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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 8
Morita H, Matsumoto K, Takeya K, Itokawa H.
Azafluoranthene alkaloids from Cissampelos pareira.
Chem Pharm Bull.
1993;
41
1307-1308
MissingFormLabel
- 9
Menachery M D, Cava M P.
Grandirubrine, a new tropoloisoquinoline alkaloid.
Heterocycles.
1980;
14
943-945
MissingFormLabel
- 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
MissingFormLabel
- 11
Menachery M D, Cava M P.
The alkaloids of Telitoxicum peruvianum.
J Nat Prod.
1981;
44
320-323
MissingFormLabel
- 12
Skiles J W, Cava M P.
Subsessiline: structure revision and synthesis.
J Org Chem.
1979;
44
409-412
MissingFormLabel
- 13
Mossmann T.
Rapid colorimetric assay for cellular growth and survival: application to proliferation
and cytotoxicity assays.
J Immunol Methods.
1983;
65
55-63
MissingFormLabel
- 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
MissingFormLabel
- 15
Boger D L, Takahashi K.
Total synthesis of granditropone, grandirubrine, imerubrine, and isoimerubrine.
J Am Chem Soc.
1995;
117
12452-12459
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
- 18
Lee J C, Cha J K.
Total synthesis of tropoloisoquinolines: imerubrine, isoimerubrine, and grandirubrine.
J Am Chem Soc.
2001;
123
3243-3246
MissingFormLabel
- 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
MissingFormLabel
- 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
MissingFormLabel
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