|
1
|
Lancaster JE and Show ML: γ-Glutamyl
peptides in the biosynthesis of S-alk(en)yl-L-cysteine
sulphoxides (flavor precursors) in Allium. Phytochemistry.
28:455–460. 1989. View Article : Google Scholar
|
|
2
|
Yoshimoto N, Yabe A, Sugino Y, Murakami S,
Sai-Ngam N, Sumi S, Tsuneyoshi T and Saito K: Garlic γ-glutamyl
transpeptidases that catalyze deglutamylation of biosynthetic
intermediate of alliin. Front Plant Sci. 5:7582015. View Article : Google Scholar : PubMed/NCBI
|
|
3
|
Yoshimoto N, Onuma M, Mizuno S, Sugino Y,
Nakabayashi R, Imai S, Tsuneyoshi T, Sumi S and Saito K:
Identification of a flavin-containing S-oxygenating
monooxygenase involved in alliin biosynthesis in garlic. Plant J.
83:941–951. 2015. View Article : Google Scholar : PubMed/NCBI
|
|
4
|
Matsuura H, Inagaki M, Maeshiga K, Ide N,
Kajimura Y and Itakura Y: Changes in contents of γ-glutamyl
peptides and fructan during growth of Allium sativum. Platna
Med. 62:70–71. 1996. View Article : Google Scholar
|
|
5
|
Block E: The chemistry of garlic and
onions. Sci Am. 252:114–119. 1985. View Article : Google Scholar : PubMed/NCBI
|
|
6
|
Kodera Y, Ushijima M, Amano H, Suzuki JI
and Matsutomo T: Chemical and Biological Properties of
S−1-Propenyl-L-Cysteine in Aged Garlic Extract. Molecules.
22:E5702017. View Article : Google Scholar : PubMed/NCBI
|
|
7
|
Block E: The organosulfur chemistry of the
genus Allium-implication for organic sulfur chemistry. Angew
Chem Int Ed Engl. 31:1135–1178. 1992. View Article : Google Scholar
|
|
8
|
Kimura S, Tung YC, Pan MH, Su NW, Lai YJ
and Cheng KC: Black garlic: A critical review of its production,
bioactivity and application. Yao Wu Shi Pin Fen Xi. 25:62–70.
2017.
|
|
9
|
Martínez-Casas L, Lage-Yusty M and
López-Hernández J: Changes in aromatic profile, sugars and
bioactive compounds when purple garlic is transformed into black
garlic. J Agric Food Chem. 65:10804–10811. 2017. View Article : Google Scholar : PubMed/NCBI
|
|
10
|
Kodera Y, Matsuura H, Sumiyoshi H and Sumi
SI: Chapter 30. Garlic Chemistry: chemical and biological
properties of sulfur-containing compounds derived from garlic. ACS
symposium series 851, Food Factors in Health Promotion and Disease
Prevention. Shahadi F, Ho CT, Watanabe S and Osawa T: American
Chemical Society; Washington DC: pp. 346–357. 2003, View Article : Google Scholar
|
|
11
|
Ryu K, Ide N, Matsuura H and Itakura I:
Nα-(1-deoxy-D-fructos-1-yl)-L-arginine, an antioxidant
compound identified in aged garlic extract. J Nutr. 136 (Suppl
3):972S–976S. 2006.
|
|
12
|
Matsutomo T, Stark TD and Hofmann T: In
vitro activity-guided identification of antioxidants in aged garlic
extract. J Agric Food Chem. 61:3059–3067. 2013. View Article : Google Scholar : PubMed/NCBI
|
|
13
|
Koch HP and Lawson LD: Garlic: The science
and therapeutic application of Allium Sativum L and related
species. Williams & Wilkins; 1996
|
|
14
|
Ichikawa M, Ide N and Ono K: Changes in
organosulfur compounds in garlic cloves during storage. J Agric
Food Chem. 54:4849–4854. 2006. View Article : Google Scholar : PubMed/NCBI
|
|
15
|
Sun Y, Hu J, Wang W, Zhang B and Shen Y:
Characterization of γ-glutamyltranspeptidases from dormant garlic
and onion bulbs. Food Sci Nutr. 7:499–505. 2019. View Article : Google Scholar : PubMed/NCBI
|
|
16
|
Amano H, Kazamori D, Itoh K and Kodera Y:
Metabolism, excretion, and pharmacokinetics of
S-allyl-L-cysteine in rats and dogs. Drug Metab Dispos.
