Citation: Hao Zhou, Ya-Bin Yang, Rong-Ting Duan, Xue-Qiong Yang, Ju-Cheng Zhang, Xiao-Guang Xie, Li-Xing Zhao, Zhong-Tao Ding. Neopeapyran, an unusual furo[2, 3b]pyran analogue and turnagainolide C from a soil Streptomyces sp. S2236[J]. Chinese Chemical Letters, ;2016, 27(7): 1044-1047. doi: 10.1016/j.cclet.2016.03.018 shu

Neopeapyran, an unusual furo[2, 3b]pyran analogue and turnagainolide C from a soil Streptomyces sp. S2236

a.
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China
b.
Yunnan Institute of Microbiology, Yunnan University, Kunming 650091, China

Corresponding author: Zhong-Tao Ding, ztding@ynu.edu.cn
Received Date: 1 December 2015
Revised Date: 4 March 2016
Accepted Date: 7 March 2016
Available Online: 19 July 2016

Figures(3)

Neopeapyran (1), an unusual furo[2, 3b]pyran analogue, together with a new cyclopeptide, turnagainolide C (2), were isolated from Streptomyces sp. S2236 associated with the rhizosphere soil of Panax notoginseng. The planar structure and relative configuration of neopeapyran (1)) were elucidated on the basis of spectroscopic techniques, while the absolute configuration was determined by TDDFT calculation. The absolute configuration of turnagainolide C (2) was determined by partial hydrolysis, together with the advanced Marfey's method and spectroscopic analysis. The antimicrobial activities of these two compounds were also investigated.
- Streptomyces sp.,
- Furo[2, 3b]pyran analogue,
- Cyclopeptide,
- Structure elucidation,
- Antimicrobial activity
1. [1]
  M.F. Traxler, R. Kolter. Natural products in soil microbe interactions and evolution[J]. Nat. Prod. Rep., 2015,32:956-970. doi: 10.1039/C5NP00013K
2. [2]
  Z.G. Khalil, A.A. Salim, E. Lacey, A. Blumenthal, R. Capon, Wollamides: antimycobacterial cyclic hexapeptides from an Australian soil Streptomyces, J. Org. Lett. 16 (2014) 5120-5123.
3. [3]
  S.H. Kim, Y. Shin, S.H. Lee. Salternamides A-D from a halophilic Streptomyces sp. actinobacterium[J]. J. Nat. Prod., 2015,78:836-843. doi: 10.1021/acs.jnatprod.5b00002
4. [4]
  J. Bé rdy. Bioactive microbial metabolites[J]. J. Antibiot., 2005,58:1-26. doi: 10.1038/ja.2005.1
5. [5]
  A. Schatz, E. Bugle, S.A. Waksman, Streptomycin, a substance exhibiting antibiotic activity against gram-positive and gram-negative bacteria, Exp. Biol. Med. 55 (1944) 66-69.
6. [6]
  S.A. Waksman, H.A. Lechevalier, Neomycin, a new antibiotic active against streptomycin-resistant bacteria, including tuberculosis organisms, Science 109 (1949) 305-307.
7. [7]
  K.S. Lam. Discovery of novel metabolites from marine actinomycetes[J]. Curr. Opin. Microbiol., 2006,9:245-251. doi: 10.1016/j.mib.2006.03.004
8. [8]
  J.M. Crawford, J. Clardy. Bacterial symbionts and natural products[J]. Chem. Commun., 2011,47:7559-7566. doi: 10.1039/c1cc11574j
9. [9]
  P. Hendry, Extremophiles: there's more to life, Environ. Chem. 3 (2006) 75-76.
10. [10]
  G. Yuan, K. Hong, H. Lin, Z. She, J. Li, New azalomycin F analogs from mangrove Streptomyces sp. 211726 with activity against microbes and cancer cells, Mar. Drugs 11 (2013) 817-829.
11. [11]
  H.B. Park, J.K. Lee, K.R. Lee, H.C. Kwon, Angumycinones A and B, two new angucyclic quinones from Streptomyces sp. KMC004 isolated from acidic mine drainage, Tetrahedron Lett. 55 (2014) 63-66.
12. [12]
  K. Fujii, Y. Ikai, T. Mayumi. A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: elucidation of limitations of Marfey's method and of its separation mechanism[J]. Anal. Chem., 1997,69:3346-3352. doi: 10.1021/ac9701795
13. [13]
  K. Fujii, Y. Ikai, H. Oka, M. Suzuki, K. Harada. A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: combination of Marfey's method with mass spectrometry and its practical application[J]. Anal. Chem., 1997,69:5146-5151. doi: 10.1021/ac970289b
14. [14]
  H.C. Vervoort, M. Drašković, P. Crews, Histone deacetylase inhibitors as a tool to up-regulate new fungal biosynthetic products: isolation of EGM-556, a cyclodepsipeptide, from Microascus sp., Org. Lett. 13 (2011) 410-413.
15. [15]
  D. Li, G. Carr, Y. Zhang, et al., Turnagainolides A and B, cyclic depsipeptides produced in culture by a Bacillus sp.: isolation, structure elucidation, and synthesis, J. Nat. Prod. 74 (2011) 1093-1099.
16. [16]
  K. Takada, A. Ninomiya, M. Naruse. Surugamides A-E, cyclic octapeptides with four D-amino acid residues, from a marine Streptomyces sp.: LC-MS-aided inspection of partial hydrolysates for the distinction of D- and L-amino acid residues in the sequence[J]. J. Org. Chem., 2013,78:6746-6750. doi: 10.1021/jo400708u
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沈阳化工大学材料科学与工程学院沈阳 110142