RSS-Feed abonnieren
DOI: 10.1055/s-0031-1280383
© Georg Thieme Verlag KG Stuttgart · New York
Phytochemical Investigation and In Vitro Cytotoxic Evaluation of Alkaloids from Abuta rufescens
Publikationsverlauf
received June 4, 2011
revised October 31, 2011
accepted November 2, 2011
Publikationsdatum:
22. November 2011 (online)
Abstract
A phytochemical investigation of Abuta rufescens was performed to authenticate plant material reported previously and to assess the cytotoxicity of the alkaloids obtained from the plant. Three alkaloids which have not previously been reported from this species, two phenolic (subsessiline, an oxoaporphine, and telitoxine, an azafluoranthene) and one non-phenolic (isoimerubrine, a tropoloisoquinoline), were isolated and identified. These alkaloids, along with others previously isolated from this and another Abuta species (grandirubrine, a tropoloisoquinoline), were evaluated for cytotoxic activity against several human cancer cell lines (HCT-116 colon adenocarcinoma, ACHN renal carcinoma, and A549 lung carcinoma). The tropoloisoquinoline alkaloids (grandirubrine, imerubrine, and isoimerubrine) exhibited the greatest cytotoxicity against the cell lines, especially ACHN and HCT-116 cells. The azafluoranthene alkaloid imeluteine exhibited lesser cytotoxicity, as did one of the oxoaporphine alkaloids.
Key words
tropoloisoquinolines - azafluoranthenes - oxoaporphines - Abuta rufescens/Abuta splendida - Menispermaceae - cytotoxicity
References
- 1 Krukoff B A, Barneby R C. Supplementary notes on American menispermaceae: neotropical triclisieae and anospermaceae. Phytologia. 1978; 39 283-293
- 2 Menachery M D. The alkaloids of South American menispermaceae. In: Pelletier S W, editor Alkaloids: chemical & biological perspectives. Vol. 11 London: Pergamon Press; 1996: 269-302
- 3 Cava M P, Buck K T, Noguchi I, Srinivasan M, Rao M G, DaRocha A I. The alkaloids of Abuta imene and Abuta rufescens. Tetrahedron. 1975; 31 1667-1669
- 4 Saá J M, Lakshmikantham M V, Mitchell M J, Cava M P. Krukovine, a new bisbenzylisoquinoline alkaloid from Abuta splendida Krukoff and Moldenke. J Org Chem. 1976; 41 317-319
- 5 Skiles J W, Saá J M, Cava M P. Splendidine, a new oxoaporphine alkaloid from Abuta rufescens Aublet. Can J Chem. 1979; 57 1642-1646
- 6 Krukoff B A, Moldenke H N. Studies of American Menispermaceae, with special reference to species used in preparation of arrow-poisons. Brittonia. 1938; 3 50-71
- 7 Itokawa H, Matsumoto K, Morita H, Takeya K. Preparation and antileukemic activity of congeners of tropoloisoquinoline alkaloids from Abuta concolor. Heterocycles. 1994; 37 1025-1031
- 8 Morita H, Matsumoto K, Takeya K, Itokawa H. Azafluoranthene alkaloids from Cissampelos pareira. Chem Pharm Bull. 1993; 41 1307-1308
- 9 Menachery M D, Cava M P. Grandirubrine, a new tropoloisoquinoline alkaloid. Heterocycles. 1980; 14 943-945
- 10 Menachery M D, Blake G W, Gourley R C, Freyer A. Telisatin A, telisatin B, and telitoxinone, three new aporphinoids from Telitoxicum peruvianum. J Nat Prod. 1995; 58 1945-1949
- 11 Menachery M D, Cava M P. The alkaloids of Telitoxicum peruvianum. J Nat Prod. 1981; 44 320-323
- 12 Skiles J W, Cava M P. Subsessiline: structure revision and synthesis. J Org Chem. 1979; 44 409-412
- 13 Mossmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983; 65 55-63
- 14 Bane Hastie S, Williams R C, Pruett D, McDonald T L. The binding of isocolchicine to tubulin. J Biol Chem. 1989; 264 6682-6688
- 15 Boger D L, Takahashi K. Total synthesis of granditropone, grandirubrine, imerubrine, and isoimerubrine. J Am Chem Soc. 1995; 117 12452-12459
- 16 Banwell M G, Hamel E, Ireland N K, Mackay M F. Regiocontrolled total syntheses of the tropoloisoquinoline alkaloids imerubrine and grandirubrine. Heterocycles. 1994; 39 205-217
- 17 Banwell M G, Ireland N K. Regiocontrolled total synthesis of imerubrine: the first total synthesis of a tropoloisoquinoline alkaloid. J Chem Soc Chem Commun. 1994; 591-592
- 18 Lee J C, Cha J K. Total synthesis of tropoloisoquinolines: imerubrine, isoimerubrine, and grandirubrine. J Am Chem Soc. 2001; 123 3243-3246
- 19 Chaturvedula V S, Norris A, Miller J S, Ratovoson F, Andriantsiferana R, Rasamison V E, Kingston D G. Cytotoxic diterpenes from Cassipourea madagascariensis from the Madagascar rainforest. J Nat Prod. 2006; 69 287-289
- 20 Swaffar D S, Ireland C M, Barrows L R. A rapid mechanism-based screen to detect potential anti-cancer agents. Anticancer Drugs. 1994; 5 15-23
Prof. Dr. Diane S. Swaffar
College of Pharmacy
Roseman University of Health Sciences
10 920 South River Front Parkway
South Jordan, Utah 84095
USA
Telefon: +1 80 18 78 10 78
Fax: +1 80 13 02 07 68
eMail: dswaffar@roseman.edu