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Patterns of phenolic compounds in leafy galls of tobacco (1997)

Vereecke, Danny ; Messens, Eric ; Klarskov, Klaus ; [et al.]

Springer

Planta 201 (1997), S. 342-348

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ISSN: 1432-2048

Keywords: Key words: Defense response (plants) ; Leafy galls ; 7-Methyl esculin ; Nicotiana ; Rhodococcus

Source: Springer Online Journal Archives 1860-2000

Topics: Biology

Notes: Abstract. The chemical composition of ethanolic and aqueous extracts from leafy galls produced after infection of Nicotiana tabacum L. plants with Rhodococcus fascians was drastically changed compared to uninfected controls. Chlorogenic acid was abundant both in uninfected and infected plants, but caffeic acid and another cinnamoyl analogue were new in leafy galls. The most pronounced product induced in leafy galls was identified as 7-O-methyl-6-O-β-d-glucopyranosyl coumarin (7-methyl esculin). This is the first report of the presence of this coumarin derivative in tobacco. Interestingly, 7-methyl esculin did not accumulate in the presence of avirulent R. fascians strains nor was it found in leafy galls on other plant species. However, it did appear in crown galls induced by Agrobacterium tumefaciens on tobacco plants. Intriguingly, none of the phenolics known to accumulate in Solanaceae under pathogen attack were found in leafy galls. 7-Methyl esculin barely affected growth of R. fascians nor was it catabolized. Microscopical analysis showed that autofluorescent compounds were located mainly in the abundant meristematic regions of the leafy galls. We postulate that 7-methyl esculin might locally influence plant cell division.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/s004250050076

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Paper (German National Licenses)

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Synthesis and Biological Evaluation of 2-(2-Deoxy-β-D-ribofuranosyl)pyridine-4-carboxamideDedicated to Prof. Frank Alderweireldt on the occasion of his 61st birthday (1992)

Joos, Pieter E. ; Esmans, Eddy L. ; Dommisse, Roger A. ; [et al.]

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 75 (1992), S. 1613-1620

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: A new protected 2-deoxy-D-ribose derivative, 5-O-[(tert-butyl)diphenylsilyl]-2-deoxy-3,4-O- isopropylidene-aldehydo-D-ribose (5), was synthesized starting from 2-deoxy-D-ribose. This compound was coupled with 2-lithio-4-(4,5-dihydro-4,4-dimethyloxazol-2-yl)pyridine giving a D/L-glycero-mixture 7 of 5-O-[(tert-butyl)diphenylsilyl]-2-deoxy-1-C-[4-(4,5 -dihydro-4,4-dimethyloxazol-2-yl)pyridin-2-yl]-3,4-O-isopropylidene- D-erythro-pentitol. The mixture 7 was 1-O-mesylated with methanesulfonyl chloride and subsequently treated with CF3COOH/H2O and ammonia to afford the α/β-D-anomers 10 of 2-(2-deoxy-D-ribofuranosyl)pyridine-4-carboxamide. Both anomers were purified and separated by HPLC and identified by NMR and DCI-MS. Anomer β-D-10 was evaluated against a series of tumor-cell lines and a variety of viral strains. No antitumor or antiviral activity was observed.

Additional Material: 4 Tab.