43:749–755. 2015. View Article : Google Scholar : PubMed/NCBI
|
|
17
|
Amano H, Kazamori D and Itoh K:
Pharmacokinetics and N-acetylation metabolism of
S-methyl-L-cysteine and trans-S−1-propenyl-L-cysteine
in rats and dogs. Xenobiotica. 46:1017–1025. 2016. View Article : Google Scholar : PubMed/NCBI
|
|
18
|
Amano H, Kazamori D and Itoh K: Evaluation
of the effects of S-allyl-L-cysteine,
S-methyl-L-cysteine, trans-S−1-propenyl-L-cysteine,
amd their N-acetylated and S-oxidized metabolites on
human CYP activities. Biol Pharm Bull. 39:1701–1707. 2016.
View Article : Google Scholar : PubMed/NCBI
|
|
19
|
Amagase H: Clarifying the real bioactive
constituents of garlic. J Nutr. 136 (Suppl 3):716S–725S. 2006.
View Article : Google Scholar : PubMed/NCBI
|
|
20
|
Colín-González AL, Santana RA, Silva-Islas
CA, Chánez-Cárdenas ME, Santamaría A and Maldonado PD: The
antioxidant mechanisms underlying the aged garlic extract- and
S-allylcysteine-induced protection. Oxid Med Cell Longev.
2012:9071622012. View Article : Google Scholar : PubMed/NCBI
|
|
21
|
Fukushima S, Takada N, Wanibuchi H, Hori
T, Min W and Ogawa M: Suppression of chemical carcinogenesis by
water-soluble organosulfur compounds. J Nutr. 136 (Suppl
3):1049S–1053S. 2006.
|
|
22
|
Suzuki J, Yamaguchi T, Natsutomo T, Amano
H, Morihara N and Kodera Y: S−1-Propenylcysteine promotes
the differentiation of B cell into IgA-producing cells by the
induction of Erk1/2-dependent Xbp1 expression in Peyer's patches.
Nutrition. 32:884–889. 2016. View Article : Google Scholar : PubMed/NCBI
|
|
23
|
Suzuki JI, Kodera Y, Miki S, Ushijima M,
Takashima M, Matsutomo T and Morihara N: Anti-inflammatory action
of cysteine derivative S−1-propenylcysteine by inducing
MyD88 degradation. Sci Rep. 8:141482018. View Article : Google Scholar : PubMed/NCBI
|
|
24
|
Matsutomo T, Ushijima M, Kodera Y,
Nakamoto M, Takashima M, Morihara N and Tamura K: Metabolomic study
on the antihypertensive effect of S−1-propenylcysteine in
spontaneously hypertensive rats using liquid chromatography coupled
with quadrupole-Orbitrap mass spectrometry. J Chromatogr B Analyt
Technol Biomed Life Sci. 1046:147–155. 2017. View Article : Google Scholar : PubMed/NCBI
|
|
25
|
Pushpendran CK, Devasagayam TP, Chintalwar
GJ, Banerji A and Eapen J: The metabolic fate of [35S]-diallyl
disulphide in mice. Experientia. 36:1000–1001. 1980. View Article : Google Scholar : PubMed/NCBI
|
|
26
|
Lawson LD and Wang ZJ: Pre-hepatic fate of
the organosulfur compounds derived from garlic (Allim
sativum). Planta Med. 59:688A–689A. 1993. View Article : Google Scholar
|
|
27
|
Freeman F and Kodera Y: Garlic chemistry:
Stability of S-(2-propyl) 2-propen-1-sulfinothioate
(allicin) in blood, solvents, and stimulated physiological fluids.
J Agric Food Chem. 43:2332–2338. 1995. View Article : Google Scholar
|
|
28
|
Amagase H, Petesch BL, Matsuura H, Kasuga
S and Itakura Y: Intake of garlic and its bioactive components. J
Nutr. 131 (Suppl 3):955S–962S. 2001. View Article : Google Scholar : PubMed/NCBI
|
|
29
|
Sugii M, Suzuki T and Nagasawa S:
Isolation of (−)S-propenyl-L-cysteiene from garlic. Chem
Abstr. 59:65091963.
|
|
30
|
Matsutomo T and Kodera Y: Development of
an analytical method for sulfur compounds in aged garlic extract
with the use of a post-column high performance liquid
chromatography method with sulfur-specific detection. J Nutr.
