Biomolecules & Therapeutics

The Korean Society of Applied Pharmacology (한국응용약물학회)
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Chromatographic Determination of the Absolute Configuration in Sanjoinine A That Increases Nitric Oxide Production

  • Soohyun Um (College of Pharmacy, Yonsei Institute of Pharmaceutical Sciences, Yonsei University) ;
  • Hyeongju Jeong (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Chonnam National University) ;
  • Joon Soo An (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Se Jin Jo (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Chonnam National University) ;
  • Young Ran Kim (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Chonnam National University) ;
  • Dong-Chan Oh (Natural Products Research Institute, College of Pharmacy, Seoul National University) ;
  • Kyuho Moon (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Chonnam National University)
  • Received : 2023.02.14
  • Accepted : 2023.03.09
  • Published : 2023.09.01
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Abstract

A chiral derivatization strategy with phenylglycine methyl ester (PGME) was employed to develop a straightforward method to determine the absolute configurations of N,N-dimethyl amino acids. The PGME derivatives were analyzed using liquid chromatography-mass spectrometry to identify the absolute configurations of various N,N-dimethyl amino acids based on their elution time and order. The established method was applied to assign the absolute configuration of the N,N-dimethyl phenylalanine in sanjoinine A (4), a cyclopeptide alkaloid isolated from Zizyphi Spinosi Semen widely used as herbal medicine for insomnia. Sanjoinine A displayed production of nitric oxide (NO) in LPS-activated RAW 264.7 cells.

Keywords

Acknowledgement

This research was supported by the National Research Foundation of Korea (NRF) grants funded by the Republic of Korean [2020R1F1A1072537, 2021R1C1C1009609, 2022R1A4A3022401, 2021R1A4A2001251, 2021R1I1A1A01049606] and Korea Basic Science Institute under the R&D program (Project No.C230430) supervised by the Ministry of Science and ICT.

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