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2022 , Vol. 42 >Issue 4: 1229 - 1234

DOI: https://doi.org/10.6023/cjoc202110038

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 ,
  • 王璐 ,
  • 张丽萍 ,
  • 刘威 ,
  • 张庆波 ,
  • 张海波 ,
  • 张长生 ,
  • 张文军
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  • 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

  网络出版日期: 2021-12-30

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)

收起

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

  • Huixin Xu ,
  • Lu Wang ,
  • Liping Zhang ,
  • Wei Liu ,
  • Qingbo Zhang ,
  • Haibo Zhang ,
  • Changsheng Zhang ,
  • Wenjun Zhang
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  • 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
* E-mail:

Received date: 2021-10-26

  Revised date: 2021-11-25

  Online published: 2021-12-30

Supported by

National Natural Science Foundation of China(41676165); National Natural Science Foundation of China(41911530078); National Natural Science Foundation of China(41606193)

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摘要

基于高效液相色谱-二级阵列检测器(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的电子圆二色谱(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; Malfilamentoside; 构型确定

本文引用格式

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, 2022 , 42(4) : 1229 -1234 . DOI: 10.6023/cjoc202110038

Abstract

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

参考文献

[1]
Yeh, H. H.; Chiang, Y. M.; Entwistle, R.; Ahuja, M.; Lee, K. H.; Bruno, K. S.; Wu, T. K.; Oakley, B. R.; Wang, C. C. C. Appl. Microbiol. Biotechnol. 2012, 96, 739.
[2]
Pauly, J.; Nett, M.; Hoffmeister, D. J. Nat. Prod. 2014, 77, 1967.
[3]
Brachmann, A. O.; Forst, S.; Furgani, G. M.; Fodor, A.; Bode, H. B. J. Nat. Prod. 2006, 69, 1830.
[4]
Kai, K.; Ohnishi, H.; Mori, Y.; Kiba, A.; Ohnishi, K.; Hikichi, Y. ChemBioChem 2014, 15, 2590.
[5]
Kai, K.; Ohnishi, H.; Kiba, A.; Ohnishi, K.; Hikichi, Y. Biosci., Biotechnol., Biochem. 2016, 80, 440.
[6]
Wakana, D.; Hosoe, T.; Itabashi, T.; Fukushima, K.; Kawai, K. Mycotoxins 2008, 58, 1.
[7]
Kim, J. W.; Son, S.; Kim, G. S.; Otaka, J.; Miura, Y.; Muranaka, A.; Uchiyama, M.; Lee, J.-S.; Jang, M.; Ko, S.-K.; Takahashi, S.; Osada, H.; Jang, J.-H.; Ahn, J. S. Tetrahedron Lett. 2019, 60, 151227.
[8]
Cui, H.; Lin, Y.; Luo, M.; Lu, Y.; Huang, X.; She, Z. Org. Lett. 2017, 19, 5621.
[9]
Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355.
[10]
Cimino, P. J.; Huang, L.; Du, L.; Wu, Y.; Bishop, J.; Dalsing- Hernandez, J.; Kotlarczyk, K.; Gonzales, P.; Carew, J.; Nawrocki, S.; Jordan, M. A.; Wilson, L.; Lloyd, G. K.; Wirsching, H.-G. Biomed. Rep. 2019, 10, 218.
[11]
Zhang, W.; Liu, Z.; Li, S.; Yang, T.; Zhang, Q.; Ma, L.; Tian, X.; Zhang, H.; Huang, C.; Zhang, S.; Ju, J.; Shen, Y.; Zhang, C. Org. Lett. 2012, 14, 3364.
[12]
Zhang, W.; Yang, C.; Huang, C.; Zhang, L.; Zhang, H.; Zhang, Q.; Yuan, C.; Zhu, Y.; Zhang, C. Org. Lett. 2017, 19, 592.
[13]
Wang, L.; Huang, Y.; Zhang, L.; Liu, Z.; Liu, W.; Xu, H.; Zhang, Q.; Zhang, H. B.; Yan, Y.; Liu, Z.; Zhang, T.; Zhang, W.; Zhang, C. Org. Biomol. Chem. 2021, 19, 6030.
[14]
Xu, H. X.; Yang, T.; Zhang, L. P.; Liu, W.; Zhang, H.-B.; Zhang, Q.-B.; Zhang, C.-S.; Zhang, W.-J. Tetrahedron Lett. 2021, 66, 152842.
[15]
Arima, K.; Komagata, K.; Shigehiko, M. J. Agric. Biol. Chem. Jpn. 1954, 28, 638.
[16]
Hosoe, T.; Fukushima, K.; Takizawa, K.; Miyaji, M.; Kawai, K. Phytochemistry 1999, 52, 459.
[17]
Avent, A. G.; Hanson, J. R.; Truneh, A. Phytochemistry 1992, 31, 1065.
[18]
Rhee, K.-H. J. Microbiol. Biotechnol. 2003, 13, 984.
[19]
Rangel-Grimaldo, M.; Macías-Rubalcava, M. L.; González- Andrade, M.; Raja, H.; Figueroa, M.; Mata, R. J. Nat. Prod. 2020, 83, 675.
[20]
Klinenberg, J. R.; Goldfinger, S. E.; Seegmiller, J. E. Ann. Intern. Med. 1965, 62, 639.
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