146:450S–455S. 2016. View Article : Google Scholar : PubMed/NCBI
|
|
31
|
Kodera Y, Matsutomo T and Itoh K: The
evidence for the production mechanism of
cis-S−1-propenylcysteine in aged garlic extract based on a
model reaction approach using its isomers and deuterated solvents.
Planta Med Lett. 2:e69–e72. 2015. View Article : Google Scholar
|
|
32
|
Oae S, Tamagaki S and Kunieda N:
Stereoelectronic effect of sulfur group. Organic Sulfur Chemistry.
Oae S: Kagakudojin; Kyoto: pp. 41–81. 1982
|
|
33
|
Oae S, Ohno A and Tagaki W: Acid-catalyzed
hydrogen-deuterium exchange reaction of deuterated anisole,
thioanisole and benzene. Bull Chem Soc Jpn. 35:681–683. 1962.
View Article : Google Scholar
|
|
34
|
Nakamoto M, Fujii T, Matsutomo T and
Kodera Y: Isolation and identification of three γ-glutamyl
tripeptides and their putative production mechanism in aged garlic
extract. J Agric Food Chem. 66:2891–2899. 2018. View Article : Google Scholar : PubMed/NCBI
|
|
35
|
Kasai T, Shiroshita Y and Sakamura S:
γ-Glutamyl peptides of Vigna radiata seeds. Phytochemistry.
25:679–682. 1986. View Article : Google Scholar
|
|
36
|
Albrecht F, Leontiev R, Jacob C and
Slusarenko AJ: An optimized facile procedure to synthesize and
purify allicin. Molecules. 22:7702017. View Article : Google Scholar
|
|
37
|
Fujii T, Matsutomo T and Kodera Y: Changes
of S-allylmercaptocysteine and
γ-glutamyl-S-allylmercaptocysteine contents and their
putative production mechanisms in garlic extract during the aging
process. J Agric Food Chem. 66:10506–10512. 2018. View Article : Google Scholar : PubMed/NCBI
|
|
38
|
Sumioka I, Matsura T and Yamada K:
Therapeutic effect of S-allylmercaptocysteine on
acetaminophen-induced liver injury in mice. Eur J Pharmacol.
433:177–185. 2001. View Article : Google Scholar : PubMed/NCBI
|
|
39
|
Xiao J, Guo R, Fung ML, Liong EC, Chang
RC, Ching YP and Tipoe GL: Garlic-derived
S-allylmercaptocysteine ameliorates nonalcoholic fatty liver
disease in a rat model through inhibition of apoptosis and
enhancing autophagy. Evid Based Complement Alternat Med.
2013:6429202013. View Article : Google Scholar : PubMed/NCBI
|
|
40
|
Uzun L, Kokten N, Cam OH, Kalcioglu MT,
Ugur MB, Tekin M and Acar GO: The effect of garlic derivatives
(S-allylmercaptocysteine, diallyl disulfide, and
S-allylcysteine) on gentamicin induced ototoxicity: An
experimental study. Clin Exp Otorhinolaryngol. 9:309–313. 2016.
View Article : Google Scholar : PubMed/NCBI
|
|
41
|
Zhu X, Jiang X, Li A, Sun Y, Liu Y, Sun X,
Feng X, Li S and Zhao Z: S-Allylmercaptocysteine suppresses
the growth of human gastric cancer xenografts through induction of
apoptosis and regulation of MAPK and PI3K/Akt signaling pathways.
Biochem Biophys Res Commun. 491:821–826. 2017. View Article : Google Scholar : PubMed/NCBI
|
|
42
|
Yang M, Dong Z, Jiang X, Zhao Z, Zhang J,
Cao X and Zhang D: Determination of S-allylmercaptocysteine
in rat plasma by LC-MS/MS and its application to a pharmacokinetics
study. J Chromatogr Sci. 56:396–402. 2018. View Article : Google Scholar
|
|
43
|
Block E: Garlic and Other Alliums: The
Lore and the Science. The Royal Society of Chemistry; Cambridge:
2010
|
|
44
|
Rizzi GP: The Maillard Reaction in Foods.
