Characterization of Limonoids Isolated from the Fruits of Melia toosendan and Their Antifeedant Activity against Pieris rapae

The fruits of Melia toosendan Sieb . et Zucc . (Meliaceae) are a source of bioactive limonoids that can be used as effective pesticides. In this study, two novel limonoids, 6‐acetylsendanal and 6‐ketocinamodiol, were isolated together with fourteen known compounds, namely four protolimonoids, six trichilin‐class limonoids, and four C‐seco limonoids. The structures of the new compounds were determined by extensive spectroscopic analyses (HR‐ESI‐MS, UV, IR, 1D and 2D NMR). The bioassay results revealed that eleven of the extracted limonoids exhibited interesting antifeedant activities against the larvae of Pieris rapae with AFC₅₀ values in the range of 0.11–1.79 mm . Particularly, mesendanin H, with an AFC₅₀ value of 0.11 mm , exhibited a higher activity than the positive control toosendanin. Information on new bioactive limonoids may provide further insight into M. toosendan as a source of bioactive components.     

竹提取物对棉铃虫幼虫及菜青虫的拒食活性

研究结果表明 ,质量浓度为 1 0g L的 1 0种供试竹提取物对棉Helicoverpaarmigera铃虫均具有较强的拒食作用 ,1 2h拒食率最高达 95 . 0 3 % ,最低为 74. 0 7% ,其中毛金竹 (Phyllostachysnigravar.henonis)、白纹短穗竹 (Brachystachyumalbostriatum)提取物对棉铃虫 3龄幼虫的AFC50 (拒食中浓度 )分别为 2 . 0g L、2. 7g L ,但 2 4h、48h拒食率均明显下降。对菜青虫 3龄pierisrapae幼虫的拒食效果以凤凰竹 (Bambusamultiplex)提取物最好 ,2 4h拒食率为 71. 69% ;对 4龄菜青虫的拒食效果以毛金竹提取物最好 ,拒食率为71 . 45 % ,其中毛金竹、白纹短穗竹 2种竹提取物对菜青虫 3龄幼虫的AFC50 分别为 2 .68g L和 3 . 3 7g L。研究结果对于开发环境友好农药以及充分利用竹类资源均具有重要意义。     

决明子胰蛋白酶抑制剂COTI对菜青虫生长抑制作用的研究

从决明子中分离得到胰蛋白酶抑制剂COTI,利用其缓冲液浸泡油菜叶片饲喂菜青虫(Pieris rapae L)幼虫后,幼虫体重明显下降,分析显示菜青虫中肠提取物中蛋白酶活性受到COTI的抑制,表明决明子胰蛋白酶抑制剂对菜青虫的生长具有明显的抑制作用。     

假臭草对菜青虫杀虫活性的研究

测定了假臭草根、茎、叶的甲醇提取液对菜青虫的生物活性。结果表明假臭草根、茎、叶的甲醇提取液对菜青虫无触杀活性;假臭草提取液对菜青虫的拒食活性强弱依次为叶茎根,在浓度为1 g/mL时拒食率分别为36.51%、63.34%和79.33%;假臭草茎和叶的甲醇提取液对菜青虫有一定的胃毒作用,在浓度为1 g/mL时,假臭草叶和茎甲醇提取液对菜青虫的胃毒活性分别为66.67%和33.33%。     

Cytotoxic Activity and Related Mechanisms of Prenylflavonoids Isolated from Mallotus conspurcatus Croizat

Five prenylflavonoids, 6‐prenylnaringenin ( 1 ), 8‐prenylnaringenin ( 2 ), 7‐O‐methyl‐8‐prenylnaringenin ( 3 ), 7‐O‐methyl‐6‐prenylnaringenin ( 4 ), and 4′‐O‐methyl‐6‐prenylnaringenin ( 5 ), were isolated from the traditional herb Mallotus conspurcatus Croizat (Euphorbiaceae). Compounds 1 – 5 revealed cytotoxic activity against cervical cancer (HeLa) cells with IC₅₀ values ranging from 10.08 to 60.16 μm by MTT method, and interestingly, these prenylflavonoids were less toxic to normal HL‐7702 cells. Furthermore, compounds 1 and 5 could inhibit the c‐myc expression and telomerase activity and cause mitochondrial dysfunction. These findings might contribute to a better understanding of the biological activities of prenylflavonoids and lay the foundation for further studies on the cytotoxic activity of natural products isolated from M. conspurcatus.     

