title: Absolute configuration of myrobotinol, new fused-hexacyclic alkaloid skeleton from Myrioneuron nutans.
abstract: Myrobotinol (1) was isolated from the leaves of Myrioneuron nutans (Rubiaceae) and its structure determined from spectral data, including mass spectrometry and 2D NMR. This compound presents a new hexacyclic alkaloid skeleton including a 1,3-oxazine and aminal functionality. The absolute configuration of myrobotinol was established by using Mosher's method. A plausible biosynthetic pathway starting from L-lysine via Delta-piperideine was proposed for this hexacyclic alkaloid.
authors.affiliation: Laboratoire de Chimie et Biochimie des Substances Naturelles-CNRS, Muséum National d'Histoire Naturelle, 63 rue Buffon, 75005 Paris, France. phamvc@ich.vast.ac.vn
authors.forename: Van Cuong
authors.initials: VC
authors.lastname: Pham
authors.forename: Akino
authors.initials: A
authors.lastname: Jossang
authors.forename: Thierry
authors.initials: T
authors.lastname: Sévenet
authors.forename: Van Hung
authors.initials: VH
authors.lastname: Nguyen
authors.forename: Bernard
authors.initials: B
authors.lastname: Bodo
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis / Q000737:chemistry / Q000302:isolation & purification*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D018515:Plant Leaves / Q000737:chemistry* / Q000378:metabolism; D012015:Reference Standards; D019666:Rubiaceae / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C526565:myrobotinol