Citation: Yang Ningning, Kong Fandong, Ma Qingyun, Huang Shengzhuo, Luo Duqiang, Zhou Liman, Dai Haofu, Yu Zhifang, Zhao Youxing. Chemical Constituents from the Cultures of Fungus Xylaria polymorpha[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 1033-1039. doi: 10.6023/cjoc201612039 shu

Chemical Constituents from the Cultures of Fungus Xylaria polymorpha

Yang Ningning ^a,b ,
Kong Fandong ^b ,
Ma Qingyun ^b ,
Huang Shengzhuo ^b ,
Luo Duqiang ^c ,
Zhou Liman ^b ,
Dai Haofu ^b ,
Yu Zhifang ^a,*,, ,
Zhao Youxing ^b,*,,

a.
College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095
b.
Key Laboratory of Biology and Genetic Resources of Tropical Crops, Institute of Tropical Bioscience and Biotechnology, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101
c.
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, College of Life Science, Baoding 071002

Corresponding author: Yu Zhifang, yuzhifang@njau.edu.cn Zhao Youxing, zhaoyouxing@itbb.org.cn
Received Date: 12 December 2016
Revised Date: 22 December 2016

Fund Project: the Fundamental Scientific Research Funds for Chinese Academy of Tropical Agricultural Sciences 1630052016008the Natural Science Foundation of Hainan Province 20153143the Special Fund for Agro-Scientific Research in the Public Interest 201303117

Figures(4)

