title: 2-methyl-L-erythritol glycosides from Gardenia jasminoides.
abstract: Two new glycosides, 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (1) and 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside (2), along with two known triterpenoids (3-4), four quinic acid derivatives (5-8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-D-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-L-erythritol glycosides. Based on this finding, we propose that 2-methyl-L-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids.
authors.affiliation: Department of Natural Products Chemistry, School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China.
authors.forename: Liguo
authors.initials: L
authors.lastname: Yang
authors.forename: Kaifeng
authors.initials: K
authors.lastname: Peng
authors.forename: Shizhe
authors.initials: S
authors.lastname: Zhao
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.forename: Lixia
authors.initials: L
authors.lastname: Chen
authors.forename: Feng
authors.initials: F
authors.lastname: Qiu
mesh_terms: D000893:Anti-Inflammatory Agents / Q000302:isolation & purification* / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000494:pharmacology; D004896:Erythritol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D032062:Gardenia / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008070:Lipopolysaccharides; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis*; D013729:Terpenes / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: C586586:2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-beta-D-glucopyranoside; C586585:2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-beta-D-glucopyranoside; D000893:Anti-Inflammatory Agents; D004365:Drugs, Chinese Herbal; D006027:Glycosides; D008070:Lipopolysaccharides; D013729:Terpenes; D009569:Nitric Oxide; D004896:Erythritol
keywords: 2-Methyl-l-erythritol glycosides; Anti-inflammatory activity; Flavonoid; Gardenia jasminoides; Quinic acid derivatives; Triterpenoid