Mitraphylline

Last updated
Mitraphylline
Mitraphylline.svg
Names
IUPAC name
Methyl 19α-methyl-2-oxoformosanan-16-carboxylate
Systematic IUPAC name
Methyl (1′S,3R,4′aS,5′aS,10′aR)-1′-methyl-2-oxo-1,2,4′a,5′,5′a,7′,8′,10′a-octahydro-1′H,10′H-spiro[indole-3,6′-pyrano[3,4-f]indolizine]-4′-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.370 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-106-0
KEGG
PubChem CID
UNII
  • InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)/t12-,13-,14+,18-,21+/m0/s1 X mark.svgN
    Key: JMIAZDVHNCCPDM-DAFCLMLCSA-N X mark.svgN
  • C[C@H]1[C@H]2CN3CC[C@]4([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
Properties
C21H24N2O4
Molar mass 368.1736 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mitraphylline, an oxindole derivative, is an active alkaloid in the leaves of the tree Mitragyna speciosa , commonly known as kratom. [1] As a non-narcotic constituent, it also occurs to a significant amount in the bark of Uncaria tomentosa (Cat's Claw) along with a number of isomeric alkaloids. [2]

Current research is focusing on antiproliferative and cytotoxic effects and its in vivo efficacy to induce apoptosis in human breast cancer, sarcoma as well as lymphoblastic leukaemia cell lines. [3] [4] [5] [6] [7] [8]

Related Research Articles

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Tumors of the hematopoietic and lymphoid tissues or tumours of the haematopoietic and lymphoid tissues are tumors that affect the blood, bone marrow, lymph, and lymphatic system. Because these tissues are all intimately connected through both the circulatory system and the immune system, a disease affecting one will often affect the others as well, making aplasia, myeloproliferation and lymphoproliferation closely related and often overlapping problems. While uncommon in solid tumors, chromosomal translocations are a common cause of these diseases. This commonly leads to a different approach in diagnosis and treatment of hematological malignancies. Hematological malignancies are malignant neoplasms ("cancer"), and they are generally treated by specialists in hematology and/or oncology. In some centers "hematology/oncology" is a single subspecialty of internal medicine while in others they are considered separate divisions. Not all hematological disorders are malignant ("cancerous"); these other blood conditions may also be managed by a hematologist.

<i>Uncaria tomentosa</i> Species of plant

Uncaria tomentosa is a woody vine found in the tropical jungles of South and Central America. It is known as cat's claw or uña de gato in Spanish because of its claw-shaped thorns. The plant root bark is used in herbalism for a variety of ailments, and is sold as a dietary supplement.

The name Catuaba is used for the infusions of the bark of a number of trees native to Brazil. The most widely used barks are derived from the trees Trichilia catigua and Erythroxylum vaccinifolium. Other catuaba preparations use the bark of trees from the following genera or families: Anemopaegma, Ilex, Micropholis, Phyllanthus, Secondatia, Tetragastris and species from the Myrtaceae.

<span class="mw-page-title-main">Lactucopicrin</span> Chemical compound

Lactucopicrin (Intybin) is a bitter substance that has a sedative and analgesic effect, acting on the central nervous system. It is a sesquiterpene lactone, and is a component of lactucarium, derived from the plant Lactuca virosa, as well as being found in some related plants such as Cichorium intybus. It is also found in dandelion coffee.

<i>Mesembryanthemum tortuosum</i> Species of succulent

Mesembryanthemum tortuosum is a succulent plant in the family Aizoaceae native to the Cape Provinces of South Africa. It is known as kanna, channa, kougoed —which literally means, 'chew(able) things' or 'something to chew'.

<span class="mw-page-title-main">Mesembrine</span> Chemical compound

Mesembrine is an alkaloid present in Sceletium tortuosum (kanna). It has been shown to act as a serotonin reuptake inhibitor (Ki = 1.4 nM), and more recently, has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4) (Ki = 7,800 nM). In an in vitro study published in 2015, researchers concluded that "a high-mesembrine Sceletium extract" may exert anti-depressant effects by acting as a monoamine releasing agent." As such, mesembrine likely plays a dominant role in the antidepressant effects of kanna. The levorotatory isomer, (−)-mesembrine, is the natural form.

<i>Handroanthus impetiginosus</i> Species of tree

Handroanthus impetiginosus, the pink ipê, pink lapacho or pink trumpet tree, is a tree in the family Bignoniaceae, distributed throughout North, Central and South America, from northern Mexico south to northern Argentina. Along with all the other species in the Handroanthus genus, it is the national tree of Paraguay.

<span class="mw-page-title-main">Mitotic inhibitor</span> Cell division inhibitor

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<span class="mw-page-title-main">Rhynchophylline</span> Chemical compound

Rhynchophylline is an alkaloid found in certain Uncaria species (Rubiaceae), notably Uncaria rhynchophylla and Uncaria tomentosa. It also occurs in the leaves of Mitragyna speciosa (kratom), a tree native to Thailand. Chemically, it is related to the alkaloid mitragynine.

<i>Uncaria rhynchophylla</i> Species of plant

Uncaria rhynchophylla or the cat's claw herb is a plant species used in traditional Chinese medicine.

