Yakugaku Zasshi. 2000 Oct;120(10):959-67.

[Chemical studies on the analgesic indole alkaloids from the traditional medicine (Mitragyna speciosa) used for opium substitute].

[Article in Japanese]

Source

Research Center of Medicinal Resources, Faculty of Pharmaceutical Sciences, Chiba University, Japan.

Abstract

The leaves of a tropical plant, Mitragyna speciosa Korth. (Rubiaceae), have been traditionally used as a substitute for opium. By phytochemical studies on the constituents of the plant growing in Thailand as well as in Malaysia, several 9-methoxy-Corynanthe-type monoterpenoid indole alkaloids including new natural products were isolated. The structures of these new compounds were elucidated by the modern spectroscopic methods and/or chiral-total syntheses. The chiral total synthesis of (-)-mitragynine, a major component of this plant, was achieved. Potent opioid agonistic properties of mitragynine, which acts on mu- and delta-opioid subtype receptors, and of mitragynine pseudoindoxyl, whose analgesic activity is more potent than that of morphine, were clarified in in vitro experiments. The essential structural features in mitragynine for revealing the analgesic activity were elucidated by pharmacological evaluation of the natural and synthetic mitragynine derivatives.

PMID:: 11082707; [PubMed - indexed for MEDLINE]

Publication Types, MeSH Terms, Substances

Publication Types

MeSH Terms

Substances

Supplemental Content

Related citations

Review Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa. [Chem Pharm Bull (Tokyo). 2004]
Review Chemistry and pharmacology of analgesic indole alkaloids from the rubiaceous plant, Mitragyna speciosa.
Takayama H. Chem Pharm Bull (Tokyo). 2004 Aug; 52(8):916-28.
Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands. [J Med Chem. 2002]
Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
Takayama H, Ishikawa H, Kurihara M, Kitajima M, Aimi N, Ponglux D, Koyama F, Matsumoto K, Moriyama T, Yamamoto LT, et al. J Med Chem. 2002 Apr 25; 45(9):1949-56.
Opioid receptor agonistic characteristics of mitragynine pseudoindoxyl in comparison with mitragynine derived from Thai medicinal plant Mitragyna speciosa. [Gen Pharmacol. 1999]
Opioid receptor agonistic characteristics of mitragynine pseudoindoxyl in comparison with mitragynine derived from Thai medicinal plant Mitragyna speciosa.
Yamamoto LT, Horie S, Takayama H, Aimi N, Sakai S, Yano S, Shan J, Pang PK, Ponglux D, Watanabe K. Gen Pharmacol. 1999 Jul; 33(1):73-81.
Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum. [Planta Med. 2005]
Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in guinea-pig ileum.
Horie S, Koyama F, Takayama H, Ishikawa H, Aimi N, Ponglux D, Matsumoto K, Murayama T. Planta Med. 2005 Mar; 71(3):231-6.
Review Mitragyna speciosa, a psychoactive tree from Southeast Asia with opioid activity. [Curr Top Med Chem. 2011]
Review Mitragyna speciosa, a psychoactive tree from Southeast Asia with opioid activity.
Adkins JE, Boyer EW, McCurdy CR. Curr Top Med Chem. 2011; 11(9):1165-75.

See reviews... See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.

Recent activity

Clear Turn Off Turn On

[Chemical studies on the analgesic indole alkaloids from the traditional medicin...
[Chemical studies on the analgesic indole alkaloids from the traditional medicine (Mitragyna speciosa) used for opium substitute].
Yakugaku Zasshi. 2000 Oct ;120(10):959-67.

PubMed
A simple physical model for binding energy hot spots in protein-protein complexe...
A simple physical model for binding energy hot spots in protein-protein complexes.
Proc Natl Acad Sci U S A. 2002 Oct 29 ;99(22):14116-21. Epub 2002 Oct 15 .

PubMed
Pancreatic neuroendocrine tumors among patients with intraductal papillary mucin...
Pancreatic neuroendocrine tumors among patients with intraductal papillary mucinous neoplasms: real association or just a coincidence?
JOP. 2009 Sep 4 ;10(5):515-7.

PubMed
Calcium and vitamin d supplementation decreases incidence of stress fractures in...
Calcium and vitamin d supplementation decreases incidence of stress fractures in female navy recruits.
J Bone Miner Res. 2008 May ;23(5):741-9.

PubMed
Heterologous expression of L. major proteins in S. cerevisiae: a test of solubil...
Heterologous expression of L. major proteins in S. cerevisiae: a test of solubility, purity, and gene recoding.
J Struct Funct Genomics. 2009 Sep ;10(3):233-47. Epub 2009 Aug 22 .

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Display Settings:

Send to:

[Chemical studies on the analgesic indole alkaloids from the traditional medicine (Mitragyna speciosa) used for opium substitute].

Source

Abstract

Publication Types, MeSH Terms, Substances

Publication Types

MeSH Terms

Substances

Supplemental Content

Related citations

Related information

Recent activity

Simple NCBI Directory

Getting Started

Resources

Popular

Featured

NCBI Information