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Carotenoids of Rhizobia

II. The effect of nicotine on the carotenoid pattern of Rhizobium lupini

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Abstract

With increasing concentrations in the growth medium of the cyclization inhibitors nicotine or 2-(4-chlorophenylthio)-triethylamine hydrochloride (CPTA) the previously identified bicyclic carotenoids of Rhizobium lupini (2,3,2′,3′-tetrahydroxy-β,β-caroten-4-one and 2,3,2′,3′-tetrahydroxy-β,β-carotene) were successively replaced by hitherto unknown monocyclic carotenoids. By application of mass and nuclear magnetic resonance spectroscopy 3 carotenoids were identified as 2,3-trans-dihydroxy-β,ψ-caroten-4-one, 2,3-trans-dihydroxy-β,ψ-carotene, and 3-hydroxy-β,ψ-caroten-4-one. A further compound was tentatively established as (2- or 3-)monohydroxy-β,ψ-carotene. It was found that other inhibitors such as diphenylamine or 4-chloro-5-(dimethylamino)-2-α,α,α(trifluoro-m-tolyl)-3-(2H)-pyridazinone (San 6706) did not affect the pigment pattern. The results are discussed in relation to carotenoid biosynthesis in Rhizobium lupini.

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Abbreviations

CPTA:

2-(4-chlorophenylthio)-triethylamine hydrochloride

San 6706:

4-chloro-5-(dimethylamino)-2-α,α,α-(trifluoro-m-tolyl)-3-(2H)-pyridazinone

References

  • Baldas, J., Porter, Q. N., Leftwick, A. P., Holzel, R., Weedon, B. L. C., Szabolcs, J.: Mass spectroscopy of carotenoid ketones. Chem. Commun. 1969, 425–427

  • Britton, G.: Later reactions of carotenoid biosynthesis. Pure Appl. Chem. 47, 223–236 (1976)

    Google Scholar 

  • Britton, G., Singh, R. K., Goodwin, T. W.: Carotenoid biosynthesis in Rhodomicrobium vannielii. Experiments with nicotine and 2-(4-chlorophenylthio)-triethylammonium chloride (CPTA). Biochim. Biophys. Acta 488, 475–483 (1977)

    PubMed  Google Scholar 

  • Coggins, C. W., Henning, G. L., Yokoyama, H.: Lycopene accumulation induced by 2-(4-chlorophenylthio)triethylamine hydrochloride. Science 168, 1589–1590 (1970)

    PubMed  Google Scholar 

  • Davies, B. H.: Carotenoids. In: Chemistry and biochemistry of plant pigments, Vol. 2 (T. W. Goodwin, ed.), pp. 38–165. London-New York-San Francisco: Academic Press 1976

    Google Scholar 

  • Elahi, M., Lee, T. H., Simpson, K. L., Chichester, C. O.: Effect of CPTA and cycocel on the biosynthesis of carotenoids by Phycomyces blakesleeanus mutants. Phytochem. 12, 1633–1639 (1973)

    Google Scholar 

  • Englert, G., Kienzle, F., Noack, K.: 1H-NMR.-, 13C-NMR.-, UV.-und CD.-Daten von synthetischen (3S,3′S)-Astaxanthin, seinen 15-cis-Isomeren und einigen analogen Verbindungen. Helv. Chim. Acta 60, 1209–1219 (1977)

    Google Scholar 

  • Howes, C. D., Batra, P. P.: Accumulation of lycopene and inhibition of cyclic carotenoids in Mycobacterium in the presence of nicotine. Biochim. Biophys. Acta 222, 174–179 (1970)

    PubMed  Google Scholar 

  • Kleinig, H.: Inhibition of carotenoid synthesis in Myxococcus fulvus (Myxobacterales). Arch. Microbiol. 97, 217–226 (1974)

    PubMed  Google Scholar 

  • Kleinig, H.: On the utilization in vivo of lycopene and phytoene as precursors for the formation of carotenoid glucoside ester and on the regulation of carotenoid biosynthesis in Myxococcus fulvus. Eur. J. Biochem. 57, 301–308 (1975)

    PubMed  Google Scholar 

  • Kleinig, H., Heumann, W., Meister, W., Englert, G.: Carotenoids of Rhizobia. I. New carotenoids from Rhizobium lupini. Helv. Chim. Acta 60, 254–258 (1977)

    PubMed  Google Scholar 

  • Kleinig, H., Reichenbach, H.: Biosynthesis of carotenoid glucoside esters in Myxococcus fulvus (Myxobacterales): Inhibition by nicotine and carotenoid turnover. Biochim. Biophys. Acta 306, 249–256 (1973)

    PubMed  Google Scholar 

  • Kushwaha, S. C., Kates, M.: Effect of nicotine on biosynthesis of C50 carotenoids in Halobacterium cutirubrum. Can. J. Biochem. 54, 824–829 (1976)

    PubMed  Google Scholar 

  • Liaaen-Jensen, S.: Carotenoids of photosynthetic bacteria distribution, structure and biosynthesis. In: Bacterial photosynthesis (H. Gest, A. San Pietro, L. P. Vernon, eds), pp. 19–34, Yellow Springs, Ohio: Antioch Press 1963

    Google Scholar 

  • McDermott, J. C. B., Ben-Aziz, A., Singh, R. K., Britton, G., Goodwin, T. W.: Recent studies of carotenoid biosynthesis in bacteria. Pure Appl. Chem. 35, 29–45 (1973)

    PubMed  Google Scholar 

  • McDermott, J. C. B., Brown, D. J., Britton, G., Goodwin, T. W.: Alternative pathway of zeaxanthin biosynthesis in a Flavobacterium species. Experiments with nicotine as inhibitor. Biochem. J. 144, 231–243 (1974)

    PubMed  Google Scholar 

  • Singh, R. K., Ben-Aziz, A., Britton, G., Goodwin, T. W.: Biosynthesis of spheroidene and hydroxyspheroidene in Rhodopseudomonas species: experiments with nicotine as inhibitor. Biochem. J. 132, 649–652 (1973)

    PubMed  Google Scholar 

  • Vetter, W., Englert, G., Rigassi, N., Schwieter, U.: Spectroscopic methods. In: Carotenoids (O. Isler, ed.), pp. 189–266, Basel: Birkhäuser 1971

    Google Scholar 

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Kleinig, H., Meister, W. & Englert, G. Carotenoids of Rhizobia. Arch. Microbiol. 119, 71–74 (1978). https://doi.org/10.1007/BF00407930

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