Antioxidant CPA-type indole alkaloids produced from the deep-sea derived fungusAspergillussp. SCSIO 41024

被引:12
作者
Chen, Wei-Hao [1 ,2 ]
Li, Kun-Long [1 ,2 ]
Lin, Xiu-Ping [1 ]
Liao, Sheng-Rong [1 ]
Yang, Bin [1 ]
Zhou, Xue-Feng [1 ]
Wang, Jun-Jian [3 ]
Liu, Yong-Hong [1 ,2 ]
Wang, Jun-Feng [1 ]
机构
[1] Chinese Acad Sci, South China Sea Inst Oceanol, Guangdong Key Lab Marine Mat Med, CAS Key Lab Trop Marine Bioresources & Ecol, Guangzhou, Peoples R China
[2] Univ Chinese Acad Sci, Beijing, Peoples R China
[3] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou, Peoples R China
基金
中国国家自然科学基金;
关键词
Deep-sea derived; Aspergillus; indole alkaloid; cyclopiazonic acid; antioxidative activity; CYCLOPIAZONIC ACID; OXINDOLE ALKALOIDS; SPERADINE;
D O I
10.1080/14786419.2020.1749614
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Twelve indole alkaloids, including alpha-cyclopiazonic acid (CPA) (1), nine 2-oxo indole CPA derivatives (2-10), and two open-ring indole CPA derivatives (11and12), were isolated from the fermentation broth of a deep-sea derived fungusAspergillussp. SCSIO 41024. Their structures and absolute configurations were elucidated mainly by using extensive NMR spectroscopic, mass spectrometric and single crystal X-ray diffraction analysis. To the best of our knowledge, the crystallographic data of3and7were firstly reported, and the absolute configuration of3was confirmed for the first time by the single crystal X-ray diffraction analysis. Most isolated compounds were tested for their antimicrobial, antitumor and radical scavenging activities. In addition, compounds1,2and11showed moderate antioxidative activity against DPPH with IC(50)values of 190.1, 31.9, 228.4 mu g/mL, respectively.
引用
收藏
页码:5266 / 5270
页数:5
相关论文
共 19 条
  • [1] Asymmetric total synthesis of the indole alkaloid cyclopiazonic acid and first structure activity data
    Beyer, W. R. Christian
    Woithe, Katharina
    Lueke, Bettina
    Schindler, Michael
    Antonicek, Horst
    Scherkenbeck, Juergen
    [J]. TETRAHEDRON, 2011, 67 (17) : 3062 - 3070
  • [2] Two new aromatic polyketides from a deep-sea fungus Penicillium sp. SCSIO 06720
    Guo, Cui
    Lin, Xiu-Ping
    Liao, Sheng-Rong
    Yang, Bin
    Zhou, Xue-Feng
    Yang, Xian-Wen
    Tian, Xin-Peng
    Wang, Jun-Feng
    Liu, Yong-Hong
    [J]. NATURAL PRODUCT RESEARCH, 2020, 34 (09) : 1197 - 1205
  • [3] ISOLATION AND STRUCTURE OF CYCLOPIAZONIC ACID A TOXIC METABOLITE OF PENICILLIUM CYCLOPIUM WESTLING
    HOLZAPFE.CW
    [J]. TETRAHEDRON, 1968, 24 (05) : 2101 - &
  • [4] BIOSYNTHESIS OF CYCLOPIAZONIC ACID
    HOLZAPFE.CW
    [J]. PHYTOCHEMISTRY, 1971, 10 (02) : 351 - &
  • [5] CYCLOPIAMIDE, AN ISOINDOLO[4,6-CD]INDOLE FROM PENICILLIUM-CYCLOPIUM
    HOLZAPFEL, CW
    BREDENKAMP, MW
    SNYMAN, RM
    BOEYENS, JCA
    ALLEN, CC
    [J]. PHYTOCHEMISTRY, 1990, 29 (02) : 639 - 642
  • [6] Speradines F-H, Three New Oxindole Alkaloids from the Marine-Derived Fungus Aspergillus oryzae
    Hu, Xiao
    Xia, Qi-Wen
    Zhao, Yang-Yang
    Zheng, Qiu-Hong
    Liu, Qin-Ying
    Chen, Li
    Zhang, Qi-Qing
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2014, 62 (09) : 942 - 946
  • [7] SPERADINES B-E, FOUR NOVEL TETRACYCLIC OXINDOLE ALKALOIDS FROM THE MARINE-DERIVED FUNGUS ASPERGILLUS ORYZAE
    Hu, Xiao
    Xia, Qi-Wen
    Zhao, Yang-Yang
    Zheng, Qiu-Hong
    Liu, Qin-Ying
    Chen, Li
    Zhang, Qi-Qing
    [J]. HETEROCYCLES, 2014, 89 (07) : 1662 - 1669
  • [8] Cytotoxicity and immunotoxicity of cyclopiazonic acid on human cells
    Hymery, Nolwenn
    Masson, Floriane
    Barbier, Georges
    Coton, Emmanuel
    [J]. TOXICOLOGY IN VITRO, 2014, 28 (05) : 940 - 947
  • [9] HALOTHANE AND CYCLOPIAZONIC ACID MODULATE CA-ATPASE OLIGOMERIC STATE AND FUNCTION IN SARCOPLASMIC-RETICULUM
    KARON, BS
    MAHANEY, JE
    THOMAS, DD
    [J]. BIOCHEMISTRY, 1994, 33 (46) : 13928 - 13937
  • [10] Diketopiperazine-Type Alkaloids from a Deep-Sea-Derived Aspergillus puniceus Fungus and Their Effects on Liver X Receptor α
    Liang, Xiao
    Zhang, Xuelian
    Lu, Xinhua
    Zheng, Zhihui
    Ma, Xuan
    Qi, Shuhua
    [J]. JOURNAL OF NATURAL PRODUCTS, 2019, 82 (06): : 1558 - 1564