Literature DB >> 19731590

Phytochemical characterization of the leaves of Mitragyna speciosa grown in U.S.A.

Francisco León1, Eman Habib, Jessica E Adkins, Edward B Furr, Christopher R McCurdy, Stephen J Cutler.   

Abstract

Mitragyna speciosa (Rubiaceae) has traditionally been used in the tropical regions of Asia, Africa and Indonesia as a substitute for opium. Indole alkaloids are the most common compounds that have been isolated. We investigated the constituents of the leaves of M. speciosa that was grown at the University of Mississippi. Several alkaloids were isolated, including ajmalicine, corynantheidine, isomitraphylline, mitraphylline, paynantheine, isocorynantheidine, 7-hydroxymitragynine and mitragynine, but their percentages were lower than those in a commercial Thai sample of "kratom". In addition, we isolated the flavonoid epicatechin, a saponin daucosterol, the triterpenoid saponins quinovic acid 3-O-beta-D-quinovopyranoside, quinovic acid 3-O-beta-D-glucopyranoside, as well as several glycoside derivatives including 1-O-feruloyl-beta-D-glucopyranoside, benzyl-beta-D-glucopyranoside, 3-oxo-alpha-ionyl-O-beta-D-glucopyranoside, roseoside, vogeloside, and epivogeloside. This is the first report of the last group of compounds having been isolated from a Mitragyna species. Biological studies are currently underway to test these compounds for opioid activity.

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Year:  2009        PMID: 19731590      PMCID: PMC9255435     

Source DB:  PubMed          Journal:  Nat Prod Commun        ISSN: 1555-9475            Impact factor:   1.496


  13 in total

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Journal:  Chem Pharm Bull (Tokyo)       Date:  2005-10       Impact factor: 1.645

2.  A New Indole Alkaloid, 7 alpha-Hydroxy-7H-mitragynine, from Mitragyna speciosa in Thailand.

Authors:  D Ponglux; S Wongseripipatana; H Takayama; M Kikuchi; M Kurihara; M Kitajima; N Aimi; S Sakai
Journal:  Planta Med       Date:  1994-12       Impact factor: 3.352

3.  Self-treatment of opioid withdrawal with a dietary supplement, Kratom.

Authors:  Edward W Boyer; Kavita M Babu; Grace E Macalino; Wilson Compton
Journal:  Am J Addict       Date:  2007 Sep-Oct

4.  Phylogeny and classification of Naucleeae s.l. (Rubiaceae) inferred from molecular (ITS, rBCL, and tRNT-F) and morphological data.

Authors:  Sylvain G Razafimandimbison; Birgitta Bremer
Journal:  Am J Bot       Date:  2002-07       Impact factor: 3.844

5.  Ethnopharmacology of kratom and the Mitragyna alkaloids.

Authors:  K L Jansen; C J Prast
Journal:  J Ethnopharmacol       Date:  1988 May-Jun       Impact factor: 4.360

6.  Leishmanicidal, antiplasmodial and cytotoxic activity of indole alkaloids from Corynanthe pachyceras.

Authors:  D Staerk; E Lemmich; J Christensen; A Kharazmi; C E Olsen; J W Jaroszewski
Journal:  Planta Med       Date:  2000-08       Impact factor: 3.352

7.  Antinociception, tolerance and withdrawal symptoms induced by 7-hydroxymitragynine, an alkaloid from the Thai medicinal herb Mitragyna speciosa.

Authors:  Kenjiro Matsumoto; Syunji Horie; Hiromitsu Takayama; Hayato Ishikawa; Norio Aimi; Dhavadee Ponglux; Toshihiko Murayama; Kazuo Watanabe
Journal:  Life Sci       Date:  2005-09-15       Impact factor: 5.037

8.  Molecular analysis of the genus Mitragyna existing in Thailand based on rDNA ITS sequences and its application to identify a narcotic species: Mitragyna speciosa.

Authors:  Suchada Sukrong; Shu Zhu; Nijsiri Ruangrungsi; Thatree Phadungcharoen; Chanida Palanuvej; Katsuko Komatsu
Journal:  Biol Pharm Bull       Date:  2007-07       Impact factor: 2.233

Review 9.  The alkaloids of Mitragyna with special reference to those of Mitragyna speciosa, Korth.

Authors:  E J Shellard
Journal:  Bull Narc       Date:  1974 Apr-Jun

Review 10.  Opioid receptors and legal highs: Salvia divinorum and Kratom.

