Antifungal metabolites from fungal endophytes of Pinus strobus

The extracts of five foliar fungal endophytes isolated from Pinus strobus (eastern white pine) that showed antifungal activity in disc diffusion assays were selected for further study. From these strains, the aliphatic polyketide compound 1 and three related sesquiterpenes 2-4 were isolated and characterized. Compound 2 is reported for the first time as a natural product and the E/Z conformational isomers 3 and 4 were hitherto unknown. Additionally, the three known macrolides; pyrenophorol (5), dihydropyrenophorin (6), and pyrenophorin (7) were isolated and identified. Their structures were elucidated by spectroscopic analyses including 2D NMR, HRMS and by comparison to literature data where available. The isolated compounds 1, 2, and 5 were antifungal against both the rust Microbotryum violaceum and Saccharomyces cerevisae.     

Ribosomal DNA haplotype distribution of Bursaphelenchus xylophilus in Kyushu and Okinawa islands, Japan

Ribosomal DNA region sequences (partial 18S, 28S and complete ITS1, 5.8S, and ITS2) of the pinewood nematode (Bursaphelenchus xylophilus) were obtained from DNA extracted directly from wood pieces collected from wilted pine trees throughout the Kyushu and Okinawa islands, Japan. Either a 2569bp or 2573bp sequence was obtained from 88 of 143 samples. Together with the 45 rDNA sequences of pinewood nematode isolates previously reported, there were eight single nucleotide polymorphisms and two indels of two bases. Based on these mutations, nine haplotypes were estimated. The haplotype frequencies differed among regions in Kyushu island (northwest, northeast and center, southeast, and southwest), and the distribution was consistent with the invasion and spreading routes of the pinewood nematode previously estimated from past records of pine wilt and wood importation. There was no significant difference in haplotype frequencies among the collection sites on Okinawa island.     

Nematicidal Activity of Plant Essential Oils and Components From Ajowan (Trachyspermum ammi), Allspice (Pimenta dioica) and Litsea (Litsea cubeba) Essential Oils Against Pine Wood Nematode (Bursaphelenchus Xylophilus)

Commercial plant essential oils from 26 plant species were tested for their nematicidal activities against the pinewood nematode, Bursaphelenchus xylophilus. Good nematicidal activity against B. xylophilus was achieved with essential oils of ajowan (Trachyspermum ammi), allspice (Pimenta dioica) and litsea (Litsea cubeba). Analysis by gas chromatography-mass spectrometry led to identification of 12, 6 and 16 major compounds from ajowan, allspice and litsea oils, respectively. These compounds from three plant essential oils were tested individually for their nematicidal activities against the pinewood nematode. LC₅₀ values of geranial, isoeugenol, methyl isoeugenol, eugenol, methyl eugenol and neral against pine wood nematodes were 0.120, 0.200, 0.210, 0.480, 0.517 and 0.525 mg/ml, respectively. The essential oils described herein merit further study as potential nematicides against the pinewood nematode.     

南海链霉菌SCSIO 1635中抗霉素类化合物的分离鉴定(英文)

我们从南海海底沉积环境分离了一株放线菌SCSIO1635,经16S rDNA的序列分析将该株菌鉴定为链霉菌属。我们从该菌的发酵液中分离得到了4个化合物,经质谱和核磁共振波谱解析,确定为抗霉素类化合物:异构体antimycin A1a和A1b(1)、deisovalerylblastmycin(2)、kitamycin A(3)和antimycin A9(4)。     

A soluble acetylcholinesterase provides chemical defense against xenobiotics in the pinewood nematode

The pinewood nematode genome encodes at least three distinct acetylcholinesterases (AChEs). To understand physiological roles of the three pinewood nematode AChEs (BxACE-1, BxACE-2, and BxACE-3), BxACE-3 in particular, their tissue distribution and inhibition profiles were investigated. Immunohistochemistry revealed that BxACE-1 and BxACE-2 were distributed in neuronal tissues. In contrast, BxACE-3 was detected from some specific tissues and extracted without the aid of detergent, suggesting its soluble nature unlike BxACE-1 and BxACE-2. When present together, BxAChE3 significantly reduced the inhibition of BxACE-1 and BxACE-2 by cholinesterase inhibitors. Knockdown of BxACE-3 by RNA interference significantly increased the toxicity of three nematicidal compounds, supporting the protective role of BxACE-3 against chemicals. In summary, BxACE-3 appears to have a non-neuronal function of chemical defense whereas both BxACE-1 and BxACE-2 have classical neuronal function of synaptic transmission.     