Maillard Reactions in Chemistry, Food, and Health. Labuza TP,
Reineccius GA, Monnier VM and Baynes JW: The Royal Society of
Chemistry; Cambridge: pp. 11–19. 1994
|
|
45
|
Matsutomo T, Stark TD and Hofmann T:
Targeted screening and quantitative analyses of antioxidant
compounds in aged-garlic extract. Eur Food Res Technol.
244:1803–1814. 2018. View Article : Google Scholar
|
|
46
|
Ide N, Ichikawa M, Ryu K, Yoshida J,
Sasaoka T, Sumi S and Sumiyoshi H: Chapter 22. Antioxidants in
processed garlic: Tetrahydro-β-carboline derivatives in aged garlic
extract. ACS Symposium Series 851. Food Factors in Health Promotion
and Disease Prevention. Shahidi F, Ho CT, Watanabe S and Osawa T:
American Chemical Society; Washington, DC: pp. 250–263. 2003,
View Article : Google Scholar
|
|
47
|
Imai J, Ide N, Nagae S, Moriguchi T,
Matsuura H and Itakura Y: Antioxidant and radical scavenging
effects of aged garlic extract and its constituents. Planta Med.
60:417–420. 1994. View Article : Google Scholar : PubMed/NCBI
|
|
48
|
Zhou H, Qu Z, Mossine VV, Nknolise DL, Li
J, Chen Z, Cheng J, Greenlief CM, Mawhinney TP, Brown PN, et al:
Proteomic analysis of the effects of aged garlic extract and its
FruArg component on lipopolysaccharide-induced neuroinflammatory
response in microglial cells. PLoS One. 9:e1135312014. View Article : Google Scholar : PubMed/NCBI
|
|
49
|
Fenwick TE and Hanley AB: Critical review
in food science and nutrition. The genus Allium. Part 2.
Furia TE: CRC Press; Boca Raton, FL: pp. p2841985
|
|
50
|
Darbyshire B and Henry RJ: Differences in
fructan content and synthesis in some Allium species. New Phytol.
87:249–256. 1981. View Article : Google Scholar
|
|
51
|
Ohsumi C and Hayashi T: The
oligosaccharide unit of xyloglucan in the cell wall of bulbs of
onion, garlic, and their hybrid. Plant Cell Physiol. 35:963–967.
1994.PubMed/NCBI
|
|
52
|
Kang OJ: Physicochemical Characteristics
of Black Garlic after Different Thermal Processing Steps. Prev Nutr
Food Sci. 21:348–354. 2016. View Article : Google Scholar : PubMed/NCBI
|
|
53
|
Smoczkiewicz MA, Nitschke D and Wieladek
H: Microdetermination of steroid and triterpene saponin glycosides
in various plant materials I. Allium species. Mikrochim Acta.
78:43–53. 1982. View Article : Google Scholar
|
|
54
|
Matsuura H, Ushiroguchi T, Itakura Y,
Hayashi N and Fuwa T: A frostanol glycoside from garlic, bulbs of
Allium sativum L. Chem Pharm Bull (Tokyo). 36:3659–3663.
1988. View Article : Google Scholar
|
|
55
|
Matsuura H, Ushiroguchi T, Itakura Y and
Fuwa T: Further studies on steroidal glycosides from bulbs, root
and leaves of Allium sativum L. Chem Pharm Bull (Tokyo).
37:2741–2743. 1989. View Article : Google Scholar
|
|
56
|
Matsuura H: Phytochemistry of garlic
horticultural and processing procedures. Neutraceuticals: Designer
Foods III. Garlic, Soy and Licorice. Lachance PA: Food and
Nutrition Press; Trumbull, CT: pp. 55–69. 1997
|
|
57
|
Peng JP, Chen H, Qiao YQ, Ma LR, Narui T,
Suzuki H, Okuyama T and Kobayashi H: Two new steroidal saponins
from Allium sativum and their inhibitory effects on blood
coagulability. Yao Xue Xue Bao. 31:607–612. 1996.PubMed/NCBI
|
|
58
|
Slowing K, Ganado P, Sanz M, Ruiz E,
Beecher C and Tejerina T: Study of garlic extract and fractions on
cholesterol plasma levels and vascular reactivity in
cholesterol-fed rats. J Nutr. 131 (Suppl 3):994S–999S. 2001.
