Jasmonic acid alleviates cadmium toxicity through regulating the antioxidant response and enhancing the chelation of cadmium in rice (Oryza sativa L.).

Cadmium (Cd) is a potentially hazardous element with substantial biological toxicity, adversely affecting plant growth and physiological metabolism. Therefore, it is necessary to explore practical and environment-friendly approaches to reduce toxicity. Jasmonic acid (JA) is an endogenous growth regulator which helps plants defend against biological and abiotic stresses. To determine how JA help relieve Cd toxicity in rice, both laboratory and field experiments were implemented. In the seedling stage, the role of JA in mediating rice Cd tolerance was investigated via a fluorescent probe in vivo localization, Fourier Transform Infrared Spectroscopy (FTIR), and colorimetry. At the mature growth stage of rice, field experiments were implemented to research the effects of JA on the Cd uptake and translocation in rice. In the seedling stage of rice, we found that JA application increased the cell wall compartmentalization of Cd by promoting the Cd combination on chelated-soluble pectin of rice roots and inhibited Cd movement into protoplasts, thereby reducing the Cd content in the roots by 30.5% and in the shoots by 53.3%, respectively. Application of JA reduced H2O2 content and helped relieve Cd-induced peroxidation damage of membrane lipid by increasing the level of catalase (CAT), peroxidase (POD), ascorbate peroxidase (APX), and glutathione (GSH), but had no significant effect on the superoxide dismutase (SOD) activity. Additionally, field experiments showed that foliar spraying of JA inhibited rice Cd transport from the stalk and root to the grain and reduced Cd concentration in grain by 29.7% in the high-Cd fields and 28.0% in the low-Cd fields. These results improve our understanding of how JA contributes to resistance against Cd toxicity in rice plants and reduces the accumulation of Cd in rice kernels.

Bioavailable phytoprostanes and phytofurans from Gracilaria longissima have anti-inflammatory effects in endothelial cells.

BACKGROUND: An array of bioactive compounds with health-promoting effects has been described in several species of macroalgae. Among them, phytoprostanes (PhytoPs) and phytofurans (PhytoFs), both autoxidation products of α-linolenic acid, have been seen to exert immunomodulatory and antiinflammatory activities in vitro. The purpose of this study was to explore the bioaccesibility, bioavailability, and bioactivity of PhytoPs and PhytoFs obtained from the edible red algae Gracilaria longissima, and to gain insight into the anti-inflammatory activity of their bioavailable fraction in human endothelial cells. METHODS: The PhytoPs and PhytoFs profile and concentration of G. longissima were determined by UHPLC-QqQ-MS/MS. Algal samples were processed following a standardised digestion method including gastric, intestinal, and gastrointestinal digestion. The bioavailability of the PhytoPs and PhytoFs in the characterized fractions was assessed in a Caco-2 cell monolayer model of the intestinal barrier. The inflammation response of these prostaglandin-like compounds in human endothelial cells, after intestinal absorption, was investigated in vitro. RESULTS: Simulated digestions significantly reduced the concentration of PhytoPs and PhytoFs up to 1.17 and 0.42 µg per 100 g, respectively, on average, although permeability through the Caco-2 cell monolayer was high (up to 88.2 and 97.7%, on average, respectively). PhytoP and PhytoF-enriched extracts of raw algae impaired the expression of ICAM-1 and IL-6 inflammation markers. The inflammation markers progressed in contrast to the relative concentrations of bioactive oxylipins, suggesting pro- or anti-inflammatory activity on their part. In this aspect, the cross-reactivity of these compounds with diverse receptors, and their relative concentration could explain the diversity of the effects found in the current study. CONCLUSIONS: The results indicate that PhytoPs and PhytoFs display complex pharmacological profiles probably mediated through their different actions and affinities in the endothelium.

Lipoxygenase Pathways in Diatoms: Occurrence and Correlation with Grazer Toxicity in Four Benthic Species.

