Thiosulfinate

Thiosulfinate: A Comprehensive Encyclopedic Reference

1. Identity, Chemical Characterization, and Natural Sources

Chemical Class and General Structure

Thiosulfinates are disulfide-S-monoxides and, as products of the condensation of two sulfenic acids, can be viewed as "sulfenic acid anhydrides." Thiosulfinates share the general formula RS(O)SR′, where the R and R′ groups vary by specific compound. Allicin, the most studied thiosulfinate, features this thiosulfinate functional group, R-S(O)-S-R. The molecular formula of allicin is C₆H₁₀OS₂. Chemically, allicin is defined by a thiosulfinate group (S⁺-S⁻) and two allyl moieties.

Nomenclature and Synonyms

Allicin (allyl 2-propenethiosulfinate or diallyl thiosulfinate or S-allyl cysteine sulfoxide) is a sulfur-containing volatile compound found in white garlic (Allium sativum L.) and in other Allium species. Allicin is an oily, slightly yellow liquid that gives garlic its distinctive odor. It is a thioester of a sulfinic acid, also known as allyl thiosulfinate. Allicin is chiral but occurs naturally only as a racemate.

Natural Sources

The most common thiosulfinates cited for biological applications are compounds extracted from plants from the genus Allium, which include garlic, leeks, shallots, chives, onions, etc. Alliin is an organic sulfur-containing product derived from the amino acid cysteine and is the precursor of thiosulfinates, which are responsible for the characteristic pungent flavors of Allium species. Allicin is the major thiosulfinate formed when tissue cells of Allium species are damaged, allowing alliinase to react with alliin.

Allium and Brassica plant genera contain high concentrations of organosulfur compounds, specifically thiosulfinates (between 1.1–3% in garlic, Allium sativum). In onion (Allium cepa), a distinct thiosulfinate predominates: in onion, the most common organosulfur compounds are isoalliin (S-propenyl-L-cysteine sulfoxide) and propiin (S-propyl-L-cysteine sulfoxide). When an onion is crushed or cut, propiin changes into propyl-propane thiosulfinate (PTS) due to the action of the enzyme alliinase. In Brassica vegetables, methiin is metabolized to (+)-S-alk(en)yl-L-cysteine sulfoxides, which can degrade to volatile organosulfur compounds such as S-methyl methane thiosulfinate.

All dipropenyl thiosulfinates (allicin, 1-propenyl allyl, and allyl 1-propenyl) are formed at an optimum pH of 4.5–5.0. The methyl propenyl thiosulfinates and dimethyl thiosulfinate are optimally formed at pH 6.5–7.0 and pH 5.5, respectively.

Thiosulfinates are not naturally present in Allium vegetables, but are generated upon processing operations such as crushing. Crushed raw garlic is high in allicin, containing approximately 37 mg/g.

Biosynthetic Pathway

Allicin (diallyl thiosulfinate), the principal bioactive agent derived from garlic, is not intrinsically present in intact cloves. Its formation is triggered by mechanical disruption (crushing or cutting), which initiates an enzymatic process mediated by alliinase. This enzyme catalyzes the conversion of the stable precursor alliin (S-allyl-L-cysteine sulfoxide) into allyl sulfenic acid. Subsequently, two molecules of allyl sulfenic acid spontaneously condense to form allicin, a reaction that occurs almost instantaneously and releases the characteristic pungent odor of fresh garlic.

Biosynthesis of allicin from S-allyl cysteine sulfoxide (alliin) is catalyzed by the enzyme alliinase (a C-S lyase, E.C. 4.4.1.4.), which catalyzes the formation of allylsulfenic acid and dehydroalanine, whereupon two molecules of allylsulfenic acid condense spontaneously to yield one molecule of allicin.

Alliinase is completely and irreversibly inhibited by the acidic conditions found in the stomach. The dipropenyl thiosulfinates were completely formed in 0.3 minutes at 37°C, while the methyl thiosulfinates were not completely formed until 3.5 minutes.

