Alliin (BioDeep_00000000302)

Main id: BioDeep_00000017295

Secondary id: BioDeep_00001874156

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acid

化学式: C6H11NO3S (177.0459616)
中文名称: (±)-L-蒜氨酸, (+)-蒜氨酸, 蒜氨酸
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 3.51%

Reviewed

Last reviewed on 2024-07-01.

Cite this Page

Alliin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/(r)c(s)s-alliin (retrieved 2024-09-18) (BioDeep RN: BioDeep_00000000302). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C=CCS(=O)CC(C(=O)O)N
InChI: InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)

描述信息

Alliin /ˈæli.ɪn/ is a sulfoxide that is a natural constituent of fresh garlic.[1] It is a derivative of the amino acid cysteine. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin and other thiosulfinates in garlic are unstable and form a number of other compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene.[2] Garlic powder is not a source of alliin, nor is fresh garlic upon maceration, since the enzymatic conversion to allicin takes place in the order of seconds.

Alliin was the first natural product found to have both carbon- and sulfur-centered stereochemistry.[3]

Constituent of garlic oil (Allium sativum), also from ramsons (Allium ursinum). (R)C(S)S-Alliin is found in garden onion, garlic, and onion-family vegetables.
(R)C(S)S-Alliin is found in garden onion. (R)C(S)S-Alliin is a constituent of garlic oil (Allium sativum), also from ramsons (Allium ursinum).

Alliin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=556-27-4 (retrieved 2024-07-01) (CAS RN: 556-27-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Alliin, an orally active sulfoxide compound derived from garlic, exhibits hypoglycemic, antioxidant and anti-inflammatory activities[1][2].
Alliin, an orally active sulfoxide compound derived from garlic, exhibits hypoglycemic, antioxidant and anti-inflammatory activities[1][2].

同义名列表

18 个代谢物同义名

2-Amino-3-(prop-2-ene-1-sulphinyl)propanoic acid; 2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid; 2-Amino-3-(prop-2-ene-1-sulphinyl)propanoate; 2-Amino-3-(prop-2-ene-1-sulfinyl)propanoate; S-(2-propenyl)cysteine sulfoxide; 3-(Allylsulphinyl)-L-alanine; 3-(Allylsulfinyl)-L-alanine; alliin, (L-Ala)-(S)-isomer; alliin, (L-Ala)-(R)-isomer; S-allylcysteine sulfoxide; alliin, (L-Ala)-isomer; (R)C(S)S-Alliin; (±)-Alliin; isoalliin; alliin; Allin; PCSO; 2-amino-3-prop-2-enylsulfinylpropanoic acid



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(2)

