Isodon rubescens is catalyzed by a pair of diterpene synthases

(2017) Kyle A. Pelot et al.   PLoS One

Expanding the Landscape of Diterpene Structural Diversity through Stereochemically Controlled Combinatorial Biosynthesis

(2016) Johan Andersen-Ranberg et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Substitution of Two Active-Site Residues Alters C9-Hydroxylation in a Class II Diterpene Synthase

(2016) Sibongile Mafu et al.   CHEMBIOCHEM

Total Synthesis of (−)-Salvinorin A

(2016) Nathan J. Line et al.   CHEMISTRY-A EUROPEAN JOURNAL

Engineering biosynthesis of high-value compounds in photosynthetic organisms

(2016) Ellis C. O’Neill et al.   CRITICAL REVIEWS IN BIOTECHNOLOGY

Omics data input for metabolic modeling

(2016) Amit Rai et al.   CURRENT OPINION IN BIOTECHNOLOGY

Cyanobacterial metabolic engineering for biofuel and chemical production

(2016) Neal J Oliver et al.   CURRENT OPINION IN CHEMICAL BIOLOGY

Enhanced Diterpene Tanshinone Accumulation and Bioactivity of Transgenic Salvia miltiorrhiza Hairy Roots by Pathway Engineering

(2016) Min Shi et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Transient production of artemisinin in Nicotiana benthamiana is boosted by a specific lipid transfer protein from A. annua

(2016) Bo Wang et al.   METABOLIC ENGINEERING

Extreme promiscuity of a bacterial and a plant diterpene synthase enables combinatorial biosynthesis

(2016) Meirong Jia et al.   METABOLIC ENGINEERING

Production of the forskolin precursor 11β-hydroxy-manoyl oxide in yeast using surrogate enzymatic activities

(2016) Codruta Ignea et al.   Microbial Cell Factories

Product Rearrangement from Altering a Single Residue in the Rice syn-Copalyl Diphosphate Synthase

(2016) Kevin C. Potter et al.   ORGANIC LETTERS

Integrative Approaches for the Identification and Localization of Specialized Metabolites in Tripterygium Roots

(2016) B. Markus Lange et al.   PLANT PHYSIOLOGY

Oxidation and cyclization of casbene in the biosynthesis ofEuphorbiafactors from mature seeds ofEuphorbia lathyrisL.

(2016) Dan Luo et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Carnosic acid biosynthesis elucidated by a synthetic biology platform

(2016) Codruta Ignea et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Probing the promiscuity ofent-kaurene oxidases via combinatorial biosynthesis

(2016) Sibongile Mafu et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Enhanced limonene production in cyanobacteria reveals photosynthesis limitations

(2016) Xin Wang et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Plant metabolism, the diverse chemistry set of the future

(2016) E. T. Wurtzel et al.   SCIENCE

Characterization of a dynamic metabolon producing the defense compound dhurrin in sorghum

(2016) Tomas Laursen et al.   SCIENCE

Elucidation of the biosynthesis of carnosic acid and its reconstitution in yeast

(2016) Ulschan Scheler et al.   Nature Communications

Antibody therapeutics for Ebola virus disease

(2016) Larry Zeitlin et al.   Current Opinion in Virology

Establishment of Tripterygium wilfordii Hook. f. Hairy Root Culture and Optimization of Its Culture Conditions for the Production of Triptolide and Wilforine

(2016) Chuanshu Zhu et al.   JOURNAL OF MICROBIOLOGY AND BIOTECHNOLOGY

Ginkgolide B Exerts Cardioprotective Properties against Doxorubicin-Induced Cardiotoxicity by Regulating Reactive Oxygen Species, Akt and Calcium Signaling Pathways In Vitro and In Vivo

(2016) Junqing Gao et al.   PLoS One

Investigation of the Chemical Interface in the Soybean–Aphid and Rice–Bacteria Interactions Using MALDI-Mass Spectrometry Imaging

(2015) Adam T. Klein et al.   ANALYTICAL CHEMISTRY

Blocking Deprotonation with Retention of Aromaticity in a Plant ent -Copalyl Diphosphate Synthase Leads to Product Rearrangement

(2015) Kevin C. Potter et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Functional characterization of ent-copalyl diphosphate synthase from Andrographis paniculata with putative involvement in andrographolides biosynthesis

(2015) Qinqin Shen et al.   BIOTECHNOLOGY LETTERS

Diterpenes from rosemary (Rosmarinus officinalis): Defining their potential for anti-cancer activity

(2015) Sakina M. Petiwala et al.   CANCER LETTERS

Metabolic engineering of the Stevia rebaudiana ent-kaurene biosynthetic pathway in recombinant Escherichia coli