Downstream Metabolites and Chemical Relatives

Allicin is highly reactive and rapidly degrades into a number of oil-soluble sulfur compounds, including ajoene, dithiins, and diallyl polysulfides. One branch of degradation forms diallyl trisulfide (DATS), diallyl disulfide (DADS), diallyl sulfide (DAS), allyl methyl disulfide, allyl mercaptan, and allyl methyl sulfide. Another branch forms (E)-ajoene and (Z)-ajoene isomers. Other thiosulfinate members documented in garlic include allyl methyl thiosulfinate and methyl allyl thiosulfinate, arising from the parallel action of alliinase on minor cysteine sulfoxide substrates such as methiin.

2. Traditional and Historical Use

Ancient and Cross-Cultural Origins

Since ancient times, garlic has been used worldwide, not only as a food, but also as a medicine. As early as 3000 B.C., in ancient civilizations including Egyptian, Phoenicians, Greek, Indian, Roman, Babylonian, Viking, and Chinese, garlic was used therapeutically. Their medicinal properties and therapeutic effects have been described thousands of years ago, while they constitute an important ingredient in traditional medicines and preparations.

Ancient Egypt

In ancient Egypt, garlic was sometimes termed as the "plant of immortality," a testament to its sacred status and its use in rituals, mummification, and as nourishment for laborers building the pyramids. The ancient Egyptians well-documented the antiquity of garlic as a remedy for respiratory and gastrointestinal ailments, and also incorporated it into a diverse array of nutritional and therapeutic products. In many cultures, garlic was administered to provide strength and increase work capacity for laborers.

Greek and Roman Traditions

Hippocrates, the revered physician, prescribed garlic for a variety of conditions. Garlic was given to the original Olympic athletes in Greece, as perhaps one of the earliest "performance-enhancing" agents. The Greeks and Romans often crushed garlic to release its allicin compound, believed to possess significant health benefits, and mixed it with wine to create medicinal tinctures for treating digestive disorders and infections.

Medieval Europe and Later European Traditions

In medieval Europe, garlic-infused wine became a common remedy for various illnesses, capitalizing on the renowned antimicrobial properties of garlic. Garlic-derived preparations were also historically used during plague epidemics. Sulfur-containing molecules have a long history of bioactivity, especially as antibacterial agents in the fight against infectious pathogens. Organosulfur compounds from natural products have been used to treat infections throughout history.

Ayurvedic and Chinese Traditional Medicine

Traditional systems, such as Ayurveda and traditional Chinese medicine, recognized garlic's benefits for digestion, immunity, and infection control, shaping herbal medicine today. It has traditionally been used in many cultures to treat a variety of human medical conditions, such as lung diseases, arthritis, and the common cold.

Preparations Used Historically

Throughout history, garlic has been prepared and utilized in diverse forms — fresh, cooked, crushed, and infused in liquids such as wine — with each method enhancing its culinary and medicinal properties. Because thiosulfinates are only generated upon physical disruption of the plant tissue, preparations that involved crushing, chopping, or bruising garlic would have delivered the highest amounts of these active compounds. Cooked or aged preparations, by contrast, would be substantially lower in thiosulfinate content due to heat and time-dependent degradation.

3. Key Constituents, Active Compounds, and Mechanisms of Action

Principal Thiosulfinates

The allyl thiosulfinates, of which allicin (diallyl thiosulfinate) is the most abundant and most studied member, are enzymatic products of alliin and alliinase. They are rapidly formed when raw garlic cloves undergo cell rupture, or when dried and pulverized cloves (garlic powder) become wet. The allyl thiosulfinates have been shown to be responsible for most of the pharmacological activity of crushed raw garlic cloves.

In Allium sativum, thiosulfinates (allicin), sulfides [diallyl disulfide (DADS)], vinyldithiins, ajoenes, diallyl trisulfide (DATS), and related compounds constitute up to 82% of the total sulfur content. Allicin, S-methyl cysteine sulfoxide (MCSO), and S-propylcysteine sulfoxide (PCSO), upon acted on by various enzymes, further produce molecules that include allyl methane thiosulfinates, methyl methanethiosulfonate, and other thiosulfinates.

Thiol-Reactive Mechanism

Allicin is a reactive thiol-trapping sulfur compound that S-thioallylates accessible cysteine residues in proteins and low molecular weight thiols including the cellular redox buffer glutathione (GSH) in eukaryotes and Gram-negative bacteria, as well as bacillithiol (BSH) in Gram-positive firmicutes.

