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PloS One 2012The pinewood nematode (PWN) Bursaphelenchus xylophilus, vectored primarily by the sawyer beetle, Monochamus alternatus, is an important invasive pest and causal agent of...
The pinewood nematode (PWN) Bursaphelenchus xylophilus, vectored primarily by the sawyer beetle, Monochamus alternatus, is an important invasive pest and causal agent of pine wilt disease of Chinese Masson pine, Pinus massoniana. Previous work demonstrated that the ratios and concentrations of α-pinene:β-pinene differed between healthy trees and those trees containing blue-stain fungus (and M. alternatus pupae). However, the potential influence of the altered monoterpene ratios and concentrations on PWN and associated fungi remained unknown. Our current results show that low concentrations of the monoterpenes within petri dishes reduced PWN propagation, whereas the highest concentration of the monoterpenes increased PWN propagation. The propagation rate of PWN treated with the monoterpene ratio representative of blue-stain infected pine (α-pinene:β-pinene = 1:0.8, 137.6 mg/ml) was significantly higher than that (α-pinene:β-pinene = 1:0.1, 137.6 mg/ml) representative of healthy pines or those damaged by M. alternatus feeding, but without blue stain. Furthermore, inhibition of mycelial growth of associated fungi increased with the concentration of the monoterpenes α-pinene and β-pinene. Additionally, higher levels of β-pinene (α-pinene:β-pinene = 1:0.8) resulted in greater inhibition of the growth of the associated fungi Sporothrix sp.2 and Ophiostoma ips strains, but had no significant effects on the growth of Sporothrix sp.1, which is the best food resource for PWN. These results suggest that host monoterpenes generally reduce the reproduction of PWN. However, PWN utilizes high monoterpene concentrations and native blue-stain fungus Sporothrix sp.1 to improve its own propagation and overcome host resistance, which may provide clues to understanding the ecological mechanisms of PWN's successful invasion.
Topics: Animals; Bicyclic Monoterpenes; Biological Assay; Bridged Bicyclo Compounds; Fertility; Monoterpenes; Mycelium; Nematoda; Pinus; Population Dynamics; Sporothrix; Staining and Labeling; Volatilization
PubMed: 22363713
DOI: 10.1371/journal.pone.0031716 -
Recent Patents on Anti-infective Drug... Apr 2012During the last few years the scientific community has shown a considerable interest in the study of plant materials as sources of new compounds to be processed into... (Review)
Review
During the last few years the scientific community has shown a considerable interest in the study of plant materials as sources of new compounds to be processed into antimicrobial agents. In this context, carvacrol, a monoterpenic phenol, has emerged for its wide spectrum activity extended to food spoilage or pathogenic fungi, yeast and bacteria as well as human, animal and plant pathogenic microorganisms including drug-resistant and biofilm forming microorganisms. The antibacterial activity of carvacrol has been attributed to its considerable effects on the structural and functional properties of cytoplasmatic membrane. The data reported in this review provide an overview of the published literature regarding the antimicrobial properties of carvacrol and the recent patents claimed in order to highlight its future applications as a new antimicrobial agent. These could concern either the natural preservation in the cosmetic and food industries or an alternative which supports the conventional antimicrobial protocols. Interestingly, carvacrol alone or associated with one or more synergistic products could be incorporated in different formulations for biomedical and food packaging applications. However, more detailed safety investigations and in vivo studies should be carried out so that this molecule could be used in the future.
Topics: Animals; Anti-Infective Agents; Bacteria; Bacterial Infections; Cymenes; Fungi; Humans; Monoterpenes; Mycoses
PubMed: 22044355
DOI: 10.2174/157489112799829684 -
Molecules (Basel, Switzerland) Jan 2021By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular... (Review)
Review
By the end of the twentieth century, the interest in natural compounds as probable sources of drugs has declined and was replaced by other strategies such as molecular target-based drug discovery. However, in the recent times, natural compounds regained their position as extremely important source drug leads. Indole-containing compounds are under clinical use which includes vinblastine and vincristine (anticancer), atevirdine (anti-HIV), yohimbine (erectile dysfunction), reserpine (antihypertension), ajmalicine (vascular disorders), ajmaline (anti-arrhythmic), vincamine (vasodilator), etc. Monoterpene Indole Alkaloids (MIAs) deserve the curiosity and attention of researchers due to their chemical diversity and biological activities. These compounds were considered as an impending source of drug-lead. In this review 444 compounds, were identified from six genera belonging to the family Apocynaceae, will be discussed. These genera (, , , , and and ) consist of 400 members and represent 20% of Apocynaceae species. Only 30 (7.5%) species were investigated, whereas the rest are promising to be investigated. Eleven bioactivities, including antibacterial, antifungal, anti-inflammatory and immunosuppressant activities, were reported. Whereas cytotoxic effect represents 47% of the reported activities. Convincingly, the genera selected in this review are a wealthy source for future anticancer drug lead.
