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
Karachi-75270
Pakistan
Email: shaheen@khi.comsats.net.pk
Fax: +92+21-9243190-91