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

Published on Sep 1, 2020in Bioorganic Chemistry5.275
· DOI :10.1016/J.BIOORG.2020.104095
Punam Thapa2
Estimated H-index: 2
 (Yeungnam University), Ye Gu1
Estimated H-index: 1
 (Yeungnam University)+ 7 AuthorsJoo-Won Nam21
Estimated H-index: 21
 (UIC: University of Illinois at Chicago)
Sources
Abstract
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.
📖 Papers frequently viewed together
20182.65The Journal of Antibiotics
7 Authors (Yasuhiro Igarashi)
20134.05Journal of Natural Products
5 Authors (Robert J. R. Jaeger, ..., Peter Spiteller)
20183.59New Journal of Chemistry
3 Authors (Krishnam Raju Ch, ..., Sanath Kumar Goud Palusa)
References31
Newest
Aug 11, 2017·Scientific Reports4.38
#1Wonhwa Lee (KNU: Kyungpook National University)H-Index: 30
#2Hee-Seung Lee (CNU: Chungnam National University)H-Index: 28
Last. Jong-Sup Bae (KNU: Kyungpook National University)H-Index: 48
view all 8 authors...
The edible grasshopper Oxya chinensis sinuosa is consumed worldwide for its various medicinal effects. The purpose of this study was to investigate potential bioactive antithrombotic and antiplatelet compounds from O. chinensis sinuosa. Five N-acetyldopamine dimers (1–5) were isolated from O. chinensis sinuosa and compounds 1 and 2 were identified as new chemicals with chiral centers at H-2 and H-3 of the benzo-1,4-dioxane structure. Compounds 1–4 were found to have both FXa and platelet aggrega...
Source
Aug 5, 2017·Archives of Pharmacal Research4.95
#1JungIn Lee (CNU: Chungnam National University)H-Index: 5
#2In Hyun Hwang (WU: Woosuk University)H-Index: 12
Last. MinKyun Na (CNU: Chungnam National University)H-Index: 41
view all 7 authors...
Edible insects have been reported to produce metabolites showing various pharmacological activities, recently emerging as rich sources of health functional food. In particular, the larvae of Protaetia brevitarsis seulensis (Kolbe) have been used as traditional Korean medicines for treating diverse diseases, such as breast cancer, inflammatory disease, hepatic cancer, liver cirrhosis, and hepatitis. However, only few chemical investigations were reported on the insect larvae. Therefore, the aim o...
Source
Jul 11, 2017·Scientific Reports4.38
#1Junsuk Kim (SNU: Seoul National University)H-Index: 7
#2Inhee Cho (SNU: Seoul National University)H-Index: 6
Last. Sung Jae Kim (SNU: Seoul National University)H-Index: 28
view all 4 authors...
Ion concentration polarization (ICP) is a fundamental electrokinetic process that occurs near a perm-selective membrane under dc bias. Overall process highly depends on the current transportation mechanisms such as electro-convection, surface conduction and diffusioosmosis and the fundamental characteristics can be significantly altered by external parameters, once the permselectivity was fixed. In this work, a new ICP device with a bifurcated current path as for the enhancement of the surface c...
Source
Oct 1, 2016·Fitoterapia2.88
#1Hong-Jie Zhu (CAS: Chinese Academy of Sciences)H-Index: 4
#2Yong-Ming Yan (CAS: Chinese Academy of Sciences)H-Index: 19
Last. Shu-Mei Wang (Guangdong Pharmaceutical University)H-Index: 9
view all 8 authors...
Abstract Plancyamides A (1) and B (3), plancypyrazine A (2), and plancyols A (4) and B (5), five new compounds (1–5), and three known ones (6–8), were isolated from the whole bodies of Polyphaga plancyi Bolivar. Their structures were elucidated by a combination of spectroscopic analyses including 1D and 2D NMR, and HRESIMS. Among them, compound 3 is racemic, chiral HPLC separation afforded its respective enantiomers. The absolute configuration of 1 was assigned by computational methods. Biologic...
Source
Melanin is an important biopolymeric pigment produced in a vast majority of organisms. Tyrosine and its hydroxylated product, dopa, form the starting material for melanin biosynthesis. Earlier studies by Raper and Mason resulted in the identification of dopachrome and dihydroxyindoles as important intermediates and paved way for the establishment of well-known Raper–Mason pathway for the biogenesis of brown to black eumelanins. Tyrosinase catalyzes the oxidation of tyrosine as well as dopa to do...
Source
Jun 1, 2016·Phytochemistry Letters1.68
#1Lu Yang (Shihezi University)H-Index: 3
#2Guo-Yu Li (Shihezi University)H-Index: 15
Last. Jinhui Wang (Shihezi University)H-Index: 15
view all 8 authors...
Abstract Periostracum Cicadae, the cast-off shell of the cicada Cryptotympana pustulata Fabricius, is used in traditional Chinese medicine for its diaphoretic, anticonvulsive, sedative, antipyretic, and antiallergic effects. Five new N - acetyldopamine dimers were isolated from Periostracum Cicadae, and their structures were elucidated as (2 R ,3 S )-2-(3′,4′-dihydroxyphenyl)-3-acetylamino-7-( N- acetyl-2′′-aminoethyl)-1,4-benzodioxane 3′- O -β- d -glucopyranoside ( 1 ), (2 S ,3 R )-2-(3′,4′-dih...
