Jun-Tao Feng

Synthesis and antifungal activity of carabrone derivatives.

Nine derivatives 6-14 of carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than 1. Structure-activity relationships (SAR) demonstrated that the γ-lactone was necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1 could significantly affect the antifungal activity.

Design, Synthesis and Fungicidal Activities of Some Novel Pyrazole Derivatives

In order to discover new compounds with good fungicidal activities, 32 pyrazole derivatives were designed and synthesized. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR, and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), and their fungicidal activities against Botrytis cinerea, Rhizoctonia solani Kuhn, Valsa mali Miyabe et Yamada, Thanatephorus cucumeris (Frank) Donk, Fusarium oxysporum (S-chl) f.sp. cucumerinum Owen, and Fusarium graminearum Schw were tested. The bioassay results indicated that most of the derivatives exhibited considerable antifungal activities, especially compound 26 containing a p-trifluoromethyl- phenyl moiety showed the highest activity, with EC50 values of 2.432, 2.182, 1.787, 1.638, 6.986, and 6.043 μg/mL against B. cinerea, R. solani, V. mali, T. cucumeris, F. oxysporum, and F. graminearum, respectively. Moreover, the activities of compounds such as compounds 27–32 were enhanced by introducing isothiocyanate and carboxamide moieties to the 5-position of the pyrazole ring.

Neritinaceramides A–E, New Ceramides from the Marine Bryozoan Bugula neritina Inhabiting South China Sea and Their Cytotoxicity

Five new ceramides, neritinaceramides A (1), B (2), C (3), D (4) and E (5), together with six known ceramides (6–11), two known alkyl glycerylethers (12 and 13) and a known nucleoside (14), were isolated from marine bryozoan Bugula neritina, which inhabits the South China Sea. The structures of the new compounds were elucidated as (2S,3R,3′S,4E,8E,10E)-2-(hexadecanoylamino)-4,8,10-octadecatriene-l,3,3′-triol (1), (2S,3R,2′R,4E,8E,10E)-2-(hexadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (2), (2S,3R,2′R,4E,8E,10E)-2-(octadecanoylamino)-4,8,10-octadecatriene-l,3,2′-triol (3), (2S,3R,3′S,4E,8E)-2-(hexadecanoylamino)-4,8-octadecadiene-l,3,3′-triol (4) and (2S,3R,3′S,4E)-2-(hexadecanoylamino)-4-octadecene-l,3,3′-triol (5) on the basis of extensive spectral analysis and chemical evidences. The characteristic C-3′S hydroxyl group in the fatty acid moiety in compounds 1, 4 and 5, was a novel structural feature of ceramides. The rare 4E,8E,10E-triene structure in the sphingoid base of compounds 1–3, was found from marine bryozoans for the first time. The new ceramides 1–5 were evaluated for their cytotoxicity against HepG2, NCI-H460 and SGC7901 tumor cell lines, and all of them exhibited selective cytotoxicity against HepG2 and SGC7901 cells with a range of IC50 values from 47.3 μM to 58.1 μM. These chemical and cytotoxic studies on the new neritinaceramides A–E (1–5) added to the chemical diversity of B. neritina and expanded our knowledge of the chemical modifications and biological activity of ceramides.

Repellent activity screening of 11 kinds of essential oils against Aedes albopictus Skuse: microcapsule preparation of Herba Schizonepetae oil and repellent bioassay on hand skin

BACKGROUND The main ingredient of most repellents on the market is DEET, an effective compound that has the disadvantages of toxic reactions as well as damaging effects on plastic and synthetic fabric. DEET alternatives are urgently needed. METHODS The repellent activities of 11 kinds of essential oils were tested against Aedes albopictus Skuse by a Y-tube olfactometer. Using essential oils with high repellent activity as core material and gelatin and gum arabic as wall materials, we prepared microcapsules of essential oils and optimized the preparation process. The microcapsule formulation was then subjected to repellent bioassay on hand skin. RESULTS when the dosage of essential oils was 5 µL, the cinnamon oil repellent rate was 87.5% within 10 min and the Herba Schizonepetae oil (HSO) repellent rate was 98.0% within 3 min. Up to 1.5% (w/v) gelatin and 1.5% (w/v) gum arabic (as wall materials), and HSO (as core material) were used to form microcapsules with a 1:1 ratio of core material to wall material. CONCLUSION The ointment preparations effectively protected hand skin exposed to a high-density A. albopictus Skuse rearing cage for 4-5 h. The HSO microcapsule repellent has broad application and development prospects.

