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

doi:10.6023/cjoc202110038

有机化学 ›› 2022, Vol. 42 ›› Issue (4): 1229-1234.DOI: 10.6023/cjoc202110038 上一篇下一篇

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

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)

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摘要/Abstract

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

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

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, 2022, 42(4): 1229-1234.

Huixin Xu, Lu Wang, Liping Zhang, Wei Liu, Qingbo Zhang, Haibo Zhang, Changsheng Zhang, Wenjun Zhang. Configurational Assignment of Malfilamentoside A and a New Furanone Glycoside Malfilamentoside D[J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1229-1234.

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图/表 3

Figure 1. Sructures of compounds 1~8

Figure 2. (A) Key COSY and HMBC correlations of compounds 1 and 2, 1H-1H coupling constants (Hz) and key NOESY correlations of the sugar unit in 1 and 2; (B) X-ray crystal structures of 1 (the ellipsoids of non-hydrogen atoms are shown at 50% probability levels); (C) Comparison of experimental ECD spectra of 1 and 2

Scheme 1. Proposed biosynthesis of compounds 1~2

参考文献 20

[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. doi: 10.1007/s00253-012-4098-9
[2]	Pauly, J.; Nett, M.; Hoffmeister, D. J. Nat. Prod. 2014, 77, 1967. doi: 10.1021/np500263r
[3]	Brachmann, A. O.; Forst, S.; Furgani, G. M.; Fodor, A.; Bode, H. B. J. Nat. Prod. 2006, 69, 1830. doi: 10.1021/np060409n
[4]	Kai, K.; Ohnishi, H.; Mori, Y.; Kiba, A.; Ohnishi, K.; Hikichi, Y. ChemBioChem 2014, 15, 2590. doi: 10.1002/cbic.201402404
[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. doi: 10.2520/myco.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. doi: 10.1016/j.tetlet.2019.151227
[8]	Cui, H.; Lin, Y.; Luo, M.; Lu, Y.; Huang, X.; She, Z. Org. Lett. 2017, 19, 5621. doi: 10.1021/acs.orglett.7b02748
[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. doi: 10.1002/anie.200390115
[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. doi: 10.1021/ol301343n
[12]	Zhang, W.; Yang, C.; Huang, C.; Zhang, L.; Zhang, H.; Zhang, Q.; Yuan, C.; Zhu, Y.; Zhang, C. Org. Lett. 2017, 19, 592. doi: 10.1021/acs.orglett.6b03745
[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. doi: 10.1039/D1OB00869B
[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. doi: 10.1016/j.tetlet.2021.152842
[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. doi: 10.1016/S0031-9422(99)00237-X
[17]	Avent, A. G.; Hanson, J. R.; Truneh, A. Phytochemistry 1992, 31, 1065. doi: 10.1016/0031-9422(92)80079-T
[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. doi: 10.1021/acs.jnatprod.9b01108 pmid: 31898904
[20]	Klinenberg, J. R.; Goldfinger, S. E.; Seegmiller, J. E. Ann. Intern. Med. 1965, 62, 639. doi: 10.7326/0003-4819-62-4-639

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

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

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