代谢反应

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

2 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Wenhui Wu, Yang Xu, Yadi Zhang, Zhengjiao Yu, Yumeng Pang, Lei Qin, Yong Wang. [Cloning and functional analysis of AcFMO from onion during alliine biosynthesis]. Sheng wu gong cheng xue bao = Chinese journal of biotechnology. 2024 Apr; 40(4):1076-1088. doi: 10.13345/j.cjb.230527. [PMID: 38658150]
  • Annalisa Chiavaroli, Fabrizio Masciulli, Cinzia Ingallina, Luisa Mannina, Maria Loreta Libero, Simonetta Cristina Di Simone, Alessandra Acquaviva, Nilofar, Lucia Recinella, Sheila Leone, Luigi Brunetti, Simone Carradori, Luca Cantò, Giustino Orlando, Gokhan Zengin, Abdullah Ibrahim Uba, Ugur Cakilcioğlu, Muzaffer Mukemre, Omer Elkiran, Maura Di Vito, Luigi Menghini, Claudio Ferrante. Comprehensive metabolite and biological profile of "Sulmona Red Garlic" ecotype's aerial bulbils. Food research international (Ottawa, Ont.). 2024 Jan; 175(?):113654. doi: 10.1016/j.foodres.2023.113654. [PMID: 38129017]
  • Ricarda Freke, Björn Heinemann, Samuel Edward Hakim, Claus-Peter Witte, Marco Herde, Tatjana M Hildebrandt, Jakob Franke. Isotope-guided metabolomics reveals divergent incorporation of valine into different flavor precursor classes in chives. Chembiochem : a European journal of chemical biology. 2023 Feb; ?(?):e202300056. doi: 10.1002/cbic.202300056. [PMID: 36853993]
  • Meitong Liu, Jing Lu, Shuting Yang, Yuelin Chen, Jing Yu, Shuang Guan. Alliin alleviates LPS-induced pyroptosis via promoting mitophagy in THP-1 macrophages and mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2022 Feb; 160(?):112811. doi: 10.1016/j.fct.2022.112811. [PMID: 34999177]
  • Xuqin Yang, Yiren Su, Jiaying Wu, Wen Wan, Huijian Chen, Xiaoying Cao, Junjuan Wang, Zhong Zhang, Youzhi Wang, Deliang Ma, G J Loake, Jihong Jiang. Parallel analysis of global garlic gene expression and alliin content following leaf wounding. BMC plant biology. 2021 Apr; 21(1):174. doi: 10.1186/s12870-021-02948-0. [PMID: 33838642]
  • Costanza Ceccanti, Gabriele Rocchetti, Luigi Lucini, Gianluca Giuberti, Marco Landi, Stefano Biagiotti, Lucia Guidi. Comparative phytochemical profile of the elephant garlic (Allium ampeloprasum var. holmense) and the common garlic (Allium sativum) from the Val di Chiana area (Tuscany, Italy) before and after in vitro gastrointestinal digestion. Food chemistry. 2021 Feb; 338(?):128011. doi: 10.1016/j.foodchem.2020.128011. [PMID: 32950006]
  • Sucheta Khubber, Reza Hashemifesharaki, Mehrdad Mohammadi, Seyed Mohammad Taghi Gharibzahedi. Garlic (Allium sativum L.): a potential unique therapeutic food rich in organosulfur and flavonoid compounds to fight with COVID-19. Nutrition journal. 2020 11; 19(1):124. doi: 10.1186/s12937-020-00643-8. [PMID: 33208167]
  • Yuya Nakayama, Hsin-Jung Ho, Miki Yamagishi, Hiroyuki Ikemoto, Michio Komai, Hitoshi Shirakawa. Cysteine Sulfoxides Enhance Steroid Hormone Production via Activation of the Protein Kinase A Pathway in Testis-Derived I-10 Tumor Cells. Molecules (Basel, Switzerland). 2020 Oct; 25(20):. doi: 10.3390/molecules25204694. [PMID: 33066465]
  • Murugan Sesha Subramanian, Giri Nandagopal Ms, Syafinaz Amin Nordin, Karuppiah Thilakavathy, Narcisse Joseph. Prevailing Knowledge on the Bioavailability and Biological Activities of Sulphur Compounds from Alliums: A Potential Drug Candidate. Molecules (Basel, Switzerland). 2020 Sep; 25(18):. doi: 10.3390/molecules25184111. [PMID: 32916777]
