Isochromophilones from an endophytic fungus Diaporthe sp

Le-Yun Zang; Wei Wei; Ting Wang; Ye Guo; Ren-Xiang Tan; Hui-Ming Ge

doi:10.1007/s13659-012-0023-2

. 2012 Apr 13;2(3):117–120. doi: 10.1007/s13659-012-0023-2

Isochromophilones from an endophytic fungus Diaporthe sp.

Le-Yun Zang ¹, Wei Wei ¹, Ting Wang ¹, Ye Guo ¹, Ren-Xiang Tan ^1,^✉, Hui-Ming Ge ^1,^✉

PMCID: PMC4131592

Abstract

Three new azaphilone compounds, isochromophilones X–XII (1–3), together with two known ones sclerotioramine (4) and isochromophilone VI (5) were isolated from the cultures of an endophytic fungus Diaporthe sp. The structures were elucidated by extensive HRESIMS and NMR spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines by MTT method, among which compound 1 showed moderate inhibitory effects on these cell lines. This was the first report of azaphilones isolated from Diaporthe sp. graphic file with name 13659_2012_23_Article_Fig1_HTML.jpg

Electronic Supplementary Material

Supplementary material is available for this article at 10.1007/s13659-012-0023-2 and is accessible for authorized users.

Keywords: azaphilone, endophyte, Diaporthe sp., cytotoxicity

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13659_2012_23_MOESM1_ESM.pdf^{(819.6KB, pdf)}

Supplementary material, approximately 819 KB.

Footnotes

This article is published with open access at Springerlink.com

Contributor Information

Ren-Xiang Tan, Email: rxtan@nju.edu.cn.

Hui-Ming Ge, Email: hmge@nju.edu.cn.

References

[1].Udagawa S. I. Chem. Pharm. Bull. 1963;11:366–367. doi: 10.1248/cpb.11.366. [DOI] [Google Scholar]
[2].Arai N., Shiomi K., Tomoda H., Tabata N., Yang D. J., Masuma R., Kawakubo T., Omura S. J. Antibiot. 1995;48:696–702. doi: 10.7164/antibiotics.48.696. [DOI] [PubMed] [Google Scholar]
[3].Osmanova N., Schultze W., Ayoub N. Phytochem. Rev. 2010;9:315–342. doi: 10.1007/s11101-010-9171-3. [DOI] [Google Scholar]
[4].Ge H. M., Zhang W. Y., Ding G., Saparpakorn P., Song Y. C., Hannongbua S., Tan R. X. Chem. Commun. 2008;45:5978–5980. doi: 10.1039/b812144c. [DOI] [PubMed] [Google Scholar]
[5].Laakso J. A., Raulli R., McElhaney-Feser G. E., Actor P., Underiner T. L., Hotovec B. J., Mocek U., Cihlar R. L., Broedel S. E.., Jr J. Nat. Prod. 2003;66:1041–1046. doi: 10.1021/np030046g. [DOI] [PubMed] [Google Scholar]
[6].Anke H., Kemmer T., Höfle G. J. Antibiot. 1981;34:923–928. doi: 10.7164/antibiotics.34.923. [DOI] [PubMed] [Google Scholar]
[7].Quang D. N., Hashimoto T., Tanaka M., Stadler M., Asakawa Y. Phytochemistry. 2004;65:469–473. doi: 10.1016/j.phytochem.2003.09.022. [DOI] [PubMed] [Google Scholar]
[8].Yasukawa K., Itabashi T., Kawai K. I., Takido M. J. Nat. Med. 2008;62:384–386. doi: 10.1007/s11418-008-0250-3. [DOI] [PubMed] [Google Scholar]
[9].Zhang Y. L., Zhang J., Jiang N., Lu Y. H., Wang L., Xu S. H., Wang W., Zhang G. F., Xu Q., Ge H. M., Ma J., Song Y. C., Tan R. X. J. Am. Chem. Soc. 2011;133:5931–5940. doi: 10.1021/ja110932p. [DOI] [PubMed] [Google Scholar]
[10].Guo Z. K., Yan T., Guo Y., Song Y. C., Jiao R. H., Tan R. X., Ge H. M. J. Nat. Prod. 2012;75:15–21. doi: 10.1021/np200321s. [DOI] [PubMed] [Google Scholar]
[11].Wang X., Sena Filho J. G., Hoover A. R., King J. B., Ellis T. K., Powell D. R., Cichewicz R. H. J. Nat. Prod. 2010;73:942–948. doi: 10.1021/np100142h. [DOI] [PMC free article] [PubMed] [Google Scholar]
[12].Michael A. P., Grace E. J., Kotiw M., Barrow R. A. Aust. J. Chem. 2003;56:13–15. doi: 10.1071/CH02021. [DOI] [Google Scholar]
[13].Lee S. Y., Clark R. C., Boger D. L. J. Am. Chem. Soc. 2007;129:9860–9861. doi: 10.1021/ja073264v. [DOI] [PMC free article] [PubMed] [Google Scholar]
[14].Clark R. C., Lee S. Y., Boger D. L. J. Am. Chem. Soc. 2008;130:12355–12369. doi: 10.1021/ja8012819. [DOI] [PMC free article] [PubMed] [Google Scholar]
[15].Matsuzaki K., Tanaka H., Ōmura S. J. Antibiot. 1995;48:708–713. doi: 10.7164/antibiotics.48.708. [DOI] [PubMed] [Google Scholar]
[16].Kanokmedhakul S., Kanokmedhakul K., Nasomjai P., Louangsysouphanh S., Soytong K., Isobe M., Kongsaeree P., Prabpai S., Suksamrarn A. J. Nat. Prod. 2006;69:891–895. doi: 10.1021/np060051v. [DOI] [PubMed] [Google Scholar]
[17].Hajjaj H., Klaebe A., Loret M. O., Goma G., Blanc P. J., Francois J. Appl. Environ. Microbiol. 1999;65:311–314. doi: 10.1128/aem.65.1.311-314.1999. [DOI] [PMC free article] [PubMed] [Google Scholar]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

13659_2012_23_MOESM1_ESM.pdf^{(819.6KB, pdf)}

Supplementary material, approximately 819 KB.

