Lignans with melanogenesis effects from Premna serratifolia wood

Fitoterapia. 2019 Mar:133:35-42. doi: 10.1016/j.fitote.2018.12.008. Epub 2018 Dec 17.

Abstract

Three new lignoids, premnan A (1), premnan B (2), and tauntangyiol C (3), were isolated from Premna serratifolia wood, a traditional cosmetic plant in Myanmar, together with a new lignoid, premnan C (4) assumed to be an artifact, one natural new lignoid (5), and three known lignoids (6-8). The structures of the new compounds 1-4 were elucidated based on 1D and 2D NMR, IR spectroscopy, and HRESIMS. The absolute configurations of 1-4 were also determined by optical rotation, circular dichroism (CD) data analyses, and comparisons with the reported literature. All isolated compounds were tested for their melanogenesis activities against the B16-F10 mouse melanoma cell line. Compounds 1 and 4 showed melanogenesis enhancing activities of 31% and 50%, respectively, at a 50 μM concentration. Compounds 2, 3, and 6 increased melanin production by 67%, 30%, and 45%, respectively, at a 100 μM concentration, without any cytotoxicity.

Keywords: Lignan; Melanogenesis enhancing activity; Premna serratifolia; Premnan Taungtangyiol.

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Lamiaceae / chemistry*
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Melanins
  • Melanoma, Experimental
  • Mice
  • Molecular Structure
  • Myanmar
  • Phytochemicals / isolation & purification
  • Phytochemicals / pharmacology
  • Wood / chemistry*

Substances

  • Antineoplastic Agents, Phytogenic
  • Lignans
  • Melanins
  • Phytochemicals