A nonvolatile and slightly water-soluble antimicrobial sulfur compound newly isolated from heated garlic extract was characterized. The compound was generated most when heated at 120°C for 30 minutes and completely disappeared after 90 minutes of heating. It has a molecular mass of 225 daltons with an elemental ratio of C6H11N1O2S3, and the interpretation of 1H- and 13C-nuclear magnetic resonance and Fourier transform-infrared data showed that the compound was CH2 = CH-CH2-S-S-S-CH2-CH(NH2)COOH, 3-(allyltrisulfanyl)-2-aminopropanoic acid, a derivative of cysteine, presumably derived from alliin (S-allyl-l-cysteine sulfoxide). This novel compound has comparatively potent anti-yeast activity and rather weak antibacterial activity, similar to other antimicrobial compounds in garlic.
Get full access to this article
View all access options for this article.
References
1.
StollA, SeebeckE. Chemical investigation of alliin, the specific principle of garlic. Adv Enzymol, 1951; 11:377–400.
2.
LawsonLD. The composition and chemistry of garlic cloves and processed garlic. Garlic. The Science and Therapeutic Application of Allium sativum L. and Related Species. KochHP, LawsonLD. Williams & Wilkins: Baltimore, 1996; 37–107.
3.
KyungKH, KimMH, ParkMS, KimYS. Alliinase-independent inhibition of Staphylococcus aureus B33 by heated garlic. J Food Sci, 2002; 67:780–785.
4.
ChoiJH, KyungKH. Allyl alcohol is the sole antiyeast compound in heated garlic extract. J Food Sci, 2005; 70:305–309.
5.
KimEH, ChungIS, KyungKH. Antimicrobial activity of garlic extract heated under different conditions, time of heating and pH. Food Sci Biotechnol, 2009; 18:771–775.
6.
KimJW, HuhJE, KyungSH, KyungKH. Antimicrobial activity of alk(en)yl sulfides found in essential oils of garlic and onion. Food Sci Biotechnol, 2004; 13:235–239.
7.
ChungI, ChaeKY, KyungKH. Thermal generation and antimicrobial activity of unusual heterocyclic sulfur compounds in garlic. Food Sci Biotechnol, 2008; 17:1032–1037.
8.
FeraryS, ThibotE, AugerJ. Direct analysis of odors emitted by freshly cut Allium using combined high-performance liquid chromatography and mass spectrometry. Rapid Commun Mass Spectrom, 1996; 10:1327–1332.
9.
SundaresanS, SubramanianP. Prevention of N-nitrosodiethylamine-induced hepatocarcinogenesis by S-allylcysteine. Mol Cell Biochem, 2008; 310:209–214.
10.
HowardEW, LingM-T, ChuaCW, CheungHW, WangX, WongYC. Garlic-derived S-allylmercaptocysteine is a novel in vivo antimetastatic agent for androgen-independent prostate cancer. Clin Cancer Res, 2007; 13:1847–1856.
11.
ShirinH, PintoJT, KawabataY, SohJ-W, DeloheryT, MossSF, MurtyV, RivlinRS, HoltPR, WeinsteinIB. Antiproliferative effects of S-allylmercaptocysteine on colon cancer cells when tested alone or in combination with sulindac sulfide. Cancer Res, 2001; 61:725–731.
12.
NakagawaS, KasugaS, MatsuuraH. Prevention of liver damage by aged garlic extract and its components in mice. Phytother Res, 1989; 3:50–53.
13.
PintoJT, RivlinRS. Antiproliferative effects of Allium derivatives from garlic. J Nutr, 2001; 131,3S:1058S–1060S.
14.
ChuQ, LeeDTW, TsaoSW, WangX, WongYC. S-Allylcysteine, a water-soluble garlic derivative, suppresses the growth of a human androgen-independent prostate cancer xerograft, CWR22R, under in vivo conditions. BJU Int, 2006; 99:925–932.
15.
PintoJT, QiaoC, XingJ, RivlinRS, ProtomacastroML, WeisslerML, TaoY, ThalerH, HestonWDW. Effects of garlic thioallyl derivatives on growth, glutathione concentration, and polyamine formation of human prostate carcinoma cells in culture. Am J Clin Nutr, 1997; 66:398–405.
16.
XiaoDX, PintoJT, SohJW, DeguchiA, GundersenGG, PalazzoAF, YoonJT, ShirinH, WeinsteinIB. Induction of apoptosis by the garlic-derived compound S-allylmercaptocysteine (SAMC) is associated with microtubule depolymerization and c-Jun NH2-terminal kinase 1 activation. Cancer Res, 2003; 63:6825–6837.
17.
Pedraza-ChaverríJ, BarreraD, MaldonadoPD, ChirinoYI, Macías-RuvalcabaN, Medina-CamposON, CastroL, SalcedoMI, Hernández-PandoR. S-Allylmercaptocysteine scavenges hydroxyl radical and singlet oxygen in vitro and attenuates gentamicin-induced oxidative and nitrosative stress and renal damage in vivo. BMC Clin Pharmacol, 2004; 4:5.
18.
Medina-CamposON, BarreraD, Segoviano-MurilloS, RochaD, MaldonadoPD, Mendoza-PatinoN, Pedraza-ChaverriJ. S-Allylcysteine scavenges singlet oxygen and hypochlorous acid and protects LLC-PK1 cells of potassium dichromate-induced toxicity. Food Chem Toxicol, 2007; 45:2030–2039.
19.
Pérez-SererianoF, Salvatierra-SánchezR, Rodríguez-PérezM, Cuevas-MartínezEY, GuevaraJ, LimónD, MaldonadoPD, Medina-CamposON, Pedraza-ChaverríJ, SantamaríaA. S-Allylcysteine prevents amyloid-β peptide-induced oxidative stress in rat hippocampus and ameliorates learning deficits. Eur J Pharmacol, 2004; 489:197–202.
20.
HatonoS, JimenezA, WargovichM. Chemopreventive effect of S-allylcysteine and its relationship to the detoxification enzyme glutathione S-transferase. Carcinogenesis, 1996; 17:1041–1044.
21.
CavallitoCJ, BuckJS, SuterCM. Allicin, the antibacterial principle of Allium sativum. II. Determination of the chemical structure. J Am Chem Soc, 1944; 66:1952–1954.
CavallitoCJ, BaileyJH. Allicin, the antibacterial principle of Allium sativum. I. Isolation, physical properties and antimicrobial action. J Am Chem Soc, 1944; 66:1950–1951.
24.
KyungKH, FlemingHP. S-Methyl-l-cysteine sulfoxide as the precursor of methyl methanethiosulfinate, the principal antibacterial compound in cabbage. J Food Sci, 1994; 59:350–355.
25.
HagemanGJ, van HerwinenMH, SchildermanPA, RhijnsburgerEH, MoonenEJ, KleinjansJC. Reducing effects of garlic constituents on DNA adduct formation in human lymphocytes in vitro. Nutr Cancer, 1997; 27:177–185.
26.
PeteschBL, SumiyoshiH. Recent advances on the nutritional benefits accompanying the use of garlic as a supplement. Trends Food Sci Technol, 1999; 9:415–418.