Source
Aug 27, 2015·Molecules4.41
#1Juan LuH-Index: 1
#2Qin SunH-Index: 1
Last. Yong-Xian Cheng (CAS: Chinese Academy of Sciences)H-Index: 25
view all 6 authors...
Recent studies focusing on identifying the biological agents of Catharsius molossus have led to the identification of three new N-acetyldopamine dimers molossusamide A-C (1-3) and two known compounds 4 and 5. The structures of the new compounds were identified by comprehensive spectroscopic evidences. Compound 4 was found to have inhibitory effects towards COX-1 and COX-2.
Source
Jan 21, 2015·Journal of Asian Natural Products Research1.57
#1Jian-Jun Tang (CDUTCM: Chengdu University of Traditional Chinese Medicine)H-Index: 1
#2Qi Luo (CAS: Chinese Academy of Sciences)H-Index: 14
Last. Yong-Xian Cheng (CDUTCM: Chengdu University of Traditional Chinese Medicine)H-Index: 25
view all 10 authors...
Two new dopamine derivatives divesamides A (1) and B (2), along with six known N-containing compounds were isolated from the Chinese black ant (Polyrhachis dives). Their structures were determined on the basis of spectroscopic methods. Compound 1 is a racemate, and chiral HPLC separation yielded a pair of antipodes. The absolute configuration of (+)-1 was assigned by a computational method. The double signals in the H-1 and C-13 NMR spectra of 2 that resulted from the presence of a formamide gro...
Source
Nov 18, 2014·Tetrahedron2.46
#1Jian-Jun ab Tang (CAS: Chinese Academy of Sciences)H-Index: 1
#2Li Zhang (Academy of Medical Sciences, United Kingdom)H-Index: 9
Last. Yong-Xian Cheng (CAS: Chinese Academy of Sciences)H-Index: 25
view all 12 authors...
Polyrhachis dives is consumed as an insect food in some regions of China. In this study, new dopamine derivatives, (+)-polyrhadopamine A (1a) and (-)-polyrhadopamine A (1b), (+)-polyrhadopamine B (2a) and (-)-polyrhadopamine B (2b), and polyrhadopamines C-E (3-5), were isolated from this species. The structures and stereochemistry of these substances were assigned by using spectroscopic and computational methods. Compounds 1a, 1b, 2a, and 2b are dimeric N-acetyldopamine derivatives, 3 is a dopam...
Source
Nov 15, 2014·Bioorganic & Medicinal Chemistry Letters2.82
#1Yan-Ni Shi (CAS: Chinese Academy of Sciences)H-Index: 4
#2Zhengchao Tu (Guangzhou Institutes of Biomedicine and Health)H-Index: 29
Last. Yong-Xian Cheng (CAS: Chinese Academy of Sciences)H-Index: 25
view all 9 authors...
Recent studies focusing on unveiling the biological agents of Aspongopus chinensis have led to the identification of four new norepinephrine derivatives (1-4), three new sesquiterpenoids (5-7), and one new lactam (8). In addition, twenty-three known compounds have been identified, most of which were isolated from this insect for the first time. Selected members of insect-derived substances were evaluated for their biological activities against renal protection in high-glucose-induced mesangial c...
Source
1234
Cited By3
Newest
Jul 20, 2021·Oxidative Medicine and Cellular Longevity6.54
#1Q.M. Zhang (CDUTCM: Chengdu University of Traditional Chinese Medicine)H-Index: 28
Cicadae Periostracum (CPM), a commonly used animal traditional Chinese medicine (TCM), possesses antifebrile, spasmolytic, antiasthmatic, and antiphlogistic effects. In our present paper, we aimed to systemically investigate the antiepileptic effects of CPM in epileptic mice and explore the related molecular mechanism. Pentylenetetrazole- (PTZ) and strychnine-induced convulsion mice were established, and the results showed CPM could prolong the latency of convulsion and death and improve the neu...
Source
Mar 25, 2021·Molecules4.41
#1Seung-Hyung Kim (Daejeon University)H-Index: 24
#2Jung-hee Hong (Sangji University)H-Index: 6
Last. Young-Cheol Lee (Sangji University)H-Index: 15
view all 6 authors...
Cicadae Periostracum (CP), derived from the slough of Cryptotympana pustulata, has been used as traditional medicine in Korea and China because of its diaphoretic, antipyretic, anti-inflammatory, antioxidant, and antianaphylactic activities. The major bioactive compounds include oleic acid (OA), palmitic acid, and linoleic acid. However, the precise therapeutic mechanisms underlying its action in asthma remain unclear. The objective of this study was to determine the antiasthmatic effects of CP ...
Source
Jan 1, 2021·Bioorganic Chemistry5.28
#1Punam Thapa (Yeungnam University)H-Index: 2
#2Nikita Katila (Yeungnam University)H-Index: 8
Last. Joo-Won Nam (Yeungnam University)H-Index: 9
view all 5 authors...
Abstract Suntamide A (1), a new cyclic peptide, was isolated from Cicadidae Periostracum. The gross structure of 1 was elucidated by detailed analysis of HRMS and 1D/2D NMR spectra, and the absolute configuration was established by C3 Marfey’s method. We extended our study to examine biological activity of 1, and found that 1 protected SH-SY5Y cells against rotenone-induced neurotoxicity. This effect of 1 seemed to be attributed to antioxidant induction and protection of mitochondria from roteno...
Source
1
This website uses cookies.
We use cookies to improve your online experience. By continuing to use our website we assume you agree to the placement of these cookies.
To learn more, you can find in our Privacy Policy.