3,5-Dimethoxytoluene

Aromatic profile of black truffle grown in Argentina: Characterization of commercial categories and alterations associated to maturation, harvesting date and orchard management practices.[Pubmed:37803611]

Food Res Int. 2023 Nov;173(Pt 1):113300.

Black truffle (Tuber melanosporum) is one of the most appreciated fungi in the world mainly due to its aromatic properties. In the emerging markets such as Argentina, the aroma of locally produced truffles has not been described yet. The volatile organic compounds (VOCs) from 102 black truffles from Argentina were analyzed using solid phase microextraction gas chromatography coupled with mass spectrometer detector (SPME-GC-MS). Several factors such as commercial category, maturity stage, host tree, geographical origin, and aromatic defects detected during classification were also registered and considered. As a result, 79 VOCs were detected, among which 2-methyl-propanal, 2-butanone, 2-methyl-1-propanol, butanal-3-methyl, 3-methyl-1-butanol, 2-methyl-1-butanol were present in high percentage in fresh mature truffles, whereas immature truffles were associated with 3,5-Dimethoxytoluene, 2-phenyl-2-butenal, 2,3-dimethoxytoluene. The Argentine black truffles showed significant similarities in their aromatic profile when compared with their Australian and European counterparts, but with some distinctive notes.

Effect of molecular distillation on the anti-inflammatory activity and neurotoxicity of Asarum essential oil.[Pubmed:37284321]

Front Pharmacol. 2023 May 22;14:1196137.

Asarum essential oil (AEO) has been shown to have good pharmacological activities for the anti-inflammatory and analgesic effects, but increasing the dose may cause toxicity. Therefore, we studied the toxic and pharmacodynamic components of AEO by molecular distillation (MD). Anti-inflammatory activity was assessed using RAW264.7 cells. Neurotoxicity was assessed in PC12 cells and the overall toxicity of AEO was evaluated in the mouse acute toxicity assay. The results showed that AEO is primarily composed of safrole, methyl eugenol, and 3,5-Dimethoxytoluene. After MD, three fractions were obtained and contained different proportions of volatile compounds relative to the original oil. The heavy fraction had high concentrations of safrole and methyl eugenol, while the light fraction contained high concentrations of alpha-pinene and beta- pinene. The original oil and all three fractions exhibited anti-inflammatory effects, but the light fraction demonstrated more excellent anti-inflammatory activity than the other fractions. Asarum virgin oil and MD products are all neurotoxic. The exposure of PC12 cells to high concentrations of AEO resulted in abnormal nuclei, an increased number of apoptotic cells, increased ROS formation, and decreased SOD levels. Moreover, the results of acute toxicity tests in mice revealed that the light fractions were less toxic than virgin oils and other fractions. In summary, the data suggest that the MD technology enables the enrichment and separation of essential oil components and contributes to the selection of safe concentrations of AEO.

Characterization of volatiles in flowers from four Rosa chinensis cultivars by HS-SPME-GC x GC-QTOFMS.[Pubmed:37251764]

Front Plant Sci. 2023 May 8;14:1060747.

Rosa chinensis cultivars with volatile aromas are important resources in the perfume industry. The four rose cultivars introduced to Guizhou province are rich in volatile substances. In this study, volatiles from four Rosa chinensis cultivars were extracted using headspace-solid phase microextraction (HS-SPME), and analyzed with two-dimensional gas chromatography quadrupole time of flight mass spectrometry (GC x GC-QTOFMS). A total of 122 volatiles were identified; the main compounds in these samples were benzyl alcohol, phenylethyl alcohol, citronellol, beta-myrcene and limonene. A total of 68, 78, 71, and 56 volatile compounds were identified in Rosa 'Blue River' (RBR), Rosa 'Crimson Glory' (RCG), Rosa 'Pink Panther' (RPP), and Rosa 'Funkuhr' (RF) samples, respectively. The total volatile contents were in the following order: RBR > RCG > RPP > RF. Four cultivars exhibited similar volatility profiles, with alcohols, alkanes, and esters as the major chemical groups, followed by aldehydes, aromatic hydrocarbons, ketones, benzene, and other compounds. Alcohols and aldehydes were quantitatively the two most abundant chemical groups that included the highest number and highest content of compounds. Different cultivars have different aromas, and RCG had high contents of phenyl acetate, rose oxide, trans-rose oxide, phenylethyl alcohol and 1,3,5-trimethoxybenzene, characterized by floral and rose descriptors. RBR contained a high content of phenylethyl alcohol, and RF contained a high content of 3,5-Dimethoxytoluene. Hierarchical cluster analysis (HCA) of all volatiles showed that the three cultivars (RCG, RPP, and RF) had similar volatile characteristics and were significantly different from RBR. Differential metabolites among cultivars were screened based on the OPLS-DA model, and there were six main enriched pathways of differential metabolites: biosynthesis of secondary metabolites, monoterpenoid biosynthesis, metabolic pathways, limonene and pinene degradation, sesquiterpenoid and triterpenoid biosynthesis, and alpha-linolenic acid metabolism. The biosynthesis of secondary metabolites is the most differential metabolic pathway.

