skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Rapid discovery and functional characterization of terpene synthases from four endophytic xylariaceae

Journal Article · · PLoS ONE
 [1];  [1];  [1];  [2];  [2];  [3];  [4]
  1. Sandia National Lab. (SNL-CA), Livermore, CA (United States)
  2. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Joint BioEnergy Institute, Emeryville, CA (United States)
  3. Sandia National Lab. (SNL-CA), Livermore, CA (United States); Joint BioEnergy Institute, Emeryville, CA (United States)
  4. Michigan State Univ., East Lansing, MI (United States)

© 2016 Wu et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in anymedium, provided the original author and source are credited. Endophytic fungi are ubiquitous plant endosymbionts that establish complex and poorly understood relationships with their host organisms. Many endophytic fungi are known to produce a wide spectrum of volatile organic compounds (VOCs) with potential energy applications, which have been described as "mycodiesel". Many of these mycodiesel hydrocarbons are terpenes, a chemically diverse class of compounds produced by many plants, fungi, and bacteria. Due to their high energy densities, terpenes, such as pinene and bisabolene, are actively being investigated as potential "drop-in" biofuels for replacing diesel and aviation fuel. In this study, we rapidly discovered and characterized 26 terpene synthases (TPSs) derived from four endophytic fungi known to produce mycodiesel hydrocarbons. The TPS genes were expressed in an E. coli strain harboring a heterologous mevalonate pathway designed to enhance terpene production, and their product profiles were determined using Solid Phase Micro-Extraction (SPME) and GC-MS. Out of the 26 TPS's profiled, 12 TPS's were functional, with the majority of them exhibiting both monoterpene and sesquiterpene synthase activity.

Research Organization:
Sandia National Lab. (SNL-CA), Livermore, CA (United States); Sandia National Lab. (SNL-NM), Albuquerque, NM (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Biological and Environmental Research (BER)
Grant/Contract Number:
AC04-94AL85000; AC02-05CH11231
OSTI ID:
1257274
Alternate ID(s):
OSTI ID: 1266786; OSTI ID: 1333928; OSTI ID: 1379058
Report Number(s):
SAND-2015-5056J
Journal Information:
PLoS ONE, Vol. 11, Issue 2; ISSN 1932-6203
Publisher:
Public Library of ScienceCopyright Statement
Country of Publication:
United States
Language:
English
Citation Metrics:
Cited by: 22 works
Citation information provided by
Web of Science

References (72)

