Citation: Bai Jiao, Guo Feng, Wang Rui, Chen Gang, Li Zhanlin, Shao Meili, Xue Chunmei, Hua Huiming. Asperterzine, a symmetric aromatized derivative of epipolythiodioxopiperazine, from the endophytic fungus Aspergillus terreus PR-P-2[J]. Chinese Chemical Letters, ;2018, 29(3): 535-537. doi: 10.1016/j.cclet.2017.09.006 shu

Asperterzine, a symmetric aromatized derivative of epipolythiodioxopiperazine, from the endophytic fungus Aspergillus terreus PR-P-2

Bai Jiao ^a,b ,
Guo Feng ^a,b ,
Wang Rui ^a,b ,
Chen Gang ^a,b ,
Li Zhanlin ^a,b ,
Shao Meili ^a,b ,
Xue Chunmei ^a,b ,
Hua Huiming ^a,b,*,,

a.
Key Laboratory of Structure-Based Drug Design and Discovery(Shenyang Pharmaceutical University), Ministry of Education, Shenyang 110016, China
b.
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China

Corresponding author: Hua Huiming, huimhua@163.com

Received Date: 18 May 2017
Revised Date: 15 August 2017
Accepted Date: 4 September 2017
Available Online: 6 March 2017

Figures(4)

A new epipolythiodioxopiperazine (ETP), asperterzine (1), along with two known analogs, bisdethiobis (methylthio)-acetylaranotin (2) and bisdethiobis(methylthio)-acetylapoaranotin (3), was isolated from the plant endophytic fungus Aspergillus terreus PR-P-2. The structure elucidation of 1 was accomplished by a combination of spectral methods and electronic circular dichroism (ECD) spectrum. Asperterzine (1) was a symmetric aromatized ETP found as a natural product for the first time. Compounds 2 and 3 showed strong cytotoxicity against HL-60 cell line. The putative biosynthetic pathway of 1 was also detailed in the text.
- Asperterzine,
- Epipolythiodioxopiperazine,
- Plant endophytic fungus,
- Aspergillus terreus,
- Cytotoxicity
1. [1]
  Y. Liu, X.M. Li, L.H. Meng, et al., Mar. Drugs 13(2015) 3640-3652. doi: 10.3390/md13063640
2. [2]
  T.R. Welch, R.M. Williams, Nat. Prod. Rep. 31(2013) 1376-1404.
3. [3]
  R. Nagarajan, N. Neu, M.M. Marsh, J. Nat. Prod. 90(1968) 6518-6519.
4. [4]
  M.A. Stillwell, L.P. Magasi, G.M. Strunz, Can. J. Microbiol. 20(1974) 759-764. doi: 10.1139/m74-116
5. [5]
  P.W. Trown, Biochem. Biophys. Res. Commun. 33(1968) 403-407.
6. [6]
  Y. Li, Q. Yue, N.M. Krausert, et al., J. Nat. Prod. 79(2016) 2357-2363. doi: 10.1021/acs.jnatprod.6b00498
7. [7]
  G. Deffieux, M.A. Baute, R. Baute, et al., J. Antibiot. 31(1978) 1102-1105. doi: 10.7164/antibiotics.31.1102
8. [8]
  N. Kawahara, S. Nakajima, M. Yamazaki, et al., Chem. Pharm. Bull. 37(1989) 2592-2595. doi: 10.1248/cpb.37.2592
9. [9]
  G.M. Strunz, C.J. Heissner, M. Kakushima, et al., Can. J. Chem. 52(1974) 325-326. doi: 10.1139/v74-052
10. [10]
  Y. Liu, X.M. Li, L.H. Meng, et al., J. Nat. Prod. 78(2015) 1294-1299. doi: 10.1021/acs.jnatprod.5b00102
11. [11]
  H. Onodera, A. Hasegawa, N. Tsumagari, et al., Org. Lett. 6(2004) 4101-4104. doi: 10.1021/ol048202d
12. [12]
  R.L. DeVault, W. Rosenbrook, J. Antibiot. 26(1973) 532-534. doi: 10.7164/antibiotics.26.532
13. [13]
  Y. Ueno, K. Umemori, E. Niimi, et al., J. Nat. Toxins 3(1995) 129-137. doi: 10.1002/(ISSN)1056-9014
14. [14]
  F. Guo, Z.L. Li, X.W. Xu, et al., Fitoterapia 113(2016) 44-50. doi: 10.1016/j.fitote.2016.06.014
15. [15]
  C.J. Guo, H.H. Yeh, Y.M. Chiang, et al., J. Am. Chem. Soc. 135(2013) 7205-7213. doi: 10.1021/ja3123653
16. [16]
  Z.J. Lin, T.J. Zhu, Y.C. Fang, et al., Magn. Reson. Chem. 46(2008) 1212-1216. doi: 10.1002/mrc.v46:12
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