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。     

Isocoumarins from the fermentation products of a plant entophytic fungus Penicillium oxalicum

Three new isocoumarins, terrecoumarins A–C (1–3), together with six known isocoumarins (4–9) were isolated from the fermentation products of the fungus Penicillium oxalicum 0403. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. The anti-tobacco mosaic virus (anti-TMV) activities of 1–9 were evaluated. The results revealed that compound 1 showed high anti-TMV activity with inhibition rate 25.4 ± 3.5%. Other compounds also showed weak activity with inhibition rate in the range of 11.3–18.9%.     

海洋来源真菌草酸青霉(Penicillium oxalicum)次级代谢产物的分离与鉴定

目的研究海洋来源真菌草酸青霉(Penicillium oxalicum)的次级代谢产物。方法采用重结晶、硅胶柱色谱、Sephadex LH-20柱色谱、开放ODS柱色谱等方法进行分离纯化;根据理化性质及光谱数据确定化合物的结构。结果分离得到10个化合物,分别鉴定为N-acetyl-hydrazinobenzoic acid(1)、N-[2-cis-(4-hydroxyphenyl)ethenyl]formamide(2)、p-hydroxyphenylacetamide(3)、penipanoid A(4)、penipanoid C(5)、2-(4-hydroxybenzyl)quinazolin-4(3H)-one(6)、oxaline(7)、meleagrin(8)、(3R,4R)-3,4,8-trihydroxy-3,4-dihydro-1(2H)-naphthalenone(9)和(3R,4R)-3,4,6,8-tetrahydroxy-3,4-dihydro-1(2H)-naphthalenone(10)。结论化合物1为新天然产物,化合物9、10为首次从青霉属真菌中分离得到。     

北极真菌Penicillium sp.MYA5次级代谢产物研究

目的 对来源于北极斯瓦尔巴德群岛的真菌Penicillium sp. MYA5的次级代谢产物进行研究。方法 对菌株进行规模发酵,采用正相硅胶、反相ODS、高效液相等色谱方法对发酵液的乙酸乙酯萃取部位进行系统分离纯化,通过核磁共振谱（NMR）、质谱（MS）旋光、ECD等波谱分析方法,并与相关文献比较,鉴定化合物结构。结果 分离得到7个化合物,经鉴定化合物1~7分别为penicophenone C (1),communol G (2),1-(2,4-dihydroxy-5-methylphenyl)ethan-1-one (3),penicophenone A (4), conidiogenones C (5), cis-3,4-dihydro-3, 4, 8-trihydroxynaphthalen-1(2H)-one (6),(-) - (S)-3-hydroxy-3-methyloxindole (7)。结论 化合物1是为新化合物,是已知化合物 (Z)-6-acetyl-3-(1,2-dihydroxypropylidene)-5-hydroxy-8-methylchroman-2-one的同分异构体,我们也首次确定了该已知化合物的绝对构型;化合物3、7为首次从Penicillium 属中获得;其中,化合物5对HL-60以及BEL-7402有着很强的细胞毒活性,IC50值分别为0.04 μM和1.16 μM。     

荚果蕨植物内生真菌Penicillium sp. SYP-F-7610的抑菌活性次级代谢产物研究

摘要：目的 研究荚果蕨根茎内生真菌Penicillium sp. SYP-F-7610发酵液中抑菌活性次级代谢产物。方法 采用硅胶柱 色谱、ODS柱色谱、反相半制备HPLC等分离菌株发酵液中的次级代谢产物,根据比旋光度和波谱学数据(MS、1H NMR、13C NMR)进行结构鉴定。采用比浊法测试次级代谢产物的抑菌活性。结果 从荚果蕨根茎内生真菌Penicillium sp. SYP-F-7610发 酵液中分离鉴定了7个化合物,分别为青霉酸(1)、3,5,6-三甲基-2,4-二羟基苯甲酸甲酯(2)、苔黑酚(3)、4-羟基苯乙酸甲酯(4)、 6-hydroxy-5-methoxy-3-methyl-3,6-dihydro-2H-pyran-4-carboxylic acid (5)、chermesinone A (6)和(R)-甲羟戊酸内酯(7)。化合物1 对大肠埃希菌(Escherichia coli CMCC44103)、乙型副伤寒沙门菌(Salmonela paratyphi B CMCC50094)、蜡样芽胞杆菌(Bacillus cereus ATCC14579)和肺炎克雷伯菌(Klebsiella pneumoniae CMCC46117)表现出抑制作用,IC50值为3.19~6.79 μg/mL。结论 本文 首次对荚果蕨属植物的内生真菌进行研究,发现荚果蕨根茎内生真菌Penicillium sp. SYP-F-7610的次级代谢产物结构类型丰富、 生物活性多样,值得深入研究。化合物5为首次报道从青霉属真菌次级代谢产物中分离得到。化合物1为首次报道对乙型副伤寒 沙门菌具有抑制活性。     