alpha-Glucosidase, alpha-Amylase and Antioxidant Evaluations of Isolated Bioactives from Wild Strawberry.[Pubmed:35684382]

Molecules. 2022 May 26;27(11):3444.

Diabetes mellitus is a metabolic disorder and is a global challenge to the current medicinal chemists and pharmacologists. This research has been designed to isolate and evaluate antidiabetic bioactives from Fragaria indica. The crude extracts, semi-purified and pure bioactives have been used in all in vitro assays. The in vitro alpha-glucosidase, alpha-amylase and DPPH free radical activities have been performed on all plant samples. The initial activities showed that ethyl acetate (Fi.EtAc) was the potent fraction in all the assays. This fraction was initially semi-purified to obtain Fi.EtAc 1-3. Among the semi-purified fractions, Fi.EtAc 2 was dominant, exhibiting potent IC(50) values in all the in vitro assays. Based on the potency and availability of materials, Fi.EtAc 2 was subjected to further purification to obtain compounds 1 (2,4-dichloro-6-hydroxy-3,5-Dimethoxytoluene) and 2 (2-methyl-6-(4-methylphenyl)-2-hepten-4-one). The two isolated compounds were characterized by mass and NMR analyses. The compounds 1 and 2 showed excellent inhibitions against alpha-glucosidase (21.45 for 1 and 15.03 for 2 mug/mL), alpha-amylase (17.65 and 16.56 mug/mL) and DPPH free radicals (7.62 and 14.30 mug/mL). Our study provides baseline research for the antidiabetic bioactives exploration from Fragaria indica. The bioactive compounds can be evaluated in animals-based antidiabetic activity in future.

Fumigant Toxicity and Oviposition Deterrent Activity of Volatile Constituents from Asari Radix et Rhizoma against Phthorimaea operculella (Lepidoptera: Gelechiidae).[Pubmed:33306098]

J Insect Sci. 2020 Nov 1;20(6):32.

Phthorimaea operculella (Zeller) is a worldwide pest of potato. Plant-borne chemicals would be potential alternatives of synthetic chemical fumigants against P. operculella in the storage. Asari Radix et Rhizoma is derived from the dry roots and rhizomes of Asarum heterotropoides Fr. Schmidt var. mandshuricum, A. sieboldii Miq. var. seoulense, or A. sieboldii. In this study, fumigant toxicity and oviposition deterrent of volatile constituents from ARR, delta-3-carene, gamma-terpinene, terpinolene, eucarvone, 3,5-Dimethoxytoluene, and methyleugenol were tested against P. operculella. The preliminary verification of preventive and control effects of eucarvone, 3,5-Dimethoxytoluene and methyleugenol on P. operculella was carried out by simulating warehouse experiments. The results indicated that the six compounds above had fumigation toxic effects on the adults and eggs of P. operculella. Among them, delta-3-carene, gamma-terpinene, and terpinolene had weaker fumigation effects than those of eucarvone, 3,5-Dimethoxytoluene, and methyleugenol. The LC50 values of eucarvone, 3,5-Dimethoxytoluene, and methyleugenol against adult P. operculella were 1.01, 1.78, 1.51 mg/liter air, respectively. The LC50 values against egg P. operculella were 1.09, 0.55, 0.30 mg/liter air, respectively. The oviposition deterrent experiment showed that only methyleugenol (at 5 and 1 mg/ml) and eucarvone (5 mg/ml) had a substantial oviposition deterrent effect. The simulated warehouse experiment verified that methyleugenol, eucarvone, and 3,5-Dimethoxytoluene protected potatoes from P. operculella and demonstrated that methyleugenol had the best preventive and control effects. It was concluded that methyleugenol was the active ingredient with the most potential in the volatiles from ARR on P. operculella control and merit further study as botanic fumigant.

