Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria

Dongdong Zhang; Yanhong Shi; Jingyi Li; Deqing Ruan; Qi Jia; Weiliang Zhu; Kaixian Chen; Yiming Li; Rui Wang

doi:10.3390/molecules24224033

Alkaloids with Nitric Oxide Inhibitory Activities from the Roots of Isatis tinctoria

Molecules. 2019 Nov 7;24(22):4033. doi: 10.3390/molecules24224033.

Authors

Dongdong Zhang¹, Yanhong Shi², Jingyi Li¹, Deqing Ruan¹, Qi Jia¹, Weiliang Zhu³, Kaixian Chen^{1

3}, Yiming Li¹, Rui Wang¹

Affiliations

¹ School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
² Institute of TCM International Standardization of Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
³ Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai 201203, China.

Abstract

As our ongoing research project on Ban Lan Gen (Isatis tinctoria roots), a total of 23 alkaloids were obtained. Compounds 1 and 2 contain an unusual C-C bond between the 2(1H)-quinolinone moiety and the phenol moiety and between the 2(1H)-quinolinone moiety and the 1H-indole moiety, respectively. Compound 3 possesses an unusual carbon skeleton and its putative biosynthetic pathway was discussed, and Compound 23 was deduced as a new indole alkaloid glycoside. Compounds 4-7 were identified as four new natural products by extensive spectroscopic experiments. Additionally, the anti-inflammatory activity was assessed based on nitric oxide (NO) production using Lipopolysaccharide-stimulated RAW264.7 macrophages. Compounds 9, 15, and 17 showed inhibitory effects with IC₅₀ values of 1.2, 5.0, and 74.4 μM.

Keywords: Isatis tinctoria roots; alkaloids; anti-inflammatory activity; structure identification.

MeSH terms

Alkaloids / chemistry*
Alkaloids / isolation & purification*
Isatis / chemistry*
Nitric Oxide / antagonists & inhibitors*
Nitric Oxide / chemistry*
Plant Roots / chemistry*

Substances

Alkaloids
Nitric Oxide