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The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids
- Source :
- J Nat Prod
- Publication Year :
- 2020
- Publisher :
- American Chemical Society (ACS), 2020.
-
Abstract
- Two separate commercial products of kratom [Mitragyna speciosa (Korth.) Havil. Rubiaceae] were used to generate reference standards of its indole and oxindole alkaloids. While kratom has been studied for over a century, the characterization data in the literature for many of the alkaloids are either incomplete or inconsistent with modern standards. As such, full (1)H and (13)C NMR spectra, along with HRESIMS and ECD data, are reported for alkaloids 1-19. Of these, four new alkaloids (7, 11, 17, and 18) were characterized using 2D NMR data, and the absolute configurations of 7, 17, and 18 were established by comparison of experimental and calculated ECD spectra. The absolute configuration for the N(4)-oxide (11) was established by comparison of NMR and ECD spectra of its reduced product with those for compound 7. In total, 19 alkaloids were characterized, including: the indole alkaloid mitragynine (1) and its diastereoisomers speciociliatine (2), speciogynine (3) and mitraciliatine (4); the indole alkaloid paynantheine (5) and its diastereoisomers isopaynantheine (6) and epiallo-isopaynantheine (7); the N(4)-oxides mitragynine-N(4)-oxide (8), speciociliatine-N(4)-oxide (9), isopaynantheine-N(4)-oxide (10), and epiallo-isopaynantheine-N(4)-oxide (11); the 9-hydroxylated oxindole alkaloids speciofoline (12), isorotundifoleine (13) and isospeciofoleine (14); and the 9-unsubstituted oxindoles corynoxine A (15), corynoxine B (16), 3-epirhynchophylline (17), 3-epicorynoxine B (18), and corynoxeine (19). With the ability to analyze the spectroscopic data of all of these compounds concomitantly, a decision tree was developed to differentiate these kratom alkaloids based on a few key chemical shifts in the (1)H and/or (13)C NMR spectra.
- Subjects :
- Stereochemistry
Mitragyna speciosa
Pharmaceutical Science
01 natural sciences
Article
Indole Alkaloids
Analytical Chemistry
chemistry.chemical_compound
Drug Discovery
Oxindole
Pharmacology
Indole test
Molecular Structure
biology
Indole alkaloid
Mitragyna
010405 organic chemistry
Chemistry
Spectrum Analysis
Organic Chemistry
Absolute configuration
Stereoisomerism
Carbon-13 NMR
biology.organism_classification
0104 chemical sciences
010404 medicinal & biomolecular chemistry
Complementary and alternative medicine
Mitragynine
Molecular Medicine
Two-dimensional nuclear magnetic resonance spectroscopy
Subjects
Details
- ISSN :
- 15206025 and 01633864
- Volume :
- 83
- Database :
- OpenAIRE
- Journal :
- Journal of Natural Products
- Accession number :
- edsair.doi.dedup.....ec4527aad6d4ad65440d40c8067bdc14