New Antibacterial Dihydropyrones Induced by Co-Culture of Penicillium crustosum PRB-2 and Penicillium citrinum HDN11-186

Two new dihydropyrones,rhytismatones C(1)and D(2),and a known compound,penicillenol A1(3),were isolated from the co-culture broth of the deep-sea-derived fungus Penicillium crustosum PRB-2 and Suaeda salsa-derived endophytic fungus Peni-cillium citrinum HDN11-186.Their structures were elucidated through comprehensive analysis of nuclear magnetic resonance(NMR)spectra and mass spectra.The absolute configurations of new compounds were determined by calculating the electronic circular di-chroism(ECD)spectrum.UPLC-MS data showed that compounds 1–3 could only be detected in the media of co-culture,suggesting new biosynthetic pathways were activated in the co-cultured fungi.Compound 1 showed obvious antibacterial activities against Pro-teus sp.MMBC-1002 and Bacillus subtilis MMBC-1004 with minimum inhibitory concentration(MIC)both at 25μmolL^(-1).

Comparative proteomics reveals the response and adaptation mechanisms of white Hypsizygus marmoreus against the biological stress caused by Penicillium

White Hypsizygus marmoreus is a popular edible mushroom.Its mycelium is easy to be contaminated by Penicillium,which leads to a decrease in its quality and yield.Penicillium could compete for limited space and nutrients through rapid growth and produce a variety of harmful gases,such as benzene,aldehydes,phenols,etc.,to inhibit the growth of H.marmoreus mycelium.A series of changes occurred in H.marmoreus proteome after contamination when detected by the label-free tandem mass spectrometry(MS/MS)technique.Some proteins with up-regulated expression worked together to participate in some processes,such as the non-toxic transformation of harmful gases,glutathione metabolism,histone modification,nucleotide excision repair,clearing misfolded proteins,and synthesizing glutamine,which were mainly used in response to biological stress.The proteins with down-regulated expression are mainly related to the processes of ribosome function,protein processing,spliceosome,carbon metabolism,glycolysis,and gluconeogenesis.The reduction in the function of these proteins affected the production of the cell components,which might be an adjustment to adapt to growth retardation.This study further enhanced the understanding of the biological stress response and the growth restriction adaptation mechanisms in edible fungi.It also provided a theoretical basis for protein function exploration and edible mushroom food safety research.

滇重楼内生真菌Penicillium chrysogenum次生代谢产物研究

运用多种色谱分离方法对滇重楼内生真菌Penicillium chrysogenum YNCA1212次生代谢产物进行化学成分研究,共分离鉴定了9个化合物,分别为:macrophorin A(1)、macrophorin D(2)、peniginsengin A(3)、dihydrodemethylsorbicillin(4)、2′,3′-dihydrosorbicillin(5)、(2E,4E)-1-(2,6-dihydroxy-3,5-dimethyl-phenyl)hexa-2,4-dien-1-one(6)、(S)-penipratynolene(7)、3,5-dihydroxytoluene(8)、N-(2-hydroxypropanoyl)-2-aminobenzoic acid amide(9),化合物6对金黄色葡萄球菌具有弱的抑菌活性(IC 50=136.7μg/mL).

1株海洋真菌Penicillium sp.的次级代谢产物及抗细菌活性研究

目的研究1株海洋真菌Penicillium sp.LW23的次级代谢产物及其抗细菌活性。方法采用硅胶柱层析、Sephadex LH-20凝胶柱层析及半制备高效液相色谱等方法,对该菌株发酵产物进行分离纯化;通过核磁共振波谱(NMR)和质谱(MS)等方法并比对相关文献,鉴定化合物结构;采用微量肉汤稀释法评价其体外抗菌活性。结果从菌株发酵的乙酸乙酯粗提物中分离鉴定了6个化合物,分别为methyl penicyrone(1)、penicyrone(2)、verrucosidin(3)、deoxyverrucosidin(4)、peniquinone A(5)和penipratynolene(6)。结论海洋真菌Penicilliumsp.LW23能产生具有抗细菌活性的化合物。化合物3和4对幽门螺杆菌Helicobacter pylori G27和三重耐药菌H.pylori BHKS159具有中等抑菌活性;化合物5对野油菜黄单孢菌、青枯雷尔菌、枯草芽胞杆菌和耻垢分枝杆菌均具有一定程度的抑菌活性。