Oxygenated derivatives of fatty acids, collectively called oxylipins, are a highly diverse family of lipoxygenase (LOX) products well described in planktonic diatoms. Here we report the first investigation of these molecules in four benthic diatoms, Cylindrotheca closterium, Nanofrustulum shiloi, Cocconeis scutellum, and Diploneis sp. isolated from the leaves of the seagrass Posidonia oceanica from the Gulf of Naples. Analysis by hyphenated MS techniques revealed that C. closterium, N. shiloi, and C. scutellum produce several polyunsaturated aldehydes (PUAs) and linear oxygenated fatty acids (LOFAs) related to the products of LOX pathways in planktonic species. Diploneis sp. also produced other unidentified fatty acid derivatives that are not related to LOX metabolism. The levels and composition of oxylipins in the benthic species match their negative effects on the reproductive success in the sea urchin Paracentrotus lividus. In agreement with this correlation, the most toxic species N. shiloi revealed the same LOX pathways of Skeletonema marinoi and Thalassiosira rotula, two bloom-forming planktonic diatoms that affect copepod reproduction. Overall, our data highlight for the first time a major role of oxylipins, namely LOFAs, as info-chemicals for benthic diatoms, and open new perspectives in the study of the structuring of benthic communities.

Foliage inoculation by Burkholderia vietnamiensis CBMB40 antagonizes methyl jasmonate-mediated stress in Eucalyptus grandis.

Methyl jasmonate (MeJA) is widely used as a model chemical to study hypersensitive responses to biotic stress impacts in plants. Elevated levels of methyl jasmonate induce jasmonate-dependent defense responses, associated with a decline in primary metabolism and enhancement of secondary metabolism of plants. However, there is no information of how stress resistance of plants, and accordingly the sensitivity to exogenous MeJA can be decreased by endophytic plant growth promoting rhizobacteria (PGPR) harboring ACC (1-aminocyclopropane-1-carboxylate) deaminase. In this study, we estimated stress alleviating potential of endophytic PGPR against MeJA-induced plant perturbations through assessing photosynthetic traits and stress volatile emissions. We used mild (5 mM) to severe (20 mM) MeJA and endophytic plant growth promoting rhizobacteria Burkholderia vietnamiensis CBMB40 and studied how MeJA and B. vietnamiensis treatments influenced temporal changes in photosynthetic characteristics and stress volatile emissions. Separate application of MeJA markedly decreased photosynthetic characteristics and increased lipoxygenase pathway (LOX) volatiles, volatile isoprenoids, saturated aldehydes, lightweight oxygenated compounds (LOC), geranyl-geranyl diphosphate pathway (GGDP) volatiles, and benzenoids. However, MeJA-treated leaves inoculated by endophytic bacteria B. vietnamiensis had substantially increased photosynthetic characteristics and decreased emissions of LOX, volatile isoprenoids and other stress volatiles compared with non-inoculated MeJA treatments, especially at later stages of recovery. In addition, analysis of leaf terpenoid contents demonstrated that several mono- and sesquiterpenes were de novo synthesized upon MeJA and B. vietnamiensis applications. This study demonstrates that foliar application of endophytic bacteria B. vietnamiensis can potentially enhance resistance to biotic stresses and contribute to the maintenance of the integrity of plant metabolic activity.

Molecular and Morphological Toxicity of Diatom-Derived Hydroxyacid Mixtures to Sea Urchin Paracentrotus lividus Embryos.

Oxylipins such as polyunsaturated aldehydes (PUAs) and hydroxyacids (HEPEs) are signaling molecules derived from the oxidation of polyunsaturated fatty acids. They are common in diatoms that constitute a major group of microalgae in freshwater and oceanic ecosystems. Although HEPEs represent the most common oxylipins produced by diatoms, little information is available on their effects on marine invertebrates, and most of the information has been obtained by testing individual HEPEs. Our previous studies reported that four hydroxyacids, i.e., 5-, 9-, 11-, and 15-HEPE, were able to induce malformations and a marked developmental delay in sea urchin Paracentrotus lividus embryos, which had not been reported for other oxylipins. Here, we tested a mixture of 5-, 9-, 11-, and 15-HEPE at different concentrations for the first time. The results showed that mixtures of HEPEs have synergistic effects that are much more severe compared to those of individual HEPEs: The HEPE mixtures induced malformations in sea urchin embryos at lower concentrations. Increasing HEPE mixture concentrations induced a marked increase in the number of delayed embryos, until all embryos were delayed at the highest concentration tested. At the molecular level, the HEPE mixtures induced variations in the expression of 50 genes involved in different functional processes, mainly down-regulating these genes at the earliest stages of embryonic development. These findings are ecologically significant, considering that during diatom blooms, sea urchins could accumulate HEPEs in concentrations comparable to those tested in the present study.

Jasmonic acid induced changes in physio-biochemical attributes and ascorbate-glutathione pathway in Lycopersicon esculentum under lead stress at different growth stages.

