Deodorization of Garlic Breath Volatiles by Food and Food Components

The ability of foods and beverages to reduce allyl methyl disulfide, diallyl disulfide, allyl mercaptan, and allyl methyl sulfide on human breath after consumption of raw garlic was examined. The treatments were consumed immediately following raw garlic consumption for breath measurements, or were blended with garlic prior to headspace measurements. Measurements were done using a selected ion flow tube‐mass spectrometer. Chlorophyllin treatment demonstrated no deodorization in comparison to the control. Successful treatments may be due to enzymatic, polyphenolic, or acid deodorization. Enzymatic deodorization involved oxidation of polyphenolic compounds by enzymes, with the oxidized polyphenols causing deodorization. This was the probable mechanism in raw apple, parsley, spinach, and mint treatments. Polyphenolic deodorization involved deodorization by polyphenolic compounds without enzymatic activity. This probably occurred for microwaved apple, green tea, and lemon juice treatments. When pH is below 3.6, the enzyme alliinase is inactivated, which causes a reduction in volatile formation. This was demonstrated in pH‐adjusted headspace measurements. However, the mechanism for volatile reduction on human breath (after volatile formation) is unclear, and may have occurred in soft drink and lemon juice breath treatments. Whey protein was not an effective garlic breath deodorant and had no enzymatic activity, polyphenolic compounds, or acidity. Headspace concentrations did not correlate well to breath treatments.     

Effect of Milk on the Deodorization of Malodorous Breath after Garlic Ingestion

Abstract: The effect of milk and milk components on the deodorization of diallyl disulfide (DADS), allyl methyl disulfide (AMDS), allyl mercaptan (AM), allyl methyl sulfide (AMS), and methyl mercaptan (MM) in the headspace of garlic as well as in the mouth- and nose-space after garlic ingestion was investigated using selected ion flow tube-mass spectrometry (SIFT-MS). Fat-free and whole milk significantly reduced the head-, mouth-, and nose-space concentrations of all volatiles. Water was the major component in milk responsible for the deodorization of volatiles. Due to its higher fat content, whole milk was more effective than fat-free milk in the deodorization of the more hydrophobic volatiles diallyl disulfide and allyl methyl disulfide. Milk was more effective than water and 10% sodium caseinate in the deodorization of allyl methyl sulfide, a persistent garlic odor, in the mouth after garlic ingestion. Addition of milk to garlic before ingestion had a higher deodorizing effect on the volatiles in the mouth than drinking milk after consuming garlic. Practical Application: Ingesting beverages or foods with high water and/or fat content such as milk may help reduce the malodorous odor in breath after garlic ingestion and mask the garlic flavor during eating. To enhance the deodorizing effect, deodorant foods should be mixed with garlic before ingestion.     

Odor Components of Human Breath After the Ingestion of Grated Raw Garlic

The major odor components of finely grated, raw garlic in the air of the human mouth have been studied. Immediately after garlic ingestion, tests of the mouth air of six subjects revealed two major peaks that were positively identified as being allyl mercaptan and diallyl disulfide; these findings are based on an evaluation of the fragment patterns of a GC-MS analysis and from the actual retention times of these authentic compounds. The allyl mercaptan level was higher than the level of diallyl disulfide, although both compounds smell like garlic. Our results suggest that after garlic ingestion, allyl mercaptan is the major garlic-smelling compound in human mouth air, and diallyl disulfide is secondary.     

Alliinase-independent Inhibition of Staphylococcus aureus B33 by Heated Garlic

ABSTRACT: Heated (121 °C) garlic extract in which alliinase was inactivated before crushing exhibited complete bacteriostatic activity at 15% against Staphylococcus aureus. Garlic heated for 45 min showed the highest antibacterial activity and the relative peak areas of 4-heptenal, methyl allyl disulfide, diallyl disulfide, 2-vinyl-4H-1,3-dithiin, and diallyl trisulfide (DATS) were highest at 45 min of heating. Other than 4-heptenal, all these compounds are known to possess different degrees of antibacterial activity. DATS was thought to be the primary antibacterial compound in heated garlic extract. It was tentatively concluded that antibacterial compounds were formed from alliin unreacted by alliinase by marked heating. Diallyl compounds with more than three sulfur atoms and the oxidized form of allicin were not detected.     