(2015) Min Kyung Kong et al.   JOURNAL OF BIOTECHNOLOGY

Minnelide Overcomes Oxaliplatin Resistance by Downregulating the DNA Repair Pathway in Pancreatic Cancer

(2015) Shrey Modi et al.   JOURNAL OF GASTROINTESTINAL SURGERY

Reconstructing the chemical diversity of labdane-type diterpene biosynthesis in yeast

(2015) Codruta Ignea et al.   METABOLIC ENGINEERING

Efficient diterpene production in yeast by engineering Erg20p into a geranylgeranyl diphosphate synthase

(2015) Codruta Ignea et al.   METABOLIC ENGINEERING

The Application of Synthetic Biology to Elucidation of Plant Mono-, Sesqui-, and Diterpenoid Metabolism

(2015) Naoki Kitaoka et al.   Molecular Plant

Modern plant metabolomics: advanced natural product gene discoveries, improved technologies, and future prospects

(2015) Lloyd W. Sumner et al.   NATURAL PRODUCT REPORTS

Cytochrome P450 promiscuity leads to a bifurcating biosynthetic pathway for tanshinones

(2015) Juan Guo et al.   NEW PHYTOLOGIST

Minnelide, a novel drug for pancreatic and liver cancer

(2015) Sulagna Banerjee et al.   PANCREATOLOGY

Carnosic acid

(2015) Simona Birtić et al.   PHYTOCHEMISTRY

Moss-made pharmaceuticals: from bench to bedside

(2015) Ralf Reski et al.   PLANT BIOTECHNOLOGY JOURNAL

Sclareol production in the moss Physcomitrella patens and observations on growth and terpenoid biosynthesis

(2015) Xi-Wu Pan et al.   Plant Biotechnology Reports

Engineering low phorbol ester Jatropha curcas seed by intercepting casbene biosynthesis

(2015) Chunhong Li et al.   PLANT CELL REPORTS

Orthologs of the archaeal isopentenyl phosphate kinase regulate terpenoid production in plants

(2015) Laura K. Henry et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Computational-guided discovery and characterization of a sesquiterpene synthase fromStreptomyces clavuligerus

(2015) Jeng-Yeong Chow et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Complete biosynthesis of opioids in yeast

(2015) S. Galanie et al.   SCIENCE

Plant diterpene synthases: exploring modularity and metabolic diversity for bioengineering

(2015) Philipp Zerbe et al.   TRENDS IN BIOTECHNOLOGY

Metabolic Engineering of Synechocystis sp. PCC 6803 for Production of the Plant Diterpenoid Manoyl Oxide

(2015) Elias Englund et al.   ACS Synthetic Biology

Stable heterologous expression of biologically active terpenoids in green plant cells

(2015) N. Kusaira B. K. Ikram et al.   Frontiers in Plant Science

Heterologous expression of the isopimaric acid pathway in Nicotiana benthamiana and the effect of N-terminal modifications of the involved cytochrome P450 enzyme

(2015) Thiyagarajan Gnanasekaran et al.   Journal of Biological Engineering

Towards Elucidating Carnosic Acid Biosynthesis in Lamiaceae: Functional Characterization of the Three First Steps of the Pathway in Salvia fruticosa and Rosmarinus officinalis

(2015) Dragana Božić et al.   PLoS One

Metabolic engineering for the high-yield production of isoprenoid-based C5 alcohols in E. coli

(2015) Kevin W. George et al.   Scientific Reports

To Gibberellins and Beyond! Surveying the Evolution of (Di)Terpenoid Metabolism

(2014) Jiachen Zi et al.   Annual Review of Plant Biology

Microbial Synthesis of the Forskolin Precursor Manoyl Oxide in an Enantiomerically Pure Form

(2014) Morten T. Nielsen et al.   APPLIED AND ENVIRONMENTAL MICROBIOLOGY

Combining metabolomics and transcriptomics to characterize tanshinone biosynthesis in Salvia miltiorrhiza

(2014) Wei Gao et al.   BMC GENOMICS

Formal Total Synthesis of (−)-Taxol through Pd-Catalyzed Eight-Membered Carbocyclic Ring Formation

(2014) Sho Hirai et al.   CHEMISTRY-A EUROPEAN JOURNAL

Biotechnological production of natural zero-calorie sweeteners

(2014) Ryan N Philippe et al.   CURRENT OPINION IN BIOTECHNOLOGY

Synthesis and κ-Opioid Receptor Activity of Furan-Substituted Salvinorin A Analogues