The Relative Content and Distribution of Absorbed Volatile Organic Compounds in Rats Administered Asari Radix et Rhizoma Are Different between Powder- and Decoction-Treated Groups.[Pubmed:32992581]

Molecules. 2020 Sep 27;25(19):4441.

Asari Radix et Rhizoma (ARR) is an important traditional Chinese medicine. Volatile organic compounds (VOCs) are the main active constituents of ARR. Research on the metabolite profile of VOCs and the difference of absorbed constituents in vivo after an administration of ARR decoction and powder will be helpful to understand the pharmacological activity and safety of ARR. In this study, headspace solid-phase microextraction gas chromatography mass spectrometry (HS-SPME-GC-MS) was applied to profile the VOCs from ARR in rats in vivo. A total of 153 VOCs were tentatively identified; 101 were original constituents of ARR (98 in the powder-treated group and 43 in the decoction-treated group) and 15 were metabolites, and their metabolic reactions were mainly oxidation and reduction, with only two cases of methylation and esterification, and 37 unclassified compounds were identified only in the ARR-treated group. Of the 153 VOCs identified, 131 were reported in rats after oral administration of ARR for the first time, containing 79 original constituents, 15 metabolites, and 37 unclassified compounds. In the powder-treated group, methyleugenol, safrole, 3,5-Dimethoxytoluene (3,5-DMT), 2,3,5-trimethoxytoluene (2,3,5-TMT), and 3,4,5-trimethoxytoluene (3,4,5-TMT) were the main absorbed constituents, the relative contents of which were significantly higher compared to the decoction-treated group, especially methyleugenol, safrole, and 3,5-DMT. In the decoction-treated group, 3,4,5-TMT, 2,3,5-TMT, kakuol, and eugenol were the main constituents with a higher content and wider distribution. The results of this study provide a reference for evaluating the efficacy and safety of ARR.

Total Synthesis of (-)-Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p-Quinone.[Pubmed:31608523]

Angew Chem Int Ed Engl. 2019 Dec 2;58(49):17552-17557.

The first copper-catalyzed intermolecular [5+2] homodimerization of hydroxy p-quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine-step total synthesis of (-)-perezoperezone from commercially available 3,5-Dimethoxytoluene.

Characterization of Volatile Compounds in Four Different Rhododendron Flowers by GCxGC-QTOFMS.[Pubmed:31547401]

Molecules. 2019 Sep 12;24(18):3327.

Volatile compounds in flowers of Rhododendron delavayi, R. agastum, R. annae, and R. irroratum were analyzed using comprehensive two-dimensional gas chromatography-mass spectrometry (GCxGC) coupled with high-resolution quadrupole time-of-flight mass spectrometry (QTOFMS). A significantly increased number of compounds was separated by GCxGC compared to conventional one-dimensional GC (1DGC), allowing more comprehensive understanding of the volatile composition of Rhododendron flowers. In total, 129 volatile compounds were detected and quantified. Among them, hexanal, limonene, benzeneacetaldehyde, 2-nonen-1-ol, phenylethyl alcohol, citronellal, isopulegol, 3,5-Dimethoxytoluene, and pyridine are the main compounds with different content levels in all flower samples. 1,2,3-trimethoxy-5-methyl-benzene exhibits significantly higher content in R. irroratum compared to in the other three species, while isopulegol is only found in R. irroratum and R. agastum.

Orthogonal test design for optimization of the extraction of essential oil from Asarum heterotropoides var. Mandshuricum and evaluation of its antibacterial activity against periodontal pathogens.[Pubmed:30456007]

3 Biotech. 2018 Nov;8(11):473.

The optimum extraction conditions of essential oil from Asarum heterotropoides var. Mandshuricum applied by an orthogonal L(9)(3(3)) test were a water-to-raw material ratio of 17, a particle size of D (95) 3,5-Dimethoxytoluene (10.30%) orderly. In vitro, the minimum inhibitory concentration and minimum bactericidal concentration of essential oil were 0.01 and 0.02% against F. nucleatum, 0.04 and 0.08% against P. intermedia, and 0.005 and 0.005% against P. gingivalis. In vivo, administration of essential oil significantly suppressed alveolar bone resorption induced by F. nucleatum, with bone levels remaining comparable to non-infected mice. These results of antibacterial activity of essential oil in vitro and in vivo show the inhibition of periodontal pathogens and therapy of alveolar bone resorption in mice, suggesting that its essential oil could be a potential natural therapeutic agent for treatment of periodontitis in human beings.