[CR1] [1].Udagawa S. I. Chem. Pharm. Bull. 1963;11:366–367. doi: 10.1248/cpb.11.366. [DOI] [Google Scholar]

[CR2] [2].Arai N., Shiomi K., Tomoda H., Tabata N., Yang D. J., Masuma R., Kawakubo T., Omura S. J. Antibiot. 1995;48:696–702. doi: 10.7164/antibiotics.48.696. [DOI] [PubMed] [Google Scholar]

[CR3] [3].Osmanova N., Schultze W., Ayoub N. Phytochem. Rev. 2010;9:315–342. doi: 10.1007/s11101-010-9171-3. [DOI] [Google Scholar]

[CR4] [4].Ge H. M., Zhang W. Y., Ding G., Saparpakorn P., Song Y. C., Hannongbua S., Tan R. X. Chem. Commun. 2008;45:5978–5980. doi: 10.1039/b812144c. [DOI] [PubMed] [Google Scholar]

[CR5] [5].Laakso J. A., Raulli R., McElhaney-Feser G. E., Actor P., Underiner T. L., Hotovec B. J., Mocek U., Cihlar R. L., Broedel S. E.., Jr J. Nat. Prod. 2003;66:1041–1046. doi: 10.1021/np030046g. [DOI] [PubMed] [Google Scholar]

[CR6] [6].Anke H., Kemmer T., Höfle G. J. Antibiot. 1981;34:923–928. doi: 10.7164/antibiotics.34.923. [DOI] [PubMed] [Google Scholar]

[CR7] [7].Quang D. N., Hashimoto T., Tanaka M., Stadler M., Asakawa Y. Phytochemistry. 2004;65:469–473. doi: 10.1016/j.phytochem.2003.09.022. [DOI] [PubMed] [Google Scholar]

[CR8] [8].Yasukawa K., Itabashi T., Kawai K. I., Takido M. J. Nat. Med. 2008;62:384–386. doi: 10.1007/s11418-008-0250-3. [DOI] [PubMed] [Google Scholar]

[CR9] [9].Zhang Y. L., Zhang J., Jiang N., Lu Y. H., Wang L., Xu S. H., Wang W., Zhang G. F., Xu Q., Ge H. M., Ma J., Song Y. C., Tan R. X. J. Am. Chem. Soc. 2011;133:5931–5940. doi: 10.1021/ja110932p. [DOI] [PubMed] [Google Scholar]

[CR10] [10].Guo Z. K., Yan T., Guo Y., Song Y. C., Jiao R. H., Tan R. X., Ge H. M. J. Nat. Prod. 2012;75:15–21. doi: 10.1021/np200321s. [DOI] [PubMed] [Google Scholar]

[CR11] [11].Wang X., Sena Filho J. G., Hoover A. R., King J. B., Ellis T. K., Powell D. R., Cichewicz R. H. J. Nat. Prod. 2010;73:942–948. doi: 10.1021/np100142h. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR12] [12].Michael A. P., Grace E. J., Kotiw M., Barrow R. A. Aust. J. Chem. 2003;56:13–15. doi: 10.1071/CH02021. [DOI] [Google Scholar]

[CR13] [13].Lee S. Y., Clark R. C., Boger D. L. J. Am. Chem. Soc. 2007;129:9860–9861. doi: 10.1021/ja073264v. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR14] [14].Clark R. C., Lee S. Y., Boger D. L. J. Am. Chem. Soc. 2008;130:12355–12369. doi: 10.1021/ja8012819. [DOI] [PMC free article] [PubMed] [Google Scholar]

[CR15] [15].Matsuzaki K., Tanaka H., Ōmura S. J. Antibiot. 1995;48:708–713. doi: 10.7164/antibiotics.48.708. [DOI] [PubMed] [Google Scholar]

[CR16] [16].Kanokmedhakul S., Kanokmedhakul K., Nasomjai P., Louangsysouphanh S., Soytong K., Isobe M., Kongsaeree P., Prabpai S., Suksamrarn A. J. Nat. Prod. 2006;69:891–895. doi: 10.1021/np060051v. [DOI] [PubMed] [Google Scholar]

[CR17] [17].Hajjaj H., Klaebe A., Loret M. O., Goma G., Blanc P. J., Francois J. Appl. Environ. Microbiol. 1999;65:311–314. doi: 10.1128/aem.65.1.311-314.1999. [DOI] [PMC free article] [PubMed] [Google Scholar]

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Isochromophilones from an endophytic fungus Diaporthe sp.

Le-Yun Zang

Wei Wei

Ting Wang

Ye Guo

Ren-Xiang Tan

Hui-Ming Ge

Abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

Contributor Information

References

Associated Data

Supplementary Materials

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PERMALINK

Isochromophilones from an endophytic fungus Diaporthe sp.

Le-Yun Zang

Wei Wei

Ting Wang

Ye Guo

Ren-Xiang Tan

Hui-Ming Ge

Abstract

Electronic Supplementary Material

Electronic supplementary material

Footnotes

Contributor Information

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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