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Studies on the Corrinoids and Porphyrins in Streptomycetes

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Studies on the Corrinoids and Porphyrins in Streptomycetes [Agr. Biol. Chem., Vol. 32, No. 1, p. 7-11, 1968] Studies on the Corrinoids and Porphyrins in Streptolnycetes Part II. Factors Influencing the Accumulation of Coproporphyrin III in the Culture Filtrate of Streptomycesoliz aceus 605 By KazuyoshiSATO, Shoichi SHIMIZU and Saburo FUKUI* Laboratoryof Industrial Biochemistry, Department of Industrial Chemistry, Facultyof Engineering,Kyoto University, Kyoto, Japan ReceivedJune 9, 1967 In a medium containing glycerol as u carbon source, Streptomyces olivaceus 605 ac- cumulated under mild aeration a large amount of porphyrin in the culture filtrate. Identity of methyl ester of the porphrin with coproporphyrin III methyl ester was confirmed by UV-, IR- and NMR- spectroscopy. Under the cultural conditions favarable for production of corrinoid, the accumulation of coproporphyrin III markedly decreased. The accumulation of porphyrins in the corrinoid are known to be formed via the culture has been noted in various organisms same route at the early stage of their biosyn such as Rhodopseudomonas spheroides,l) Micrococcus thetic pathways. Furthermore, the structure lysodeikticus,2) Tetrahymena vorax,3) Staphylococ of corrin nucleus is analogus to that of porphrin. cus epidermidis,4) Saccharomyces eerevisiae5) and It is thus interesting to investigate the type Bacillus cereus6) and so on. of the porphyrin accumulated in relation to Concerning Streptomycetes, Musilek7) also the corrin biosynthesis. In this paper we will observed the accumulation of porphyrin in the report about the identity of the porphyrin culture broth of S. griseus and S. fradiae but with coproporpyrin III and the cultural condi did not determine the precise structure. tions affecting its accumulation. We found that S. olivaceus 605, accumulated a great amount of a porphyrin in the culture MATERIALS AND METHODS filtrate under special conditions. The largest Microorganisms. S. olivaceus 605 supplied from Tokyo Research Laboratory of Kyowa Hakko Kogyo production occurred in the case of a medium Co. was mainly used. For comparison S. olivaceus containing glycerol as a carbon source and 603 and S. olivaceus TAM 0012 were also used. low oxygen tension, whereas the accumula Cultivation medium. The production of corrinoid tion was markedly lowered when glucose was and the accumulation of porphyrin compounds in the used as a carbon source. Both porphyrin and culture broth were studied using media whose carbon sources were glucose, glucose-lactose, and glycerol, respectively. The compositions of these media are * Correspondence should be sent to the author. given in Table I. Cultural conditions are described 1) J. Lascelles, Biochem. J. 62, 78 (1956). 2) P. M. Townsley and J. B. Neilands, J. Biol. in the preceding papers) Chem., 224, 695 (1957). Extraction and assay method of porphyrins 3) J. Lascelles, Biochem. J., 66, 65 (1957). 4) R. E. Heady, N. J. Jacobs and R. H. Deibel, produced in the culture filtrate of S. olivaceus 605 Nature, 203, 1286 (1964). As mentioned in the preceding paper,°) 10 ml of 5) H. Chantrenne and C. Courtois, Biochim. Biophys. Acta, 14, 397 (1954). 6) P. Schaeffer, ibid., 9, 261 (1952). 8) K. Sato, S. Shimizu and S. Fukui, Agr. Biol. 7) V. Musilek, Science, 137, 674 (1962). Chem., 32, 1 (1968). 8 Kazuyoshi SATO, Shoichi SHIMIZU and Saburo FUKUI TABLE I. COMPOSITIONS OF THE MEDIA USED FOR obtained was esterified with HCl-methanol (HCl Streptomyces olivaceus 605 cone., 15 (w/w)o) for 25 hr at 20°C and the re sulting methyl ester was purified by alumina column chromatography using chloroform-petroleum ether (1:3) as a developer. The porphyrin methyl ester was eluted only in single band, which was further purified three times on the alumina column. The eluate was evaporated to dryness under reduced pres- sure at 35 to 40°C and crystallized from chloroform and methanol. The yield was about 28 mg from the 5 liter culture. All the solvents used were freshly distilled before use, and the alumina was purchased from F. Merck A. G., Darmstadt, Germany. Detection of spectra of cytochrome contained in intact cells Cytochrome pigments in intact cells of S. olivaceus 605 harvested from the shaking culture were detected with Shimazu MPS-50 Type Multi-purpose Spectro photometer according to the opal-glass method of Shibata.10) The cells used were washed once with 0.1 N phosphate buffer (pH 7.0) and the measurement the culture was taken into a graduated centrifugal was carried out in a concentration of 50 to 100 mg tube and centrifuged at 3000 x g for 10 min to dry cells per ml. measure the volume of sedimented cells. The growth of the microorganism was expressed by the cell Measurement of infrared- and nuclear magnetic volume. Thirty ml of a mixture of acetic acid and resonance spectra IR spectra were measured with a Hitachi Grating