Topic
Indole alkaloid
About: Indole alkaloid is a research topic. Over the lifetime, 868 publications have been published within this topic receiving 15401 citations. The topic is also known as: indole alkaloids.
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TL;DR: The observed lack of resolution of the indole alkaloid diastereoisomers coupled with the likeness of the mass and tandem mass spectra calls into question proposed GC methods for the analysis of mitragynine based on solely GC with MS separation and identification.
Abstract: Leaves of the Southeast Asian plant Mitragyna speciosa are used to suppress pain and mitigate opioid withdrawal syndromes. The potential threat of abuse and ready availability of this uncontrolled psychoactive plant have led to the need for improved analytical techniques for the detection of the major active components, mitragynine and 7-hydroxymitragynine. Three independent chromatographic methods coupled to two detection systems, GC with MS, supercritical fluid chromatography with diode array detection, and HPLC with MS and diode array detection, were compared for the analysis of mitragynine and other indole and oxindole alkaloids in M. speciosa plants. The indole alkaloids included two sets of diastereoisomers: (i) paynantheine and 3-isopaynantheine and (ii) mitragynine, speciogynine, and speciociliatine. Two oxindole alkaloid diastereoisomers, corynoxine and corynoxine B, were also studied. The HPLC and supercritical fluid chromatography methods successfully resolved the major components with slightly different elution orders. The GC method was less satisfactory because it was unable to resolve mitragynine and speciociliatine. This separation was difficult by GC with a liquid stationary phase because these diastereoisomers differ only in the orientation of an interior hydrogen atom. The observed lack of resolution of the indole alkaloid diastereoisomers coupled with the likeness of the mass and tandem mass spectra, calls into question proposed GC methods for the analysis of mitragynine based on solely GC with MS separation and identification.
46 citations
TL;DR: Chemical analysis showed that the seeds of Argyreia nervosa contain the highest percentage of indole alkaloid constituents (0.5-0.9%) of the genera of the Convolvulaceae thus far studied.
45 citations
TL;DR: The chiral total synthesis of mitragynine, a major corynanthe-type indole alkaloid having an analgesic effect in Mitragyna speciosa, was accomplished.
45 citations
TL;DR: In this article, a new indole alkaloid salvadoricine (I) has been isolated from Salvadora Persica and its structure was elucidated by spectral analysis and confirmed by synthesis.
44 citations
TL;DR: A synyhesis protocol involving beta-lithiation of 2-(2-pyridinyl)indoles (4 → 5) and subsequent reaction with bromoacetaldehyde leads to the indol[2,3-a]quinolzine(1) ring system.
44 citations