大蒜素

大蒜素
	IUPAC名; 2-propene-1-sulfinothioic acid S-2-propenyl ester
英文名	Allicin
别名	蒜辣素；蒜素；大蒜辣素；二烯丙基二硫-氧[S]化合物；大蒜新素
识别
CAS号	539-86-6
PubChem	65036
ChemSpider	58548
SMILES	C=CCS(=O)SCC=C;
InChI	1/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2;
InChIKey	JDLKFOPOAOFWQN-UHFFFAOYAO
Beilstein	1752823
EINECS	208-727-7
ChEBI	28411
KEGG	C07600
MeSH	Allicin
IUPHAR配体	2419
性质
化学式	C6H10OS2
摩尔质量	162.28 g·mol⁻¹
密度	1.112 g/cm3（20/4℃）
熔点	＜25 °C
沸点	80～85 °C（0.2kPa，分解）
折光度n; D	1.561
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

大蒜素（英语：Allicin）是从石蒜科^[1]葱亚科葱属植物大蒜（Allium Sativum）的鳞茎（大蒜头）中提取的一种有机硫化合物，也存在于洋葱和其他葱科植物中。^[2] 学名“二烯丙基硫代亚磺酸酯”（CH₂=CH-CH₂-S(=O)-S-CH₂-CH=CH₂）^[3]^[2]^[4]^[5]，硫代亚磺酸（英语：Thiosulfinate）（R-S(=O)-S-R）一族。

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性质

大蒜素为淡黄色油状液体。具有强烈的大蒜臭、味辣。不溶于水，与乙醇、乙醚、苯、氯仿互溶。水溶液呈微酸性。对酸稳定，对热碱不稳定。蒸馏时分解。静置时有油状沉淀物产生。不稳定，23°C时可在16小时内分解。^[6]

生产

一般从大蒜的鳞茎（大蒜头）中提取，也可通过化学方法合成。用间氯过氧苯甲酸氧化二烯丙基二硫醚可得外消旋大蒜素。^[7]

1944年首先由 Cavallito 分离出来。^[8]

产生

一般认为，大蒜素的产生过程是大蒜粉碎后它所含的不稳定的蒜氨酸（1）经蒜氨酶分解为烯丙次磺酸（2）和脱氢丙氨酸（3），

然后不稳定的脱氢丙氨酸（3）立即分解为丙酮酸和氨，而两分子烯丙次磺酸（2）则歧化为烯丙亚磺酸（4）与烯丙硫醇（5），它们继续失水生成大蒜素（6）：^[9]

大蒜形成风味的机理与葱头十分相似，但粉碎过程中不会生成具有催泪性的中间体硫丙醛-S-氧化物。大蒜素对昆虫和微生物有一定的毒性，它的产生是大蒜抵挡昆虫进攻的自我防御机制。^[10]

分解

大蒜素遇热分解为烯丙次磺酸（3）和烯丙硫醛（7），后者在常温下发生Diels-Alder反应，二聚成3-乙烯基-1,2-二硫杂-5-环己烯（8）和2-乙烯基-1,3-二硫杂-5-环己烯（9）等。^[11]

大蒜素在水和油介质中的分解产物有二烯丙基硫醚（包括二烯丙基一硫醚、二烯丙基二硫醚、二烯丙基三硫醚、二烯丙基四硫醚等）、乙烯基二噻己烯和阿藿烯（英语：Ajoene）等：^[12]

代谢

在体内很快被吸收。在血液中分解为烯丙硫醇（Allyl mercaptan）（2）。后被S-腺苷甲硫氨酸甲基化为甲基烯丙基硫醚（3），从肺中排出。

一般认为大部分烯丙硫醇会被氧化为烯丙磺酸，类似于从半胱氨酸到牛磺酸的转化过程。^[12]

功效

一些动物试验和体外试验表明大蒜素有抗菌（页面存档备份，存于互联网档案馆）^[13]、抗真菌^[8]、消炎、抗氧化^[14]^[15]^[16]、抗血栓^[17]、降血压^[18]^[19]、维持脂蛋白平衡、防治动脉硬化^[20]^[21] 等功效。

一个2007年的临床试验结果是，对于胆固醇水平较高的病人，大蒜素不能降低血液胆固醇浓度。^[22]

