SIOC English
有机化学
高级检索

有机化学 >

2021 , Vol. 41 >Issue 11: 4493 - 4497

DOI: https://doi.org/10.6023/cjoc202107006

研究简报

蜜环菌YUD17010中一个新的原伊鲁烷型倍半萜芳基酯

  • 李洪涛 ,
  • 谢飞 ,
  • 孙岳 ,
  • 王萌 ,
  • 陈静圆 ,
  • 周皓 ,
  • 丁中涛
展开
  • a 云南大学化学科学与工程学院 云南省高校功能分子分析与生物转化重点实验室 昆明 650091
    b 昆明医科大学药学院 云南省天然药物药理重点实验室 昆明 650500
    c 大理大学药学院 云南大理 671000

收稿日期: 2021-07-02

  修回日期: 2021-07-21

  网络出版日期: 2021-08-10

基金资助

国家自然科学基金(81860623); 云岭学者计划资助项目

收起

A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010

  • Hongtao Li ,
  • Fei Xie ,
  • Yue Sun ,
  • Meng Wang ,
  • Jingyuan Chen ,
  • Hao Zhou ,
  • Zhongtao Ding
Expand
  • a Key Laboratory of Functional Molecules Analysis and Biotransformation, Yunnan Provincial Department of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091
    b Yunnan Key Laboratory of Pharmacology for Natural Products, School of Pharmaceutical Science, Kunming Medical University, Kunming 650500
    c College of Pharmacy, Dali University, Dali, Yunnan 671000
* Corresponding authors. E-mail: ;

Received date: 2021-07-02

  Revised date: 2021-07-21

  Online published: 2021-08-10

Supported by

National Natural Science Foundation of China(81860623); Project of Yunling Scholars of Yunnan Province

Fold

摘要

对蜜环菌YUD17010发酵提取物进行化学研究, 从中分离纯化得到三个原伊鲁烷型倍半萜芳基酯, 包括一个新化合物armilaroma (1)以及两个已知化合物4-dehydrodihydromelleolide (2)和armillarivin (3). 通过波谱数据分析确定了它们的结构和相对立体构型, 并借助基于量子化学计算的电子圆二色性(ECD)谱确定了化合物的绝对构型. Armilaroma (1)表现出中等的乙酰胆碱酯酶(AChE)抑制活性, IC50值为9.03 μmol/L. 此外, 还评估了化合物1对人类癌症细胞MCF-7、SW480、HL-60、A-549和SMMC-7721的细胞毒活性, IC50值范围为13.73~17.92 μmol/L.

关键词： 蜜环菌; 真菌代谢产物; 细胞毒活性; 倍半萜芳基酯

本文引用格式

李洪涛 , 谢飞 , 孙岳 , 王萌 , 陈静圆 , 周皓 , 丁中涛 . 蜜环菌YUD17010中一个新的原伊鲁烷型倍半萜芳基酯[J]. 有机化学, 2021 , 41(11) : 4493 -4497 . DOI: 10.6023/cjoc202107006

Abstract

A chemical investigation on the cultures extract of the basidiomycete Armillaria sp. YUD17010 led to the isolation of three protoilludane-type sesquiterpene aryl esters, including a new one armilaroma (1), along with two known ones 4-dehydrodihydromelleolide (2) and armillarivin (3). Their structures and relative configurations were established on the basis of spectroscopic data analysis, and the absolute configurations were assigned by electronic circular dichroism (ECD) spectra aided by quantum chemical calculations. Armilaroma (1) exhibited moderate acetylcholinesterase (AChE) inhibitory activity with an IC50 value of 9.03 μmol/L. Moreover, cytotoxicities against the MCF-7, SW480, HL-60, A-549, and SMMC-7721 human cancer cell lines were also evaluated for compound 1, with the IC50 values ranging from 13.73 μmol/L to 17.92 μmol/L.

