Structural and pharmacological diversity of 1,4-naphthoquinone glycosides in recent 20 years

Bioorg Chem. 2023 Sep:138:106643. doi: 10.1016/j.bioorg.2023.106643. Epub 2023 Jun 1.

Abstract

1,4-naphthoquinones are the most widespread naphthoquinone compounds. Recently, many 1,4-naphthoquinone glycosides with different structural features have been obtained from both nature and synthesis, which has led to an increasing variety of naphthoquinone glycosides. In this paper, the structure variety and biological activity in recent 20 years are reviewed, and classified them according to the source and structure characteristics. Meanwhile the synthetic methods of O-, S-, C- and N-naphthoquinone glycosides and their structure activity relationships are also described. It was referred that the presence of polar groups of C2 and C5 and non-polar groups attached to C3 on the naphthoquinone ring are beneficial for their biological activities. It will provide more comprehensive literature resources for the future research of 1, 4-naphthoquinone glycosides and lay a theoretical foundation.

Keywords: 1,4-naphthoquinone glycoside; Natural source; Pharmacological activity; Synthetic methods.

Publication types

  • Review
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosides* / chemistry
  • Glycosides* / pharmacology
  • Naphthoquinones* / chemistry
  • Naphthoquinones* / pharmacology
  • Structure-Activity Relationship

Substances

  • 1,4-naphthoquinone
  • Glycosides
  • Naphthoquinones