2009年，Vaidya、Ingold 和 Pratt 的研究表明大蒜素的生物功效主要是由大蒜素分解产生的2-丙烯次磺酸造成的，该化合物不稳定，很快便与体内的自由基发生反应使之失活。^[23]

用途

提纯的大蒜素可用作抗菌药、饲料添加剂、杀虫剂和杀菌剂。^[24]

参见

二烯丙基二硫
二烯丙基三硫（大蒜新素）

参考资料

[1]
https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1095-8339.2009.00996.x （页面存档备份，存于互联网档案馆） 2009年蒜隶属的葱亚科由《被子植物APG III分类法》并入石蒜科中，已不再属于百合科。
[2]
Eric Block. The chemistry of garlic and onions. Scientific American. 1985, 252 (March): 114–9. PMID 3975593. doi:10.1038/scientificamerican0385-114.
[3]
An Introduction to Organosulfur Chemistry, R. J. Cremlyn, John Wiley and Sons: Chichester (1996). ISBN 0471955124.
[4]
Eric Block, "Garlic and Other Alliums: The Lore and the Science" (Cambridge: Royal Society of Chemistry, 2010)
[5]
Cremlyn, R. J. W. An introduction to organosulfur chemistry. Wiley. 1996. ISBN 0-471-95512-4.
[6]
Hahn, G; in Koch HP, Lawson LD, eds. Garlic: the science and therapeutic application of Allium sativum L and related species (2nd edn). Baltimore: Williams and Wilkins. 1996: 1–24.
[7]
R. J. Cremlyn. An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. 1996. ISBN 0-471-95512-4.
[8]
Chester J. Cavallito, John Hays Bailey. Allicin, the Antibacterial Principle of Allium sativum. I. Isolation, Physical Properties and Antibacterial Action. J. Am. Chem. Soc. 1944, 66 (11): 1950–1951. doi:10.1021/ja01239a048.
[9]
A. Stoll, E. Seebeck. Über den enzymatischen Abbau des Alliins und die Eigenschaften der Alliinase. 2. Mitteilung über Allium-Substanzen. Helv. Chim. Acta. 1949, 32 (1): 197–205. doi:10.1002/hlca.19490320129.
[10]
Allicin. Phytochemicals. [2009-09-05]. （原始内容存档于2009-09-25）.
[11]
Calvey EM, Roach JA, Block E. Supercritical fluid chromatography of garlic (Allium sativum) extracts with mass spectrometric identification of allicin. J. Chromatogr. Sci. 1994, 32 (3): 93–96.
[12]
Theodor Dingermann (Hrsg.), Rudolf Hänsel (Hrsg.) und Ilse Zündorf (Hrsg.): Pharmazeutische Biologie: Molekulare Grundlagen und klinische Anwendungen. Springer Verlag Berlin; 1. Auflage 2002; ISBN 3-540-42844-5; S. 62f.
[13]
Ankri, S; Mirelman D. Antimicrobial properties of allicin from garlic. Microbes Infect. 1999, 2: 125–9.
[14]
U. Sela, S. Ganor, I. Hecht, A. Brill, T. Miron, A. Rabinkov, M. Wilchek, D. Mirelman, O. Lider and R. Hershkoviz. Allicin inhibits SDF-1alpha-induced T cell interactions with fibronectin and endothelial cells by down-regulating cytoskeleton rearrangement, Pyk-2 phosphorylation and VLA-4 expression. Immunology. 2004, 111: 391–399. doi:10.1111/j.0019-2805.2004.01841.x.
[15]
Lindsey J. Macpherson, Bernhard H. Geierstanger, Veena Viswanath, Michael Bandell, Samer R. Eid, SunWook Hwang, and Ardem Patapoutian. The pungency of garlic: Activation of TRPA1 and TRPV1 in response to allicin. Current Biology. 2005, 15 (May 24): 929–934. 外部链接存在于|title= (帮助)
[16]
Bautista DM, Movahed P, Hinman A, Axelsson HE, Sterner O, Hogestatt ED, Julius D, Jordt SE and Zygmunt PM. Pungent products from garlic activate the sensory ion channel TRPA1. Proc Natl Acad Sci USA. 2005, 102 (34): 12248–52. PMID 16103371. doi:10.1073/pnas.0505356102.
[17]
Srivastava KC. Evidence for the mechanism by which garlic inhibits platelet aggregation.. Prostaglandins Leukot Med. 1986, 22(3): 313–321. doi:10.1016/0262-1746(86)90142-3.
[18]
Silagy CA, Neil HA. A meta-analysis of the effect of garlic on blood pressure. J Hypertens. 1994, 12(4): 463–468.
[19]
A. Elkayam, D. Mirelman, E. Peleg, M. Wilchek, T. Miron, A. Rabinkov, M. Oron-Herman and T. Rosenthal. The effects of allicin on weight in fructose-induced hyperinsulinemic, hyperlipidemic, hypertensive rats. Am. J. Hypertens. 2003, 16: 1053–1056. doi:10.1016/j.amjhyper.2003.07.011.
[20]
S. Eilat, Y. Oestraicher, A. Rabinkov, D. Ohad, D. Mirelman, A. Battler, M. Eldar and Z. Vered. Alteration of lipid profile in hyperlipidemic rabbits by allicin, an active constituent of garlic. Coron. Artery Dis. 1995, 6: 985–990.
[21]
D. Abramovitz, S. Gavri, D. Harats, H. Levkovitz, D. Mirelman, T. Miron, S. Eilat-Adar, A. Rabinkov, M. Wilchek, M. Eldar and Z. Vered,. Allicin-induced decrease in formation of fatty streaks (atherosclerosis) in mice fed a cholesterol-rich diet. Coron. Artery Dis. 1999, 10: 515–519. doi:10.1097/00019501-199910000-00012.
[22]
Gardner CD, Lawson LD, Block E; et al. Effect of raw garlic vs commercial garlic supplements on plasma lipid concentrations in adults with moderate hypercholesterolemia: a randomized clinical trial. Arch. Intern. Med. 2007, 167 (4): 346–53. PMID 17325296. doi:10.1001/archinte.167.4.346.
[23]
Vaidya, Vipraja; Keith U. Ingold, Derek A. Pratt. Garlic: Source of the Ultimate Antioxidants - Sulfenic Acids. Angewandte Chemie. 2009, 121 (1): 163–166 [21 Feb 2009]. doi:10.1002/ange.200804560. ^{[永久失效链接]}
[24]
大蒜辣素；蒜素；蒜辣素；大蒜素. 化工引擎. [2009-09-05]. （原始内容存档于2011-02-04）.

