Natural Products and Bioprospecting    2021, Vol. 11 Issue (2) : 235-241     DOI: 10.1007/s13659-021-00297-x
ORIGINAL ARTICLES |
Structures, Chemical Conversions, and Cytotoxicity of Tricholopardins C and D, Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum
Chen Shi1, Yue-Ling Peng2, Juan He1, Zheng-Hui Li1, Ji-Kai Liu1, Tao Feng1
1 School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074, People's Republic of China;
2 The Third People's Hospital of Datong, Datong 037000, People's Republic of China
Download: PDF(5067 KB)   HTML ()  
Export: BibTeX | EndNote | Reference Manager | ProCite | RefWorks    
Abstract  Two undescribed Tricholoma triterpenoids, namely tricholopardins C (1) and D (2), were isolated from the wild mushroom Tricholoma pardinum. Their structures with absolute configurations were elucidated by spectroscopic methods, as well as the single crystal X-ray diffraction. Compounds 1 and 2 were further obtained by chemical conversions from the known analogues. Compound 1 showed significant cytotoxicity to MCF-7 and Hela cell lines with IC50 values of 4.7 μM and 9.7 μM, respectively. Its mechanism of inducing MCF-7 cell apoptosis was studied briefly.
Keywords Tricholoma pardinum      Tricholoma triterpenoids      Chemical conversion      Cytotoxicity     
Fund:This work was financially supported by the National Natural Science Foundation of China (81872762) and the Hubei Provincial Natural Science Foundation of China (2019CFB387). The authors thank the Analytical & Measuring Center, School of Pharmaceutical Sciences, South-Central University for Nationalities for spectra test.
Corresponding Authors: Tao Feng     E-mail: tfeng@mail.scuec.edu.cn
Issue Date: 07 April 2021
Service
E-mail this article
E-mail Alert
RSS
Articles by authors
Chen Shi
Yue-Ling Peng
Juan He
Zheng-Hui Li
Ji-Kai Liu
Tao Feng
Trendmd:   
Cite this article:   
Chen Shi,Yue-Ling Peng,Juan He, et al. Structures, Chemical Conversions, and Cytotoxicity of Tricholopardins C and D, Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum[J]. Natural Products and Bioprospecting, 2021, 11(2): 235-241.
URL:  
http://npb.kib.ac.cn/EN/10.1007/s13659-021-00297-x     OR     http://npb.kib.ac.cn/EN/Y2021/V11/I2/235
