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opencc-by-4.0May 2022View details →

Chiral monoterpenes reveal forest emission mechanisms and drought responses

This data was obtained during the Biosphere 2 - Water and Life Dynamics measurement campaign between September 2019 and December 2019 inside the Biosphere 2 tropical rainforest, Arizona, USA (DOI: 10.1126/science.abj6789). The Biosphere 2 tropical rainforest was subjected to a 4 month drought and rewetting experiment. This data includes mixing ratios of Isoprene, (-)-alpha-pinene, (+)-alpha-pinene, (-)-beta-pinene, (-)-limonene, (+)-limonene, (-)-camphene, (+)-camphene and gamma-terpinene calculated from data measured with a gas chromatograph - mass spectrometer. This data was sampled to see how the atmospheric concentration of compounds changed due to drought and rewetting. The data also includes the 13C enrichment measurements of chiral monoterpenes and isoprene taken with a gas chromatograph - isotope ratio mass spectrometer and proton reaction mass spectrometer, respectively. The 13C enrichment experiments were conducted on two individual days during the campaign, once during pre-drought and once during the severe drought. This experiment was conducted to see which compounds became enriched in 13C when the atmosphere was exposed to a large amount of 13CO2. Also included are sorbent tube measurements taken from branch cuvettes attached to Piper sp. and Clitoria fairchildiana plants, and also taken from soil chambers. The purpose of these measurements was to see how the emissions or uptakes of compounds from the plants and soil contributed to the total atmospheric concentration. The sorbent tubes were subsequently thermally desorbed into a gas chromatograph time of flight mass spectrometer. Also included is the temperature, photosynthetically active radiation, relative humidity, vapour pressure deficit, soil moisture, and photosynthesis rate data

opencc-by-4.0May 2024View details →

Process-based Modeling of Ecosystem-Level Monoterpene from a Japanese Larch (Larix Kaempferi) Forest

Title ''Process-based Modeling of Ecosystem-Level Monoterpene from a Japanese Larch (Larix Kaempferi) Forest'' Zhanzhuo Chen 1,2, Tomomichi Kato 3, Akihiko Ito 4,5, Tatsuya Miyauchi 3, Yoshiyuki Takahashi 4, and Jing Tang 2 1 Graduate School of Global Food Resources, Hokkaido University, Sapporo, Hokkaido, 060-0809, Japan 2 Center for Volatile Interactions (VOLT), Department of Biology, University of Copenhagen, DK-2100, Copenhagen, Denmark 3 Research Faculty of Agriculture, Hokkaido University, Sapporo, Hokkaido, 060-8589, Japan 4 Earth System Division, National Institute for Environmental Studies (NIES), Onogawa, Tsukuba, Ibaraki, 305-8506, Japan 5 Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan Correspondence to: Tomomichi Kato (tkato@agr.hokudai.ac.jp)

opencc-by-4.0Nov 2019View details →

Supplementary data for the manuscript "Thermodynamic properties of isoprene and monoterpene derived organosulfates estimated with COSMOtherm"

.cosmo and .energy files of various isoprene and monoterpene derived organosulfates and methyl bisulfate (neutral and deprotonated), IEPOX (neutral) and hydrated sodium (cation).

opencc-zeroOct 2022View details →

Broad diversity in monoterpene-sesquiterpene balance across wild sunflowers: implications of leaf and floral volatiles for biotic interactions

• Premise of the study: As plant lineages diversify across environmental gradients, species are predicted to encounter divergent biotic pressures. This study investigates the evolution of volatile secondary metabolism across Helianthus genus. • Methods: Leaves and petals of 40 species of wild Helianthus were analyzed via gas chromatography-mass-spectrometry to describe volatile secondary metabolite profiles. • Key results: Across all species, 500 compounds were identified including 40% sesquiterpenes, 18% monoterpenes, 3% diterpenes, 4% fatty acid derivatives, and 35% other compounds such as phenolics and small organic compounds. Qualitatively, annuals and species from more arid western climates had leaf compositions with a higher proportion of total monoterpenes, while erect perennials and species from more mesic eastern habitats contained a higher proportion of total sesquiterpenes. Among species, mass-based leaf monoterpene and sesquiterpene abundance were identified as largely orthogonal axes of variation by principal components analysis. Leaf and petal profiles were not strongly correlated. • Conclusions: Wide diversity in volatile metabolism was observed among wild Helianthus, indicating value of this genus as a model system, and a rich genetic resource. The independence of leaf and petal volatile profiles indicates a low level of phenotypic integration between vegetative and reproductive structures, implying vegetative defense and reproductive defense or pollinator attraction functions mediated by terpenoid profiles in these two organs can evolve without major tradeoffs. The major biosynthetic pathways manufacturing major terpenoids identified in wild Helianthus have been well described to date, providing a road map to deeper inquiry into the drivers of this diversity.

