Alopecines A-E, five chloro-containing matrine-type alkaloids with immunosuppressive activities from the seeds of Sophora alopecuroides.

Bioorg Chem

Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. Electronic address:

Published: June 2020

AI Article Synopsis

  • Researchers isolated five unique matrine-type alkaloids, named Alopecines A-E, from Sophora alopecuroides seeds, each featuring unusual chemical structures with dichlorocyclopropane or chloromethyl groups.
  • The structures of these alkaloids were determined using advanced techniques such as spectroscopy, X-ray diffraction, and computational methods.
  • Alkaloid 4 demonstrated strong inhibitory effects on the growth of specific immune cells, showing low effective concentration values (IC) of 3.98 μM for T lymphocytes and 3.74 μM for B cells.

Article Abstract

Alopecines A-E (1-5), five unusual matrine-type alkaloids featuring with an additional dichlorocyclopropane (1-3) or a di/tri-chloromethyl (4/5) attached on the D ring, were isolated from the seeds of Sophora alopecuroides. Their structures and absolute configurations were elucidated by extensive spectroscopic techniques, and X-ray diffraction analyses or time-dependent density functional theory-based electronic circular dichroism (TDDFT-ECD) calculations. Alkaloid 4 exhibited potent inhibitory effects on the proliferation of ConA-induced T lymphocytes or LPS-induced B cells with IC value of 3.98 or 3.74 μM, respectively.

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http://dx.doi.org/10.1016/j.bioorg.2020.103812DOI Listing

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Alopecines A-E, five chloro-containing matrine-type alkaloids with immunosuppressive activities from the seeds of Sophora alopecuroides.

Bioorg Chem

June 2020

Department of Natural Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China. Electronic address:

Article Synopsis
  • Researchers isolated five unique matrine-type alkaloids, named Alopecines A-E, from Sophora alopecuroides seeds, each featuring unusual chemical structures with dichlorocyclopropane or chloromethyl groups.
  • The structures of these alkaloids were determined using advanced techniques such as spectroscopy, X-ray diffraction, and computational methods.
  • Alkaloid 4 demonstrated strong inhibitory effects on the growth of specific immune cells, showing low effective concentration values (IC) of 3.98 μM for T lymphocytes and 3.74 μM for B cells.
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