Topics: Apocynaceae; Indole Alkaloids; Molecular Structure; Monoterpenes; Plant Extracts
PubMed: 33477682
DOI: 10.3390/molecules26020488 -
Natural Product Reports Aug 2006
Review
Topics: Biological Products; Indole Alkaloids; Molecular Structure; Monoterpenes
PubMed: 16874388
DOI: 10.1039/b512615k -
Phytochemistry 2009The multitude of terpene carbon skeletons in plants is formed by enzymes known as terpene synthases. This review covers the monoterpene and sesquiterpene synthases... (Review)
Review
The multitude of terpene carbon skeletons in plants is formed by enzymes known as terpene synthases. This review covers the monoterpene and sesquiterpene synthases presenting an up-to-date list of enzymes reported and evidence for their ability to form multiple products. The reaction mechanisms of these enzyme classes are described, and information on how terpene synthase proteins mediate catalysis is summarized. Correlations between specific amino acid motifs and terpene synthase function are described, including an analysis of the relationships between active site sequence and cyclization type and a discussion of whether specific protein features might facilitate multiple product formation.
Topics: Alkyl and Aryl Transferases; Molecular Structure; Monoterpenes; Mutagenesis, Site-Directed; Plants; Sesquiterpenes; Structure-Activity Relationship
PubMed: 19793600
DOI: 10.1016/j.phytochem.2009.07.030 -
European Journal of Medicinal Chemistry Sep 2019Carvacrol (CAR), a natural monoterpene particularly abundant in plants belonging to the Lamiaceae family, has recently attracted much attention for its many biological...
Carvacrol (CAR), a natural monoterpene particularly abundant in plants belonging to the Lamiaceae family, has recently attracted much attention for its many biological properties (antioxidant, anti-inflammatory, neuroprotective, antitumour, antibacterial, and several others). However, CAR has poor chemical-physical properties (low water solubility and high volatility), which hamper its potential pharmacological uses. In this paper, the synthesis and antimicrobial evaluation of 23 carvacrol derivatives (WSCP1-23) against a panel of selected gram-positive and gram-negative bacteria are reported. Using the prodrug approach, CAR hydrophilic (WSCP1-17) and lipophilic prodrugs (WSCP18-23) were prepared. Notably, CAR water solubility was increased by using polar neutral groups (such as natural amino acids) with the aim of improving oral drug delivery. On the other hand, CAR lipophilic prodrugs, obtained by prenylation of CAR hydroxyl group, were designed to promote membrane permeation and oral absorption. Our results revealed that WSCP1-3, showing the highest water solubility (>1700-fold compared to that of CAR), possessed good antibacterial activity against gram-negative bacteria with MIC values comparable to those of CAR and antifungal properties against different species of Candida. WSCP18-19 were the most promising prodrugs, showing good antibacterial profiles against gram-positive bacteria by interfering with the biofilm formation of Staphylococcus aureus and Staphylococcus epidermidis. Moreover, WSCP18-19 resulted more stable in simulated fluids and human plasma than WSCP1-3. Toxicity studies performed on human erythrocytes and HaCaT cells revealed that all WSCPs were not toxic at the tested concentrations.
Topics: Anti-Bacterial Agents; Antifungal Agents; Candida; Cymenes; Dose-Response Relationship, Drug; Gram-Negative Bacteria; Gram-Positive Bacteria; Microbial Sensitivity Tests; Molecular Structure; Monoterpenes; Prodrugs; Solubility; Structure-Activity Relationship
PubMed: 31207463
DOI: 10.1016/j.ejmech.2019.05.093 -
Bioorganic & Medicinal Chemistry Nov 2016The antiviral activity of 4-hydroxy-hexahydro-2H-chromenes and 4-fluorine-hexahydro-2H-chromenes with an aromatic substituent, synthesized from monoterpene...
The antiviral activity of 4-hydroxy-hexahydro-2H-chromenes and 4-fluorine-hexahydro-2H-chromenes with an aromatic substituent, synthesized from monoterpene (-)-verbenone, was studied for the first time. Five of 11 (45 per cent) of 4-hydroxy-hexahydro-2H-chromene-type compounds have been found to exhibit antiviral activity against influenza A virus of subtype H1N1pdm09. Although a portion of active compounds among 4-fluorine-containing series was fewer, just compound 5i that contains a fluorine substituent exhibited more potent anti-influenza activity along with low cytotoxicity. Thus two new promising types of antiviral compounds were identified.