中国南海来源真菌Penicillium sp.SCSIO 40438次级代谢产物研究

本论文对中国南海来源真菌Penicillium sp.SCSIO 40438的次级代谢产物进行了研究。通过硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及高效液相色谱等多种分离方法对该菌株的发酵产物进行了分离纯化,并利用核磁共振和高分辨质谱等波谱学方法对分离得到的化合物进行了结构鉴定。从中共分离鉴定到9个化合物:1-(2-Methylbut-3-en-2-yl)-1H-indole-3-carbaldehyde(1)、1-methyl-2(1H)-quinazolinone(2)、fructigenine A(3)、fructigenine B(4)、2-[(s)-hydroxy(phenyl)methyl]-3-methylquinazolin-4(3H)-one(5)、3-methylviridicatin(6)、3-O-methylviridicatol(7)、viridicatol(8)和(+)-cyclopenol(9)。其中,化合物1和2为新天然产物。抑菌活性实验表明,化合物8具有中等强度的抑制金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌活性,最低抑菌浓度为8.0μg·mL^(-1)。

红榄李来源内生真菌Penicillium oxalicum HLLG-13次级代谢产物与生物活性研究

对一株红树植物红榄李(Lumnitzera littorea (Jacq.) Voigt)内生真菌Penicillium oxalicum HLLG-13次级代谢产物进行系统研究;综合运用多种色谱分离方法结合波谱、光谱技术从中分离鉴定了21个单体化合物,分别为2-(4-羟苯基)乙基-(2S)-羟基丙酸(1),2-(4-羟苯基)乙酸乙酯(2),(4-羟苯基)乙酸甲酯(3),4-羟基苯乙醇(4),2,4,5-三甲基间苯二酚(5),1-(2,6-dihydroxyphenyl) butan-1-one(6),rosmarinosin C(7),penicyclone A(8),penicyclone C(9),2-(N-乙酰氨基)苯酚(10),N-乙酰酪胺(11),2-[[(2S)-羟基-1-氧丙基]氨基]苯甲酰胺(12),peniamidone A(13),meleagrin(14),7-羟基-2-(2’S-羟丙基)-5-甲基色酮(15),3-甲基-6,8-二羟基异香豆素(16),(-)-6-hydroxymellein(17),(3R)-甲基-5-氯-6,8-二羟基-二氢异香豆素(18),(3R)-甲基-6,8-二羟基-7-甲氧基-二氢异香豆素(19),(-)-citreoisocoumarinol(20)和de-O-methyldiaporthin(21)。抗菌活性测试结果表明,所有化合物对测试的5株人体致病菌和3株弧菌均无明显抗菌活性;神经保护活性测试结果表明,化合物16具有中等的神经保护活性,在200μmol/L浓度下,可以将H2O_(2)氧化损伤的HT22细胞存活率由43.36%提升至60.15%。

深海真菌Penicillium sp.Z13次级代谢产物的研究

目的:研究海洋真菌Penicillium sp.Z13次级代谢产物。方法:采用凝胶柱,ods柱,反相高效液相制备色谱法等,对该真菌发酵产物的乙酸乙酯提取物进行分离纯化,采用核磁共振氢谱和碳谱等方法,确定化合物的结构。结果:从海洋真菌Penicillium sp.Z13的乙酸乙酯提取物中分离得到10个化合物,分别鉴定为6-desmethylmonacolin-J-15(1),3,5-dihydroxy-7-(8-hydroxy-2-met-hy-hexahydronaph-thalen-1-yl)heptanoic acid(2)和penicopeptide A(3),圆弧菌素(4)和圆弧菌醇(5),viridicatol(6)和viridicatin(7),吲唑(8),吲哚乙酸(9),环(异亮氨酸-脯氨酸)(10)。结论:海洋真菌Penicillium sp.Z13可以产生结构多样的次级代谢产物。

