Three New Isoprenylated Flavones from Artocarpus chama Stem and Their Bioactivities

Molecules. 2021 Dec 21;27(1):3. doi: 10.3390/molecules27010003.

Abstract

Phytochemical investigation of Artocarpus chama stem was performed by chromatographic techniques, resulting from the isolation and structure elucidation of three new compounds, namely 3'-farnesyl-apigenin (1), 3-(hydroxyprenyl) isoetin (2), and 3-prenyl-5,7,2',5'-tetrahydroxy-4'-methoxyflavone (3), and five known compounds, namely homoeriodictyol (4), isocycloartobilo-xanthone (5), artocarpanone (6), naringenin (7), and artocarpin (8). From the screening result, A. chama extract showed a potent tyrosinase inhibitory effect. Ihe isolated compounds 1, 4 and 6 also exhibited tyrosinase inhibition with IC50 of 135.70, 52.18, and 38.78 µg/mL, respectively. Moreover, compounds 3, 4, 5, 6, and 8 showed strong activity against Staphylococcus epidermidis, S. aureus, methicillin-resistant S. aureus, and Cutibacterium acnes. This study is the first report on phytochemical investigation with new compounds and biological activities of A. chama. Skin infection can cause dark spots or hyperpigmentation. The isolated compounds that showed both anityrosinase and antimicrobial activities will be further studied in in vivo and clinical trials in order to develop treatment for hyperpigmentation, which is caused by infectious diseases by microorganisms.

Keywords: Artocarpus charma; antimicrobial activity; antityrosinase activity; isoprenylated flavone; melanin content; moraceae.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Artocarpus / chemistry*
  • Drug Evaluation, Preclinical
  • Flavanones / chemistry
  • Flavones / chemistry*
  • Flavones / pharmacology
  • Humans
  • Mannose-Binding Lectins / chemistry
  • Methicillin-Resistant Staphylococcus aureus / drug effects
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Plant Lectins / chemistry
  • Plant Stems / chemistry*
  • Prenylation
  • Staphylococcus epidermidis / drug effects
  • Xanthones / chemistry

Substances

  • Anti-Bacterial Agents
  • Flavanones
  • Flavones
  • Mannose-Binding Lectins
  • Plant Extracts
  • Plant Lectins
  • Xanthones
  • artocarpanone
  • artocarpin lectin
  • xanthone
  • homoeriodictyol
  • naringenin