Contact and Repellant Activities of Zerumbone and Its Analogues from the Essential Oil of Zingiber zerumbet (L.) Smith against Lasioderma serricorne.

The contact toxicity and repellent activities of the essential oil extracted from the rhizomes of Zingiber zerumbet (L.) Smith (Zingiberaceae) was evaluated against cigarette beetles (Lasioderma serricorne). The essential oil obtained by hydrodistillation was investigated by GC-FID and GC-MS. The main constituents of the essential oil were zerumbone (40.2%), α-caryophyllene (8.6%), humulene epoxide II (7.3%), camphene (5.9%) and fenchene (4.7%). Zerumbone and its analogues totally are accounting for 60.3% of the essential oil. It was found that the essential oil possessed contact toxicity against L. serricorne adults with a LD50 value of 48.3 µg/adult. α-Caryophyllene (LD50 = 13.1 µg/adult) exhibited stronger contact toxicity against L. serricorne than humulene oxide (LD50 = 31.2 µg/adult), ß-caryophyllene (LD50 = 35.5 µg/adult) and zerumbone (LD50 = 42.4 µg/adult). Moreover, α-caryophyllene possessed strong repellent activity (Class IV and V, respectively) against the beetles at 78.63 nL/cm2, after 2 and 4 h treatment. The results indicate that zerumbone and its analogues might be developed into natural insecticides or repellents for control of cigarette beetles, but their bioactivities are affected by their structures.

Repellence of the main components from the essential oil of Glycosmis lucida Wall. ex Huang against two stored product insects.

A screening of Chinese medicinal herbs and wild plants for agrochemicals was carried out; the essential oil of Glycosmis lucida leaves was found to possess significant repellent activity against Tribolium castaneum and Liposcelis bostrychophila. It was found that the main components included elixene (19.81%), spathulenol (10.68%), anethole (12.05%), verbenone (10.32%) followed by ß-caryophyllene (6.87%). The essential oil, anethole and verbenone were strongly repellent against T. castaneum (96, 86 and 94%, respectively, at 15.73 nL cm-2) and L. bostrychophila (100, 68 and 72%, respectively, at 31.58 nL cm-2) after a 2h treatment. The results indicate that anethole and verbenone had the potential to be developed as natural repellents for control of stored product insects.

Chemical Composition of Essential Oils from Zanthoxylum bungeanum Maxim. and Their Bioactivities against Lasioderma serricorne.

Two essential oil samples were obtained from the pericarp of Zanthoxylum bungeanum with the methods of hydrodistillation (HD) and supercritical fluid CO2 extraction (SFE), their chemical components were identified, and their bioactivities against Lasioderma serricorne adults were evaluated. In the process of testing, the two samples showed significant bioactivities against Lasioderma serricorne adults. For an example, the SFE-sample expressed relatively stronger fumigant toxicity on Lasioderma serricorne adults (LC50 = 3.99 µg/mL air) than that of the HD-sample (LC50 = 12.54 µg/mL air). According to GC-MS analysis, the chemical components between two samples were different. The major chemical components for HD included linalool (25.99%), limonene (19.34%), linalyl anthranilate (12.22%), 4-terpinenol (10.49%), eucalyptol (6.53%) and α-terpineol (5.02%), while for SFE included nonanoic acid (21.43%), γ-terpinene (14.51%), eucalyptol (13.45%), α-terpineol (5.83%) and caryophyllene oxide (5.48%). The results showed that different chemical components result in different bioactivities. This work provides theoretical basis for traditional Chinese concept of antagonistic storage, and it also provides important information for the development and comprehensive utilization of Zanthoxylum bungeanum.

Chemical Constituents and Activity of Murraya microphylla Essential Oil against Lasioderma serricorne.

