N-Acetyldopamine derivatives from Periostracum Cicadae and their regulatory activities on Th1 and Th17 cell differentiation

  • Punam Thapa
  • , Ye Gu
  • , Yun Seo Kil
  • , Su Cheol Baek
  • , Ki Hyun Kim
  • , Ah Reum Han
  • , Eun Kyoung Seo
  • , Hyukjae Choi
  • , Jae Hoon Chang
  • , Joo Won Nam

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

Bioassay-guided fractionation of a 90% ethanol extract of Periostracum Cicadae led to the isolation of two new N-acetyldopamine dimers (1a/1b) along with six known dimers (2a/2b, 3a/3b, and 4a/4b) and two monomers (5a/5b); compounds 2a/2b, 4a/4b and 5a/5b were newly isolated from this material. All compounds were isolated as enantiomeric mixtures and each enantiomer was successfully separated by chiral-phase HPLC. The structures including absolute configurations were confirmed by high-resolution electrospray ionization mass spectrometry (HR-ESIMS), 1D/2D nuclear magnetic resonance (NMR) spectroscopy, 1H iterative Full Spin Analysis (HiFSA), and electronic circular dichroism (ECD) spectroscopy. Subsequently, the bioactivities of these isolates were evaluated via CD4+ T cell differentiations, which are critical for immune responses and inflammation. The results revealed that compound 5b was observed to enhance the IFN-γ+ Th1 differentiation, which may have a potential for cancer immunotherapy.

Original languageEnglish
Article number104095
JournalBioorganic Chemistry
Volume102
DOIs
StatePublished - Sep 2020

Bibliographical note

Publisher Copyright:
© 2020 Elsevier Inc.

Keywords

  • CD4 T cell
  • Electronic circular dichroism (ECD) calculation
  • H iterative Full Spin Analysis (HiFSA)
  • N-acetyldopamine dimers
  • Periostracum Cicadae

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