一株药用红树内生真菌Talaromyces flavus TGGP34次级代谢产物及其活性研究

目的 研究1株药用红树老鼠簕（Acanthus ilicifolius L.）来源内生真菌篮状菌属的Talaromyces flavus TGGP34的次级代谢产物及其抗菌活性。方法 利用正、反相硅胶柱层析、Sephadex LH-20凝胶柱层析、半制备高效液相色谱（HPLC）等色谱分离方法,对TGGP34发酵产物的乙酸乙酯粗浸膏进行系统分离纯化;利用核磁共振波谱（NMR）、质谱（MS）等方法并结合文献报道数据确定化合物结构,并对其抗菌活性进行测定。结果 从内生真菌T. flavus TGGP34中分离得到9个化合物,包括4个甾醇类化合物β-sitosterol（1）、24-methylcholesta-7,22-diene-3β,5α,6β-triol（2）、3β,15β-dihydroxyl-(22E,24R)-ergosta-5,8(14),22-trien-7-one（3）、ganodermaside B（4）,3个内酯类化合物dehydroisopenicillide（5）、penicillide（6）、purpactin A（7）,2个二酮哌嗪类化合物cyclo-(S-Pro-R-Val)（8）和cyclo-(L-Pro-L-Leu)（9）,其中化合物3对3株致病菌金黄色葡萄球菌（Staphylococcus aureus）、表皮葡萄球菌（Staphylococcus epidermidis）和白色念珠菌（Candida albicans）表现出明显的抑制活性,其MIC值分别为12.5、12.5和6.25 μg/mL。结论 化合物1～4为首次从篮状菌属（Talaromyces sp.）中分离得到;化合物3具有显著的抗菌活性,具有重要的研究和潜在开发价值。     

Nigerasperones A approximately C, new monomeric and dimeric naphtho-gamma-pyrones from a marine alga-derived endophytic fungus Aspergillus niger EN-13

Three new naphtho-gamma-pyrones, 5-hydroxy-6,8-dimethoxy-2-hydroxymethyl-4H-naphtho[2,3-b]pyran-4-one (1, nigerasperone A), 3,3'-dihydro-2,2',5,5'-tetrahy-droxy-8,8',10,10'- tetramethoxy-2,2'-dimethyl-(6',9-bi-4H-naphtho[1,2-b]pyran)-4,4'-dione (2, nigerasperone B), and 3'-hydro-2',5,5',8-tetrahydroxy-6,6',8'-trimethoxy-2,2'-dimethyl-(7,10'-bi-4H-naphtho[2,3-b]pyran)-4,4'-dione (3, nigerasperone C), together with nine related known compounds were characterized from Aspergillus niger EN-13, an endophytic fungus isolated from the marine brown alga Colpomenia sinuosa. Their structures were elucidated by detailed analysis of spectroscopic data and by comparison with literature reports. In the cytotoxic assay, these compounds did not show remarkable inhibitory effects against A549 and SMMC-7721 tumor cell lines. However, 3 and several known compounds showed weak antifungal activity against Candida albicans and moderate activity on DPPH scavenging.     

草酸青霉菌HSY-P-17次级代谢产物的分离与鉴定

目的研究草酸青霉菌(Penicillium oxalicum)HSY-P-17的次级代谢产物,以期得到有抗肿瘤活性的先导化合物。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、开放ODS柱色谱及HPLC等方法进行分离纯化,通过理化性质和波谱手段分析确定化合物的化学结构。结果从草酸青霉菌HSY-P-17的乙酸乙酯萃取物中分离得到8个化合物,分别鉴定为:3-羟基异斯科勒酮(3-hydroxyisosclerone,1)、4-羟基-小柱孢酮(4-hydroxyscytalone,2)、2-乙酰基-3,5-二羟基苯乙酸甲酯(methyl 2-acetyl-3,5-dihydroxyphenylacetate,3)、大黄酚(chrysophanol,4)、7-羟基-2-(2-羟基丙基)-5-甲基色原酮[7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone,5]、2-(4-羟基苯基)喹唑啉-4(3H)-酮[2-(4-hydroxybenzyl)quinazolin-4(3H)-one,6]、环(脯-缬)二肽[cyclo-(Pro-Val),7]和环(脯-甘)二肽[cyclo-(Pro-Gly),8]。结论化合物1⁸均为首次从草酸青霉菌HSY-P-17次级代谢产物中分离得到。     

