Ajoene (BioDeep_00000004078)

 

Secondary id: BioDeep_00000395460, BioDeep_00001869251

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene

化学式: C9H14OS3 (234.0207)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 69.33%

分子结构信息

SMILES: C=CCSS/C=C/C[S+]([O-])CC=C
InChI: InChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-

描述信息

Ajoene is found in onion-family vegetables. Ajoene is isolated from garlic (Allium sativum) extracts. Nutriceutical with anti-cancer properties Ajoene is a chemical compound available from garlic (Allium sativum). The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of two isomers, E-, and Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxide. Ajoene, an unsaturated disulfide, is formed from the bonding of three allicin molecules. Allicin is a sulfinyl compound that gives garlic its strong odor and flavor. The release of allicin occurs after a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil)
Ajoene is a member of the class of compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R (R,R not H). Ajoene is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Ajoene can be found in garlic, onion-family vegetables, and soft-necked garlic, which makes ajoene a potential biomarker for the consumption of these food products. The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of up to four isomers, which differ in terms of the stereochemistry of central alkene (E- vs Z-) and the chirality of the sulfoxide .
D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors
D000890 - Anti-Infective Agents > D000935 - Antifungal Agents
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
D004791 - Enzyme Inhibitors

同义名列表

13 个代谢物同义名

3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene; 2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9ci; Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenyl; 2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfide; Allyl 3-allylsulfinyl-1-propenyl disulfide; 4,5,9-Trithia-1,6,11-dodecatriene 9-oxide; 4,5,9-trithiadodeca-1,6,11-triene 9-oxide; Acuagel; Adjoen; trans-Ajoene; cis-Ajoene; (Z)-Ajoene; Ajoene; (Z)-Ajoene



数据库引用编号

19 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(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

22 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。

亚细胞结构定位 关联基因列表
Cytoplasm 4 BCL2, CASP3, CD34, PTK2
Peripheral membrane protein 2 HSD17B6, PTK2
Endoplasmic reticulum membrane 1 BCL2
Nucleus 3 BCL2, CASP3, PTK2
cytosol 3 BCL2, CASP3, PTK2
centrosome 1 PTK2
nucleoplasm 1 CASP3
Cell membrane 1 PTK2
Cytoplasmic side 1 PTK2
Early endosome membrane 1 HSD17B6
cell cortex 1 PTK2
glutamatergic synapse 1 CASP3
neuronal cell body 1 CASP3
Lysosome 1 CD34
plasma membrane 2 CD34, PTK2
Membrane 2 BCL2, CD34
apical plasma membrane 1 CD34
Lumenal side 1 HSD17B6
endoplasmic reticulum 2 BCL2, HSD17B6
perinuclear region of cytoplasm 2 CD34, PTK2
mitochondrion 1 BCL2
protein-containing complex 1 BCL2
intracellular membrane-bounded organelle 2 HSD17B6, PTK2
Microsome membrane 1 HSD17B6
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 CD34
extracellular region 1 CD34
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
anchoring junction 1 PTK2
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 PTK2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 CD34
dendritic spine 1 PTK2
Cytoplasm, perinuclear region 1 PTK2
pore complex 1 BCL2
Cell junction, focal adhesion 1 PTK2
Cytoplasm, cytoskeleton 1 PTK2
focal adhesion 1 PTK2
ciliary basal body 1 PTK2
cell projection 1 PTK2
cytoskeleton 1 PTK2
Cytoplasm, cytoskeleton, cilium basal body 1 PTK2
Cytoplasm, cell cortex 1 PTK2
intercellular bridge 1 CD34
myelin sheath 1 BCL2
stress fiber 1 PTK2
basal plasma membrane 1 CD34
death-inducing signaling complex 1 CASP3
BAD-BCL-2 complex 1 BCL2
glomerular endothelium fenestra 1 CD34