ethylacetate (1:3 v/v) was added to 25 ml of the Infrared Spectrophotometer DS-402G. NMR spectra supernatant in order to extract the porphyrins. Re sulting precipitates were filtered off and throughly of the porphrin methyl ester dissolved in CDCl3 were obtained using Varian NMR Spectrophotometer, washed with the same solvent mixture. The filtrate Model A 60. and washings were combined, then washed with di- stilled water to eliminate the acetic acid. The RESULTS porphyrins contained in the ethylacetate solution Comparison of the amounts of porphyrins ac- were completely extracted with 5% HCI. The amount cumulated in various media of the porphyrin in the HCI extract, which was ob- Fig. 1 shows the amounts of porphyrins ac- served to be coproporphyrin Ill as shown later, was assayed by measuring the peak of Soret band with cumulated in the culture filtrate in the glucose-, Shimazu QB 50 Spectrophotometer. For calculation glucose-lactose- and glycerol-medium, respec of coproporphyrin content, the extinction coefficient tively. When glycerol was used as a carbon given by Falk9) and the following formula were source, more than 10 mg/l of porphyrins was used. accumulated in the culture filtrate. In this 2•~OD401mƒÊ-(OD430mƒÊ+OD350mƒÊ)•~837•~ƒÒ/V case, degrees of the maximal growth in the =Coproporphyrin (ƒÊg/l) glucose-lactose medium and in the glucose v=volume of HCl-extract (ml). medium were four-fifths and three-fifths of V=volume of crude solution (ml). that in the glycerol medium, respectively . The accumulation phenomenon of such a large Esterification of porphyrin. The crude porphyrin quantity of porphyrins is first observed in Streptomycetes and there are only few examples 9) J. E. Falk, J. Chromato., 5, 277 (1961); "Por phyrins and Metalloporphyrins," Elsevier Publishing Co., Amsterdam (1964). 10) K. Shibata, J. Biochem., 45, 599 (1958). Studies on the Corrinoids and Porphyrins in Streptomyeetes. Part II 9 FIG. 1. Comparison of the Amount of Porphyrin FIG. 2. Effect of Metal Ion Added to the Glycerol Produced in Different Media by S. olivaceus 605. Medium upon the Growth of S. olivaceus 605. CoCl2 and FeSO4 were added to glycerol-medium The amount of salts added was 2 mg/200 ml in a concentration of 10 mg/1, respectively. Cultiva culture. The cultural conditions were same as tion was carried out with shaking (220 rpm) at those of Fig. 1. 30°C using a 500-ml shaking flask containing 200 ml medium. in other microorganisms. In contrast, the amounts of porphyrins ac- cumulated were one-tenth in the glucose- lactose medium and one-fiftieth in the glucose- medium, respectively. Furthermore, the effect of addition of metal ions was investigated and the detailed results will be mentioned in a succeeding paper. When Co2+ was added to the glycerol medium, there was little difference in the total amounts FIG. 3. Effect of Different Levels of Aeration upon the Growth and Porphyrin Accumulation. of porphyrins. However, free porphyrins de- creased as shown in Fig. 1, and the amount of metalloporphyrins extractable into ethyla Amt. of media in 500 ml flask; 0 300, • 200, cetate was increased. In contrast, when Fe" A 100 ml. was added, the amount of free porphyrin markedly decreased, while the metallopor medium in 50 ml-shaking flask upon the cell phyrin in ethylacetate layer was not detected. growth as well as the accumulation of por The increase of protein-bound heme was ex phyrins. It was observed that the amount pected in this case, but further studies were of porphyrins accumulated was closely relat not performed on this problem. As for the ed to the quantity of oxygen supplied to the effect of metal ions on the growth of S. culture. Less aeration suppressed the growth olivaceus 605, the length of the lag phase was but enhanced the porphyrin accumulation. relatively reduced by adding Co2+, whereas Form of the porphyrins accumulated in the no effect was observed by adding Fe2+ (Fig. 2). culture filtrate. The porphyrins accumulated Influence of aeration. Fig. 3 shows the effect showed the following behaviors on paper of the different levels of the volume of the chromatography and paper electrophoresis. 10 Kazuyoshi SATO, Shoichi SHIMIZU and Saburo FUKUI On a paper chromatogram developed with a mixture of 2,4-lutidine and water (10:7) a spot was predominantly detected by fluorescence at Rf 0.61 which was corresponding to that of coproporphyrin. In some case another spot was faintly detected at Rf 0.04 suggesting the presence of small amounts of uroporphyrin. On paper electrophoresis performed at pH 2.7 the predominant porphyrin moved little to the anode. At pH 8.6 it moved about 1.5 to 2.0 cm to the anode from the origin. These ionophoretic mobilities were analogous to those FIG. 4. Visible Absorption Spectrum of Methyl of coproporphyrins reported by Falk.9) Ester of the Porphyrin Isolated. (in CHCl3) These results supported the possibility that almost all the porphyrin accumulated in the broth belongs to coproporphyrin.
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