Citation: Du Yuqi, Chen Zhengbo, Li Hao, Wang Yi, Fu Peng, Zhu Weiming. Pafuranones A and B, two dimeric polyketides from a rare marine algae-derived fungus Paraconiothyrium sp.[J]. Chinese Chemical Letters, ;2019, 30(5): 981-984. doi: 10.1016/j.cclet.2019.01.034 shu

Pafuranones A and B, two dimeric polyketides from a rare marine algae-derived fungus Paraconiothyrium sp.

Du Yuqi ^a ,
Chen Zhengbo ^a ,
Li Hao ^a ,
Wang Yi ^a ,
Fu Peng ^a,b,*, ,
Zhu Weiming ^a,b,*,

a.
Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts of Pilot National Laboratory for Marine Science and Technology, Qingdao 266003, China

E-mail addresses:

Received Date: 5 January 2019
Revised Date: 28 January 2019
Accepted Date: 31 January 2019
Available Online: 2 May 2019

Figures(8)

Pafuranones A (1) and B (2), a pair of new epimeric polyketide dimers, were isolated from the fungus Paraconiothyrium sp. OUCMDZ-3316 associated with the marine algae Enteromorpha prolifera. Their structures, including absolute configurations, were fully elucidated based on spectroscopic analysis, calculated ECD, and chemical methods. Pafuranones A (1) and B (2) possess a rare dimeric furanone skeleton, which might be formed through a conjugate addition of the monomeric units followed by an intramolecular cyclization.
- Pafuranone,
- Dimer,
- Fungus,
- Paraconiothyrium sp.,
- Enteromorpha prolifera
1. [1]
  (a) A. Debbab, A.H. Aly, W.H. Lin, P. Proksch, Microb. Biotechnol. 3(2010) 544-563;
  (b) H. Zhang, Z. Zhao, H. Wang, Mar. Drugs 15(2017) 68;
  (c) E. Tortorella, P. Tedesco, F.P. Esposito, et al., Mar. Drugs 16(2018) 355.
2. [2]
  (a) J.W. Blunt, A.R. Carroll, B.R. Copp, et al., Nat. Prod. Rep. 35(2018) 8-53;
  (b) J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Nat. Prod. Rep. 34(2017) 235-294;
  (c) J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Nat. Prod. Rep. 33(2016) 382-431;
  (d) J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Nat. Prod. Rep. 32(2015) 116-211;
  (e) J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Nat. Prod. Rep. 31(2014) 160-258;
  (f) J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Nat. Prod. Rep. 30(2013) 237-323;
  (g) J.W. Blunt, B.R. Copp, R.A. Keyzers, et al., Nat. Prod. Rep. 29(2012) 144-222;
  (h) J.W. Blunt, B.R. Copp, M.H.G. Munro, et al., Nat. Prod. Rep. 28(2011) 196-268;
  (i) J.W. Blunt, B.R. Copp, M.H.G. Munro, et al., Nat. Prod. Rep. 27(2010) 165-237;
  (j) J.W. Blunt, B.R. Copp, W.P. Hu, et al., Nat. Prod. Rep. 26(2009) 170-244.
3. [3]
  (a) J. Kjer, A. Debbab, A.H. Aly, P. Proksch, Nat. Protoc. 5(2010) 479-490;
  (b) H. Gao, G. Li, H.-X. Lou, Molecules 23(2018) 646.
4. [4]
  S.K. Deshmukh, M.K. Gupta, V. Prakash, M.S. Reddy, J. Fungi 4(2018) 101. doi: 10.3390/jof4030101
5. [5]