(2014) Andrew P. Riley et al.   JOURNAL OF MEDICINAL CHEMISTRY

Biosynthesis of Lycosantalonol, a cis-Prenyl Derived Diterpenoid

(2014) Jiachen Zi et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Mass spectrometry imaging of plant metabolites – principles and possibilities

(2014) Nanna Bjarnholt et al.   NATURAL PRODUCT REPORTS

Semi-synthetic artemisinin: a model for the use of synthetic biology in pharmaceutical development

(2014) Chris J. Paddon et al.   NATURE REVIEWS MICROBIOLOGY

Salvinorin A regulates dopamine transporter function via a kappa opioid receptor and ERK1/2-dependent mechanism

(2014) Bronwyn Kivell et al.   NEUROPHARMACOLOGY

Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary (Rosmarinus officinalis) glandular trichomes

(2014) Kathleen Brückner et al.   PHYTOCHEMISTRY

Production of Bioactive Diterpenoids in the Euphorbiaceae Depends on Evolutionarily Conserved Gene Clusters

(2014) A. J. King et al.   PLANT CELL

Metabolic engineering of Nicotiana benthamiana for the increased production of taxadiene

(2014) Md. Mohidul Hasan et al.   PLANT CELL REPORTS

Diterpene synthases of the biosynthetic system of medicinally active diterpenoids inMarrubium vulgare

(2014) Philipp Zerbe et al.   PLANT JOURNAL

Biosynthesis, elicitation and roles of monocot terpenoid phytoalexins

(2014) Eric A. Schmelz et al.   PLANT JOURNAL

Manoyl Oxide (13R), the Biosynthetic Precursor of Forskolin, Is Synthesized in Specialized Root Cork Cells in Coleus forskohlii

(2014) I. Pateraki et al.   PLANT PHYSIOLOGY

Investigation of terpene diversification across multiple sequenced plant genomes

(2014) Alexander M. Boutanaev et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Metabolic engineering of the moss Physcomitrella patens to produce the sesquiterpenoids patchoulol and α/β-santalene

(2014) Xin Zhan et al.   Frontiers in Plant Science

Data access for the 1,000 Plants (1KP) project

(2014) Naim Matasci et al.   GigaScience

Network Analysis of the MVA and MEP Pathways for Isoprenoid Synthesis

(2013) Eva Vranová et al.   Annual Review of Plant Biology

1.55Å-resolution structure of ent-copalyl diphosphate synthase and exploration of general acid function by site-directed mutagenesis

(2013) Mustafa Köksal et al.   BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS

Gene clustering in plant specialized metabolism

(2013) Hans-Wilhelm Nützmann et al.   CURRENT OPINION IN BIOTECHNOLOGY

The 2-methoxy methyl analogue of salvinorin A attenuates cocaine-induced drug seeking and sucrose reinforcements in rats

(2013) Aashish S. Morani et al.   EUROPEAN JOURNAL OF PHARMACOLOGY

High-level semi-synthetic production of the potent antimalarial artemisinin

(2013) C. J. Paddon et al.   NATURE

The metabolite chemotype ofNicotiana benthamianatransiently expressing artemisinin biosynthetic pathway genes is a function ofCYP71AV1type and relative gene dosage

(2013) Hieng-Ming Ting et al.   NEW PHYTOLOGIST

Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae

(2013) Jiachen Zi et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Plant P450s as versatile drivers for evolution of species-specific chemical diversity

(2013) B. Hamberger et al.   PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY B-BIOLOGICAL SCIENCES

Formation of the Unusual Semivolatile Diterpene Rhizathalene by the Arabidopsis Class I Terpene Synthase TPS08 in the Root Stele Is Involved in Defense against Belowground Herbivory

(2013) M. M. Vaughan et al.   PLANT CELL

Evolution of a Complex Locus for Terpene Biosynthesis in Solanum

(2013) Y. Matsuba et al.   PLANT CELL

High-level diterpene production by transient expression in Nicotiana benthamiana

(2013) Kathleen Brückner et al.   Plant Methods

Gene Discovery of Modular Diterpene Metabolism in Nonmodel Systems

(2013) P. Zerbe et al.   PLANT PHYSIOLOGY

CYP76AH1 catalyzes turnover of miltiradiene in tanshinones biosynthesis and enables heterologous production of ferruginol in yeasts

(2013) J. Guo et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

14-Step Synthesis of (+)-Ingenol from (+)-3-Carene

(2013) L. Jorgensen et al.   SCIENCE

Production of miltiradiene by metabolically engineeredSaccharomyces cerevisiae

(2012) Zhubo Dai et al.   BIOTECHNOLOGY AND BIOENGINEERING

Discovery and functional characterization of two diterpene synthases for sclareol biosynthesis in Salvia sclarea (L.) and their relevance for perfume manufacture

