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Planta Med 2003; 69(4): 350-355
DOI: 10.1055/s-2003-38883
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Antimicrobial Alkaloids from the Roots of Polyalthia longifolia var. pendula

Shaheen Faizi1 , Rashid Ali Khan1 , Soobia Azher2 , Shakeel Ahmed Khan2 , Saima Tauseef2 , Aqeel Ahmad2
  • 1H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi, Pakistan
  • 2Department of Microbiology, University of Karachi, Karachi, Pakistan
Further Information

Publication History

Received: July 18, 2002

Accepted: December 22, 2002

Publication Date:
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
    CrossrefPubMedGoogle Scholar
  • 2 Hasan C M, Hossain M DA, Rashid M A, Connolly J D. Constituents of Polyalthia longifolia var. pendula .  Fitoterapia. 1994;  65 283-4
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    Article in Thieme ConnectPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 10 Bentley K W. β-Phenylethylamines and the isoquinoline alkaloids.  Nat Prod Rep. 1997;  14 387-411
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    Google Scholar
  • 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
    Google Scholar
  • 16 Zhang J -S, Men-Olivier L L, Massiot G. Isoquinoline alkaloids from Acangelisia gusanlung .  Phytochemistry. 1995;  39 439-42
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    Google Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 20 Achenbach H, Schwinn A. Aporphinoid alkaloids and terpenoids from Piptostigma fugax .  Phytochemistry. 1995;  38 1037-48
    CrossrefPubMedGoogle Scholar

Prof. Dr. Shaheen Faizi

H.E.J. Research Institute of Chemistry

International Center for Chemical Sciences

University of Karachi

Karachi-75270

Pakistan

Email: shaheen@khi.comsats.net.pk

Fax: +92+21-9243190-91