Plasmid control of the Pseudomonas aeruginosa and Pseudomonas putida phenotypes and of linalool and p-cymene oxidation

Smet, M J de; Friedman, M B; Gunsalus, I. C.

doi:10.1128/jb.171.9.5155-5161.1989

Cited by 7 publications

(5 citation statements)

References 33 publications

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“…A brushtail possum produced a carboxylic acid by oxidation at the 7-position of 4 and degraded 4 to p-cresol (Southwell et al, 1980). Some species of microorganism degraded 4 by oxidation at the 7-position and 1,2-double bond (Madhyastha and Bhattacharyya, 1968;Wigmore and Ribbons, 1981;Ninnekar and Pujar, 1985;De Smet et al, 1989). Another species of microorganism produced carboxylic acids by oxidation at the 7-or 9-position of 4 (Yamada et al, 1965;Madhyastha and Bhattacharyya, 1968).…”

Section: Resultsmentioning

confidence: 99%

Biotransformation of α-Terpinene in Common Cutworm Larvae (Spodoptera lituraFabricius)

Miyazawa

Wada

Kameoka

1996

J. Agric. Food Chem.

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α-Terpinene was mixed in an artificial diet at a concentration of 10 mg/g of diet, and the diet was fed to the last instar larvae of common cutworm, Spodoptera litura Fabricius. Metabolites were recovered from frass and analyzed spectroscopically. The α-terpinene was transformed mainly to 4-isopropyl-1,3-cyclohexadienoic acid and cumic acid. The allylic methyl group of α-terpinene was preferentially oxidized. The results indicate that the intestinal bacteria probably participated in the metabolism of α-terpinene. The aerobically active intestinal bacteria transformed α-terpinene to 4-isopropyl-1,3-cyclohexadienemethanol, and the anaerobically active intestinal bacteria transformed α-terpinene to p-cymene. Keywords: Common cutworm; Spodoptera litura Fabricius; larvae; biotransformation; α-terpinene; allylic oxidation; 4-isopropyl-1,3-cyclohexadienemethanol; 4-isopropyl-1,3-cyclohexadienoic acid; p-cymene; cumic alcohol; cumic acid; intestinal bacteria

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Section: Resultsmentioning

confidence: 99%

Biotransformation of α-Terpinene in Common Cutworm Larvae (Spodoptera lituraFabricius)

Miyazawa

Wada

Kameoka

1996

J. Agric. Food Chem.

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“…Monoterpenes are generally toxic to microbes, impairing numerous functions of biological membranes ( Knobloch et al 1989 ; Lawton et al 1993 ; Weidenhamer et al 1993 ; Lee et al 1998 ) and are difficult for bacteria to metabolize ( Cantwell et al 1978 ). However, several species of soil bacteria utilize linalool and other monoterpenes as carbon sources, including Pseudomonas fluorescens ( Vandenbergh & Cole 1986), P. citronellolis , P. incognita ( Seubert 1959; Devi & Bhattacharyya 1977; Madyastha et al 1977 ; Renganathan & Madyastha 1983), P. aeruginosa and P. putida ( de Smet et al 1989 ). The capacity to metabolize linalool is conferred by a transposable plasmid with a structural gene encoding a cytochrome P450 hydroxylase.…”

Section: Epilogue: Metabolism Of Linalool By Soil Microbesmentioning

confidence: 99%

“…The capacity to metabolize linalool is conferred by a transposable plasmid with a structural gene encoding a cytochrome P450 hydroxylase. This function adds a second hydroxyl group to carbon 8 or 10 of linalool, after which a series of oxidation steps yields linalool‐8‐carboxylic acid and CO 2 through perillic acid ( de Smet et al 1989 ; Fig. 10).…”

Section: Epilogue: Metabolism Of Linalool By Soil Microbesmentioning

confidence: 99%

“…10). The plasmid‐borne P450 function is substrate specific, such that bacterial strains that metabolize geraniol, nerol or citronellol cannot oxidize linalool, and can be acquired through bacterial conjugation ( de Smet et al 1989 ). These systems have been studied in the context of anthropogenically contaminated soils (e.g.…”

Section: Epilogue: Metabolism Of Linalool By Soil Microbesmentioning

confidence: 99%

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New Perspectives in Pollination Biology: Floral Fragrances. A day in the life of a linalool molecule: Chemical communication in a plant‐pollinator system. Part 1: Linalool biosynthesis in flowering plants

