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DOI: 10.1055/s-2003-38883
© Georg Thieme Verlag Stuttgart · New York
New Antimicrobial Alkaloids from the Roots of Polyalthia longifolia var. pendula
Publikationsverlauf
Received: July 18, 2002
Accepted: December 22, 2002
Publikationsdatum:
23. April 2003 (online)
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Abstract
Bioassay-guided isolation studies on the root extract of Polyalthia longifolia var. pendula possessing significant antibacterial activity led to the isolation of three new alkaloids pendulamine A (1), pendulamine B (2) and penduline (3) along with stigmasterol 3-O-β-D-glucoside, allantoin, the known diterpenoid kolavenic acid, and the azafluorene alkaloid isoursuline. The structures of these compounds have been elucidated with the help of spectroscopic studies including 2D NMR experiments. Compounds 1 and 2, which are the only protoberberine alkaloids having a monosubstituted A ring with a hydroxy group at C-3, were found to be the active antibacterial principles of the roots. Their MIC values ranged between 0.02 - 20 μg against the tested bacteria.
Key words
Polyalthia longifolia var. pendula - Annonaceae - roots - alkaloids - 8-oxoprotoberberine - azafluorenones - antibacterial activity
References
- 1 Chen C -Y, Chang F -R, Shih Y -C, Hsieh T -J, Chia Y -C, Tseng H -Y. et al . Cytotoxic constituents of Polyalthia longifolia var. pendula . J Nat Prod. 2000; 63 1475-8, and references cited therein
- 2 Hasan C M, Hossain M DA, Rashid M A, Connolly J D. Constituents of Polyalthia longifolia var. pendula . Fitoterapia. 1994; 65 283-4
- 3 Laprévote O, Roblot F, Hocquemiller R, Cavé A. Alcaloides des annonocées, 87. Azafluorénones de l’ Unonopsis spectabilis . J Nat Prod. 1988; 51 555-61
-
4 Dictionary of Natural P roducts. Vol. 1 Chapman and Hall London; 1994: pp. 168-9, 2277 - 8, 61, 352
- 5 Bauer A W, Kirby W MM, Sherris J C, Turck M. Antibiotic susceptibility testing by a standardized single disc method. Am J Clin Path. 1966; 45 493-6
- 6 Iwasa K, Nanba H, Lee D -U, Kang S -I. Structure-activity relationships of protoberberines having antimicrobial activity. Planta Med. 1998; 64 748-51
- 7 Iwasa K, Lee D -U, Kang S -I, Wiegrebe W. Antimicrobial activity of 8-alkyl- and 8-phenyl-substituted berberines and their 12-bromo derivatives. J Nat Prod. 1998; 61 1150-3
- 8 Hong S W, Kim S H, Jeun J A, Lee S J, Kim S U, Kim J H. Antimicrobial activity of 9-O-acyl- and 9-O-benzoyl-substituted berberrubines. Planta Med. 2000; 66 361-3
- 9 Zhang J -S, Chen Z -L. Two new 8-oxotetrahydroprotoberberine alkaloids, gusanlung A and B, from Acangelisia gusanlung . Planta Med. 1991; 57 457-9
- 10 Bentley K W. β-Phenylethylamines and the isoquinoline alkaloids. Nat Prod Rep. 1997; 14 387-411
- 11 Chen C -Y, Maclean D B. Mass spectra and proton magnetic resonance spectra of some tetrahydroprotoberberine alkaloids. Can J Chem. 1968; 46 2501-6
- 12 Pinho P MM, Pinto M MM, Kijjoa A, Pharadai K, Diaz J G, Herz W. Protoberberine alkaloids from Coscinium fenestratum . Phytochemistry. 1992; 31 1403-7
- 13 Patra A, Montgomery C T, Freyer A J, Guinaudean H, Shamma M, Tantisewie B. , et al . The protoberberine alkaloids of Stephania suberosa . Phytochemistry. 1987; 26 547-9
- 14 Beecher C WW, Kelleher W J. The Biosynthesis of the Protoberberine Alkaloids, 4. Alkaloids: Chemical and Biological Perspectives. In : Pelletier SW, editor John Wiley and Sons Vol. 6 New York; 1988: pp. 297-337
- 15 Cavé A, Leboeuf M, Cassels B K. Alkaloids from Guatteria, 1. The Alkaloids Chemistry and Pharmacology. In: Brossi A, editor Academic Press, Inc. Vol. 35 California; 1989: 1-76
- 16 Zhang J -S, Men-Olivier L L, Massiot G. Isoquinoline alkaloids from Acangelisia gusanlung . Phytochemistry. 1995; 39 439-42
- 17 Arango G J, Cortes D, Cassels B K, Cave A, Merienne C. Azafluorenones from Oxandra cf. Major and biogenetic considerations. Phytochemistry. 1987; 26 2093-8
- 18 Clark A M, Hufford C D. Antifungal Alkaloids, 2. The Alkaloids Chemistry and Pharmacology. In: Cordell GA, editor Academic Press, Inc. Vol. 42 California; 1992: 117-50
- 19 Tadic’ D, Cassels B K, Leboeuf M, Cavé A. Kinabaline and the aporphinoid biogenesis of azaanthracene and azafluorene alkaloids. Phytochemistry. 1987; 26 537-41
- 20 Achenbach H, Schwinn A. Aporphinoid alkaloids and terpenoids from Piptostigma fugax . Phytochemistry. 1995; 38 1037-48
Prof. Dr. Shaheen Faizi
H.E.J. Research Institute of Chemistry
International Center for Chemical Sciences
University of Karachi
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Pakistan
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