鲸鱼骨来源真菌Penicillium sp. S2014503化学成分及其生物活性研究

从一块腐烂的鲸鱼骨头分离鉴定了一株真菌Penicillium sp. S2014503。利用大米固体发酵培养技术从该菌产物中获得10个化合物,通过核磁共振波谱数据比对分析结合质谱数据分析,手性化合物测定旋光值或者进行X-射线单晶衍射分析后将这10个化合物分别鉴定为emodin(1)、citreorosein(2)、tetrahydroaltersolanolB(3)、conioxanthoneA(4)、chrysogine(5)、pyramidamycin B (6)、germicidin O (7)、2-(6-hydroxy-5,7-dimethylbenzefuranone-4-yl) acetaldehyde (8)、astrophenone (9)和chenopodolans A (10)。经生物活性测试发现,化合物1和2对藤黄微球菌具有弱的抑制活性,化合物1、2和4对卤虫幼虫具有显著的致死毒性。此外,化合物1是中药大黄和虎杖的主要致泻成分。文章首次报道了来源于海洋动物样品鲸鱼骨的真菌Penicillium sp.能够生产大黄素类等活性天然产物。

Safety evaluation and whole genome sequencing for revealing the ability of Penicillium oxalicum WX-209 to safely and effectively degrade citrus segments

The microbial potential of Penicillium has received critical attention.The present research aimed to elucidate the efficacy of crude enzyme secreted from Penicillium oxalicum WX-209 in degrading citrus segments and evaluate the safety of the process.Results showed that citrus segment membranes gradually dissolved after treatment with the crude enzyme solution,indicating good degradation capability.No significant differences in body weight,food ingestion rate,hematology,blood biochemistry,and weight changes of different organs were found between the enzyme intake and control groups.Serial experiments showed that the crude enzyme had high biological safety.Moreover,the whole genome of P.oxalicum WX-209 was sequenced by PacBio and Illumina platforms.Twenty-five scaffolds were assembled to generate 36 Mbp size of genome sequence comprising 11369 predicted genes modeled with a GC content of 48.33%.A total of 592 genes were annotated to encode enzymes related to carbohydrates,and some degradation enzyme genes were identified in strain P.oxalicum WX-209.

New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti

Two novel compounds including a cyclohelminthol type polyketide(namely oxaleimide K,1)and a maleimide deriva-tive(namely peniroquefortine A,2),and a new natural product(namely 2-(acetylamino)-N-[(1E)-2-phenylethenyl]-acetamide,3),together with four known compounds(4-7),were isolated and identified from fungus Penicillium roqueforti,which was separated from the root soil of Hypericum beanii N.Robson collected from the Shennongjia For-estry District,Hubei Province.Their structures including absolute configurations were mainly established by the NMR spectroscopy analyses and single-crystal X-ray diffraction experiment.Compound 1 represents the second example of a cyclohelminthol type polyketide,which features a rare 6/6/5/5 tetracyclic system and a branched aliphatic chain containing a terminal olefin(oct-1-en-3-yl)moiety,and compound 2 possesses an unprecedented carbon skeleton that is uniquely defined by a maleimide moiety linked to the respective 4-methylene-2-(3-methylbut-2-en-1-yl)-phenol and para-substituted aromatic moieties via the carbon-carbon bonds.Remarkably,the absolute configuration of a cyclohelminthol type polyketide as exemplified by compound 1 is determined by the single-crystal diffraction analysis for the first time,highlighting an E-configuration for the linkage of a succinimide moiety and a tetrahydro-furan moiety for 1 rather than a Z-configuration as previously reported in the biosynthesis study,which gives a new insight into the structural elucidation of this category of polyketides.Additionally,compound 1 exhibited significant cytotoxic activity against multiple tumor cells,especially against the Farage and SU-DHL-2 cells(IC_(50)<20μM,48 h).Further mechanism study revealed that compound 1 significantly induced cell cycle arrest in Farage and SU-DHL-2 cells by causing abnormal ROS level and triggering oxidative stress.