<span class="mw-page-title-main">Taspine</span> Chemical compound

Taspine is an alkaloid which acts as a potent acetylcholinesterase inhibitor and cicatrizant. It is found in various plants including Magnolia x soulangeana and Croton lechleri.

<i>Croton lechleri</i> Species of plant

Croton lechleri is a species of flowering plant in the spurge family, Euphorbiaceae, that is native to northwestern South America. It is commonly known as sangre de grado, sangre de drago or sangre de grada. They refer to this tree's thick red latex.

<span class="mw-page-title-main">Corydaline</span> Chemical compound

Corydaline is an acetylcholinesterase inhibitor isolated from Corydalis yanhusuo.

Corydalis yanhusuo is a plant species in the genus Corydalis. The Chinese name for Corydalis yanhusuo is yan hu suo. The Japanese common name is engosaku (エンゴサク) and the Korean common name is hyeonhosaek (현호색). English common names include yanhusuo, corydalis, and Asian corydalis. The tuber of this plant, frequently mislabeled as the root, is an important therapeutic agent in traditional Chinese medicine. It is native to high-altitude grasslands across China including in the provinces of Anhui, Henan, Hubei, Hunan, Jiangsu, and Zhejiang, but is more widely cultivated.

<span class="mw-page-title-main">Lunamarine</span> Chemical compound

Lunamarine (punarnavine) is a quinolone alkaloid present in Boerhavia diffusa (punarnava).

Uncaria perrottetii, known locally in the Philippines as “sungay kalabaw”, is a species of liana in the family Rubiaceae.

<span class="mw-page-title-main">Tabernaemontanine</span> Chemical compound

Tabernaemontanine is a naturally occurring monoterpene indole alkaloid found in several species in the genus Tabernaemontana including Tabernaemontana divaricata.

<span class="mw-page-title-main">Voacristine</span> Chemical compound

Voacristine is a indole alkaloid occurring in Voacanga and Tabernaemontana genus. It is also an iboga type alkaloid.

<span class="mw-page-title-main">Securinine</span> Chemical compound

Securinine is an alkaloid found in Securinega suffruticosa and Phyllanthus niruri.

References

  1. Manda, Vamshi; Avula, Bharathi; Ali, Zulfiqar; Khan, Ikhlas; Walker, Larry; Khan, Shabana (May 2014). "Evaluation of In Vitro Absorption, Distribution, Metabolism, and Excretion (ADME) Properties of Mitragynine, 7-Hydroxymitragynine, and Mitraphylline". Planta Medica. 80 (7): 568–576. doi:10.1055/s-0034-1368444. ISSN   0032-0943. PMID   24841968.
  2. Stuppner, H.; Sturm, S.; Konwalinka, G. (December 1992). "HPLC analysis of the main oxindole alkaloids from Uncaria tomentosa". Chromatographia. 34 (11–12): 597–600. doi:10.1007/BF02269869. ISSN   0009-5893. S2CID   95048480.
  3. García Giménez, Dolores; Prado, Elena García; Rodríguez, Teresa Sáenz; Arche, Angeles Fernández; Puerta, Rocío De la (February 2010). "Cytotoxic Effect of the Pentacyclic Oxindole Alkaloid Mitraphylline Isolated from Uncaria tomentosa Bark on Human Ewing's Sarcoma and Breast Cancer Cell Lines". Planta Medica. 76 (2): 133–136. doi:10.1055/s-0029-1186048. hdl: 11441/38905 . ISSN   0032-0943. PMID   19724995.
  4. Bacher, Nicole; Tiefenthaler, Martin; Sturm, Sonja; Stuppner, Hermann; Ausserlechner, Michael J.; Kofler, Reinhard; Konwalinka, Günther (March 2006). "Oxindole alkaloids from Uncaria tomentosa induce apoptosis in proliferating, G0/G1-arrested and bcl-2-expressing acute lymphoblastic leukaemia cells". British Journal of Haematology. 132 (5): 615–622. doi: 10.1111/j.1365-2141.2005.05907.x . ISSN   1365-2141. PMID   16445836.
  5. "Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (19α)-". webbook.nist.gov. Retrieved 2023-04-15.
  6. Rojas-Duran, R.; González-Aspajo, G.; Ruiz-Martel, C.; Bourdy, G.; Doroteo-Ortega, V. H.; Alban-Castillo, J.; Robert, G.; Auberger, P.; Deharo, E. (11 October 2012). "Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark". Journal of Ethnopharmacology. 143 (3): 801–804. doi:10.1016/j.jep.2012.07.015. PMID   22846434.
  7. Zhang, Qian; Zhao, Jiao Jiao; Xu, Jian; Feng, Feng; Qu, Wei (15 September 2015). "Medicinal uses, phytochemistry and pharmacology of the genus Uncaria". Journal of Ethnopharmacology. 173: 48–80. doi:10.1016/j.jep.2015.06.011. PMID   26091967.
  8. Montserrat-de la Paz, S.; de la Puerta, R.; Fernandez-Arche, A.; Quilez, A. M.; Muriana, F. J. G.; Garcia-Gimenez, M. D.; Bermudez, B. (21 July 2015). "Pharmacological effects of mitraphylline from Uncaria tomentosa in primary human monocytes: Skew toward M2 macrophages". Journal of Ethnopharmacology. 170: 128–135. doi:10.1016/j.jep.2015.05.002. hdl: 10261/124399 . PMID   25975515.