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2025 , Vol. 45 >Issue 4: 1411 - 1416

DOI: https://doi.org/10.6023/cjoc202407037

研究简报

高卢蜜环菌中一个新的甾体类化合物

  • 张晶晶 ,
  • 李慧琼 ,
  • 张兴杰 ,
  • 王永朋 ,
  • 周学梅 ,
  • 肖伟烈 ,
  • 程立君 ,
  • 李晓莉
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  • a 云南大学药学院 教育部自然资源药物化学重点实验室 云南省特色植物提取实验室有限公司 昆明 650500
    b 昭通学院农学与生命科学学院 云南省天麻与真菌共生生物学重点实验室 云南昭通 657000
    c 云南大学国际河流与生态安全研究院 昆明 650500
    d 云南大学化学科学与工程学院 昆明 650500
    e 西南联合研究生院 昆明 650092
† 共同第一作者

收稿日期: 2024-07-24

  修回日期: 2024-09-06

  网络出版日期: 2024-10-18

基金资助

国家自然科学基金(82260682); 昭通学院云南天麻与真菌共生生物学重点实验室(TMKF2023A01); 云南特色植物筛选与研发服务CXO平台(2022YKZY001); 云岭学者计划资助项目

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A New Steroid from Armillaria gallica

  • Jingjing Zhang ,
  • Huiqiong Li ,
  • Xingjie Zhang ,
  • Yongpeng Wang ,
  • Xuemei Zhou ,
  • Weilie Xiao ,
  • Lijun Cheng ,
  • Xiaoli Li
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  • a Yunnan Characteristic Plant Extraction Laboratory Co. Ltd., Key Laboratory of Medicinal Chemistry for Natural Resource (Ministry of Education), School of Pharmacy, Yunnan University, Kunming 650500
    b Yunnan Key Laboratory of Gastrodia and Fungi Symbiotic Biology, College of Agriculture and Life Sciences, Zhaotong University, Zhaotong, Yunnan 657000
    c Institute of International Rivers and Eco-Security, Yunnan University, Kunming 650500
    d School of Chemical Science and Technology, Yunnan University, Kunming 650500
    e Southwest United Graduate School, Kunming 650092
† These authors contributed equally to this work.
* E-mail: ;
;

Received date: 2024-07-24

  Revised date: 2024-09-06

  Online published: 2024-10-18

Supported by

National Natural Science Foundation of China(82260682); Yunnan Key Laboratory of Gastrodia and Fungi Symbiotic Biology of Zhaotong University(TMKF2023A01); Yunnan Characteristic Plant Screening and R & D Service CXO Platform(2022YKZY001); Project of Yunling Scholars of Yunnan Province

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摘要

对蜜环菌Armillaria gallica Marxm. & Romagn.发酵提取物进行化学成分研究, 从中分离得到1个新的甾体类化合物armillanal D (1), 1个新天然产物VD2-1 (8)以及6个已知化合物. 综合运用1D、2D的核磁共振波谱、高分辨质谱和电子圆二色性(ECD)谱对化合物1的结构进行了鉴定. 在小鼠巨噬细胞(J774A.1)中, 评价了除化合物8以外所有化合物对尼日利亚菌素(Nigericin)诱导的NLRP3炎症小体激活的抑制作用, chaxine C (6)表现出较好的抗炎活性, 其IC50值为(4.97±0.81) μmol/L.

关键词： 高卢蜜环菌; 真菌代谢产物; 甾体; 抗炎活性

本文引用格式

张晶晶 , 李慧琼 , 张兴杰 , 王永朋 , 周学梅 , 肖伟烈 , 程立君 , 李晓莉 . 高卢蜜环菌中一个新的甾体类化合物[J]. 有机化学, 2025 , 45(4) : 1411 -1416 . DOI: 10.6023/cjoc202407037

Abstract

A chemical investigation on the cultures extract of the basidiomycete Armillaria gallica Marxm. & Romagn. led to the isolation of eight compounds, including a new steroid armillanal D (1), a new natural product VD2-1 (8) and six known compounds. The structure of 1 was elucidated on the basis of extensive 1D and 2D-NMR spectra analysis, HR-ESI-MS, and electronic circular dichroism (ECD) spectra. The inhibitory activity of these compounds except 8 on NLRP3 inflammasome activation in Nigericin-induced mouse macrophage (J774A.1) cells was evaluated. Chaxine C (6) exhibited potential anti- inflammatory activity in vitro with IC50 value of (4.97±0.81) μmol/L.