一株红树内生真菌Penicillium sp. JY246次级代谢产物及其活性研究

目的 研究一株红树角果木来源内生真菌Penicillium sp. JY246的次级代谢产物及其生物活性。方法 利用硅胶柱层析、Sephadex LH-20凝胶柱层析、半制备HPLC等方法,对该菌发酵产物的乙酸乙酯浸膏进行分离纯化;利用NMR、MS等波谱解析方法以及与文献数据对照,鉴定化合物的结构;通过抗菌和抗虫活性模型对化合物的生物活性进行评价。结果 从内生真菌Penicillium sp. JY246中分离得到12个化合物,分别为7-hydroxy-2-(2-hydroxypropyl)-5-methylchromone (1),(2′S)-2-(propan-2′-ol)-5-hydroxy-benzopyran-4-one (2),2, 3-dihydro-5-hydroxy-2(S)-methyl-4H-1-benzopyran-4-one (3),(11S)-diaprothin (4),questin (5),4-hydroxy-3-prenylbenzoic acid (6),4-methoxy-6-styryl-pyran-2-one (7),(R) 4-hydroxy-2-oxo-1-pyrrolidineacetamide (8),p-hydroxy-benzaldehyde (9),4-hydroxyacetophenone (10),apocynin (11)和1-(2,6-dihydroxyphenyl) ethan-1-one (12)。结论 从内生真菌Penicillium sp. JY246的次级代谢产物中分离得到12个单体化合物,并对所有化合物进行抗菌和抗虫活性测试。结果表明,化合物1, 2, 4和5显示抗细菌活性;化合物4, 5和8对棉铃虫幼虫显示了生长抑制活性。     

Marine natural products sourced from marine-derived Penicillium fungi

Marine micro-organisms have been proven to be a major source of marine natural products (MNPs) in recent years, in which filamentous fungi are a vital source of bioactive natural products for their large metagenomes and more complex genetic backgrounds. This review highlights the 390 new MNPs from marine-derived Penicillium fungi during 1991 to 2014. These new MNPs are categorized based on the environment sources of the fungal hosts and their bioactivities are summarized.     

Xylarodons A and B,new hexaketides from the endophytic fungus Xylaria sp. SC1440

Two new hexaketides, xylarodons B (1) and C (2), were isolated from solid cultures of the endophytic fungus Xylaria sp. SC1440. The structures of these compounds were elucidated on the basis of detailed 1D, 2D NMR, and HRESIMS analysis. Their absolute configurations were established by experimental and TDDFT calculated ECD spectra. The isolated compounds were evaluated for cytotoxic and tyrosinase inhibitory activity.     

海洋来源青霉菌Penicillium polonicum H92次级代谢产物的研究

目的 对源自福建漳江口红树林底部海水沉积物的青霉菌Penicillium polonicum H92的次级代谢产物进行化学成分和生物活性研究.方法 综合利用有机溶剂萃取、硅胶柱色谱、反相硅胶(ODS)柱色谱、凝胶(Sephadex LH-20)柱色谱、薄层色谱、半制备高效液相色谱等多种手段对青霉菌Penicillium...     

Two new compounds from the broth of the marine fungus Penicillium griseofulvum Y19-07

Two new compounds, 4-hydroxyphenethyl methyl succinate (1) and 4-hydroxyphenethyl 2-(4-hydroxyphenyl)acetate (2), were isolated from the EtOAc extract of the broth of the marine fungus Penicillium griseofulvum Y19-07. Five known compounds were also obtained in this study. The structures of the new compounds were elucidated by 1D and 2D NMR spectroscopy and mass spectrometry. All of the isolates were evaluated for their scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl free radical by spectroscopic assays. Also, in the cytotoxicity assay of the two new compounds against HL-60 and PC-3 prostate cancer cell lines, compound 2 showed potential activity with an IC₅₀ value of 64.5 μM against human HL-60 cancer cells.     

A new chloro-monoterpene from the mangrove endophytic fungus Tryblidiopycnis sp. (4275)

A new chloro-monoterpene (compound 1) and three known compounds, peroxyergosterol, uracil and methylisocoumarin, were isolated from the ethyl acetate extract of the fermentation broth of the mangrove endophytic fungus Tryblidiopycnis sp. (4275) obtained from Kandelia woody tissue from Mai Po, Hong Kong. Its structure was determined spectroscopically and by X-ray crystallographic analysis.     

