Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete <i>Hypoxylon rickii</i>(Xylariaceae)

doi:10.1007/s13659-015-0065-3

Natural Products and Bioprospecting

2015, Vol. 5

Issue (3) : 167-173 DOI: 10.1007/s13659-015-0065-3

Original article

Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)

Frank Surup, Eric Kuhnert, Elena Liscinskij, Marc Stadler

Department Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstraße 7, 38124 Braunschweig, Germany

Abstract
References
Related Articles
Metrics

Download: PDF(582 KB) HTML ()
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks

Abstract A culture isolated from ascospores of Hypoxylon rickii, a xylariaceous ascomycete collected in Martinique, had yielded botryane, noreremophilane and abietane-type terpenoids in a preceding study, but additional metabolites were detected by extensive HPLC-MS analysis in other fractions. Herein we report the further isolation of four new sesquiterpenoids with a silphiperfol-6-ene skeleton from extracts of H. rickii. The planar structures were elucidated by NMR and HRMS data as 13-hydroxysilphiperfol-6-ene(1), 9-hydroxysilphiperfol-6-en-13-oic acid(2), 2-hydroxysilphiperfol-6-en-13-oic acid(3) and 15-hydroxysilphiperfol-6-en-13-oic acid(4). For compounds 2-4 we propose the trivial names rickinic acids A-C. Their stereochemistry was assigned by ROESY correlations as well as by the specific optical rotation. Additionally, the known compounds, botryenanol, dehydrobotrydienol, cyclo(Phe-Pro), cyclo(Pro-Leu),(+)-ramulosin and aeleostearic acid were isolated. The antimicrobial and cytotoxic activities of the new compounds are also reported.

Keywords Hypoxylon Xylariaceae Natural products Secondary metabolites Structure elucidation

Issue Date: 11 February 2018

	Service

	E-mail this article
	E-mail Alert
	RSS
	Articles by authors

	Frank Surup
	Eric Kuhnert
	Elena Liscinskij
	Marc Stadler

Trendmd:

Cite this article:

Frank Surup,Eric Kuhnert,Elena Liscinskij, et al. Silphiperfolene-Type Terpenoids and Other Metabolites from Cultures of the Tropical Ascomycete Hypoxylon rickii(Xylariaceae)[J]. Natural Products and Bioprospecting, 2015, 5(3): 167-173.

URL:

http://npb.kib.ac.cn/EN/10.1007/s13659-015-0065-3 OR http://npb.kib.ac.cn/EN/Y2015/V5/I3/167

1. M. Stadler, D.N. Quang, A. Tomita, T. Hashimoto, Y. Asakawa, Mycol. Res. 110, 811-820 (2006)
2. F. Surup, K.I. Mohr, R. Jansen, M. Stadler, Phytochemistry 95, 252-258 (2013)
3. X.N. Wang, W.Y. Huang, J.C. Ju, C.Y. Li, J.K. Liu, Biochem. Syst. Ecol. 54, 157-159 (2014)
4. E. Kuhnert, S. Heitkamper, J. Fournier, F. Surup, M. Stadler, Fungal Biol. 118, 242-252 (2014)
5. E. Kuhnert, F. Surup, E.B. Sir, C. Lambert, K.D. Hyde, A.I. Hladki, A.I. Romero, M. Stadler, Fungal Divers. 71, 165-184 (2015)
6. E.B. Sir, E. Kuhnert, F. Surup, K.D. Hyde, M. Stadler, Mycol. Prog. 14, 28 (2015)
7. M. Stadler, V. Hellwig, Recent Res. Dev. Phytochem. 9, 41-93 (2005)
8. F. Surup, E. Kuhnert, E. Lehmann, S. Heitkamper, K.D. Hyde, J. Fournier, M. Stadler, Mycology 5, 110-119 (2014)
9. M. Daferner, S. Mensch, T. Anke, O. Sterner, Z. Naturforsch, C 54, 474-480 (1999)
10. C.J. Smith, N.R. Morin, G.F. Bills, A.W. Dombrowski, G.M. Salituro, S.K. Smith, A. Zhao, D.J. MacNeil, J. Org. Chem. 67, 5001-5004 (2002)
11. J. Pinon, P.D. Manion, Eur. J. For. Pathol. 21, 202-209 (1991)
12. T. Ando, K. Yoshida, M. Okuhara, J. Antibiot. 41, 31-35 (1988)
13. D.R. Jayanetti, Q. Yue, G.F. Bills, J.B. Gloer, J. Nat. Prod. 78, 396-401 (2015)
14. X.D. Qin, H.J. Shao, Z.J. Dong, J.K. Liu, J. Antibiot. 61, 556-562 (2008)
15. E. Kuhnert, F. Surup, V. Wiebach, S. Bernecker, M. Stadler, Phytochemistry 117, 116-122 (2015)
16. L.A. Paquette, R.A. Roberts, G.J. Drtina, J. Am. Chem. Soc. 106, 6690-6693 (1984)
17. I.G. Collado, R. Hernandez-Galan, V. Prieto, J.R. Hanson, L.G. Rebordinos, Phytochemistry 41, 513-517 (1996)
18. R. Duran-Patrón, R. Hernandez-Galan, I. Collado, J. Nat. Prod. 63, 182-184 (2000)
19. M. Tullberg, M. Grotli, K. Luthman, Tetrahedron 62, 7484-7491 (2006)
20. M. Soledade, C. Pedras, Y. Yu, J. Liu, Y.A. Tandron-Moya, Z. Naturforsch. C 60, 717-722 (2005)
21. D.B. Stierle, A.A. Stierle, A. Kunz, J. Nat. Prod. 61, 1277-1278 (1998)
22. Y. Amakura, K. Kondo, H. Akiyama, H. Ito, T. Hatano, T. Yoshida, T. Maitani, J. Food Hyg. Soc. Jpn. 47, 178-181 (2006)
23. F. Bohlmann, J. Jakupovic, Phytochemistry 19, 259-265 (1980)
24. P. Weyerstahl, H. Marschall, I. Seelmann, J. Jakupovic, Eur. J. Org. Chem. 6, 1205-1212 (1998)
25. B. Tudzynski, Appl. Microbiol. Biotechnol. 66, 597-611 (2005)
26. R.M. Coates, Z. Ho, M. Klobus, S.R. Wilson, J. Am. Chem. Soc. 118, 9249-9254 (1996)
27. I.G. Collado, A.J.M. Sanchez, J.R. Hanson, Nat. Prod. Rep. 24, 674-686 (2007)
28. K. Krohn, J. Dai, U. Florke, H.J. Aust, S. Drager, B. Schulz, J. Nat. Prod. 68, 400-405 (2005)
29. J.R. Anderson, L.E. Edwards, J. Chem. Soc. Perkin Trans. 1, 2185-2192 (1983)
30. W.F. Hendershot, C.W. Hesseltine, T.G. Pridham, R.G. Benedict, R.W. Jackson, Arch. Biochem. Biophys. 96, 166-170 (1962)
31. Y.S. Chen, Bull. Chem. Soc. Jpn 24, 372-381 (1960)
32. S. Halecker, F. Surup, E. Kuhnert, K.I. Mohr, N.L. Brock, J.S. Dickschat, C. Junker, B. Schulz, M. Stadler, Phytochemistry 100, 86-91 (2014)
33. E. Kuhnert, J. Fournier, D. Peršoh, J.J. Luangsa-ard, M. Stadler, Fungal Divers. 64, 181-203 (2014)
34. M. Stadler, T. Læssoe, J. Fournier, C. Decock, B. Schmieschek, H.V. Tichy, D. Peršoh, Stud. Mycol. 77, 1-143 (2014)
35. F. Surup, B. Thongbai, E. Kuhnert, E. Sudarman, K.D. Hyde, M. Stadler, J. Nat. Prod. 78, 934-938 (2015)

