“…Then, the C-3/N-4 bond cleavage and the formation of a heptatomic ring accomplished via the key intermediate C [12]. The rings C and D rearrangement of B via attack of the NH in C onto the imine carbon yielded the structure D , which was followed by reduction of the C-5/C-6 double bond to produce compounds 1a and 1b [13, 14]. Scheme 1Plausible biogenetic pathway of (+)- 1a and (−)- 1b
…”
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 circular dichroism spectra. A hypothetical biogenetic pathway for (±)-evodiakine was also proposed. Compounds 1a, 1b, and the racemate (1) were tested for their cytotoxic and anti-inflammatory activities.Graphical Abstract
Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0113-7) contains supplementary material, which is available to authorized users.
“…Then, the C-3/N-4 bond cleavage and the formation of a heptatomic ring accomplished via the key intermediate C [12]. The rings C and D rearrangement of B via attack of the NH in C onto the imine carbon yielded the structure D , which was followed by reduction of the C-5/C-6 double bond to produce compounds 1a and 1b [13, 14]. Scheme 1Plausible biogenetic pathway of (+)- 1a and (−)- 1b
…”
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 circular dichroism spectra. A hypothetical biogenetic pathway for (±)-evodiakine was also proposed. Compounds 1a, 1b, and the racemate (1) were tested for their cytotoxic and anti-inflammatory activities.Graphical Abstract
Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-016-0113-7) contains supplementary material, which is available to authorized users.
“…Structural elucidation of the product The product (2) (Zhang et al 2014). Besides the indole ring, the alkaloid possessed: a methoxycarbonyl group, a tri-substituted olefinic bond, five methylene carbons (including an oxygen-bearing and a nitrogen-bearing methylene carbons), two methane carbons (including a nitrogen-bearing methane carbon) and a quaternary carbon and a methyl group.…”
“…Delphinidin glycosides have been isolated from the flowers of V. major [6] while chlorogenic acid, robinin, and flavonol triglycoside are extracted from its leaves [7]. In addition, a number of indole alkaloids are also reported from this plant [8–13]. Previously, we isolated non-alkaloid constituents [14] as well as indole alkaloids [15] from V. major cultivated in Kunming.…”
Three new pyridine type alkaloids, (−)-vinmajpyridines A–C (1–3), along with two known alkaloids, have been isolated from the aerial parts of Vinca major cultivated in Pakistan. Their structures have been elucidated by means of NMR and HRESIMS spectroscopic data. The new alkaloids were evaluated for their cytotoxicity against glioma initiating cell lines (GITC-3# and GITC-18#), glioblastoma cell lines (U-87MG and T98G), and lung cancer cell line A-549, but none of them was active at 20 μg/mL concentration.Electronic supplementary materialThe online version of this article (doi:10.1007/s13659-017-0137-7) contains supplementary material, which is available to authorized users.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.
