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The Bioactive Secondary Metabolites from Talaromyces species |
Ming-Ming Zhai1, Jie Li1, Chun-Xiao Jiang1, Yan-Ping Shi2, Duo-Long Di2, Phillip Crews3, Quan-Xiang Wu1,2 |
1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China; 2. Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China; 3. Department of Chemistry and Biochemistry, University of California Santa Cruz, Santa Cruz, CA 95064, USA |
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Abstract The focus of this review is placed on the chemical structures from the species of the genus Talaromyces reported with reference to their biological activities. 221 secondary metabolites, including 43 alkaloids and peptides, 88 esters, 31 polyketides, 19 quinones, 15 steroid and terpenoids, and 25 other structure type compounds, have been included, and 66 references are cited.
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Keywords
Talaromyces
Secondary metabolites
Biological activities
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Fund:Authors are thankful to financially supporting by the National Natural Science Foundation of China (Nos.21202075 and 21272103),the 111 Project,the Scientific Research Foundation for Returned Overseas Students (No.45);the Scientific Research Ability Training of Undergraduate Students Majoring in Chemistry by the Two Patters Based on the Tutorial System and Top Students Project (J1103307) |
Issue Date: 08 February 2018
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1. J. Pitt, in Penicillium and Talaromyces:Introduction, Penicillium, Encyclopedia of Food Microbiology (2nd edn) (2014), pp. 6-13 2. N.E.A. El-Naggar, S.A. Haroun, E.A. Oweis, A.A. Sherief, Prep. Biochem. Biotechnol. 45(7), 712-729 (2015) 3. B. Proksa, Chem. Pap. 64(6), 696-714 (2010) 4. Y.S. Chu, X.M. Niu, Y.L. Wang, J.P. Guo, W.Z. Pan, X.W. Huang, K.Q. Zhang, Org. Lett. 12(19), 4356-4359 (2010) 5. J.P. Guo, J.L. Tan, Y.L. Wang, H.Y. Wu, C.P. Zhang, X.M. Niu, W.Z. Pan, X.W. Huang, K.Q. Zhang, J. Nat. Prod. 74(10), 2278-2281 (2011) 6. H.B. Yang, F. Li, N.Y. Ji, Chin. J. Oceanol. Limnol. (2015). doi:10.1007/s00343-015-4316-2 7. M.M. Zhai, H.T. Niu, J. Li, H. Xiao, Y.P. Shi, D.L. Di, P. Crews, Q.X. Wu, J. Agric. Food Chem. 63(43), 9558-9564 (2015) 8. J.P. Guo, C.Y. Zhu, C.P. Zhang, Y.S. Chu, Y.L. Wang, J.X. Zhang, D.K. Wu, K.Q. Zhang, X.M. Niu, J. Am. Chem. Soc. 134(50), 20306-20309 (2012) 9. X.M. Niu, L. Chen, Q. Yue, B.L. Wang, J.X. Zhang, C.Y. Zhu, K.Q. Zhang, G.F. Bills, Z.Q. An, Org. Lett. 16(14), 3744-3747 (2014) 10. S. Suzuki, T. Hosoe, K. Nozawa, K.I. Kawai, T. Yaguchi, S.I. Udagawa, J. Nat. Prod. 63(6), 768-772 (2000) 11. S. Ngokpol, W. Suwakulsiri, S. Sureram, K. Lirdprapamongkol, T. Aree, S. Wiyakrutta, C. Mahidol, S. Ruchirawat, P. Kittakoop, Mar. Drugs 13(6), 3567-3580 (2015) 12. T. Dethoup, L. Manoch, A. Kijjoa, M. Pinto, L. Gales, A.M. Damas, A.M.S. Silva, G. Eaton, W. Herz, J. Nat. Prod. 70(7), 1200-1202 (2007) 13. R. Bara, A.H. Aly, V. Wray, W.H. Lin, P. Proksch, A. Debbab, Tetrahedron Lett. 54(13), 1686-1689 (2013) 14. T. Morino, M. Nishimoto, A. Masuda, S. Fujita, T. Nishikiori, S. Saito, J. Antibiot. 