Topics: Antiviral Agents; Benzopyrans; Dose-Response Relationship, Drug; Humans; Influenza A virus; Microbial Sensitivity Tests; Molecular Structure; Monoterpenes; Structure-Activity Relationship
PubMed: 27591012
DOI: 10.1016/j.bmc.2016.08.037 -
Molecules (Basel, Switzerland) Dec 2020Monoterpenes are plant secondary metabolites, widely used in industrial processes as precursors of important aroma compounds, such as vanillin and (-)-menthol. However,... (Review)
Review
Monoterpenes are plant secondary metabolites, widely used in industrial processes as precursors of important aroma compounds, such as vanillin and (-)-menthol. However, the physicochemical properties of monoterpenes make difficult their conventional conversion into value-added aromas. Biocatalysis, either by using whole cells or enzymes, may overcome such drawbacks in terms of purity of the final product, ecological and economic constraints of the current catalysis processes or extraction from plant material. In particular, the ability of oxidative enzymes (e.g., oxygenases) to modify the monoterpene backbone, with high regio- and stereo-selectivity, is attractive for the production of "natural" aromas for the flavor and fragrances industries. We review the research efforts carried out in the molecular analysis of bacterial monoterpene catabolic pathways and biochemical characterization of the respective key oxidative enzymes, with particular focus on the most relevant precursors, β-pinene, limonene and β-myrcene. The presented overview of the current state of art demonstrates that the specialized enzymatic repertoires of monoterpene-catabolizing bacteria are expanding the toolbox towards the tailored and sustainable biotechnological production of values-added aroma compounds (e.g., isonovalal, α-terpineol, and carvone isomers) whose implementation must be supported by the current advances in systems biology and metabolic engineering approaches.
Topics: Acyclic Monoterpenes; Animals; Bacteria; Bicyclic Monoterpenes; Biotechnology; Humans; Limonene; Monoterpenes; Odorants
PubMed: 33379215
DOI: 10.3390/molecules26010091 -
Phytochemistry Dec 2011The glycosylation of lipophilic small molecules produces many important plant secondary metabolites. The majority of these are O-glycosides with relatively fewer... (Review)
Review
The glycosylation of lipophilic small molecules produces many important plant secondary metabolites. The majority of these are O-glycosides with relatively fewer occurring as glucose esters of aromatic or aliphatic acids. In particular, monoterpene acid glucose esters have much lower structural diversity and distribution compared to monoterpene glycosides. Nevertheless, there have been over 20 monoterpene acid glucose esters described from trees in the genus Eucalyptus (Myrtaceae) in recent years, all based on oleuropeic acid, menthiafolic acid or both. Here we review all of the glucose esters containing these monoterpenoids identified in plants to date. Many of the compounds contain phenolic aglycones and all contain at least one α,β-unsaturated carbonyl, affording a number of important potential therapeutic reactivities such as anti-tumor promotion, carcinogenesis suppression, and anti-oxidant and anti-inflammatory activities. Additional properties such as cytotoxicity, bitterness, and repellency are suggestive of a role in plant defence, but we also discuss their localization to the exterior of foliar secretory cavity lumina, and suggest they may also protect secretory cells from toxic terpenes housed within these structures. Finally we discuss how the use of a recently developed protocol to isolate secretory cavities in a functional state could be used in conjunction with systems biology approaches to help characterize their biosynthesis and roles in plants.
Topics: Cyclohexanecarboxylic Acids; Esters; Eucalyptus; Glucose; Monoterpenes; Plants
PubMed: 21945720
DOI: 10.1016/j.phytochem.2011.08.026 -
Phytopathology Jan 2015Resin obtained from Pinus radiata and five monoterpene components of resin (limonene, α-pinene, β-pinene, camphene, and myrcene) were tested to determine their effects...
Resin obtained from Pinus radiata and five monoterpene components of resin (limonene, α-pinene, β-pinene, camphene, and myrcene) were tested to determine their effects on mycelial growth and germination and survival of spores of Fusarium circinatum, the cause of pitch canker in pine, and F. temperatum, which is interfertile with F. circinatum but not pathogenic to pine. Averaged across all treatments, F. temperatum sustained the greatest reduction in radial growth (16.9±0.02% of control). The greatest reduction in dry weight also occurred in F. temperatum (11.7±0.01% of control), and all isolates of F. circinatum were significantly less affected (P<0.05). Spore germination rates in a saturated atmosphere of monoterpenes were relatively high for all tested isolates but, when placed in direct contact with resin, spore survival was significantly greater for F. circinatum than for F. temperatum. Our results are consistent with the hypothesis that greater tolerance of resin is one factor distinguishing F. circinatum from the nonpathogenic F. temperatum. However, differential tolerance of monoterpene components of resin is not sufficient to explain the observed variation in virulence to pine in F. circinatum.
Topics: Acyclic Monoterpenes; Alkenes; Bicyclic Monoterpenes; Bridged Bicyclo Compounds; Cyclohexenes; Fusarium; Limonene; Monoterpenes; Pinus; Plant Diseases; Resins, Plant; Species Specificity; Spores; Terpenes
PubMed: 25163010
DOI: 10.1094/PHYTO-02-14-0027-R