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Phainanoids A-F, a new class of potent immunosuppressive triterpenoids with an unprecedented carbon skeleton from Phyllanthus hainanensis

Phainanoids A-F (1-6), six highly modified triterpenoids with a new carbon skeleton by incorporating two unique motifs of a 4,5- and a 5,5-spirocyclic systems, were isolated from Phyllanthus hainanensis. Their structures with absolute configurations were determined by spectroscopic data, chemical me... Full description

Journal Title: Journal of the American Chemical Society 14 January 2015, Vol.137(1), pp.138-41
Main Author: Fan, Yao-Yue
Other Authors: Zhang, Hua , Zhou, Yu , Liu, Hong-Bing , Tang, Wei , Zhou, Bin , Zuo, Jian-Ping , Yue, Jian-Min
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 25522036 Version:1 ; DOI: 10.1021/ja511813g
Link: http://pubmed.gov/25522036
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recordid: medline25522036
title: Phainanoids A-F, a new class of potent immunosuppressive triterpenoids with an unprecedented carbon skeleton from Phyllanthus hainanensis
format: Article
creator:
  • Fan, Yao-Yue
  • Zhang, Hua
  • Zhou, Yu
  • Liu, Hong-Bing
  • Tang, Wei
  • Zhou, Bin
  • Zuo, Jian-Ping
  • Yue, Jian-Min
subjects:
  • Carbon -- Chemistry
  • Immunosuppressive Agents -- Chemistry
  • Phyllanthus -- Chemistry
  • Triterpenes -- Chemistry
ispartof: Journal of the American Chemical Society, 14 January 2015, Vol.137(1), pp.138-41
description: Phainanoids A-F (1-6), six highly modified triterpenoids with a new carbon skeleton by incorporating two unique motifs of a 4,5- and a 5,5-spirocyclic systems, were isolated from Phyllanthus hainanensis. Their structures with absolute configurations were determined by spectroscopic data, chemical methods, and X-ray crystallography. Compounds 1-6 exhibited exceptionally potent immunosuppressive activities in vitro against the proliferation of T and B lymphocytes. The most potent one, phainanoid F (6), showed activities against the proliferation of T cells with IC50 value of 2.04 ± 0.01 nM (positive control CsA = 14.21 ± 0.01 nM) and B cells with IC50 value of
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 25522036 Version:1 ; DOI: 10.1021/ja511813g
fulltext: fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titlePhainanoids A-F, a new class of potent immunosuppressive triterpenoids with an unprecedented carbon skeleton from Phyllanthus hainanensis
creatorFan, Yao-Yue ; Zhang, Hua ; Zhou, Yu ; Liu, Hong-Bing ; Tang, Wei ; Zhou, Bin ; Zuo, Jian-Ping ; Yue, Jian-Min
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subjectCarbon -- Chemistry ; Immunosuppressive Agents -- Chemistry ; Phyllanthus -- Chemistry ; Triterpenes -- Chemistry
descriptionPhainanoids A-F (1-6), six highly modified triterpenoids with a new carbon skeleton by incorporating two unique motifs of a 4,5- and a 5,5-spirocyclic systems, were isolated from Phyllanthus hainanensis. Their structures with absolute configurations were determined by spectroscopic data, chemical methods, and X-ray crystallography. Compounds 1-6 exhibited exceptionally potent immunosuppressive activities in vitro against the proliferation of T and B lymphocytes. The most potent one, phainanoid F (6), showed activities against the proliferation of T cells with IC50 value of 2.04 ± 0.01 nM (positive control CsA = 14.21 ± 0.01 nM) and B cells with IC50 value of <1.60 ± 0.01 nM (CsA = 352.87 ± 0.01 nM), which is about 7 and 221 times as active as CsA, respectively. The structure-activity relationships of 1-6 are discussed.
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titlePhainanoids A-F, a new class of potent immunosuppressive triterpenoids with an unprecedented carbon skeleton from Phyllanthus hainanensis
descriptionPhainanoids A-F (1-6), six highly modified triterpenoids with a new carbon skeleton by incorporating two unique motifs of a 4,5- and a 5,5-spirocyclic systems, were isolated from Phyllanthus hainanensis. Their structures with absolute configurations were determined by spectroscopic data, chemical methods, and X-ray crystallography. Compounds 1-6 exhibited exceptionally potent immunosuppressive activities in vitro against the proliferation of T and B lymphocytes. The most potent one, phainanoid F (6), showed activities against the proliferation of T cells with IC50 value of 2.04 ± 0.01 nM (positive control CsA = 14.21 ± 0.01 nM) and B cells with IC50 value of <1.60 ± 0.01 nM (CsA = 352.87 ± 0.01 nM), which is about 7 and 221 times as active as CsA, respectively. The structure-activity relationships of 1-6 are discussed.
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abstractPhainanoids A-F (1-6), six highly modified triterpenoids with a new carbon skeleton by incorporating two unique motifs of a 4,5- and a 5,5-spirocyclic systems, were isolated from Phyllanthus hainanensis. Their structures with absolute configurations were determined by spectroscopic data, chemical methods, and X-ray crystallography. Compounds 1-6 exhibited exceptionally potent immunosuppressive activities in vitro against the proliferation of T and B lymphocytes. The most potent one, phainanoid F (6), showed activities against the proliferation of T cells with IC50 value of 2.04 ± 0.01 nM (positive control CsA = 14.21 ± 0.01 nM) and B cells with IC50 value of <1.60 ± 0.01 nM (CsA = 352.87 ± 0.01 nM), which is about 7 and 221 times as active as CsA, respectively. The structure-activity relationships of 1-6 are discussed.
doi10.1021/ja511813g
pmid25522036
date2015-01-14