Anticarcinogenic properties of garlic: a review

Garlic is a popular spice added to several edible preparations and is a remedy for a variety of ailments. Epidemeological as well as laboratory studies have shown that garlic consumption reduces certain cancer incidences in the stomach, colon, mammary, cervical, etc. This article focuses on the general chemistry, metabolism, anticarcinogenic properties, mechanism of action behind the anticarcinogenic effects, functional foods based on garlic; and future areas of research. Garlic has been shown to metabolized into N-aceryl-S-allyl cysteine, allyl mercaptan, diallyl disulfide, diallyl sulfide, diallyl sulfoxide, diallyl sulfone, and allyl methyl sulfide. Garlic has been thought to bring about its anticarcinogenic effect through a number of mechanisms, such as the scavenging of radicals, increasing gluathione levels, increasing the activities of enzymes such as glutathione S-transferase, catalase, inhibition of cytochrome p4502E1, DNA repair mechanisms, prevention of chromosomal damage etc. Future research should standardize the dosage of garlic and type, ie., whether it should be taken fresh, cooked, or aged. The formulation of odorless functional foods with the retention of anticarcinogenic activity should be further studied.     

Volatile distribution in garlic (Allium sativum L.) by solid phase microextraction (SPME) with different processing conditions

Treatments of autoclaving, high temperature aging (aged-black garlic), crushing, and roasting at 100, 150, and 200°C were applied to alter the volatile profiles of garlic (Allium sativum L.). Headspace volatiles in samples were analyzed by a solid phase microextraction (SPME)-GC/MS. Total peak areas of crushed-raw garlic were the highest and those of aged-black garlic clove were the lowest. Crushing effects were clearly observed in raw garlic, aged-black garlic, and roasted garlic at 200°C for 60 min. Sulfur-containing volatiles including diallyl disulfide and diallyl trisulfide were major volatiles. Generally, peak areas of diallyl disulfide decreased when garlic received autoclaving and roasting treatment while diallyl trisulfide and allyl methyl trisulfide increased during heat treatment compared to raw garlic. Roasting at 200°C for 60 min caused the formation of pyrazines greatly in garlic. Principal component analysis (PCA) for the volatile profiles by SPME-GC/MS could discriminate types of processed garlic successfully.     

大蒜清汁加工中脱臭澄清净化技术研究

以大蒜为原料探究大蒜清汁的加工工艺,并对大蒜的脱臭温度、护色VC用量、果胶酶酶解条件及冷冻澄清进行研究,确定了合理的加工工艺和最佳参数.结果表明,大蒜清汁制取最佳工艺参数为：加热脱臭温度70℃,护色vC用量0.03％,酶解pH 4.62,酶解温度50℃,酶解时间45min.在此条件下得到的大蒜清汁澄清度最高.同时冷冻澄清（-18℃）的方法得到的大蒜出汁率最高,澄清稳定性最好.     

Effects of pH Adjustment and Subsequent Heat Treatment on the Formation of Volatile Compounds of Garlic

Effects of pH adjustment during the blending of garlic cloves and subsequence heat treatment on the formation of volatile compounds of garlic were studied by means of gas chromatography (GC). The formation of the two isomeric cyclic compounds 3-vinyl-[4H]-l,2-dithiin and 2-vinyl-[4H]-l,3-dithiin, which were artifacts from allicin, was favored around pH 5.5. Formation of diallyl trisulfide, methyl allyl trisulfide, cis-1-propenyl allyl disulfide, isobutyl isothiocyanate, 2,4-dimethylfuran, 1,3-dithiane, aniline, methyl allyl sulfide, dimethyl disulfide and 3-methyl-2-cyclopentene-l-thione were favored in neutral or weak acidic conditions, whereas formation of diallyl disulfide, diallyl sulfide, methyl allyl disulfide, propenylthiol, propyl allyl disulfide and 1,2-epithiopropane were favored around pH 9.0.     

Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds

The effects of garlic and selected organosulfur compounds (diallyl disulfide, dipropyl disulfide, diallyl sulfide, allyl methyl sulfide, allyl mercaptan, cysteine, and cystine) on the formation of heterocyclic aromatic amines (HAAs) in fried ground beef patties were evaluated. Minced garlic cloves (ca. 4.8 to 16.7%, wt/wt) or organosulfur compounds (0.67 mmol) were added directly to ground beef. Patties (100 g) were fried at 225 degrees C (surface temperature) for 10 min per side. Two patties were fried for each replication, and five replicates were analyzed for each treatment. For each replicate, four subsamples were analyzed (two unspiked subsamples for concentration and two spiked subsamples for the recovery of HAA standards). The volatile sulfur compounds significantly (P < 0.05) reduced concentrations of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by reductions of 46 to 81%, while average reductions of 35, 22, and 71%, were achieved with cystine, cysteine, and whole garlic, respectively. The volatile sulfur compounds reduced concentrations of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline by 34 to 67%, while reductions of 25, 19, and 63% (P < 0.05) were achieved with cystine, cysteine, and whole garlic, respectively. These studies confirm that garlic and some organosulfur compounds have the potential to reduce HAA formation incooked beef patties.     

Reduction of Heterocyclic Aromatic Amine Formation and Overall Mutagenicity in Fried Ground Beef Patties by Organosulfur Compounds

ABSTRACT: The effects of several organosulfur compounds on heterocyclic aromatic amine (HAA) formation and overall mutagenicity in fried ground beef patties were evaluated. The greatest inhibition of total HAA formation was achieved with diallyl disulfide (78%) and dipropyl disulfide (70%); these compounds also reduced overall mutagenicity by 75 and 65%, respectively. The addition of diallyl sulfide, allyl methyl sulfide, and allyl mercaptan also significantly ( p < 0.05) reduced mutagenicity, with reductions of 56, 43, and 30%, respectively. The addition of cysteine and cystine, however, did not reduce the mutagenicity of cooked meat, an observation confirmed by the relatively small reductions in HAA concentrations.     

Comparative Distribution of Volatile Aliphatic Disulfides Derived from Fresh and Dehydrated Onions

SUMMARY— Gas chromatographic determination of the volatiles from fresh "Sunspice" onions revealed that the principal disulfide present is di-St-propyl, followed in descending, order of concentration by n-propyl allyl, methyl-n-propyl, methyl allyl, dimethyl, and diallyl. In dehydrated onions this order is markedly altered. Methyl-n-propyl is the principal disulfide, followed by dimethyl, methyl allyl, di-n-propyl, n-propyl allyl, and diallyl. Quantitative estimates of the disulfide content of 53 lots of fresh onions were made and compared with analyses of dehydrated onions from comparable lot numbers. Loss of measured volatiles averaged 98%, while loss of disulfides was greater than 89%. The relationship of disulfides to onion flavor and a pungency ranking system based on these analyses are discussed.     

响应面法优化海鲈鱼鱼肉脱腥工艺

摘 要: 目的 确定以香菜、薄荷为主要原料制得的复合脱腥液对海鲈鱼鱼肉的最佳脱腥工艺。方法 通过腥度(腥气、腥味)和感官评分(色泽、气味、滋味、质地)对海鲈鱼鱼肉脱腥效果进行评价, 采用单因素试验和响应面实验研究脱腥液浓度、料液比和脱腥时间, 确定最佳脱腥工艺, 并比较脱腥前后海鲈鱼肉主要挥发性成分及三甲胺含量的变化。结果 最佳脱腥工艺为脱腥液浓度4 g/100 mL, 料液比1:3 (g:mL), 脱腥时间43 min, 脱腥后鱼腥味物质戊醛、己醛和庚醛等明显减弱, 增加了2-茨醇、香叶醇和芳樟醇等清香味物质,三甲胺含量明显降低。结论 最佳脱腥工艺可在脱腥同时赋予鱼肉清香味, 绿色天然、方便有效, 可为海鲈鱼鱼肉脱腥工艺提供参考。     

酶促诱发儿茶素对模拟苹果汁非酶褐变特性的影响

以苹果中含量较多的儿茶素为研究对象,以磷酸缓冲液为苹果汁褐变模拟体系,在多酚氧化酶（polyphenol oxidase,PPO）酶促诱发儿茶素后,钝化PPO,通过色差仪连续测定模拟体系亮度（L*）值、红度（a*）值、黄度（b*）值及总色差（ΔE*）值的变化趋势,研究酶促诱发条件对模拟果汁体系非酶褐变特性的影响。结果表明：酶促诱发时间及诱发体系温度对儿茶素参与的非酶褐变无显著性影响（P＞0.05）,而酶促诱发体系pH值以及儿茶素浓度对模拟体系褐变程度影响显著（P＜0.05）,pH 4.0时,模拟果汁体系褐变程度较大,褐变程度随儿茶素浓度的增大而增强;本实验同时发现,PPO诱发儿茶素发生非酶聚合,并与聚合产物相互作用而沉淀,导致果汁产生后浑浊。     

