Shu Shan Du

Components and Insecticidal Activity against the Maize Weevils of Zanthoxylum schinifolium Fruits and Leaves

In our screening program for new agrochemicals from Chinese medicinal herbs and wild plants, Zanthoxylum schinifolium essential oils were found to possess strong insecticidal activity against the maize weevil Sitophilus zeamais. The essential oils of Z. schinifolium fruits and leaves were extracted via hydrodistillation and investigated by GC and GC-MS. Estragole (69.52%) was the major compound of the essential oil of fresh fruits, followed by linalool (8.63%) and limonene (4.34%) and 94.33% of the total components were monoterpenoids. The main components of the essential oil of fresh leaves were linalool (12.94%), ar-tumerone (8.95%), limonene (6.45%) and elixene (5.43%) and only 50.62% were monoterpenoids. However, the essential oil from purchased fruits contained linalool (33.42%), limonene (13.66%) and sabinene (5.72%), followed by estragole (4.67%), nerol (4.56%) and 4-terpineol (4.27%). Estragole, linalool and sabinene were separated and purified by silica gel column chromatography and preparative thin layer chromatography, and further identified by means of physicochemical and spectrometric analysis. The essential oil from the fresh fruits (LD50 = 15.93 μg/adult) possessed two times more toxicity to the insects compared with that of fresh leaves (LD50 = 35.31 μg/adult). Estragole, linalool and sabinene exhibited contact activity against S. zeamais with LD50 values of 17.63, 13.90 and 23.98 μg/adult, respectively. The essential oils of Z . schinifolium possessed strong fumigant toxicity against S. zeamais adults with LC50 values of 13.19 mg/L (fresh fruits), 24.04 mg/L (fresh leaves) and 17.63 mg/L (purchased fruits). Estragole, linalool and sabinene also exhibited strong fumigant toxicity against the maize weevils with LC50 values of 14.10, 10.46 and 9.12 mg/L, respectively.

Insecticidal activity of essential oil of Carum Carvi fruits from China and its main components against two grain storage insects.

During our screening program for agrochemicals from Chinese medicinal herbs and wild plants, the essential oil of Carum carvi fruits was found to possess strong contact toxicity against Sitophilus zeamais and Tribolium castaneum adults, with LD50 values of 3.07 and 3.29 μg/adult, respectively, and also showed strong fumigant toxicity against the two grain storage insects with LC50 values of 3.37 and 2.53 mg/L, respectively. The essential oil obtained by hydrodistillation was investigated by GC and GC-MS. The main components of the essential oil were identified to be (R)-carvone (37.98%) and D-limonene (26.55%) followed by α-pinene (5.21), cis-carveol (5.01%) and β-myrcene (4.67%). (R)-Carvone and D-limonene were separated and purified by silica gel column chromatography and preparative thin layer chromatography, and further identified by means of physicochemical and spectrometric analysis. (R)-Carvone and D-limonene showed strong contact toxicity against S. zeamais (LD50 = 2.79 and 29.86 μg/adult) and T. castaneum (LD50 = 2.64 and 20.14 μg/adult). (R)-Carvone and D-limonene also possessed strong fumigant toxicity against S. zeamais (LC50= 2.76 and 48.18 mg/L) and T. castaneum adults (LC50= 1.96 and 19.10 mg/L).

Identification of Insecticidal Constituents of the Essential Oil of Curcuma wenyujin Rhizomes Active against Liposcelis bostrychophila Badonnel

The aim of this research was to determine the chemical composition and insecticidal activity of the essential oil of Curcuma wenyujin Y.H. Chen et C. Ling rhizomes against the booklouse Liposcelis bostrychophila Badonnel and to isolate any insecticidal constituents from the essential oil. The essential oil of C. wenyujin rhizomes was obtained by hydrodistillation and analyzed by GC-MS. A total of 43 components of the essential oil were identified and the principal compounds in the essential oil were 1,8-cineole (15.26%), camphor (10.12%), germacrone (6.86%), β-elemene (6.33%), curzerene (6.70%), and β-elemenone (5.23%). followed by curzerenone (4.52%), curdione (4.45%) and linalool (4.43%). Based on bioactivity-guided fractionation, the two main active constituents were isolated from the essential oil and identified as 1,8-cineole and camphor. The essential oil of C. wenyujin rhizomes exhibited contact toxicity against L. bostrychophila with an LD50 value of 208.85 µg/cm2. Camphor (LD50 = 207.26 µg/cm2) exhibited stronger contact toxicity than 1,8-cineole (LD50 = 1048.75 µg/cm2) against booklouse. The essential oil of C. wenyujin (LC50 = 2.76 mg/L air) also possessed fumigant toxicity against L. bostrychophila, while the two constituents, camphor and 1,8-cineole had LC50 values of 1.03 mg/L air and 1.13 mg/L air, respectively. The results indicate that the essential oil of C. wenyujin rhizomes and its constituent compounds have potential for development as natural insecticides or fumigants for control of insects in stored grains.