Propamidine decreas mitochondrial complex III activity of Botrytis cinerea.

Propamidine, an aromatic diamidine compound, is widely used as an antimicrobial agent. To uncover its mechanism on pathogenetic fungi, Botrytis cinerea as an object was used to investigate effects of propamidine in this paper. The transmission electron microscope results showed that the mitochondrial membranes were collapsed after propamidine treatment, followed that mitochondria were disrupted. Inhibition of whole-cell and mitochondrial respiration by propamidine suggested that Propamidine is most likely an inhibitor of electron transport within Botrytis cinerea mitochondria. Furthermore, the mitochondrial complex III activity were inhibited by propamidine.

New α-Methylene-γ-Butyrolactone Derivatives as Potential Fungicidal Agents: Design, Synthesis and Antifungal Activities

In consideration of the fact that the α-methylene-γ-butyrolactone moiety is a major bio-functional group in the structure of carabrone and possesses some agricultural biological activity, forty-six new ester and six new ether derivatives containing α-methylene-γ-butyrolactone moieties were synthesized, and their fungicidal activities against Colletotrichum lagenarium and Botrytis cinerea were investigated. Most of the synthesized compounds showed moderate to significant fungicidal activity. Among them, halogen atom-containing derivatives showed better activity than others, especially compounds 6a,d which exhibited excellent fungicidal activity against C. lagenarium, with IC50 values of 7.68 and 8.17 μM. The structure-activity relationship (SAR) analysis indicated that ester derivatives with electron-withdrawing groups on the benzene ring showed better fungicidal activity than those with electron-donating groups. A quantitative structure-activity relationship (QSAR) model (R2 = 0.9824, F = 203.01, S2 = 0.0083) was obtained through the heuristic method. The built model revealed a strong correlation of fungicidal activity against C. lagenarium with the molecular structures of these compounds. These results are expected to prove helpful in the design and exploration of low toxicity and high efficiency α-methylene-γ-butyrolactone-based fungicides.

Synthesis and Field Evaluation of the Sex Pheromone Analogues to Soybean Pod Borer Leguminivora glycinivorella

In order to develop efficient lures for soybean pod borer Leguminivora glycinivorella (Matsumura) in China, (E,E)-8,10-dodecadienyl acetate (EE-8,10-12:Ac), the main component of the pheromone of L. glycinivorella, and 12 structurally-related compounds were synthesised in good overall yields, regiospecificities, and stereo-selectivities via coupling reactions catalysed by Li2CuCl4. The effect of different synthetic compounds, alone or in combination with EE-8,10-12:Ac, on numbers of captured L. glycinivorella males was evaluated. EE-8,10-12:Ac, (E)-10-dodecenyl acetate(E-10-12:Ac), (E)-8-dodecenol (E-8-12:OH), tetradecyl acetate (14:Ac), and (Z)-9-tetradecenyl acetate (Z-9-14:Ac) alone displayed different attractiveness to L. glycinivorella males. 14:Ac, E-8-12:OH, E-10-12:Ac, (E,E)-8,10-dodecadienal (EE-8,10-12:Ald), (E)-8-dodecenal (E-8-12:Ald), (E)-10-dodecenal (E-10-12:Ald) and Z-9-14:Ac all showed a synergistic effect to EE-8,10-12:Ac at certain dosages. The binary mixtures of EE-8,10-12:Ac and E-10-12:Ald, Z-9-14:Ac,14:Ac, E-8-12:Ald, EE-8,10-12:Ald, E-8-12:OH, or E-10-12:Ac in suitable ratios give 17.00-, 10.98-, 10.67-, 6.73-, 5.54-, 4.30- and 4.50-fold increases in trap catch, respectively, over the standard pheromone lure, and as novel pheromone blends, demonstrated potential use in pheromone traps to monitor or control L. glycinivorella populations in China.