The reactivity of thiosulfinates toward thiol groups is an important component of their antimicrobial activity. The electron-withdrawing effect of the O-atom creates an electrophilic sulfur centre which reacts readily with thiols, or more specifically, with thiolate ions, thereby forming an S-allylmercapto adduct. Thus, many enzymes with catalytically important thiol-groups are oxidized and inhibited when exposed to allicin.

Growth inhibition of Escherichia coli during allicin exposure coincides with a depletion of the glutathione pool and S-allylmercapto modification of proteins, resulting in overall decreased total sulfhydryl levels. This is accompanied by the induction of the oxidative and heat stress response.

Dose-Dependent Cellular Effects

Allicin shows dose-dependent antimicrobial activity. At higher doses in eukaryotes, allicin can induce apoptosis or necrosis, whereas lower, biocompatible amounts can modulate the activity of redox-sensitive proteins and affect cellular signaling.

Antioxidant Mechanisms

The biological activity of allicin can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins. The modulation of key antioxidant enzymes, including catalase and glutathione peroxidase, has been described in connection with thiosulfinate exposure.

4. Scientific Evidence by Area of Use

4.1 Antimicrobial Activity

Antibacterial Evidence

Allicin (diallylthiosulfinate) is a defence molecule from garlic with broad antimicrobial activities in the low µM range against Gram-positive and Gram-negative bacteria, including antibiotic-resistant strains, and fungi. Allicin reacts with thiol groups and can inactivate essential enzymes. However, allicin is unstable at room temperature and antimicrobial activity is lost within minutes upon heating to >80°C.

Allicin was synthesized (>98% pure) by oxidation of diallyl disulfide by H₂O₂ using formic acid as a catalyst, and the growth inhibitory effect of allicin vapor and allicin in solution to clinical isolates of lung pathogenic bacteria from the genera Pseudomonas, Streptococcus, and Staphylococcus, including multi-drug resistant (MDR) strains, was demonstrated.

Gram-positive bacteria are typically more sensitive than Gram-negative bacteria to allicin, which is likely attributable to the differing cell wall structure and composition, in particular the presence of lipopolysaccharide-containing outer membrane of Gram-negative bacteria.

Evidence strength: The antibacterial evidence is robust at the in vitro level, with well-replicated minimum inhibitory concentration (MIC) data. Clinical (human) trial data on allicin as a standalone antibiotic in humans remain absent; the evidence base is therefore currently preclinical.

Antifungal Evidence

The minimum inhibitory concentration (MIC) of allicin against Cryptococcus neoformans H99 was 2 µg/ml, which is comparable to fluconazole (1 µg/ml). Allicin exhibited effective antifungal activity against 46 clinical isolates of C. neoformans, with MICs ranging from 1 to 8 µg/ml, even for amphotericin B-insensitive strains. Allicin also exerted additive or synergistic effects when combined with amphotericin B and fluconazole.

In vitro, allicin inhibited the growth of Trichosporon asahii planktonic cells and biofilm cells significantly. In vivo, allicin improved the mean survival time of mice with systemic trichosporonosis and reduced tissue fungal burden. Electron microscopy observations clearly demonstrated damage to T. asahii cell morphology and ultrastructure caused by allicin.

Evidence strength: Antifungal data are primarily from in vitro and animal studies. Controlled human clinical trials are lacking for thiosulfinate-specific antifungal indications.

Anti-Helicobacter pylori Activity

Allyl-thiosulfinates have been described as bacteriostatic compounds of garlic against Helicobacter pylori. The mechanism is consistent with thiol-trapping activity against enzymes essential for the bacterium's survival. Evidence at the human trial level is limited; most data are from in vitro and ex vivo experiments.

4.2 Cardiovascular Health

Mechanisms

Allicin (diallyl thiosulfinate) is one of the primary natural active ingredients in garlic and has been studied for powerful cardioprotective effects. It has been shown to mediate various pathological processes related to cardiovascular disease (CVD), such as inflammatory factor secretion, myocardial cell apoptosis, and oxidative stress.

