红树林植物海莲内生真菌Penicillium sp.091402化学成分的研究

目的 对红树植物海莲内生真茵茵丝体提取物的乙酸乙酯萃取部分进行化学成分研究.方法 采用硅胶柱色谱等分离手段,利用理化教据和各种波谱分析方法,结合文献对照,对海莲内生真菌penicilium sp.091402菌丝体中化学成分进行分离鉴定.结果与结论 从海莲内生真菌penicilium sp.091402菌丝体乙酸乙酯萃取部分分离得到6个化合物,分别鉴定为:(3β,22E)-麦角甾-5,7,22-三烯-3-醇(1),(313,5α,8α,22E)-5,8-过氧麦角甾-6,22-二烯-3-醇(2),(3β,5α,6α,7α,22E)-5,6-环氧麦角甾-8(14),22-=-烯-3,7-二醇(3),(3β,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇(4),soyasapogenol B(5)和citrinin H2(6).     

红树林真菌草酸青霉(092007)的环二肽类成分

目的研究海南文昌红树林真菌草酸青霉(Penicillium oxalicum)的代谢产物,寻找新的抗肿瘤活性化合物。方法利用硅胶、Sephadex LH-20、ODS柱色谱及制备型高效液相色谱等方法进行分离,通过化合物的理化性质及各种波谱技术鉴定它们的结构,采用MTT法评价化合物体外细胞毒活性。结果从真菌菌丝体的丙酮提取物中分离得到6个环二肽类化合物,鉴定其结构分别为:环(苯丙-异亮)二肽[cyclo-(Phe-Ile)](1)、环(苯丙-缬)二肽[cyclo-(Phe-Val)](2)、环(异亮-亮)二肽[cyclo-(Ile-Leu)](3)、环(缬-缬)二肽[cyclo-(Val-Val)](4)、环(脯-缬)二肽[cyclo-(Pro-Val)](5)、环(脯-甘)二肽[cyclo-(Pro-Gly)](6)。体外活性表明:化合物1、3和5在50μg.mL-1下对肝癌细胞HepG-Ⅱ的抑制率分别为31%、32%、17%,对前列腺癌细胞LNCaP抑制率分别为50%、43%、53%。结论这些化合物均为首次从该属真菌的代谢产物中分离得到,其中化合物2、3和5具有一定的细胞毒活性。     

红树植物老鼠簕内生真菌橘青霉P4-5-1中的1个新异喹啉酮生物碱

目的 研究老鼠簕内生真菌橘青霉(Penicillium citrinum)P4-5-1的化学成分。方法 利用正反相硅胶柱色谱、Sephadex LH-20凝胶柱色谱以及半制备高效液相色谱等技术对P4-5-1次生代谢产物进行分离,利用高分辨质谱、一维及二维核磁共振等波谱鉴定技术确定化合物结构。结果 从P4-5-1大米发酵物中分离得到了6个化合物,分别为4-methoxy-2-methylisoquinolin-1(2H)-one (1)、fischexanthone (2)、penicitrinone A (3)、ent-aspergoterpenin C (4)、sydowiol E (5)和citrinin (6)。结论 化合物1为新异喹啉酮生物碱,命名为citrinadin D;化合物2、4和5首次从该种真菌中获得。     

Paeciloxanthone, a new cytotoxic xanthone from the marine mangrove fungus Paecilomyces sp. (Tree1-7)

The metatrophic fungus Paecilomyces sp. (Tree1-7) was isolated from an estuarine mangrove from the Taiwan Strait. The methanol extract of the fungal mycelium exhibited cytotoxicity against hepG2. Paeciloxanthone (1), a new xanthone, and the known compounds emodin (2) and chrysophanol (3), were isolated from the extract. Their structures were elucidated by spectroscopic experiments. Paeciloxanthone (1) exhibited in vitro cytotoxicity against hepG2 (IC₅₀ = 1.08 μg/mL), acetylcholineesterase (AChE) inhibitory (IC₅₀ = 2.25 μg/mL) and antimicrobial activities.     

Acanthiline A,a pyrido[1,2-a]indole alkaloid from Chinese mangrove Acanthus ilicifolius

Abstract

Chemical investigation of the leaves and stems of the Chinese mangrove Acanthus ilicifolius Linn. led to the isolation and structure elucidation of one new pyrido[1,2-a]indole alkaloid named acanthiline A (1), together with one known compound aurantiamide acetate (2). Compound 1 has a previously unreported natural product skeleton. The structure elucidation of 1 was based on the analysis of its 1D and 2D NMR and mass spectroscopic data.     

基因组信息指导下海参共附生Penicillium sclerotiorum SD-36嗜氮酮类化合物的挖掘

目的 结合生物信息学与分子遗传操作技术深入挖掘海参共附生菌核青霉(Penicillium sclerotiorum)SD-36的活性次级代谢产物,并探析其生物合成基因簇中转录调控因子的作用。方法 基于本课题组前期P. sclerotiorum SD-36的基因组信息,利用antiSMASH预测了一条具有合成嗜氮酮类化合物潜力的双PKS基因簇。针对该簇中一个锌指转录因子PsAza1构建了含潮霉素抗性基因和强启动子pgpdA的转录因子基因过表达盒,转化P. sclerotiorum SD-36原生质体后,经过抗性筛选及PCR验证获得阳性转化子OE::PsAza1。发酵培养后HPLC检测次级代谢产物变化并通过qRT-PCR验证基因簇核心基因的转录水平。结果 OE::PsAza1的多种次级代谢产物产量增加,其中两个化合物通过质谱、核磁数据鉴定为活性嗜氮酮类isochromophilone VI和sclerotiorin C,其产量较野生型分别增加了约6倍和4.5倍。qRT-PCR检测该簇中两个聚酮合酶基因及Psaza1基因的转录水平,显示上调60-80倍。结论 首次明确P. sclerotiorum SD-36的双PKS基因簇编码活性嗜氮酮类化合物,且转录因子PsAza1正向调控该簇核心基因的表达水平及化合物产量。本研究结果为P. sclerotiorum SD-36中化合物isochromophilone VI和sclerotiorin C的生物制备及调控研究奠定理论基础。     

2-Methyl-versiquinazoline C,a new fumiquinazoline-type alkaloid from the fungus Aspergillus flavipes PJ03-11

A new fumiquinazoline-type alkaloid 2-methyl-versiquinazoline C (1), together with six known compounds (2–7), was isolated from Aspergillus flavipes PJ03-11 using OSMAC method. Their structures were elucidated on the basis of extensive spectroscopic analysis, and the absolute configuration of compound 1 was determined by the experimental and calculated ECD data. In addition, the cytotoxic activities against three human cancer cell lines (HL-60, THP-1, and PC-3) were evaluated.