Functional Identification of Valerena-1,10-diene Synthase, a Terpene Synthase Catalyzing a Unique Chemical Cascade in the Biosynthesis of Biologically Active Sesquiterpenes in Valeriana officinalis*

@article{Yeo2012FunctionalIO,
  title={Functional Identification of Valerena-1,10-diene Synthase, a Terpene Synthase Catalyzing a Unique Chemical Cascade in the Biosynthesis of Biologically Active Sesquiterpenes in Valeriana officinalis*},
  author={Y. Yeo and S. E. Nybo and A. Chittiboyina and A. Weerasooriya and Yan-Hong Wang and E. G{\'o}ngora-Castillo and Brieanne Vaillancourt and C. Buell and D. DellaPenna and M. D. Celiz and A. D. Jones and E. Wurtele and N. Ransom and N. Dudareva and K. Shaaban and N. Tibrewal and S. Chandra and Troy A Smillie and I. Khan and R. Coates and D. Watt and J. Chappell},
  journal={The Journal of Biological Chemistry},
  year={2012},
  volume={288},
  pages={3163 - 3173}
}
Background: Therapeutic values of Valeriana officinalis have been associated with sesquiterpenes whose biosynthetic origins have remained enigmatic. Results: A cyclobutenyl intermediate in the catalytic cascade of valerena-1,10-diene synthase is reported. Conclusion: A new class of sesquiterpene synthases for the biosynthesis of sesquiterpenes harboring isobutenyl functional groups is proposed. Significance: Similar catalytic mechanisms from evolutionarily diverse organisms are proposed and… Expand
De novo synthesis of the sedative valerenic acid in Saccharomyces cerevisiae.
TLDR
These findings showcase Saccharomyces cerevisiae's potential as an expression platform for facilitating multiply-oxidized medicinal terpenoid pathway discovery, possibly paving the way for scale up and FDA approval of valerenic acid and other active compounds from plant-derived herbal medicines. Expand
Investigating sesquiterpene biosynthesis in Ginkgo biloba: molecular cloning and functional characterization of (E,E)-farnesol and α-bisabolene synthases
TLDR
Predictive transcripts potentially encoding enzymes associated with the biosynthesis of diterpenoid and terpenoid compounds, including putative terpene synthases, were first identified by mining publicly-available G. biloba RNA-seq data sets and the phylogenetic analysis revealed the two terPene synthase genes as primitive genes that might have evolved from an ancestral diterpenes synthase. Expand
Regulation of sesquiterpenoid metabolism in recombinant and elicited Valeriana officinalis hairy roots.
TLDR
The findings suggest that the availability of cytoplasmic farnesyl diphosphate and valerenadiene are potential bottlenecks in Valeriana-specific sesquiterpenoid biosynthesis, which is also subject to regulation by methyl jasmonate elicitation. Expand
Molecular Diversity of Terpene Synthases in the Liverwort Marchantia polymorpha[OPEN]
TLDR
Functional characterization and HMMER search tool identified four diterpene synthase genes phylogenetically related to those found in diverged plants and nine rather unusual monoterpene and sesquiterpenes synthase-like genes. Expand
Molecular cloning and characterization of drimenol synthase from valerian plant (Valeriana officinalis)
TLDR
A mechanistic consideration of (−)‐drimenol synthesis suggests that drimenol synthase is likely to use a protonation‐initiated cyclization, which is rare for sesquiterpene synthases. Expand
Recent Developments in Selected Sesquiterpenes: Molecular Rearrangements, Biosynthesis, and Structural Relationship among Congeners
Recent developments in selected sesquiterpenoids are reviewed for the past one decade (2005–2017) with special reference to Mechanisms of multistep molecular rearrangements of some sesquiterpenes orExpand
Metabolic engineering of Escherichia coli for production of valerenadiene 1
8 Valeriana officinalis is a medicinal herb which produces a suite of compounds in its root tissue useful for 9 treatment of anxiety and insomnia. The sesquiterpene components of the root extract,Expand
Cell Wall Extract from Piriformospora indica Enhances Valerenic Acid Content in Valerian Roots via Modulating Sesquiterepene Synthase Genes