[1] [1]
https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1095-8339.2009.00996.x （页面存档备份，存于互联网档案馆） 2009年蒜隶属的葱亚科由《被子植物APG III分类法》并入石蒜科中，已不再属于百合科。

[Eric_Block_1985_114–119-2] [2]
Eric Block. The chemistry of garlic and onions. Scientific American. 1985, 252 (March): 114–9. PMID 3975593. doi:10.1038/scientificamerican0385-114.

[3] [3]
An Introduction to Organosulfur Chemistry, R. J. Cremlyn, John Wiley and Sons: Chichester (1996). ISBN 0471955124.

[eric-4] [4]
Eric Block, "Garlic and Other Alliums: The Lore and the Science" (Cambridge: Royal Society of Chemistry, 2010)

[5] [5]
Cremlyn, R. J. W. An introduction to organosulfur chemistry. Wiley. 1996. ISBN 0-471-95512-4.

[6] [6]
Hahn, G; in Koch HP, Lawson LD, eds. Garlic: the science and therapeutic application of Allium sativum L and related species (2nd edn). Baltimore: Williams and Wilkins. 1996: 1–24.

[7] [7]
R. J. Cremlyn. An Introduction to Organosulfur Chemistry. Chichester: John Wiley and Sons. 1996. ISBN 0-471-95512-4.

[Chester-8] [8]
Chester J. Cavallito, John Hays Bailey. Allicin, the Antibacterial Principle of Allium sativum. I. Isolation, Physical Properties and Antibacterial Action. J. Am. Chem. Soc. 1944, 66 (11): 1950–1951. doi:10.1021/ja01239a048.

[9] [9]
A. Stoll, E. Seebeck. Über den enzymatischen Abbau des Alliins und die Eigenschaften der Alliinase. 2. Mitteilung über Allium-Substanzen. Helv. Chim. Acta. 1949, 32 (1): 197–205. doi:10.1002/hlca.19490320129.

[10] [10]
Allicin. Phytochemicals. [2009-09-05]. （原始内容存档于2009-09-25）.

[11] [11]
Calvey EM, Roach JA, Block E. Supercritical fluid chromatography of garlic (Allium sativum) extracts with mass spectrometric identification of allicin. J. Chromatogr. Sci. 1994, 32 (3): 93–96.

