SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

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

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

NOTES

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

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

Cite this article

Hongtao Li , Fei Xie , Yue Sun , Meng Wang , Jingyuan Chen , Hao Zhou , Zhongtao Ding . A New Protoilludane Sesquiterpene Aryl Ester from Armillaria sp. YUD17010[J]. Chinese Journal of Organic Chemistry, 2021 , 41(11) : 4493 -4497 . DOI: 10.6023/cjoc202107006

References

[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
Outlines

/

〈 〉