Chemical composition and insecticidal activity of the essential oil of Artemisia eriopoda against maize weevil, Sitophilus zeamais

In our screening program for new agrochemicals from local wild plants, Artemisia eriopoda was found to possess insecticidal activities against the maize weevil, Sitophilus zeamais. The essential oil of the aerial parts of A. eriopoda was obtained by hydrodistillation and investigated by GC and GC-MS. The main components of the essential oil are germacrene D (21.6%) and eucalyptol (14.2%). The essential oil possesses fumigant toxicity against S. zeamais adults with a LC50 value of 11.5 mg/L air and also shows contact toxicity against S. zeamais adults with a LD50 value of 24.8 microg/adult, respectively.     

Anti-Escherichia coli activity of extracts from Schinus terebinthifolius fruits and leaves

Ethanol extracts obtained from Schinus terebinthifolius Raddi fruits and leaves were active against Escherichia coli with MIC of 78 μg mL^?1 for both extracts. Phytochemical analyses revealed a major presence of phenolic acids, tannins, fatty acids and acid triterpenes in the leaves and phenolic acids, fatty acids, acid triterpenes and biflavonoids in the fruits. Major compounds isolated from the plant, such as the acid triterpene schinol, the phenolic acid derivative ethyl gallate and the biflavonoids agathisflavone and tetrahydroamentoflavone, showed very little activity against E. coli. Bioautography of the ethanol extracts on silica gel plate showed inhibition zones for E. coli. They were removed from the plate and the compounds identified as a mixture of myristic, pentadecanoic, palmitic, heptadecanoic, stearic, nonadecanoic, eicosanoic, heneicosanoic and behenic fatty acids.     

Podophyllotoxin-derived insecticidal agents: part XIII--evaluation of insecticidal activity of podophyllotoxin derivatives against Brontispa longissima

In an attempt to find the biorational insecticides for Brontispa longissima control, 12 podophyllotoxin (PPT) analogues were tested for their insecticidal activity against the fifth-instar larvae of B. longissima in vivo for the first time. Among all the tested compounds, especially compounds 6 and 8 showed more promising and pronounced insecticidal activity than toosendanin, a commercial insecticide derived from Melia azedarach. The different insecticidal activity range of compounds 1-12 indicated that the variation of chemical structures in the PPT skeleton markedly affected the activity profiles of this compound class, and some important structure-activity relationship information has been revealed. Together, these preliminary results may be useful in guiding further modification of PPTs in the development of potential new insecticides.     

Comparative Study of Bioactivity and Safety Evaluation of Ethanolic Extracts of Zanthoxylum schinifolium Fruit and Pericarp

The fruit and pericarp of Zanthoxylum schinifolium (ZS) have been used in traditional medicine; however, few studies have characterized ZS fruit and pericarp. Therefore, in the present study, we evaluated the safety of ZS fruit (ZSF) and pericarp (ZSP) extracts and compared their bioactivity. To evaluate the safety of ZSF and ZSP, mutagenicity, cytotoxicity, and oxidative stress assays were performed and nontoxic concentration ranges were obtained. ZSP was found to be superior to ZSF in terms of its antimutagenic, antioxidant, and anti-inflammatory activities. In the S9 mix, the mutation inhibition rate of ZSP was close to 100% at concentrations exceeding 625 µg·plate⁻¹ for both the TA98 and TA100 strains. ZSP exhibited efficient DPPH (IC₅₀ = 75.6 ± 6.1 µg·mL⁻¹) and ABTS (IC₅₀ = 57.4 ± 6 µg·mL⁻¹) scavenging activities. ZSP inhibited the release of cytokines, involved in IL-1β (IC₅₀ = 134.4 ± 7.8), IL-6 (IC₅₀ = 262.8 ± 11.2), and TNF-α (IC₅₀ = 223.8 ± 5.8). These results indicate that ZSP contains a higher amount of biochemicals than ZSF, or that ZSP contains unique biochemicals. In conclusion, for certain physiological activities, the use of ZSP alone may be more beneficial than the combined use of ZSF and ZSP.     

四川汉源花椒化学成分的研究

四川汉源花椒历史悠久、享誉全国,它具有浓郁的香、麻味,是川菜的重要调味品.以前对它的香、麻味的化学成分很少研究.为科学地开发花椒系列产品,制订产品质量检验方法,本文用GC-MS对汉源花椒的化学成分进行了研究[1],初步确认了香、麻味的主要成分,研究花椒及制品在储藏中的化学成分变化,为改进花椒产品质量和储存产品提供依据.     

