title: Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production.
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.
authors.affiliation: 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.
authors.forename: Liguo
authors.initials: L
authors.lastname: Yang
authors.affiliation: 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.
authors.forename: Guan
authors.initials: G
authors.lastname: Wang
authors.affiliation: 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.
authors.forename: Meng
authors.initials: M
authors.lastname: Wang
authors.affiliation: 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.
authors.forename: Hongmei
authors.initials: H
authors.lastname: Jiang
authors.affiliation: 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.
authors.forename: Lixia
authors.initials: L
authors.lastname: Chen
authors.affiliation: School of Pharmacy, Yantai University, Yantai 264005, PR China. Electronic address: zhaofeng@ytu.edu.cn.
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.affiliation: 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.
authors.forename: Feng
authors.initials: F
authors.lastname: Qiu
mesh_terms: D000818:Animals; D053898:Biosynthetic Pathways; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000032:analysis; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D031219:Isatis / Q000737:chemistry*; D008264:Macrophages / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008516:Medicine, Chinese Traditional; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism*; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal
chemical_list: D004365:Drugs, Chinese Herbal; D006027:Glycosides; D026121:Indole Alkaloids; D009569:Nitric Oxide
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