Ajoenes

Garlic is used as an antifungal. A cream of 0.4% ajoene (the antifungal component of garlic) was found to relieve symptoms of athlete s foot and, tike tea tree oil, is applied twice daily. (For more information on garlic, see Herbal Alert in Chap. 44.)... 

Ajoene (Spanish, ajo, garlic), 4,5,9-trithiadodeca-l,6,ll-triene-9-oxide 35 (Scheme 12), an antithrombotic compound with other well-defined physiological properties, is formed from allicin.84 Like allicin, ajoene is a sulfoxide but has two further sulfur atoms in a disulfide linkage. E and Z isomeric forms are possible involving the C=C bond at positions 6 and 7. Ajoene is somewhat more stable than allicin. The formation of ajoene probably involves condensation of 2 molecules of allicin forming a sulfonium salt 33, with elimination of propenesulfenic acid. Elimination of a second molecule of propenesulfenic acid... 

Ajoene has antitumor activity, inhibits cholesterol biosynthesis, modulates membrane-dependent functions of immune cells, inhibits protein prenylation83 and is an anti-leukaemia agent for acute myeloid leukaemia.85 In antithrombotic assays, the Z isomer is more active than the E isomer.84... 

However, the most interesting molecule is ajoene, which is derived from garlic when it is cooked, particularly under slightly acidic conditions such as in tomato sauce ... 

Ajoene is formed from three molecules of allicin and is responsible in part for the... 

During the early part of my scientihc work, I spent 17 years as a professor in the Department of Chemistry at Indiana University. During that period, I had, among others, two talented coworkers Mahendra Jain as a post-doctoral fellow and Rafael Apitz-Castro as a visiting professor from the Institute Venezolano de Investigaciones Cientificas (IVIC) in Caracas, Venezuela. These two former coworkers did the most important work on ajoene. It is always great to see former colleagues go on to do important work. 

Garlic clearly has antithrombotic properties. Ajoene (an allicin metabolite) and methyl allyl trisulfide inhibit platelet aggregation. Garlic may promote vasodilation by relaxing smooth muscle, and it may reduce low-density lipoprotein (LDL) oxidation. 

N.A. Alliin, iodine, diallyl trisulfide, 2-vinyl-4h-l,3-dithin, ajoene, linoleic acid, diallyl disulfide, scordinins, selenium.98 99 107 511 Reduce serum cholesterol, lower blood pressure, and platelet aggregation. It is anticancer, antimicrobial, antithrombotic. 

Ajoene Allium sativum, A. Jistu/osum, A. tuberosum... 

Ajoene, Fig. (10), an unsaturated sulfoxide disulfide, is the principal chemical responsible for garlic s anticoagulant properties. It has been also investigated for its acaricidal activity on T. urticae [275]. Complete mortality (100%) by ajoene was observed at 0.075% after 14 h of treatment, a dose comparable with other synthetic acaricides used in the experiment. At lower concentrations (0.05%), it affected female fecundity... 

Garlic is used for a variety of reasons, and some of the attributes associated with it, e.g. for cancer prevention, or to reduce heart attacks, may not be substantiated. Other properties such as antimicrobial activity, effects on lipid metabolism, and platelet aggregation inhibitory action have been demonstrated. Ajoene has been shown to be a potent antithrombotic agent through inhibition of platelet aggregation. 

A number of studies have focused on identifying the active antimicrobial principles in fresh garlic extract. Allicin has been identified as the active agent in garlic extracts. The antifungal activity of allicin has been shown to depend on the sulfhydryl moiety because activity is destroyed by thiols such as L-cysteine, glutathione, and mercaptoethanol. Ajoene, a compound found in oil-macerated garlic, has also been shown to have antimicrobial activity (Ali et al., 2000). 

Alkyl sulfides and thiols. Some alkyl thiols and sulfides, notably those from commonly ingested Allium sativum (garlic) and Allium cepa (onion) (Alliaceae), are variously bioactive as odorants and antimicrobials. Propanethial S-oxide (CH3-CH2-CH=S=0) is a lachrymatory irritant principle of onion. Allicin (S-oxodiallydisulfide CH2=CH—CH2-SO-S-CH2— CH=CH2), diallyldisulfide (CH2=CH-CH2-S-S-CH2-CH=CH2) and diallylsulfide (CH2=CH—CH2—S—CH2-CH=CH2) are major odorants of garlic that are reactive and irritant because of the allyl groups. Dimethyl disulfide (CH3—S—S-CH3), dipropyl disulfide (CH3-CH2-CH2-S-S-CH2-CH2-CH3), methyl allyl disulfide (CH3-S-S-CH2-CH=CH2) and propane-1-thiol (CH3-CH2—CH2—SH) are further Allium odorants. Methane thiol (methyl mercaptan CH3—SH) is a widespread plant volatile and notably derives from anaerobic bacterial degradation of cysteine as in human flatus and bad mouth odour. The aliphatic disulfides allicin and ajoene inhibit proinflammatory expression of iNOS. 

Ajoene Allium sativum (garlic) (Alliaceae) Apoptotic (caspase 3... 

---