Serotonin transporter protein (SERT) and P-glycoprotein (P-gp) binding activity of montanine and coccinine from three species of Haemanthus L. (Amaryllidaceae)

South African Journal of Botany

Volumn 88, Issue , 2013, Pages 101-106

  Stafford, G I ^a   Birer, C ^b   Brodin, B ^b   Christensen, S Brøgger ^b   Eriksson, A H ^b   Jager A K ^b   Ronsted N ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Alkaloids; Amaryllidaceae; Blood brain barrier; Calcein AM; Coccinine; Haemanthus; MDCK(II) MDR1; Montanine; P glycoprotein; Serotonin transporter protein

Indexed keywords

ALKALOID; CHEMICAL BINDING; DICOTYLEDON; GAS CHROMATOGRAPHY; INHIBITION; MASS SPECTROMETRY; PROTEIN;

EID: 84880385040     PISSN: 02546299     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.sajb.2013.06.002     Document Type: Article

References (25)

1. Bay-Smidt M.G.K., Jäger A.K., Krydsfeldt K., Meerow A.W., Stafford G.I., van Staden J., Rønsted N. Phylogenetic selection of target species in Amaryllidaceae tribe Haemantheae for acetylcholinesterase inhibition and affinity to the serotonin reuptake transport protein. South African Journal of Botany 2011, 77:175-183.
2. Berkov S., Bastida J., Viladomat F., Codina C. Analysis of galanthamine-type alkaloids by capillary gas chromatographymass spectrometry in plants. Phytochemical Analysis 2008, 19:285-293.
3. Crouch N.R., Pohl T.L., Mulholland D.A., Ndlovu E. Alkaloids from three ethnomedicinal Haemanthus species: H. albiflos, H. deformis and H. pauculifolius (Amaryllidaceae). South African Journal of Botany 2005, 71:49-52.
4. da Silva A.F.S., de Andrade J.P., Bevilaqua L.R.M., de Souza M.M., Izquierdo I., Henriques A.T., Zuanazzi J.A.S. Anxiolytic-, antidepressant- and anticonvulsant-like effects of the alkaloid montanine isolated from Hippeastrum vittatum. Pharmacology, Biochemistry, and Behavior 2006, 85:148-154.
5. Dold T., Cocks M. Indigenous plant use of the amaXhosa people on the eastern border of the Great Fish River Reserve, Eastern Cape. Annals of Eastern Cape Museums 2000, 1:26-53.
6. 3H] citalopram binding to the rat brain serotonin transporter by Amaryllidaceae alkaloids. Planta Medica 2006, 72:470-473.
7. Eriksson A.H., Rønsted N., Güler S., Jäger A.K., Sendra J.R., Brodin B. Structurally related, potentially CNS-active Amaryllidaceae alkaloids, show differential interactions with p-glycoprotein. The Journal of Pharmacy and Pharmacology 2012, 64:1667-1677.
8. Inubushi Y., Fales H.M., Warnhoff E.W., Wildman W.C. Structures of montanine, coccinine, and manthine. The Journal of Organic Chemistry 1960, 25:2153-2164.
9. Ishizaki M.M., Hoshino O. Total synthesis of montanine-type Amaryllidaceae alkaloids which possess a 5, 11-methanomorphanthridine ring system, through cyclisation with sodium bis (2-methoxyethoxy) aluminium hydride: the first stereoselective synthesis of montanine, coccinine, O-acetylmontanine, pancracine and brunsvigine. The Journal of Organic Chemistry 1992, 57:7285-7295.
10. Jin Z. Amaryllidaceae and Sceletium alkaloids. Natural Product Reports 2009, 26:363-381.
11. Jin J., Weinreb S.M. Application of a stereospecific intramolecular allenylsilane iminoene reaction to enantioselective total synthesis of the 5,11-methanomorphanthridine class of Amaryllidaceae alkaloids. Journal of the American Chemical Society 1997, 119:5773-5784.
12. Larsen M.M., Adsersen A.A., Davis A.P., Lledó M.D., Jager A.K., Rønsted N. Using a phylogenetic approach to selection of target plants in drug discovery of acetylcholinesterase inhibiting alkaloids in Amaryllidaceae tribe Galantheae. Biochemical Systematics and Ecology 2010, 38:1026-1034.
13. Li W.-X., Li L., Eksterowicz J., Ling X.B., Cardozo M. Significance analysis and multiple pharmacophore models for differentiating P-glycoprotein substrates. Journal of Chemical Information and Modeling 2007, 47:2429-2438.
14. Neergaard J.S., Andersen J., Pedersen M.E., Stafford G.I., van Staden J., Jäger A.K. Alkaloids from Boophone disticha with affinity to the serotonin transporter. South African Journal of Botany 2009, 75:371-374.
15. Nielsen N.D., Sandager M., Stafford G.I., Van Staden J., Jäger A.K. Screening of indigenous plants from South Africa for affinity to the serotonin reuptake transport protein. Journal of Ethnopharmacology 2004, 94:159-163.
16. Pagliosa L.B., Monteiro S.C., Silva K.B., de Andrade J.P., Dutilh J., Bastida J., Cammarota M., Zuanazzi J.A.S. Effect of isoquinoline alkaloids from two Hippeastrum species on in vitro acetylcholinesterase activity. Phytomedicine 2010, 17:698-701.
17. Pardridge W.M. Blood-brain barrier delivery. Drug Discovery Today 2007, 12:54-61.
18. Pedersen M.E., Szewczyk B., Stachowicz K., Wieronska J., Andersen J., Stafford G.I., van Staden J., Pilc A., Jäger A.K. Effects of South African traditional medicine in animal models for depression. Journal of Ethnopharmacology 2008, 119:542-548.
19. 3H] citalopram binding proteins. European Journal of Pharmacology 1990, 189:129-134.
20. Polli J.W., Wring S.A., Humphreys J.E., Huang L., Morgan J.B., Webster L.O., Serabjit-Singh C.S. Rational use of in vitro P-glycoprotein assays in drug discovery. The Journal of Pharmacology and Experimental Therapeutics 2001, 299:620-628.
21. Sandager M., Nielsen N.D., Stafford G.I., Van Staden J., Jäger A.K. Alkaloids from Boophane disticha with affinity to the serotonin transporter in rat brain. Journal of Ethnopharmacology 2005, 98:367-370.
22. Sobiecki J.F. A preliminary inventory of plants used for psychoactive purposes in southern African healing traditions. Transactions of the Royal Society of South Africa 2002, 57:1-24.
23. Stafford G.I., Pedersen M.E., Van Staden J., Jäger A.K. Review on plants with CNS-effects used in traditional South African medicine against mental diseases. Journal of Ethnopharmacology 2008, 119:513-537.
24. Stahl S.M. Mechanism of action of serotonin selective reuptake inhibitors: serotonin receptors and pathways mediate therapeutic effects and side effects. Journal of Affective Disorders 1998, 51:215-235.
25. Wildman W.C., Kaufman C.J. Alkaloids of the Amaryllidaceae. III. Isolation of five new alkaloids from Haemanthus Species. Journal of the American Chemical Society 1955, 77:1248-1252.