title: Plantadeprate A, a Tricyclic Monoterpene Zwitterionic Guanidium, and Related Derivatives from the Seeds of Plantago depressa.
abstract: Two new alkaloids, plantadeprate A (1) and 1'-(4″-hydroxybutyl)plantagoguanidinic acid (2), along with three known compounds, were isolated from the seeds of Plantago depressa. Their structures were elucidated by physical data analyses including NMR, MS, and electronic circular dichroism (ECD) methods. Plantadeprate A (1), a monoterpene zwitterionic guanidium, possesses a unique 5/5/6-tricyclic ring system. Its absolute configuration was determined by X-ray crystallography and computational methods. Compound 1, plumbagine D (3), and plantagoguanidinic acid (4) exhibited potential antihyperglycemic properties attributed to suppression of hepatic gluconeogenesis with inhibitory rates of 8.2%, 18.5%, and 12.5% at 40 μM, respectively.
authors.forename: Xiu-Mian
authors.initials: XM
authors.lastname: Zheng
authors.affiliation: Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.|Department of Chemistry, College of Sciences, Shanghai University , Shanghai 200444, People's Republic of China.
authors.forename: Fan-Wang
authors.initials: FW
authors.lastname: Meng
authors.forename: Fang
authors.initials: F
authors.lastname: Geng
authors.forename: Meng
authors.initials: M
authors.lastname: Qi
authors.affiliation: Drug Discovery and Design Center, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, People's Republic of China.
authors.forename: Cheng
authors.initials: C
authors.lastname: Luo
authors.forename: Li
authors.initials: L
authors.lastname: Yang
authors.forename: Zheng-Tao
authors.initials: ZT
authors.lastname: Wang
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000806:Angiotensin-Converting Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005943:Gluconeogenesis / Q000187:drug effects; D006146:Guanidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D022781:Hepatocytes / Q000187:drug effects / Q000378:metabolism; D008968:Molecular Conformation; D015394:Molecular Structure; D039821:Monoterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010943:Plantago / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry
chemical_list: D000470:Alkaloids; D000806:Angiotensin-Converting Enzyme Inhibitors; D004365:Drugs, Chinese Herbal; D006146:Guanidines; D039821:Monoterpenes; C000605882:plantadeprate A; C000621445:plantagoguanidinic acid