Reviews have summarized the biological functions of allicin and its potential mechanisms in CVD, including antioxidation, anti-inflammation, and anti-apoptosis effects, covering conditions such as atherosclerosis, hypertension, myocardial infarction, arrhythmia, cardiac hypertrophy, heart failure, and cardiotoxicity.

Blood Pressure

Clinical studies examining the effects of a garlic-supplemented diet to elevate blood allicin levels have indicated that this can significantly reduce systolic blood pressure in hypertensive patients. A meta-analysis including 20 clinical trials suggested garlic to be superior to placebo in lowering blood pressure in hypertensive patients.

In animal studies, spontaneously hypertensive rats treated for 6 weeks with a daily dose of 80 mg/kg/day of purified allicin added to their chow showed significant reductions in systolic blood pressure from 190 ± 7.5 mmHg to 168 ± 5.7 mmHg (P < 0.0001) and in triglyceride levels from 96 ± 25 mg/dl to 71 ± 19 (P = 0.009). Allicin had no effect on plasma cholesterol, insulin, and adiponectin levels in this model.

Lipid Profile

Preclinical and clinical studies have shown that allicin has important beneficial effects on dyslipidemia and obesity. In experimental models of hyperlipidemia, allicin improved the lipid profile (decreased triglycerides, total cholesterol, and LDL-C) and decreased hyperinsulinemia.

However, not all clinical findings have been positive. A double-blind study involving 42 participants showed no significant alterations in serum HDL cholesterol, triglycerides, blood pressure, and glucose levels during a 12-week supplementation regimen with 900 mg of garlic powder. These inconsistent outcomes in clinical investigations are attributed to either the inadequate stability or the absence of allicin in the preparation used.

Evidence strength: Evidence for blood pressure reduction is moderate and supported by meta-analyses of clinical trials, particularly in hypertensive patients. Lipid-lowering evidence from human trials is inconsistent; differences in preparation, allicin content, and bioavailability between products complicate interpretation.

Antiplatelet and Antithrombotic Activity

Allicin and other garlic organosulfur compounds exhibit antiplatelet activity, perhaps through inhibition of thromboxane synthesis and platelet aggregation. This antiplatelet effect is both a potential benefit (reduced cardiovascular risk) and a safety concern when combined with pharmaceutical anticoagulants (see Section 6).

4.3 Anticancer Activity

Epidemiological and Preclinical Evidence

Numerous studies have documented the positive health benefits of allicin on many chronic conditions, including gastric, hepatic, breast, lung, cervical, prostate, and colon cancer. In epidemiological studies of esophageal cancer, liver cancer, pancreatic cancer, and biliary tract cancer, the anticancer effect of garlic has been confirmed consistently. However, the results obtained from epidemiological studies in gastric cancer and colon cancer are inconsistent.

In vitro studies demonstrated that allicin and its secondary metabolites play an antitumor role by inhibiting tumor cell proliferation, inducing apoptosis, controlling tumor invasion and metastasis, decreasing angiogenesis, suppressing Helicobacter pylori, enhancing the efficacy of chemotherapeutic drugs, and reducing the damage caused by chemotherapeutic drugs.

Human Clinical Evidence

In 2008, a clinical study applied allicin locally to progressive gastric carcinoma. Allicin was administered to 40 patients through gastroscopy at the lesion region 48 hours before gastrectomy. The results revealed that allicin suppressed cancer cell proliferation and growth and promoted cell death. Allicin significantly improved antioxidant status in patients undergoing chemotherapy by declining the levels of derivatives of reactive oxygen species. These clinical approaches indicate that allicin exhibits potential as a robust anticancer agent, demonstrating enhanced therapeutic effectiveness while minimizing adverse effects.

Detailed clinical studies are still required to establish its safety profile, optimal dosage, and long-term therapeutic outcomes.

Evidence strength: Preclinical (in vitro and in vivo animal) evidence for anticancer properties is extensive. Human clinical evidence is sparse — consisting of a small number of trials with limited sample sizes. Large randomized controlled trials are currently absent. Epidemiological evidence is suggestive but inconsistent across cancer types.

