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Production of a novel indole ester from 2-aminobenzoate by Rhodobacter sphaeroides OU5

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Journal of Industrial Microbiology and Biotechnology

Abstract

Culture supernatants of Rhodobacter sphaeroides OU5 grown in the presence of 2-aminobenzoate gave an orange-red color-reaction with Salper’s reagent, suggesting the presence of an indole derivative. This production was light-dependent and inducible only with 2-aminobenzoate. Replacement of 2-aminobenzoate with other 2-substituted benzoates did not result in the formation of indole. Fumarate appeared to be the conjugating molecule with 2-aminobenzoate, resulting in the formation of an indole derivative. The purified indole derivative was orange-brown in color, with a yields 0.34 mM from 1 mM 2-aminobenzoate. Infrared analysis suggested an indole ester and 1H NMR analysis indicated an indole carboxylate, esterified with a terpenoid alcohol. The indole ester has a mass of 441 with the molecular formula C27H39NO4. The IUPAC name of the compound is (3 E,5 E)-14-hydroxy-3,7,11-trimethyl-3,5-tetradecadienyl 2-(hydroxymethyl)-1 H-indole-3-carboxylate; and the common name given to this compound is sphestrin.

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Acknowledgements

M.R.S. and Ch.V.R./Ch. S. thank the Council of Scientific and Industrial Research (CSIR), Government of India, for their support through a fellowship (JRF) and research grant, respectively. Ch.V.R. and Ch.S. thank the Department of Ocean Development (DOD) and the Department of Biotechnology, Government of India, for financial support, Professor D. Basavaiah for extending facilities for 1H NMR and IR, IICT for mass analysis and the Department of Science and Technology, Government of India, for FIST support.

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Authors and Affiliations

  1. Department of Plant Sciences, School of Life Sciences, University of Hyderabad, P.O. Central University, Gachibowli, Hyderabad, 500046, India

    M. R. Sunayana & Ch. V. Ramana

  2. Environmental Microbial Biotechnology Laboratory, Center for Environment, Institute of Science and Technology, JNT University, Kukatpally, Hyderabad, 500072, India

    Ch. Sasikala

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  1. M. R. Sunayana
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  2. Ch. Sasikala
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  3. Ch. V. Ramana
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Correspondence to Ch. V. Ramana.

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Sunayana, M.R., Sasikala, C. & Ramana, C.V. Production of a novel indole ester from 2-aminobenzoate by Rhodobacter sphaeroides OU5. J IND MICROBIOL BIOTECHNOL 32, 41–45 (2005). https://doi.org/10.1007/s10295-004-0193-y

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  • DOI: https://doi.org/10.1007/s10295-004-0193-y

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