Absolute configuration of myrobotinol, new fused-hexacyclic alkaloid skeleton from Myrioneuron nutans.
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.
Pham
Van Cuong
VC
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
Jossang
Akino
A
Sévenet
Thierry
T
Nguyen
Van Hung
VH
Bodo
Bernard
B
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*
D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C526565:myrobotinol