  P. Zhang, X. Li, B.G. Wang, Planta Med. 82(2016) 832-842. doi: 10.1055/s-00000058
6. [6]
  (a) P. Fu, F. Kong, X. Li, Y. Wang, W. Zhu, Org. Lett. 16(2014) 3708-3711;
  (b) C. Wang, L. Guo, J. Hao, L. Wang, W. Zhu, J. Nat. Prod. 79(2016) 2977-2981;
  (c) T. Zhu, Z. Lu, J. Fan, et al., J. Nat. Prod. 81(2018) 2-9;
  (d) Y. Fan, Y. Wang, P. Fu, et al., Org. Chem. Front. 5(2018) 2835-2839.
7. [7]
  (a) K. Sun, G. Zhu, J. Hao, Y. Wang, W. Zhu, Tetrahedron 74(2018) 83-87;
  (b) Y. Du, J. Sun, Q. Gong, et al., J. Agric. Food Chem. 66(2018) 1807-1812.
8. [8]
  C.J. Chen, Y.Q. Zhou, X.X. Liu, et al., Tetrahedron Lett. 56(2015) 6183-6189. doi: 10.1016/j.tetlet.2015.09.079
9. [9]
  M.F. Elsebai, M. Nazir, S. Kehraus, et al., Eur. J. Org. Chem. 2012(2012) 6197-6203. doi: 10.1002/ejoc.201200700
10. [10]
  X. Li, M.K. Kim, U. Lee, et al., Chem. Pharm. Bull. 53(2005) 453-455. doi: 10.1248/cpb.53.453
11. [11]
  M.F. Elsebai, S. Kehraus, U. Lindequist, et al., Org. Biomol. Chem. 9(2011) 802-808. doi: 10.1039/C0OB00625D
12. [12]
  C. Iwamoto, T. Yamada, Y. Ito, K. Minoura, A. Numata, Tetrahedron 57(2001) 2997-3004. doi: 10.1016/S0040-4020(01)00153-3
13. [13]
  A. Numata, C. Takahashi, Y. Ito, et al., J. Chem. Soc. Perkin Trans. 1(3) (1996) 239-245.
14. [14]
  C. Iwamoto, K. Minoura, T. Oka, et al., Tetrahedron 55(1999) 14353-14368. doi: 10.1016/S0040-4020(99)00884-4
15. [15]
  C. Iwamoto, K. Minoura, S. Hagishita, K. Nomoto, A. Numata, Tetrahedron 3(1998) 449-456.
16. [16]
  C. Takahashi, A. Numata, T. Yamada, et al., Tetrahedron Lett. 37(1996) 655-658. doi: 10.1016/0040-4039(95)02225-2
17. [17]
  A. Numata, C. Takahashi, Y. Ito, et al., Tetrahedron Lett. 34(1993) 2355-2358. doi: 10.1016/S0040-4039(00)77612-X
18. [18]
  Z. Chen, J. Hao, L. Wang, et al., Sci. Rep. 6(2016) 20004. doi: 10.1038/srep20004
19. [19]
  H. Liu, Z. Chen, G. Zhu, et al., Tetrahedron 73(2017) 5451-5455. doi: 10.1016/j.tet.2017.07.052
20. [20]
  Y. Li, K.L. Sun, Y. Wang, et al., Chin. Chem. Lett. 24(2013) 1049-1052. doi: 10.1016/j.cclet.2013.07.028
21. [21]
  (a) Y. Shiono, T. Hatakeyama, T. Murayama, T. Koseki, Nat. Prod. Commun. 7(2012) 1065-1068;
  (b) M. Vallet, Q.P. Vanbellingen, T. Fu, et al., J. Nat. Prod. 80(2017) 2863-2873
  (c) T. Fujiwara, A. Sato, Y. Kawamura, K. Matsumoto, H. Itazaki, Patent, JP 6239852, 1994.
22. [22]
  V.H.T. James, J. Chem. Soc. (1955) 637-639. doi: 10.1039/jr9550000637
23. [23]
  K. Weinges, E. Paulus, Eur. J. Org. Chem. 681(1965) 154-161.
24. [24]
  (a) von C. Djerassi, Optical Rotatory Dispersion: Applications to Organic Chemistry, McGraw-Hill, New York, 1960;
  (b) L. Velluz, M.L. Grand, M. Grosjean, Optical Circular, Dichroism: Principles, Measurements, and Applications, Academic Press, New York, 1965;
