New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

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 • Previous Articles Next 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

Received:2019-03-17 Revised:2019-04-21 Online:2019-06-05 Published:2019-06-24
Contact: Yi Kong, Yue-Hu Wang
Supported by:
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).

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

通讯作者: Yi Kong, Yue-Hu Wang
基金资助:
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).

Abstract

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.

Key words: Piper retrofractum, Piperaceae, Antiplatelet, Amides, Phenylpropanoids

摘要： 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.

关键词: Piper retrofractum, Piperaceae, Antiplatelet, Amides, Phenylpropanoids

Rong Tang, Ya-Qiong Zhang, Dong-Bao Hu, Xue-Fei Yang, Jun Yang, Myint Myint San, Thaung Naing Oo, Yi Kong, Yue-Hu Wang. 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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New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

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