Key words： Armillaria sp.; fungal metabolite; cytotoxicity; sesquiterpene aryl ester

参考文献

[1]
Carroll, A. R.; Copp, B. R.; Davis, R. A.; Keyzers, R. A.; Prinsep, M. R. Nat. Prod. Rep. 2019, 36, 122.
[2]
Meng, L. H.; Li, X. M.; Zhang, F. Z.; Wang, Y. N.; Wang, B. G. J. Nat. Prod. 2020, 83, 2528.
[3]
Liu, L.; Wang, L.; Bao, L.; Ren, J.; Bahadur Basnet, B.; Liu, R.; He, L.; Han, J.; Yin, W. B.; Liu, H. Org. Lett. 2017, 19, 942.
[4]
Chen, S.; Liu, H.; Liu, Z.; Li, S.; Chen, Y.; Li, H.; Li, D.; Zhang, W. Chin. J. Org. Chem. 2020, 40, 209. (in Chinese)
[4]
(陈书帅, 刘洪新, 刘昭明, 李赛妮, 陈玉婵, 李浩华, 李冬利, 章卫民, 有机化学, 2020, 40, 209.)
[5]
Bohnert, M.; Nützmann, H. W.; Schroeckh, V.; Horn, F.; Dahse, H. M.; Brakhage, A. A.; Hoffmeister, D. Phytochemistry 2014, 105, 101.
[6]
Sun, Y.; Liang, H.; Zhang, X.; Tong, H.; Liu, J. Bioresour. Technol. 2009, 100, 1860.
[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. 2021, 1.
[8]
Yin, Xia.; Fen, T.; Liu, J. K. Nat. Prod. Bioprospect. 2012, 2, 245.
[9]
Bohnert, M.; Miethbauer, S.; Dahse, H. M.; Ziemen, J.; Nett, M.; Hoffmeister, D. Bioorg. Med. Chem. Lett. 2011, 21, 2003.
[10]
Li, H. T.; Tang, L.; Liu, T.; Yang, R.; Yang, Y.; Zhou, H.; Ding, Z. T. Org. Chem. Front. 2019, 6, 3847.
[11]
Li, H. T.; Zhou, H.; Duan, R. T.; Li, H. Y.; Tang, L. H.; Yang, X. Q.; Yang, Y. B.; Ding, Z. T. J. Nat. Prod. 2019, 82, 1009.
[12]
Li, H. T.; Liu, T.; Yang, R.; Xie, F.; Yang, Z.; Yang, Y.; Zhou, H.; Ding, Z. T. RSC Adv. 2020, 10, 18384.
[13]
Donnelly, D. M.; Konishi, T.; Dunne, O.; Cremin, P. Phytochemistry 1997, 44, 1473.
[14]
Bashyal, B. P.; Wijeratne, E. K.; Faeth, S. H.; Gunatilaka, A. L. J. Nat. Prod. 2005, 68, 724.
[15]
Jagannadh, B.; Reddy, S.S.; Thangavelu, R. J. Mol. Model. 2004, 10, 55.
[16]
He, J.; Pu, C. J.; Wang, M.; Li, Z. H.; Feng, T.; Zhao, D. K.; Liu, J. K. J. Nat. Prod. 2020, 83, 2743.
[17]
Li, H. T.;L. Tang, H.; Liu, T.; Yang, R. N.; Yang, Y. B.; Zhou, H.; Ding, Z. T. Bioorg. Chem. 2020, 95, 103503.
[18]
Bruhn, T.; Schaumlo?ffel, A.; Hemberger, Y. SpecDis, version 1. 64, University of Wu?erzburg, Germany, 2015.
[19]
Cory, A. H.; Owen, T. C.; Barltrop, J. A.; Cory, J. G. Cancer Commun. 1991, 3, 207.
[20]
Reed, L. J.; Muench, H. Am. J. Epidemiol. 1938, 27, 493.
[21]
Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88.
[22]
Di Giovanni, S.; Borloz, A.; Urbain, A.; Marston, A.; Hostettmann, K.; Carrupt, P. A.; Reist, M. Eur. J. Pharm. Sci. 2008, 33, 109.
[23]
Houghton, P. J.; Ren, Y. H.; Howes, M. J. Nat. Prod. Rep. 2006, 23, 181.
[24]
Guo, Q.; Si, X. L.; Shi, Y. T.; Yang, H. S.; Liu, X. Y.; Liang, H.; Tu, P. F.; Zhang, Q. Y. J. Nat. Prod. 2019, 82, 3288.
Options
文章导航

/

〈 〉