Clavukoellians G-K, New Nardosinane and Aristolane Sesquiterpenoids with Angiogenesis Promoting Activity from the Marine Soft Coral Lemnalia sp

Mar Drugs. 2020 Mar 20;18(3):171. doi: 10.3390/md18030171.

Abstract

The chemical examination of the marine soft coral Lemnalia sp., collected at the Xisha islands in the South China Sea, resulted in the isolation of four new nardosinane-type sesquiterpenoids, namely clavukoellians G-J (1-4), and one new aristolane sesquiterpene, namely clavukoellian K (5), together with five known compounds, 6-10. The structure elucidation of the isolated natural products was based on various spectroscopic techniques including HRESIMS and NMR, while their absolute configurations were resolved on the basis of comparisons of the ECD spectra with the calculated ECD data. The isolated new compounds 1-5 were evaluated for their anti- and pro- angiogenesis activities in a transgenic fluorescent zebrafish (Tg(vegfr2:GFP)) model. Quantitative analysis revealed that compound 5 displayed pro-angiogenesis activity in a PTK787-induced vascular injury zebrafish model at 2.5 μM. Data showed that compound 5 significantly promoted the angiogenesis in a dose-dependent manner.

Keywords: Lemnalia sp.; angiogenesis promoting activity; aristolane; clavukoellian; nardosinane; sesquiterpenoid.

MeSH terms

  • Angiogenesis Inducing Agents / chemistry
  • Angiogenesis Inducing Agents / isolation & purification
  • Angiogenesis Inducing Agents / pharmacology*
  • Angiogenesis Inducing Agents / therapeutic use
  • Animals
  • Animals, Genetically Modified
  • Anthozoa / chemistry*
  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / pharmacology*
  • Biological Products / therapeutic use
  • Blood Vessels / drug effects*
  • China
  • Magnetic Resonance Spectroscopy
  • Models, Animal
  • Molecular Structure
  • Neovascularization, Physiologic / drug effects
  • Phthalazines / toxicity
  • Pyridines / toxicity
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Sesquiterpenes / therapeutic use
  • Zebrafish

Substances

  • Angiogenesis Inducing Agents
  • Biological Products
  • Phthalazines
  • Pyridines
  • Sesquiterpenes
  • vatalanib