Ophiorrhines F and G, Key Biogenetic Intermediates of Ophiorrhine Alkaloids from Ophiorrhiza japonica and Their Immunosuppressant Activities

J Nat Prod. 2022 Feb 25;85(2):453-457. doi: 10.1021/acs.jnatprod.1c01085. Epub 2022 Feb 1.

Abstract

Continued interest in bioactive alkaloids led to the isolation of two undescribed alkaloids, ophiorrhines F (1) and G (2), from the aerial parts of Ophiorrhiza japonica. Their structures were elucidated based on spectroscopic methods, electronic circular dichroism, and calculated NMR with DP4+ analysis. These two alkaloids represent key biological genetic intermediates in the formation of ring C in the ophiorrhines. Compound 1 exhibited good inhibition on LPS-induced B cell proliferation with an IC50 value of 0.38 μM and showed significant selective inhibitory activity on a B cell proliferation response with a selective index of 548.42. A preliminary study indicated that 1 may have a new mechanism of immunosuppression.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Cell Proliferation
  • Immunosuppressive Agents / pharmacology
  • Molecular Structure
  • Rubiaceae* / chemistry

Substances

  • Alkaloids
  • Immunosuppressive Agents