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

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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
StatePublished - Sep 2020

Bibliographical note

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© 2020 Elsevier Inc.


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


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