Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.

doi:10.1007/s13659-015-0067-1

Natural Products and Bioprospecting ›› 2015, Vol. 5 ›› Issue (4): 195-203.DOI: 10.1007/s13659-015-0067-1

• Original article • Previous Articles Next Articles

Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.

Hao Wen¹, Yan Li², Xingzhong Liu³, Wencai Ye¹, Xinsheng Yao¹, Yongsheng Che²

1. Institute of Traditional Chinese Medicine&Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China;
2. State Key Laboratory of Toxicology&Medical Countermeasures, Beijing Institute of Pharmacology&Toxicology, Beijing 100850, People's Republic of China

Received:2015-08-09 Revised:2015-08-10 Online:2018-02-11 Published:2015-08-24
Supported by:
We gratefully acknowledge financial support from the National Natural Science Foundation of China(81273395) and the National Program of Drug Research and Development(2012ZX09301-003).

Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.

Hao Wen¹, Yan Li², Xingzhong Liu³, Wencai Ye¹, Xinsheng Yao¹, Yongsheng Che²

1. Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China;
2. State Key Laboratory of Toxicology & Medical Countermeasures, Beijing Institute of Pharmacology & Toxicology, Beijing 100850, People's Republic of China;State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, People's Republic of China

通讯作者: Xin-Sheng Yao,e-mail:tyaoxs@jnu.edu.cn;Yong-Sheng Che,e-mail:cheys@im.ac.cn
基金资助:
We gratefully acknowledge financial support from the National Natural Science Foundation of China(81273395) and the National Program of Drug Research and Development(2012ZX09301-003).

Abstract

Abstract: Fusagerins A-F(1-6), six new alkaloids including a unique one with the rare a-(N-formyl) carboxamide moiety(1), a hydantoin(imidazolidin-2, 4-dione) derivative(2), and four fungerin analogues(3-6), were isolated from the crude extract of the fungus Fusarium sp. , together with the known compound fungerin(7). Compound 2 was isolated as a racemate and further separated into two enantiomers on a chiral HPLC column. The structures of 1-6 were determined mainly by NMR experiments, and the absolute configuration of 1 and 2 was assigned by electronic circular dichroism(ECD) calculations. Compound 7 showed antibacterial activity against Staphylococcus aureus and Streptococcus pneumoniae, and weak cytotoxicity against the T24 cells.

Key words: Fusarium sp., Alkaloids, Structure elucidation, Configuration determination

摘要： Fusagerins A-F(1-6), six new alkaloids including a unique one with the rare a-(N-formyl) carboxamide moiety(1), a hydantoin(imidazolidin-2, 4-dione) derivative(2), and four fungerin analogues(3-6), were isolated from the crude extract of the fungus Fusarium sp. , together with the known compound fungerin(7). Compound 2 was isolated as a racemate and further separated into two enantiomers on a chiral HPLC column. The structures of 1-6 were determined mainly by NMR experiments, and the absolute configuration of 1 and 2 was assigned by electronic circular dichroism(ECD) calculations. Compound 7 showed antibacterial activity against Staphylococcus aureus and Streptococcus pneumoniae, and weak cytotoxicity against the T24 cells.

关键词: Fusarium sp., Alkaloids, Structure elucidation, Configuration determination

Hao Wen, Yan Li, Xingzhong Liu, Wencai Ye, Xinsheng Yao, Yongsheng Che. Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.[J]. Natural Products and Bioprospecting, 2015, 5(4): 195-203.

Hao Wen, Yan Li, Xingzhong Liu, Wencai Ye, Xinsheng Yao, Yongsheng Che. Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.[J]. 应用天然产物, 2015, 5(4): 195-203.