1. F. Bray, J. Ferlay, I. Soerjomataram, R.L. Siegel, L.A. Torre, A. Jemal, CA-Cancer J. Clin. 68, 394-424 (2018)
2. S. Salas-Vega, O. Iliopoulos, E. Mossialos, JAMA Oncol. 3, 382-390 (2017)
3. D.J. Newman, G.M. Cragg, J. Nat. Prod. 83, 770-803 (2020)
4. G. F. Bills, J. B. Gloer, 4 (2016). https://doi.org/10.1128/microbiolspec.FUNK-0009-2016.
5. T. Feng, X.Q. Gan, Y.L. Zhao, S.B. Zhang, H.P. Chen, J. He, Y.S. Zheng, H. Sun, R. Huang, Z.H. Li, J.K. Liu, J. Nat. Prod. 82, 45-50 (2019)
6. M. De Bernardi, L. Garlaschelli, G. Gatti, G. Vidari, P. Vita-Finzi, Tetrahedron 44, 235-240 (1988)
7. M. De Bernardi, L. Garlaschelli, L. Toma, G. Vidari, P. Vita-Finzi, Tetrahedron 47, 7109-7116 (1991)
8. D. Gozzini, G.G. Mellerio, G. Gilardoni, M. Clericuzio, G. Vidari, Nat. Prod. Commun. 13, 1097-1100 (2018)
9. S.P.B. Ovenden, J. Yu, J. Bernays, S.S. Wan, L.J. Christophidis, G. Sberna, R.M. Tait, H.G. Wildman, D. Lebeller, D. Platel, T.W. May, B.M. Meurer-Grimes, J. Nat. Prod. 68, 409-412 (2005)
10. X. Yin, T. Feng, J.H. Shang, Y.L. Zhao, F. Wang, Z.H. Li, Z.J. Dong, X.D. Luo, J.K. Liu, Chem. Eur. J. 20, 7001-7009 (2014)
11. T. Feng, J. He, H.L. Ai, R. Huang, Z.H. Li, J.K. Liu, Nat. Prod. Bioprospect. 5, 205-208 (2015)
12. Z.Z. Zhao, H.P. Chen, B. Wu, L. Zhang, Z.H. Li, T. Feng, J.K. Liu, J. Org. Chem. 82, 7974-7979 (2017)
13. S.B. Zhang, Z.H. Li, M. Stadler, H.P. Chen, Y. Huang, X.Q. Gan, T. Feng, J.K. Liu, Phytochemistry 152, 105-112 (2018)
14. F.L. Zhang, H.X. Yang, X. Wu, J.Y. Li, S.Q. Wang, J. He, Z.H. Li, T. Feng, J.K. Liu, Phytochemistry 177, 112431 (2020)
15. G. Ciriello, M.L. Gatza, A.H. Beck, M.D. Wilkerson, S.K. Rhie, A. Pastore, H. Zhang, M. McLellan, C. Yau, C. Kandoth, R. Bowlby, H. Shen, S. Hayat, R. Fieldhouse, S.C. Lester, G.M.K. Tse, R.E. Factor, L.C. Collins, K.H. Allison, Y.-Y. Chen, K. Jensen, N.B. Johnson, S. Oesterreich, G.B. Mills, A.D. Cherniack, G. Robertson, C. Benz, C. Sander, P.W. Laird, K.A. Hoadley, T.A. King, TCGA Research Network, C.M. Perou, Cell 163, 506-519 (2015)
16. E. Panza, M. Tersigni, M. Iorizzi, F. Zollo, S. De Marino, C. Festa, M. Napolitano, G. Castello, A. Ialenti, A. Ianaro, J. Nat. Prod. 74, 228-233 (2011)
17. D. Green, G. Kroemer, Trends Cell Biol. 8, 267-271 (1998)
[1] Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus[J]. Natural Products and Bioprospecting, 2021, 11(1): 73-79.
[2] Mohammad Sanad Abu-Darwish, Célia Cabral, Zulfigar Ali, Mei Wang, Shabana I. Khan, Melissa R. Jacob, Surendra K. Jain, Babu L. Tekwani, Fazila Zulfiqar, Ikhlas A. Khan, Hatem Taifour, Lígia Salgueiro, Thomas Efferth. Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities[J]. Natural Products and Bioprospecting, 2020, 10(5): 307-316.
[3] Cheng Shen, Xiao-Yan Huang, Chang-An Geng, Tian-Ze Li, Shuang Tang, Li-Hua Su, Zhen Gao, Xue-Mei Zhang, Jing Hu, Ji-Jun Chen. Artemlavanins A and B from Artemisia lavandulaefolia and Their Cytotoxicity Against Hepatic Stellate Cell Line LX2[J]. Natural Products and Bioprospecting, 2020, 10(4): 243-250.
[4] Shuang Tang, Yun-Bao Ma, Chang-An Geng, Cheng Shen, Tian-Ze Li, Xue-Mei Zhang, Li-Hua Su, Zhen Gao, Jing Hu, Ji-Jun Chen. Artemyrianins A-G from Artemisia myriantha and Their Cytotoxicity Against HepG2 Cells[J]. Natural Products and Bioprospecting, 2020, 10(4): 251-260.
[5] Jia-Huan Shang, Guo-Wei Xu, Hong-Tao Zhu, Dong Wang, Chong-Ren Yang, Ying-Jun Zhang. Anti-inflammatory and Cytotoxic Triterpenes from the Rot Roots of Panax notoginseng[J]. Natural Products and Bioprospecting, 2019, 9(4): 287-295.
