Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66

doi:10.1007/s13659-020-00248-y

应用天然产物 ›› 2020, Vol. 10 ›› Issue (4): 201-207.DOI: 10.1007/s13659-020-00248-y

• ORIGINAL ARTICLES • 上一篇下一篇

Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66

Xiao-Zheng Su^1,2,3, Jian-Wei Tang^1,2, Kun Hu^1,2, Xiao-Nian Li^1,2, Han-Dong Sun^1,2, Pema-Tenzin Puno^1,2

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

收稿日期:2020-04-20 修回日期:2020-05-31 出版日期:2020-08-24 发布日期:2020-08-19
通讯作者: Pema-Tenzin Puno
基金资助:
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).

Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66

Xiao-Zheng Su^1,2,3, Jian-Wei Tang^1,2, Kun Hu^1,2, Xiao-Nian Li^1,2, Han-Dong Sun^1,2, Pema-Tenzin Puno^1,2

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

Received:2020-04-20 Revised:2020-05-31 Online:2020-08-24 Published:2020-08-19
Contact: Pema-Tenzin Puno
Supported by:
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).

摘要/Abstract

摘要： 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.

关键词: Isodon xerophilus, Endophytic fungus, Arthrinium, Botryane sesquiterpenoid, Quantum chemical calculation

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.

Key words: Isodon xerophilus, Endophytic fungus, Arthrinium, Botryane sesquiterpenoid, Quantum chemical calculation

Xiao-Zheng Su, Jian-Wei Tang, Kun Hu, Xiao-Nian Li, Han-Dong Sun, Pema-Tenzin Puno. Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66[J]. 应用天然产物, 2020, 10(4): 201-207.

参考文献

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)

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Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66

Arthrinins E-G, Three Botryane Sesquiterpenoids from the Plant Endophytic Fungus Arthrinium sp. HS66

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