Components and antioxidant activity of fruits of Cirsium palustre and C. rivulare

In the hexane extract of C. palustre and C. rivulare fruits, fatty acids, sterols, triterpenes, and volatile compounds were analyzed by the GC-MS-FID method. In the methanolic extracts, total phenol content was estimated. The antioxidant activity of both extracts was measured with DPPH assay and expressed in % scavenged DPPH.     

2-甲基-5-异丙基苯酚对蚕豆蚜的毒杀活性研究

采用生物活性追踪法,以石油醚为溶剂对瑞香狼毒根粉中活性成分进行提取,得到的粗提物经硅胶柱多次柱层析后得到一种纯天然产物,经紫外光谱、红外光谱、质谱和核磁共振谱鉴定为2-甲基-5-异丙基苯酚(香芹酚)。以高效杀虫剂吡虫啉为阳性对照,对该化合物的杀虫活性进行了测定。结果表明,香芹酚对蚕豆蚜有较好的毒杀活性,处理24 h后的致死中浓度(LC50)为16.8 mg.L-1。本项研究将为新型植物源农药的研究和开发奠定较好的基础。     

Efficient quantification of the phenolic profiles of Zanthoxylum bungeanum leaves and correlation between chromatographic fingerprint and antioxidant activity

Sixteen subsequent fractions were prepared from the ethyl acetate fraction of Zanthoxylum bungeanum leaves after bio-guided chromatographic separation. The HPLC profiles and antioxidant activity of the various fractions indicated that the content of eight phenolic compounds (chlorogenic acid, epicatechin, rutin, hyperoside, trifolin, quercitrin, afzelin and quercetin) and antioxidant activity vary significantly, and high concentrations of a combination of eight phenolic compounds would result in an increase of the antioxidant activity. These results suggested that the eight compounds could be used as chemical markers for quality assessment of Z. bungeanum leaves. Correlation between chromatographic fingerprint and antioxidant activity of the fractions showed that quercitrin and hyperoside play crucial roles in the antioxidant activity, and they can be seen as the milestone for quality control. The findings also suggested that five obtained fractions (E-3-3, E-2-4, E-7, E-5 and E-4) could become useful supplements for functional food ingredients and health-related products.     

Components of cottonplant leaves, their functional role and biological activity

This review generalizes information on the composition of the components of cottonplant leaves: hydrocarbons, organic, amino, and hydroxy acids, alcohols, triterpenes, phenolic compounds, carotenoids, sugars, pectin substances, polyisoprenoids, diols, tocopherols, sterol esters, and others. Their role in the growth and development of the plant and their biological properties are discussed.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 40 64 75. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 773–788, November–December, 1997.     

Chemical composition and larvicidal activity of Zanthoxylum armatum against diamondback moth,Plutella xylostella

The diamondback moth, Plutella xylostella (L.) (Lepidoptera: Yponomeutidae) is the most serious pest of cruciferous crops grown in the world causing economic yield loss. Several synthetic insecticides have been used against P. xylostella but satisfactory control was not achieved due to development of resistance to insecticides. Therefore, the present study was carried out to screen different fractions of Zanthoxylum armatum for their insecticidal activities against second instar larvae of P. xylostella. Results indicate, all the fractions showed activity to P. xylostella. However, n-hexane fraction of Z. armatum showed maximum larvicidal activity with minimum LC₅₀ value of 2988.6 ppm followed by ethanol (LC₅₀ = 12779.7 ppm) and methanol fraction (LC₅₀ = 12908.8 ppm) whereas chloroform fraction was least toxic (LC₅₀ = 16750.6 ppm). The GC–MS analysis of n-hexane fraction of leaf extract showed maximum larvicidal activity, which may be due to two major compounds i.e. 2-undecanone (19.75%) and 2-tridecanone (11.76%).     

Synthesis and insecticidal activity of novel 4beta-halogenated benzoylamino podophyllotoxins against Pieris rapae Linnaeus

Twelve new 4beta-halogenated benzoylamino compounds (7.1-7.12) of podophyllotoxin have been synthesized, and their structures were confirmed by IR, 1H-NMR, MS spectra as well as CHN elemental analysis. These compounds showed delayed insecticidal activity against 5th instar larvae of Pieris rapae Linnaeus in vivo, when tested by a leaf-dipping method at a concentration of 250ppm. By preliminary qualitative structure-activity relationship analysis, we found the following results: 1) Compounds 7.2, 7.5-7.9 were more potent than the nature parent product in the mortality after 15 d against P. rapae in vivo. Especially compounds 7.5 and 7.6 bearing meta- and para-chlorobenzene substituents respectively, were the most potent of these compounds; 2) Substitution on the benzene ring moiety of 4beta-benzoylamino podophyllotoxin (PPT) with Cl, Br, I at the para or at the meta position yielded compounds which were as potent or more potent than those containing the corresponding substituting group at the ortho position. 3) Substitution on the benzene ring moiety of 4beta-benzoylamino podophyllotoxin with I either at the ortho, meta or para position yielded less potent compounds (7.10-7.12) when compared with PPT.     

