A New Indole Alkaloid, 7 α-Hydroxy-7<i>H</i>-mitragynine, from<i>Mitragyna speciosa</i>in Thailand

Ponglux, Dhavadee; Wongseripipatana, Sumphan; Takayama, Hiromitsu; Kikuchi, Masae; Kurihara, Mika; Kitajima, Mariko; Aimi, Norio; Sakai, Shin‐ichiro

doi:10.1055/s-2006-959578

Cited by 134 publications

(119 citation statements)

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Section: Materials and Reagentsmentioning

confidence: 99%

“…Mitragynine was isolated from dried leaves of M. speciosa as described by Ponglux et al [16]. Synthesis of 7-hydroxymitragynine was performed in-house as reported earlier by Takayama et al and Ponglux et al [16,21]. Purities of mitragynine and 7-hydroxymitragynine were determined by 1H nuclear magnetic resonance (NMR), 13C NMR, high performance liquid chromatography, elemental analysis, and high-resolution mass spectrometry.…”

Section: Materials and Reagentsmentioning

confidence: 99%

“…Of these, the most clinically consequential are mitragynine and 7-hydroxymitragynine, compounds which are found exclusively in M. speciosa [6,14,15]. Mitragynine, a major indolecontaining constituent similar in structure to yohimbine [13], accounts for up to 66 % of the plant's alkaloid content [15,16]. It produces opioid-like effects predominantly via mu-and delta-opioid receptor agonism [5,13,17] in addition to modulation of the descending serotonergic and noradrenergic pathways [18].…”

Section: Introductionmentioning

confidence: 99%

“…1) [16]. Because auto-oxidation of mitragynine into 7-hydroxymitragynine occurs [16], this minor constituent may be an innate natural product or arise from mitragynine metabolism within the M. speciosa plant.…”

Section: Introductionmentioning

confidence: 99%

“…Because auto-oxidation of mitragynine into 7-hydroxymitragynine occurs [16], this minor constituent may be an innate natural product or arise from mitragynine metabolism within the M. speciosa plant. Accounting for roughly 2 % of the plant's alkaloid content [16], 7-hydroxymitragynine is an opioid receptor agonist (like mitragynine) but demonstrates potent mu and kappa receptor selectivity [12]. This alkaloid is the major contributing factor for Kratom's analgesic properties, demonstrating opioid receptor affinity up to 17 times that of morphine [20][21][22].…”

Section: Introductionmentioning

confidence: 99%

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Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

et al. 2016

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Introduction Kratom (Mitragyna speciosa), a plant native to Southeast Asia, has been used for centuries for its stimulant and opium-like effects. Mitragynine and 7-hydroxymitragynine, exclusive to M. speciosa, are the alkaloids primary responsible for Kratom's biologic and psychoactive profile, and likely contribute to its problematic use. We purchased several commercially available Kratom analogs for analysis and through our results, present evidence of probable adulteration with the highly potent and addictive plant alkaloid, 7-hydroxymitragynine. Methods A simple and sensitive LC-MS/MS method was developed for simultaneous quantification of mitragynine and 7-hydroxymitragynine in methanol extract of marketed Kratom supplements. Results We found multiple commercial Kratom products to have concentrations of 7-hydroxymitragynine that are substantially higher than those found in raw M. speciosa leaves. Conclusions We have found multiple packaged commercial Kratom products likely to contain artificially elevated concentrations of 7-hydroxymitragynine, the alkaloid responsible for M. speciosa's concerning mechanistic and side effect profile. This study describes a unique form of product adulteration, which stresses the importance of increased dietary supplement oversight of Kratom-containing supplements.

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Section: Materials and Reagentsmentioning

confidence: 99%

Section: Materials and Reagentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

et al. 2016

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Bioinspired Total Synthesis of Sespenine

et al. 2014

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The first total synthesis of sespenine, a rare indole sesquiterpenoid from a mangrove endophyte, has been accomplished. A bioinspired aza‐Prins/Friedel–Crafts/retro Friedel–Crafts cascade reaction assembles the bridged tetrahydroquinoline core. Further investigations on the aza‐Prins cyclization imply that the C3 configuration of the hydroxyindolenine intermediate is crucial to the biosynthesis of sespenine and its congener xiamycin A.

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Bioinspired Total Synthesis of Sespenine

et al. 2014

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The first total synthesis of sespenine, a rare indole sesquiterpenoid from a mangrove endophyte, has been accomplished. A bioinspired aza-Prins/Friedel-Crafts/retro Friedel-Crafts cascade reaction assembles the bridged tetrahydroquinoline core. Further investigations on the aza-Prins cyclization imply that the C3 configuration of the hydroxyindolenine intermediate is crucial to the biosynthesis of sespenine and its congener xiamycin A.

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A New Indole Alkaloid, 7 α-Hydroxy-7H-mitragynine, fromMitragyna speciosain Thailand

Cited by 134 publications

References 1 publication

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

Suspected Adulteration of Commercial Kratom Products with 7-Hydroxymitragynine

Bioinspired Total Synthesis of Sespenine

Bioinspired Total Synthesis of Sespenine

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