Antimicrobial alkaloids

A general scheme for the bloassay directed Isolation and characterization of antimicrobial agents from plants Is presented and discussed. The utility of the procedure Is demonstrated by the characterization of two antimicrobial alkaloids from the tulip tree, Llrlodendron tullplfera L. The generalization of the approach to the study of allelopathic agents In plants Is suggested. 

Isolation of Antimicrobial Alkaloids from Tertiary Non-phenolic Base Fraction - A 2 g portion of the crude nonphenolic base fraction was dissolved in chloroform and chromatographed over 200 g of aluminum oxide (Woelm, neutral, grade III). The solvents used were 300 ml of chloroform, 500 ml of 1Z methanol in chloroform, 300 ml of 2Z metha-... 

Charan RD, Schlingmann G Janso J, Beman V, Feng X, Carter GT. (2004) Diazepinomicin, anew antimicrobial alkaloid from amaimeMicromonospora sp. J Nat Prod 67 1431-1433. 

Osterhage C etal., Ascosafrpyrrolidinone A, an antimicrobial alkaloid, from the obligate marine iungns Ascochyta salicorniae, J Org Chem 65 6412—6417, 2000. 

Hufford, C. D., Funderburk, M. J., Morgan, J. M. and Robertson, L. W. 1975. Two antimicrobial alkaloids from heartwood of Liriodendron tulipifera. Journal of Pharmaceutical Science, 64 789-792. 

Odebiyi, O. O. and Sofowora, E. A. 1979. Antimicrobial alkaloids from a Nigerian chewing stick (Fagara zanthoxyloides). Planta Medica, 36 204-207. 

Ross, S. A., Megalla, S. E., Bishay, D. W. and Awad, A. H. 1980. Studies for determining antibiotic substances in some Egyptian plants. Part II. Antimicrobial alkaloids from seeds of Peganum harmala. L. Fitoterapia, 6 309-312. 

An antimicrobial alkaloid that was isolated from roots of Ruta graveolens and from callus tissue cultures proved to be rutacridone epoxide (31).17 The structure was determined by 2H and 13C n.m.r. and by mass spectroscopy, although the configurations at C-2 and C-18 are not known. The epoxide, rather than rutacridone (37), is a major root alkaloid clearly, the plant is chemically different from that studied previously, but the reason for the variation is unknown. 

Several different tissue types - epidermis, endodermis, laticifers, idioblasts, pericycle, and cortex — have now been implicated in the biosynthesis and/or accumulation of various alkaloids in plants. Recently, we have localized berberine in the endodermis of Thalictrum flavum roots at the onset of secondary growth.150 Rather than being sloughed off, the endodermis was found to undergo extensive anticlinal division leading to an expanding cellular cylinder that ultimately displaced all external tissues. Endodermal-specific berberine accumulation continued throughout root development, but was extended to include 3 to 4 layers of smaller pericycle cells in the oldest roots near the base of the stem. The cell type-specific accumulation of an antimicrobial alkaloid and the unusual development of the endodermis and pericycle in T. flavum roots are consistent with the putative role of berberine in plant defense. 

FACCHINI, P.J., JOHNSON, A.G., POUPART. J, DE LUCA, V., Uncoupled defense gene expression and antimicrobial alkaloid accumulation in elicited opium poppy cell cultures. Plant Physiol., 1996, 111, 687-697. 

The coupling of 3-imidazolostannane then cychzation reahzed the synthesis of analogs of antimicrobial alkaloid eudistomin U (Scheme 12.98) [200]. 

Although the endemic species Broussonetia zeylanica (Thw.) has no claims of medicinal applications, when screened, some of its extracts exhibited significant antimicrobial activity against three common pathogenic organisms, Candida albicans, Escherichia coli, and Staphylococcus aureus (15). Bioactivity-guided fractionation led to the isolation of the major antimicrobial alkaloid, 8-hydroxyquinoline-4-carbaldehyde (1), active against C. albicans and S. aureus (17,18). 8-Hydroxyquinoline (oxine) and its derivatives are known to have an array of antimicrobial properties, and a number... 

Keramamine-A and -B, Novel Antimicrobial Alkaloids from the Marine Sponge Pellina sp. Nakamura, H. Shongzhi, D. Kobayashi J. Ohizumi, Y., Tomatake,... 

Faizi S, Khan RA, Azher S, Khan SA, Tauseef S, Ahmad A. New antimicrobial alkaloids from the roots of Polyalthialongifolia var. pendula. Planta Med 2003 69 350-5. 

Koolen HHF, Soares ER, da Silva FMA, de Almeida RA, de Souza ADL, de Medeiros LS, et al. An antimicrobial alkaloid and other metabolites produced by Penicillium sp, an endophytic fungus isolated from Mauritia flexuosa L. f. Quim Nova 2012 35(4) 771. ... 

Mariee NK, KhaUl AA, Nasser AA, Al-Hitti MM, Ah WM. Isolation of the antimicrobial alkaloid stemmadenine from Iraqi Rhazya stricta. J Nat Prod 1988 51 186-7. 

Navarro V, Delgado G (1999) Two antimicrobial alkaloids from Bocconia arborea. J Ethnopharmacol 66 223-226... 

Nakamura H, Deng S, Kobayashi J, Ohizumi Y, Tomotake Y, Matsuzaki T, Hirata Y. Karamamine-A and -B, novel antimicrobial alkaloids from the okinawan marine sponge pellina sp. Tetrahedron Lett. 1987 28(6) 621-624. 

Sansores-Peraza P, Rosado-Vallado M, Brito-Loeza W, Mena-Rejon GJ, Quijano L. Cassine, an antimicrobial alkaloid Irom Senna racemosa. Fitoterapia 2000 71 690 92. 

Nakamura, H., Deng, S., Kobayashi, J., Ohizumi, Y, Tomotake, Y, Matsuzaki, T, and Hirata, Y. (1987b) Keramamines A-B, antimicrobial alkaloids from the Okinawan marine sponge Pellina sp. Tetrahedron Lett., 28, 621-624. 

---