Identification and Characterization of Sulfur Heterocyclic Compounds That Contribute to the Acidic Odor of Aged Garlic Extract

Abstract

The aroma of aged garlic extract (AGE) has been recently characterized as a complexity of seasoning-like, metallic, fatty, and acidic notes; most of the important aroma compounds were identified in a previous study. Besides the 25 previously identified aromas of AGE, several of the odor compounds that contribute to the acidic notes were isolated and identified using various analytical techniques, including gas chromatography coupled with an olfactometry monitoring system (GC–O), accurate and high-performance preparative GC system, GC–MS analysis, and sensory evaluation. The identified aromas include: 2,4-dimethyl-1,3-dithiolane, 2,5-dimethyl-1,4-dithiane, and 2,6-dimethyl-1,4-dithiane. Interestingly, AGE contains all stereoscopic isomers of each of these components. An aroma recombinant composed of the newly identified acidic odors with other key odorants showed good agreement with the aroma of AGE.

Role of Sulfur Compounds in Vegetable and Mushroom Aroma

“…Literature data on key odorants in vegetables can be divided into early works on crucial sensory active compounds, especially in Allium vegetables; some works are on other vegetables, mainly Brassica, and there are works, especially in recent years, on compounds migrating in the cold pressing of rapeseed oils, especially after roasting seeds [69,[100][101][102].…”

Protective effects of volatile components of aged garlic extract against ultraviolet B‐induced apoptosis in human skin fibroblasts

“…To the best of our knowledge, this is the first report demonstrating that volatile components contribute to health‐promoting effects of AGE against cell damage. Recently, we identified more than 25 odor active compounds in AGE and found that these were mostly absent in fresh garlic (Abe et al, 2020, 2021). GC–MS analysis in the present study again revealed the significant change in the volatile components that occurs during the aging process of fresh garlic.…”

“…Allyl methyl sulfide, diallyl sulfide, allyl methyl disulfide, diallyl disulfide, trans-2-methyl-2-butenal, trimethylpyrazine and 3-hydroxy-butanoic acid, and ethyl ester were purchased from Tokyo Chemical Industry Co., Ltd. (Tokyo, Japan). The compounds cis/trans-2,4-dimethyl-1,3dithiolane, trans-2,6-dimethyl-1,4-dithiane, 2-vinyl-4H-1,3-dithiin, S-methylmethanethiosulfinate, and 3-vinyl-4H-1,2-dithiin were synthesized as described previously (Abe et al, 2020(Abe et al, , 2021. Antibodies against extracellular signal-regulated kinase (ERK), phospho-ERK, c-Jun N-terminal kinase (JNK), phospho-JNK, p38, and phospho-p38 were purchased from Cell Signaling Technology (Beverly, MA, USA).…”

“…On the other hand, little attention has been focused on the volatile components of AGE other than allicin, despite the fact that plant volatile compounds have been shown to have various bioactivities, including anti-inflammatory and anticarcinogenic activities (Edris, 2007;Shaaban et al, 2012). Recently, we investigated the aroma profile of AGE and demonstrated that several characteristic volatile compounds that are not present in fresh garlic are generated during aging (Abe et al, 2020(Abe et al, , 2021. However, it remains unknown whether these volatile compounds have any beneficial biological effects.…”

Changes in the aroma and key odorants from white garlic to black garlic using approaches of molecular sensory science: A review

“…1 ), which causes the unpleasant taste and aroma of garlic, is broken down into volatile substances such as allyl methyl sulfide and allyl mercaptan when consumed [ 10 , 11 ]. Due to this pungent odor and aroma, many people do not want to consume this crucial vegetable with many health benefits and because of this, the consumption of garlic remains very limited [ 1 , 10 ].

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