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

Article abstract of DOI:10.1021/ja511813g

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 <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.

Full text of DOI:10.1021/ja511813g

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Communication
Phainanoids A–F, A New Class of Potent Immunosuppressive Triterpenoids
with an Unprecedented Carbon Skeleton from Phyl-lanthus hainanensis
Yao-Yue Fan, Hua Zhang, Yu Zhou, Hong-Bing Liu, Wei Tang, Bin Zhou, Jian-Ping Zuo, and Jian-Min Yue
J. Am. Chem. Soc., Just Accepted Manuscript • DOI: 10.1021/ja511813g • Publication Date (Web): 18 Dec 2014
Downloaded from http://pubs.acs.org on December 20, 2014
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