Taxadiene synthase structure and evolution of modular architecture in terpene biosynthesis journal December 2010
Evaluation of Combustion Performance of Alternative Aviation Fuels
  • Edwards, Tim; Moses, Cliff; Dryer, Fred
  • 46th AIAA/ASME/SAE/ASEE Joint Propulsion Conference & Exhibit, 46th AIAA/ASME/SAE/ASEE Joint Propulsion Conference & Exhibit https://doi.org/10.2514/6.2010-7155
conference November 2012
Advances in Sesquiterpene Synthases (Cyclases) of Artemisia annua journal November 2007
Identification of the First Bacterial Monoterpene Cyclase, a 1,8-Cineole Synthase, that Catalyzes the Direct Conversion of Geranyl Diphosphate journal July 2011
Investigation of Carbon Metabolism in "Dehalococcoides ethenogenes" Strain 195 by Use of Isotopomer and Transcriptomic Analyses journal June 2009
Mechanism of Monoterpene Cyclization: Stereochemical Aspects of the Transformation of Noncyclizable Substrate Analogs by Recombinant (−)-Limonene Synthase, (+)-Bornyl Diphosphate Synthase, and (−)-Pinene Synthase journal August 2001
Selecting RNA aptamers for synthetic biology: investigating magnesium dependence and predicting binding affinity journal February 2010
Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants journal October 2009
A kinetic model of Escherichia coli core metabolism satisfying multiple sets of mutant flux data journal September 2014
Natural Products from Endophytic Microorganisms journal February 2004
Synergistic Antitumor Effect of α-pinene and β-pinene with Paclitaxel against Non-small-cell Lung Carcinoma (NSCLC) journal September 2014
A role for trans-caryophyllene in the moderation of insulin secretion journal February 2014
Surrogate Splicing for Functional Analysis of Sesquiterpene Synthase Genes journal June 2005
Afferent and motoneuron activity in response to single neuromast stimulation in the posterior lateral line of larval zebrafish journal September 2014
SignalP 4.0: discriminating signal peptides from transmembrane regions journal September 2011
Volatile organic compound production by organisms in the genus Ascocoryne and a re-evaluation of myco-diesel production by NRRL 50072 journal August 2010
cDNA isolation, functional expression, and characterization of (+)-α-pinene synthase and (−)-α-pinene synthase from loblolly pine (Pinus taeda): Stereocontrol in pinene biosynthesis journal March 2003
Spectrometric identifications of sesquiterpene alcohols from niaouli ( Melaleuca quinquenervia ) essential oil journal November 2001
An Endophytic Phomopsis sp. Possessing Bioactivity and Fuel Potential with its Volatile Organic Compounds journal February 2011
The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice journal February 2014
MEGA-CC: computing core of molecular evolutionary genetics analysis program for automated and iterative data analysis journal August 2012
Taxol from fungal endophytes and the issue of biodiversity journal November 1996
Monoterpene Synthases from Grand Fir ( Abies grandis ) : cDNA ISOLATION, CHARACTERIZATION, AND FUNCTIONAL EXPRESSION OF MYRCENE SYNTHASE, (−)-(4 journal August 1997
Cloning and Nucleotide Sequence of the ispA Gene Responsible for Farnesyl Diphosphate Synthase Activity in Escherichia coli11 journal December 1990
Identification and quantification of sesquiterpenes and polyacetylenes in Atractylodes lancea from various geographical origins using GC-MS analysis journal January 2012
Mutational analysis of a monoterpene synthase reaction: Altered catalysis through directed mutagenesis of (−)-pinene synthase from Abies grandis journal July 2005
The biosynthesis of C5–C25 terpenoid compounds journal January 1999
Beta-caryophyllene modulates expression of stress response genes and mediates longevity in Caenorhabditis elegans journal September 2014
The cannabinoid receptor 2 agonist, β-caryophyllene, reduced voluntary alcohol intake and attenuated ethanol-induced place preference and sensitivity in mice journal September 2014
The genome of Eucalyptus grandis journal June 2014
Linalool and β-pinene exert their antidepressant-like activity through the monoaminergic pathway journal May 2015
Characterization of δ-Guaiene Synthases from Cultured Cells of Aquilaria , Responsible for the Formation of the Sesquiterpenes in Agarwood journal October 2010
Anti-tumor effect of α-pinene on human hepatoma cell lines through inducing G2/M cell cycle arrest journal March 2015
The cannabinoid CB2 receptor-selective phytocannabinoid beta-caryophyllene exerts analgesic effects in mouse models of inflammatory and neuropathic pain journal April 2014
The production of myco-diesel hydrocarbons and their derivatives by the endophytic fungus Gliocladium roseum (NRRL 50072) journal December 2010
Cloning and Functional Characterization of a β-Pinene Synthase from Artemisia annua That Shows a Circadian Pattern of Expression journal August 2002
The story of mycodiesel journal June 2014
The production of myco-diesel hydrocarbons and their derivatives by the endophytic fungus Gliocladium roseum (NRRL 50072) journal November 2008
Trans-caryophyllene suppresses tumor necrosis factor (TNFα)-induced inflammation in human chondrocytes journal August 2014
The rice (E)-β-caryophyllene synthase (OsTPS3) accounts for the major inducible volatile sesquiterpenes journal June 2007
Volatile Terpenes from Actinomycetes: A Biosynthetic Study Correlating Chemical Analyses to Genome Data journal October 2013
The cannabinoid receptor 2 agonist β-caryophyllene reduces voluntary alcohol intake and attenuated ethanol-induced place preference and sensitivity in mice journal January 2015
A Maize ( E )-β-Caryophyllene Synthase Implicated in Indirect Defense Responses against Herbivores Is Not Expressed in Most American Maize Varieties journal February 2008
Monoterpene synthase activities in leaves of Picea abies (L.) Karst. and Quercus ilex L. journal June 2000
An Endophytic Nodulisporium sp. from Central America Producing Volatile Organic Compounds with Both Biological and Fuel Potential journal January 2013
Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production journal September 2013
Terpene Biosynthesis: Modularity Rules journal November 2011
Building carbon–carbon bonds using a biocatalytic methanol condensation cycle journal October 2014
The biosynthesis of C5–C25 terpenoid compounds journal January 1997
Two sesquiterpene synthases are responsible for the complex mixture of sesquiterpenes emitted from Arabidopsis flowers: Sesquiterpene synthases in Arabidopsis flower journal April 2005
Geranyl diphosphate synthase from Abies grandis: cDNA isolation, functional expression, and characterization journal September 2002
Two nearly identical terpene synthases catalyze the formation of nerolidol and linalool in snapdragon flowers journal July 2008
Insecticidal and nematicidal essential oils from Argentinean Eupatorium and Baccharis spp. journal August 2012
Muscodor albus MOW12 an Endophyte of Piper nigrum L. (Piperaceae) Collected from North East India Produces Volatile Antimicrobials journal March 2013
Genomic organization of δ-guaiene synthase genes in Aquilaria crassna and its possible use for the identification of Aquilaria species journal April 2011
Altering product outcome in Abies grandis (−)-limonene synthase and (−)-limonene/(−)-α-pinene synthase by domain swapping and directed mutagenesis journal May 2004
Chemical Composition of Leaf Essential Oil of Syzygium densiflorum Wall. ex Wt. & Arn.- A Vulnerable Tree Species journal January 2012
The biosynthesis of C5–C25 terpenoid compounds journal January 2002
Identification and characterization of (E)-β-caryophyllene synthase and α/β-pinene synthase potentially involved in constitutive and herbivore-induced terpene formation in cotton journal December 2013
Evaluation of the anti-inflammatory, anti-catabolic and pro-anabolic effects of E-caryophyllene, myrcene and limonene in a cell model of osteoarthritis journal March 2015
Modulation of volatile organic compound formation in the Mycodiesel-producing endophyte Hypoxylon sp. CI-4 journal February 2012
Hypoxylon sp., an Endophyte of Persea indica, Producing 1,8-Cineole and Other Bioactive Volatiles with Fuel Potential journal October 2010
Neuroprotective Effects of Trans-Caryophyllene Against Kainic Acid Induced Seizure Activity and Oxidative Stress in Mice journal November 2014
Isolation, Characterization, and Mechanistic Studies of (−)-α-Gurjunene Synthase fromSolidago canadensis journal April 1999
Muscodor sutura, a novel endophytic fungus with volatile antibiotic activities journal July 2012
Identification of a Fungal 1,8-Cineole Synthase from Hypoxylon sp. with Specificity Determinants in Common with the Plant Synthases journal February 2015
Sesquiterpene Synthases from Grand Fir ( Abies grandis ) : COMPARISON OF CONSTITUTIVE AND WOUND-INDUCED ACTIVITIES, AND cDNA ISOLATION, CHARACTERIZATION, AND BACTERIAL EXPRESSION OF δ-SELINENE SYNTHASE AND γ-HUMULENE SYNTHASE journal January 1998
Thermal Rearrangements of Monoterpenes and Monoterpenoids journal September 2009
An endophytic/pathogenic Phoma sp. from creosote bush producing biologically active volatile compounds having fuel potential: Endophytic Phoma sp. and its VOCs journal May 2011
Production of isoprenoid pharmaceuticals by engineered microbes journal November 2006
Global Transcriptional, Physiological, and Metabolite Analyses of the Responses of Desulfovibrio vulgaris Hildenborough to Salt Adaptation journal December 2009
Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration. journal January 1984