Antifungal Activity of 2,4-Dihydroxyacylophenones and Related Compounds

The antifungal activity of 2,4-dihydroxyacylophenones and related compounds against Trichophyton spp and other fungi were investigated to determine their structure-activity relationships.

The activity of these compounds was found to be closely related to the length of the acyl and alkyl substituents attached to the 1,3-dihydroxybenzene moiety In addition, differences in activity were observed depending on the position of the alkyl substituents and on the number of substituents attached to the 1,3-dihydroxybenzene moiety. Some compounds tested showed potent antifungal activity against Trichophyton spp. and other fungi that was more active than amphotericin B.     

拟青霉菌代谢产物对菜粉蝶幼虫的生物活性

淡紫拟青霉(Paecilomyces lilacinus)甲醇萃取物柱层析活性馏分DM6和拟青霉(Paeecilomyces sp.)菌株X1甲醇萃取物柱层析活性馏分X1M5对菜粉蝶Pieris rapae(L.)4龄幼虫具有较强的选择性和非选择性拒食作用,处理后24h选择性AFC50分别为5.8652mg/mL和3.5239mg/mL,非选择性AFC50分别为9.0095mg/mL和14.0234mg/mL。饲喂法、注射法、点滴法测定结果表明,DM6和X1M5对菜粉蝶4龄幼虫具有较强的毒杀活性,其中注射法处理后72h,DM6和X1M5对菜粉蝶4龄幼虫的LD50分别为0.1846μg/头和0.6784μg/头。DM6和X1M5以5.0mg/mL饲喂法处理菜粉蝶3龄幼虫后,试虫生长发育受到强烈的抑制作用,发育抑制率分别为73.34%和63.30%。这些结果对于进一步研究拟青霉菌杀虫活性成分具有重要参考意义。     

Synthesis and Herbicidal Activity of 6-Phenyl-5-Propylamino-2-Pyrazinecarbonitriles and Related Compounds

6-Phenyl- and 5-phenyl-2-pyrazinecarbonitriles with or without a propylamino group at the 3-, 5- or 6-position of the pyrazine ring were prepared together with some related compounds from the corresponding 2,3-pyrazinedicarbonitriles. Their herbicidal activities against barnyardgrass and broadleaf weeds were examined in pot tests. The 6-phenyl-2-pyrazinecarbonitriles were relatively potent compared with the 5-phenyl derivatives. Moreover, the presence of a propylamino group at the 5-position of the 6-phenyl-2-pyrazinecarbonitriles was closely related to an increase in activity.     

Antiproliferative Activity of Root Extract from Gentian Plant (Gentiana triflora) on Cultured and Implanted Tumor Cells

We describe a novel pharmacological activity of the gentian root, an ingredient of Chinese medicines. Root extract from Gentiana triflora triggered cell death of human Daudi cells in culture. In addition, daily administration of the extract to mice inhibited growth of implanted solid tumors. Extract treatment of cultured cells resulted in the appearance of shranken, fragmented, or condensed cell and nuclear morphologies, and in chromosomal DNA degradation. But, the extract-treated cells did not show DNA fragmentation, which exhibits a nucleosome ladder, suggesting that extract-triggered cell death is not mediated through a typical apoptotic pathway.     

Antifungal Activity and Action Mechanism Study of Coumarins from Cnidium monnieri Fruit and Structurally Related Compounds

The increasing resistance of plant diseases caused by phytopathogenic fungi highlights the need for highly effective and environmentally benign agents. The antifungal activities of Cnidium monnieri fruit extracts and five isolated compounds as well as structurally related coumarins against five plant pathogenic fungi were evaluated. The acetone extract, which contained the highest amount of five coumarins, showed strongest antifungal activity. Among the coumarin compounds, we found that 4-methoxycoumarin exhibited stronger and broader antifungal activity against five phytopathogenic fungi, and was more potent than osthol. Especially, it could significantly inhibit the growth of Rhizoctonia solani mycelium with an EC₅₀ value of 21 μg mL⁻¹. Further studies showed that 4-methoxycoumarin affected the structure and function of peroxisomes, inhibited the β-oxidation of fatty acids, decreased the production of ATP and acetyl coenzyme A, and then accumulated ROS by damaging MMP and the mitochondrial function to cause the cell death of R. solani mycelia. 4-Methoxycoumarin presented antifungal efficacy in a concentration- dependent manner in vivo and could be used to prevent the potato black scurf. This study laid the foundation for the future development of 4-methoxycournamin as an alternative and friendly biofungicide.     

