A chemical study on the n-BuOH-soluble fraction of the 95% EtOH extract of rice fermented with the endophytic fungus Annulohypoxylon nitens has resulted in the isolation of one new natural pyrrole derivative, designated as nitenspyrrole (1), together with 3 known compounds, taraxasterol (2), oleanolic acid (3), and β-sitostenone (4). Their structures were elucidated by spectroscopic analyses including 1D and 2D NMR experiments, and by ESI-MS.
Similar content being viewed by others
References
G. A. Strobel, Crit. Rev. Biotechnol., 22, 315 (2002).
G. A. Strobel and D. M. Long, ASM News, 64, 263 (1998).
G. Strobel, B. Daisy, U. Castillo, and J. Harper, J. Nat. Prod., 67, 257 (2004).
R. X. Tan and W. X. Zou, Nat. Prod. Rep., 18, 448 (2001).
L. P. Bush, H. H. Wilkinson, and C. L. Schardl, Plant Physiol., 114, 1 (1997).
F. B. Sean, M. B. Shana, and C. Jon, J. Am. Chem. Soc., 123, 9900 (2001).
R. X. Tan and W. X. Zou, Nat. Prod. Rep., 18, 448 (2001).
C. Lu and Y. Shen, J. Antibiot., 56, 415 (2003).
H. M. Hsieh and Y. M. Ju, Mycol., 97, 844 (2005).
A. J. S. Whalley and R. L. Edwards, Can. J. Bot., 73, 802 (1995).
S. J. Coval, M. S. Puar, D.W. Phife, J. S. Terracciano, and M. Patel, J. Antibiot., 48, 1171 (1995).
Y. Lin, X. Wu, S. Feng, G. Jiang, S. Zhou, L. L. P. Vrijmoed, and E. B. G. Jones, Tetrahedron Lett., 42, 449 (2001).
H. Huang, Z. She, Y. Lin, L. L. P. Vrijmoed, and W. Lin, J. Nat. Prod., 70, 1696 (2007).
S. Boonphong, P. Kittakoop, M. Isaka, D. Pittayakhajonwut, M. Tanticharoen, and Y. Thebtaranonth, J. Nat. Prod., 64, 965 (2001).
D. O. Hagana, S. V. Rogers, G. R. Duffin, and R. L. Edwards, Tetrahedron Lett., 33, 5585 (1992).
H. Jayasuriya, K. B. Herath, J. G. Ondeyka, J. D. Polishook, G. F. Bills, A. W. Dombrowski, M. S. Springer, S. Siciliano, L. Malkowitz, M. Sanchez, Z. Guan, S. Tiwari, D. W. Stevenson, R. P. Borris, and S. B. Singh, J. Nat. Prod., 67, 1036 (2004).
R. A. Davis and G. K. Pierens, Magn. Reson. Chem., 44, 966 (2006).
P. C. Healy, A. Hocking, N. Tran-Dinh, J. I. Pitt, R. G. Shivas, J. K. Mitchell, M. Kotiw, and R. A. Davis, Phytochemistry, 65, 2373 (2004).
Y. Lin, X. Wu, S. Feng, G. Jiang, J. Luo, S. Zhou, L. L. P. Vrijmoed, E. B. G. Jones, K. Krohn, K. Steingrcver, and F. Zsila, J. Org. Chem., 66, 6252 (2001).
D. N. Quang, M. Stadler, J. Fournier, A. Tomita, and T. Hashimoto, Tetrahedron, 62, 6349 (2006).
A. Gomez-Sanchez, I. Hermosin, and I. Maya, Carbohydr. Res., 229, 307 (1992).
L. M. Khalilov, A. Z. Khalilova, E. R. Shakurova, I. F. Nuriev, V. V. Kachala, A. S. Shashkov, and U. M. Dzhemilev, Chem. Nat. Compd., 39, 285 (2003).
Y. H. Kuo, S. M. Lee, and J. S. Lai, J. Chin. Chem. Soc., 47, 241 (2000).
Y. H. Kuo and Y. C. Li, J. Chin. Chem. Soc., 44, 321 (1997).
Acknowledgment
This work was kindly supported by the Ministry of Science and Technology, R.O.C. (MOST-108-2320-B-080-002-, MOST-109-2622-E-080-001-, and MOST-110-2320-B-080-001-). The authors thank Senior Technician Mrs. Chyi Jia Wang of the Center for Resources, Research, and Development (CRRD) of Kaohsiung Medical University for measuring the 2D NMR data.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 973–974.
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Wu, MD., Chen, JJ. & Cheng, MJ. Constituents from the Endophytic Fungus of Annulohypoxylon nitens. Chem Nat Compd 59, 1154–1156 (2023). https://doi.org/10.1007/s10600-023-04215-0
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-023-04215-0