[1]	Ai-Jun Ding, Shan-Qing Zheng, Xiao-Bing Huang, Ti-Kun Xing, Gui-Sheng Wu, Hua-Ying Sun, Shu-Hua Qi, Huai-Rong Luo. Current Perspective in the Discovery of Anti-aging Agents from Natural Products[J]. Natural Products and Bioprospecting, 2017, 7(5): 335-404.
[2]	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]. Natural Products and Bioprospecting, 2016, 6(2): 63-96.
[3]	Wen-Ting Chen, Lin-Fu Liang, Xu-Wen Li, Wei Xiao, Yue-Wei Guo. Further New Highly Oxidative Cembranoids from the Hainan Soft Coral Sarcophyton trocheliophorum[J]. Natural Products and Bioprospecting, 2016, 6(2): 97-102.
[4]	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.
[5]	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.
[6]	Kun Wei, Gang-Qiang Wang, Xue Bai, Yan-Fen Niu, He-Ping Chen, Chun-Nan Wen, Zheng-Hui Li, Ze-Jun Dong, Zhi-Li Zuo, Wen-Yong Xiong, Ji-Kai Liu. Structure-Based Optimization and Biological Evaluation of Pancreatic Lipase Inhibitors as Novel Potential Antiobesity Agents[J]. Natural Products and Bioprospecting, 2015, 5(3): 129-157.
[7]	Joel Heisler, Lindsay Elvir, Farah Barnouti, Erica Charles, Tom D. Wolkow, Radha Pyati. *Morphological Effects of Natural Products on Schizosaccharomyces pombe* Measured by Imaging Flow Cytometry**[J]. Natural Products and Bioprospecting, 2014, 4(1): 27-35.
[8]	Ponnambalam SUBHASHINI, Elangovan DILIPAN, Thirunavukkarasu THANGARADJOU, Jutta PAPENBROCK. Bioactive natural products from marine angiosperms: abundance and functions[J]. Natural Products and Bioprospecting, 2013, 3(4): 129-136.
[9]	Mohammad Mijanur RAHMAN, Md. Asaduzzaman KHAN. Anti-cancer potential of South Asian plants[J]. Natural Products and Bioprospecting, 2013, 3(3): 74-88.
[10]	Steffen WÖLL, Sun Hee KIM, Henry Johannes GRETEN, Thomas EFFERTH. Animal plant warfare and secondary metabolite evolution[J]. Natural Products and Bioprospecting, 2013, 3(1): 1-7.
[11]	Xu DENG, Ling-Mei KONG, Yu ZHAO, Juan HE, Li-Yan PENG, Yan LI, Qin-Shi ZHAO. Exploring of drug leads from diversity-oriented Michael-acceptor library derived from natural products[J]. Natural Products and Bioprospecting, 2012, 2(5): 210-216.
[12]	Hassan KHALID, Wail Elsadig ABDALLA, Haider ABDELGADIR, Till OPATZ, Thomas EFFERTH. Gems from traditional north-African medicine: medicinal and aromatic plants from Sudan[J]. Natural Products and Bioprospecting, 2012, 2(3): 92-103.

Viewed

Full text

Abstract

Cited

Shared

Discussed