5'-Hydroxyzearalenol, a new β-resorcylic macrolide from Fusarium sp. 05ABR26

A new β-resorcylic maerolide, 5'-hydroxyzearalenol (1), was isolated from the culture broth of a marine-derived fungus Fusarium sp. 05ABR26. Three known compounds, zearalenone (2), 8'-hydroxyzearalenone (3) and zearalenol (4) were also isolated. The structure and relative stereochemistry of 1 were elucidated on the basis of spectroscopic data and single-crystal X-ray diffraction data. Compound 2 displayed potent inhibitory activity against Pyricularia oryzae with a MIC value of 6.25 μg/mL, while compound 3 was much less active; however, 1 and 4 showed no obvious activity.     

脱乙酰壳多糖抑制真菌生长的构效关系

本研究目标是研究脱乙酰壳多糖的化学结构(乙酰化程度DA和聚合程度DP)与它的抑制真菌生长能力之间的构效关系. 选用了12个分属于3个系列、化学结构相关而又不同的、结构清晰的脱乙酰壳多糖和3种不同的真菌(Fusarium solani, Fusarium graminearum和Ustilago maydis). 通过分别测定每个脱乙酰壳多糖对3种真菌的生长曲线和最低抑制浓度(MIC, minimum inhibitory concentration); 比较各个系列脱乙酰壳多糖的MIC和它的化学结构(DA和DP)之间的关系. 结果显示对同一种真菌, 不同脱乙酰壳多糖的抑制真菌生长曲线形态和MIC是各不相同的; 同样同一脱乙酰壳多糖, 对不同真菌也有其特殊的生长曲线和MIC; 通常随着脱乙酰壳多糖中DA的递增, MIC是增加的, 其抑制真菌的活性是降低的; 在DA相同的条件下, 随着DP的递增, MIC也是增加的, 其抑制真菌的活性是减低的. 所以可以说, 脱乙酰壳多糖抑制真菌生长的能力与其化学结构紧密相关, 在本实验的条件下, 脱乙酰壳多糖分子越小, 分子中的自由氨基越多, 抑制真菌的活性越大.     

The composition and antifungal bioassay of the essential oils of differentBetula species growing in Turkey

FiveBetula species,B. pendula, B. browicziana, B. medwediewii, B. litwinowii, andB. recurvata, were collected from different parts of Turkey. The leaves of these species were hydrodistilled to yield the consequent essential oils. The essential oil compositions were investigated by GC/MS. 14-Hydroxy--caryophyllene was the main constituent in the oil ofB. pendula. 14-Hydroxy-4,5-dihydro--caryophyllene, a new compound, was identified as the main constituent in the oils ofB. browicziana, B. litwinowii, and B. recurvata. In the oil ofB. medwediewii methyl salicylate was the main compound. Various phytopathogenic fungi were studied by the agar tube dilution technique to test the antifungal activities of the essential oils at 400 g/ml concentration. The essential oils showed strong antifungal activity againstCephalosporium aphidicola, Drechslera sorokinianse, Fusarium solani, andRhizoctonia cerealis.Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 126–130, March–April, 2000.     

An improved electrochemiluminescence polymerase chain reaction method for the detection of Fusarium wilts

An improved electrochemiluminescence polymerase chain reaction （ECL-PCR） method was developed and applied to detect Fusarium wilt. Briefly, the internal transcribed spacer （ITS） sequence of Fusarium oxysporumf, sp Cubense （FOC） was amplified by PCR. Two universal fragments, which were complimentary to Ru（bpy）3^2＋ （TBR） labeled probe and Biotin labeled probe, respectively, were connected to the tail of primers so that all the PCR products got universal sequences. Then biotin labeled probes and TBR labeled probes were hybridized with the PCR products at the same time. Through the specific interaction between biotin and streptavidin, the PCR products were captured by streptavidin coated magnetic bead and then detected by ECL assay. The experiment results showed that the healthy banana samples and infected ones can be discriminated by this ECL-PCR method. This improved ECL-PCR approach is useful in Fusarium wilt detection due to its high sensitivity, simplicity and stability.     

Antifungal Evaluation and Molecular Docking Studies of Olea europaea Leaf Extract,Thymus vulgaris and Boswellia carteri Essential Oil as Prospective Fungal Inhibitor Candidates

Background: The present study investigated the antifungal activity and mode of action of four Olea europaea leaf extracts, Thymus vulgaris essential oil (EO), and Boswellia carteri EO against Fusarium oxysporum. Methods: Fusarium oxysporum lactucae was detected with the internal transcribed spacer (ITS) region. The chemical compositions of chloroform and dichloromethane extracts of O. europaea leaves and T. vulgaris EO were analyzed using GC-MS analysis. In addition, a molecular docking analysis was used to identify the expected ligands of these extracts against eleven F. oxysporum proteins. Results: The nucleotide sequence of the F. oxysporum lactucae isolate was deposited in GenBank with Accession No. {"type":"entrez-nucleotide","attrs":{"text":"MT249304.1","term_id":"1824655600","term_text":"MT249304.1"}}MT249304.1. The T. vulgaris EO, chloroform, dichloromethane and ethanol efficiently inhibited the growth at concentrations of 75.5 and 37.75 mg/mL, whereas ethyl acetate, and B. carteri EO did not exhibit antifungal activity. The GC-MS analysis revealed that the major and most vital compounds of the T. vulgaris EO, chloroform, and dichloromethane were thymol, carvacrol, tetratriacontane, and palmitic acid. Moreover, molecular modeling revealed the activity of these compounds against F. oxysporum. Conclusions: Chloroform, dichloromethane and ethanol, olive leaf extract, and T. vulgaris EO showed a strong effect against F. oxysporum. Consequently, this represents an appropriate natural source of biological compounds for use in healthcare. In addition, homology modeling and docking analysis are the best analyses for clarifying the mechanisms of antifungal activity.     