Laboratory and field investigation on the orientation of Frankliniella occidentalis (Thysanoptera: Thripidae) to more suitable host plants driven by volatiles and component analysis of volatiles.[Pubmed:30255657]

Pest Manag Sci. 2019 Mar;75(3):598-606.

BACKGROUND: Differences in population densities of Frankliniella occidentalis among different plant species suggest a preference for particular hosts. Host plant volatiles are often involved in insect fitness. However, few studies have explored the interaction between flower volatiles and fitness. The host fitness of F. occidentalis for different flowers was assessed through field investigation, and the olfactory preference of thrips for flower volatiles was tested in the laboratory. RESULTS: In the field study, 18 flower host plants were classified at four fitness levels by F. occidentalis. Olfactory tests showed that female F. occidentalis had significantly different preferences for different plant odours among the volatiles of the four tested flowers (each representing the four fitness levels), whereas male F. occidentalis did not. The relative response of F. occidentalis females to flower volatiles (Rosa rugosa > Dianthus caryophyllus > Gerbera jamesonii > Pelargonium hortorum) was consistent with the field performance of F. occidentalis. In total, 23, 29, 16 and 26 components were identified in the volatile profiles of R. rugosa, D. caryophyllus, G. jamesonii and P. hortorum, respectively. 3,5-Dimethoxytoluene (24.94%), nonanal (30.42%), (E)-3-penten-2-one (52.31%) and zingiberene (29.88%) were the single most abundant components of the volatiles of R. rugosa, D. caryophyllus, G. jamesonii and P. hortorum, respectively. CONCLUSION: Volatiles are important in attracting F. occidentalis to suitable hosts, and differences in the types and concentrations of volatile components among flowers may directly influence the olfactory responses and field performance of thrips. Potential attractants could be developed for integrated pest management programmes against this pest. (c) 2018 Society of Chemical Industry.

Toxic and Repellent Effects of Volatile Phenylpropenes from Asarum heterotropoides on Lasioderma serricorne and Liposcelis bostrychophila.[Pubmed:30149520]

Molecules. 2018 Aug 24;23(9):2131.

Toxic and repellent effects of the essential oil from Asarum heterotropoides Fr. Schmidt var. mandshuricum (Maxim.) Kitag. were evaluated against Lasioderma serricorne and Liposcelis bostrychophila. The essential oils (EOs) from roots (ER) and leaves (EL) of A. heterotropoides were obtained separately by hydrodistillation and characterized by gas chromatography-mass spectrometry (GC-MS) analysis. Major components of ER and EL included methyleugenol, safrole, and 3,5-Dimethoxytoluene. Both ER and EL of A. heterotropoides showed certain toxicity and repellency against L. serricorne and L. bostrychophila. 3,5-Dimethoxytoluene, methyleugenol, and safrole were strongly toxic via fumigation to L. serricorne (LC(50) = 4.99, 10.82, and 18.93 mg/L air, respectively). Safrole and 3,5-Dimethoxytoluene possessed significant fumigant toxicity against L. bostrychophila (LC(50) = 0.83 and 0.91 mg/L air, respectively). The three compounds all exhibited potent contact toxicity against the two insect species. Here, the EL of A. heterotropoides was confirmed to have certain toxicity and repellency against stored product insects, providing a novel idea for the comprehensive use of plant resources.

[Quantitative determination of seven major absorbed volatile constituents in mice brain, liver and blood after intragastric administration of Asari Radix et Rhizoma suspension by headspace-solid phase microextraction-gas chromatography-mass spectrometry].[Pubmed:28861975]

Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(2):285-293.