opencc-zeroJul 2023View details →

Data from: African elephant dietary responses to odors of monoterpene mixtures and individual monoterpenes

The detoxification limitation hypothesis posits that, unless plant defense compounds interact synergistically or additively to increase their harmful effects, generalist herbivores will prefer consuming combinations of these compounds over singular compounds. Monoterpenes are odoriferous defense compounds that may be toxic to mammalian herbivores when ingested in sufficient quantities. Previous research has shown that the addition of individual monoterpenes to food sources reduces consumption by generalist mammalian herbivores. By using African elephants as a case study, we aimed to determine whether odors from monoterpene combinations (i.e., two or more monoterpenes) also deter generalist mammalian herbivory, and whether generalist herbivores prefer the odors of monoterpene combinations over individual monoterpenes. First, we tested whether the odor of monoterpene combinations that resemble the monoterpene profiles of a high-acceptability, intermediate-acceptability, and low-acceptability plant deter herbivory. We found that elephants preferred plants without the added odors of the monoterpene combinations. Second, we explored how elephants responded to individual monoterpenes found within the combinations compared to the combinations at the same set concentration, and found that the elephants did not always prefer the combinations over the individual monoterpenes. Moreover, the more diverse the combination, the less frequently it was preferred when compared to the individual monoterpene odors. Our results imply that generalist herbivores do not necessarily prefer combinations of plant chemical defenses at comparatively lower concentrations and that, consequently, the composition and diversity of monoterpene profiles in plants likely determine the efficacy of these compounds as an olfactory defense against mammalian herbivory.

opencc-by-4.0Aug 2023View details →

Assessment of tobacco and N. benthamiana as biofactories of irregular monoterpenes for sustainable crop protection

Irregular monoterpenes are important precursors of different compounds employed in pest control such as insecticides and insect sex pheromones. Metabolically engineered plants are appealing as biofactories of such compounds, but specially as potential live biodispensers of related bioactive volatiles, which could be continuously emitted to the environment from different plant tissues. Here we assess the use of cultivated tobacco and Nicotiana benthamiana as biofactories for the irregular monoterpenes chrysanthemol and lavandulol. We evaluate the impact of high levels of constitutive metabolite production on the plant physiology and biomass, and their biosynthetic dynamics for different plant tissues and developmental stages. As an example of an active pheromone compound, we super-transformed the best lavandulol-producing tobacco line with an acetyl transferase gene to obtain a tobacco lavandulyl acetate biodispenser producing up to 0.63 mg of lavandulyl acetate per plant every day. We estimate that with these volatile emission levels, between 200 and 500 plants per hectare would be sufficient to ensure a daily emission of pheromones comparable to commercial lures. This is an important step towards plant-based sustainable solutions for pest control, and it lays the ground for further developing biofactories for other irregular monoterpenoid pheromones, whose biosynthetic genes are yet unknown.   The dataset includes GC-MS data (peak areas quantified for each compound with its Qi, normalized) for all the figures and supplementary figures of the associated manuscript. Peak areas are normalized with an admixture, analyzed on the same day as the samples. It also includes biomass data and measurements for the analyzed plants (plant height, leaf biomass, days to flowering time). File S3 shows data for quantitative PCR to determine transgene copy number, and for qRT-PCR to measure transgene expression levels. For all datasets, statistical analysis is also included to support the conclusions showed in the graphs.