4.4 Antioxidant Activity

Allicin (diallyl thiosulfinate) is the major thiol-reactive organosulfur compound produced by garlic plants upon tissue damage. Allicin exerts its strong activity against bacteria and fungi via S-thioallylation of protein thiols and low molecular weight thiols. This thiol-reactivity is also the basis of its antioxidant capacity: by reacting with glutathione and modulating cellular redox status, allicin influences the broader antioxidant defense network.

Evidence strength: Antioxidant properties are well-characterized mechanistically in vitro. Human data confirming clinically meaningful antioxidant outcomes are limited.

4.5 Antiviral Activity

Investigation of the effect of allicin on SARS-CoV-2 infected cells found that exposure of infected Vero E6 and Calu-3 cells to biocompatible allicin doses led to a ~60–70% decrease of viral RNA and infectious viral particles. Future drug research should be directed to exploit the thiol-reactivity of allicin derivatives with increased stability and lower human cell toxicity as antiviral lead compounds.

The antiviral activity of garlic components has been ranked as: ajoene > allicin > allyl methyl thiosulfinate > methyl allyl thiosulfinate.

Evidence strength: Antiviral evidence is currently confined to cell culture experiments. No human clinical trials specifically testing thiosulfinates for viral infections have been reported.

4.6 Anti-inflammatory and Immunomodulatory Activity

Many in vitro and in vivo studies have reported the sulfur-containing compounds allicin and ajoene for their effective anticancer, anti-diabetic, anti-inflammatory, antioxidant, antimicrobial, immune-boosting, and cardioprotective properties. Garlic plants produce volatile organosulfur compounds, such as diallyl thiosulfinate (allicin) and diallyl polysulfanes, which are known for their antimicrobial, antiviral, anticancer, anti-inflammatory, and immunomodulatory effects.

Evidence strength: Primarily preclinical. Mechanistic in vitro data exist, but rigorous human trials focused on thiosulfinate-mediated immunomodulation are lacking.

5. Body Systems and Health Areas Associated with Thiosulfinates

• Cardiovascular system: Blood pressure reduction (moderate clinical evidence), lipid modulation (mixed clinical evidence), antiplatelet/antithrombotic activity (preclinical and mechanistic).
• Immune system and infectious disease: Broad-spectrum antibacterial (strong in vitro, no clinical trials), antifungal (strong in vitro, limited animal data), antiviral (cell culture only), anti-H. pylori (in vitro and bacteriostatic).
• Oncology: Antitumor activity via multiple hallmarks of cancer — apoptosis induction, cell cycle arrest, anti-angiogenesis, and chemotherapy sensitization (mostly preclinical; very limited small clinical data).
• Gastrointestinal system: Traditional use for digestive disorders; epidemiological evidence associating Allium consumption with reduced risk of esophageal, liver, and pancreatic cancers.
• Metabolic health: Preclinical evidence for effects on glucose metabolism, adipogenesis, and insulin sensitivity.
• Respiratory system: Traditional use for lung diseases; in vitro evidence of activity against lung-pathogenic bacteria including MDR strains.

6. Dosage Forms and Reported Dosages

Delivery Forms

An enteric-coated formulation has been applied to hamper stomach disintegration of many commercial garlic supplements and protect against alliinase enzyme inactivation. A microparticulate formulation, in which alliinase and alliin are individually encapsulated inside microspheres, has been developed for pulmonary administration.

A stomach acid-resistant coating on garlic powder tablets is necessary for thiosulfinate release, and carefully prepared garlic powder can release similar amounts of total thiosulfinates to whole garlic cloves.

Because alliinase is inactivated by the acidic pH of the stomach, most powdered garlic tablets are enteric-coated to keep them from dissolving before they reach the neutral pH of the small intestine. Most tablet brands have been found to produce little allicin under these conditions, due mainly to low alliinase activity and prolonged disintegration times.

Bioavailability of Supplemental Thiosulfinates

The dissolution release of thiosulfinates from enteric-coated garlic tablets was found to be >95%. The bioavailability of allyl thiosulfinates from these tablets, measured as breath allyl methyl sulfide, was found to be complete and equivalent to that of crushed fresh garlic.