Lead (Pb) is one of most toxic heavy metals that adversely affect growth and developmental in plants. It becomes necessary to explore environment safe strategies to ameliorate its toxic effects. Phytohormones play an imperative role in regulating stress protection in plants. Jasmonic acid (JA) is recognized as a potential phytohormone which mediates immune and growth responses to enhance plant survival under stressful environment. The present study was undertaken to evaluate the effect of JA on the growth, metal uptake, gaseous exchange parameters, and on the contents of pigments, osmolytes, and metal chelating compounds in tomato plants under Pb stress during different stages of growth (in 30-, 45-, and 60-day-old plants). We observed a decrease in shoot and root lengths under Pb stress. Treatment of JA improved the shoot and root lengths in the Pb-treated plants. The Pb uptake was increased with the increasing concentrations of Pb, however, seeds pretreated with JA reduced the Pb uptake by the plants. The chlorophyll and carotenoid contents increased by JA treatment in plants under Pb stress. Pre-soaking of seeds in JA, improved gaseous exchange parameters, such as internal CO2 concentration, net photosynthetic rate, stomatal conductance, and transpiration rate under Pb stress. JA enhanced the enzyme activity of ascorbate-glutathione cycle and reduced H2O2 concentration in Pb-treated plants. The contents of osmolyte and metal chelating compounds (total thiols, and non-protein and protein-bound thiols) were increased with the increase in Pb stress. In seeds primed with JA, the contents of osmolytes and metal chelating compounds were further increased in the Pb-treated plants. Our results suggested that treatment of JA ameliorated the toxic effects of Pb stress by reducing the Pb uptake and improving the growth, photosynthetic attributes, activity of ascorbate-glutathione cycle and increasing the contents of osmolytes and metal chelating compounds in the tomato plants.

Production of toxic metabolites by two strains of Lasiodiplodia theobromae, isolated from a coconut tree and a human patient.

Lasiodiplodia theobromae is a phytopathogenic fungus that causes diseases not only in a broad number of plant hosts but also occasionally in humans. The capacity of L. theobromae to produce bioactive metabolites at 25 C (environmental mean temperature) and at 37 C (body mean temperature) was investigated. Two strains, CAA019 and CBS339.90, isolated respectively from a coconut tree and a human patient were characterized. The phytotoxicity and cytotoxicity (on mammalian cells) of the secretomes of both strains of L. theobromae were investigated. Also, phytotoxicity and cytotoxicity of pure compounds were evaluated. The phytotoxicity of the secretome of strain CAA019 was higher than the phytotoxicity of the secretome of strain CBS339.90 at 25 C. However, the phytotoxicity for both strains decreased when they were grown at 37 C. Only the secretome of strain CBS339.90 grown at 37 C induced up to 90% Vero and 3T3 cell mortality. This supports the presence of different metabolites in the secretome of strains CAA019 and CBS339.90. Metabolites typical of L. theobromae were isolated and identified from organic extracts of the secretome of both strains (e.g., 3-indolecarboxylic acid, jasmonic acid, lasiodiplodin, four substituted 2-dihydrofuranones, two melleins, and cyclo-(Trp-Ala)). Also, metabolites such as scytalone, not previously reported for this species, were isolated and identified. Metabolite production is affected by strain and temperature. In fact, some metabolites are strain specific (e.g., lasiodiplodin) and some metabolites are temperature specific (e.g., jasmonic acid). Although more strains should be characterized, it may be anticipated that temperature tuning of secondary-metabolite production emerges as a putative contributing factor in the modulation of L. theobromae pathogenicity towards plants, and also towards mammalian cells.

Cyclooxygenases and lipoxygenases are used by the fungus Podospora anserina to repel nematodes.

