Study of Methanol Extracts from Different Parts of Peganum harmala L. Using 1H-NMR Plant Metabolomics

A nuclear magnetic resonance- (NMR-) based metabolomics method was used to identify differential metabolites of methanol extracts obtained from six parts of Peganum harmala L. (P. harmala), namely, the root, stem, leaf, flower, testa, and seed. Two multivariate statistical analysis methods, principal component analysis (PCA) and partial least squares-discriminant analysis (PLS-DA), were combined to clearly distinguish among the P. harmala samples from the six different parts. Eleven differential components were screened by the PLS-DA loading plot, and the relative contents were calculated by univariate analysis of variance. Chemometric results showed significant differences in the metabolites of the different parts of P. harmala. The seeds contained large amounts of harmaline, harmine, and vasicine compared to other organs. The acetic acid, proline, lysine, and sucrose contents of the roots were significantly higher than those of the other parts. In the testa, the vasicine, asparagine, choline, and 4-hydroxyisoleucine contents were clearly dominant. The obtained data revealed the distribution characteristics of the metabolomes of the different P. harmala parts and provided fundamental knowledge for the rational development of its medicinal parts

Contact and Repellent Activities of the Essential Oil from Juniperus formosana against Two Stored Product Insects

The chemical composition of the essential oil from Juniperus formosana leaves and its contact and repellent activities against Tribolium castaneum and Liposcelis bostrychophila adults were investigated. The essential oil of J. formosana leaves was obtained by hydrodistillation and analyzed by GC-MS. A total of 28 components were identified and the main compounds in the essential oil were α-pinene (21.66%), 4-terpineol (11.25%), limonene (11.00%) and β-phellandrene (6.63%). The constituents α-pinene, 4-terpineol and d-limonene were isolated from the essential oil. It was found that the essential oil exhibited contact activity against T. castaneum and L. bostrychophila adults (LD50 = 29.14 μg/adult and 81.50 µg/cm2, respectively). The compound 4-terpineol exhibited the strongest contact activity (LD50 = 7.65 μg/adult). In addition, data showed that at 78.63 nL/cm2, the essential oil and the three isolated compounds strongly repelled T. castaneum adults. The compounds α-pinene and d-limonene reached the same level (Class V) of repellency as DEET (p = 0.396 and 0.664) against L. bostrychophila at 63.17 nL/cm2 after 2 h treatment. The results indicate that the essential oil and the isolated compounds have potential to be developed into natural insecticides and repellents to control insects in stored products

The Chemical Composition of Essential Oils from Cinnamomum camphora and Their Insecticidal Activity against the Stored Product Pests

To investigate the chemical composition and insecticidal activity of the essential oils of certain Chinese medicinal herbs and spices, the essential oils were extracted from the stem barks, leaves, and fruits of Cinnamomum camphora (L.) Presl, which were found to possess strong fumigant toxicity against Tribolium castaneum and Lasioderma serricorne adults. The essential oils of the plants were extracted by the method of steam distillation using a Clavenger apparatus. Their composition was determined by gas chromatography/mass spectrometric (GC-MS) analyses (HP-5MS column), and their insecticidal activity was measured by seal-spaced fumigation. D-camphor (51.3%), 1,8-cineole (4.3%), and α-terpineol (3.8%), while D-camphor (28.1%), linalool (22.9%), and 1,8-cineole (5.3%) were the main constituents of its fruits. The essential oils of the C. camphora all showed fumigant and contact toxicity. Other compounds exhibited various levels of bioactivities. The results indicate that the essential oils of C. camphora and its individual compounds can be considered a natural resource for the two stored-product insect management

Chemical Constituents of Supercritical Extracts from Alpinia officinarum and the Feeding Deterrent Activity against Tribolium castaneum

Alpinia officinarum has been confirmed to possess bioactivities against some pests. In this work, a sample was obtained from A. officinarum rhizomes by supercritical fluid CO2 extraction (SFE). According to GC-MS analysis, the main chemical components for SFE-sample included benzylacetone (26.77%), 1,7-diphenyl-5-hydroxy-3-heptanone (17.78%), guaiacylacetone (10.03%) and benzenepropanal (7.42%). The essential oil of A. officinarum rhizomes (LD50 = 20.71 μg/adult) exhibited more contact toxicity than SFE extract (LD50 = 82.72 μg/adult) against Tribolium castaneum. From SFE extracts, one new compound, 1-phenyl-4-(16,17-dimethyl-9,13-octadiene)-5-isopentenyl-7-(4”-methoxyl-3”-hydroxyl-phenyl)-3-heptanone (3), together with five known compounds identified as 5-hydroxy-1,7-diphenyl-3-heptanone (1), 1,7-diphenyl-4-hepten-3-one (2), galangin (4), galangin-3-methyl ether (5) and pinocembrin (6), were isolated and their feeding deterrent activities against T. castaneum adults were assessed. It was found that compounds 1–6 had feeding deterrent activities against T. castaneum with feeding deterrent indices of 18.21%, 18.94%, 19.79%, 26.99%, 20.34%, and 35.81%, respectively, at the concentration of 1500 ppm. Hence, the essential oil and SFE extracts/compounds of A. officinarum rhizomes represent promising alternatives in the control of T. castaneum adults