48(12), 1509-1510 (1995) 15. F. Miao, R. Yang, D.D. Chen, Y. Wang, B.F. Qin, X.J. Yang, L. Zhou, Molecules 17(12), 14091-14098 (2012) 16. S.I. Komai, T. Hosoe, T. Itabashi, K. Nozawa, K. Okada, G.M. de Campos Takaki, M. Chikamori, T. Yaguchi, K. Fukushima, M. Miyaji, K.I. Kawai, Mycotoxins 54(1), 15-19 (2004) 17. Y.S. Dong, J.S. Yang, H. Zhang, J. Lin, X. Ren, M. Liu, X.H. Lu, J.G. He, J. Nat. Prod. 69(1), 128-130 (2006) 18. D. Jones, H.A. Anderson, J.D. Russell, A.R. Fraser, Trans. Br. Mycol. Soc. 83(4), 718-721 (1984) 19. J.W. He, Z.Q. Mu, H. Gao, G.D. Chen, Q. Zhao, D. Hu, J.Z. Sun, X.X. Li, Y. Li, X.Z. Liu, X.S. Yao, Tetrahedron 70(29), 4425-4430 (2014) 20. H.Y. Wang, M. Alai, H. Tomoda, S. Omura, Chin. J. Antibiot. 26(2), 89-93 (2001) 21. M. Aral, H. Tomoda, T. Okuda, H.Y. Wang, N. Tabata, R. Masuma, Y. Yamaguchi, S. Ōmura, J. Antibiot. 55(2), 172-180 (2002) 22. C.H. Sun, M. Alai, H. Tomoda, S. Omura, Chin. J. Antibiot. 27(2), 80-83 (2002) 23. G. Schlingmann, L. Milne, G.T. Carter, Tetrahedron 58(34), 6825-6835 (2002) 24. M. Yamazaki, E. Okuyama, Chem. Pharm. Bull. 28(12), 3649-3655 (1980) 25. T. Dethoup, L. Manoch, A. Kijjoa, M.S.J. Nascimento, P. Puaparoj, A.M.S. Silva, G. Eaton, W. Herz, Planta Med. 72(10), 957-960 (2006) 26. B. Wu, B. Ohlendorf, V. Oesker, J. Wiese, S. Malien, R. Schmaljohann, J.F. Imhoff, Mar. Biotechnol. 17(1), 110-119 (2015) 27. K. Suzuki, K. Nozawa, S. Nakajima, S.I. Udagawa, K.I. Kawai, Chem. Pharm. Bull. 40(5), 1116-1119 (1992) 28. M. Kawaguchi, R. Uchida, S. Ohte, N. Miyachi, K. Kobayashi, N. Sato, K. Nonaka, R. Masuma, T. Fukuda, T. Yasuhara, H. Tomoda, J. Antibiot. 66(3), 179-189 (2013) 29. K. Suzuki, K. Nozawa, S.I. Udagawa, S. Nakajima, K.I. Kawai, Phytochemistry 30(6), 2096-2098 (1991) 30. W.A. Ayer, J.S. Racok, Can. J. Chem. 68(11), 2085-2094 (1990) 31. J.W. He, D.P. Qin, H. Gao, R.Q. Kuang, Y. Yu, X.Z. Liu, X.S. Yao, Molecules 19(12), 20880-20887 (2014) 32. H. Hayadhi, Y. Oka, K. Kai, K. Akiyama, Biosci. Biotechnol. Biochem. 76(4), 745-748 (2012) 33. H. Hayadhi, Y. Oka, K. Kai, K. Akiyama, Biosci. Biotechnol. Biochem. 76(9), 1765-1768 (2012) 34. W.A. Ayer, J.S. Racok, Can. J. Chem. 68(11), 2095-2101 (1990) 35. M. Kumar, M. Qadri, P.R. Sharma, A. Kumar, S.S. Andotra, T. Kaur, K. Kapoor, V.K. Gupta, R. Kant, A. Hamid, S. Johri, S.C. Taneja, R.A. Vishwakarma, S. Riyaz-Ul-Hassan, B.A. Shah, J. Nat. Prod. 76(2), 194-199 (2013) 36. T. Tomikawa, K. Shin-Ya, K. Furihata, T. Kinoshita, A. Miyajima, H. Seto, Y. Hayakawa, J. Antibiot. 53(8), 848-850 (2000) 37. Y.S. Dong, J. Lin, X.H. Lu, Z.H. Zheng, X. Ren, H. Zhang, J.G. He, J.S. Yang, Helv. Chim. Acta 92(3), 567-574 (2009) 38. S. Kaifuchi, M. Mori, K. Nonaka, R. Masuma, S. Ōmura, K. Shiomi, J. Gen. Appl. Microbiol. 61(2), 57-62 (2015) 39. K. Nonaka, T. Chiba, T. Suga, Y. Asami, M. Iwatsuki, R. Masuma, S. Ōmura, K. Shiomi, J. Antibiot. 