Oxylipins are secondary messengers used universally in the living world for communication and defense. The paradigm is that they are produced enzymatically for the eicosanoids and non-enzymatically for the isoprostanoids. They are supposed to be degraded into volatile organic compounds (VOCs) and to participate in aroma production. Some such chemicals composed of eight carbons are also envisoned as alternatives to fossil fuels. In fungi, oxylipins have been mostly studied in Aspergilli and shown to be involved in signalling asexual versus sexual development, mycotoxin production and interaction with the host for pathogenic species. Through targeted gene deletions of genes encoding oxylipin-producing enzymes and chemical analysis of oxylipins and volatile organic compounds, we show that in the distantly-related ascomycete Podospora anserina, isoprostanoids are likely produced enzymatically. We show the disappearance in the mutants lacking lipoxygenases and cyclooxygenases of the production of 10-hydroxy-octadecadienoic acid and that of 1-octen-3-ol, a common volatile compound. Importantly, this was correlated with the inability of the mutants to repel nematodes as efficiently as the wild type. Overall, our data show that in this fungus, oxylipins are not involved in signalling development but may rather be used directly or as precursors in the production of odors against potential agressors. SIGNIFICANCE: We analyzse the role in inter-kingdom communication of lipoxygenase (lox) and cyclooxygenase (cox) genes in the model fungus Podospora anserina. Through chemical analysis we define the oxylipins and volatile organic compounds (VOCs)produce by wild type and mutants for cox and lox genes, We show that the COX and LOX genes are required for the production of some eight carbon VOCs. We show that COX and LOX genes are involved in the production of chemicals repelling nematodes. This role is very different from the ones previously evidenced in other fungi.

Lipoxygenases and Lipoxygenase Products in Marine Diatoms.

Marine diatoms negatively affect reproduction and later larval development of dominant zooplankton grazers such as copepods, thereby lowering the recruitment of the next generations of these small crustaceans that are a major food source for larval fish species. The phenomenon has been explained in terms of chemical defense due to grazer-induced synthesis of oxylipins, lipoxygenase-derived oxygenated fatty acid derivatives. Since this first report, studies about diatom oxylipins have multiplied and broadened toward other aspects concerning bloom dynamics, cell growth, and cell differentiation. Diatom oxylipins embrace a number of diverse structures that are recognized as chemical signals in ecological and physiological processes in many other organisms. In diatoms, the most studied examples include polyunsaturated aldehydes (PUAs) and nonvolatile oxylipins (NVOs). The purpose of this chapter is to provide the analytical tools to deal with identification, analysis and biosynthesis of these compounds. Emphasis is given to identification of the enzymatic steps and characterization of the species-specific lipoxygenases even in absence of the availability of molecular information.

Toxigenic effects of two benthic diatoms upon grazing activity of the sea urchin: morphological, metabolomic and de novo transcriptomic analysis.

Diatoms are unicellular algae playing a key role as photosynthetic organisms in the world's ocean food webs. The chemical ecology of planktonic diatoms is well documented, but few studies have reported on the effects of benthic diatoms on their consumers, also due to difficulties in the collection, quantification and massive culturing of benthic species. Here for the first time we investigate the effects of feeding on two abundantly occurring benthic diatoms, Nanofrustulum shiloi and Cylindrotheca closterium, isolated from the leaves of the seagrass Posidonia oceanica, on the sea urchin Paracentrotus lividus. Adult P. lividus were fed for one month on diets of either one of the two diatoms and on the green alga Ulva rigida, used as a feeding control. By combining morphological, metabolomic and de novo transcriptomic approaches, we demonstrate toxigenic effect on embryos generated by females fed with these benthic diatoms. Furthermore, chemical analysis reveal the presence of polyunsaturated aldehydes only for N. shiloi, and a high production of other oxylipins (cytotoxic compounds on their grazers and on cancer cell lines) for both diatoms, including some additional peaks not correlated to the canonic oxylipins commonly observed in planktonic diatoms. These findings open new perspectives in the study of diatom secondary metabolites influencing their grazers.

Critical Role of COI1-Dependent Jasmonate Pathway in AAL toxin induced PCD in Tomato Revealed by Comparative Proteomics.

Alternaria alternata f.sp. Lycopersici (AAL) toxin induces programmed cell death (PCD) in susceptible tomato (Solanum lycopersicum) leaves. Jasmonate (JA) promotes AAL toxin induced PCD in a COI1 (coronatine insensitive 1, JA receptor)-dependent manner by enhancement of reactive oxygen species (ROS) production. To further elucidate the underlying mechanisms of this process, we performed a comparative proteomic analysis using tomato jasmonic acid insensitive1 ( jai1), the receptor mutant of JA, and its wild type (WT) after AAL toxin treatment with or without JA treatment. A total of 10367 proteins were identified in tomato leaves using isobaric tags for relative and absolute quantitation (iTRAQ) quantitative proteomics approach. 2670 proteins were determined to be differentially expressed in response to AAL toxin and JA. Comparison between AAL toxin treated jai1 and its WT revealed the COI1-dependent JA pathway regulated proteins, including pathways related to redox response, ceramide synthesis, JA, ethylene (ET), salicylic acid (SA) and abscisic acid (ABA) signaling. Autophagy, PCD and DNA damage related proteins were also identified. Our data suggest that COI1-dependent JA pathway enhances AAL toxin induced PCD through regulating the redox status of the leaves, other phytohormone pathways and/or important PCD components.