Investigation of the volatile aroma components of garlic leaves essential oil. Possibility of utilization to enrich garlic bulb oil

The volatile aroma components of Egyptian green garlic leaves essential oil was investigated for the first time. After the utilization of garlic bulbs to prepare garlic oil or after drying the bulbs to produce garlic powder, garlic leaves are considered to be waste material, which is disposed of without any benefit. In this investigation, green garlic leaves were distilled and the essential oil was subjected to GC and GC-MS identification. The yield of the oil was 0.06% (based on wet weight of the leaves). The most prominent compounds of the essential oil were diallyl trisulfide (32.32%), followed by diallyl disulfide (31.35%) and methyl allyl trisulfide (11.40%); these compounds are the same as those found in garlic bulb oil. This means that garlic leaf oil is a rich, renewable and priceless source of garlic aroma compounds which could be utilized in fortification and enriching of garlic bulb essential oil to increase its quantity without changing the quality. Utilization of green garlic leaves for production of essential oil will also save, to some extent, the costs of disposing of large amounts of leaves in garlic possessing factories, transforming them into profits.     

大蒜素和有机溶剂对蒜氨酸酶活性及大蒜油组成的影响

大蒜油具有重要的生物活性和调味功能。本文以化学合成的蒜氨酸为原料在蒜酶的催化下制备大蒜油,研究中间产物大蒜素、萃取溶剂对蒜酶活性的影响,以及溶剂对大蒜油组成成分的影响。结果显示:大蒜素在一定程度上会抑制蒜酶的活性,但不会导致蒜酶的完全失活;有机溶剂对蒜酶的影响比较复杂,其中氯仿、二氯甲烷使蒜酶活性完全丧失,而正己烷、正戊烷对蒜酶的活性影响则不明显。采用气质联用、核磁共振二维谱表征了不同溶剂下大蒜油的组成。用氯仿、正己烷等非极性溶剂萃取大蒜素,得到的大蒜油以3-乙烯基-1,2-二硫环己-4-烯(4X)和3-乙烯基-1,2-二硫环己-5-烯(5X)为主;而用乙酸等质子溶剂萃取,则大蒜油成分以二烯丙基三硫醚(DATS)、二烯丙基二硫醚(DADS)为主。     

Release of volatile compounds from microwave heating of garlic juice with 2,4-decadienals

Garlic (Allium sativum L.) juice and 2,4-decadienals were heated in a microwave oven at the full power of 700 W. The volatile compounds of heated samples were isolated using diethyl ether solvent extraction and analysed using gas chromatography and gas chromatography–mass spectrometry. A total of 23 compounds were identified from these samples, among which 14 sulfide compounds, five aldehydes, two alcohols, one acid and one furan were identified. Three tentatively identified compounds, dithio(1-propenyl)propionate, dihydro-2(3H)-thiophenthione and n-hexanethiol were newly found in deep-fried garlic flavor. During microwave heating, levels of most volatiles decreased as the heating time continued. 2-Pentylfuran, isopropyl alcohol, hexanal and (E)-2-octenal were formed from the degradation of 2,4-decadienals. Sulfur dioxide was generated predominantly from the degradation and oxidation of sulfide compounds.     

泰安大蒜与金乡大蒜挥发性风味物质成分分析

采用自动化静态顶空与气质联用的方法分析对比金乡大蒜与泰安大蒜的挥发性成分,通过GC-MS分析和NIST质谱库计算机检索,对样品进行定性分析,并采用面积归一化法进行定量分析。检测结果表明,不同产地的大蒜中的挥发性风味物质种类略有差别,金乡大蒜中含硫化合物总量高于泰安大蒜,并且,新鲜大蒜含硫化合物含量高于贮藏大蒜,存在显著差异。金乡大蒜和泰安大蒜检出的风味物质种类略有差别,地域性差别对大蒜风味物质种类影响不大,但是,在大蒜风味物质中起决定性作用的1,3-二噻烷、烯丙基三硫化物、烯丙基二硫化物以及而烯丙基四硫醚,在含量上金乡大蒜明显高于泰安大蒜。同时,研究表明,静态顶空与气质联用能够快速、简便、高效、准确地对大蒜中的挥发性风味物质进行组分分析以及鉴定。     

