Identification of carotenoids in Erwinia herbicola and in a transformed Escherichia coli strain

Sandmann, Gerhard; Woods, Wendy S.; Tuveson, R. W.

doi:10.1111/j.1574-6968.1990.tb03801.x

Cited by 53 publications

(20 citation statements)

References 17 publications

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“…Polar organic solvents such as acetone and methanol have been extensively used for the extraction of carotenoids from bacteria (2,3,14,16,24,27). In the present investigation, two extractions with methanol liberated all the pigment from 7916 JAGANNADHAM ET AL.…”

Section: Discussionmentioning

confidence: 77%

“…HPLC has been used in the past for the purification of carotenoids from bacteria by employing normal-phase chromatography (7,14,16,24,27). However, since normal-phase chromatography is more variable (7) than reverse-phase chromatography, the latter method has now become more popular (20)(21)(22) and has been used in conjunction with a photodiode array detector.…”

Section: Discussionmentioning

confidence: 99%

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The major carotenoid pigment of a psychrotrophic Micrococcus roseus strain: purification, structure, and interaction with synthetic membranes

1991

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The major carotenoid pigment of a psychrotrophic Micrococcus roseus strain was purified to homogeneity from methanol extracts of dried cells by reverse-phase liquid chromatography and was designated P-3. On the basis of the UV-visible, infrared, mass, and 'H nuclear magnetic resonance spectra of P-3, it was identified as bisdehydro-,-carotene-2-carboxylic acid. The pigment interacted with synthetic membranes of phosphatidylcholine and dimyristoyl phosphatidylcholine and stabilized the membranes. These results also indicate that P-3 is different from canthaxanthin, the major carotenoid pigment from a mesophilic M. roseus strain.Carotenoid pigments are present in a wide variety of bacteria, algae, fungi, and plants (1,23 (16,17). Cells were pelleted by centrifugation at 1,000 x g for 10 min, washed free of medium with distilled water, and freeze-dried to a powder. Methanol (100 ml) was added to about 1 g of freeze-dried cells, and the mixture was vortexed until the methanol layer turned red. The entire suspension of cells was centrifuged (5,000 x g for 5 min), and the methanol layer containing the crude pigment was recovered. The pale pink 7911 JOURNAL

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Section: Discussionmentioning

confidence: 77%

Section: Discussionmentioning

confidence: 99%

The major carotenoid pigment of a psychrotrophic Micrococcus roseus strain: purification, structure, and interaction with synthetic membranes

1991

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“…The all-trans geometrical isomer of ␤-carotene was the major product ( Fig. 4B, peak 1) and, as is typically observed with ␤-carotene-producing E. coli (13,14,54), two cis geometrical isomers (possibly the 9-cis and 15-cis; 54) also accumulated, becoming more prevalent in older cultures.…”

Section: This Work Phpketoskmentioning

confidence: 92%

Carotenoid Biosynthesis in the Primitive Red Alga Cyanidioschyzon merolae

2007

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Cyanidioschyzon merolae is considered to be one of the most primitive of eukaryotic photosynthetic organisms. To obtain insights into the origin and evolution of the pathway of carotenoid biosynthesis in eukaryotic plants, the carotenoid content of C. merolae was ascertained, genes encoding enzymes of carotenoid biosynthesis in this unicellular red alga were identified, and the activities of two candidate pathway enzymes of particular interest, lycopene cyclase and ␤-carotene hydroxylase, were examined. C. merolae contains perhaps the simplest assortment of chlorophylls and carotenoids found in any eukaryotic photosynthetic organism: chlorophyll a, ␤-carotene, and zeaxanthin. Carotenoids with -rings (e.g., lutein), found in many other red algae and in green algae and land plants, were not detected, and the lycopene cyclase of C. merolae quite specifically produced only ␤-ringed carotenoids when provided with lycopene as the substrate in Escherichia coli. Lycopene ␤-ring cyclases from several bacteria, cyanobacteria, and land plants also proved to be high-fidelity enzymes, whereas the structurally related -ring cyclases from several plant species were found to be less specific, yielding products with ␤-rings as well as -rings. C. merolae lacks orthologs of genes that encode the two types of ␤-carotene hydroxylase found in land plants, one a nonheme diiron oxygenase and the other a cytochrome P450. A C. merolae chloroplast gene specifies a polypeptide similar to members of a third class of ␤-carotene hydroxylases, common in cyanobacteria, but this gene did not produce an active enzyme when expressed in E. coli. The identity of the C. merolae ␤-carotene hydroxylase therefore remains uncertain.The unicellular red alga Cyanidioschyzon merolae, a resident of acidic hot springs, is considered to be one of the most primitive of photosynthetic eukaryotes (44,57,65). As such, the photosynthetic apparatus in this alga may provide the closest approximation to that of the prokaryotic ancestor of the modern-day chloroplast. We are especially interested in the ancestry and evolution of enzymes of the pathway that provides for the synthesis of the carotenoids, a family of isoprenoid pigments that are integral and essential constituents of the photosynthetic apparatus in all oxygenic photoautotrophs. In this work, we exploit the recent availability of the nuclear (39), mitochondrial (47), and plastid (46) genome sequences of C. merolae to address the origin of carotenoid pathway genes in this alga.The pathways of carotenoid biosynthesis in eukaryotic plants and in prokaryotic cyanobacteria, the latter of which are considered to be modern-day descendants of the ancestral plastid progenitor (40), are very much alike in their early stages. Reactions in plant chloroplasts that lead from the C 5 isoprenoid precursors isopentenyl diphosphate and dimethylallyl diphosphate to the linear C 40 carotenoid intermediate lycopene are catalyzed by enzymes similar in sequence to their cyanobacterial counterparts (53). Plant and cyanobacterial c...

