Bioactive specialised metabolites from the endophytic fungus Xylaria sp. of Cudrania tricuspidata

被引:4
作者
Song, Jintong [1 ]
Xu, Ke [1 ,2 ]
Liu, Chunyu [1 ]
Wang, Tian [1 ]
Luan, Xiaoyi [1 ]
Zhu, Lihua [1 ]
Chu, Zhaojun [1 ]
Fu, Xiaojie [1 ]
Chang, Wenqiang [1 ]
Wang, Xiaoning [1 ]
Lou, Hongxiang [1 ]
机构
[1] Shandong Univ, Sch Pharmaceut Sci, Dept Nat Prod Chem, Key Lab Chem Biol Minist Educ, 44 West Wenhua Rd, Jinan 250012, Peoples R China
[2] Shandong Univ, Hosp 2, 247 Bei Yuan St, Jinan 250033, Peoples R China
基金
中国国家自然科学基金;
关键词
Xylaria sp; Xylariaceae; Cudrania tricuspidata; Moraceae; 2,5-Diarylcyclopentenones; Pyrone derivatives; Diketopiperazines; Antiproliferative activity; Anti-inflammatory activity; SECONDARY METABOLITES; 2,5-DIKETOPIPERAZINES; CONSTITUENTS;
D O I
10.1016/j.phytochem.2021.113079
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Fourteen undescribed compounds, including five 2,5-diarylcyclopentenones xylariaones A1-B2, seven a-pyrone derivatives xylaripyones A G, one.-pyrone derivative xylaripyone H, one diketopiperazine cyclo-(L-Leu-N=ethyl-L-Glu), and two known diketopiperazines, were isolated from cultures of the endophytic fungus Xylaria sp., which was separated from Cudrania tricuspidata Bureau ex Lavall ' ee. Their structures were determined by analysing extensive spectroscopic data (HRESIMS and NMR) and electronic circular dichroism (ECD) calculations. Furthermore, these compounds were evaluated for potential antiproliferative activity against the human tumour cell lines PC3 and A549, and the results showed that xylaripyone D exhibited moderate inhibitory activity against the proliferation of PC3 cell lines with an IC50 value of 14.75 mu M. Meanwhile, xylariaone A3 and xylaripyone F displayed weak inhibitory effects on NO production in RAW 264.7 murine macrophages with IC50 values of 49.76 and 69.68 mu M, respectively.
引用
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页数:9
相关论文
共 28 条
[1]   Cytochalasins and phytotoxins from the fungus Xylaria obovata [J].
Abate, D ;
Abraham, WR ;
Meyer, H .
PHYTOCHEMISTRY, 1997, 44 (08) :1443-1448
[2]  
ALLEY MC, 1988, CANCER RES, V48, P589
[3]   Bioactivity studies of oxysporone and several derivatives [J].
Andolfi, Anna ;
Maddau, Lucia ;
Linaldeddu, Benedetto T. ;
Scanu, Bruno ;
Cimmino, Alessio ;
Basso, Sara ;
Evidente, Antonio .
PHYTOCHEMISTRY LETTERS, 2014, 10 :40-45
[4]   A new phenolic metabolite, involutone, isolated from the mushroom Paxillus involutus [J].
Antkowiak, R ;
Antkowiak, WZ ;
Banczyk, I ;
Mikolajczyk, L .
CANADIAN JOURNAL OF CHEMISTRY, 2003, 81 (01) :118-124
[5]   Three Redundant Synthetases Secure Redox-Active Pigment Production in the Basidiomycete Paxillus involutus [J].
Braesel, Jana ;
Goetze, Sebastian ;
Shah, Firoz ;
Heine, Daniel ;
Tauber, James ;
Hertweck, Christian ;
Tunlid, Anders ;
Stallforth, Pierre ;
Hoffmeister, Dirk .
CHEMISTRY & BIOLOGY, 2015, 22 (10) :1325-1334
[6]   An In Planta-Expressed Polyketide Synthase Produces (R)-Mellein in the Wheat Pathogen Parastagonospora nodorum [J].
Chooi, Yit-Heng ;
Krill, Christian ;
Barrow, Russell A. ;
Chen, Shasha ;
Trengove, Robert ;
Oliver, Richard P. ;
Solomon, Peter S. .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2015, 81 (01) :177-186
[7]   Diarylcyclopentendione Metabolite Obtained from a Preussia typharum Isolate Procured Using an Unconventional Cultivation Approach [J].
Du, Lin ;
King, Jarrod B. ;
Morrow, Brian H. ;
Shen, Jana K. ;
Miller, Andrew N. ;
Cichewicz, Robert H. .
JOURNAL OF NATURAL PRODUCTS, 2012, 75 (10) :1819-1823
[8]   The absolute configuration of the mushroom metabolites involutin and chamonixin [J].
Feling, R ;
Polborn, K ;
Steglich, W ;
Mühlbacher, J ;
Bringmann, G .
TETRAHEDRON, 2001, 57 (37) :7857-7863
[9]  
Gao C., 2016, JUNWU XUEBAO, V35, P767
[10]   Breaking the Silence: Protein Stabilization Uncovers Silenced Biosynthetic Gene Clusters in the Fungus Aspergillus nidulans [J].
Gerke, Jennifer ;
Bayram, Oezguer ;
Feussner, Kirstin ;
Landesfeind, Manuel ;
Shelest, Ekaterina ;
Feussner, Ivo ;
Braus, Gerhard H. .
APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 2012, 78 (23) :8234-8244