The chemical composition, contact and repellent activities of the essential oil from Murraya microphylla branches and leaves against Lasioderma serricorne adults were determined and six compounds from the essential oil were isolated as well. The essential oil of M microphylla obtained by hydrodistillation was analyzed by gas chromatography-mass spectrometric (GC-MS) analysis; 22 compounds were identified. The main constituents of the essential oil included ß-caryophyllene (18.0%), α-pinene (13.8%), spathulenol (9.5%), α-humulene (6.0%), γ-elemene (5.1%) and zingiberene (4.6%), followed by α-cadinol (3.9%) and caryophyllene oxide (3.8%). Six of these compounds were isolated and fully identified as α-pinene, ß-caryophyllene, α-humulene, caryophyllene oxide, spathulenol and α-cadinol. L. serricorne adults had different sensitivities to the crude essential oil and isolated compounds. α-Humulene exhibited the strongest contact activity against L. serricorne, showing an LD50 value of 13.1 µg adult(-1). However, spathulenol, the crude essential oil and α-cadinol showed stronger contact activity against L. serricorne than caryophyllene oxide and ß-caryophyllene. The essential oil, α-humulene and spathulenol showed comparable repellency against L. serricorne adults at 2 h after exposure, relative to the positive control, DEET. The results demonstrate that the essential oil and isolated compounds exhibited important contact and repellent activities against L. serricorne. Thus, they could become potential natural insecticides or repellents for control of insects in stored products.

Essential Oil of Amomum maximum Roxb. and Its Bioactivities against Two Stored-Product Insects.

Amomum maximum Roxb. is a perennial herb distributed in South China and Southeast Asia. The objective of this work was to analyze the chemical constituents and assess insecticidal and repellent activities of the essential oil from Amomum maximum fruits against Tribolium castaneum (Herbst) and Liposcelis bostrychophila (Badonnel). The essential oil was obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detector and gas chromatography-mass spectrometry. The main components of the essential oil were identified to be ß-pinene (23.39%), ß-caryophyllene (16.43%), α-pinene (7.55%), sylvestrene (6.61%) and ç-cadinene (4.19%). It was found that the essential oil of A. maximum fruits possessed contact and fumigant toxicities against T. castaneum adults (LD50 = 29.57 µg/adult and LC(50) = 23.09 mg/L air, respectively) and showed contact toxicity against L. bostrychophila (LD(50) = 67.46 µg/cm(2)). Repellency of the crude oil was also evaluated. After 2 h treatment, the essential oil possessed 100% repellency at 78.63 nL/cm(2) against T. castaneum and 84% repellency at 63.17 nL/cm(2) against L. bostrychophila. The results indicated that the essential oil of A. maximum fruits had the potential to be developed as a natural insecticide and repellent for control of T. castaneum and L. bostrychophila.

Repellent activity of Glycosmis plant extracts against two stored product insects / Actividad repelente de extractos de plantas Glycosmis contra dos insectos de productos almacenados

In the present study, the repellent activities of the leaf and/or stem crude extracts of Glycosmis lucida Wall. ex Huang, G. craibii var. glabra, G. craibii Tanaka, G. oligantha Huang, G. pentaphylla (Retz) Correa. and G. esquirolii (Levl.) Tanaka were analyzed by using assays on petri dishes against Tribolium castaneum and Liposcelis bostrychophila. The leaf and stem extracts of G. lucida, G. craibii var. glabra, G. craibii Tanaka, G. oligantha and G. esquirolii possessed significant repellent activities against T. castaneum, the same level repellent with the positive control, DEET. However, the extracts of G. pentaphylla, no repellency but some insect attractant was observed. Moreover, they also showed repellent activities against L. bostrychophila. These results indicate that extracts from G. lucida and G. oligantha leaf could be a source of novel repellent against insects.

En el presente estudio, las actividades repelentes de la hoja y/o tronco de los extractos crudos de Glycosmis lucida Wall. ex Huang, G. craibii var. glabra, G. craibii Tanaka, G. oligantha Huang, G. pentaphylla (Retz) Correa y G. esquirolii (Levl.) Tanaka se analizaron mediante el uso de ensayos en placas de Petri contra Tribolium castaneum y Liposcelis bostrychophila. Los extractos de las hojas y tallo de G. lucida, G. craibii var. glabra, G. craibii Tanaka, G. oligantha y G. esquirolii poseían actividades repelentes significativas contra T. castaneum, el mismo nivel repelente del control positivo, el DEET. Sin embargo, los extractos de G. pentaphylla, no se observó la repelencia pero sí actividad atrayente de insectos. Por otra parte, también se mostraron las actividades repelentes contra L. bostrychophila. Estos resultados indican que los extractos de hojas de G. lucida y G. oligantha podrían ser una fuente de repelente contra los insectos.

