Antimicrobial metabolites from the plant endophytic fungus Penicillium sp.

被引：33

作者：

Yang, Ming-Hua ^{[1
]}

Li, Tian-Xiao ^{[1
]}

Wang, Ying ^{[1
]}

Liu, Rui-Huan ^{[1
]}

Luo, Jun ^{[1
]}

Kong, Ling-Yi ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Nat Med Chem, State Key Lab Nat Med, 24 Tong Jia Xiang, Nanjing 210009, Jiangsu, Peoples R China

来源：

FITOTERAPIA | 2017年 / 116卷

基金：

中国国家自然科学基金;

关键词：

Penicillium sp; Phenolic metabolites; Dichlorine; Antimicrobial; ABSOLUTE-CONFIGURATION; A-C; POLYKETIDES;

D O I：

10.1016/j.fitote.2016.11.008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Five rare dichloro aromatic polyketides (1-5) were obtained from an endophytic fungus Penicillium sp., along with five known metabolites (6-10). Their structures were elucidated by extensive spectroscopic analysis, Mosher methods, as well as [Rh-2(OCOCF3)(4)]-induced electronic circular dichroism (ECD) experiments. Compounds 2-4 and 6 structurally involved acyclic 1.3-diols, the uneasy configuration determinations of which were well carried out by double-derivation NMR methods. Compounds 1-10 were evaluated for their antibacterial and antifungal activities against five strains of human pathogenic microorganisms. Helvolic acid (7) showed potent inhibitory effects against Staphylococcus aureus and Pseudomonas aeruginosa with MIC (minimum inhibitory concentration) values of 5.8 and 4.6 mu g/mL, respectively. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：72 / 76

页数：5

共 20 条

[1] Citromycetins and bilains A-C:: New aromatic polyketides and diketopiperazines from Australian marine-derived and terrestrial Penicillium spp. [J].

Capon, Robert J. ;

Stewart, Michael ;

Ratnayake, Ranjala ;

Lacey, Ernest ;

Gill, Jennifer H. .

JOURNAL OF NATURAL PRODUCTS, 2007, 70 (11) :1746-1752

[2] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[3] Determining the absolute stereochemistry of secondary/secondary diols by 1H NMR:: Basis and applications [J].

Freire, F ;

Seco, JM ;

Quiñoá, E ;

Riguera, R .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3778-3790

[4] [Rh2(OCOCF3)4] as an auxiliary chromophore in chiroptical studies on steroidal alcohols [J].

Frelek, J ;

Szczepek, WJ .

TETRAHEDRON-ASYMMETRY, 1999, 10 (08) :1507-1520

[5]

Fujimoto H, 1996, CHEM PHARM BULL, V44, P1843, DOI 10.1248/cpb.44.1843

[6] Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp. [J].

Ge, Hui Ming ;

Shen, Yao ;

Zhu, Chun Hua ;

Tan, Shu Hua ;

Ding, Hui ;

Song, Yong Chun ;

Tan, Ren Xiang .

PHYTOCHEMISTRY, 2008, 69 (02) :571-576

[7] CIRCULAR-DICHROISM .93. DETERMINATION OF THE ABSOLUTE-CONFIGURATION OF ALCOHOLS, OLEFINS, EPOXIDES, AND ETHERS FROM THE CD OF THEIR INSITU COMPLEXES WITH [RH2(O2CCF3)4] [J].

GERARDS, M ;

SNATZKE, G .

TETRAHEDRON-ASYMMETRY, 1990, 1 (04) :221-236

[8] New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities [J].

He, Jun ;

Shen, Yi ;

Jiang, Jian-Shuang ;

Yang, Ya-Nan ;

Feng, Zi-Ming ;

Zhang, Pei-Cheng ;

Yuan, Shao-Peng ;

Hou, Qi .

CARBOHYDRATE RESEARCH, 2011, 346 (13) :1903-1908

[9] Penicolinates A-E from endophytic Penicillium sp BCC16054 [J].

Intaraudom, Chakapong ;

Boonyuen, Nattawut ;

Suvannakad, Rapheephat ;

Rachtawee, Pranee ;

Pittayakhajonwut, Pattama .

TETRAHEDRON LETTERS, 2013, 54 (08) :744-748

[10]

LAI S, 1991, HETEROCYCLES, V32, P297

← 1 2 →