南极真菌Penicillium sp. S-2-10次级代谢产物的研究

目的 对来源于南极海域海底沉积物（47.09° W,62.05° S,水深1393 m）真菌Penicillium sp. S-2-10的次级代谢产物进行研究。方法 对菌株进行规模发酵,并对所得发酵液的乙酸乙酯萃取浸膏进行系统分离纯化,据化学指征和生物学活性两方面特点,采用Sephadex LH 20凝胶色谱、正相硅胶柱色谱、反相ODS柱色谱、高效液相柱层析等色谱分析方法,通过核磁（1H-NMR和13C-NMR等）及质谱（MS）等波谱分析方法,并与相关文献比较,鉴定化合物结构。 结果 分离得到7个单体化合物,经鉴定化合物1~7分别为Benzoic acid, 2-(2,6-dihydroxybenzoyl)-3-hydroxy-5-(hydroxymethyl)-methyl, methyl ester (1), chrysophanol (2), Volemolide (3), Ergosta-6,8(14),22-trien-3-ol (4), 2-aminophenoxazin-3-one (5), 2-benzothiazolol (6), benzoic acid (7)。结论 化合物3,4为首次从Penicillium属真菌中获得。     

南极真菌Penicillium sp. S-3-88次级代谢产物的研究

目的 对源于南极(44.42° W,60.54° S,水深239 m,水温-1.16 ℃)海参体内共附生真菌Penicillium sp. S-3-88的次级代谢产物进行研究。方法 采用Sephadex LH-20色谱、反相ODS柱色谱、高效液相柱层析等色谱分析方法,对Penicillium sp. S-3-88发酵液的乙酸乙酯萃取部位进行系统分离,并通过₁H和₁₃C NMR及质谱(LC-MS)等现代波谱解析手段,并与相关文献比对,鉴定化合物结构。结果 分离得到9个单体化合物。结论 鉴定化合物 1 – 9 分别为2-acetyl-4(3H)-quinazolin--one(1), benzo[d]thiazol-2(3H)-one(2), Octadecyl phenylpropanoate(3), diisobutyl phthalate(4), butyl-isobutyl-phthalate(BIP)(5), ergosterol peroxide(6), melithasterol B(7),22E,24R-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol(8)和cerevisterol(9)。     

A new chloro-monoterpene from the mangrove endophytic fungus Tryblidiopycnis sp. (4275)

A new chloro-monoterpene (compound 1) and three known compounds, peroxyergosterol, uracil and methylisocoumarin, were isolated from the ethyl acetate extract of the fermentation broth of the mangrove endophytic fungus Tryblidiopycnis sp. (4275) obtained from Kandelia woody tissue from Mai Po, Hong Kong. Its structure was determined spectroscopically and by X-ray crystallographic analysis.     

Metabolites from endophytic fungus A12 of Dracaena cambodiana

A new drimane sesquiterpene, 1α,7α-dihydroxyconfertifolin (1), along with two known compounds 2 and 3, was isolated from endophytic fungus A12 of Dracaena cambodiana. The new compound was elucidated by HR-ESI-MS and spectroscopic techniques (IR, UV, 1D, and 2D NMR). Compound 2 showed inhibitory bacterial activity against Staphylococcus aureus with diameter of the inhibition zone of 13.5 mm.     

海绵共附生真菌Penicillium janthinellum的次生代谢产物研究

目的 研究海绵共附生真菌Penicillium janthinellum LZDX-32-1中的活性次生代谢产物。方法 利用硅胶、半制备HPLC等色谱学方法对菌株发酵提取物进行分离纯化,利用UV、NMR、MS等波谱学分析及文献数据比对确定了化合物的结构,采用MTT法检测了化合物的人肿瘤细胞毒性。结果 分离鉴定了5个化合物,分别为okaramines H（1）、okaramines J（2）、fumitremorgin B（3）、verruculogen（4）、paspaline（5）。细胞毒活性测试发现在浓度为10μM条件下,化合物5对A549、HCT-8和MCF-7三种细胞具有一定细胞毒活性（抑制率分别为70.45%、67.03%和88.54%）。结论 从海绵共附生真菌P. janthinellum LZDX-32-1中分离鉴定了5个生物碱类化合物,其中化合物1-4为首次从该种真菌中分离得到,化合物5具有肿瘤细胞毒性。     

A new cerebroside, Asperiamide A, from the marine fungus Asperillus sp

A new cerebroside, asperiamide A (1), and adenosine were produced from a marine fungus, identified as Asperillus sp., collected in the Mei Zhou Gulf, China. Two-dimensional NMR methods, FAB-MS, were used to established the structure of the new compound.