Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (4): 1229-1234.DOI: 10.6023/cjoc202110038 Previous Articles     Next Articles


Malfilamentoside A的构型确定与新呋喃糖苷类化合物Malfilamentoside D

徐慧欣a,b, 王璐a,b, 张丽萍a,c, 刘威a,c, 张庆波a,c, 张海波a,c, 张长生a,b,c,d, 张文军a,b,c,*()   

  1. a 中国科学院南海海洋研究所 热带海洋生物资源与生态实验室 广东海洋药物重点实验室 广州 510301
    b 中国科学院大学 北京 100049
    c 广东南方海洋科学与工程实验室 广州 511458
    d 中国科学院南海海洋研究所 三亚中科海洋研究院 海南三亚 572000
  • 收稿日期:2021-10-26 修回日期:2021-11-25 发布日期:2021-12-30
  • 通讯作者: 张文军
  • 基金资助:
    国家自然科学基金(41676165); 国家自然科学基金(41911530078); 国家自然科学基金(41606193)

Configurational Assignment of Malfilamentoside A and a New Furanone Glycoside Malfilamentoside D

Huixin Xua,b, Lu Wanga,b, Liping Zhanga,c, Wei Liua,c, Qingbo Zhanga,c, Haibo Zhanga,c, Changsheng Zhanga,b,c,d, Wenjun Zhanga,b,c()   

  1. a Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301
    b University of Chinese Academy of Sciences, Beijing 100049
    c Southern Marine Science and Engineering Guangdong Laboratory, Guangzhou 511458
    d Sanya Institute of Oceanology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Sanya, Hainan, 572000
  • Received:2021-10-26 Revised:2021-11-25 Published:2021-12-30
  • Contact: Wenjun Zhang
  • Supported by:
    National Natural Science Foundation of China(41676165); National Natural Science Foundation of China(41911530078); National Natural Science Foundation of China(41606193)

High performance liquid chromatography-diode array detection (HPLC-DAD)-based chemical analysis of the extract fraction library of the plateau soil-derived fungus Auxarthron umbrinum SCSIO 40432 led to the identification of eight compounds, including a known aromatic furanone glycoside malfilamentoside A (1) whose stereochemistry remained unsolved, and a new malfilamentoside D (2), together with six known compounds (3~8). The planar structures of malfilamentaosides A (1) and D (2) were elucidated by HRESIMS, 1D and 2D NMR spectroscopic analysis. The absolute configuration of malfilamentoside A (1) was unambiguously resolved for the first time by a single crystal X-ray diffraction analysis and the stereochemistry of malfilamentoside D (2) was determined by comparing electronic circular dichroism (ECD) spectra of 1 and 2. Malfilamentoside A (1) exhibited inhibitory activity to xanthine oxidase at the concentration of 20 μmol/L.

Key words: Auxarthron umbrinum SCSIO 40432, aromatic furanone glycoside, malfilamentoside, configurational assignment