View Article : Google Scholar : PubMed/NCBI
|
|
59
|
Itakura Y, Ichikawa M, Mori Y, Okino R,
Udayama M and Morita T: How to distinguish garlic from other Allium
vegetables. J Nutr. 131 (Suppl 3):963S–967S. 2001. View Article : Google Scholar : PubMed/NCBI
|
|
60
|
Kang SS, Lim DR and Kyung KH:
3-(Allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile
water-soluble antimicrobial sulfur compound in heated garlic. J Med
Food. 13:1247–1253. 2010. View Article : Google Scholar : PubMed/NCBI
|
|
61
|
Rabinkov A, Miron T, Mirelman D, Wilchek
M, Glozman S, Yavin E and Weiner L:
S-Allylmercaptoglutathione: The reaction product of allicin
with glutathione possesses SH-modifying and antioxidant properties.
Biochim Biophys Acta. 1499:144–153. 2000. View Article : Google Scholar : PubMed/NCBI
|
|
62
|
Ban JO, Yuk DY, Woo KS, Kim TM, Lee US,
Jeong HS, Kim DJ, Chung YB, Hwang BY, Oh KW and Hong JT: Inhibition
of cell growth and induction of apoptosis via inactivation of
NF-kappaB by a sulfurcompound isolated from garlic in human colon
cancer cells. J Pharmacol Sci. 104:374–383. 2007. View Article : Google Scholar : PubMed/NCBI
|
|
63
|
Furusawa R, Goto C, Satoh M, Nomi Y and
Murata M: Formation and distribution of
2,4-dihydroxy-2,5-dimethyl-3(2H)-thiophenone, a pigment, an
aroma and a biologically active compound formed by the Maillard
reaction, in foods and beverages. Food Funct. 4:1076–1081. 2013.
View Article : Google Scholar : PubMed/NCBI
|
|
64
|
Yamakawa T, Matsutomo T, Hofmann T and
Kodera Y: Aged garlic extract and one of the constituent,
(+)-(2S,3R)-dehydrodiconiferyl alcohol, inhibits alkaline
phosphatase activity induced by inflammation factors in human
vascular smooth muscle cells. Food Nutr Sci. 5:177–184. 2014.
|
|
65
|
Ichikawa M, Ryu K, Yoshida J, Ide N,
Kodera Y, Sasaoka T and Rosen RT: Identification of six
phenylpropanoids from garlic skin as major antioxidants. J Agric
Food Chem. 51:7313–7317. 2003. View Article : Google Scholar : PubMed/NCBI
|
|
66
|
Kodera Y, Matsuura H, Yoshida S, Sumida T,
Itakura Y, Fuwa T and Nishino H: Allixin, a stress compound from
garlic. Chem Pharm Bull (Tokyo). 37:1656–1658. 1989. View Article : Google Scholar
|
|
67
|
Kodera Y, Ayaba M, Ogasawara K and Ono K:
Allixin induction and accumulation by light irradiation. Chem Pharm
Bull (Tokyo). 49:1636–1637. 2001. View Article : Google Scholar : PubMed/NCBI
|
|
68
|
Kodera Y, Ayaba M, Ogasawara K, Yoshida S,
Hayashi N and Ono K: Allixin accumulation with long-term storage of
garlic. Chem Pharm Bull (Tokyo). 50:405–407. 2002. View Article : Google Scholar : PubMed/NCBI
|
|
69
|
Nishino H, Nishino A, Takayasu J, Iwashima
A, Itakura Y, Kodera Y, Matsuura H and Fuwa T: Antitumor-promoting
activity of allixin, a stress compound produced by garlic. Cancer
J. 3:20–21. 1990.
|
|
70
|
Moriguchi T, Matsuura H, Itakura Y,
Katsuki H, Saito H and Nishiyama N: Allixin, a phytoalexin produced
by garlic, and its analogues as novel exogenous substances with
neurotrophic activity. Life Sci. 61:1413–1420. 1997. View Article : Google Scholar : PubMed/NCBI
|
