The Bioactive Secondary Metabolites from Talaromyces species

doi:10.1007/s13659-015-0081-3

应用天然产物 ›› 2016, Vol. 6 ›› Issue (1): 1-24.DOI: 10.1007/s13659-015-0081-3

• Review • 下一篇

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 Wu^1,2

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

收稿日期:2015-11-16 修回日期:2015-12-07 出版日期:2016-02-24 发布日期:2018-02-08
通讯作者: Quan-Xiang Wu,e-mail:wuqx@lzu.edu.cn
基金资助:
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)

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 Wu^1,2

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

Received:2015-11-16 Revised:2015-12-07 Online:2016-02-24 Published:2018-02-08
Supported by:
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)

摘要/Abstract

摘要： 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.

关键词: Talaromyces, Secondary metabolites, Biological activities

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.

Key words: Talaromyces, Secondary metabolites, Biological activities

Ming-Ming Zhai, Jie Li, Chun-Xiao Jiang, Yan-Ping Shi, Duo-Long Di, Phillip Crews, Quan-Xiang Wu. The Bioactive Secondary Metabolites from Talaromyces species[J]. 应用天然产物, 2016, 6(1): 1-24.

Ming-Ming Zhai, Jie Li, Chun-Xiao Jiang, Yan-Ping Shi, Duo-Long Di, Phillip Crews, Quan-Xiang Wu. The Bioactive Secondary Metabolites from Talaromyces species[J]. Natural Products and Bioprospecting, 2016, 6(1): 1-24.

参考文献

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)

[1]	Olusesan Ojo, Idris Njanje, Dele Abdissa, Tarryn Swart, Roxanne L. Higgitt, Rosemary A. Dorrington. Newly isolated terpenoids (covering 2019-2024) from Aspergillus species and their potential for the discovery of novel antimicrobials[J]. 应用天然产物, 2025, 15(2): 19-19.
[2]	Ismail Ware, Katrin Franke, Andrej Frolov, Kseniia Bureiko, Elana Kysil, Maizatulakmal Yahayu, Hesham Ali El Enshasy, Ludger A. Wessjohann. Comparative metabolite analysis of Piper sarmentosum organs approached by LC-MS-based metabolic profiling[J]. 应用天然产物, 2024, 14(4): 30-30.
[3]	Weiwei Peng, Qi Huang, Xin Ke, Wenxuan Wang, Yan Chen, Zihuan Sang, Chen Chen, Siyu Qin, Yuting Zheng, Haibo Tan, Zhenxing Zou. Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5[J]. 应用天然产物, 2024, 14(1): 8-8.
[4]	Kritika Jalota, Vikas Sharma, Chiti Agarwal, Suruchi Jindal. Eco-friendly approaches to phytochemical production: elicitation and beyond[J]. 应用天然产物, 2024, 14(1): 5-5.
[5]	Jin-Ning Chu, Premanand Krishnan, Kuan-Hon Lim. A comprehensive review on the chemical constituents, sesquiterpenoid biosynthesis and biological activities of Sarcandra glabra[J]. 应用天然产物, 2023, 13(6): 53-53.
[6]	Muhammad Rashad, Simone Sampò, Amelia Cataldi, Susi Zara. Biological activities of gastropods secretions: snail and slug slime[J]. 应用天然产物, 2023, 13(6): 42-42.
[7]	Li Wu, Ning Yang, Meng Guo, Didi Zhang, Reza A. Ghiladi, Hasan Bayram, Jun Wang. The role of sound stimulation in production of plant secondary metabolites[J]. 应用天然产物, 2023, 13(6): 40-40.
[8]	Fengli Li, Saisai Gu, Sitian Zhang, Shuyuan Mo, Jieru Guo, Zhengxi Hu, Yonghui Zhang. Three new amide derivatives from the fungus Alternaria brassicicola[J]. 应用天然产物, 2023, 13(4): 28-28.
[9]	Jin-Tao Ma, Da-Wei Li, Ji-Kai Liu, Juan He. Advances in Research on Chemical Constituents and Their Biological Activities of the Genus Actinidia[J]. 应用天然产物, 2021, 11(6): 573-609.
[10]	Ke Ye, Hong-Lian Ai, Ji-Kai Liu. Identification and Bioactivities of Secondary Metabolites Derived from Endophytic Fungi Isolated from Ethnomedicinal Plants of Tujia in Hubei Province: A Review[J]. 应用天然产物, 2021, 11(2): 185-205.
[11]	Xingrong Peng, Minghua Qiu. Meroterpenoids from Ganoderma Species: A Review of Last Five Years[J]. 应用天然产物, 2018, 8(3): 137-149.
[12]	Rong Chen, Jian-Wei Tang, Xing-Ren Li, Miao Liu, Wen-Ping Ding, Yuan-Fei Zhou, Wei-Guang Wang, Xue Du, Han-Dong Sun, Pema-Tenzin Puno. Secondary Metabolites from the Endophytic Fungus Xylaria sp. Hg1009[J]. 应用天然产物, 2018, 8(2): 121-129.
[13]	Li-Wen Tian, Zhen Zhang, Hai-Lan Long, Ying-Jun Zhang. Steroidal Saponins from the Genus Smilax and Their Biological Activities[J]. 应用天然产物, 2017, 7(4): 283-298.
[14]	Fidele Ntie-Kang, Leonel E. Njume, Yvette I. Malange, Stefan Günther, Wolfgang Sippl, Joseph N. Yong. The Chemistry and Biological Activities of Natural Products from Northern African Plant Families: From Taccaceae to Zygophyllaceae[J]. 应用天然产物, 2016, 6(2): 63-96.
[15]	Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler. Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)[J]. 应用天然产物, 2015, 5(3): 167-173.

The Bioactive Secondary Metabolites from Talaromyces species

The Bioactive Secondary Metabolites from Talaromyces species

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价