Four of the five enteric-coated brands studied gave medium to high allicin bioavailability (>65%). Given that allicin is metabolized quickly and extensively before it enters the bloodstream, very little of the ingested dose reaches systemic circulation in its intact form.

Bioavailability is heavily influenced by pharmaceutical formulation and concomitant food intake. For example, the bioavailability from enteric-coated preparations can be markedly diminished when administered with high-protein meals, perhaps due to prolonged gastric retention.

Dosages Reported in Studies

In a preclinical study, spontaneously hypertensive rats were treated for 6 weeks with a daily dose of 80 mg/kg/day of purified allicin added to their chow.

A double-blind clinical study involving 42 participants used a 12-week supplementation regimen with 900 mg of garlic powder.

On average, garlic cloves contain approximately 8 g/kg alliin. Crushed raw garlic is high in allicin, containing approximately 37 mg/g.

Thiosulfinate stability is a major determinant of effective dose delivered. The allyl thiosulfinates of blended fresh garlic were stable for at least 2 years when stored at −80°C. Allicin is unstable at room temperature and antimicrobial activity is lost within minutes upon heating to >80°C.

7. Safety Considerations and Drug Interactions

General Safety Status

Garlic is generally recognized as safe (GRAS) in the United States, though thiosulfinate-specific therapeutic indications are not FDA approved. Interpretation of clinical data must take into account publication bias (preferential publication of positive findings).

Stability and Conversion Hazards

A key challenge in therapeutic use is allicin's inherent chemical instability. It is highly reactive and rapidly degrades into a number of oil-soluble sulfur compounds, including ajoene, dithiins, and diallyl polysulfides. Allicin and its derivatives undergo rapid metabolism and excretion, forming transient compounds that decompose into other low molecular weight and volatile sulfur compounds, such as diallyl sulfide (DAS).

Anticoagulant and Antiplatelet Drug Interactions

Beyond the intrinsic toxicity profile of allicin and garlic-derived preparations, their potential to interact with conventional medications represents an additional key safety consideration. The most extensively documented interaction involves anticoagulant and antiplatelet therapies. Allicin and other garlic organosulfur compounds exhibit antiplatelet activity, perhaps through inhibition of thromboxane synthesis and platelet aggregation. As a result, these compounds may potentiate the effects of anticoagulant and antiplatelet drugs such as warfarin, aspirin, and clopidogrel, thereby increasing the risk of bleeding, particularly with high-dose or prolonged garlic supplementation.

Documented interactions between warfarin and concentrated garlic products have been reported in the literature, including cases of elevated international normalized ratios and bleeding events.

Additional Drug Interactions

Major documented drug interactions include anticoagulants, antidiabetic agents, aspirin, NSAIDs, platelet inhibitors, thrombolytic agents, and herbs including danshen, dong quai, feverfew, ginger, ginkgo biloba, ginseng, and horse chestnut.

Gastrointestinal Effects

Gastrointestinal discomfort — including bloating, gas, and nausea — has been documented at higher intakes. Below pH 3.6, no thiosulfinates are formed. Neutralization of pH fails to restore thiosulfinate generation from garlic previously incubated at pH 3 or below, meaning that the stomach environment itself represents a major barrier to delivery of intact thiosulfinates without protective formulation strategies.

Thermal Degradation

Allicin is unstable at room temperature, and antimicrobial activity is lost within minutes upon heating to >80°C. This means that cooking garlic effectively destroys thiosulfinate content, and any product not handled carefully at low temperatures may contain little or no active thiosulfinate at the time of consumption.

Cell Toxicity at High Doses

At higher doses in eukaryotes, allicin can induce apoptosis or necrosis. Toxicity tests revealed that cell lines differ in allicin tolerance, probably due to differences in cellular glutathione levels. The therapeutic window between antimicrobial/pharmacological efficacy and mammalian cell toxicity is therefore an area of ongoing research.

Nanotechnology and Novel Delivery Research

Considering the tremendous advancement in nanomedicine, nanotechnology-based drug delivery systems show promise in addressing limitations of allicin's clinical applications, including improving its solubility, stability, and bioavailability. These platforms are the subject of active investigation but remain experimental and have not yet translated to approved clinical products.

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