Antiproliferative Activity of Chemically Characterized Propolis from Turkey and Its Mechanisms of Action

The aim of this study was to evaluate the ethanolic extract of propolis originated from northern Turkey for its antiproliferative, apoptotic and cell cycle arrest promoting effects on MCF7, HGC27, A549 cancer cell lines and a healthy cell line (HUVEC) in terms of DNA content, morphological features, expression of cell cycle checkpoint proteins p21, p53, Cyclin D1 and immune checkpoint protein PD‐L1. The extract showed moderate antiproliferative activity against all tested cancer cell lines with IC₅₀ values in the range of 58.6–90.7 μg/mL in MTS assay. Further studies indicated that propolis extract exerted apoptotic effect on cancer cell lines, promoted cell cycle arrest through activation of p21 and resulted in accumulation at G0/G1 phase of cancer cells. Propolis treatment caused increased cell size, according to fluorescent imaging except for MCF7. HPTLC analysis revealed that 3‐O‐methylquercetin, chrysin, caffeic acid, CAPE, galangin and pinocembrin were the main components of the extract. The amounts of caffeic acid and CAPE in the extract were found to be 5.5 and 11.1 mg/g, respectively, by a validated HPLC method. Our study is the first one, revealing effect of propolis on PD‐L1 expression on certain cancer cell lines.     

Deceleration of the cell cycle underpins a switch from proliferative to terminal divisions in plant stomatal lineage

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Chemopreventive and Antioxidant Activity of the Chamazulene‐Rich Essential Oil Obtained from Artemisia arborescens L. Growing on the Isle of La Maddalena,Sardinia, Italy

The essential oils of Artemisia arborescens growing in Sardinia (Italy), collected during three plant growth stages, i.e., from the vegetative stage to post‐blooming time, were characterized. Moreover, the in vitro antiproliferative and antioxidant activities of the oil isolated from aerial parts collected in February were evaluated. The essential oils belonged to the β‐thujone/chamazulene chemotype, notably with the highest amount of chamazulene (ca. 52%) ever detected up to now in the genus Artemisia and, in general, in essential oils. Quantitative variations in the oil composition were observed as the plant passes from the vegetative to the blooming stage. The oil was tested for its potential tumor cell growth‐inhibitory effect on T98G, MDA‐MB 435S, A375, and HCT116 human cell lines, using the MTT (=3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyl‐2H‐tetrazolium bromide) assay. The highest activity was observed on A375 and HCT116 cell lines, with IC₅₀ values of 14 μg/ml. Moreover, the in vitro antioxidant and free radical‐scavenging assays revealed the oil to be an effective scavenger of the ABTS radical cation, with an activity comparable to that of Trolox^®. These results support the use of A. arborescens oil for the treatment of inflamed skin conditions. Finally, the composition of the polar fraction of the A. arborescens aerial parts was also examined, and the main component detected was 5‐O‐caffeoylquinic acid, which was identified for the first time in this plant.     

Chemical Diversity and Antimicrobial Activity of Volatile Compounds from Zanthoxylum zanthoxyloides Lam. according to Compound Classes,Plant Organs and Senegalese Sample Locations

The chemical diversity of Zanthoxylum zanthoxyloides growing wild in Senegal was studied according to volatile compound classes, plant organs and sample locations. The composition of fruit essential oil was investigated using an original targeted approach based on the combination of gas chromatography (GC) and liquid chromatography (LC) both coupled with mass spectrometry (MS). The volatile composition of Z. zanthoxyloides fruits exhibited relative high amounts of hydrocarbon monoterpenes (24.3 – 55.8%) and non‐terpenic oxygenated compounds (34.5 – 63.1%). The main components were (E)‐β‐ocimene (12.1 – 39%), octyl acetate (11.6 – 21.8%) and decanol (9.7 – 15.4%). The GC and GC/MS profiling of fruit essential oils showed a chemical variability according to geographical locations of plant material. The LC/MS/MS analysis of fruit oils allowed the detection of seven coumarins in trace content. The chemical composition of fruit essential oils was compared with volatile fractions of leaves and barks (root and trunk) from the same plant station. Hexadecanoic acid, germacrene D and decanal were identified as the major constituents of leaves whereas the barks (root and trunk) were dominated by pellitorine (85.8% and 57%, respectively), an atypic linear compound with amide group. The fruit essential oil exhibited interesting antimicrobial activities against Staphylococcus aureus and Candida albicans, particularly the alcohol fraction of the oil.