Bioactive monoterpene glycosides conjugated with gallic acid from the leaves of Eucalyptus globulus

Two monoterpene glycosides, conjugated with gallic acid [globulusin A (1) and B (2)], together with four known compounds, cypellocarpin A (3), eucaglobulin (4), cuniloside (5) and (1S, 2S, 4R)-trans-2-hydroxy-1,8-cineole beta-d-glucopyranoside (6), were isolated from hot-water extracts of the leaves of Eucalyptus globulus. The structures of compounds 1 and 2 were determined by 1D, 2D NMR and MS spectroscopic analyses. The absolute stereochemistry of 1 was determined by correlating the spectroscopic data with those of synthetic compound 6 with a known configuration. Globulusin A (1) and B (2), cypellocarpin A (3) and eucaglobulin (4), scavenged DPPH free radicals and globulusin A (1) showed a higher antioxidant activity than the other tested compounds, with an IC50 of 3.8microM. Globulusin A (1) and eucaglobulin (4) concentration-dependently suppressed inflammatory cytokine production, tumor-necrosis factor-alpha and interleukin-1beta in cultured human myeloma THP-1 cells co-stimulated with phorbol myristate acetate. These compounds also inhibited melanogenesis in cultured murine melanoma B16F1 cells, without any significant cytotoxicity. These results suggested that globulusin A (1) and eucaglobulin (4), which were isolated as antioxidants from E. globulus, also had anti-inflammatory as well as anti-melanogenesis activity.     

Stereumin A-E, sesquiterpenoids from the fungus Stereum sp. CCTCC AF 207024

Five cadinane sesquiterpenoids, named stereumin A (1), B (2), C (3), D (4) and E (5) were isolated from the CHCl(3) extract of the culture broth of the fungal strain CCTCC AF 207024. Based on the sequences at the internal transcribed spacer (ITS) region and partial 28S rDNA, this fungus was identified as a Stereum sp. The structures of the five compounds were elucidated using spectroscopic data from 1D, 2D NMR and HRESIMS experiments, and the structures of 1 and 2 were further confirmed by single-crystal X-ray diffraction analysis. Compounds 1-5 showed nematicidal activities against the nematode Panagrellus redivivus at 400 mg l(-1). Among these five compounds, compounds 3 and 4 killed 84.4% and 94.9% of P. redivivus, respectively in 48 h.     

Guanacastane-type diterpenoids with cytotoxic activity from Coprinus plicatilis

Four new guanacastane-type diterpenoids (1-4), together with the known compound, guanacastepene E (5), were isolated from a basidiomycete of the macro-fungi, Coprinus plicatilis 82. Their structures were elucidated on the basis of extensive spectroscopic analyses, including FT-ICR-MS, UV, IR and 1D and 2D NMR experiments. The in vitro cytotoxic activities of all compounds against the human cancer cell lines HepG2, HeLa, MDA-MB-231, BGC-823, HCT 116, and U2OS were evaluated, only compound 1 exhibited significant cytotoxicities with IC(50) values ranging from 1.2 to 6.0 μM.     

A new kaempferol triglycoside from Fagonia taeckholmiana: cytotoxic activity of its extracts

In addition to apigenin, apigenin 7-O-glucoside, kaempferol 3-O-glucoside, kaempferol 3,7-di-O-rhamnoside, quercetin, and quercetin 3-O-glucoside, the methanolic extract of Fagonia taeckholmiana afforded a new compound identified as kaempferol 3-O-beta-l-arabinopyranosyl-(1-->4)-alpha-l-rhamnopyranoside-7-O-alpha-l-rhamnopyranoside. Identification of the isolated compounds was based on chemical and spectroscopic analyses including UV, FABMS, (1)H, (13)C and 2D NMR, and DEPT. The cytotoxic activities of the compounds against several cancer cell lines were determined.     

