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Grown In Montana is a federally registered trademark regulated by the Montana Department of Commerce.   REGISTRATION NUMBER is #14669
Made in Montana, PO Box 200533, Helena, MT 59620-0533.

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Garlic Chemestry

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/

garlic head and cloves.png

Garlic's Organosulfur Compounds

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 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.

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

A 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. 

Garlic is a particularly rich source of organosulfur compounds, which are thought to be responsible for its flavor and aroma.  When garlic is cut or smashed it releases flavor compounds.   There are two (2) 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 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.

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 the 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. 

Garlic (Allium sativum) is among the oldest of all cultivated plants. The garlic compounds appear to target multiple pathways, including the mutagenesis inhibition, enzyme activities modulation, inhibition of DNA adduct, affecting the intrinsic pathway for apoptotic cell death and cell cycle machinery which may all contribute to their anticancer activities. It has been suggested that anticancer effect is due to the organosulfur compounds in the garlic and act through 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 clinical assessment of these compounds for 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, antihelminthic and hypotensive effects; it is commonly used to treat chronic bronchitis, recurrent upper respiratory tract infections and influenza.   It has been used for medicinal purpose 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 behaviour 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 possible mechanism of garlic in cancer.

 

Garlic (Allium sativum), a member of the family Liliaceae, contains an abundance of chemical compounds that have been shown to possess beneficial effects to protect against several diseases, including cancer. Evidence supports the protective effects of garlic in stomach, colorectal, breast cancer in humans. The protective effects appear to be related to the presence of organosulfur compounds, predominantly allyl derivatives, which also have been shown to inhibit carcinogenesis in forestomach, esophagus, colon, mammary gland and lung of experimental animals. The exact mechanisms of the cancer-preventive effects are not clear, although several hypotheses have been proposed. Organosulfur compounds modulate the activity of several metabolizing enzymes that activate (cytochrome P450s) or detoxify (glutathione S-transferases) carcinogens and inhibit the formation of DNA adducts in several target tissues. Antiproliferative activity has been described in several tumor cell lines, which is possibly mediated by induction of apoptosis and alterations of the cell cycle. Organosulfur compounds in garlic are thus possible cancer-preventive agents. Clinical trials will be required to define the effective dose that has no toxicity in humans.

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. 

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.

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 longest for the body to break down. It is absorbed in the gastrointestinal tract and passes into the bloodstream, then passes 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 compound is excreted from the body, causing a faint, lingering, garlicky aroma.

 

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.


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

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