Raguso

Pichersky

1999

Plant Species Biology

198

147

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The monoterpene alcohol, linalool, is present in the ßoral fragrance of diverse plant families and is attractive to a broad spectrum of pollinators, herbivores and parasitoids. Floral emission of linalool has evolved de novo in the fragrant, moth-pollinated annual Clarkia breweri (Gray) Greene (Onagraceae) through a combination of up-regulation and ectopic expression of its biosynthetic enzyme, linalool synthase (LIS), in conjunction with allometric size increases in all ßoral organs. Linalool synthase activity and linalool emissions are 1000-fold lower in a sibling species, C. concinna (Fischer & Meyer) Greene, that is diurnally pollinated. Linalool synthase expression is spatially and temporally regulated during C. breweri ßower development, immediately precedes free linalool emission and is absent from nonßoral tissues. Its activity is highest in the style, but most of the linalool product appears to be converted to the pyranoid and furanoid linalool oxides. The LIS structural gene is a member of the terpene synthase gene family, sharing sequence identity with two discrete classes, represented by limonene synthase (LMS) and copalyl pyrophosphate synthase (CPS). Genetic crosses between C. breweri and C. concinna indicate that strong linalool emission segregates as a dominant mendelian trait, whereas the inheritance of linalool oxide formation is more complex, suggesting epistatic biosynthetic pathway interactions. We discuss areas for future research, including comparative studies of linalool biosynthesis in different plant families, entrainment of linalool emission to nocturnal circadian rhythms and the induction of vegetative linalool as an indirect herbivore defense.

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“…The isolation and maintenance of the fluorescent Pseudomonas strain Dl1OR have been described previously (6,65).…”

Section: Methodsmentioning

confidence: 99%

Cloning and expression of a member of a new cytochrome P-450 family: cytochrome P-450lin (CYP111) from Pseudomonas incognita

1993

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Cytochrome P-4501in catalyzes the 8-methyl hydroxylation of linalool as the first committed step of its utilization by Pseudomonas incognita as the sole carbon source. By using a polymerase chain reaction-based cloning strategy, a 2.1-kb DNA fragment containing the cytochrome P-4501in gene (linC) was isolated. An open reading frame of 406 amino acids has been identified as that of P-4501in on the basis of amino acid sequence data from peptides of the native protein. Heterologous expression of functional holoprotein is exhibited by Escherichia coli transformed with pUC18 containing the subcloned linC gene under constitutive transcriptional control of the lac promoter. The G+C content oflinC was found to be 55% overall and 58% in the third codon position. An optimized amino acid sequence alignment of P-4501in with cytochrome P-450cam shows that the two enzymes have only 25% identity. P-4501in was found to exhibit the expected conservation in the axial cysteine heme ligand-containing peptide and the threonine region postulated to form an 02-binding pocket (T. L. Poulos, B. C. Finzel, and A. J. Howard, J. Mol. Biol. 195:687-700, 1987). The low amino acid sequence identity between P-4501in and all other P-450 sequences has shown that P45O1in is the first member of the CYPIll P-450 gene family.Members of the genus Pseudomonas play a major role in the metabolism of a variety of complex organic molecules, including hydrocarbons, utilizing oxygen as a cosubstrate. Therefore, it is not surprising that members of the equally diverse family of cytochrome P-450 monooxygenases are recognized to participate in chemical transformations leading to their use as biological energy and carbon sources (53, 67). P-450s have been shown to be involved in xenobiotic transformation as well as biosynthesis of secondary metabolites in other prokaryotes as well (39, 53-55, 64, 69). In eukaryotes, oxygen insertion at unactivated carbon centers by cytochrome P-450 is key to numerous essential biosynthetic pathways, including those for steroid hormones and prostoglandins, as well as in detoxification of foreign substances (8,21,68).Cytochrome P-450cam (cam indicates that cytochrome P-450 is specific for camphor), the first Pseudomonas P-450 to be cloned and sequenced (27,66), has long been the prototype for not only the prokaryotic P-450s but also the entire P-450 superfamily, with extensive physical and biochemical characterization dating back to the early 1970s (5,11,57,(71)(72)(73). The availability of a high-resolution tertiary structure for P-450cam, including substrate-free (41), substrate-bound (42), and several inhibitor-bound (43, 44) structures, has paved the way for the use of rational site-directed mutagenesis to further probe the structure-function relationships in P-450cam (for reviews, see references 32, 56, and 61).Pseudomonas which catalyzes the 8-methyl hydroxylation of linalool by utilizing reducing equivalents ultimately derived from NADH (45, 46). The monooxygenase, P-4501in, as well as its redox partner proteins, lin-redox...

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Plasmid control of the Pseudomonas aeruginosa and Pseudomonas putida phenotypes and of linalool and p-cymene oxidation

Cited by 7 publications

References 33 publications

Biotransformation of α-Terpinene in Common Cutworm Larvae (Spodoptera lituraFabricius)

Biotransformation of α-Terpinene in Common Cutworm Larvae (Spodoptera lituraFabricius)

New Perspectives in Pollination Biology: Floral Fragrances. A day in the life of a linalool molecule: Chemical communication in a plant‐pollinator system. Part 1: Linalool biosynthesis in flowering plants

Cloning and expression of a member of a new cytochrome P-450 family: cytochrome P-450lin (CYP111) from Pseudomonas incognita

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