New Amides and Phenylpropanoid Glucosides from the Fruits of Piper retrofractum

  • Nat Prod Bioprospect. 2019 Jun;9(3):231-241. doi: 10.1007/s13659-019-0208-z.
Rong Tang  1  2 ,  Ya-Qiong Zhang  3 ,  Dong-Bao Hu  4 ,  Xue-Fei Yang  1  5 ,  Jun Yang  1  5 ,  Myint Myint San  6 ,  Thaung Naing Oo  6 ,  Yi Kong  7 ,  Yue-Hu Wang  8  9
Affiliations
  • 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. University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China.
  • 3. School of Life Science & Technology, China Pharmaceutical University, Nanjing, 210009, 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.
  • 7. School of Life Science & Technology, China Pharmaceutical University, Nanjing, 210009, People's Republic of China. [email protected].
  • 8. 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. [email protected].
  • 9. Southeast Asia Biodiversity Research Institute, Chinese Academy of Sciences, Yezin, Nay Pyi Taw, 05282, Myanmar. [email protected].
PMID: 31073809 DOI: 10.1007/s13659-019-0208-z
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 effect, with an inhibition ratio of 52.0% at a concentration of 150 μM.

Keywords
Amides; Antiplatelet; Phenylpropanoids; Piper retrofractum; Piperaceae.
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