Biomolecules & Therapeutics  https://doi.org/10.4062/biomolther.2023.028
Chromatographic Determination of the Absolute Configuration in Sanjoinine A That Increases Nitric Oxide Production
Soohyun Um1,†, Hyeongju Jeong2,†, Joon Soo An3, Se Jin Jo2, Young Ran Kim2, Dong-Chan Oh3 and Kyuho Moon2,*
1College of Pharmacy, Yonsei Institute of Pharmaceutical Sciences, Yonsei University, Incheon 21983,
2College of Pharmacy, Research Institute of Pharmaceutical Sciences, Chonnam National University, Gwangju 61186,
3Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea
*E-mail: khmoon@jnu.ac.kr
Tel: +82-62-530-2934
†The first two authors contributed equally to this work.
Received: February 14, 2023; Revised: March 3, 2023; Accepted: March 9, 2023; Published online: April 6, 2023.
© The Korean Society of Applied Pharmacology. All rights reserved.

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/4.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
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: N,N-dimethyl amino acids, Phenylglycine methyl ester, Chemical derivatization, LC-MS analysis, Nitric oxide production

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