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Garlic Chemistry

Garlic's Organosulfur Compounds

From an NIH Article:  Organosulfur compounds and possible mechanism of garlic in cancer.  By S.H. Omar⁎ and N.A. Al-Wabel

https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3731019/

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The chemistry of garlic is complex and fascinating.

 

you bite into a juicy clove of garlic, and a flavor explosion rocks your taste buds. It's hot, it's pungent, it's undeniably garlicky. But have you ever wondered what's going on behind the scenes of this culinary champion? Buckle up, because we're about to dive into the crazy chemistry of garlic!

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Let's start with the main attraction: allicin. This sulfur-containing molecule is the mastermind behind garlic's signature sting. It's formed when an enzyme called alliinase meets a compound called alliin, both of which live happily apart in separate compartments of the garlic clove. But the moment you chop or crush that clove, these two besties collide, and allicin is born.

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Allicin is a volatile little devil, evaporating into the air and giving your eyes that watery welcome. It's also the reason garlic breath can linger like a mischievous ghost. But don't underestimate its superpowers! Allicin has been shown to have antibacterial, antifungal, and even cancer-fighting properties. Think of it as a tiny garlic knight, slaying off baddies in your body.

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But allicin is just the tip of the garlic iceberg. Garlic contains a whole orchestra of sulfur-rich compounds, each with its own unique flavor and health benefits. There's diallyl disulfide, the star of roasted garlic's mellow sweetness. There's ajoene, a potent antioxidant hiding in aged garlic. And there's a whole chorus of other sulfurous players, all contributing to garlic's complex and captivating aroma.

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So, the next time you add a sprinkle of garlic to your dish, remember, you're not just adding flavor, you're unleashing a symphony of sulfurous chemistry! It's a delicious reminder that the natural world is full of fascinating secrets waiting to be explored. Now go forth, garlic adventurer, and savor the science behind every bite!

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The main active ingredient in garlic is allicin, which is a sulfur-containing compound that gives garlic its characteristic odor and flavor. Allicin is formed when the enzyme alliinase breaks down the compound alliin, which is present in garlic bulbs.  Allicin has a variety of biological activities, including antibacterial, antifungal, and anti-inflammatory properties. It has also been shown to lower blood pressure and cholesterol levels.  Other compounds in garlic that have biological activity include diallyl disulfide, diallyl trisulfide, and ajoene. These compounds have antioxidant and anti-inflammatory properties.  Garlic is a healthy and versatile vegetable that can be enjoyed cooked or raw. It is a good source of vitamins, minerals, and antioxidants.  If you are seeking hardneck garlic, contact GroEat Farm in Montana.  

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Imagine for a short moment,  you are a garlic plant.  

 

Imagine for a moment that you are a garlic plant.  Unlike the animal predators that scurry past you throughout the day, or the flying insects that take aerial flights past your leaves, you are rooted in place and cannot run away.  Animals need to move around to locate their calories for the day, but you are stuck in the dirt.  You get all of the energy needed for survival from the soil and sun.  Your parents and their distant parents adapted their bodies to resist predation.  The DNA and code you inherited from your mother plant, provide specific instructions on how to become virtually indestructible.  

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Garlic plants have evolved in unique and interesting ways, developing solutions very different from the animal world.  Being rooted to the ground meant they were constrained.  The survival solutions developed by garlic plants is based on chemistry.  Garlic is a particularly rich source of organosulfur compounds, which are thought to be responsible for its flavor and aroma.  When garlic is chewed on by a predator, cut, or smashed it releases compounds.   There are two classes of organic compounds found in whole garlic cloves: L-cysteine sulfoxides and γ-glutamyl-L-cysteine peptides..  None of these compounds are present in garlic until it is chewed, smashed, cut, chopped, or broken.  The name “Allium sativum” is derived from the Celtic word “all”, meaning burning or stinging, and the Latin “sativum” meaning planted or cultivated. The English word, garlic, is derived from the Anglo-Saxon “gar-leac” or spear plant, referring to its flowering stalk.

