title: A new prenylated naphthoquinoid from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze.
abstract: A new prenylated naphthoquinoid, named (3R,4aR,10bR)-3,10-dihydroxy-2,2-dimethyl-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b]-pyran-5H-6-one (1), was isolated from the aerial parts of Clinopodium chinense (Benth.) O. Kuntze, together with six known compounds: apigenin (2), luteolin (3), neoeriocitrin (4), naringenin (5), narirutin (6), and didymin (7). Neoeriocitrin was isolated for the first time from the species C. chinense. Their structures were elucidated by spectroscopic methods, including 1D, 2D (1H-1H-COSY, HSQC, HMBC and NOESY) NMR, HR-ESI-MS. The absolute configuration of 1 was determinated using the CD method. We highlight that the structure of 1 is characterized by a rarely seen prenylated naphthoquinoid framework.
authors.affiliation: Key Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100193, China. mingliangzhongsky@163.com
authors.forename: Mingliang
authors.initials: M
authors.lastname: Zhong
authors.forename: Guibo
authors.initials: G
authors.lastname: Sun
authors.forename: Xiaopo
authors.initials: X
authors.lastname: Zhang
authors.forename: Guangli
authors.initials: G
authors.lastname: Sun
authors.forename: Xudong
authors.initials: X
authors.lastname: Xu
authors.forename: Shichun
authors.initials: S
authors.lastname: Yu
mesh_terms: D004187:Disaccharides / Q000737:chemistry / Q000302:isolation & purification; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D044950:Flavanones / Q000737:chemistry / Q000302:isolation & purification; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification; D019686:Lamiaceae / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry / Q000302:isolation & purification; D035261:Plant Components, Aerial / Q000737:chemistry; D054876:Prenylation
chemical_list: D004187:Disaccharides; D004365:Drugs, Chinese Herbal; D044950:Flavanones; D005419:Flavonoids; D006027:Glycosides; D009285:Naphthoquinones; C552234:didymin; C553460:neoeriocitrin; C500601:narirutin; C005273:naringenin