[6] Cheng-Ji Li, Fan Xia, Rong Wu, Hong-Sheng Tan, Hong-Xi Xu, Gang Xu, Hong-Bo Qin. Synthesis and Cytotoxicities of Royleanone Derivatives[J]. Natural Products and Bioprospecting, 2018, 8(6): 453-456.
[7] Yang Tang, Zhen-Zhu Zhao, Zheng-Hui Li, Tao Feng, He-Ping Chen, Ji-Kai Liu. Irpexoates A-D, Four Triterpenoids with Malonyl Modifications from the Fruiting Bodies of the Medicinal Fungus Irpex lacteus[J]. Natural Products and Bioprospecting, 2018, 8(3): 171-176.
[8] Rong Chen, Jian-Wei Tang, Xing-Ren Li, Miao Liu, Wen-Ping Ding, Yuan-Fei Zhou, Wei-Guang Wang, Xue Du, Han-Dong Sun, Pema-Tenzin Puno. Secondary Metabolites from the Endophytic Fungus Xylaria sp. Hg1009[J]. Natural Products and Bioprospecting, 2018, 8(2): 121-129.
[9] Manar Adam, Gihan O. M. Elhassan, Sakina Yagi, Fatma Sezer Senol, Ilkay Erdogan Orhan, Abdel Azim Ahmed, Thomas Efferth. In Vitro Antioxidant and Cytotoxic Activities of 18 Plants from the Erkowit Region, Eastern Sudan[J]. Natural Products and Bioprospecting, 2018, 8(2): 97-105.
[10] Zhen-Xiong Wang, Shen Qin, Li-Hua Xu, He-Ping Chen, Huan Sun, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Xylanilyticolides A-C, Three New Compounds from Cultures of the Actinomycete Promicromonospora xylanilytica YIM 61515[J]. Natural Products and Bioprospecting, 2018, 8(2): 91-95.
[11] Xing Yu, Kai-Ting Duan, Zhen-Xiong Wang, He-Ping Chen, Xiao-Qing Gan, Rong Huang, Zheng-Hui Li, Tao Feng, Ji-Kai Liu. Anemhupehins A-C, Podocarpane Diterpenoids from Anemone hupehensis[J]. Natural Products and Bioprospecting, 2018, 8(1): 31-35.
[12] Xin Wei, Afsar Khan, Da Song, Zhi Dai, Ya-Ping Liu, Hao-Fei Yu, Bei Wang, Pei-Feng Zhu, Cai-Feng Ding, Xu-Dong Zhao, Yi-Fen Wang, Xiao-Dong Luo. Three New Pyridine Alkaloids from Vinca major Cultivated in Pakistan[J]. Natural Products and Bioprospecting, 2017, 7(4): 323-327.
[13] Xu-Jie Qin, Tong Shu, Qian Yu, Huan Yan, Wei Ni, Lin-Kun An, Pan-Pan Li, Yin-E Zhi, Afsar Khan, Hai-Yang Liu. Cytotoxic Acylphloroglucinol Derivatives from Callistemon salignus[J]. Natural Products and Bioprospecting, 2017, 7(4): 315-321.
[14] Miao Liu, Zheng-Xi Hu, Yuan-Qing Luo, Min Zhou, Wei-Guang Wang, Xiao-Nian Li, Xue Du, Jian-Xin Pu, Han-Dong Sun. Two New Compounds from Schisandra propinqua var. propinqua[J]. Natural Products and Bioprospecting, 2017, 7(3): 257-262.
[15] Li-Xia Wang, Hai-Rong Zheng, Fu-Cai Ren, Tian-Ge Chen, Xiang-Mei Li, Xian-Jun Jiang, Fei Wang. Polysubstituted Isoflavonoids from Spatholobus suberectus, Flemingia macrophylla, and Cudrania cochinchinensis[J]. Natural Products and Bioprospecting, 2017, 7(2): 201-206.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed