New Amides and Phenylpropanoid Glucosides from the Fruits of <i>Piper retrofractum</i>

doi:10.1007/s13659-019-0208-z

Natural Products and Bioprospecting

2019, Vol. 9

Issue (3) : 231-241 DOI: 10.1007/s13659-019-0208-z

ORIGINAL ARTICLES

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

Rong Tang^1,3, Ya-Qiong Zhang², Dong-Bao Hu⁴, Xue-Fei Yang^1,5, Jun Yang^1,5, Myint Myint San⁶, Thaung Naing Oo⁶, Yi Kong², Yue-Hu Wang^1,5

1 Key Laboratory of Economic Plants and Biotechnology and the Yunnan Key Laboratory for Wild Plant Resources, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2 School of Life Science & Technology, China Pharmaceutical University, Nanjing 210009, People's Republic of China;
3 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;
4 School of Chemical Biology and Environment, Yuxi Normal University, Yuxi 653100, People's Republic of China;
5 Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw 05282, Myanmar;
6 Forest Research Institute, Yezin, Nay Pyi Taw 05282, Myanmar

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Abstract Two new amides (E)-N-cinnamoyl-2-methoxypiperidine (1) and (R)-1-(2-oxopyrrolidin-3-yl)-5,6-dihydropyridin-2(1H)-one (2), four new amide glucosides, retrofractosides A-D (3-6), and two new phenylpropanoid glucosides, retrofractosides E (7) and F (8), together with 24 known compounds (9-32) were isolated from the fruits of Piper retrofractum. The chemical structures of these new compounds were elucidated based on extensive spectroscopic analysis. All of these isolates (1-32) were evaluated for inhibitory activity against mouse platelet aggregation induced by the peptide AYPGKF-NH₂. (E)-N-(Tetrahydro-2H-pyran-2-yl)cinnamamide (9) showed a weak inhibitory efect, with an inhibition ratio of 52.0% at a concentration of 150 μM.

Keywords Piper retrofractum Piperaceae Antiplatelet Amides Phenylpropanoids

Fund:This study was supported by the Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences (2015CASEABRIRG001 and Y4ZK111B01), the open foundation of Key Laboratory of Ethnomedicine (Minzu University of China), Ministry of Education (KLEM-KF2018Z01), and the International Partnership Program of Chinese Academy of Sciences (153631KYSB20160004).

Corresponding Authors: Yi Kong, Yue-Hu Wang E-mail: yikong668@163.com;wangyuehu@mail.kib.ac.cn

Issue Date: 05 June 2019

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	Rong Tang
	Ya-Qiong Zhang
	Dong-Bao Hu
	Xue-Fei Yang
	Jun Yang
	Myint Myint San
	Thaung Naing Oo
	Yi Kong
	Yue-Hu Wang

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Rong Tang,Ya-Qiong Zhang,Dong-Bao Hu, et al. New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum[J]. Natural Products and Bioprospecting, 2019, 9(3): 231-241.

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http://npb.kib.ac.cn/EN/10.1007/s13659-019-0208-z OR http://npb.kib.ac.cn/EN/Y2019/V9/I3/231

1. S. Vinay, K. Renuka, V. Palak, C.R. Harisha, P.K. Prajapati, J. Pharm. Sci. Innovat. 1, 62-66 (2012)
2. M. Kubo, R. Ishii, Y. Ishino, K. Harada, N. Matsui, M. Akagi, E. Kato, S. Hosoda, Y. Fukuyama, J. Nat. Prod. 76, 769-773 (2013)
3. J.W. Ahn, M.J. Ahn, O.P. Zee, E.J. Kim, S.G. Lee, H.J. Kim, I. Kubo, Phytochemistry 31, 3609-3612 (1992)
4. A. Banerji, D. Bandyopadhyay, M. Sarkar, A.K. Siddhanta, S.C. Pal, S. Ghosh, K. Abraham, J.N. Shoolery, Phytochemistry 24, 279-284 (1985)
5. R. Muharini, Z. Liu, W. Lin, P. Proksch, Tetrahedron Lett. 56, 2521-2525 (2015)
6. V.R.S. Rao, G. Suresh, K.S. Babu, S.S. Raju, M.V.P.S.V. Vardhan, S. Ramakrishna, J.M. Rao, Tetrahedron 67, 1885-1892 (2011)
7. H.S. Bodiwala, G. Singh, R. Singh, C.S. Dey, S.S. Sharma, K.K. Bhutani, I.P. Singh, J. Nat. Med. 61, 418-421 (2007)
8. H. Matsuda, K. Ninomiya, T. Morikawa, D. Yasuda, I. Yamaguchi, M. Yoshikawa, Bioorg. Med. Chem. 17, 7313-7323 (2009)
9. T. Morikawa, H. Matsuda, I. Yamaguchi, Y. Pongpiriyadacha, M. Yoshikawa, Planta Med. 70, 152-159 (2004)
10. M.Y. Xia, L. Wang, Y.H. Wang, Nat. Prod. Res. Dev. 28, 1876-1885 (2016)
11. D.D. Ding, Y.H. Wang, Y.H. Chen, R.Q. Mei, J. Yang, J.F. Luo, Y. Li, C.L. Long, Y. Kong, Phytochemistry 129, 36-44 (2016)
12. D.D. Zhang, J. Yang, J.F. Luo, X.N. Li, C.L. Long, Y.H. Wang, J. Asian Nat. Prod. Res. 20, 734-743 (2018)
13. M.Y. Xia, J. Yang, P.H. Zhang, X.N. Li, J.F. Luo, C.L. Long, Y.H. Wang, Nat. Prod. Bioprospect. 8, 419-430 (2018)
14. O. Okitsu, R. Suzuki, S. Kobayashi, J. Org. Chem. 66, 809-823 (2001)
15. T. Iwasaki, H. Horikawa, K. Matsumoto, M. Miyoshi, J. Org. Chem. 44, 1552-1554 (1979)
16. S.G. Pardeshi, D.E. Ward, J. Org. Chem. 73, 1071-1076 (2008)
17. S. Das, D. Addis, S. Zhou, K. Junge, M. Beller, J. Am. Chem. Soc. 132, 1770-1771 (2010)
18. L. Dai, C. Zang, S. Tian, W. Liu, S. Tan, Z. Cai, T. Ni, M. An, R. Li, Y. Gao, D. Zhang, Y. Jiang, Bioorg. Med. Chem. Lett. 25, 34-37 (2015)
19. G.G. Zapesochnaya, V.A. Kurkin, Chem. Nat. Compd. 18, 685-688 (1982)
20. T. Morikawa, I. Yamaguchi, H. Matsuda, M. Yoshikawa, Chem. Pharm. Bull. 57, 1292-1295 (2009)
21. C. Glacet, G. Troude, Bull. Soc. Chim. Fr., 292-296 (1964)
22. F. Kiuchi, N. Nakamura, Y. Tsuda, K. Kondo, H. Yoshimura, Chem. Pharm. Bull. 36, 2452-2465 (1988)
23. S.A. Lee, J.S. Hwang, X.H. Han, C. Lee, M.H. Lee, S.G. Choe, S.S. Hong, D. Lee, M.K. Lee, B.Y. Hwang, Arch. Pharm. Res. 31, 679 (2008)
24. S. Wu, C. Sun, S. Pei, Y. Lu, Y. Pan, J. Chromatogr. A 1040, 193-204 (2004)
25. K. Li, W. Zhu, Q. Fu, Y. Ke, Y. Jin, X. Liang, Analyst 138, 3313-3320 (2013)
26. M.B. Tomas, T.C. Shiao, P.T. Nguyen, S. Bourgault, R. Roy, Pharm. Chem. J. 51, 995-1004 (2018)
27. I.K. Park, S.G. Lee, S.C. Shin, J.D. Park, Y.J. Ahn, J. Agric. Food Chem. 50, 1866-1870 (2002)
28. J.J. Chen, C.Y. Duh, H.Y. Huang, I.S. Chen, Helv. Chim. Acta 86, 2058-2064 (2003)
29. T. Narui, M. Takeuchi, R. Ishii, T. Ishida, T. Okuyama, Nat. Med. 49, 438-441 (1995)
30. H.J. Zhang, G.T. Tan, B.D. Santarsiero, A.D. Mesecar, N.V. Hung, N.M. Cuong, D. Doel Soejarto, J.M. Pezzuto, H.H.S. Fong, J. Nat. Prod. 66, 609-615 (2003)
31. K.O. Al-Footy, W.M. Alarif, M.S. Zubair, M.A. Ghandourah, M.M. Aly, Trop. J. Pharm. Res. 15, 1431-1438 (2016)
32. X.Y. Zhang, X.H. Cai, X.D. Luo, Chin. J. Nat. Med. 10, 36-39 (2012)
33. M. Ushiyama, T. Furuya, Phytochemistry 28, 3009-3013 (1989)
34. H. Otsuka, M. Yao, K. Kamada, Y. Takeda, Chem. Pharm. Bull. 43, 754-759 (1995)
35. J. O'Shea, C.S. Theile, R. Das, I.R. Babu, K. Charisse, M. Manoharan, M.A. Maier, I. Zlatev, Tetrahedron 74, 6182-6186 (2018)
36. T.R. Faruqi, E.J. Weiss, M.J. Shapiro, W. Huang, S.R. Coughlin, J. Biol. Chem. 275, 19728-19734 (2000)
37. M.D. Hollenberg, S. Mahmoud, S. Sabrina, H. Steeve, V. Nathalie, Br. J. Pharmacol. 143, 443-454 (2004)
38. S.L. French, J.R. Hamilton, Br. J. Pharmacol. 173, 2952-2965 (2016)
39. P.C. Wong, D. Seifert, J.E. Bird, C.A. Watson, J.S. Bostwick, M. Giancarli, N. Allegretto, J. Hua, D. Harden, J. Guay, Sci. Transl. Med. 9, eaaf5294 (2017)
40. Y.H. Wang, J.H. Wang, H.P. He, H. Zhou, X.W. Yang, C.S. Li, X.J. Hao, J. Asian Nat. Prod. Res. 10, 25-31 (2008)
41. W. Yi, Q. Li, J. Shen, L. Ren, X. Liu, Q. Wang, S. He, Q. Wu, H. Hu, X. Mao, L. Zhu, PloS ONE 9, e102394 (2014)
42. F. Maione, V. De Feo, E. Caiazzo, L. De Martino, C. Cicala, N. Mascolo, J. Ethnopharmacol. 155, 1236-1242 (2014)
43. W. Li, X. Tang, W. Yi, Q. Li, L. Ren, X. Liu, C. Chu, Y. Ozaki, J. Zhang, L. Zhu, PloS ONE 8, e85120 (2013)
44. D.P. Geraghty, K.D.K. Ahuja, J. Pittaway, C. Shing, G.A. Jacobson, N. Jager, S. Jurković, C. Narkowicz, C.I. Saunders, M. Ball, A. Pinkard, R.R. Vennavaram, M.J. Adams, J. Ethnopharmacol. 134, 97-103 (2011)

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