Insecticidal Constituents of Essential Oil Derived from Zanthoxylum armatum against Two Stored-Product Insects.

In the course of our search for natural bioactive chemicals and investigations on their insecticidal activities from some medicinal plants growing in China, the essential oil derived from the twigs of Zanthoxylum armatum (Rutaceae) was found to possess strong insecticidal activities against two stored-product insects, Lasioderma serricorne and Tribolium castaneum. A total of 32 constituents of the essential oil were identified by GC and GC-MS analysis, and it revealed (E)-anethole (20.5%), 1,8-cineole (14.0%), 2-tridecanone (12.5%), limonene (9.0%) and piperitone (8.0%) as major components, followed by ß-phellandrene (6.3%), ß-pinene (5.1%) and 4-terpineol (4.4%). From the essential oil, five compounds were isolated and identified as (E)-anethole, 1,8-cineole, 2-tridecanone, limonene and piperitone. The results of insecticidal bioassays showed that the essential oil of Z. armatum exhibited strong fumigant toxicity towards L. serricorne and T. castaneum with LC50 values of 13.83 and 4.28 mg/L air, respectively, and also possessed contact toxicity against two insect species with LD50 values of 18.74 and 32.16 µg/adult, respectively. Among the active compounds, piperitone performed the strongest fumigant toxicity against L. serricorne (LC50 = 1.21 mg/L air) and contact toxicity against T. castaneum (LD50 = 3.16 µg/adult). 1,8-Cineole, limonene and piperitone showed similar fumigant toxicity against T. castaneum with LC50 values of 5.47, 6.21 and 7.12 mg/L air, respectively. Meanwhile, L. serricorne was the most sensitive to 2-tridecanone (LD50 = 5.74 µg/adult) in the progress of contact toxicity assay.

Contact Toxicity and Repellency of the Essential Oil of Dictamnus dasycarpus Roots from China against Two Stored-Product Insects.

During our screening program for new agrochemicals from traditional medicinal herbs, Dictamnus dasycarpus was found to possess contact toxicity and repellent activity against the cigarette beetle Lasioderma serricorne and the booklouse Liposcelis bostrychophila. The essential oil obtained by hydrodistillation of D. dasycarpus roots was characterized by GC-FID and GC/MS analyses, and the main components identified were syn-7-hydroxy-7-anisylnorbornene (1, 49.9%), 1,3,4,5,6,7-hexahydro-2H-inden-2-one (2, 11.6%), 5,6-diethenyl-1-methylcyclohexene (3, 7.4%), and 3,9-dimethyltricyclo[4.2.1.1(2,5)]dec-3-en-9-ol (4, 6.35%). The D. dasycarpus root oil exhibited strong contact toxicity against L. serricorne adults and L. bostrychophila, with LD50 values of 12.4 µg/adult and 27.2 µg/cm(2), respectively. Moreover, the essential oil also showed strong repellency against both stored-product insects tested.

Contact toxicity and repellency of the essential oil from Mentha haplocalyx Briq. against Lasioderma serricorne.

The chemical composition of the essential oil obtained by hydrodistillation from the aerial parts of Mentha haplocalyx was investigated by GC-FID and GC/MS analyses. In sum, 23 components, representing 92.88% of the total oil composition, were identified, and the main compounds were found to be menthol (59.71%), menthyl acetate (7.83%), limonene (6.98%), and menthone (4.44%). By bioassay-guided fractionation (contact toxicity), three compounds were obtained from the essential oil and identified as menthol, menthyl acetate, and limonene. The essential oil and the three isolated compounds exhibited potent contact toxicity against Lasioderma serricorne adults, with LD50 values of 16.5, 7.91, 5.96, and 13.7 µg/adult, respectively. Moreover, the oil and its isolated compounds also exhibited strong repellency against L. serricorne adults. At the lower concentrations tested and at 2 h after exposure, menthol showed even significantly stronger repellency than the positive control DEET. The study revealed that the bioactivity properties of the essential oil can be attributed to the synergistic effects of its diverse major and minor components, which indicates that the M. haplocalyx oil and its isolated compounds have potential for the development as natural insecticides and/or repellents to control insects in stored grains and traditional Chinese medicinal materials.

