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Crushing Garlic and Slicing Onions: Detection of Sulfenic Acids and Other Reactive Organosulfur Intermediates from Garlic and Other Alliums using Direct Analysis in Real-Time Mass Spectrometry (DART-MS)

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Pages 1085-1093 | Received 25 Jun 2010, Accepted 07 Jul 2010, Published online: 12 Jul 2011
 

Abstract

Direct analysis in real-time mass spectrometry (DART-MS) under both positive-ion (PI) and negative-ion (NI) high-resolution (HR) conditions has been used to identify reactive sulfur-containing compounds formed from cutting seven different genus Allium species, garlic, onion, elephant garlic, leek, Chinese chives, and the ornamental species, Allium siculum and A. stipitatum. From cut garlic, PI-DART-MS shows allicin, allyl/methyl and dimethyl thiosulfinates, diallyl trisulfane S-oxide, allyl alcohol, and propene, whereas NI-DART-MS shows 2-propenesulfenic acid, 2-propenesulfinic acid, SO2, and pyruvate. From cut onion, PI-DART-MS shows mainly the lachrymatory factor (LF), along with much lower amounts of thiosulfinates, zwiebelanes, and a bis-sulfine. From cut elephant garlic, both allicin and LF are found, along with thiosulfinates and bis-sulfine. From cut leek, using PI-DART-MS, mixed methyl-1-propenyl-n-propyl thiosulfinates are found, whereas cut Chinese chive shows predominantly methyl with lesser amounts of mixed allyl/methyl thiosufinates. From cut A. siculum, PI-DART-MS shows butanethial S-oxide along with lesser amounts of mixed 1-butenyl/n-butyl/methyl thiosulfinates, while from cut A. stipitatum, N-hydroxy-2-pyridinethione (pyrithone) is seen. PI-DART-MS analysis of all six cut Allium species showed that disulfanes and polysulfanes were absent, which is consistent with these compounds being artifacts from handling and analysis.

Acknowledgments

Support from the National Science Foundation (CHE-0744578; E.B.) is gratefully acknowledged.

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