ClinicalTrials.gov36/100

Colchicine Plus Phenolic Monoterpenes to Treat COVID-19

ClinicalTrials.gov study NCT04392141. IPD Sharing: NO. Countries: 1. Publications: 7.

closedIPD-NOFeb 2026View details →

publicJul 2023View details →

Data from: African elephant dietary responses to odors of monoterpene mixtures and individual monoterpenes

Open the record for dataset details and reuse information.

publicOct 2022View details →

Broad diversity in monoterpene-sesquiterpene balance across wild sunflowers: implications of leaf and floral volatiles for biotic interactions

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dryad32/100

Functional investigation of monoterpenes for improved understanding of the relationship between hosts and bark beetle

Spruce bark beetle (Ips typographus L.) is the most destructive insect pest of spruce forest in Eurasia. However, contact toxicity, in vivo metabolism, and ecological functions of host monoterpenes are poorly understood at the spruce–bark beetle–predator tritrophic level. Spruce monoterpenes including S-(–)-α-pinene, R-(+)-α-pinene, and myrcene showed contact toxicity to spruce bark beetle, with LD50 values ranging from 24–36 μg/mg. When topically treated with S-(–)-α-pinene or R-(+)-α-pinene, the amount of volatile metabolites [S-(–)-cis-verbenol, 4S-(+)-/4R-(–)-trans-verbenol, and R-(+)-/S-(–)-verbenone] in the hindgut extract of spruce bark beetle varied significantly between sexes, and their quality varied significantly depending on the chirality of α-pinene. More importantly, S-(–)-α-pinene induced male adults to produce large amounts of S-(–)-cis-verbenol and S-(–)-verbenone. When topically treated with myrcene, the expected semiochemicals such as E-myrcenol, ipsenol, and ipsdienol were not detected in beetle hindgut, indicating that the pheromone biosynthetic system of spruce bark beetle does not participate in the metabolism of host myrcene. In the field trapping tests, S-(–)-α-pinene and R-(+)-α-pinene increased the trap catches of spruce bark beetle and Thanasimus substriatus (predator) compared with the pheromone source, whereas myrcene exhibited a strong repellent effect on bark beetle but not on its predator. Our results of contact toxicity, in vivo metabolism, and behavioural activity analyses indicate that spruce bark beetle adopts different ecological strategies to adapt to and tolerate different host monoterpenes; for example, avoidance mechanism for myrcene, and preference mechanism for α-pinene. Signalling interactions among the three monoterpenes at the tritrophic level help us understand their roles in manipulating the arms race between host plants and bark beetles, which indicate the plasticity and multifunctionality of host monoterpenes in the ecological context. Our results can be applied to the management of spruce bark beetle via the push-pull strategy using semiochemicals.

opencc-zeroAug 2020View details →

opencc-by-4.0Oct 2023View details →

Meta-analysis dataset on the temperature sensitivity of monoterpene emissions

The attached file includes the meta-analysis dataset that was used for the study entitled ''High temperature sensitivity of monoterpene emissions from global vegetation ''

opencc-by-4.0Jan 2022View details →

Computational output dataset for monoterpene glycoside hydrolysis: Supplement to 10.5281/zenodo.5346588

Computational data resulting from optimisation and vibrational analysis of monoterpenes, geraniol and linalool, resulting from acid-catalysed hydrolysis of geraniol glucoside. Supplementary dataset for the computation described in: Hixson, Josh, Pisaniello, Lisa, Parker, Mango, Grebneva, Yevgeniya, Bilogrevic, Eleanor, Stegmann, Robin, & Francis, Leigh. (2021, August 31). Methods for predicting and assessing flavour evolution during white wine ageing. https://doi.org/10.5281/zenodo.5346589 Structures were drawn in Avogadro (version 1.2.0), then optimised (UFF) and systematic rotor conformer search performed, with the resulting geometry used to create initial input files for GAMESS (Linux distribution, version 2019 R2, University of Iowa, USA) running on the University of South Australia’s High Performance Compute Cluster. Calculations were first performed for molecules in the gas phase (RHF/3-21G) to provide starting geometries which were then used as the input for density functional theory (B3LYP/6-311G(d)) equilibrium geometry calculations in water (SMD solvent model). Local minima were confirmed by vibrational analysis and the presence of all real frequencies. Each calculation was performed in parallel across eight cores. The chemical structures input into Avagadro and the naming used in computational files can be found in 'starting_structures_naming.png' and the scheme of glucoside hydrolysis and rearrangement from the original manuscript has been re-published here as 'glycoside_hydrolysis_scheme.png'. Two computational output files (.log) are present for each structure: an output of the geometry optimisation ending in '_B3LYP_6311G_aq.log', and; the optimised geometry analysed by vibrational analysis, including thermochemistry, denoted with '_vibrational.log'.  The compounds, compound file naming (starting_structures_naming.png) and structure numbering in the original work (glycoside_hydrolysis_scheme.png) are as follows: geraniol glucoside, geraniol_gluc, compound 1; protonated geraniol glucoside, geraniol_gluc_protonated, compound 2; linalyl or geranyl cation (identical structures found after geometry optimisation), linalyl_cation or geranyl cation, compound 3, protonated geraniol, geraniol_protonated, compound 4; geraniol, geraniol, compound 5; protonated linalool, linalool_protonated, compound 6; linalool, linalool, compound 7.