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Whole garlic clove has no pungency since the volatile products are only released following the interaction of the enzyme, alliinase, with the S-alk(en)ylcysteine sulfoxide (alliin, I) which occurs when tissue is damaged or disrupted. The initial products of this enzymic hydrolysis are ammonia, pyruvate, and an alk(en)ylthiosulphinate (allicin). The latter, which possesses odor characteristics typical of the freshly cut tissue, can undergo further nonenzymic reactions to yield a variety of compounds, including thiosulfinate and di- and trisulfides. 

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Alliums have been featured through the ages in literature, where they are both praised and reviled, as well as in architecture and the decorative arts. The name "Allium" is said to come from the Greek word to avoid because of its offensive smell. The genus Allium includes more than 750 species of which only a few have been cultivated as foods. The smell of garlic is a consequence of the breakdown of sulfur-containing compounds which is a characteristic of this family of plants. Garlic, onions, leeks, chives, and other members of the genus Allium occupy a unique position both as edible plants and herbal medicines, appreciated since the dawn of civilization.

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Alliinase is an important enzyme occurring in Allium species, which includes garlic.   Alliinase converts predecessors of sulfuric compounds, cysteine sulfoxides into allicin, a biologically active substance.  This Allicin helps garlic defend itself against pests, and produces health-promoting compounds for humans. 

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Allyl methyl sulfide is broken down in the body more slowly than the other three compounds listed above.  Allyl methyl is the primary volatile responsible for garlic breath.  It is excreted through sweating, breathing, and through urine.  Its effects can last up to 24 hours.  Few foods have been shown to have some effect on reducing garlic breath including milk and parsley. 

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Garlic (Allium sativum) is among the oldest of all cultivated plants. The garlic compounds appear to target multiple pathways.  It has been suggested that the anticancer effect is due to the organosulfur compounds in the garlic and acts through the induction of phase II detoxification enzymes. It is possible that diallyl disulfide and diallyl trisulfide is important in the anticancer action of garlic. More than one compound is responsible for the anticancer properties of garlic. The peak plasma concentration of DATS in rats following treatment with 10 mg of the compound was shown to be about 31 μmol/L. Although the pharmacokinetic parameters for DATS in humans have not yet been measured, oral administration of 200 mg of synthetic DATS (also known as allitridum) in combination with 100 μg selenium every other day for 1 month to humans did not cause any harmful side effects. Future research should focus on the clinical assessment of these compounds for the prevention/treatment of cancers in humans.

 

Garlic has historically been used to treat earaches, leprosy, deafness, severe diarrhea, constipation, and parasitic infections, and to lower fever, fight infections and relieve stomach aches. Garlic and its extracts have been used to treat infections for thousands of years and it has long been revered for its medicinal properties as evidenced by ancient writings from Egypt, Greece, China, and India extolling its merits. Garlic is thought to have diaphoretic, expectorant, antispasmodic, antiseptic, bacteriostatic, antiviral, anthelmintic, and hypotensive effects; it is commonly used to treat chronic bronchitis, recurrent upper respiratory tract infections, and influenza.   It has been used for medicinal purposes for more than 3000 years and has bactericidal, antibiotic, and fungicidal properties. Epidemiologic and preclinical studies suggested that garlic may influence the risk of heart disease and cancer and also as an anticancer dietary component are reported by Fleischauer and Arab. The most compelling evidence that garlic and related sulfur constituents can suppress cancer risk and alter the biological behavior of tumors. Experimentally, garlic and its associated sulfur components are reported to suppress tumor incidence in breast, colon, skin, uterine, esophagus, and lung cancers. A recent meta-analysis also showed that a high intake of garlic may be associated with decreased risks for stomach and colorectal cancer.   This review will briefly focus on constituents and evidence of the possible mechanisms of garlic in cancer.