  (c) S. Lin, T. Shi, K. Chen, et al., Chem. Commun. 47(2011) 10413-10415;
  (d) P. Fu, J.B. MacMillan, Org. Lett. 17(2015) 3046-3049;
  (e) P. Fu, S. La, J.B. MacMillan, J. Nat. Prod. 79(2016) 455-462.
25. [25]
  P.J. Stephens, J.J. Pan, K. Krohn, J. Org. Chem. 72(2007) 7641-7649. doi: 10.1021/jo071183b
26. [26]
  Y.K. Zheng, X.G. Qiao, C.P. Miao, et al., Ann. Microbiol. 66(2016) 529-542. doi: 10.1007/s13213-015-1153-7
27. [27]
  M. Cloete, P.H. Fourie, U. Damm, P.W. Crous, L. Mostert, Phytopathol. Mediterr. 50(2011) 176-190.
28. [28]
  G.J.M. Verkley, M. da Silva, D.T. Wicklow, P.W. Crous, Stud. Mycol. 50(2004) 323-335.
29. [29]
  J.M. Whipps, M. Gerlagh, Mycol. Res. 96(1992) 897-907. doi: 10.1016/S0953-7562(09)80588-1
30. [30]
  U. Damm, G.J.M. Verkley, P.W. Crous, et al., Persoonia 20(2008) 9-17. doi: 10.3767/003158508X286842
31. [31]
  I.E. Mohamed, S. Kehraus, A. Krick, et al., J. Nat. Prod. 73(2010) 2053-2056. doi: 10.1021/np100310k
32. [32]
  C.X. Liu, L. Wang, J.F. Chen, et al., Magn. Reson. Chem. 53(2015) 317-322. doi: 10.1002/mrc.v53.4
33. [33]
  F. Ren, S. Chen, Y. Zhang, et al., J. Nat. Prod. 81(2018) 1752-1759. doi: 10.1021/acs.jnatprod.8b00106
34. [34]
  M.A. Colombier, A. Alanio, B. Denis, et al., J. Clin. Microbiol. 53(2015) 2084-2094. doi: 10.1128/JCM.00295-15
35. [35]
  T. Suzuki, N.R. Ariefta, T. Koseki, et al., Fitoterapia 132(2019) 75-81. doi: 10.1016/j.fitote.2018.11.017
36. [36]
  C. Anisha, P. Sachidanandan, E.K. Radhakrishnan, Curr. Microbiol. 75(2018) 343-352. doi: 10.1007/s00284-017-1387-7
37. [37]
  T.H. Quang, D.C. Kim, P. van Kiem, et al., J. Antibiot. 71(2018) 826-830. doi: 10.1038/s41429-018-0073-8
38. [38]
  N. Cho, T.T. Ransom, J. Sigmund, et al., J. Nat. Prod. 80(2017) 2037-2044. doi: 10.1021/acs.jnatprod.7b00170
39. [39]
  S. Chen, Y. Zhang, C. Zhao, et al., Fitoterapia 99(2014) 236-242. doi: 10.1016/j.fitote.2014.09.021
40. [40]
  S. Chen, Y. Zhang, S. Niu, X. Liu, Y. Che, J. Nat. Prod. 77(2014) 1513-1518. doi: 10.1021/np500302e
41. [41]
  Y. Shiono, M. Kikuchi, T. Koseki, et al., Phytochemistry 72(2011) 1400-1405. doi: 10.1016/j.phytochem.2011.04.016
42. [42]
  X. Li, X. He, L. Hou, et al., Sci. Rep. 8(2018) 7896. doi: 10.1038/s41598-018-26183-0
43. [43]
  H. Forootanfar, M.A. Faramarzi, A.R. Shahverdi, M.T. Yazdi, Bioresour. Technol. 102(2011) 1808-1814. doi: 10.1016/j.biortech.2010.09.043
44. [44]
  Z. Guo, F. Ren, Y. Che, G. Liu, L. Liu, Molecules 20(2015) 14611-14620.
45. [45]
  L. Liu, X. Chen, D. Li, et al., J. Nat. Prod. 78(2015) 746-753. doi: 10.1021/np5009569
46. [46]
  H.Y. Tang, Q. Zhang, Y.Q. Gao, et al., RSC Adv. 5(2015) 2185-2190. doi: 10.1039/C4RA11712C
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4. [4]
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