[Dingermann-12] [12]
Theodor Dingermann (Hrsg.), Rudolf Hänsel (Hrsg.) und Ilse Zündorf (Hrsg.): Pharmazeutische Biologie: Molekulare Grundlagen und klinische Anwendungen. Springer Verlag Berlin; 1. Auflage 2002; ISBN 3-540-42844-5; S. 62f.

[13] [13]
Ankri, S; Mirelman D. Antimicrobial properties of allicin from garlic. Microbes Infect. 1999, 2: 125–9.

[14] [14]
U. Sela, S. Ganor, I. Hecht, A. Brill, T. Miron, A. Rabinkov, M. Wilchek, D. Mirelman, O. Lider and R. Hershkoviz. Allicin inhibits SDF-1alpha-induced T cell interactions with fibronectin and endothelial cells by down-regulating cytoskeleton rearrangement, Pyk-2 phosphorylation and VLA-4 expression. Immunology. 2004, 111: 391–399. doi:10.1111/j.0019-2805.2004.01841.x.

[15] [15]
Lindsey J. Macpherson, Bernhard H. Geierstanger, Veena Viswanath, Michael Bandell, Samer R. Eid, SunWook Hwang, and Ardem Patapoutian. The pungency of garlic: Activation of TRPA1 and TRPV1 in response to allicin. Current Biology. 2005, 15 (May 24): 929–934. 外部链接存在于|title= (帮助)

[16] [16]
Bautista DM, Movahed P, Hinman A, Axelsson HE, Sterner O, Hogestatt ED, Julius D, Jordt SE and Zygmunt PM. Pungent products from garlic activate the sensory ion channel TRPA1. Proc Natl Acad Sci USA. 2005, 102 (34): 12248–52. PMID 16103371. doi:10.1073/pnas.0505356102.

[17] [17]
Srivastava KC. Evidence for the mechanism by which garlic inhibits platelet aggregation.. Prostaglandins Leukot Med. 1986, 22(3): 313–321. doi:10.1016/0262-1746(86)90142-3.

[18] [18]
Silagy CA, Neil HA. A meta-analysis of the effect of garlic on blood pressure. J Hypertens. 1994, 12(4): 463–468.

[19] [19]
A. Elkayam, D. Mirelman, E. Peleg, M. Wilchek, T. Miron, A. Rabinkov, M. Oron-Herman and T. Rosenthal. The effects of allicin on weight in fructose-induced hyperinsulinemic, hyperlipidemic, hypertensive rats. Am. J. Hypertens. 2003, 16: 1053–1056. doi:10.1016/j.amjhyper.2003.07.011.

[20] [20]
S. Eilat, Y. Oestraicher, A. Rabinkov, D. Ohad, D. Mirelman, A. Battler, M. Eldar and Z. Vered. Alteration of lipid profile in hyperlipidemic rabbits by allicin, an active constituent of garlic. Coron. Artery Dis. 1995, 6: 985–990.

[21] [21]
D. Abramovitz, S. Gavri, D. Harats, H. Levkovitz, D. Mirelman, T. Miron, S. Eilat-Adar, A. Rabinkov, M. Wilchek, M. Eldar and Z. Vered,. Allicin-induced decrease in formation of fatty streaks (atherosclerosis) in mice fed a cholesterol-rich diet. Coron. Artery Dis. 1999, 10: 515–519. doi:10.1097/00019501-199910000-00012.

[22] [22]
Gardner CD, Lawson LD, Block E; et al. Effect of raw garlic vs commercial garlic supplements on plasma lipid concentrations in adults with moderate hypercholesterolemia: a randomized clinical trial. Arch. Intern. Med. 2007, 167 (4): 346–53. PMID 17325296. doi:10.1001/archinte.167.4.346.

[23] [23]
Vaidya, Vipraja; Keith U. Ingold, Derek A. Pratt. Garlic: Source of the Ultimate Antioxidants - Sulfenic Acids. Angewandte Chemie. 2009, 121 (1): 163–166 [21 Feb 2009]. doi:10.1002/ange.200804560. ^{[永久失效链接]}

[24] [24]
大蒜辣素；蒜素；蒜辣素；大蒜素. 化工引擎. [2009-09-05]. （原始内容存档于2011-02-04）.

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