Key words： Armillaria gallica; fungal metabolite; steroid; anti-inflammatory activity

参考文献

[1]
Chen, C.-C.; Kuo, Y.-H.; Cheng, J.-J.; Sung, P.-J.; Ni, C.-L.; Chen, C.-C.; Shen, C.-C. Molecules 2015, 20, 9994.
[2]
Zhan, M.; Tian, M.; Wang, W.; Li, G.; Lu, X.; Cai, G.; Yang, H.; Du, G.; Huang, L. Braz. J. Microbiol. 2020, 51, 1539.
[3]
Chang, C.-W.; Lur, H.-S.; Lu, M.-K.; Cheng, J.-J. Food Res. Int. 2013, 54, 239.
[4]
Heo, J. C.; Woo, S. U.; Son, M.; Park, J. Y.; Choi, W. S.; Chang, K. T.; Lee, S. H. Oncol. Rep. 2007, 18, 849.
[5]
Momose, I.; Sekizawa, R.; Hosokawa, N.; Iinuma, H.; Maisui, S.; Nakamura, H.; Naganawa, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 2000, 53, 137.
[6]
Li, Z.-J.; Wang, Y.-C.; Jiang, B.; Li, W.-L.; Zheng, L.-H.; Yang, X.-G.; Bao, Y.-L.; Sun, L.-G.; Huang, Y.-X.; Li, Y.-X. J. Ethnopharmacol. 2016, 184, 119.
[7]
Lou, S.-Z.; Feng, J.; Yang, R.; Li, Y.-P.; Gao, L.; Du, G.; Yang, H.-Y.; Hu, Q.-F.; Zhou, W.-B.; Wang, L.-S.; Wang, W.-G. J. Asian Nat. Prod. Res. 2022, 24, 59.
[8]
Li, H.-T.; Xie, F.; Sun, Y.; Wang, M.; Chen, J.-Y.; Zhou, H.; Ding, Z.-T. Chin. J. Org. Chem. 2021, 41, 4493 (in Chinese).
[8]
(李洪涛, 谢飞, 孙岳, 王萌, 陈静圆, 周皓, 丁中涛, 有机化学, 2021, 41, 4493.)
[9]
Yang, J.-S.; Su, Y.-L.; Wang, Y.-L.; Feng, X.-Z.; Liang, X.-T. Planta Med. 1991, 57, 478.
[10]
Yang, J.-S.; Su, Y.-L.; Wang, Y.-L.; Feng, X.-Z.; Yu, D.-Q.; Liang, X.-T. J. Pharm. Sci. 1991, 26, 117.
[11]
Guo, W.-J.; Guo, S.-X.; Yang, J.-S.; Chen, X.-M.; Xiao, P.-G. Biochem. Syst. Ecol. 2007, 35, 790.
[12]
Zhang, S.-S. Ph.D. Dissertation, China Academy of Chinese Medical Sciences, Beijing, 2015 (in Chinese).
[12]
(张姗姗. 博士论文, 中国中医科学院, 北京, 2015.)
[13]
Wang, Y.-C.; Zhang, Y.-W.; Zheng, L.-H.; Bao, Y.-L.; Wu, Y.; Yu, C.-L.; Huang, Y.-X.; Sun, L.-G.; Zhang, Y.; Jia, X.-J.; Li, Y.-X. Helv. Chim. Acta 2013, 96, 330.
[14]
Alves, M.; Ferreira, I. F. R.; Dias, J.; Teixeira, V.; Martins, A.; Pintado, M. Planta Med. 2012, 78, 1707.
[15]
Khazaal, H. T.; Khazaal, M. T.; Abdel-Razek, A. S.; Hamed, A. A.; Ebrahim, H. Y.; Ibrahim, R. R.; Bishr, M.; Mansour, Y. E.; El Dib, R. A.; Soliman, H. S. M. AMB Express 2023, 13, 68.
[16]
Wei, M.; Li, X.; Liao, H.; Liu, L.; Li, Q.; Sun, W.; Chen, C.; Zhu, H.; Zhang, Y. Phytochemistry 2023, 213, 113785.
[17]
Yue, Q.; Miller, C. J.; White, J. F.; Richardson, M. D. J. Agric. Food Chem. 2000, 48, 4687.
[18]
Kawagishi, H.; Katsumi, R.; Sazawa, T.; Mizuno, T.; Hagiwara, T.; Nakamura, T. Phytochemistry 1988, 27, 2777.
[19]
Choi, J. H.; Ogawa, A.; Abe, N.; Masuda, K.; Koyama, T.; Yazawa, K.; Kawagishi, H. Tetrahedron 2009, 65, 9850.
[20]
Mansoor, T. A.; Hong, J.; Lee, C. O.; Bae, S. J.; Im, K. S.; Jung, J. H. J. Nat. Prod. 2005, 68, 331.
[21]
Wanibuchi, K.; Hosoda, K.; Ihara, M.; Tajiri, K.; Sakai, Y.; Masui, H.; Takahashi, T.; Hirai, Y.; Shimomura, H. Lipids 2018, 53, 393.
[22]
Bruhn, T.; Pescitelli, G. Chirality 2016, 28, 749.
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