The efficient synthesis and biological evaluation of justicidin B.
Taejung KimYoung-Joo KimKyu-Hyuk JeongYoung-Tae ParkHyukjoon KwonPilju ChoiHa-Neul JuCheol Hee YoonJi-Yool KimJungyeob HamPublished in: Natural product research (2021)
A facile new synthetic method for the preparation of a Type-A 1-arylnaphthalene lactone skeleton was developed and used to synthesise justicidin B and several derivatives. Key synthesis steps included Hauser-Kraus annulation of a phthalide intermediate and Suzuki-Miyaura cross coupling between a triflated naphthalene lactone intermediate and various potassium organotrifluoroborates. With two exceptions, the derivatives showed significant inhibitory effect on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophages. Moreover, several compounds, including justicidin B, had marked cytotoxicity towards six human tumour cell lines.
Keyphrases
- lps induced
- inflammatory response
- nitric oxide
- endothelial cells
- structure activity relationship
- hydrogen peroxide
- induced pluripotent stem cells
- toll like receptor
- quantum dots
- nitric oxide synthase
- pluripotent stem cells
- molecularly imprinted
- reduced graphene oxide
- immune response
- gold nanoparticles
- high resolution
- visible light
- simultaneous determination