(2012) Anne Caniard et al.   BMC PLANT BIOLOGY

Insights into Diterpene Cyclization from Structure of Bifunctional Abietadiene Synthase fromAbies grandis

(2012) Ke Zhou et al.   JOURNAL OF BIOLOGICAL CHEMISTRY

Toward a Biosynthetic Route to Sclareol and Amber Odorants

(2012) Michel Schalk et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthetic biology and the development of tools for metabolic engineering

(2012) Jay D. Keasling   METABOLIC ENGINEERING

Microbial engineering for the production of advanced biofuels

(2012) Pamela P. Peralta-Yahya et al.   NATURE

Neanderthal medics? Evidence for food, cooking, and medicinal plants entrapped in dental calculus

(2012) Karen Hardy et al.   NATURWISSENSCHAFTEN

A Single Residue Change Leads to a Hydroxylated Product from the Class II Diterpene Cyclization Catalyzed by Abietadiene Synthase

(2012) Jared Criswell et al.   ORGANIC LETTERS

Characterization of two genes for the biosynthesis of the labdane diterpeneZ-abienol in tobacco (Nicotiana tabacum)glandular trichomes

(2012) Christophe Sallaud et al.   PLANT JOURNAL

Mining the Biodiversity of Plants: A Revolution in the Making

(2012) V. De Luca et al.   SCIENCE

Pine terpenoid defences in the mountain pine beetle epidemic and in other conifer pest interactions: specialized enemies are eating holes into a diverse, dynamic and durable defence system

(2012) J. Bohlmann   TREE PHYSIOLOGY

Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals

(2011) Dana Morrone et al.   BIOCHEMICAL JOURNAL

A Novel Labda-7,13E-dien-15-ol-Producing Bifunctional Diterpene Synthase from Selaginella moellendorffii

(2011) Sibongile Mafu et al.   CHEMBIOCHEM

A short-chain dehydrogenase involved in terpene metabolism from Zingiber zerumbet

(2011) Sho Okamoto et al.   FEBS Journal

Recent advances towards development and commercialization of plant cell culture processes for the synthesis of biomolecules

(2011) Sarah A. Wilson et al.   PLANT BIOTECHNOLOGY JOURNAL

The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom

(2011) Feng Chen et al.   PLANT JOURNAL

Synthetic biosystems for the production of high-value plant metabolites

(2011) Peter J. Facchini et al.   TRENDS IN BIOTECHNOLOGY

Two rings in them all: The labdane-related diterpenoids

(2010) Reuben J. Peters   NATURAL PRODUCT REPORTS

Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis

(2010) Mustafa Köksal et al.   NATURE

Cloning of casbene and neocembrene synthases from Euphorbiaceae plants and expression in Saccharomyces cerevisiae

(2010) James Kirby et al.   PHYTOCHEMISTRY

Nicotiana benthamiana as a Production Platform for Artemisinin Precursors

(2010) Teun W. J. M. van Herpen et al.   PLoS One

Combining metabolic and protein engineering of a terpenoid biosynthetic pathway for overproduction and selectivity control

(2010) E. Leonard et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA

Isoprenoid Pathway Optimization for Taxol Precursor Overproduction in Escherichia coli

(2010) P. K. Ajikumar et al.   SCIENCE

Increasing diterpene yield with a modular metabolic engineering system in E. coli: comparison of MEV and MEP isoprenoid precursor pathway engineering

(2009) Dana Morrone et al.   APPLIED MICROBIOLOGY AND BIOTECHNOLOGY

Production of taxa-4(5),11(12)-diene by transgenic Physcomitrella patens

(2009) Aldwin Anterola et al.   TRANSGENIC RESEARCH

Variability in Content of the Anti-AIDS Drug Candidate Prostratin in Samoan Populations ofHomalanthus nutans

(2008) Holly E. Johnson et al.   JOURNAL OF NATURAL PRODUCTS

Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (Paclitaxel) production

(2008) Benedikt Engels et al.   METABOLIC ENGINEERING

Total Synthesis of the Hallucinogenic Neoclerodane Diterpenoid Salvinorin A

(2008) Masato Nozawa et al.   ORGANIC LETTERS

Terpenoid biomaterials

(2008) Jörg Bohlmann et al.   PLANT JOURNAL

A Role for a Menthone Reductase in Resistance against Microbial Pathogens in Plants

(2008) H. W. Choi et al.   PLANT PHYSIOLOGY

Functional plasticity of paralogous diterpene synthases involved in conifer defense

(2008) C. I. Keeling et al.   PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA