Two new glutarimide derivatives, 2-hydroxy-3-[2-[2-hydroxy-3-methylphenyl-5-hydroxymethyl]-2-oxoethyl] glutarimide (1) and 2-hydroxy-3-[2-[2-hydroxy-3-hydroxymethyl-5-methylphenyl]-2-oxoethyl] glutarimide (2), along with 8 known compounds were isolated from the liquid fermentation broth of endophytic Streptomyces sp. YINM00048 obtained from Agrimonia pilosa. Their structures were elucidated through comprehensive spectroscopic analysis, including nuclear magnetic resonance, high-resolution mass spectrometry, and single-crystal X-ray diffraction, supported by TDDFT-ECD calculations. Furthermore, compound 2 displayed weak cytotoxic activity against A549 and SMMC-7721 cell lines, with IC50 values of 62.69 and 55.07 μM, respectively.
Su Yu-Ying
,
Wang Ying-Fang
,
Yi Meng-Zhuo
,
Zhao Li-Xing
,
Li Jia-Xuan
,
Ma Ling
,
Yin Min
. Characterization of Glutarimide Derivatives from Agrimonia pilosa-Associated Endophytic Streptomyces sp. YINM00048[J]. Chinese Journal of Organic Chemistry, 0
: 11
-11
.
DOI: 10.6023/cjoc202506015
[1] Koga Y.; Hoang E. M.; Park Y.; Keszei A. F.A.; Murray, J.; Shao, S.; Liau, B. B. J. Am. Chem. Soc. 2021, 143, 13473.
[2] Blom W. M.; de Bont, H. J.; Meijerman, I.; Mulder, G. J.; Nagelkerke, J. F. Biochem. Pharmacol. 1999, 58, 1891.
[3] Li J.; Cai Z.; Vaites L. P.; Shen N.; Mitchell D. C.; Huttlin E. L.; Paulo J. A.; Harry B. L.; Gygi S. P. Mol. Cell. 2021, 81, 4722.
[4] Gold P. E.; Wrenn S. M. Behav. Brain. Res. 2012, 233, 293.
[5] Sun D. D.; Sun W.; Yu Y. X.; Li Z. Y.; Deng Z. X.; Lin S. J. Nat. Prod. Res., 2014, 28, 1602.
[6] Huang S. X.; Yu Z. G.; Robert F.; Zhao L. X.; Jiang Y.; Duan Y. W.; Pelletier J.; Shen B. J.Antibiot. 2011, 64, 163.
[7] Yin M.; Yan Y. J.; Lohman J. R.; Huang S. X.; Ma M.; Zhao G. R.; Xu L. H.; Xiang W. S.; Shen B. Org.Lett. 2014, 16, 3072.
[8] Zhang Z. T.L.; Sun, H. B.; Ren, Z.; Xie, T. P.; Wang, Y. F.; Guo, Y.; Su, X. Y.; Yin, M.; Zhou, H.; Ding, Z. T. RSC Adv. 2023, 13, 36200.
[9] Zhang Z. T.L.; Ren, Z.; Su, X. Y.; Xie, T. P.; Yu, M. Z.; Guo, Y.; Zhou, H.; Yin, M.; Ding, Z. T. RSC Adv. 2025, 15, 1805.
[10] Fukuda T.; Matsumoto A.; Takahashi Y.; Tomoda H.; Omura S. J.Antibiot. 2005, 58, 252.
[11] Aszalos A.; Hoberecht H.; Cohen A. J. Med. Chem. 1967, 10, 281.
[12] Uyeda M.; Aoki M.; Nakajima K.; Shiromoto C.; Tatsuguchi N.; Yokomizo K.; Kido Y.; Kino Y. J.Antibiot. 1992, 45, 1370.
[13] Hua J. C.; Xie Y. Y.Acta Chim. Sinica. 1980, 38, 275 (in Chinese).
(华家柽, 谢毓元. 化学学报, 1980, 38, 275.)
[14] Guo H. F.; Li Y. H.; Yi H.; Zhang T.; Wang S. Q.; Tao P. Z.; Li Z. R.J. Antibiot. 2009, 62, 639.
[15] Cheenpracha, s.; Borris, R. P.; Tran, T. T.; Jee, J. M.; Seow, H. F.; Cheah, H. Y.; Ho, C. C.; Chang, L. C. J. Braz. Chem. Soc. 2011, 22, 223.
[16] Jagannadh B.; Reddy S.S.; Thangavelu R. J. Mol. Model. 2004, 10, 55.
[17] He J.; Pu C. J.; Wang M.; Li Z. H.; Feng T.; Zhao D. K.; Liu J. K.J. Nat. Prod. 2020, 83, 2743.
[18] Li H. T.;L. Tang, H.; Liu, T.; Yang, R. N.; Yang, Y. B.; Zhou, H.; Ding, Z. T. Bioorg. Chem. 2020, 95, 103503.
[19] Bruhn T.; Schaumlöffel A.; Hemberger Y.SpecDis, version 1.64, University of Wüerzburg, Germany, 2015.
[20] Cory A. H.; Owen T. C.; Barltrop J. A.; Cory J. G.Cancer Commun. 1991, 3, 207.
[21] Reed L. J.; Muench H. Am.J. Epidemiol. 1938, 27, 493.