海洋来源青霉Penicillium sp.的化学成分研究

海洋微生物因生存环境特殊,常能形成结构特异、活性良好的代谢产物。本文对1株海洋沉积物中分离得到的青霉Penicillium sp.进行化学成分研究和抗菌活性评价。结果分离和鉴定了4个化合物,分别为Nuatigenin(1)、吲哚-3-乙酸(2)、胸苷(3)和3-苯基乳酸(4),其中化合物1对金黄色葡萄球菌和白色念珠菌均有一定的抑菌活性,化合物4对白色念珠菌抑菌效果良好,其余化合物对不同的菌均无抑制作用。

微紫青霉(Penicillium janthinellum)Snef1650诱导大豆胞囊线虫防治效果及GmCAD应答响应

大豆胞囊线虫严重影响大豆的产量和品质,利用生防菌可以有效控制大豆胞囊线虫(SCN)种群数量并降低危害。微紫青霉(Penicillium janthinellum)Snef1650是本实验室筛选出的对大豆胞囊线虫具有较高防效的生防真菌。为了研究Snef1650诱导大豆抗SCN的生防机制,通过触杀、室内盆栽和裂根试验检测Snef1650菌株诱导SCN防治效果;通过实时荧光定量PCR技术检测了木质素合成关键酶肉桂醇脱氢酶(CAD)在线虫胁迫下的表达变化。结果表明,随着Snef1650浓度(20%、40%、60%、80%和100%)和暴露时间(12、24、36和48 h)的增加,J2死亡率逐渐增加。盆栽和裂根试验发现,Snef1650发酵液有效延缓线虫幼虫的侵染和发育。qPCR分析感病品种Williams 82和抗线虫品种小粒黑豆中GmCAD的表达情况发现,GmCAD1和GmCAD2在Snef1650诱导感病品种抗线虫过程中9 dpi和15 dpi时表达显著上调,同时与抗病品种中的表达情况存在时间一致性。间苯三酚木质素染色表明,Snef1650诱导了木质素参与SCN胁迫,与小粒黑豆中染色结果相似,染色部分更加明显。研究结果表明,SCN胁迫下Snef1650可诱导木质素生物合成来抵御线虫的入侵以及发育。

烟草内生真菌Penicillium janthinellum的代谢表型分析

为了研究烟草内生真菌Penicillium janthinellum的代谢表型特征,本文利用Biolog细胞表型芯片技术,对烟草内生真菌的950种代谢表型进行了测定。结果表明:烟草内生真菌能够代谢101种碳源、304种氮源、8种磷源和1种硫源;能在10%氯化钠、6%氯化钾、5%硫酸钠、20%乙二醇、6%甲酸钠、7%尿素、12%乳酸钠、200 mmol/L磷酸钠、100 mmol/L硝酸钠、100 mmol/L硫酸铵中较好生长;其适应的pH值范围为5~10;当pH值为5.2时,在20~200 mmol/L苯甲酸钠中无法生存。

瘤背石璜来源真菌Penicillium sclerotiorum GZU-XW03-2液体发酵产物的化学成分研究

目的研究瘤背石璜来源真菌Penicillium sclerotiorum GZU-XW03-2液体发酵产物的化学成分。方法运用正相硅胶柱色谱、ODS柱色谱、Sephadex LH-20葡聚糖凝胶柱色谱和半制备液相色谱等色谱分离手段对真菌液体发酵产物进行分离纯化,通过核磁共振波谱(1H-NMR、13C-HMR)、质谱(MS)以及电子圆二色谱(ECD)等技术进行化合物结构鉴定。结果从真菌液体发酵产物中分离得到8个聚酮类化合物,分别鉴定为peniazaphilone J(1)、5-chloroisorotiorin(2)、(+)-sclerotiorin(3)、deacetylsclerotiorin(4)、isochromophiloneⅢ(5)、penazaphilone E(6)、2,4-dihdroxy-6-(5,7-dimethyl-2-oxo-trans-3-trans-5-nonadienyl)-3-methylbenzaldehyde(7)、6-((1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl)-2,4-dihydroxy-3-methylbenzaldehyde(8)。结论化合物(1)为新化合物,其具有罕见的氮-氮键结构,把该化合物命名为peniazaphilone J。化合物(2)~(8)为首次从该真菌中分离得到。

Penicillium sp．脂肪酶的发酵及催化生成生物柴油的研究

目的：为了提高脂肪酶的产量及更好地应用脂肪酶。方法：采用单因子实验与均匀设计相结合的方法,对青霉Penicil- lium sp．TS414发酵生产脂肪酶的条件进行了优化。结果：在实验优化后的最适产酶培养基中,碳源为1．4%蔗糖,氮源为7．0%豆饼粉,起始pH8．0。均匀设计优化后的产酶水平(315．1U/mL)比优化前(101．5U/mL)提高了约2倍。Penicillium sp．TS414脂肪酶能够有效地催化大豆油转酯化合成脂肪酸甲酯(生物柴油),反应72h后,脂肪酸甲酯的最终得率在96%左右。结论：Penicillium sp．TS414产生的脂肪酶在生物柴油的工业化生产方面,具有潜在的应用前景。

