Natural Products and Bioprospecting    2018, Vol. 8 Issue (6) : 413-418     DOI: 10.1007/s13659-018-0181-y
ORIGINAL ARTICLES |
New Dammarane Triterpenoids, Caffruones A-D, from the Cherries of Coffea arabica
Xia Wang1,2, Xing-Rong Peng1, Jing Lu1,2, Gui-Lin Hu1,2, Ming-Hua Qiu1,2
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 University of the Chinese Academy of Sciences, Beijing 100049, People's Republic of China
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Abstract  In present study, four new dammarane-type triterpenoids, namely caffruones A-D (1-4), were isolated from the cherries of Coffea arabica. Their structures were elucidated by extensive spectroscopic analysis including 1D, 2D NMR (HSQC, HMBC, 1H-1H COSY, and ROESY), HRMS and IR spectra. This is the first time that tetracyclic triterpenes have been reported in genus Coffea.
Keywords Coffea arabica      Cherries      Triterpenoids      Structural elucidation     
Fund:This study was supported financially by the National Natural Science Foundation of China, China (No. 31670364), Project of Key New Productions of Yunnan Province, China (No. 2015BB002), the STS Programme of Chinese Academy of Sciences, China (KFJ-SW-STS-143-8), Special Fund Project of Pu'er municipal government, China (2017), as well as Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China, China (P2015-ZZ09).
Corresponding Authors: Ming-Hua Qiu     E-mail: mhchiu@mail.kib.ac.cn
Issue Date: 21 November 2018
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Xia Wang,Xing-Rong Peng,Jing Lu, et al. New Dammarane Triterpenoids, Caffruones A-D, from the Cherries of Coffea arabica[J]. Natural Products and Bioprospecting, 2018, 8(6): 413-418.
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http://npb.kib.ac.cn/EN/10.1007/s13659-018-0181-y     OR     http://npb.kib.ac.cn/EN/Y2018/V8/I6/413
1. International Coffee Organization:Trade statistics tables (2018)
2. X.G. Liu, K. Hao, Z.H. Han, N. Yu, Q.L. Yang, Y.W. Liu, Trans. Chin. Soc. Agric. Machin. 47, 143-150 (2016)
3. M. Varghese, L. Ho, J. Wang, W. Zhao, S. Levine, K. Ono, S. Mannino, G.M. Pasinetti, Trans. Neurosc. 5, 111-116 (2014)
4. Y.F. Chu, Y.M. Chen, P.M. Black, P.H. Brown, B.J. Lyle, R.H. Liu, B.X. Ou, Food Chem. 124, 914-920 (2010)
5. G. Grosso, J. Grodos, F. Galvano, E.L. Giovannucci. Annu. Rev. Nutr. 37, 131-156 (2017)
6. J.L. Shao, X.Y. Liu, D.S. Yang, J.L. Fan, L.J. Du, L. Wang, L.X. Wang, J. Shanxi Agric. Sci. 44, 158-163 (2016)
7. R. Chu, L.S. Wan, X.R. Peng, M.Y. Yu, Z.R. Zhang, L. Zhou, Z.R. Li, M.H. Qiu, Nat. Prod. Bioprospect. 6, 217-223 (2016)
8. I. Wahlberg, C.R. Enzell, J.W. Rome, Phytochemistry 14, 1677 (1975)
9. T. Ranheim, B. Halvorsen, Mol. Nutr. Food Res. 49, 274-284 (2010)
10. A. Nehlig, Pract. Neurol. 16, 89-95 (2015)
11. X.H. Cai, X.D. Luo, J. Zhou, X.J. Hao, Org. Lett. 7, 2877-2879 (2005)
12. H. Zhang, H.H. Xu, Z.J. Song, L.Y. Chen, H.J. Wen, Fitoterapia 83, 1081-1086 (2012)
13. R.B. Boar, K. Damps, J. Chem. Soc. Perkin Trans. 5, 510-512 (1977)
14. Z.L. Hong, J. Xiong, S.B. Wu, J.J. Zhu, J.L. Hong, Y. Zhao, G. Xia, J.F. Hu, Phytochemistry 86, 159-167 (2013)
15. M.L. Kennedy, M. Reyes-Batlle, J. Lorenzo-Morales, J.E. Pinero, I.L. Bazzocchi, I.A. Jimenez, Magn. Reson. Chem. Mrc. 56, 46-54 (2017)
16. M. Ukiya, T. Akihisa, H. Tokuda, K. Koike, J. Takayasu, H. Okuda, Y. Kimura, T. Nikaido, H. Nishino, J. Agric. Food Chem. 51, 2949-2957 (2003)
17. A. Inada, S. Ohtsuki, H. Murata, Y. Inatomi, D. Darnaedi, T. Nakanishi, Phytochemistry 46, 379-381 (1997)
18. H. Chávez, A. Estévez-Braun, R. Ángel, A.G. González, Tetrahedron 53, 6465-6472 (1997)
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