2016
DOI: 10.1007/s13659-016-0113-7
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(±)-Evodiakine, A Pair of Rearranged Rutaecarpine-Type Alkaloids From Evodia rutaecarpa

Abstract: Abstract(±)-Evodiakine (1a and 1b), a pair of rearranged rutaecarpine-type alkaloids with an unprecedented 6/5/5/7/6 ring system, were isolated from the nearly ripe fruits of Evodia rutaecarpa. Separation of the enantiomers have been achieved by chiral HPLC column. The structures of (±)-evodiakine were unambiguously elucidated by 1D and 2D NMR spectra, mass spectrometry, and single-crystal X-ray diffraction. Their absolute configurations were determined by comparison of experimental and calculated electronic c… Show more

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Cited by 9 publications
(2 citation statements)
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“…Two pairs of rare indole-styrene hybrid derivatives 141a/141b and 142a/142b were isolated from Isatis indigotica [91]. The rearranged rutaecarpine-type indole alkaloid enantiomers 143a/143b from Evodia rutaecarpa incorporate an unprecedented 6/5/5/7/6 skeleton [92]. The dimeric isoechinulin-type indole alkaloid enantiomers 144a/144b and 145a/145b from Uncaria rhynchophylla feature an intriguing and complex skeleton with a symmetrical cyclobutane ring, and their rel.…”
Section: Indole Alkaloidsmentioning
confidence: 99%
“…Two pairs of rare indole-styrene hybrid derivatives 141a/141b and 142a/142b were isolated from Isatis indigotica [91]. The rearranged rutaecarpine-type indole alkaloid enantiomers 143a/143b from Evodia rutaecarpa incorporate an unprecedented 6/5/5/7/6 skeleton [92]. The dimeric isoechinulin-type indole alkaloid enantiomers 144a/144b and 145a/145b from Uncaria rhynchophylla feature an intriguing and complex skeleton with a symmetrical cyclobutane ring, and their rel.…”
Section: Indole Alkaloidsmentioning
confidence: 99%
“…Daphniphyllum alkaloids are a structurally diversified group of complex polycyclic natural products isolated from the Daphniphyllum genus [8]. Since these unique, versatile and complex nitrogen heterocyclic compounds exhibit a wide range of biological activities and are extremely challenging, they have aroused great interest in total synthesis and biosynthetic studies [9][10][11][12][13][14][15][16]. In recent years, quite a number of new Daphniphyllum alkaloids have been isolated and identified, and some of them possessed novel skeletons [17][18][19][20].…”
Section: Introductionmentioning
confidence: 99%