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

doi:10.6023/cjoc2021110038

研究简报

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,*

^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邮编 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邮编 511458;
^d三亚中科海洋研究院三亚 572000

收稿日期:2021-10-26 修回日期:2021-11-25
基金资助:
国家自然科学基金(No. 41676165, 41911530078, 41606193)资助项目.

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

Xu Huixin^a,b, Wang Lu^a,b, Zhang Liping^a,c, Liu Wei^a,c, Zhang Qingbo^a,c, Zhang Haibo^a,c, Zhang Changsheng^a,b,c,d, Zhang Wenjun^a,b,c,*

^aKey Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Innovation Academy of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301;
^bUniversity of Chinese Academy of Sciences, Beijing 100049;
^cSouthern Marine Science and Engineering Guangdong Laboratory (Guangzhou), Guangzhou 511458;
^dSanya Institute of Oceanology, SCSIO, Yazhou Scientific Bay, Sanya 572000

Received:2021-10-26 Revised:2021-11-25
Contact: * E-mail: wzhang@scsio.ac.cn
Supported by:
NSFC (41676165, 41911530078, 41606193)

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摘要/Abstract

基于HPLC-DAD追踪方法从高原土壤来源真菌Auxarthron umbrinum SCSIO 40432发酵产物中分离获得8个化合物,包括malfilamentoside A（1）、新的芳香呋喃酮糖苷类化合物malfilamentoside D（2）及6个已知化合物（3-8）。通过1D、2D NMR确定了化合物的平面结构,首次通过X-射线单晶衍射确定了malfilamentoside A (1)的绝对构型,比较化合物1和2的ECD谱确定了malfilamentoside D（2）的立体构型。化合物1对黄嘌呤氧化酶有弱的抑制活性。

关键词: Auxarthron umbrinum SCSIO 40432, 芳香呋喃酮糖苷类化合物Malfilamentosides, 构型确定

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 malfilamentaoside 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 ECD spectra of 1 and 2. Malfilamentoside A (1) exhibited inhibitory activity to xanthine oxidase at the concentration of 20 μM.

Key words: Auxarthron umbrinum SCSIO 40432, Aromatic furanone glycoside malfilamentoside, Configurational assignment

引用此文

徐慧欣, 王璐, 张丽萍, 刘威, 张庆波, 张海波, 张长生, 张文军. Malfilamentoside A的构型确定与新呋喃糖苷类化合物malfilamentoside D[J]. 有机化学, doi: 10.6023/cjoc2021110038.

Xu Huixin, Wang Lu, Zhang Liping, Liu Wei, Zhang Qingbo, Zhang Haibo, Zhang Changsheng, Zhang Wenjun. Configurational Assignment of Malfilamentoside A and a New Furanone Glycoside Malfilamentoside D[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc2021110038.

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