4
28
LU ET AL.
4
. Jones RD, Kavanagh TE, Clarke BJ. Determination of carbaryl residues
in malt and beer and their impact on beer quality. J Am Soc Brew Chem
1
988;46:43–50.
5
6
7
. Carbonel GM. Les r e´ sidus de produits agro-pharmaceutiques: leurs
incidences oenologiques essentielles, comment les limiter? Vignes Vins
1
989;4:37–40.
. Dominguez F. Plagas y Enfermedades de la vid In Plagas y enfer-
medades de las plantas cultivadas. Madrid: Mundi-Prensa; 1993. p 711–
7
69.
. California Wine Institute. California wine sales continue increase, as wine
expands its popularity among Americans. California Wine Institute, 2007.
Available at http://www.wineinstitute.org/resources/statistics/article122.
8
9
. Cabras P, Angioni A. Pesticide residues in grapes, wine, and their proc-
essing products. J Agric Food Chem 2000;48:967–973.
. Girond S, Blazy-Maugen F, Michel G. Influence de quelques pesticides
viticoles sur les levures et la fermentation. Rev Fr Oenol 1989;119:14–22.
Fig. 7. EF value versus time curves of DM residues in sucrose solution.
Color figure can be viewed in the online issue, which is available at
wileyonlinelibrary.com.]
[
1
0. Larue F. IBS: des fongicides qui perturben les fermentations. Vitis 1991;
39:106–108.
1
enzyme and get a more active state. In this state, DM would de-
grade faster than in grape must which contained less energy
matter.
11. Otero D, Man L, Dominguez J. Efecto de los residuos antibi o´ ticos sobre
poblaciones levaduriformes. Su incidencia sobre la calidad del vino (I).
Vitivinicultura 1993;5–6:35–39.
1
1
1
2. Oliva J, Navarro S, Barba A, Navarro G, Salinas R. Effect of pesticide resi-
dues on the aromatic composition of red wines. J Agric Food Chem
Diversities were observed from the curves of EF values in
the two processes, too. In the sucrose solution, the EF values
decreased from 0.50 (0 h) to 0.04 (24 h) continuously. How-
ever, in the grape must, the EF values reduced from 0.50 (0
h) to 0.21 (60 h); after this, the EF values presented a slight
rise and got 0.27 at 150 h. This phenomenon might result in
that the material system of the grape must was more com-
plex than the sucrose solution. The material system did not
only affect the physiological activity of the yeast but also had
some actions on the pesticides.
1
999;47:2830–2836.
3. Sala C, Fort F, Busto O, Zamora F, Arola L, Guasch J. Fate of some com-
mon pesticides during vinification process. J Agric Food Chem 1996;
4
4:3668–3671.
4. Zhang K, Wong JW, Hayward DG, Sheladia P, Krynisky AJ, Schenck FJ,
Webster MG, Ammann JA, Ebeler SE. Multiresidue pesticide analysis of
wines by dispersive solid-phase extraction and ultrahigh-performance
liquid chromatography-tandem mass spectrometry. J Agric Food Chem
2009;57:4019–4029.
15. Jim e´ nez JJ, Bernal JL, Toribio L. Persistence and degradation of metal-
axyl, lindane, fenvalerate and deltamethrin during the wine making pro-
cess. Food Chem 2007;104;216–223.
Chiral Stability of DM in the Fermentation
1
6. Ruediger GA, Pardon KH, Sas AN, Godden PW, Pollnitz AP. Fate of
pesticides during the winemaking process in relation to malolactic
fermentation. J Agric Food Chem 2005;53:3023–3026.
Chiral stability suggests that there are no enantiomeriza-
tions of the two enantiomers during the degradation process.
Simply, there is no transformation of (S)-enantiomer to
1
7. Goto T, Ito Y, Oka H, Saito I, Matsumoto H, Sugiyama H, Ohkubo C,
Nakazawa H, Nagase H. The high throughput analysis of N-methyl carba-
mate pesticides in wine and juice by electrospray ionization liquid chro-
matography tandem mass spectrometry with direct sample njection into a
short column. Anal Chim Acta 2005;531:79–86.
(
R)-enantiomer or vice versa. The two enantiomers of DM
were separately studied in the two kinds of matrix in the
experiment mentioned above. The trials detected the enan-
tiomers until they degraded completely, but still no enantio-
merizations were found in all trials. Based on these results, a
conclusion could be drawn that enantiomerization did not
occur in the enantioselective degradation of DM during the
fermentation in both kinds of matrix. Further studies are
required to illustrate the enantioselective mechanism of DM.
The results may help to understand the detailed biological
behavior of chiral pesticide better.
1
1
8. Williams A. Opportunities for chiral agrochemicals. Pest Sci 1996;46:3–9.
9. Zadra C, Marucchini C, Zazzerini A. Behavior of metalaxyl and its pure
R-enaniomer in sunflower plants (Helianthus annus). J Agric Food Chem
2
002;50:5373–5377.
2
0. Liu DH, Wang P, Zhou WF, Gu X, Chen ZS, Zhou ZQ. Direct chiral
resolution and its application to the determination of fungicide benalaxyl
in soil and water by high-performance liquid chromatography. Anal Chim
Acta 2006;555:210–216.
2
2
2
1. Cai XY, Liu WP, Sheng GY. Enantioselective degradation and ecotoxicity
of the chiral herbicide diclofop in three freshwater alga cultures. J Agric
Food Chem 2008;56:2139–2146.
CONCLUSIONS
2. Xu P, Liu DH, Diao JL, Lu DH, Zhou ZQ. Enantioselective acute toxicity
and bioaccumulation of benalaxyl in earthworm (Eisenia fedtia). J Agric
Food Chem 2009;57:8545–8549.
This is the first report on enantioselective degradation of
chiral pesticides during the fermentation process. It indicates
that enantiomers of chiral pesticides have different degraded
behavior during fermentation. The result also calls for
additional attention to pesticide residues on fermented food
and new laws or rules that take diversities on enantiomers of
chiral pesticides into consideration. Still, more research and
detailed study are required in this field.
3. Shimabukuro ,HR, Hoffer BL. Enantiomers of diclofop-methyl and their
role in herbicide mechanism of action. Pestic Biochem Phys 1995;51:68–
82.
24. Lin KD, Cai XY, Chen SW, Liu WP. Simultaneous determination of
enantiomers of rac-diclofop-methyl and rac-diclofop acid in water by high
performance liquid chromatography coupled with fluorescence detection.
Chin J Anal Chem 2006;5:613–616.
2
5. Wang JF. Pesticide muti-residue detection on grape and wine and the
degradation of pesticides during red wine fermentation. Beijing, China
Agricultural University, PhD dissertation, 2008.
LITERATURE CITED
1
2
3
. Campbell PG. Fermented foods of the world—a dictionary and guide.
London: Butterworths; 1987.
2
6. Gu X, Wang P, Liu DH, Lu YL, Zhou ZQ. Stereoselective degradation of
diclofop-methyl in soil and Chinese cabbage. Pest Biochem Phys 2008;
92:1–7.
. Adams MR. Topical aspects of fermented foods. Trends Food Sci Tech
1
990;1:141–144.
. Farris GA, Cabras P, Spanedda L. Pesticide residues in food processing.
Ital J Food Sci 1992;3:149–169.
27. Zhu J, Hu QY. Study on the polynomial regression analysis for dynamic
of pesticide residues. Chin Agro-environ Prot 1988;12:191–192.
Chirality DOI 10.1002/chir