Background: Valerenic acid (VA) as a sesquiterpene constituent responsible for medicinal properties is derived from valeriana (Valeriana officinalis). It is well documented that the mutualisticExpand
Biosynthesis of Sesquiterpene Lactones in Plants and Metabolic Engineering for Their Biotechnological Production
In the present chapter, we review some aspects of the biosynthesis of sesquiterpene lactones and its regulation in different medicinal and aromatic plants used in the pharmaceutical industry. In thisExpand
Enhancement of valerenic acid production in Valeriana officinalis roots by methyl jasmonate -mediated transcriptional changes of sesquiterpene synthase genes
TLDR
Exposure to 100 µM MeJA for 24 h can be more effective in the induction of VoTPS1 and VoTPS7 genes than that observed for 50 µM, suggesting that these genes may be responsible for the biosynthesis of intermediates involved in the VA-biosynthetic pathway. Expand
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 44 REFERENCES
Enzymatic synthesis of valerena‐4,7(11)‐diene by a unique sesquiterpene synthase from the valerian plant (Valeriana officinalis)
TLDR
An integrative approach involving next‐generation sequencing and metabolically engineered microbes to expand the knowledge of terpenoid diversity in medicinal plants is demonstrated. Expand
Demonstration of Germacrene A as an Intermediate in 5-Epi-aristolochene Synthase Catalysis
Sesquiterpene synthases are a family of enzymes that catalyze farnesyl pyrophosphate (FPP) cyclization via alternative pathways to produce a variety of cyclic sesquiterpene products. Catalysis byExpand
Metabolic engineering of sesquiterpene metabolism in yeast
TLDR
These yeast now provide a convenient format for investigating catalytic coupling between terpene synthases and hydroxylases, as well as a platform for the industrial production of high value, single‐entity and stereochemically unique terpenes. Expand
The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom.
Some plant terpenes such as sterols and carotenes are part of primary metabolism and found essentially in all plants. However, the majority of the terpenes found in plants are classified asExpand
1.16 – Sesquiterpenes
This chapter reviews recent advances in elucidating the identification and biosynthesis of several classes of sesquiterpenes from a variety of plant and microbial systems. The generation of theExpand
Cloning and Bacterial Expression of a Sesquiterpene Cyclase from Hyoscyamus muticus and Its Molecular Comparison to Related Terpene Cyclases (*)
TLDR
Genomic and cDNA clones for vetispiradiene synthase, a sesquiterpene cyclase found in Hyoscyamus muticus, were isolated using a combination of reverse transcription-polymerase chain reactions and conventional cloning procedures and showed sequence similarity between the tobacco and H. muticus enzymes. Expand
In vitro activity of commercial valerian root extracts against human cytochrome P450 3A4.
TLDR
The findings from this study suggest that valerian root may have an initial inhibitory effect when taken with therapeutic products and how the results can be extrapolated to in vivo situations is unclear. Expand
Redirection of cytosolic or plastidic isoprenoid precursors elevates terpene production in plants
TLDR
The strategy increased synthesis of the sesquiterpenes patchoulol and amorpha-4,11-diene more than 1,000-fold, as well as the monoterpene limonene 10–30 fold, and seems equally suited to generating higher levels of other terpenes for research, industrial production or therapeutic applications. Expand
Pacifigorgianes and tamariscene as constituents of Frullania tamarisci and Valeriana officinalis.
TLDR
Compounds present in both the essential oils of the Frullania species and Valeriana officinalis were enantiomeric to each other, and a plausible biogenetic relationship between the pacifigorgiane, valerenane and tamariscane skeletons is postulated. Expand
Biosynthesis of Abscisic Acid by the Non-mevalonate Pathway in Plants, and by the Mevalonate Pathway in Fungi
TLDR
13C-Labeled β-carotene from the tulip tree showed that the positions of the labeled carbons were the same as those of ABA, being consistent with the biosynthesis of A BA via carotenoids. Expand
...
1
2
3
4
5
...