Abstract
A chemical investigation on the cultures of Xylaria carpophila led to the isolation of one known cyclopeptide cyclo(Nmethyl-l-Phe-l-Pro-l-Leu-d-Ile-l-Val) (1), five new sesquiterpenes, named as xylcarpins A–E (2–6), and another known compound (7). The structures were determined by extensive NMR and MS spectroscopic analysis. The absolute configuration of 1 was established by use of Marfey’s method and ROESY spectroscopic data. All compounds were tested for their cytotoxicities against five human cancer cell lines. Compound 7 showed week inhibitory activity.
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Keywords: Xylaria carpophila, sesquiterpenes, cyclopeptide, cytotoxicity
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References
- [1].Shiono Y., Motoki S., Koseki T., Murayama T., Tojima M., Kimura K. I. Phytochemistry. 2009;70:935–939. doi: 10.1016/j.phytochem.2009.03.023. [DOI] [PubMed] [Google Scholar]
- [2].Isaka M., Yangchum A., Auncharoen P., Srichomthong K., Srikitikulchai P. J. Nat. Prod. 2011;74:300–302. doi: 10.1021/np100873t. [DOI] [PubMed] [Google Scholar]
- [3].Quang D. N., Bach D. D. Nat. Prod. Res. 2008;22:901–906. doi: 10.1080/14786410701642706. [DOI] [PubMed] [Google Scholar]
- [4].Rukachaisirikul V., Khamthong N., Sukpondma Y., Pakawatchai C., Phongpaichit S., Sakayaroj J., Kirtikara K. Chem. Pharm. Bull. 2009;57:1409–1411. doi: 10.1248/cpb.57.1409. [DOI] [PubMed] [Google Scholar]
- [5].Quang D. N., Bach D. D., Hashimoto T., Asakawa Y. Nat. Prod. Res. 2006;20:317–321. doi: 10.1080/14786410600650354. [DOI] [PubMed] [Google Scholar]
- [6].Deyrup S. T., Gloer J. B., O’Donnell K., Wicklow D. T. J. Nat. Prod. 2007;70:378–382. doi: 10.1021/np060546k. [DOI] [PubMed] [Google Scholar]
- [7].Abate D., Abraham W. R., Meyer H. Phytochemistry. 1997;44:1443–1448. doi: 10.1016/S0031-9422(96)00780-7. [DOI] [Google Scholar]
- [8].McDonald L. A., Barbieri L. R., Bernan V. S., Janso J., Lassota P., Carter G. T. J. Nat. Prod. 2004;67:1565–1567. doi: 10.1021/np049924g. [DOI] [PubMed] [Google Scholar]
- [9].Pongcharoen W., Rukachaisirikul V., Isaka M., Sriklung K. Chem. Pharm. Bull. 2007;55:1647–1648. doi: 10.1248/cpb.55.1647. [DOI] [PubMed] [Google Scholar]
- [10].Boonphong S., Kittakoop P., Isaka M., Pittayakhajonwut D., Tanticharoen M., Thebtaranonth Y. J. Nat. Prod. 2001;64:965–967. doi: 10.1021/np000291p. [DOI] [PubMed] [Google Scholar]
- [11].Pongcharoen W., Rukachaisirikul V., Phongpaichit S., Kuhn T., Pelzing M., Sakayaroj J., Taylor Walter C. Phytochemistry. 2008;69:1900–1902. doi: 10.1016/j.phytochem.2008.04.003. [DOI] [PubMed] [Google Scholar]
- [12].Pittayakhajonwut P., Suvannakad R., Thienhirun S., Prabpai S., Kongsaeree P., Tanticharoen M. Tetrahedron Lett. 2005;46:1341–1344. doi: 10.1016/j.tetlet.2004.12.110. [DOI] [Google Scholar]
- [13].Tansuwan S., Pornpakakul S., Roengsumran S., Petsom A., Muangsin N., Sihanonta P., Chaichit N. J. Nat. Prod. 2007;70:1620–1623. doi: 10.1021/np0701069. [DOI] [PubMed] [Google Scholar]
- [14].Singh S. B., Zink D., Polishook J., Valentino D., Shafiee A., Silverman K., Felock P., Teran A., Vilella D., Hazuda D. J., Lingham R. B. Tetrahedron Lett. 1999;40:8775–8779. doi: 10.1016/S0040-4039(99)01878-X. [DOI] [Google Scholar]
- [15].Shiono Y., Murayama T., Takahashi K., Okada K., Katohda S., Tkeda M. Biosci. Biotechnol. Biochem. 2005;69:287–292. doi: 10.1271/bbb.69.287. [DOI] [PubMed] [Google Scholar]
- [16].Wu W. D., Dai H. Q., Bao L., Ren B., Lu J. C., Luo Y. M., Guo L. D., Zhang L. X., Liu H. W. J. Nat. Prod. 2011;74:1303–1308. doi: 10.1021/np100909y. [DOI] [PubMed] [Google Scholar]
- [17] (a).Sakamaki H., Kitanaka S., Chai W., Hayashida Y., Takagi Y., Horiuchi C. A. J. Nat. Prod. 2001;64:630–631. doi: 10.1021/np0004000. [DOI] [PubMed] [Google Scholar]
- [17] (b).Kawai T., Ooi T., Kusumi T. Chem. Pharm. Bull. 2003;51:291–294. doi: 10.1248/cpb.51.291. [DOI] [PubMed] [Google Scholar]
- [17] (c).Hnawia E., Menut C., Agrebi A., Cabalion P. Biochem. Syst. Ecol. 2009;36:859–866. doi: 10.1016/j.bse.2008.08.007. [DOI] [Google Scholar]
- [18].Marco J. A., Juan F. S. C., Vicente G. L., Natalia B. Phytochemistry. 1997;45:755–763. doi: 10.1016/S0031-9422(97)00029-0. [DOI] [Google Scholar]
- [19].Mosmann T. J. Immunol. Methods. 1983;65:55–63. doi: 10.1016/0022-1759(83)90303-4. [DOI] [PubMed] [Google Scholar]
- [20].Lang G., Blunt W. B., Cummings N. J., Cole A. L. J., Munro M. H. G. J. Nat. Prod. 2005;68:1303–1305. doi: 10.1021/np0501536. [DOI] [PubMed] [Google Scholar]
- [21].Reed L. J., Muench H. Am. J. Hyg. 1938;27:493–497. [Google Scholar]
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