Identification of Insecticidal Constituents of the Essential Oil of Acorus calamus Rhizomes against Liposcelis bostrychophila Badonnel

The aim of this research was to determine the chemical composition of the essential oil of Acorus calamus rhizomes, its insecticidal activity against the booklouse, (Liposcelis bostrychophila) and to isolate any insecticidal constituents from the essential oil. The essential oil of A. calamus rhizomes was obtained by hydrodistillation and analyzed by GC-FID and GC-MS. A total of 32 components of the essential oil of A. calamus rhizomes was identified and the principal compounds in the essential oil were determined to be α-asarone (50.09%), (E)-methylisoeugenol (14.01%), and methyleugenol (8.59%), followed by β-asarone (3.51%), α-cedrene (3.09%) and camphor (2.42%). Based on bioactivity-guided fractionation, the three active constituents were isolated from the essential oil and identified as methyleugenol, (E)-methylisoeugenol and α-asarone. The essential oil exhibited contact toxicity against L. bostrychophila with an LD50 value of 100.21 µg/cm2 while three constituent compounds, α-asarone, methyleugenol, and (E)-methylisoeugenol had LD50 values of 125.73 µg/cm2, 103.22 µg/cm2 and 55.32 µg/cm2, respectively. Methyleugenol and (E)-methylisoeugenol possessed fumigant toxicity against L. bostrychophila adults with LC50 values of 92.21 μg/L air and 143.43 μg/L air, respectively, while the crude essential oil showed an LC50 value of 392.13 μg/L air. The results indicate that the essential oil of A. calamus rhizomes and its constituent compounds have potential for development into natural fumigants/insecticides for control of the booklice.

Identification of Repellent and Insecticidal Constituents of the Essential Oil of Artemisia rupestris L. Aerial Parts against Liposcelis bostrychophila Badonnel

The aim of this research was to determine the chemical composition and insecticidal and repellent activity of the essential oil of Artemisia rupestris L. aerial parts against the booklice Liposcelis bostrychophila Badonnel and isolation of insecticidal and repellent constituents from the essential oil. The essential oil of A. rupestris was obtained by hydrodistillation and analyzed by GC-MS. A total of 30 components of the essential oil of A. rupestris was identified and the principal compounds in the essential oil were α-terpinyl acetate (37.18%), spathulenol (10.65%), α-terpineol (10.09%), and linalool (7.56%), followed by 4-terpineol (3.92%) and patchoulol (3.05%). Based on bioactivity-guided fractionation, the four active constituents were isolated from the essential oil and identified as α-terpineol, α-terpinyl acetate, 4-terpineol and linalool. The essential oil of A. rupestris exhibited contact toxicity against L. bostrychophila with LD50 value of 414.48 µg/cm2. α-Terpinyl acetate (LD50 = 92.59 µg/cm2) exhibited stronger contact toxicity against booklice than α-terpineol (LD50 = 140.30 µg/cm2), 4-terpineol (LD50 = 211.35 µg/cm2), and linalool (LD50 = 393.16 µg/cm2). The essential oil of A. rupestris (LC50 = 6.67 mg/L air) also possessed fumigant toxicity against L. bostrychophila while the four constituents, 4-terpineol, α-terpineol, α-terpinyl acetate and linalool had LC50 values of 0.34, 1.12, 1.26 and 1.96 mg/L air, respectively. α-Terpinol and α-terpinyl acetate showed strong repellency against L. bostrychophila, while linalool and 4-terpinol exhibited weak repellency. The results indicate that the essential oil of A. rupestris aerial parts and its constituent compounds have potential for development into natural insecticides or fumigants as well as repellents for control of insects in stored grains.

