Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production

Liguo Yang; Guan Wang; Meng Wang; Hongmei Jiang; Lixia Chen; Feng Zhao; Feng Qiu

doi:10.1016/j.fitote.2014.03.019

Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production

Fitoterapia. 2014 Jun:95:175-81. doi: 10.1016/j.fitote.2014.03.019. Epub 2014 Mar 29.

Authors

Liguo Yang¹, Guan Wang¹, Meng Wang¹, Hongmei Jiang¹, Lixia Chen¹, Feng Zhao², Feng Qiu³

Affiliations

¹ Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.
² School of Pharmacy, Yantai University, Yantai 264005, PR China. Electronic address: zhaofeng@ytu.edu.cn.
³ Department of Natural Products Chemistry, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, PR China. Electronic address: fengqiu20070118@163.com.

PMID: 24685504
DOI: 10.1016/j.fitote.2014.03.019

Abstract

Three rare indole-2-S-glycosides, indole-3-acetonitrile-2-S-β-D-glucopyranoside (1), indole-3-acetonitrile-4-methoxy-2-S-β-D-glucopyranoside (2) and N-methoxy-indole-3-acetonitrile-2-S-β-D-glucopyranoside (3), together with 11 known indole alkaloids were isolated from the roots of Isatis indigotica Fort. (Cruciferae). The structures of 1-3 were elucidated on the basis of mass spectrometry and extensive 1D and 2D NMR spectroscopy. All of the isolated compounds were tested for inhibitory activity against LPS-induced nitric oxide production in RAW 264.7 macrophages. A plausible biosynthesis pathway of 1-3 is also proposed.

Keywords: 1-Methoxy-indole-3-acetonitrile (PubChem CID: 11954881); 3-Indoleacetic acid (PubChem CID: 802); 3-Indoleformic acid (PubChem CID: 69867); Anti-inflammatory activity; Arvelexin (PubChem CID: 119406); Indole alkaloids; Indole-2-S-glycosides; Indole-3-acetonitrile (PubChem CID: 351795); Isatis indigotica.

MeSH terms

Animals
Biosynthetic Pathways
Drugs, Chinese Herbal / chemistry
Drugs, Chinese Herbal / isolation & purification
Drugs, Chinese Herbal / pharmacology*
Glycosides / analysis
Indole Alkaloids / chemistry
Indole Alkaloids / isolation & purification
Indole Alkaloids / pharmacology*
Isatis / chemistry*
Macrophages / drug effects
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medicine, Chinese Traditional
Mice
Molecular Structure
Nitric Oxide / metabolism*
Plant Roots / chemistry
Plants, Medicinal

Substances

Drugs, Chinese Herbal
Glycosides
Indole Alkaloids
Nitric Oxide