References

1. T. Henkel, R. Brunne, H. Müller, F. Reichel, Angew. Chem. Int. Ed. 38, 643-647 (1999)
2. J.B. Gloer, Acc. Chem. Res. 28, 343-350 (1995)
3. J.B. Gloer, in The Mycota IV:Environmental and Microbial Relationships, ed. by D.T. Wicklow, B. Soderstrom (SpringerVerlag, Berlin, 1997), pp. 249-268
4. J. Meinwald, T. Eisner, Proc. Natl. Acad. Sci. USA 105, 4539-4540 (2008)
5. Y. Che, Int. J. Pharm. Res. 38, 12-27 (2011)
6. H. Guo, H. Hu, S. Liu, X. Liu, Y. Zhou, Y. Che, J. Nat. Prod. 70, 1519-1521 (2007)
7. Y. Zhang, S. Liu, X. Liu, Y. Che, J. Nat. Prod. 70, 1522-1525 (2007)
8. Y. Zhang, S. Liu, H. Liu, X. Liu, Y. Che, J. Nat. Prod. 72, 1364-1367 (2009)
9. E. Li, F. Zhang, S. Niu, X. Liu, G. Liu, Y. Che, Org. Lett. 14, 3320-3323 (2012)
10. J. Lin, S. Liu, B. Sun, S. Niu, E. Li, X. Liu, Y. Che, J. Nat. Prod. 73, 905-910 (2010)
11. C. Ma, Y. Li, S. Niu, H. Zhang, X. Liu, Y. Che, J. Nat. Prod. 74, 32-37 (2011)
12. J. Ren, F. Zhang, X. Liu, L. Li, G. Liu, X. Liu, Y. Che, Org. Lett. 14, 6226-6229 (2012)
13. S. Chen, F. Ren, S. Niu, X. Liu, Y. Che, J. Nat. Prod. 77, 9-14 (2014)
14. Y. Kato, H. Koshino, J. Uzawa, K. Anzai, Biosci. Biotech. Biochem. 60, 2081-2083 (1996)
15. R. Silverstein, G. Bassler, T. Morrill, Spectrometric Identification of Organic Compounds, 5th edn. (Wiley, Chichester, 1991)
16. R. Keyzers, C. Gray, M. Schleyer, C. Whibley, D. Hendricks, M. Davies-Coleman, Tetrahedron 62, 2200-2206 (2006)
17. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. Hratchian, A. Izmaylov, J. Bloino, G. Zheng, J. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. Montgomery, J. Peralta, F. Ogliaro, M. Bearpark, J. Heyd, E. Brothers, K.N. Kudin, V. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A. 01, 5th edn. (Gaussian, Inc., Wallingford, 2009)
18. M. Ono, T. Tsuru, H. Abe, M. Eto, M. Okawa, F. Abe, J. Kinjo, T. Ikeda, T. Nohara, J. Nat. Prod. 69, 1417-1420 (2006)
19. S. Homhual, N. Bunyapraphatsara, T. Kondratyuk, A. Herunsalee, W. Chaukul, J. Pezzuto, H. Fong, H. Zhang, J. Nat. Prod. 69, 421-424 (2006)
20. E. Li, L. Jiang, L. Guo, H. Zhang, Y. Che, Bioorg. Med. Chem. 16, 7894-7899 (2008)
21. G. Ding, Y. Li, S. Fu, S. Liu, J. Wei, Y. Che, J. Nat. Prod. 72, 182-186 (2009)
22. K. Friedrich, M. Zamkanei, R. Zimmer, J. Prakt. Chem. 38, 404-408 (2000)
23. H. Biltz, Ber. Dtsch. Ges. Chem. 1908, 1379-1393
24. H. Merritt, T. Putnam, Arch. Neurol. Psychiatry 39, 1003-1015 (1938)
25. C. López, G. Trigo, in Advances in Heterocyclic Chemistry, vol. 38, ed. by C. Brown, R. Davidson (Academic Press, New York, 1985), pp. 177-228
26. P. Back, P. Maurois, C. Dupont, N. Pages, J. Stables, P. Gressens, P. Evrard, J. Neurosci. 18, 4363-4373 (1998)