Phenolic compounds and antioxidant activities of Liriope muscari.

Five phenolic compounds, namely N-trans-coumaroyltyramine (1), N-trans-feruloyltyramine (2), N-trans-feruloyloctopamine (3), 5,7-dihydroxy-8-methoxyflavone (4) and (3S)3,5,4′-trihydroxy-7-methoxy-6-methylhomoisoflavanone (5), were isolated from the fibrous roots of Liriope muscari (Liliaceae). Compounds 2–5 were isolated for the first time from the Liriope genus. Their in vitro antioxidant activities were assessed by the DPPH and ABTS scavenging methods with microplate assays. The structure-activity relationships of compounds 1–3 are discussed.

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 (LC50 = 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 LC50 value of 258.11 μg/mL.

Toxicity of the essential oil of Illicium difengpi stem bark and its constituent compounds towards two grain storage insects

Abstract During our screening program for new agrochemicals from Chinese medicinal herbs, the essential oil of Illicium difengpi stem bark was found to possess strong insecticidal activities against the maize weevil, Sitophilus zeamais (Motschulsky) (Coleoptera: Curculionidae) and red flour beetle, Tribolium castaneum Herbst (Coleoptera: Tenebrionidae). A total of 37 components of the essential oil of I. difengpi were identified. The main components of the essential oil were safrole (23.61%), linalool (12.93%), and germacrene D (5.35%). Bioactivities-directed chromatographic separation on repeated silica gel columns led to the isolation of two compounds: safrole and linalool. Safrole showed pronounced contact toxicity against both insect species and (LD50 = 8.54 for S. zeamais; 4.67 µg/adult for T. castaneum) and was more toxic than linalool (LD50 = 24.88 for S. zeamais; 8.12 µg/adult for T. castaneum). The essential oil acting against the two species of insects showed LD50 values of 13.83 and 6.33 µg/adult, respectively. Linalool also possessed strong fumigant toxicity against both insect species (LC50 = 10.02 for S. zeamais; 9.34 mg/L for T. castaneum) and was more toxic than safrole (LD50 = 32.96 and 38.25 mg/L), while the crude essential oil acting against the two species of insects showed LC50 values of 14.62 and 16.22 mg/L, respectively. These results suggest that the essential oil of I. difengpi stem bark and the two compounds may be used in grain storage to combat insect pests.During our screening program for new agrochemicals from Chinese medicinal herbs, the essential oil of Illicium difengpi stem bark was found to possess strong insecticidal activities against the maize weevil, Sitophilus zeamais (Motschulsky) (Coleoptera: Curculionidae) and red flour beetle, Tribolium castaneum Herbst (Coleoptera: Tenebrionidae). A total of 37 components of the essential oil of I. difengpi were identified. The main components of the essential oil were safrole (23.61%), linalool (12.93%), and germacrene D (5.35%). Bioactivities-directed chromatographic separation on repeated silica gel columns led to the isolation of two compounds: safrole and linalool. Safrole showed pronounced contact toxicity against both insect species and (LD₅₀ = 8.54 for S. zeamais; 4.67 µg/adult for T. castaneum) and was more toxic than linalool (LD₅₀ = 24.88 for S. zeamais; 8.12 µg/adult for T. castaneum). The essential oil acting against the two species of insects showed LD₅₀ values of 13.83 and 6.33 µg/adult, respectively. Linalool also possessed strong fumigant toxicity against both insect species (LC₅₀ = 10.02 for S. zeamais; 9.34 mg/L for T. castaneum) and was more toxic than safrole (LD₅₀ = 32.96 and 38.25 mg/L), while the crude essential oil acting against the two species of insects showed LC₅₀ values of 14.62 and 16.22 mg/L, respectively. These results suggest that the essential oil of I. difengpi stem bark and the two compounds may be used in grain storage to combat insect pests.

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 μg/adult) and was more toxic than either 1,4-cineole or nerolidol (LD50 = 50.86 μg/adult and 29.30 μg/adult, respectively) against the maize weevils, while the crude essential oil had a LD50 value of 11.67 μg/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.

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.