68(8), 530-532 (2015) 40. D. Kumla, T. Dethoup, S. Buttachon, N. Singburaudom, A.M.S. Silva, A. Kijjoa, Nat. Prod. Comm. 9(8), 1147-1150 (2014) 41. H. Fujimoto, Y. Jisai, Y. Horie, M. Yamazaki, Mycotoxins 27, 15-19 (1988) 42. H. Matsunaga, S. Kamisuki, M. Kaneko, Y. Yamaguchi, T. Takeuchi, K. Watashi, F. Sugawara, Bioorg. Med. Chem. Lett. 25(19), 4325-4328 (2015) 43. F. Liu, X.L. Cai, H. Yang, X.K. Xia, Z.Y. Guo, J. Yuan, M.F. Li, Z.G. She, Y.C. Lin, Planta Med. 76(2), 185-189 (2010) 44. H.H.F. Koolen, L.S. Menezes, M.P. Souza, F.M.A. Silva, F.G.O. Almeida, A.Q.L. de Souza, A. Nepel, A. Barison, F.H. da Silva, D.E. Evangelista, A.D.L. de Souza, J. Braz. Chem. Soc. 24(5), 880-883 (2013) 45. H. Fujimoto, T. Matsudo, A. Yamaguchi, M. Yamazaki, Heterocycles 30(1), 607-616 (1990) 46. E. Yoshida, H. Fujimoto, M. Yamazaki, Chem. Pharm. Bull. 44(2), 284-287 (1996) 47. T. Kimura, M. Nishida, K. Kuramochi, F. Sugawara, H. Yoshida, Y. Mizushina, Bioorg. Med. Chem. 16(8), 4594-4599 (2008) 48. L.Q. Li, Y.G. Yang, Y. Zeng, C. Zou, P.J. Zhao, Molecules 15(6), 3993-3997 (2010) 49. R. Bara, A.H. Aly, A. Pretsch, V. Wray, B.G. Wang, P. Proksch, A. Debbab, J. Antibiot. 66(8), 491-493 (2013) 50. H.E. Ding, Z.D. Yang, L. Sheng, S.Y. Zhou, S. Li, X.J. Yao, K.K. Zhi, Y.G. Wang, F. Zhang, Tetrahedron Lett. 56(48), 6754-6757 (2015) 51. K. Nozawa, R. Saito, S.I. Udagawa, S. Nakajima, K.I. Kawai, Phytochemistry 39(3), 719-721 (1995) 52. E. Yoshida, H. Fujimoto, M. Baba, M. Yamazaki, Chem. Pharm. Bull. 43(8), 1307-1310 (1995) 53. Y. Tabata, S. Ikegami, T. Yaguchi, T. Sasaki, S. Hoshiko, S. Sakuma, K. Shin-Ya, H. Seto, J. Antibiot. 52(4), 412-414 (1999) 54. S. Natori, F. Sato, S.I. Udagawa, Chem. Pharm. Bull. 13(3), 385-386 (1965) 55. G.W. van Eijk, Experientia 29(5), 522-523 (1973) 56. R. Bara, I. Zerfass, A.H. Aly, H. Goldbach-Gecke, V. Raghavan, P. Sass, A. Mandi, V. Wray, P.L. Polavarapu, A. Pretsch, W.H.Lin, T. Kurtan, A. Debbab, H. Brotz-Oesterhelt, P. Proksch, J. Med. Chem. 56(8), 3257-3272 (2013) 57. L.Q. Li, Y.G. Yang, Y. Zeng, C. Zou, P.J. Zhao, Guangxi Zhiwu 31(5), 699-701 (2011) 58. J.W. He, H.X. Liang, H. Gao, R.Q. Kuang, G.D. Chen, D. Hu, C.X. Wang, X.Z. Liu, Y. Li, X.S. Yao, J. Asian Nat. Prod. Res. 16(10), 1029-1034 (2014) 59. H.X. Li, H.B. Huang, C.L. Shao, H.R. Huang, J.Y. Jiang, X. Zhu, Y.Y. Liu, L. Liu, Y.J. Lu, M.F. Li, Y.C. Lin, Z.G. She, J. Nat. Prod. 74(5), 1230-1235 (2011) 60. N.J. Phillips, R.J. Cole, D.G. Lynn, Tetrahedron Lett. 28(15), 1619-1622 (1987) 61. H. Shiozawa, M. Takahashi, T. Takatsu, T. Kinoshita, K. Tanzawa, T. Hosoya, K. Furuya, S. Takahashi, J. Antibiot. 48(5), 357-362 (1995) 62. S.B. Singh, H. Jayasuriya, R. Dewey, J.D. Polishook, A.W. Dombrowski, D.L. Zink, Z.Q. Guan, J. Collado, G. Platas, F. Pelaez, P.J. Felock, D.J. Hazuda, J. Ind. Microbiol. Biotechnol. 30(12), 721-731 (2003) 63. F. Liu, Q. Li, H. Yang, X.L. Cai, X.K. Xia, S.P. Chen, M.F. Li, Z.G. She, Y.C. Lin, Magn. Reson. Chem. 47(5), 453-455 (2009) 64. K. Nozawa, M. Takada, S.I. Udagawa, S. Nakajima, K.I. Kawai, Phytochemistry 28(2), 655-656 (1989) 65. M. Takeuchi, M. Nakajima, T. Ogita, M. Inukai, K. Kodama, K. Furuya, H. Nagaki, T. Haneishi, J. Antibiot. 42(2), 198-205 (1989) 66. K. Mizuno, A. Yagi, M. Takada, K. Matsuura, K. Yamaguchi, K. Asano, J. Antibiot. 27(7), 560-563 (1974) |
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