两种葱属植物提取物对香蕉枯萎病菌有抑制作用组分的气相色谱-质谱分析

以葱、韭菜根的石油醚和乙酸乙酯提取物对香蕉枯萎病菌进行了抑菌实验,结果表明:葱茎的石油醚提取液对香蕉枯萎病菌的抑制效果最明显,采用气相色谱-质谱法对葱茎的石油醚提取液进行分析,发现其中含有42.07％的二硫化物和16.29％的噻烷类化合物,推断这2种化学成分可能是抑菌的主要成分.进一步对葱的根、茎、叶和韭菜根的石油醚提...     

Reduction of the Fusarium Mycotoxins: Deoxynivalenol,Nivalenol and Zearalenone by Selected Non-Conventional Yeast Strains in Wheat Grains and Bread

Mycotoxins, toxic secondary metabolites produced by fungi, are important contaminants in food and agricultural industries around the world. These toxins have a multidirectional toxic effect on living organisms, causing damage to the kidneys and liver, and disrupting the functions of the digestive tract and the immune system. In recent years, much attention has been paid to the biological control of pathogens and the mycotoxins they produce. In this study, selected yeasts were used to reduce the occurrence of deoxynivalenol (DON), nivalenol (NIV), and zearalenone (ZEA) produced by Fusarium culmorum, F. graminearum, and F. poae on wheat grain and bread. In a laboratory experiment, an effective reduction in the content of DON, NIV, and ZEA was observed in bread prepared by baking with the addition of an inoculum of the test yeast, ranging from 16.4% to 33.4%, 18.5% to 36.2% and 14.3% to 35.4%, respectively. These results indicate that the selected yeast isolates can be used in practice as efficient mycotoxin decontamination agents in the food industry.     

Structural revision and absolute configuration of lateritin

‘Lateritin’ (1), a morpholine-2,5-dione (depsipeptide), was reinvestigated for its structure and absolute configuration. On the basis of thorough 1D and 2D NMR and mass spectrometrical analyses, the structure of 1 was revised to be identical with beauvericin (8) and confirmed that beauvericin (8) is the trimeric lactone of ‘lateritin’ (1). The absolute configuration was determined by acidic hydrolysis, followed by application of Marfey’s method, menthyl ester derivatization, and GC–MS analysis. In addition, the specific optical rotation values of the hydrolysis products were compared with those of available standards.     

Trichoderma versus Fusarium—Inhibition of Pathogen Growth and Mycotoxin Biosynthesis

This study evaluated the ability of selected strains of Trichoderma viride, T. viridescens, and T. atroviride to inhibit mycelium growth and the biosynthesis of mycotoxins deoxynivalenol (DON), nivalenol (NIV), zearalenone (ZEN), α-(α-ZOL) and β-zearalenol (β-ZOL) by selected strains of Fusarium culmorum and F. cerealis. For this purpose, an in vitro experiment was carried out on solid substrates (PDA and rice). After 5 days of co-culture, it was found that all Trichoderma strains used in the experiment significantly inhibited the growth of Fusarium mycelium. Qualitative assessment of pathogen–antagonist interactions showed that Trichoderma colonized 75% to 100% of the medium surface (depending on the species and strain of the antagonist and the pathogen) and was also able to grow over the mycelium of the pathogen and sporulate. The rate of inhibition of Fusarium mycelium growth by Trichoderma ranged from approximately 24% to 66%. When Fusarium and Trichoderma were co-cultured on rice, Trichoderma strains were found to inhibit DON biosynthesis by about 73% to 98%, NIV by about 87% to 100%, and ZEN by about 12% to 100%, depending on the pathogen and antagonist strain. A glycosylated form of DON was detected in the co-culture of F. culmorum and Trichoderma, whereas it was absent in cultures of the pathogen alone, thus suggesting that Trichoderma is able to glycosylate DON. The results also suggest that a strain of T. viride is able to convert ZEN into its hydroxylated derivative, β-ZOL.     

Rapid LC‐MS‐based metabolomics method to study the Fusarium infection of barley

Ultra high performance liquid chromatography with quadrupole/time‐of‐flight mass spectrometry was applied to evaluate the potential of nontarget metabolomic fingerprinting in order to distinguish Fusarium‐infected and control barley samples. First, the sample extraction and instrumental conditions were optimized to obtain the broadest possible representation of polar/medium‐polar compounds occurring in extracts obtained from barley grain samples. Next, metabolomic fingerprints of extracts obtained from nine barley varieties were acquired under ESI conditions in both positive and negative mode. Each variety of barley was tested in two variants: artificially infected by Fusarium culmorum at the beginning of heading and a control group (no infection). In addition, the dynamics of barley infection development was monitored using this approach. The experimental data were statistically evaluated by principal component analysis, hierarchical clustering analysis, and orthogonal partial least‐squares discriminant analysis. The differentiation of barley in response to F. culmorum infection was feasible using this metabolomics‐based method. Analysis in positive mode provided a higher number of molecular features as compared to that performed under negative mode setting. However, the analysis in negative mode permitted the detection of deoxynivalenol and deoxynivalenol‐3‐glucoside considered as resistance‐indicator metabolites in barley.