  • Maria Giovanna Lupo, Noemi Biancorosso, Elisa Brilli, Germano Tarantino, Maria Pia Adorni, Greta Vivian, Marika Salvalaio, Stefano Dall'Acqua, Stefania Sut, Cédric Neutel, Haixia Chen, Alessandro Bressan, Elisabetta Faggin, Marcello Rattazzi, Nicola Ferri. Cholesterol-Lowering Action of a Novel Nutraceutical Combination in Uremic Rats: Insights into the Molecular Mechanism in a Hepatoma Cell Line. Nutrients. 2020 Feb; 12(2):. doi: 10.3390/nu12020436. [PMID: 32050453]
  • Li-Jun Yue, Xi-Yu Zhu, Rui-Sha Li, Hui-Jing Chang, Bing Gong, Chong-Chong Tian, Chang Liu, Yun-Xing Xue, Qing Zhou, Tian-Shu Xu, Dong-Jin Wang. S‑allyl‑cysteine sulfoxide (alliin) alleviates myocardial infarction by modulating cardiomyocyte necroptosis and autophagy. International journal of molecular medicine. 2019 Nov; 44(5):1943-1951. doi: 10.3892/ijmm.2019.4351. [PMID: 31573046]
  • Iveta Štefanová, Jakub Zápal, Martin Moos, Marek Kuzma, Roman Kubec. Isoalliin-Derived Thiolanes Formed in Homogenized Onion. Journal of agricultural and food chemistry. 2019 Sep; 67(35):9895-9906. doi: 10.1021/acs.jafc.9b01384. [PMID: 31091093]
  • Juntong Yu, Hui Guo, Jinli Xie, Jianming Luo, Yuetong Li, Liu Liu, Shiyi Ou, Guangwen Zhang, Xichun Peng. The Alternate Consumption of Quercetin and Alliin in the Traditional Asian Diet Reshaped Microbiota and Altered Gene Expression of Colonic Epithelial Cells in Rats. Journal of food science. 2019 Mar; 84(3):678-686. doi: 10.1111/1750-3841.14473. [PMID: 30768688]
  • Elham Zare, Amirhesam Alirezaei, Mahmood Bakhtiyari, Asieh Mansouri. Evaluating the effect of garlic extract on serum inflammatory markers of peritoneal dialysis patients: a randomized double-blind clinical trial study. BMC nephrology. 2019 01; 20(1):26. doi: 10.1186/s12882-019-1204-6. [PMID: 30683061]
  • Nabarun Roy, P A Nazeem, T D Babu, P S Abida, Arunaksharan Narayanankutty, Ravisankar Valsalan, P A Valsala, Achuthan C Raghavamenon. EGFR gene regulation in colorectal cancer cells by garlic phytocompounds with special emphasis on S-Allyl-L-Cysteine Sulfoxide. Interdisciplinary sciences, computational life sciences. 2018 Dec; 10(4):686-693. doi: 10.1007/s12539-017-0227-6. [PMID: 28349439]
  • Harumi Uto-Kondo, Ayumu Hase, Yusuke Yamaguchi, Ayaka Sakurai, Makoto Akao, Takeshi Saito, Hitomi Kumagai. S-Allyl-L-cysteine sulfoxide, a garlic odor precursor, suppresses elevation in blood ethanol concentration by accelerating ethanol metabolism and preventing ethanol absorption from gut. Bioscience, biotechnology, and biochemistry. 2018 Apr; 82(4):724-731. doi: 10.1080/09168451.2018.1447357. [PMID: 29616890]
  • Baiqiang Zhai, Chuanhai Zhang, Yao Sheng, Changhui Zhao, Xiaoyun He, Wentao Xu, Kunlun Huang, Yunbo Luo. Hypoglycemic and hypolipidemic effect of S-allyl-cysteine sulfoxide (alliin) in DIO mice. Scientific reports. 2018 02; 8(1):3527. doi: 10.1038/s41598-018-21421-x. [PMID: 29476144]
  • Jing Lu, Bijun Cheng, Zhuoqun Meng, Baochen Fang, Tianjiao Li, Maocheng Sun, Meitong Liu, Shuang Guan. Alliin attenuates 1, 3-dichloro-2-propanol-induced lipogenesis in HepG2 cells through activation of the AMP-activated protein kinase-dependent pathway. Life sciences. 2018 Feb; 195(?):19-24. doi: 10.1016/j.lfs.2017.12.040. [PMID: 29305303]
  • Dandan Tao, Bing Zhou, Luyao Zhang, Xiaosong Hu, Xiaojun Liao, Yan Zhang. 'Laba' garlic processed by dense phase carbon dioxide: the relation between green colour generation and cellular structure, alliin consumption and alliinase activity. Journal of the science of food and agriculture. 2016 Jul; 96(9):2969-75. doi: 10.1002/jsfa.7463. [PMID: 26374695]