Tetracyclic triterpenoids from the leaves of Azadirachta indica and their insecticidal activities

A new tetranortriterpenoid, meliatetraolenone [24,25,26,27-tetranor-apotirucalla-(apoeupha)-6alpha-O-methyl, 7alpha-senecioyl(7-deacetyl)-11alpha,12alpha,21,23-tetrahydroxy-21,23-epoxy-2,14,20(22)-trien-1,16-dione] (1) was isolated from the methanolic extract of fresh leaves of Azadirachta indica along with the known compound odoratone (3) which was hitherto unreported from this source. Their structures have been elucidated by spectral studies including 2D NMR. The insecticidal activities of 1 as well as those of odoratone (3) are reported. 1 and odoratone both showed mortality on fourth instar larvae of mosquitoes (Anopheles stephensi) with LC(50) values of 16 and 154 ppm, respectively.     

New chemical constituents from the fruits of Zanthoxylum armatum and its in vitro anti-inflammatory profile

Chemical investigations on the fruits of Zanthoxylum armatum Roxb. (Rutaceae) led to the isolation of two new constituents characterised as 2α-methyl-2β-ethylene-3β-isopropyl-cyclohexan-1β, 3α-diol (1) and phenol-O-β-D-arabinopyranosyl-4′-(3″, 7″, 11″, 15″-tetramethyl)-hexadecan-1″-oate (2) along with known compounds m-methoxy palmityloxy benzene (3), acetyl phenyl acetate (4), linoleiyl-O-α-D-xylopyranoside (5), m-hydroxyphenoxy benzene (6) and palmitic acid (7). The chemical structures were established with the help of physical, chemical and spectroscopic methods. The anti-inflammatory potential of isolated compounds 1 and 2 was evaluated using in vitro target-based anti-inflammatory activity in LPS-stimulated primary peritoneal macrophages isolated from mice. Production of pro-inflammatory cytokines (TNF-α and IL-6) was significantly inhibited by the treatment of isolated compounds 1 and 2 in a dose-dependent manner.     

Synthesis and photoactivated insecticidal activity of tetraethynylsilanes

A series of tetraethynylsilanes (TETS) have been synthesized by reaction of silicon tetrachloride (SiCl₄) with Ar–CCLi, which was prepared in situ by treatment of Ar–CCH with n-BuLi. For these TETS thus prepared, their photoactivated insecticidal activities against the 4th-instar larvae of Aedes albopictus (Skuse) were evaluated to enrich the structure–activity relationship. In particular, compound 8 exhibited excellent photoactivated insecticidal activity, the LC₅₀ value was 0.1346 mg L^?1 under UV light treatment and the irradiation-generated enhancement in the activity was more than 69.58-fold, thus could be exploitable as ideal analog candidates in the search for new photoactivated insecticide leads.     

Components of the leaves of Haplophyllum ramosissimum

Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 284, March–April, 1990.     

Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils derived from Artemisia giraldii and Artemisia subdigitata

The aim of this research was to determine the chemical composition and insecticidal activity of the essential oils derived from flowering aerial parts of Artemisia giraldii Pamp. and A. subdigitata Mattf. (Family: Asteraceae) against the maize weevil (Sitophilus zeamais Motsch.). Essential oils of aerial parts of A. giraldii and A. subdigitata were obtained from hydrodistillation and investigated by GC and GC-MS. A total of 48 and 33 components of the essential oils of A. giraldii and A. subdigitata were identified, respectively. The principal compounds in A. giraldii essential oil were β-pinene (13.18%), iso-elemicin (10.08%), germacrene D (5.68%), 4-terpineol (5.43%) and (Z)-β-ocimene (5.06%). 1,8-Cineole (12.26%) and α-curcumene (10.77%) were the two main components of the essential oil of A. subdigitata, followed by β-pinene (7.38%), borneol (6.23%) and eugenol (5.87%). The essential oils of A. giraldii and A. subdigitata possessed fumigant toxicity against the maize weevils with LC50 values of 6.29 and 17.01 mg/L air, respectively. The two essential oils of A. giraldii and A. subdigitata also exhibited contact toxicity against S. zeamais adults with LD50 values of 40.51 and 76.34 μg/adult, respectively. The results indicated that the two essential oils show potential in terms of fumigant and contact toxicity against grain storage insects.