Bioassay‐guided isolation of potent aphicidal Erythrina alkaloids against Aphis gossypii from the seed of Erythrina crista‐galli L

BACKGROUND The cotton aphid (Aphis gossypii Glover) is one of the most invasive pests of cotton. Many botanical phytochemicals have a long history as a source of insecticides, and as templates for new insecticides. This study was undertaken to isolate aphicidal compounds from the seeds of Erythrina crista-galli L. using the bioassay-guided isolation method. RESULTS Three novel and 11 known Erythrina alkaloids were isolated. Erysodine (9), erysovine (10), erysotrine (8) and erythraline (11) showed moderate to excellent aphicidal activity with LD50 values of 7.48, 6.68, 5.13 and 4.67 ng aphid-1 , respectively. The Potter spray tower bioassay gave corresponding LC50 values of 186.81, 165.35, 163.74 and 112.78 µg ml-1 . A unique substructure, which presents an sp3 methylene at C-8, a non-oxygenated site at N-9 and a conjugated dienes group (Δ1,2 and Δ6,7 ), plays a crucial role in the aphicidal activity. Application of erythraline (11) led to different increases in the activities of superoxide dismutase, catalase and glutathione S-transferase. CONCLUSION The study demonstrated that the Erythrina alkaloids erysodine (9), erysovine (10), erysotrine (8) and erythraline (11) have potential use as botanical aphicides for commercial application, or as templates for the development of new insecticides.

Differential expressed analysis of Tripterygium wilfordii unigenes involved in terpenoid backbone biosynthesis

Abstract Tripterygium wilfordii Hook. f. is the traditional medicinal plants in China. Triptolide, wilforgine, and wilforine are the bioactive compounds in T. wilfordii. In this study, the contents of three metabolites and transcription levels of 21 genes involved in three metabolites biosynthesis in T. wilfordii were examined using high-performance liquid chromatography and reverse transcription PCR after application of methyl jasmonate (MeJA) on hairy roots in time course experiment (3–24 h). The results indicated that application of MeJA inhibited triptolide accumulation and promoted wilforgine and wilforine metabolites biosynthesis. In hairy roots, wilforgine content reached 693.36 μg/g at 6 h after adding MeJA, which was 2.23-fold higher than control. The accumulation of triptolide and wilforine in hairy roots increased the maximum at 9 h, which was 1.3- and 1.6-folds more than the control. Most of the triptolide secretes into the medium, but wilforgine and wilforine cannot secrete into the medium. The expression levels of unigenes which involved terpenoid backbone biosynthesis exist the correlation with marker metabolites (triptolide, wilforgine and wilforine) after induction by MeJA, and can be then used to infer flux bottlenecks in T. wilfordii secondary metabolites accumulation. These results showed that these genes may have potential applications in the metabolic engineering of T. wilfordii metabolites production.

Effects of Portulaca oleracea L. extract on lipid oxidation and color of pork meat during refrigerated storage

The study explored the preservation effect of Portulaca oleracea L. extract (POE) on pork meat under refrigerated conditions for 9 days. POE was tested for antioxidant activity and antibacterial activity in vitro and the results showed that POE has strong antioxidant activity and has antibacterial activity against Pseudomonas aeruginosa, Bacillus subtilis and Bacillus cereus to some extent. Effect of POE in different levels (0.25%, 0.50% and 1.0%) on quality and shelflife of pork meat storage were evaluated. Results showed that the treatments of POE significantly inhibited microbial growth,delayed lipids oxidation, reduced values of thiobarbituric acid reactive substances (TBARS) and total volatile base‑nitrogen (TVB-N), increased superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) activities and in a dose-dependent manner (P < .05). Concomitantly, 1.0%POE and 0.50%POE treatments had better appearance compared with control after 9 days storage. All results confirmed that POE could effectively maintain the quality of chilled pork compared to control.