Identification of Repellent and Insecticidal Constituents from Artemisia mongolica Essential Oil against Lasioderma serricorne

The aims of this research were to determine the chemical composition and insecticidal and repellent activities of the Artemisia mongolica essential oil against Lasioderma serricorne and to isolate active constituents from the essential oil. The essential oil of A. mongolica was obtained by hydrodistillation and 36 components were identified with GC-MS. Eucalyptol (39.88%), (S)-cis-verbenol (14.93%), 4-terpineol (7.20%), (−)-camphor (6.02%), and α-terpineol (4.20%) were found to be major components. With a further isolation process, five constituents obtained from the essential oil were identified as eucalyptol, verbenol, 4-terpineol, camphor, and α-terpineol. In the progress of assay, it showed that L. serricorne adults had different sensitivities to the crude essential oil and isolated constituents. 4-Terpineol exhibited strongest contact activity against L. serricorne, showing the LD50 value of 8.62 μg/adult. Moreover, camphor and α-terpineol showed stronger fumigant activity (LC50=2.91 and 3.27 mg/L air, resp.) against L. serricorne than crude essential oil and other constituents. In addition, the essential oil, eucalyptol, verbenol, and α-terpineol showed comparable repellency against L. serricorne adults. The results indicate that the essential oil and isolated compounds have potential to provide more efficient and safer natural insecticides or repellents for control of insects in food and Chinese medicinal materials preservation

Toxic and Repellent Effects of Volatile Phenylpropenes from Asarum heterotropoides on Lasioderma serricorne and Liposcelis bostrychophila

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 (LC50 = 4.99, 10.82, and 18.93 mg/L air, respectively). Safrole and 3,5-dimethoxytoluene possessed significant fumigant toxicity against L. bostrychophila (LC50 = 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

Raw data ( 1H NMR specra) obtained from polar metabolite extraction of Peganum harmala L. from NMR-based metabolomic profiling of <i>Peganum harmala</i> L. reveals dynamic variations between different growth stages

variable bins were normalized to the whole spectral area and 20 samples data were listed in this file

Supplementary figures and tables from "NMR-Based Metabolomic Profiling Of Peganum Harmala L. Reveals Dynamic Variations Derived From Different Growth Stages" from NMR-based metabolomic profiling of <i>Peganum harmala</i> L. reveals dynamic variations between different growth stages

Plot design for sampling;Xinjiang changji region climate data in 2014;Identification and relative quantification of principal metabolites;1D and 2D NMR spectra of samples; Permutation test model validation plots

Antifeedant Activities of Lignans from Stem Bark of Zanthoxylum armatum DC. against Tribolium castaneum

The speciation of a methanolic extract of Zanthoxylum armatum stem bark has enabled the isolation and characterization of 11 known lignans. Among them, five compounds (6, 8–11) are reported in this plant for the first time. All of the chemical structures were elucidated on the basis of NMR spectral analysis. Additionally, their antifeedant activities against Tribolium castaneum were evaluated scientifically. Among them, asarinin (1), with an EC50 of 25.64 ppm, exhibited a much stronger antifeedant activity than the positive control, toosendanin (EC50 = 71.69 ppm). Moreover, fargesin (2), horsfieldin (3), and magnolone (10), with EC50 values of 63.24, 68.39, and 78.37 ppm, showed almost the same antifeedant activity as the positive control. From the perspective of structure-effectiveness relationship, compounds with the chemical group of methylenedioxy exhibited higher antifeedant activities and have potential to be developed into novel antifeedants or potential lead compounds to protect food and crops in storage

Cytotoxicity of Aporphine, Protoberberine, and Protopine Alkaloids from Dicranostigma leptopodum (Maxim.) Fedde

Nine alkaloids with three different structural skeletons were isolated from Dicranostigma leptopodum (Maxim.) Fedde (Papaveraceae) by repeated silica gel column chromatography. Their chemical structures were identified on the basic of physicochemical and spectroscopic data. Among them, 10-O-methylhernovine (1), nantenine (2), corytuberine (3), lagesianine A (4), and dihydrocryptopine (9) were first isolated from this plant. With a series of cytotoxic tests, compounds 2, 3, and 7 displayed cytotoxicity against SMMC-7721 with IC 50 values of 70.08 ± 4.63, 73.22 ± 2.35, and 27.77 ± 2.29 M, respectively