 

An average clove of garlic weighs between 3 and 6 g and contains an average of 1 g of carbohydrates (90% of which is in a starchy form called sinistrin), 0.2 g of protein, 0.05 g of fiber, 0.01 g of fat and vitamins A, B1, B2, B3 and C. The Vitamin B1 (thiamin) is combined with the allicin and called allithiamine and is easily absorbed into the intestine. Garlic contains about 10 different kinds of natural sugars which make up about a fourth of its substances; they include fructose, glucose, inulin and arabinose. Garlic can reduce blood sugar levels.  Garlic is richer than any other food in adenosine, a nucleic acid which is a building block of DNA and RNA. The primary anti-platelet constituent found in garlic appears to be adenosine. Garlic contains approximately 33 sulfur compounds (aliin, allicin, ajoene, allylpropyl disulfide, diallyl trisulfide, sallylcysteine, vinyldithiines, S-allylmercaptocystein, and others), several enzymes (allinase, peroxidases, myrosinase, and others), 17 amino acids (arginine and others), and minerals (selenium, germanium, tellurium and other trace minerals). Biological effects of garlic are attributed to its characteristic organosulfur compounds. 

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Garlic is frequently used in cooking, but its use comes with the unwanted accompaniment of ‘garlic breath’. On the more beneficial side of things, it can also have antibacterial properties. This post examines the chemical compounds behind these two phenomena.

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Research has identified four major compounds that contribute: diallyl disulfide, allyl methyl sulfide, allyl mercaptan, and allyl methyl disulfide. Of these, allyl methyl sulfide is the compound that takes the longest for the body to break down. It is absorbed in the gastrointestinal tract and passes into the bloodstream, then pass on to other organs in the body for excretion, specifically the skin, kidneys, and lungs. It is excreted through the skin via sweating, in the urine – and through your breath. This effect can last up to 24 hours, until all of the compounds is excreted from the body, causing a faint, lingering, garlicky aroma.

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Much as with onions, the chemicals that lead to ‘garlic breath’ aren’t actually present in unchopped garlic. They are formed when the garlic clove is mechanically damaged; this causes enzymes to break down the compound alliin, found in the cloves, to form allicin. Allicin is the major compound that contributes to chopped garlic’s aroma. It too is broken down into a range of sulfur-containing organic compounds, several of which contribute to the ‘garlic breath’ effect.

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Chemical compounds found in garlic bulb.

Chemical compound    Amount (ppm)


Alanine    1320–31,168 ppm
Allicin    1500–27,800  ppm
Alliin    5000–10,000  ppm
Arginine    6340–15,216 ppm
Aspartic acid    4890–11,736 ppm
Calcium    180–4947 ppm
Carbohydrates    274,000–851,000 ppm
Cystine    650–1560 ppm
Fat    2000–12,000 ppm
Fiber    7000–39,000 ppm
Glutamic acid    8050–19,320  ppm
Glycine    2000–4800 ppm
Histidine    1130–2712 ppm
Isoleucine    2170–5208 ppm
Leucine    3050–7392 ppm
Lysine    2730–6552 ppm
Magnesium    240–1210 ppm
Phenylalanine    1830–4392 ppm
Phosphorus    880–5220 ppm
Potassium    3730–13,669 ppm
Proline    1000–2400 ppm
Protein    35,000–179,000 ppm
Scordinine-A    39,000 ppm
Scordinine-A-1    67–30,000 ppm
Scordinine-A-2    250–8000 ppm
Serine    1900–4560 ppm
Threonine    1570–3768 ppm
Tryptophan    660–1584 ppm
Tyrosine    810–1944 ppm
Valine    2910–6984 ppm
Water    585,000–678,000 ppm

 

Source:  Saudi Pharm J. 2010 Jan; 18(1): 51–58.  Published online 2009 Dec 24. doi: 10.1016/j.jsps.2009.12.007

compounds in garlic, chemical composition of garlic, allicin, bioactive properties, raw garlic,buy garlic seed, damaged garlic, cut garlic, broken down,garlic breath

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