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“…First, there has clearly been significantly more research dedicated to the production of carotenoid compounds. This is due in part to the earlier sequence availability of such pathways, which then spurred the first heterologous attempts (29,43,48,56,59). Since the first publications on heterologous production, the majority of the remaining studies have been dedicated to metabolic engineering and production optimization.…”

Section: Complete Isoprenoid Biosynthesis and Heterologous Host Biasmentioning

confidence: 99%

Toward Biosynthetic Design and Implementation of Escherichia coli-Derived Paclitaxel and Other Heterologous Polyisoprene Compounds

Jiang

Stephanopoulos

Pfeifer

2012

Appl Environ Microbiol

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bEscherichia coli offers unparalleled engineering capacity in the context of heterologous natural product biosynthesis. However, as with other heterologous hosts, cellular metabolism must be designed or redesigned to support final compound formation. This task is at once complicated and aided by the fact that the cell does not natively produce an abundance of natural products. As a result, the metabolic engineer avoids complicated interactions with native pathways closely associated with the outcome of interest, but this convenience is tempered by the need to implement the required metabolism to allow functional biosynthesis. This review focuses on engineering E. coli for the purpose of polyisoprene formation, as it is related to isoprenoid compounds currently being pursued through a heterologous approach. In particular, the review features the compound paclitaxel and early efforts to design and overproduce intermediates through E. coli. Isoprenoids are an important class of natural products that have been converted to several therapeutic medicines (2,41,42). However, this process can be complicated by the need to harness or reconstruct native biosynthesis. As an example, the well-known isoprenoid natural product paclitaxel is natively produced by the Pacific yew tree (Taxus brevifolia), yet utilizing production from the native host proved both uneconomical and environmentally destructive (5,17,25). An economical total chemical-synthetic route to the compound is challenging due to the molecule's complex final architecture. This common scenario has driven alternative approaches toward the viable production of this and other therapeutically relevant natural products. One such approach is the use of heterologous biosynthesis, in which the genetic content responsible for a given natural compound is transplanted from the native organism to a surrogate host for the purpose of leveraging the new host's innate biological and engineering capabilities. This review focuses on the heterologous biosynthesis approach, using the compound paclitaxel as a primary example. More specifically, emphasis is placed on the logic and initial steps guiding heterologous biosynthesis, including the choice of host organism, the provision of required intracellular substrates, and the initiation of polyisoprene formation. For more comprehensive or alternative discussions of isoprenoid biosynthesis, readers are directed to several additional review articles (1,11,21,30,31,33,40,46,67).Isoprenoids are often associated with plant natural products, but they are also produced by microorganisms (19,58). The compounds play several roles in basic cellular function, including light absorption, electron transport, and protein modification. In addition, they are perhaps better known for their roles in less clearly defined chemical communication scenarios. For example, cellular damage and potential foreign-organism invasion both spur isoprenoid biosynthesis in an attempt to protect plant viability. Such a capacity for isoprenoids to serve as chemical cue...

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Identification of carotenoids in Erwinia herbicola and in a transformed Escherichia coli strain

Cited by 53 publications

References 17 publications

The major carotenoid pigment of a psychrotrophic Micrococcus roseus strain: purification, structure, and interaction with synthetic membranes

The major carotenoid pigment of a psychrotrophic Micrococcus roseus strain: purification, structure, and interaction with synthetic membranes

Carotenoid Biosynthesis in the Primitive Red Alga Cyanidioschyzon merolae

Toward Biosynthetic Design and Implementation of Escherichia coli-Derived Paclitaxel and Other Heterologous Polyisoprene Compounds

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