Antibacterial metabolites from the Actinomycete <Emphasis Type="Italic">Streptomyces</Emphasis> sp. P294

The Actinomycete strain P294 was isolated from soil and identified as Streptomyces sp. based upon the results of 16S rRNA sequence analysis. Three compounds obtained from the solid fermentation products of this strain have been determined by 1D, 2D NMR and HRMS experiments. These compounds include two new compounds angumycinones C (1) and D (2), and the known compound X-14881 E (3). All compounds were assayed for antibacterial and nematicidal activity. The results showed the three compounds had different degrees of inhibitory activity against several target bacteria but no significant toxicity against the nematode Caenorhabditis elegans.     

A new prenylflavonoid isolated from propolis collected in the Solomon Islands

The new prenylflavonoid, solophenol A (1), together with three known compounds, bonannione A (2), sophoraflavanone A (3) and (2S)-5,7-dihydroxy-4'-methoxy-8-prenylflavanone (4), were isolated from propolis collected from Malaita Island in The Solomon Islands. The structure of each compound was determined by spectroscopic methods, including mass spectrometry and 2D NMR. Compound 1 exhibited potent 2,2-diphenyl-1-picrylhydrazyl radical-scavenging activity.     

A new antifungal briarane diterpenoid from the gorgonian Junceella juncea Pallas

A new 8-hydroxy briarane diterpenoid (compound 1) with antifungal activity was isolated along with known compounds (2-5) from the gorgonian coral Junceellajuncea. On the basis of spectroscopic data (1D and 2D NMR, MS), the structure of the compound 1 was established as (1S,2S,8S,9S,10S,11R,12R,14S,17R)-11,20-epoxy-14-(3-methylbutanoyl)-2,9,12-triacetoxy-8-hydroxybriar-5(16)-en-18,7-olide. Compound 1 exhibited significant activity against fungi (Aspergillus niger, Candida albicans and Penicillium notatum) but the other compounds (2-5) did not exhibit the activity against fungi.     

The chemical constituents of the fungus Stereum sp

Four new compounds, including a sesquiterpene and three aromatic compounds, and a known compound were isolated from a culture broth of the fungus Stereum sp. The novel sesquiterpene was determined to be stereumone A ((+)-2,3,4a,5,6,7,8a,9-octahydro-5-hydroxy-6,6,9-trimethyl-4,8a-epoxynaphtho[2,3-b]furan-8(8H)-one; 1), and the three new aromatic compounds were elucidated as 3,5-dihydroxy-4-(3-methylbut-2-enyl)benzene-1,2-dicarbaldehyde (2), 5,7-dihydroxy-6-(3-methylbut-2-enyl)isobenzofuran-1(3H)-one (3), butyl 2,4-dihydroxy-6-methylbenzoate (4), together with the known compound methyl 2,4-dihydroxy-6-methylbenzoate (5). The structures were established by spectroscopic methods including 2D-NMR techniques. Compounds 2 and 4 showed evident nematicidal activity against nematode Panagrellus redivivus.     

Synthesis and antiamoebic activity of new oxime ether derivatives containing 2-acetylpyridine/2-acetylfuran

Various oxime ether derivatives of 2-acetylpyridine and 2-acetylfuran series have been synthesised. O-Alkylation of the oximes by various alkylaminoethyl halides gave the corresponding oxime ether derivatives. The structures of these compounds were elucidated by UV, IR, 1H NMR, 13C NMR spectroscopic methods and elemental analyses. All the compounds were screened in vitro against the HM1:IMSS strain of Entamoeba histolytica. Based on the 50% inhibitory concentration (IC50) data of the 12 compounds evaluated, two of the 2-acetylpyridine series and two in the 2-acetylfuran series showed better IC50 values in vitro when compared with the standard amoebicidal drug, metronidazole. Moreover, one compound showed the most promising antiamoebic activity (IC50=0.5 microM vs IC50=1.9 microM of metronidazole).     

