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Aug 4, 2013 - Received: 23 April 2013 /Revised: 27 June 2013 /Accepted: 10 July 2013 /Published ... may be used as a terroir, variety, or wine process tag.

Anal Bioanal Chem (2014) 406:1201–1208 DOI 10.1007/s00216-013-7244-z

RESEARCH PAPER

Isolation, characterization, and determination of a new compound in red wine Sandy Fabre & Christelle Absalon & Noël Pinaud & Christiane Venencie & Pierre-Louis Teissedre & Eric Fouquet & Isabelle Pianet

Received: 23 April 2013 / Revised: 27 June 2013 / Accepted: 10 July 2013 / Published online: 4 August 2013 # Springer-Verlag Berlin Heidelberg 2013

Abstract Chromatographic separation using fluorescence as a detection mode revealed, besides a series of flavan-3-ols, the recurrent presence of an undefined compound in Bordeaux red wine. Its isolation and structure characterization by complementary means (high-resolution mass spectrometry, nuclear magnetic resonance, and chemical synthesis) has permitted us to identify it as the nitrogen-containing glycoconjugate 3indolyl-(2R)-O-β-D-glucosyl-lactic acid. Its quantification was performed for different wines of different vine varieties and terroirs with the aim to assess whether this compound may be used as a terroir, variety, or wine process tag. Keywords Bordeaux red wine . Indole-3-lactate . β-D-Glucopyranoside . High-resolution mass spectrometry . NMR . Chemical synthesis

Introduction During the experiments we performed to identify and quantify procyanidins in wine and grapes [1–3], the high-performance liquid chromatography (HPLC) profiles highlighted the Published in the special issue Analytical Science in France with guest editors Christian Rolando and Philippe Garrigues. Electronic supplementary material The online version of this article (doi:10.1007/s00216-013-7244-z) contains supplementary material, which is available to authorized users. S. Fabre : C. Absalon : N. Pinaud : E. Fouquet : I. Pianet (*) Institut des Sciences Moléculaires, UMR 5255, Université de Bordeaux, 351 cours de la Libération, 33405 Talence, France e-mail: [email protected] C. Venencie Baron Philippe de Rothschild, Rue de Grassi, 33250 Pauillac, France P.

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