  • Qing Chang, Yue'e Peng, Bin Shi, Conghui Dan, Yijun Yang, Qin Shuai. In situ Identification of Labile Precursor Compounds and their Short-lived Intermediates in Plants using in vivo Nanospray High-resolution Mass Spectrometry. Phytochemical analysis : PCA. 2016 May; 27(3-4):184-90. doi: 10.1002/pca.2614. [PMID: 27313155]
  • Hirotaka Amano, Daichi Kazamori, Kenji Itoh. Pharmacokinetics of S-Allyl-l-cysteine in Rats Is Characterized by High Oral Absorption and Extensive Renal Reabsorption. The Journal of nutrition. 2016 Feb; 146(2):456S-459S. doi: 10.3945/jn.114.201749. [PMID: 26764325]
  • Ethiene Castellucci Estevam, Sharoon Griffin, Muhammad Jawad Nasim, Dariusz Zieliński, Justyna Aszyk, Magdalena Osowicka, Natalia Dawidowska, Rinaldi Idroes, Agnieszka Bartoszek, Claus Jacob. Inspired by Nature: The Use of Plant-derived Substrate/Enzyme Combinations to Generate Antimicrobial Activity in situ. Natural product communications. 2015 Oct; 10(10):1733-8. doi: . [PMID: 26669114]
  • Naoko Yoshimoto, Misato Onuma, Shinya Mizuno, Yuka Sugino, Ryo Nakabayashi, Shinsuke Imai, Tadamitsu Tsuneyoshi, Shin-ichiro Sumi, Kazuki Saito. Identification of a flavin-containing S-oxygenating monooxygenase involved in alliin biosynthesis in garlic. The Plant journal : for cell and molecular biology. 2015 Sep; 83(6):941-51. doi: 10.1111/tpj.12954. [PMID: 26345717]
  • Wen-Qing Li, Hua Zhou, Mei-Yun Zhou, Xing-Peng Hu, Shi-Yi Ou, Ri-An Yan, Xiao-Jian Liao, Xue-Song Huang, Liang Fu. Characterization of phenolic constituents inhibiting the formation of sulfur-containing volatiles produced during garlic processing. Journal of agricultural and food chemistry. 2015 Jan; 63(3):787-94. doi: 10.1021/jf505982f. [PMID: 25579175]
  • Su-Chen Ho, Min-Sheng Su. Evaluating the anti-neuroinflammatory capacity of raw and steamed garlic as well as five organosulfur compounds. Molecules (Basel, Switzerland). 2014 Oct; 19(11):17697-714. doi: 10.3390/molecules191117697. [PMID: 25365295]
  • Nathalie Bernaert, Marc De Loose, Erik Van Bockstaele, Bart Van Droogenbroeck. Antioxidant changes during domestic food processing of the white shaft and green leaves of leek (Allium ampeloprasum var. porrum). Journal of the science of food and agriculture. 2014 Apr; 94(6):1168-74. doi: 10.1002/jsfa.6389. [PMID: 24105673]
  • Michał Majewski. Allium sativum: facts and myths regarding human health. Roczniki Panstwowego Zakladu Higieny. 2014; 65(1):1-8. doi: . [PMID: 24964572]
  • Weng Ieong Tou, Su-Sen Chang, Dongchuan Wu, Ted Weita Lai, Yu Tian Wang, Chung Y Hsu, Calvin Yu-Chian Chen. Molecular level activation insights from a NR2A/NR2B agonist. Journal of biomolecular structure & dynamics. 2014; 32(5):683-93. doi: 10.1080/07391102.2013.787371. [PMID: 23600691]
  • James D Kean, David Camfield, Jerome Sarris, Marni Kras, Richard Silberstein, Andrew Scholey, Con Stough. A randomized controlled trial investigating the effects of PCSO-524, a patented oil extract of the New Zealand green lipped mussel (Perna canaliculus), on the behaviour, mood, cognition and neurophysiology of children and adolescents (aged 6-14 years) experiencing clinical and sub-clinical levels of hyperactivity and inattention: study protocol ACTRN12610000978066. Nutrition journal. 2013 Jul; 12(?):100. doi: 10.1186/1475-2891-12-100. [PMID: 23866813]
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  • Jing Wang, Yanping Cao, Chengtao Wang, Baoguo Sun. Low-frequency and low-intensity ultrasound accelerates alliinase-catalysed synthesis of allicin in freshly crushed garlic. Journal of the science of food and agriculture. 2011 Aug; 91(10):1766-72. doi: 10.1002/jsfa.4377. [PMID: 21480265]
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