大蒜油的抗凝血作用

为研究大蒜油的抗凝血作用,本实验从大蒜中分离提取大蒜油,经气相色谱-质谱联用仪鉴定该大蒜油中主要成分为二烯丙基硫醚（allyl sulfide,DAS）、二烯丙基二硫醚（diallyl disulfide,DADS）和二烯丙基三硫醚（diallyl trisulfide,DATS）。体外实验结果表明大蒜油、DAS、DADS、DATS均具有部分抑制凝血酶活性功能,且抑制作用由强到弱依次为DATS＞大蒜油＞DADS＞DAS。利用Lineweaver-Burk双倒数作图法进行酶动力学分析,结果表明大蒜油、DAS、DADS、DATS对凝血酶的抑制作用属于混合性抑制（竞争性和非竞争性抑制）。分子荧光光谱分析结果表明大蒜油、DAS、DADS、DATS能与凝血酶蛋白中的发色基团相互作用导致荧光猝灭。三维分子对接分析结果显示出DATS与凝血酶结合性能良好;二维分子对接分析结果显示出DATS与凝血酶蛋白活性位点处Asp189、Gly219和Ala190形成氢键,与酶活性位点的Gly216、Ser195、Trp215形成疏水作用力,体现竞争性抑制作用,与非活性位点Gly226、Asp221A、Tyr225、Glu217、Cys191、Val213形成疏水作用,体现非竞争性抑制作用。体内实验结果表明,大蒜油、DAS、DADS、DATS分别通过正向调控大鼠凝血四项指标而直接展现出抗凝血功能,且抗凝血能力依次为DATS＞DADS＞DAS＞大蒜油。大鼠体内抗氧化实验结果表明大蒜油、DAS、DADS、DATS均只有微弱抗氧化能力,大蒜油、DAS、DADS、DATS具有的抗凝血功能应与其抗氧化能力不相关。     

Synergistic antiyeast activity of garlic oil and allyl alcohol derived from alliin in garlic

ABSTRACT:  Garlic oil (GO) and allyl alcohol (AA), both derived from alliin in garlic using different preparation methods, cause potent growth inhibition in yeasts. GO and AA inhibited Candida utilis ATCC42416 in different ways: GO has fungistatic activity while AA has fungicidal activity. GO and AA have almost identical antimicrobial potencies against the indicator yeast, with minimum inhibitory concentrations of about 25 ppm when tested individually. When GO and AA were tested in combination, the antimicrobial efficacy significantly increased. Combinations of AA and GO at 1 and 9 ppm, 2 and 7 ppm, 5 and 5 ppm, and 6 and 3 ppm, respectively, inhibited C. utilis completely. The sum of the fractional inhibitory concentrations (FICs) in the 2-component (GO and AA) combination was as low as 0.37 for C. utilis , indicating strong synergism. The sum of the FICs of diallyl disulfide and diallyl trisulfide in combination with AA was larger than that of the GO–AA combination, suggesting that the synergy was lower.     

Development of anti-insect multilayered films for brown rice packaging that prevent Plodia interpunctella infestation

The aim of this study was to develop a multilayered insect-proof film that prevents contamination with Plodia interpunctella (Hübner; Lepidoptera: Pyralidae) insect larvae. The anti-insect activities of five essential oils (EOs), allyl disulfide (AD), and allyl mercaptan isolated from garlic and onion, respectively, were evaluated. Subsequently, fumigation insecticidal assays were performed to identify the anti-insect agents, their optimal concentrations. Garlic, onion EOs and their compounds were chosen as efficient anti-insect agents for application to rice flour-based multilayered plastic films. Penetration tests were then used to evaluate the ability of multilayered films to resist invasion by P. interpunctella larvae. Films containing 5% AD (AD-5) had the strongest resistance to penetration by insects. Thus, AD-5 was applied to brown rice packaging to measure protection from insects and to assess sensory properties. In these analyses, AD-5 showed insect-proofing effects and no undesirable changes to the sensory properties of the rice after cooking. Hence, this novel multilayer film could be used as an active packaging material with effective anti-insect activities and desirable physical properties.