Bioactivity and chemical constituents of the essential oil from Dendranthema indicum (L.) Des Moul. against two stored insects.

Dendranthema indicum (L.) Des Moul. is a perennial herb commonly used as a traditional Chinese medicine for a long time. In this work, we took Dendranthema indicum as a target plant and two stored insects which include Tribolium castaneum and Stegobium paniceum adults as target insects. Essential oil obtained from Dendranthema indicum was analyzed by gas chromatography-mass spectrometry (GC-MS). A total of 31 components representing 92.44% of the oil were identified and the main compounds were found to be chamazulene (15.93%), ß-caryophyllene (13.78%), germacrene D (9.11%), and b-cis-farnesene (6.59%). With a further isolation, three constituents were obtained from the essential oil and identified as chamazulene, ß-caryophyllene and eucalyptol. Significantly, in the progress of assay, it showed that the essential oil and chamazulene exhibited stronger insecticidal and repellent activities against Stegobium paniceum than Tribolium castaneum. The results indicate that additional to its traditional use as Chinese medicinal herb, the essential oil of Dendranthema indicum aerial parts and isolated compounds have potential to be developed into natural insecticides or repellents for control of insects in stored grains.

Repellent Constituents of essential oil from Citrus wilsonii stem barks against Tribolium castaneum.

The essential oil obtained from Citrus wilsonii Tanaka stem barks with hydrodistillation was investigated by GC-FID and GC-MS. The main components of the essential oil were identified to be nerol acetate (44.5%), nerol (13.6%), citronellyl propionate (13.5%) and α-terpineol (3.6%). Among them, the four active constituents, predicted with a bioactivity-test, were isolated and identified as nerolacetate, nerol, citronellyl propionate and α-terpineol. It was found that the essential oil of C. wilsonii stem barks possessed strong repellency (86% and 92%, respectively, at 78.6 nL/cm2, after 2 and 4 h treatment) against Tribolium castaneum adults. Repellency of the four active compounds was also determined. Nerolacetate, nerol, citronellyl propionate and α-terpineol were strongly repellent (100%, 100%, 90% and 96%, respectively, at 15.7 nL/cm2, after 2h treatment) against T. castaneum. Nerol exhibited the same level of repellency as the positive control, DEET. The results indicate that the essential oil of C. wilsonii stem barks and its active compounds have the potential to be developed as natural repellents for control of T. castaneum.

Composition and repellency of the essential oils of Evodia calcicola Chun ex Huang and Evodia trichotoma (Lour.) Pierre against three stored product insects.

During our screening program for agrochemicals from Chinese medicinal herbs and wild plants, the essential oils of Evodia calcicola and Evodia trichotoma leaves were found to possess strong repellency against the red flour beetle Tribolium castaneum adults, the cigarette beetle Lasioderma serricorne adults and the booklouse Liposcelis bostrychophila. The two essential oils obtained by hydrodistillation were investigated by GC-MS. The main components of E. calcicola essential oil were identified to be (-)-ß-pinene (44.02%), ß-phellandrene (20.93%), ocimene (16.49%), and D-limonene (9.87%). While the main components of the essential oil of E. trichotoma were D-limonene (69.55%), 1R-a-pinene (11.48%), caryophyllene (2.80%) and spathulenol (2.24%). Data showed that T. castaneum was the most sensitive than other two stored product insects. Compared with the positive control, DEET (N, N-diethyl-3- methylbenzamide), the two essential oils showed the same level repellency against the red flour beetle. However, the essential oil of E. trichotoma showed the same level repellency against the cigarette beetle, while E. calcicola essential oil possessed the less level repellency against L. serricorne, relative to the positive control, DEET. Moreover, the two crude oils also exhibited strong repellency against L. bostrychophila, but lesser level repellency than the positive control, DEET. Thus, the essential oils of E. calcicola and E. trichotoma may be potential to be developed as a new natural repellent in the control of stored product insects.

Cytotoxic compounds isolated from Murraya tetramera Huang.