黄海葵附生真菌Penicillium thomii的化学成分

目的 研究黄海葵 (anemone)附生真菌Penicilliumthomii的化学成分。方法 用各种色谱技术进行分离纯化 ,根据理化性质和波谱数据进行结构鉴定。结果 从黄海葵附生真菌Penicilliumthomii菌丝体中分离得到 5个化合物 ,分别为青霉酮A(I) ,对甲基苯甲酸 (II) ,1 O 十六碳烷酰 2 O ( 9 十八碳烯酰 ) 3 O ( 9,12 十八碳二烯酰 )甘油酯 (III) ,5α ,8α 环二氧 2 4 ζ 甲基胆甾 6,2 2 二烯 3 β 醇 (IV)和大黄素 (V)。 结论 青霉酮A(I)为新化合物 ,化合物II,III。

南海海洋真菌Penicillium sp. FS60的次级代谢产物研究

目的:研究南海海洋真菌Penicillium sp.FS60的次级代谢产物及其细胞毒活性。方法:采用正相硅胶柱、反相硅胶柱、凝胶柱、HPLC和薄层制备等色谱技术和重结晶对菌株FS60的发酵产物进行分离纯化,并通过波谱分析进行结构鉴定;以神经胶质瘤细胞SF-268、乳腺癌细胞MCF-7、大细胞肺癌细胞NCI-H460为供试细胞株,采用SRB法测试化合物的细胞毒活性,以金黄色葡萄球菌(SA)、大肠杆菌(EC)和铜绿假单胞菌(PA)为指示菌株,采用改良的MMT法测试化合物的抗菌活性。结果:从发酵物中分离并鉴定了7个化合物,分别为:2,4-二羟基-3,5,6三甲基苯甲酸甲酯(1)、对羟基苯乙酮(2)、5-羟甲基糠酸(3)、isochromophilone VIII(4)、麦角甾醇(5)、过氧化麦角甾醇(6)、啤酒甾醇(7)。结论:化合物1为首次从青霉属真菌中分离得到,化合物3具有较强的抗菌活性,化合物4具有显著的胞毒活性。

红树植物内生真菌Penicillium s p.中一个醌类化学成分的研究

利用各种层析手段(反相ODS健合硅胶、葡聚糖凝胶LH-20柱层析等),从红树植物内生真菌Penicil-liumsp.的发酵液中分离纯化了1个醌类化合物,通过各种波谱实验(1D-NMR,2D-NMR以及ESIMS)确定其结构为:5-甲氧基-11,12,18,19-四羟基蒽醌(1)。

黄海葵附生真菌Penicillium sp.化学成分的研究(Ⅰ)

从黄海葵 [Anthopleura xanthogrammica(Berkly) ]附生真菌 Penicillium sp.的发酵液中首次分离到4个化合物 ,分别鉴定为 :对羟基苯乙醇 ( ) ,(Z) N- [2 - (4-羟基苯基 )乙烯基 ]甲酰胺 ( ) ;(E) N- [2 - (4-羟基苯基 )乙烯基 ]甲酰胺 ( ) ,邻苯二甲酸二异丁基酯 ( ) ,其中化合物 ( )为首次从天然界分离得到。它们的化学结构经理化数据和波谱分析 。

一株红树内生真菌Penicillium sp.(ZZF29#)次级代谢产物的分离与鉴定

研究了一株药用红树内生真菌Penicillium sp.(ZZF29#)的次级代谢产物。用硅胶柱层析、制备薄层层析和重结晶等方法,从该菌发酵液的乙酸乙酯相中分离获得8种单体化合物,运用现代波谱技术并与文献数据对照,鉴定其结构分别为:环(苯丙-丙)二肽(1)、环(苯丙-甘)二肽(2)、环(苯丙-苯丙)二肽(3)、环(苯丙-酪)二肽(4)、大黄素(5)、大黄素甲醚(6)、麦角甾醇(7)和过氧化麦角甾醇(8)。