Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

doi:10.1007/s13659-021-00318-9

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (6): 643-649.DOI: 10.1007/s13659-021-00318-9

• ORIGINAL ARTICLES • Previous Articles Next Articles

Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

Chang-An Geng¹, Zhen-Tao Deng¹, Qian Huang¹, Chun-Lei Xiang², Ji-Jun Chen^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 Key Laboratory for Plant Diversity and Biogeography of East Asia, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
3 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China

Received:2021-08-06 Online:2021-12-10 Published:2021-12-24
Contact: Ji-Jun Chen
Supported by:
This work was supported by the Yunnan Wanren Project (YNWR-QNBJ-2018-061), the Natural Science Foundation of Yunnan Province (2019FI017), and the Reserve Talents of Young and Middle-Aged Academic and Technical Leaders in Yunnan Province.

Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

Chang-An Geng¹, Zhen-Tao Deng¹, Qian Huang¹, Chun-Lei Xiang², Ji-Jun Chen^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 Key Laboratory for Plant Diversity and Biogeography of East Asia, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
3 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China

通讯作者: Ji-Jun Chen
基金资助:
This work was supported by the Yunnan Wanren Project (YNWR-QNBJ-2018-061), the Natural Science Foundation of Yunnan Province (2019FI017), and the Reserve Talents of Young and Middle-Aged Academic and Technical Leaders in Yunnan Province.

Abstract

Abstract: Ten 3,5-dimethylcoumarins (1-6 and 8-11) involving six new ones (1-6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro.

Key words: 3,5-Dimethylcoumarins, 3-Methylcoumarin, Chelonopsis, Enzyme inhibition

摘要： Ten 3,5-dimethylcoumarins (1-6 and 8-11) involving six new ones (1-6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro.

关键词: 3,5-Dimethylcoumarins, 3-Methylcoumarin, Chelonopsis, Enzyme inhibition

Chang-An Geng, Zhen-Tao Deng, Qian Huang, Chun-Lei Xiang, Ji-Jun Chen. Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata[J]. Natural Products and Bioprospecting, 2021, 11(6): 643-649.

References

1. M.I. Hussain, Q.A. Syed, M.N.K. Khattak, B. Hafez, M.J. Rrigosa, A. El-Keblawy, Biologia 74, 863–888 (2019)
2. A.G. Estbvez-Braun, Nat. Prod. Rep. 14, 465–475 (1997)
3. R.D.H. Murray, Nat. Prod. Rep. 12, 477–505 (1995)
4. R.D.H. Murray, Nat. Prod. Rep. 6, 591–624 (1989)
5. S. Ahmed, M. Nur-e-Alam, I. Parveen, S.J. Coles, R.M. Hafizur, A. Hameed, J.B. Orton, M.D. Threadgill, M. Yousaf, A.M. Alqahtani, A.J. Al-Rehaily, Phytochemistry 170, 112213 (2020)
6. R.D. Waigh, B.M. Zerihun, D.J. Maitland, Phytochemistry 30, 333–335 (1991)
7. J.de Pascual, A. San Feliciano, J.M. Miguel del Corral, A.F. Barrero, M. Rubio, L. Muriel, Phytochemistry 20, 2778–2779 (1981)
8. M.H. Al Yousuf, A.K. Bashir, G. Blunden, M.-H. Yang, A.V. Patel, Phytochemistry 51, 95–98 (1999)
9. L. Faiella, F. Dal Piaz, A. Bader, A. Braca, Phytochemistry 106, 164–170 (2014)
10. Z.T. Deng, C.A. Geng, T.H. Yang, C.L. Xiang, J.J. Chen, Fitoterapia 132, 60–67 (2019)
11. Z.T. Deng, J.J. Chen, C.A. Geng, Bioorg. Chem. 95, 103571 (2020)
12. X.F. He, C.A. Geng, X.Y. Huang, Y.B. Ma, X.M. Zhang, J.J. Chen, Nat. Prod. Bioprospect. 9, 223–229 (2019)
13. X.F. He, J.J. Chen, T.Z. Li, J. Hu, X.Y. Huang, X.M. Zhang, Y.Q. Guo, C.A. Geng, Chin. J. Chem. 39, 3051–3063 (2021)
14. X.F. He, J.J. Chen, T.Z. Li, J. Hu, X.M. Zhang, C.A. Geng, Bioorg. Chem. 108, 104683 (2021)
15. X.F. He, H.M. Wang, C.A. Geng, J. Hu, X.M. Zhang, Y.Q. Guo, J.J. Chen, Phytochemistry 177, 112418 (2020)
16. Q. Huang, J.J. Chen, Y. Pan, X.F. He, Y. Wang, X.M. Zhang, C.A. Geng, J. Pharm. Biomed. Anal. 198, 113998 (2021)
17. G.H. Jones, J.B.D. Mackenzie, A. Robertson, W.B. Whalley, J. Chem. Soc. 0, 562–569 (1949)
18. D.X. Yan, C.A. Geng, T.H. Yang, X.Y. Huang, T.Z. Li, Z. Gao, Y.B. Ma, H. Peng, X.M. Zhang, J.J. Chen, Fitoterapia 128, 57–65 (2018)
19. C.C. Zhang, C.A. Geng, X.Y. Huang, X.M. Zhang, J.J. Chen, J. Agric. Food Chem. 67, 6765–6772 (2019)

Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

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