The search for plant polyprenols.

Świeżewska, Ewa; Sasak, Wlodzimierz; Mańkowski, T; Jankowski, W; Vogtman, Tomasz; Krajewska, Izabella; Hertel, Jozefina; Skoczylas, E; Chojnacki, Tadeusz

doi:10.18388/abp.1994_4713

Cited by 91 publications

(51 citation statements)

References 26 publications

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“…In E. ulmoides, polymerization degrees of poly-cis prenols are thus between 15 and 20 mers, and this is similar to those in other organisms (5,13). In contrast, trans forms showed a broad distribution range of 13 to 37 mers, or more.…”

supporting

confidence: 78%

“…In 1956, solanesol was first isolated from tobacco as a novel unsatu-rated alcohol, and the geometry of all of the double bonds was elucidated to be trans (4). Many studies have been accumulated on the structure and the chain length of polyprenols (5)(6)(7). However, all of the structures of polyprenols so far reported are tri-or di-trans poly-cis except for the case of solanesol.…”

mentioning

confidence: 99%

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The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

Bamba

Fukusaki

Kajivama

et al. 2001

Lipids

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The chain length and geometric isomerism of polyprenols from Eucommia ulmoides Oliver were analyzed using supercritical fluid chromatography. After intensive effort to establish separation conditions for geometric isomers, a phenyl-bonded silica gel-packed column was found that cleanly separated poly-trans and -cis prenols. The presence of long-chain poly-trans prenols (>9 mers) was confirmed for the first time in plants. Trans isomers were found in the leaf, seed coat, and root, but not in the bark and seed. Poly-trans prenols in this plant may act as intermediates for trans-polyisoprene biosynthesis.

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supporting

confidence: 78%

mentioning

confidence: 99%

The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

Bamba

Fukusaki

Kajivama

et al. 2001

Lipids

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“…Lipid I and Lipid II were produced following a semisynthetic method (20) from 11-P and 11-PP. The latter two precursors were obtained from phosphorylation of undecaprenol isolated from Laurus nobilis according to ref 23. Synthetic dioleoyl phosphatidylcholine (DOPC) and dioleoyl phosphatidylglycerol (DOPG) were purchased from Avanti Polar Lipids at Ͼ98% purity and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Targeting extracellular pyrophosphates underpins the high selectivity of nisin

Bonev

Breukink²,

Świeżewska

et al. 2004

FASEB j.

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The spread of infectious diseases and the increase in antibiotic resistance represent a lifethreatening global development that calls for new approaches to control microorganisms. Of all potential targets, the essential and unique pathway of bacterial cell wall synthesis, targeted by the first known antibiotic penicillin, remains a perfect candidate for the development of new antibiotics. Here we show that the lantibiotic nisin exercises its antibacterial action by targeting peptidoglycan intermediates' extracellular pyrophosphate, unique to bacterial cell wall precursors. We show that nisin sequesters cell wall precursors found in the outer leaflet of bacterial plasma membranes, Lipid II and undecaprenyl pyrophosphate, into stable complexes. We propose a model of antibacterial action for nisin in which the terminal amino group of Ile1 targets the pyrophosphate groups of the bacterial cell wall precursors, where it docks via a hydrogen bond. The pyrophosphate moiety, a highly conserved chemical group different from the L-Lys-D-Ala-D-Ala docking motif for vancomycin, has no biochemical analogs with comparable properties and is unlikely to be susceptible to bacterial adaptations akin to those responsible for resistance to penicillins and vancomycin.-Bonev, B. B., Breukink, E., Swiezewska, E., de Kruijff, B., Watts, A. Targeting extracellular pyrophosphates underpins the high selectivity of nisin. FASEB

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“…Takegawa, Kururay Co ., Okayama, Japan . a-Unsaturated polyprenols, used as standards, were prepared from Sorbus suecica and Pinus silvestris as described previously (Swiezewska et al ., 1992(Swiezewska et al ., , 1994 . On TLC in different solvent systems, all polyprenols and phosphorylated derivatives gave single spots .…”

Section: Methodsmentioning

confidence: 99%

Distribution of Branch Point Prenyltransferases in Regions of Bovine Brain

Runquist

Parmryd

Thelin

et al. 1995

Journal of Neurochemistry

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Bovine brains contain large amounts of isoprenoid compounds and the enzymes involved in their biosynthesis were investigated. Ten different regions were dissected from fresh bovine brains and, in addition, fractions from cerebellum, spinal cord, and hypophysis were obtained. The cholesterol concentration was found to be ∼8 mg/g in the cortex regions and three times higher in the pons, medulla oblongata, and white matter. Dolichol concentration varied between 8 and 40 µg/g in the different tissues, and ubiquinone was found at a lower level, which varied between 3 and 25 µg/g. Farnesyl‐pyrophosphate synthase activity in cytosolic fractions from various regions exhibited only a twofold variation, whereas geranylgeranyl pyrophosphate synthase displayed larger differences, being particularly rich in the pons, medulla oblongata, white matter, and spinal cord. Squalene synthase activity was lowest in the thalamus and threefold higher in the pons. Determination of specific activity based on cholesterol content revealed that enzyme activities in various regions are not related to the actual lipid amount present. Both cis‐ and trans‐prenyltransferases exhibited similarities in their regional distribution showing up to 20‐fold differences in activity. Thus, it appears that the mevalonate pathway lipids and the various branch point enzymes involved in their syntheses vary greatly in different brain regions and are subjected to separate regulation.

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The search for plant polyprenols.

Cited by 91 publications

References 26 publications

The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

The occurrence of geometric polyprenol isomers in the rubber‐producing plant, Eucommia ulmoides oliver

Targeting extracellular pyrophosphates underpins the high selectivity of nisin

Distribution of Branch Point Prenyltransferases in Regions of Bovine Brain

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