Diatom-derived oxylipins induce cell death in sea urchin embryos activating caspase-8 and caspase 3/7.

Diatoms are an important class of unicellular algae that produce bioactive secondary metabolites with cytotoxic activity collectively termed oxylipins, including polyunsaturated aldehydes (PUAs), hydroxyacids (HEPEs), oxo-acids and epoxyalcohols. Previous results showed that at higher concentrations, the PUA decadienal induced apoptosis on copepods and sea urchin embryos via caspase-3 activation; at lower concentrations decadienal affected the expression levels of the caspase-8 gene in embryos of the sea urchin Paracentrotus lividus. In the present work, we studied the effects of other common oxylipins produced by diatoms: two PUAs (heptadienal and octadienal) and four hydroxyacids (5-, 9- 11- and 15-HEPE) on P. lividus cell death and caspase activities. Our results showed that (i) at higher concentrations PUAs and HEPEs induced apoptosis in sea urchin embryos, detected by microscopic observation and through the activation of caspase-3/7 and caspase-8 measured by luminescent assays; (ii) at low concentrations, PUAs and HEPEs affected the expression levels of caspase-8 and caspase-3/7 (isolated for the first time here in P. lividus) genes, detected by Real Time qPCR. These findings have interesting implications from the ecological point of view, given the importance of diatom blooms in nutrient-rich aquatic environments.

Impacts of biotic and abiotic stress on major quality attributing metabolites of coffee beans.

Biotic stress factors such as Rhizopus oligosporus and Aspergillus niger mycelial extracts and abiotic elements methyljasmonate (MJ) and salicylic acid (SA), when administered through floral spray to Coffea canephora, showed significant influence on major bioactive metabolites of beans. Up to 42% caffeine, 39% theobromine and 46% trigonelline, along with 32% cafestol and kahweol content elevation was evident under respective elicitor treatments. Over all, the surge in respective metabolites depends on elicitor stress type and concentration. Abiotic factors MJ and SA were found to be efficient at 1 to 5 microM concentration in augmenting all the metabolites, compared to R. oligosporus and A. niger spray at 0.5-2.0% wherein the response was moderate as compared to abiotic stress, however significant compared to control. Though this elevation in caffeine, theobromine, cafestol and kahweol is not warranted from quality point of view, increase in trigonelline improves coffee quality. Besides increase in metabolites, stress mediated augmentation of bioactive compounds in coffee has a wide scope for studying gene expression pattern.

Host plant-specific remodeling of midgut physiology in the generalist insect herbivore Trichoplusia ni.

Species diversity in terrestrial ecosystems is influenced by plant defense compounds that alter the behavior, physiology, and host preference of insect herbivores. Although it is established that insects evolved the ability to detoxify specific allelochemicals, the mechanisms by which polyphagous insects cope with toxic compounds in diverse host plants are not well understood. Here, we used defended and non-defended plant genotypes to study how variation in chemical defense affects midgut responses of the lepidopteran herbivore Trichoplusia ni, which is a pest of a wide variety of native and cultivated plants. The genome-wide midgut transcriptional response of T. ni larvae to glucosinolate-based defenses in the crucifer Arabidopsis thaliana was characterized by strong induction of genes encoding Phase I and II detoxification enzymes. In contrast, the response of T. ni to proteinase inhibitors and other jasmonate-regulated defenses in tomato (Solanum lycopersicum) was dominated by changes in the expression of digestive enzymes and, strikingly, concomitant repression of transcripts encoding detoxification enzymes. Unbiased proteomic analyses of T. ni feces demonstrated that tomato defenses remodel the complement of T.ni digestive enzymes, which was associated with increased amounts of serine proteases and decreased lipase protein abundance upon encountering tomato defense chemistry. These collective results indicate that T. ni adjusts its gut physiology to the presence of host plant-specific chemical defenses, and further suggest that plants may exploit this digestive flexibility as a defensive strategy to suppress the production of enzymes that detoxify allelochemicals.

High mutagenic activity of juice from pak choi (Brassica rapa ssp. chinensis) sprouts due to its content of 1-methoxy-3-indolylmethyl glucosinolate, and its enhancement by elicitation with methyl jasmonate.