Cited By (5)

Characterization of four endophytic fungi as potential consolidated bioprocessing hosts for conversion of lignocellulose into advanced biofuels journal January 2017
Engineering Escherichia coli for the production of terpene mixture enriched in caryophyllene and caryophyllene alcohol as potential aviation fuel compounds journal June 2018
Sesquiterpenes in grapes and wines: Occurrence, biosynthesis, functionality, and influence of winemaking processes journal December 2019
Diversity of biologically active secondary metabolites from endophytic and saprotrophic fungi of the ascomycete order Xylariales journal January 2018
Foliar endophytic fungi: diversity in species and functions in forest ecosystems journal January 2020

Similar Records

Microbial-type terpene synthase genes occur widely in nonseed land plants, but not in seed plants
Journal Article · Mon Oct 10 00:00:00 EDT 2016 · Proceedings of the National Academy of Sciences of the United States of America · OSTI ID:1257274

Biosynthesis and Emission of Stress-Induced Volatile Terpenes in Roots and Leaves of Switchgrass (Panicum virgatum L.)
Journal Article · Thu Sep 19 00:00:00 EDT 2019 · Frontiers in Plant Science · OSTI ID:1257274

Further engineering of R. toruloides for the production of terpenes from lignocellulosic biomass
Journal Article · Wed Apr 21 00:00:00 EDT 2021 · Biotechnology for Biofuels · OSTI ID:1257274