A new compound and seven known compounds were isolated from Murraya tetramera Huang for the first time, and they were identified with NMR and MS spectral analysis. It was confirmed that the new compound was 10-methoxy-7-methyl-2H-benzo[g]chromen-2-one (3) and the others were ß-eudesmol (1), trans-3ß-(1-hydroxy-1-methylethyl)-8aß-methyl-5-methylenedecalin-2-one (2), 5,7-dimethoxy-8-[(Z)-3'-methyl-butan-1',3'-dienyl]coumarin (4), 7-geranyloxy-6-methoxycoumarin (5), 5,7-dimethoxy-8-(3-methyl-2-oxo-butyl)coumarin (6), murrangatin acetate (7) and toddalenone (8). Furthermore, the cytotoxic activity against human lung adenocarcinoma (A549), human hepatocellular carcinoma cells (SMMC-7721), human bladder tumor cells (EJ), human cervical carcinoma cells (HeLa), and human B-lineage acute lymphoblastic leukemia 1 cells (BALL-1) was evaluated for all compounds. It was found that five of them displayed various degrees of cytotoxicity against different testing targets. Compound 1 showed significant cytotoxic activity against the five cell lines (A549, SMMC-7721, EJ, Hela and BALL-1). Compounds 2 and 5 showed significant cytotoxicity against three cell lines (A549, SMMC-7721 and BALL-1). Compound 4 showed significant cytotoxicity against three cell lines (A549, EJ and BALL-1). However, compound 3 only showed fair cytotoxicity against the BALL-1 cell line. The structure-active relationships were investigated as well. These active compounds might be potential lead compounds for the treatment of cancer.

One new alkaloid from Chelidonium majus L.

One new alkaloid, together with 10 known compounds were isolated from the aerial parts of Chelidonium majus L. by repeated silica gel column chromatography. Their chemical structures were elucidated on the basis of physicochemical and spectroscopic data. Among them, 6-acetonyldihydrochelerythrine (4), 6-acetonyldihydrosanguinarine (5), 6-ketenesanguinarine (6), demethylchelerythrine (7) and demethylsanguinarine (11) were isolated for the first time from this plant. Compound 6 was identified as a new compound. These compounds were screened for cytotoxicity against human non-small lung carcinoma (H1299), breast cancer (MCF-7) and liver cancer (SMMC-7721). In a series of cytotoxic tests, compounds 9 and 10 displayed potent cytotoxic activity against H1299, MCF-7 and SMMC-7721, with the IC50 values of 8.16-35.25 µg/mL.

Cytotoxic constituents from the stems of Clausena lansium (Lour.) Skeels.

Six compounds were isolated from the stems of Clausena lansium (Lour.) Skeels by repeated sillica gel column chromatography. Their chemical structures were elucidated on the basic of physicochemical and spectroscopic data. Among them, 8-geranyloxypsolaren (3) and 2-methoxy-1-(3-methyl-buten-1-yl)-9H-carbazole-3-carbaldehyde (6) were isolated for the first time from this plant. These compounds were screened for cytotoxicity in human cervical cancer (Hela), leukemia (K562), lung cancer (A549), non-small lung carcinoma (H1299) and liver cancer (SMMC-7721). Within the series of cytotoxic tests, compounds 4-6 displayed potent cytotoxic activity against H1299 and SMMC-7721, with the IC50 values of 6.19 to 26.84 µg/mL.

Antioxidant phenolic compounds from Pu-erh tea.

Eight compounds were isolated from the water extract of Pu-erh tea and their structures were elucidated by NMR and MS as gallic acid (1), (+)-catechin (2), (−)-epicatechin (3), (−)-epicatechin-3-O-gallate (4), (−)-epigallocatechin-3-O-gallate (5), (−)-epiafzelechin- 3-O-gallate (6), kaempferol (7), and quercetin (8). Their in vitro antioxidant activities were assessed by the DPPH and ABTS scavenging methods with microplate assays. The relative order of DPPH scavenging capacity for these compounds was compound 8 > compound 7 > compound 1 > compound 6 > compound 4 ≈ compound 5 > compound 2 > VC (reference) > compound 3, and that of ABTS scavenging capacity was compound 1 > compound 2 > compound 7 ≈ compound 8 > compound 6 > compound 5 > compound 4 > VC (reference) > compound 3. The results showed that these phenolic compounds contributed to the antioxidant activity of Pu-erh tea.

Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae).

In recent years, uses of environment friendly and biodegradable natural insecticides of plant origin have received renewed attention as agents for vector control. The aim of this research was to determine larvicidal activity of the essential oil derived from roots of Saussurea lappa (Compositae) and the isolated constituents against the larvae of the Culicidae mosquito Aedes albopictus. Essential oil of S. lappa roots was obtained by hydrodistillation and analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). A total of 39 components of the essential oil of S. lappa roots were identified. The essential oil has higher content of (79.80%) of sesquiterpenoids than monoterpenoids (13.25%). The principal compounds in S. lappa essential oil were dehydrocostus lactone (46.75%), costunolide (9.26%), 8-cedren-13-ol (5.06%), and α-curcumene (4.33%). Based on bioactivity-directed fractionation, dehydrocostus lactone and costunolide were isolated from S. lappa essential oil. Dehydrocostus lactone and costunolide exhibited strong larvicidal activity against A. albopictus with LC(50) values of 2.34 and 3.26 µg/ml, respectively, while the essential oil had an LC(50) value of 12.41 µg/ml. The result indicated that the essential oil of S. lappa and the two isolated constituents have potential for use in control of A. albopictus larvae and could be useful in search of newer, safer and more effective natural compounds as larvicides.

Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais.

The screening of several Chinese medicinal plants for insecticidal principles showed that essential oil of Rhododendron anthopogonoides flowering aerial parts possessed significant toxicity against maize weevils, Sitophilus zeamais. A total of 37 components were identified in the essential oil and the main constituents of the essential oil were 4-phenyl-2-butanone (27.22%), nerolidol (8.08%), 1,4-cineole (7.85%), caryophyllene (7.63%) and γ-elemene (6.10%), followed by α-farnesene (4.40%) and spathulenol (4.19%). Repeated bioactivity-directed chromatographic separation on silica gel columns led us to isolate three compounds, namely 4-phenyl-2-butanone, 1,4-cineole, and nerolidol. 4-Phenyl-2-butanone shows pronounced contact toxicity against S. zeamais (LD50 = 6.98 mg/adult) and was more toxic than either 1,4-cineole or nerolidol (LD50 = 50.86 mg/adult and 29.30 mg/adult, respectively) against the maize weevils, while the crude essential oil had a LD50 value of 11.67 mg/adult. 4-Phenyl-2-butanone and 1,4-cineole also possessed strong fumigant toxicity against the adults of S. zeamais (LC50 = 3.80 mg/L and 21.43 mg/L) while the crude essential oil had a LC50 value of 9.66 mg/L.

Antifeedant diterpenoids against Tribolium castaneum from the stems and twigs of Ceriops tagal (Rhizophoraceae).

The screening of several Chinese mangrove plants for insecticidal principles showed that ethanol extract of Ceriops tagal stems and twigs possessed significant feeding deterrent activity against the red flour beetle, Tribolium castaneum (Family: Rhizophoraceae). From the ethanol extract, three feeding deterrent diterpenoids were isolated by bioassay-guided fractionation. The compounds were identified as tagalsin A, B, and H on the basis of their phytochemical and spectral data. Tagalsin A, B, and H exhibited strong feeding deterrent activity against T. castaneum adults with EC50 values of 375.3 ppm, 277.3 ppm, and 285.45 ppm, respectively.

Nematocidal flavone-C-glycosides against the root-knot nematode (Meloidogyne incognita) from Arisaema erubescens tubers.

A screening of several Chinese medicinal herbs for nematicidal properties showed that Arisaema erubescens (Wall.) Schott tubers possessed significant nematicidal activity against the root-knot nematode (Meloidogyne incognita). From the ethanol extract, two nematicidal flavone-C-glycosides were isolated by bioassay-guided fractionation. The compounds were identified as schaftoside and isoschaftoside on the basis of their phytochemical and spectral data. Schaftoside and isoschaftoside possessed strong nematicidal activity against M. incognita (LC(50) = 114.66 µg/mL and 323.09 µg/mL, respectively) while the crude extract of A. erubescens exhibited nematicidal activity against the root-knot nematode with a LC(50) value of 258.11 µg/mL.