27. T. Rodgers, M. LaMontagne, A. Markovac, A. Ash, J. Med. Chem. 20, 591-594 (1977)
28. A. Khodair, Carbohydr. Res. 306, 567-573 (1998)
29. R. Comber, R. Reynolds, J. Friedrich, R. Manguikian, R. Buckheit, J. Truss, W. Shannon, J. Secrist, J. Med. Chem. 35, 3567-3572 (1992)
30. J. Knabe, J. Baldauf, A. Ahlhelm, Pharmazie 52, 912-919 (1997)
31. J. Menéndez, M. Díaz, C. Bellver, M. Sollhuber, Eur. J. Med. Chem. 27, 61-66 (1992)
32. M. Tompkins, J. Med. Chem. 29, 855-859 (1986)
33. K. Kieć-Kononowicz, E. Szymańska, Il Farmaco 57, 909-916 (2002)
34. J. Marton, J. Enis, S. Hosztafi, T. Tímar, J. Agric. Food Chem. 41, 148-152 (1993)
35. G. Chen, Y. Lin, L. Vrijmoed, W. Fong, Chem. Nat. Compd. 42, 138-141 (2006)
36. T. Liu, Z. Li, Y. Wang, L. Tian, Y. Pei, H. Hua, Nat. Prod. Res. 25, 1596-1599 (2011)
37. H. Brastianos, E. Vottero, B. Patrick, R. Soest, T. Matainaho, A. Mauk, R. Andersen, J. Am. Chem. Soc. 128, 16046-16047 (2006)
38. M. Tsuda, T. Yasuda, E. Fukushi, J. Kawabata, M. Sekiguchi, J. Fromont, J. Kobayashi, Org. Lett. 8, 4235-4238 (2006)
39. S. Carmelya, M. Llanb, Y. Kashmana, Tetrahedron 45, 2193-2200 (1989)
40. G. Chan, S. Mong, M. Hemling, A. Freyer, P. Offen, C. DeBrosse, H. Sarau, J. Westley, J. Nat. Prod. 56, 116-121 (1993)
41. K. Alvi, B. Peters, H. Lisa, C. Phillip, Tetrahedron 49, 329-336 (1993)
42. I. Mancini, G. Guella, C. Debitus, F. Pietra, Helv. Chim. Acta 78, 1178-1184 (1995)
43. A. Plubrukarn, D. Smith, R. Cramer, B. Davidson, J. Nat. Prod. 60, 712-715 (1997)
44. B. Copp, C. Fairchild, L. Cornell, A. Casazza, S. Robinson, C. Ireland, J. Med. Chem. 41, 3909-3911 (1998)
45. X. Fu, F. Schmitz, R. Tanner, M. Kelly-Borges, J. Nat. Prod. 61, 384-386 (1998)
46. H. Gross, S. Kehraus, G. Konig, G. Woerheide, A. Wright, J. Nat. Prod. 65, 1190-1193 (2002)
47. S. Tsukamoto, T. Kawabata, H. Kato, T. Ohta, H. Rotinsulu, R. Mangindaan, R. van Soest, K. Ukai, H. Kobayashi, M. Namikoshi, J. Nat. Prod. 70, 1658-1660 (2007)
48. N. Cachet, G. Genta-Jouve, E. Regalado, R. Mokrini, P.G. Amade, G. Culioli, O. Thomas, J. Nat. Prod. 72, 1612-1615 (2009)
49. H. Kang, W. Fenical, Tetrahedron Lett. 37, 2369-2372 (1996)
50. A. Visconti, M. Solfrizzo, J. Agric. Food Chem. 42, 195-199 (1994)
51. R. Uchida, R. Imasato, Y. Yamaguchi, R. Masuma, K. Shiomi, H. Tomoda, S. Ōmura, J. Antibiot. 58, 804-809 (2005)
52. N. Zhang, Y. Chen, R. Jiang, E. Li, X. Chen, Z. Xi, Y. Guo, X. Liu, Y. Zhou, Y. Che, X. Jiang, Autophagy 7, 598-612 (2011)

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Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.

Fusagerins A-F, New Alkaloids from the Fungus Fusarium sp.

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