ORIGINAL ARTICLES |
|
|
|
|
|
Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66 |
Xiao-Zheng Su1,2,3, Jian-Wei Tang1,2, Kun Hu1,2, Xiao-Nian Li1,2, Han-Dong Sun1,2, Pema-Tenzin Puno1,2 |
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China; 2 Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China; 3 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China |
|
|
Abstract Arthrinins E-G (1-3), three new sesquiterpenoids possessing non-isoprenoid botryane skeleton, were isolated from the fermentation of an endophytic fungus named Arthrinium sp. HS66 which colonized in the stems of Isodon xerophilus. Their structures were determined by extensive spectroscopic methods. Furthermore, the structure of 1 was unambiguously confirmed by X-ray diffraction, while those of 2 and 3 were verified through quantum chemical calculation of NMR data and ECD spectra.
|
Keywords
Isodon xerophilus
Endophytic fungus
Arthrinium
Botryane sesquiterpenoid
Quantum chemical calculation
|
Fund:This project was supported financially by the National Natural Science Foundation of China (No. 81874298), the CAS "Light of West China" program (Pema-Tenzin Puno), and the Yunnan Science Fund for Distinguished Young Scholars (2019FJ002). |
Corresponding Authors:
Pema-Tenzin Puno
E-mail: punopematenzin@mail.kib.ac.cn
|
Issue Date: 19 August 2020
|
|
|
1. M. Barbero, E. Artuso, C. Prandi, Curr. Med. Chem. 25, 141-185 (2018) 2. H.W. Fehlhaber, R. Geipel, H.J. Mercker, R. Tschesche, K. Welmar, F. Schoenbeck, Chem. Ber. 107, 1720-1730 (1974) 3. T. Kimata, M. Natsume, S. Marumo, Tetrahedron Lett. 26, 2097-2100 (1985) 4. X.D. Qin, H.J. Shao, Z.J. Dong, J.K. Liu, J. Antibiot. 61, 556-562 (2008) 5. R.P. Medina, A.R. Araujo, J.M. Batista, C.L. Cardoso, C. Seidl, A.F.L. Vilela, H.V. Domingos, L.V. Costa-Lotufo, R.J. Andersen, D.H.S. Silva, Sci. Rep. 9, 12318 (2019) 6. Y.F. Yuan, Y. Feng, F.X. Ren, S.B. Niu, X.Z. Liu, Y.S. Che, Org. Lett. 15, 6050-6053 (2013) 7. F.R. Rossi, A. Garriz, M. Marina, F.M. Romero, M.E. Gonzalez, I.G. Collado, F.L. Pieckenstain, Mol. Plant Microbe Interact. 24, 888-896 (2011) 8. N. Temme, B. Oeser, M. Massaroli, J. Heller, A. Simon, I.G. Collado, M. Viaud, P. Tudzynski, Mol. Plant Pathol. 13, 704-718 (2012) 9. K. Krohn, J.Q. Dai, U. Florke, H.J. Aust, S. Drager, B. Schulz, J. Nat. Prod. 68, 400-405 (2005) 10. C.Q. Liang, Y.M. Shi, X.Y. Li, R.H. Luo, Y.E. Kuhnert, F. Surup, V. Wiebach, S. Bernecker, M. Stadler, Phytochemistry 117, 116-122 (2015) 11. R. Duran-Patron, R. Hernandez-Galin, L.G. Rebordinos, J.M. Cantoral, I.G. Collado, Tetrahedron 55, 2389-2400 (1999) 12. C. Qiao, W. Zhang, J.C. Han, C.C. Li, Org. Lett. 18, 4932-4935 (2016) 13. C. Qiao, W. Zhang, J.C. Han, W.M. Dai, C.C. Li, Tetrahedron 75, 1739-1745 (2019) 14. J.R. Hanson, R. Nyfeler, J. Chem. Soc., Chem. Commun. 72-73 (1976) 15. I.G. Collado, A.J.M. Sanchez, J.R. Hanson, Nat. Prod. Rep. 24, 674-686 (2007) 16. J. Moraga, B. Dalmais, I. Izquierdo-Bueno, J. Aleu, J.R. Hanson, R. Hernandez-Galan, M. Viaud, I.G. Collado, ACS Chem Biol. 11, 2838-2846 (2016) 17. R.M.K. Toghueo, Nat. Prod. Bioprospect. 9, 311-328 (2019) 18. J.W. Tang, L.M. Kong, W.Y. Zu, K. Hu, X.N. Li, B.C. Yan, W.G. Wang, H.D. Sun, Y. Li, P.T. Puno, Org. Lett. 21, 771-775 (2019) 19. B.C. Yan, W.G. Wang, D.B. Hu, X. Sun, L.M. Kong, X.N. Li, X. Du, S.H. Luo, Y. Liu, Y. Li, H.D. Sun, J.X. Pu, Org. Lett. 18, 1108-1111 (2016) 20. B.S. Chen, E.W. Li, L. Liu, M.F. Liao, Z.X. Zhu, W.Y. Zhuang, L. Bao, H.W. Liu, Planta Med. 84, 1055-1063 (2018) 21. S.S. Ebada, B. Schulz, V. Wray, F. Totzke, M.H.G. Kubbutat, W.E.G. Mueller, A. Hamacher, M.U. Kassack, W. Lin, P. Proksch, Bioorg. Med. Chem. 19, 4644-4651 (2011) 22. T. Feng, Z.H. Li, Z.J. Dong, J. Su, Y. Li, J.K. Liu, Nat. Prod. Bioprospect. 1, 29-32 (2011) 23. Y.R. Bao, G.D. Chen, H. Gao, R.R. He, Y.H. Wu, X.X. Li, D. Hu, C.X. Wang, X.Z. Liu, Y. Li, X.S. Yao, RSC Adv. 5, 46252-46259 (2015) 24. Z.H. Gao, L.M. Kong, X.S. Zou, Y.M. Shi, S.Z. Shang, H.R. Luo, C.Q. Liang, X.N. Li, Y. Li, X. Du, W.L. Xiao, H.D. Sun, Nat. Prod. Bioprospect. 2, 249-254 (2013) 25. P. Pracht, F. Bohle, S. Grimme, Phys. Chem. Chem. Phys. 22, 7169-7192 (2020) 26. M.W. Lodewyk, M.R. Siebert, D.J. Tantillo, Chem. Rev. 112, 1839-1862 (2012) 27. P.H. Willoughby, M.J. Jansma, T.R. Hoye, Nat. Protoc. 9, 643-660 (2014) 28. F. Jensen, Theor. Chem. Acc. 126, 371-382 (2010) 29. G. Pescitelli, T. Bruhn, Chirality 28, 466-474 (2016) 30. T. Lu, F. Chen, J. Comput. Chem. 33, 580-592 (2012) 31. 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.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, 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 E.01 (Gaussian Inc, Wallingford, CT, 2010) |
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|