Production of a novel indole ester from 2-aminobenzoate by Rhodobacter sphaeroides OU5.
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 (1)H NMR analysis indicated an indole carboxylate, esterified with a terpenoid alcohol. The indole ester has a mass of 441 with the molecular formula C(27)H(39)NO(4). 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.
Sunayana
M R
MR
Department of Plant Sciences, School of Life Sciences, University of Hyderabad, P.O. Central University, Gachibowli, Hyderabad 500046, India.
Sasikala
Ch
Ch
Ramana
Ch V
ChV
D001711:Biotransformation; D005650:Fumarates / Q000378:metabolism; D007211:Indoles / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D012242:Rhodobacter sphaeroides / Q000378:metabolism*; D013055:Spectrophotometry, Infrared; D062367:ortho-Aminobenzoates / Q000378:metabolism*
D005650:Fumarates; D007211:Indoles; D062367:ortho-Aminobenzoates; C031385:anthranilic acid; C032005:fumaric acid
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