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

doi:10.1016/j.bioorg.2020.104095

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

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

19 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 language	English
Article number	104095
Journal	Bioorganic Chemistry
Volume	102
DOIs	https://doi.org/10.1016/j.bioorg.2020.104095
State	Published - 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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title = "N-Acetyldopamine derivatives from Periostracum Cicadae and their regulatory activities on Th1 and Th17 cell differentiation",

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.",

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

author = "Punam Thapa and Ye Gu and Kil, {Yun Seo} and Baek, {Su Cheol} and Kim, {Ki Hyun} and Han, {Ah Reum} and Seo, {Eun Kyoung} and Hyukjae Choi and Chang, {Jae Hoon} and Nam, {Joo Won}",

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year = "2020",

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doi = "10.1016/j.bioorg.2020.104095",

language = "English",

volume = "102",

journal = "Bioorganic Chemistry",

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AU - Thapa, Punam

AU - Gu, Ye

AU - Kil, Yun Seo

AU - Baek, Su Cheol

AU - Kim, Ki Hyun

AU - Han, Ah Reum

AU - Seo, Eun Kyoung

AU - Choi, Hyukjae

AU - Chang, Jae Hoon

AU - Nam, Joo Won

PY - 2020/9

Y1 - 2020/9

N2 - 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.

AB - 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.

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

Abstract

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Keywords

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