Authors:  Kavita M Babu; Christopher R McCurdy; Edward W Boyer
Journal:  Clin Toxicol (Phila)       Date:  2008-02       Impact factor: 4.467

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  20 in total

1.  The Chemistry of Kratom [Mitragyna speciosa]: Updated Characterization Data and Methods to Elucidate Indole and Oxindole Alkaloids.

Authors:  Laura Flores-Bocanegra; Huzefa A Raja; Tyler N Graf; Mario Augustinović; E Diane Wallace; Shabnam Hematian; Joshua J Kellogg; Daniel A Todd; Nadja B Cech; Nicholas H Oberlies
Journal:  J Nat Prod       Date:  2020-06-29       Impact factor: 4.050

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Authors:  Christopher D Rosenbaum; Stephanie P Carreiro; Kavita M Babu
Journal:  J Med Toxicol       Date:  2012-03

3.  Intrahepatic cholestasis following abuse of powdered kratom (Mitragyna speciosa).

Authors:  Friedrich G Kapp; Hans H Maurer; Volker Auwärter; Martin Winkelmann; Maren Hermanns-Clausen
Journal:  J Med Toxicol       Date:  2011-09

4.  Synthetic and Receptor Signaling Explorations of the Mitragyna Alkaloids: Mitragynine as an Atypical Molecular Framework for Opioid Receptor Modulators.

Authors:  Andrew C Kruegel; Madalee M Gassaway; Abhijeet Kapoor; András Váradi; Susruta Majumdar; Marta Filizola; Jonathan A Javitch; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2016-05-18       Impact factor: 15.419

Review 5.  Anti-ovarian cancer potential of phytocompound and extract from South African medicinal plants and their role in the development of chemotherapeutic agents.

Authors:  Chella Perumal Palanisamy; Bo Cui; Hongxia Zhang; Mani Panagal; Sivagurunathan Paramasivam; Uma Chinnaiyan; Selvaraj Jeyaraman; Karthigeyan Murugesan; Mauricio Rostagno; Vijayakumar Sekar; Srinivasa Prabhu Natarajan
Journal:  Am J Cancer Res       Date:  2021-05-15       Impact factor: 6.166

6.  Development and validation of a UPLC-MS/MS method for the determination of 7-hydroxymitragynine, a μ-opioid agonist, in rat plasma and its application to a pharmacokinetic study.

Authors:  Pradeep K Vuppala; Seshulatha Jamalapuram; Edward B Furr; Christopher R McCurdy; Bonnie A Avery
Journal:  Biomed Chromatogr       Date:  2013-07-25       Impact factor: 1.902

7.  Exploring the Chemistry of Alkaloids from Malaysian Mitragyna speciosa (Kratom) and the Role of Oxindoles on Human Opioid Receptors.

Authors:  Nelson Jeng-Yeou Chear; Francisco León; Abhisheak Sharma; Siva Rama Raju Kanumuri; Grant Zwolinski; Khalil A Abboud; Darshan Singh; Luis F Restrepo; Avi Patel; Takato Hiranita; Surash Ramanathan; Aidan J Hampson; Lance R McMahon; Christopher R McCurdy
Journal:  J Nat Prod       Date:  2021-02-26       Impact factor: 4.050

8.  Predicted Mode of Binding to and Allosteric Modulation of the μ-Opioid Receptor by Kratom's Alkaloids with Reported Antinociception In Vivo.

Authors:  Yuchen Zhou; Steven Ramsey; Davide Provasi; Amal El Daibani; Kevin Appourchaux; Soumen Chakraborty; Abhijeet Kapoor; Tao Che; Susruta Majumdar; Marta Filizola
Journal:  Biochemistry       Date:  2020-12-04       Impact factor: 3.162

Review 9.  Natural Products for the Treatment of Pain: Chemistry and Pharmacology of Salvinorin A, Mitragynine, and Collybolide.

Authors:  Soumen Chakraborty; Susruta Majumdar
Journal:  Biochemistry       Date:  2020-09-22       Impact factor: 3.162

Review 10.  Diversity in Chemical Structures and Biological Properties of Plant Alkaloids.

Authors:  Sweta Bhambhani; Kirtikumar R Kondhare; Ashok P Giri
Journal:  Molecules       Date:  2021-06-03       Impact factor: 4.411

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