Totally 21 compounds were isolated from the EtOAc extract of fermentation broth of fungus Xylaria polymorpha (Pers.: Fr.) Grer, including two new drimane-type sesquiterpenoids named polymorphines A and B (1~2) and one new phenyloxolane compound named 2-methyl-2-(4-hydroxymethylphenyl) oxolane (3), together with 18 known compounds 4~21. The structures of these compounds were elucidated by NMR and single-crystal X-ray diffraction analysis. Compound 2 exhibited anti-acetylcholinesterase and α-glucosidase inhibitory activities. Moreover, compound 3 showed moderate inhibitory activitiy against the nematode Panagrellus redivivus with mortality ratio of 59.6% at 2.5 mg/mL.
- Xylaria polymorpha,
- sesquiterpene,
- AChE inhibitory activity,
- α-glucosidase inhibitory activity,
- anti-nematode activity
1. [1]
  Lee, I. K.; Jang, Y. W.; Kim, Y. S.; Yu, S. H.; Lee, K. J.; Park, S. M.; Oh, B. T.; Chae, J. C.; Yun, B. S. J. Antibiot. 2009, 62, 163. doi: 10.1038/ja.2008.20
2. [2]
  Shiono, Y.; Motoki, S.; Koseki, T.; Murayama, T.; Tojima, M.; Kimura, K. I. Phytochemistry 2009, 70, 935. doi: 10.1016/j.phytochem.2009.03.023
3. [3]
  Jang, Y. W.; Lee, I. K.; Kim, Y. S.; Lee, S. K.; Lee, H. J.; Yu, S. H.; Yun, B. S. J. Antibiot. 2007, 60, 696. doi: 10.1038/ja.2007.89
4. [4]
  Shan, W.-G.; Chen, X.-X.; Ying, Y.-M.; Zhan, Z.-J. HeIv. Chim. Acta 2011, 94, 1254. doi: 10.1002/hlca.v94.7
5. [5]
  William, A. A.; Latchezar, S. T. J. Nat. Prod. 1992, 55, 1454. doi: 10.1021/np50088a011
6. [6]
  He, J.-B.; Tao, J.; Miao, X.-S.; Bu, W.; Zhang, S.; Dong, Z.-J.; Li, Z.-H.; Feng, T.; Liu, J.-K. Fitoterapia 2015, 102, 1. doi: 10.1016/j.fitote.2015.01.022
7. [7]
  Li, Q.-J.; Wang, C.; Li, J.-X.; Zhang, J.-J.; Liu, Y.-H.; Pan, L.-T. Chin. Pharm. J. 2014, 49, 550 (in Chinese).
8. [8]
  Pei, G.; Zhou, P.-H.; He, G.-X.; Du, F.-L.; Jiang, D.-S. Nat. Prod. Res. Dev. 2004, 16, 213 (in Chinese). doi: 10.3969/j.issn.1001-6880.2004.03.008
9. [9]
  Dean, V.-J.; Herfried, G. Tetrahedron 1997, 53, 617. doi: 10.1016/S0040-4020(96)01023-X
10. [10]
  Huang, X.-S.; Gao, S.; Fan, L. H.; Yu, S.-S.; Liang, X.-T. China J. Chin. Mater. Med. 2004, 29, 1108 (in Chinese). doi: 10.3321/j.issn:1001-5302.2004.11.028
11. [11]
  Zhou, W.-W.; Guo, S.-X. Chem. Nat. Compd. 2009, 45, 124. doi: 10.1007/s10600-009-9229-x
12. [12]
  Li, W.-H.; Chang, S.-T.; Chang, S.-C.; Chang, H.-T. Nat. Prod. Res. 2008, 22, 1085. doi: 10.1080/14786410802267510
13. [13]
  Luo, P.; Su, J.; Zhu, Y.-L.; Wei, J.-H.; Wei, W.-X.; Pan, W.-G. Nat. Prod. Res. 2016, 30, 2190. doi: 10.1080/14786419.2016.1160231
14. [14]
  Hybelbauerová, S.; Sejbal, J.; DracInsky, M.; Hahnová, A.; Koutek, B. Chem. Biodiversity 2008, 5, 743. doi: 10.1002/(ISSN)1612-1880
15. [15]
  Liu, X.-H.; Miao, F.-P.; Liang, X.-R.; Ji, N.-Y. Nat. Prod. Res. 2014, 28, 1182. doi: 10.1080/14786419.2014.923996
16. [16]
  Kwon, H. C.; Zee, S. D.; Cho, S. Y.; Choi, S. U.; Lee, K. R. Arch. Pharm. Res. 2002, 25, 851. doi: 10.1007/BF02977003
17. [17]
  Gao, H.; Hong, K.; Zhang, X.; Liu, H.-W.; Wang, N.-L.; Zhuang, L.; Yao, X.-S. HeIv. Chim. Acta 2007, 90, 1165. doi: 10.1002/(ISSN)1522-2675
18. [18]
  Fangkrathok, N.; Sripanidkulchai, B.; Umehara, K.; Noguchi, H. Nat. Prod. Res. 2012, 27, 1611.
19. [19]
  Amagata, T.; Tanaka, M.; Yamada, T.; Doi, M.; Minoura, K.; Ohishi, H.; Yamori, T.; Numata, A. J. Nat. Prod. 2007, 70, 1731. doi: 10.1021/np070165m
20. [20]
  E, H.-C.; Zhou, W.; Liu, B.-S.; Tang, H.; Sun, P.; Li, L.; Zhang, W. Chin. J. Marine Drugs 2013, 32, 8 (in Chinese).
21. [21]
  Butova, E. D.; Barabash, A. V.; Petrova, A. A.; Kleiner, C. M.; Schreiner, P. R.; Fokin, A. A. J. Org. Chem. 2010, 75, 6229. doi: 10.1021/jo101330p
22. [22]
  Ellman, G. L.; Courtney, K. D.; Jr., V. A.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88. doi: 10.1016/0006-2952(61)90145-9
23. [23]
  Li, T.; Zhang, X.-D.; Song, Y.-W.; Liu, J.-W. Chin. J. Clin. Pharmacol. Ther. 2005, 10, 1128 (in Chinese). doi: 10.3969/j.issn.1009-2501.2005.10.011
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