A headspace-solid phase microextraction-gas chromatography-mass spectrometry method（HS-SPME-GC-MS） was adopted for the quantitative study of 4-allylanisole, methyl eugenol, 2,3,5-trimethoxytoluene, 3,4,5-trimethoxytoluene, sarisan, 3,5-Dimethoxytoluene and safrole in mice brain, liver tissues and blood after intragastric administration of Asari Radix et Rhizoma. A VF-WAXms (30 mx0.25 mm, 0.25 mum film thickness) capillary column and SPME fiber coated with 65 mum polydimethylsiloxane/divinylbenzene (PDMS/DVB) were used. The calibration curves of seven volatile constituents were established to validate the method's stability (RSD<15%), repeatability (RSD<9.5%), accuracy (RSD<22%), relative recovery (87.0%-108%) and extraction recovery (74.9%-102%). The validated HS-SPME-GC-MS assay was applied to determine the concentrations of seven constituents in liver, brain and blood. The detected contents were 0.22,0.14 mug*g(-)(1),0.25 mg*L(-)(1) (4-allylanisole), 1.1, 0.39 mug*g(-)(1), 0.69 mg*L(-)(1) (methyl eugenol), 0.45, 0.13 mug*g(-)(1), 0.54 mg*L(-)(1) (2,3,5-trimethoxytoluene), 0.51, 0.15 mug*g(-)(1), 0.45 mg*L(-)(1) (3,4,5-trimethoxytoluene), 0.48, 0.039 mug*g(-)(1), 0.69 mg*L (-)(1) (sarisan), 2.2, 1.2 mug*g(-)(1), 1.5 mg*L(-)(1) (3,5-Dimethoxytoluene) and 1.3, 0.67 mug*g(-)(1), 1.1 mg*L(-)(1) (safrole) respectively. This HS-SPME-GC-MS method is rapid and convenient, with a small sample size, and applicable for the analysis and determination of volatile constituents in traditional Chinese medicines, which provides scientific data for further studies on effective substances and toxic substances in Asari Radix et Rhizoma.

Acaricidal activity of Asarum heterotropoides root-derived compounds and hydrodistillate constitutes toward Dermanyssus gallinae (Mesostigmata: Dermanyssidae).[Pubmed:26708137]

Exp Appl Acarol. 2016 Apr;68(4):485-95.

The acaricidal activity of Asarum heterotropoides root-derived principles, methyleugenol, safrole, 3-carene, alpha-asarone, pentadecane and A. heterotropoides root steam distillate constituents was tested against poultry red mites Dermanyssus gallinae (De Geer). All active principles were identified by spectroscopic analysis. Results were compared with those of two conventional acaricides, benzyl benzoate and N,N-diethyl-3-methylbenzamide (DEET). Methyleugenol (24 h LC50 = 0.57 microg/cm(2)) and safrole (24 h LC50 = 8.54 microg/cm(2)) were the most toxic compounds toward D. gallinae, followed by 3,4,5-trimethoxytoluene, 3,5-Dimethoxytoluene, estragole, alpha-terpineol, verbenone, eucarvone, linalool, and terpinen-4-ol (LC50 = 15.65-27.88 microg/cm(2)). Methyleugenol was 16.7x and 11.0x more toxic than benzyl benzoate (LC50 = 9.52 mug/cm(2)) and DEET (LC50 = 6.28 mug/cm(2)), respectively; safrole was 1.1x and 0.73x more toxic. Asarum heterotropoides root-derived materials, particularly methyleugenol and safrole, merit further study as potential acaricides. Global efforts to reduce the level of highly toxic synthetic acaricides in indoor environments justify further studies on A. heterotropoides root extract and steam distillate preparations containing the active constituents described as potential contact-action fumigants for the control of mites.

Contact toxicity and repellency of the essential oil of Liriope muscari (DECN.) bailey against three insect tobacco storage pests.[Pubmed:25608855]

Molecules. 2015 Jan 20;20(1):1676-85.

In order to find and develop new botanical pesticides against tobacco storage pests, bioactivity screening was performed. The essential oil obtained from the aerial parts of Liriope muscari was investigated by GC/MS and GC/FID. A total of 14 components representing 96.12% of the oil were identified and the main compounds in the oil were found to be methyl eugenol (42.15%) and safrole (17.15%), followed by myristicin (14.18%) and 3,5-Dimethoxytoluene (10.60%). After screening, the essential oil exhibit potential insecticidal activity. In the progress of assay, it showed that the essential oil exhibited potent contact toxicity against Tribolium castaneum, Lasioderma serricorne and Liposcelis bostrychophila adults, with LD50 values of 13.36, 11.28 microg/adult and 21.37 microg/cm2, respectively. The essential oil also exhibited strong repellency against the three stored product insects. At the same concentrations, the essential oil was more repellent to T. castaneum than to L. serricorne adults. The results indicate that the essential oil of Liriope muscari has potential to be developed into a natural insecticide or repellent for controlling insects in stored tobacco and traditional Chinese medicinal materials.