Thiopropanal S-oxide:  a lachrymatory factor in onions

Brodnitz, Michael H.; Pascale, John V.

doi:10.1021/jf60174a009

Cited by 126 publications

(57 citation statements)

References 7 publications

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“…Cyclodextrin use will be limited to very special applications where competing processes fail or where very high value materials must be protected. Coacervation has found limited use in flavor encapsulation (56)(57)(58). However, work is currently in progress on this method and perhaps we will see its application in the future (59)(60)(61); it is therefore considered in this review.…”

Section: Ch 2 Ohmentioning

confidence: 99%

Flavor encapsulation

Reineccius

1989

Food Reviews International

133

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Section: Ch 2 Ohmentioning

confidence: 99%

Flavor encapsulation

Reineccius

1989

Food Reviews International

133

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“…In Cavallito's studies, antimicrobial activity was found neither with aqueous garlic extracts lacking allicin nor following the addition of GO or diallyl sulfides (5) and no allyl sulfides were found in freshly prepared aqueous garlic clove extracts (6). Also, an early gas chromatographic study (4) indicated that the relatively rapid decomposition of allicin present in aqueous garlic extracts (14) involved transformation mainly to diallyl sulfides. For these reasons it was concluded that GO and its constituent sulfides lack antimicrobial activity.…”

mentioning

confidence: 99%

Antimicrobial Properties of Garlic Oil against Human Enteric Bacteria: Evaluation of Methodologies and Comparisons with Garlic Oil Sulfides and Garlic Powder

Ross

O’Gara

Hill

et al. 2001

Appl Environ Microbiol

308

176

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The antimicrobial effects of aqueous garlic extracts are well established but those of garlic oil (GO) are little known. Methodologies for estimating the antimicrobial activity of GO were assessed and GO, GO sulfide constituents, and garlic powder (GP) were compared in tests against human enteric bacteria. Test methodologies were identified as capable of producing underestimates of GO activity. Antimicrobial activity was greater in media lacking tryptone or cysteine, suggesting that, as for allicin, GO effects may involve sulfhydryl reactivity. All bacteria tested, which included both gram-negative and -positive bacteria and pathogenic forms, were susceptible to garlic materials. On a weight-of-product basis, 24 h MICs for GO (0.02 to 5.5 mg/ml, 62 enteric isolates) and dimethyl trisulfide (0.02 to 0.31 mg/ml, 6 enteric isolates) were lower than those for a mixture of diallyl sulfides (0.63 to 25 mg/ml, 6 enteric isolates) and for GP, which also exhibited a smaller MIC range (6.25 to 12.5 mg/ml, 29 enteric isolates). Viability time studies of GO and GP against Enterobacter aerogenes showed time-and dose-dependent effects. Based upon its thiosulfinate content, GP was more active than GO against most bacteria, although some properties of GO are identified as offering greater therapeutic potential. Further exploration of the potential of GP and GO in enteric disease control appears warranted.Garlic (Allium sativum) has traditional dietary and medicinal applications as an anti-infective agent (11,17). In vitro evidence of the antimicrobial activity of fresh and freeze-dried garlic extracts against many bacteria (5, 16), fungi (1), and viruses (20) supports these applications.Early steps involved in identifying the active constituents of garlic were the discovery that the compound allicin (allyl 2-propene thiosulfinate) is formed when garlic cloves are crushed (5, 6, 7) and that its formation depends upon the action of the enzyme alliinase of the bundle sheath cells upon the alliin of mesophyll cells (19). Methyl and allyl sulfide derivatives of allicin are formed by the steam distillation of mashed garlic (13) to produce garlic oil (GO), which is used in many medicinal garlic products.The classic studies of Cavallito and coworkers (5, 6, 7) attributed the antibacterial properties of garlic clove homogenates to allicin. These properties were confirmed against Escherichia coli and Staphylococcus aureus for garlic clove homogenates plus related garlic compounds and commercial supplements (9). In Cavallito's studies, antimicrobial activity was found neither with aqueous garlic extracts lacking allicin nor following the addition of GO or diallyl sulfides (5) and no allyl sulfides were found in freshly prepared aqueous garlic clove extracts (6). Also, an early gas chromatographic study (4) indicated that the relatively rapid decomposition of allicin present in aqueous garlic extracts (14) involved transformation mainly to diallyl sulfides. For these reasons it was concluded that GO and its constituent sulfides lack antimi...

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“…The substance causing this irritation, a lachrymatory factor (LF), was identified as propanethial S-oxide by Brodnitz and Pascale more than 35 years ago. 1) LF belongs to the group of thioaldehyde S-oxides, and to date, only three other naturally occurring thioaldehyde S-oxides have been reported: (Z,Z)-d,l-2,3-dimethyl-1,4-butanedithial S,S 0 -dioxide from onion;…”

mentioning

confidence: 99%