opencc-by-4.0Sep 2018View details →

Supplementary data for "Computational Investigation of RO2 + HO2 and RO2 + RO2 Reactions of Monoterpene Derived First-Generation Peroxy Radicals Leading to Radical Recycling", revised version submitted to J. Phys. Chem. A

log files (Gaussian 09) and out files (Orca 4.0) (Note: Files_final.zip contains all the same log and out files as Files.zip, but also few additional structures added during the revision process, namely two additional RO2 from ocimene ozonolysis, and one additional transition state for a RO2 + HO2 reaction. Please ignore the file Files.zip.)

Fig. 5 in Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

Fig. 5. The top-scored docking poses of 19 in hBuChE (A, B; PDB ID: 4BDS) and the crystal structure of tacrine bound to hBuChE (C, D). The ligands are displayed in blue (A) and green (C) for 19 and tacrine, respectively; important amino acid residues responsible for ligand anchoring are shown in grey for hBuChE (A, C). Catalytic triad residues are displayed in yellow (A, C). Important interactions are rendered by black dashed lines; distances are measured in angstroms (Å). The rest of the receptor is displayed in light-grey cartoon conformation (A, C). Figures A and C were created with The PyMOL Molecular Graphics System, Version 2.4.1, Schr¨odinger, LLC. 2D figures (B, D) were generated with Maestro 12.3 (Schr¨odinger Release, Schr¨odinger, LLC, New York, NY, 2020). (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 3. Described key 2D in Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

Fig. 3. Described key 2D NMR correlations of revision of previously assigned positions in molecule 17 (COSY interaction – red bond, HMBC interaction – blue arrow). (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

Fig. 4 in Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

Fig. 4. Steady state competitive type inhibition of hBuChE substrate hydrolysis by active compound 19 at different concentrations. Lineweaver Burk plots of initial velocity at increasing substrate concentrations (2.5–10.0 mM) are presented. Lines were derived from a linear regression of the data points. All measurements were made in triplicate and averaged.

Fig. 2. Indole alkaloids with a in Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

Fig. 2. Indole alkaloids with a quebrachamine framework previously described in the literature employing at least 1H NMR analysis. The difference in the H-3 chemical shift of 3-epimers can be valuable for distinguishing between these diastereomers, which is highlighted. It must be mentioned that the C-3 configuration for all compounds shown was described to the contrary in Kutney's article (Kutney et al., 1975). However, the correct configuration of these alkaloids had already been identified by Kompisˇet al. (1968).

Fig. 6. Overlapped top-scored poses for ligands 19 in Monoterpene indole alkaloids from Vinca minor L. (Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

Fig. 6. Overlapped top-scored poses for ligands 19 (blue) and crystal structure of tacrine (green) in the active site of hBuChE (PDB ID: 4BDS). Amino acid residues involved in the interactions with ligands are depicted as either grey or yellow (catalytic triad) lines. The rest of the receptor is displayed in light-grey cartoon conformation. The Figure was created with The PyMOL Molecular Graphics System, Version 2.4.1, Schr¨odinger, LLC. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)

opennotspecifiedJul 2020View details →

Fig. 3 in Leaf isoprene and monoterpene emission distribution across hyperdominant tree genera in the Amazon basin

Fig. 3. Example light (dark blue trace) response curves of leaf photosynthesis (black trace), isoprene emissions (green trace) and monoterpene emissions from an individual in each of the 5 abundant genera including (a) Eschweilera sp., (b) Inga edulis, (c) Protium hebetatum, (d) Pouteria durlandii, (e) Licania oblongifolia. Also shown is an example light response curve from the monoterpene emitting species (f) Pouteria anomala. The dotted line represents a net flux of zero on the photosynthesis axis with negative values in the dark due to leaf respiration. Note that (c) Protium hebetatum is both an isoprene and monoterpene emitter while (f) Pouteria anomala is a monoterpene only emitter.