Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

doi:10.1007/s13659-016-0099-1

应用天然产物 ›› 2016, Vol. 6 ›› Issue (4): 217-223.DOI: 10.1007/s13659-016-0099-1

Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

Rui Chu^1,2, Luo-Sheng Wan¹, Xing-Rong Peng¹, Mu-Yuan Yu^1,2, Zhi-Run Zhang¹, Lin Zhou¹, Zhong-Rong Li¹, Ming-Hua Qiu^1,2

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. University of Chinese Academy of Sciences, Beijing 100049, China

收稿日期:2016-03-22 修回日期:2016-04-10 出版日期:2016-08-24 发布日期:2018-02-08
通讯作者: Ming-Hua Qiu,e-mail:mhchiu@mail.kib.ac.cn
基金资助:
This work was supported financially by Programme of Key New Productions of Yunnan Province,Centre of CHINA (No.2015BB002);The STS Programme of Chinese Academy of Sciences (KFJ-SW-STS-143-8);as well as Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China (P2015-ZZ09)

Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

Rui Chu^1,2, Luo-Sheng Wan¹, Xing-Rong Peng¹, Mu-Yuan Yu^1,2, Zhi-Run Zhang¹, Lin Zhou¹, Zhong-Rong Li¹, Ming-Hua Qiu^1,2

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2. University of Chinese Academy of Sciences, Beijing 100049, China

Received:2016-03-22 Revised:2016-04-10 Online:2016-08-24 Published:2018-02-08
Supported by:
This work was supported financially by Programme of Key New Productions of Yunnan Province,Centre of CHINA (No.2015BB002);The STS Programme of Chinese Academy of Sciences (KFJ-SW-STS-143-8);as well as Foundation of State Key Laboratory of Phytochemistry and Plant Resources in West China (P2015-ZZ09)

摘要/Abstract

摘要： Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

关键词: Coffea arabica L., Green coffee beans, Diterpenoids, Structural elucidation

Abstract: Five new ent-kaurane diterpenoids, named mascaroside III-V (1-3), and 20-nor-cofaryloside I-II (4-5), together with seven known diterpenoids, were isolated from methanol extracts of the green coffee beans of Yunnan Arabica Coffee. Their chemical structures were elucidated by extensive spectroscopic analyses. Meanwhile, cytotoxicity assay against HL-60, A-549, SMMC-7721, MCF-7 and SW480 cell lines showed that they have not evident inhibition of cytotoxicity.

Key words: Coffea arabica L., Green coffee beans, Diterpenoids, Structural elucidation

Rui Chu, Luo-Sheng Wan, Xing-Rong Peng, Mu-Yuan Yu, Zhi-Run Zhang, Lin Zhou, Zhong-Rong Li, Ming-Hua Qiu. Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans[J]. 应用天然产物, 2016, 6(4): 217-223.

参考文献

1. F.F. Wei, K. Furihata, M. Koda, F.Y. Hu, T. Miyakawa, M. Tanokura, J. Agric. Food Chem. 60, 1005-1012 (2012)
2. L.R. Cagliani, G. Pellegrino, G. Giugno, R. Consonni, Talanta 106, 169-173 (2013)
3. M.M. Naidu, G. Sulochanamma, S.R. Sampathu, P. Srinivas, Food Chem. 107, 377-384 (2008)
4. W.J. Hughes, T.M. Thorpe, J. Food Sci. 52, 1078-1083 (1987)
5. I.D. Fisk, A. Kettle, S. Hofmeister, A. Virdie, J.S. Kenny, Flavor 1, 1-9 (2012)
6. X. Li, W.L. Xiao, J.X. Pu, L.L. Ban, Y.H. Shen, Z.Y. Weng, S.H. Li, H.D. Sun, Phytochemistry 67, 1336-1340 (2006)
7. K.J. Lee, J.H. Choi, H.G. Jeong, Food Chem. Toxicol. 45, 2118-2125 (2007)
8. C. Cardenas, A.R. Quesada, M.A. Medina, PLoS One 6, 1-9 (2011)
9. T. Kurzrock, K. Speer, Food Rev. Int. 17, 433-450 (2001)
10. Y. Shu, J.Q. Liu, X.R. Peng, L.S. Wan, L. Zhou, T. Zhang, M.H. Qiu, J. Agric. Food Chem. 62, 2631-2637 (2014)
11. P. Roland, G. Armin, Phytochemistry 29, 990-992 (1990)
12. J.Q. Zhao, Y.M. Wang, J.J. Lv, H.T. Zhu, D. Wang, C.R. Yang, M. Xu, Y.J. Zhang, J. Braz. Chem. Soc. 25, 1446-1454 (2014)
13. B.W. Russell, R.E. Gary, M.S. Courtney, J. Nat. Prod. 76, 1592-1597 (2013)
14. K. Nishimura, Y. Hitotsuyanagi, K. Sakakura, K. Fujita, S. Tachihara, H. Fukaya, Y. Aoyagi, T. Hasuda, T. Kinoshita, K. Takeya, Tetrahedron 63, 4558-4562 (2007)
15. R. Wang, W.H. Chen, Y.P. Shi, J. Nat. Prod. 73, 17-21 (2010)
16. A. Braca, A.I. Armenise, J. Mendez, Q. Mi, H.B. Chai, Plant Med. 70, 540-550 (2004)
17. X.F. Cai, L.I. Seon, D.N. Tien, G. Shen, K.Y. Ho, Phytother. Res. 18, 677-680 (2004)
18. M.H. Choudhury, H. Quamrul, Nat. Prod. Lett. 5, 55-60 (1994)
19. O. Emika, K. Satoshi, Phytochemistry 65, 885-890 (2004)
20. J. Liu, L. Feng, H.D. Li, Q.L. Dong, R. Chen, Helv. Chim. Acta 95, 221-226 (2012)
21. T. Mosmann, J. Immunol. Methods 65, 55-63 (1983)

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Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

Characterization of New Ent-kaurane Diterpenoids of Yunnan Arabica Coffee Beans

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