松墨天牛对寄主树木的产卵选择

在室内采用选择行为方法,研究了松墨天牛Monochamus alternatus对几种松属植物的产卵选择行为。结果表明,松墨天牛对黑松Pinus thunbergii的选择性最强,对马尾松P.massoniana的选择性最弱,二者间差异显著,它们与火炬松P. taeda和湿地松P. elliottii间无明显差异。在黑松和马尾松的被松材线虫危害木与健康木之间,松墨天牛明显选择被害木产卵;具产卵痕枝段和虫粪处理过的枝段,对松墨天牛的产卵有显著抑制作用,松墨天牛明显地选择对照枝段产卵。     

土壤真菌Curvularia affinis HS-FG-196抗肿瘤化学成分的再研究

为对土壤真菌Curvularia affinis HS-FG-196的次级代谢产物及其体外抗肿瘤活性进行进一步研究。实验采用大孔吸附树脂HP-20树脂柱、硅胶柱、凝胶LH-20柱及半制备高效液相色谱柱从Curvularia affinis HS-FG-196的发酵培养物中分离得到六个单体化合物(1～6)。利用~1H NMR、¹³C NMR、~1H-~1H COSY、HMQC、HMBC、IR、UV和MS等波谱分析方法对其进行了结构鉴定,分别是:pyrenocine S (1)、pyrenocine B (2)、pyrenocine E (3)、pyrenocine I (4)、pyrenochaetic acid B (5)和pyrenochaetic acid C (6),其中化合物1是新化合物。对所得单体化合物进行了体外抗肿瘤活性测试,结果显示化合物1、2、3对肿瘤细胞A549、HCT-116、ACHN、K562和HepG2表现出较强的活性。     

The Aroma of Cigar Tobacco

The sugar moiety of isonaringin (I) was confirmed as rutinose using NMR spectral data. Furthermore, the apigenin-7-rhamnoglucoside (IV), derived from compound I was successfully converted to linarin by partial methylation with dimethyl sulfate, indicating that compound IV has the structure of apigenin-7-β-rutinoside. Thus, compound I was identical with narirutin.

The optical rotatory dispersions of narirutin, didymin and neoeriocitrin were measured. The former two compounds have the aglycones of 2 (S) configuration, and in the latter aglycone is racemized.

The, so called, lonicerin distributed in citrus plants was proven to be identical with veronicastroside.     

Flavonoids from Cleistocalyx operculatus

Two flavonoids 3'-formyl-4',6'-dihydroxy-2'-methoxy-5'-methylchalcone and (2S)-8-formyl-5-hydroxy-7-methoxy-6-methylflavanone together with five known compounds, were isolated from the dried buds of Cleistocalyx operculatus. Their structures were determined on the basis of spectroscopic analyses (UV, IR, EIMS, (1)H, (13)C NMR and HMBC).     

三峡库区松材线虫病扩张速度对人为活动的响应

松材线虫病是我国森林重要的检疫性病害,除自然媒介天牛传播,人为因素介导的传播在松材线虫病扩散和蔓延中起着至关重要的作用。选择在我国松材线虫病的重点发生区域三峡库区,研究马尾松林景观格局和以人为活动强度为主要因子的松材线虫病扩散规律,尝试揭示松材线虫病扩散机制。结果显示三峡库区的疫点数在近年有上升趋势,各地区发病率得到一定控制;在疫区和非疫区,马尾松林斑块聚合度最大的是非疫区的大渡口,为98.6406;斑块分离度最大的是非疫区的秭归,为0.9318;方差分析结果显示马尾松林景观格局和松材线虫病之间没有相关性。进一步研究了松材线虫病和人为活动强度的联系,结果显示松材线虫病发病率和地区路网密度、人口总量具有较强的相关性,和地区GDP、货运周转量相关性小。宜昌的松材线虫病发病率和路网密度的相关系数为0.985,和人口总数的相关系数为0.866;重庆的松材线虫病发病率和路网密度相关系数为0.924,和人口总数相关系数为0.999;其次基于路网密度和人口总数,对三峡库区松材线虫病疫情在未来十年进行了预测,结果显示随着路网密度和人口总数的扩增,宜昌松材线虫病也将呈现逐步增大的趋势,R~2值为0.919和0.637;重庆发生趋势一致,R~2值为0.976和0.992。     

Steroidal saponins from Smilax china and their anti-inflammatory activities

Steroidal saponins, 1, 2, 3 and 4, were isolated from the BuOH extract of Smilax china L., along with 13 known compounds, 5-17. Their structures were elucidated on the basis of MS, 1D and 2D NMR spectroscopic analyses and chemical evidence. In the bioassay tests, all compounds showed inhibitory effects on cyclooxygenase-2 enzyme (COX-2) activities at final concentration of 10(-5) M, and only compound 5 showed an inhibitory effect on production of TNFalpha (tumor necrosis factor alpha) in murine peritoneal macrophages at the same concentration.