Cruciferous vegetables have the reputation to protect against cancer, an effect attributed to glucosinolates (GLS) and their breakdown products. However, some GLS are mutagenic, an activity associated with cancer initiation rather than chemoprevention. We show that juices from steamed pak choi sprouts are strongly mutagenic in Salmonella typhimurium TA100 upon addition of fresh myrosinase. Growth of the plants in the presence of methyl jasmonate, a hormone eliciting defence factors, led to 20-fold enhanced mutagenic activity. The level of 1-methoxy-3-indolylmethyl (1-MIM)-GLS was similarly increased, whereas those of other GLS were only elevated 0.8- to 3.2-fold. 1-MIM-GLS is a potent mutagen, whose activity is further enhanced by human sulphotransferase 1A1 (hSULT1A1), an activation not observed with other GLS. The mutagenicity of the pak choi juices was increased 20-fold in bacteria expressing hSULT1A1. A tiny level of juice from elicitated sprouts, 0.04% in the mutagenicity assay, was sufficient to double the number of revertants above the spontaneous level. We conclude that pak choi juice is mutagenic, an activity that can be strongly affected by the growth conditions. It is owed essentially to a single component, 1-MIM-GLS. We recommend using cultivars, growth conditions and/or food preparations that keep the level of this GLS congener low.

Deuterium labeling for investigating de novo synthesis of terpene volatiles in Achyranthes bidentata.

PURPOSE OF WORK: Plants synthesize and accumulate secondary metabolites as defensive volatiles against diverse stresses. We aim to unravel the jasmonate-inducible volatile de novo synthetic metabolites in plants using a deuterium-labeling technique. Jasmonic acid and its methyl ester (MeJA) are well-documented for inducing defensive volatiles. Here, we have developed an efficient deuterium oxide (D2O)-based labeling approach to determine the extent of de novo synthetic metabolites in a model plant A. bidentata bidentata. The labeling approach was demonstrated on quantitative profiling of terpene volatile organic compounds (VOCs) elicited by airborne MeJA in Achyranthes plants. We show, for the first time that airborne MeJA-elicited terpene VOCs are predominantly and differentially de novo synthesized except for a homoterpene, (3E)-4,8-dimethyl-1,3,7-nonatriene, which is weakly and least labelled with deuterium. D2O is therefore an efficient labeling source for investigating de novo synthetic metabolites of terpene VOCs in planta.

Fragrance material review on methyl dihydrojasmonate.

A toxicologic and dermatologic review of methyl dihydrojasmonate when used as a fragrance ingredient is presented. Methyl dihydrojasmonate is a member of the fragrance structural group ketones cyclopentanones and cyclopentenones. The common characteristic structural element of the group members is a cyclopentanone or cyclopentenone ring with a straight or branched chain alkane or alkene substituent. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for methyl dihydrojasmonate were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, elicitation, phototoxicity, photoallergy, toxicokinetics, repeated dose, reproductive toxicity, and genotoxicity data. A safety assessment of the entire ketones cyclopentanones and cyclopentenones will be published simultaneously with this document; please refer to Belsito et al. (this issue) for an overall assessment of the safe use of this material.

Fragrance material review on methyl jasmonate.

A toxicologic and dermatologic review of methyl jasmonate when used as a fragrance ingredient is presented. Methyl jasmonate is a member of the fragrance structural group Ketones Cyclopentanones and Cyclopentenones. The common characteristic structural element of the group members is a cyclopentanone or cyclopentenone ring with a straight or branched chain alkane or alkene substituent. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for methyl jasmonate were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, phototoxicity, and photoallergy data. A safety assessment of the entire Ketones Cyclopentanones and Cyclopentenones will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all Ketones Cyclopentanones and Cyclopentenones in fragrances.

Fragrance material review on cis-jasmone.

A toxicologic and dermatologic review of cis-jasmone when used as a fragrance ingredient is presented. cis-Jasmone is a member of the fragrance structural group ketones cyclopentanones and cyclopentenones. The common characteristic structural element of the group members is a cyclopentanone or cyclopentenone ring with a straight or branched chain alkane or alkene substituent. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for cis-jasmone were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, mucous membrane (eye) irritation, skin sensitization, phototoxicity, photoallergy, and genotoxicity data. A safety assessment of the entire ketones cyclopentanones and cyclopentenones will be published simultaneously with this document; please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all ketones cyclopentanones and cyclopentenones in fragrances.