文献列表

  • Daniel A Kusza, Roger Hunter, Georgia Schäfer, Muneerah Smith, Arieh A Katz, Catherine H Kaschula. Activity-Based Proteomic Identification of the S-Thiolation Targets of Ajoene in MDA-MB-231 Breast Cancer Cells. Journal of agricultural and food chemistry. 2022 Nov; 70(46):14679-14692. doi: 10.1021/acs.jafc.2c04972. [PMID: 36351177]
  • Hyejin Lee, Ji-Won Heo, A-Reum Kim, Minson Kweon, Sorim Nam, Jong-Seok Lim, Mi-Kyung Sung, Sung-Eun Kim, Jae-Ha Ryu. Z-ajoene from Crushed Garlic Alleviates Cancer-Induced Skeletal Muscle Atrophy. Nutrients. 2019 Nov; 11(11):. doi: 10.3390/nu11112724. [PMID: 31717643]
  • Masashi Fukaya, Seikou Nakamura, Ryota Nakagawa, Manami Kinka, Souichi Nakashima, Hisashi Matsuda. Cyclic sulfur-containing compounds from Allium fistulosum 'Kujou'. Journal of natural medicines. 2019 Mar; 73(2):397-403. doi: 10.1007/s11418-018-1272-0. [PMID: 30535771]
  • Tim H Jakobsen, Anders N Warming, Rebecca M Vejborg, Joana A Moscoso, Marc Stegger, Frederik Lorenzen, Morten Rybtke, Jens B Andersen, Rico Petersen, Paal Skytt Andersen, Thomas E Nielsen, Tim Tolker-Nielsen, Alain Filloux, Hanne Ingmer, Michael Givskov. A broad range quorum sensing inhibitor working through sRNA inhibition. Scientific reports. 2017 08; 7(1):9857. doi: 10.1038/s41598-017-09886-8. [PMID: 28851971]
  • Vuyolwethu Siyo, Georgia Schäfer, Roger Hunter, Andriy Grafov, Iryna Grafova, Martin Nieger, Arieh A Katz, M Iqbal Parker, Catherine H Kaschula. The Cytotoxicity of the Ajoene Analogue BisPMB in WHCO1 Oesophageal Cancer Cells Is Mediated by CHOP/GADD153. Molecules (Basel, Switzerland). 2017 May; 22(6):. doi: 10.3390/molecules22060892. [PMID: 28555042]
  • Truong Thanh Tung, Tim Holm Jakobsen, Trong Tuan Dao, Anja Thoe Fuglsang, Michael Givskov, Søren Brøgger Christensen, John Nielsen. Fusaric acid and analogues as Gram-negative bacterial quorum sensing inhibitors. European journal of medicinal chemistry. 2017 Jan; 126(?):1011-1020. doi: 10.1016/j.ejmech.2016.11.044. [PMID: 28033578]
  • Masoud Foroutan-Rad, Khosrow Hazrati Tappeh, Shahram Khademvatan. Antileishmanial and Immunomodulatory Activity of Allium sativum (Garlic): A Review. Journal of evidence-based complementary & alternative medicine. 2017 Jan; 22(1):141-155. doi: 10.1177/2156587215623126. [PMID: 26721553]
  • Catherine H Kaschula, Roger Hunter, Jonathan Cotton, Rossana Tuveri, Ellen Ngarande, Kevin Dzobo, Georgia Schäfer, Vuyolwethu Siyo, Dirk Lang, Daniel A Kusza, Bronwen Davies, Arieh A Katz, M Iqbal Parker. The garlic compound ajoene targets protein folding in the endoplasmic reticulum of cancer cells. Molecular carcinogenesis. 2016 08; 55(8):1213-28. doi: 10.1002/mc.22364. [PMID: 26207910]
  • C F Williams, A R Vacca, L Dunham, D Lloyd, M P Coogan, G Evans, M Graz, J Cable. The redox-active drug metronidazole and thiol-depleting garlic compounds act synergistically in the protist parasite Spironucleus vortens. Molecular and biochemical parasitology. 2016 Mar; 206(1-2):20-8. doi: 10.1016/j.molbiopara.2016.03.001. [PMID: 26968264]
  • Anitha Vadekeetil, Hina Saini, Sanjay Chhibber, Kusum Harjai. Exploiting the antivirulence efficacy of an ajoene-ciprofloxacin combination against Pseudomonas aeruginosa biofilm associated murine acute pyelonephritis. Biofouling. 2016; 32(4):371-82. doi: 10.1080/08927014.2015.1137289. [PMID: 26930141]
  • Dae Young Yoo, Woosuk Kim, Sung Min Nam, Miyoung Yoo, Sanghee Lee, Yeo Sung Yoon, Moo-Ho Won, In Koo Hwang, Jung Hoon Choi. Neuroprotective effects of Z-ajoene, an organosulfur compound derived from oil-macerated garlic, in the gerbil hippocampal CA1 region after transient forebrain ischemia. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2014 Oct; 72(?):1-7. doi: 10.1016/j.fct.2014.06.023. [PMID: 24997311]
  • Yuki Washiya, Tomoaki Nishikawa, Tsuchiyoshi Fujino. Enhancement of intestinal IgA production by Ajoene in mice. Bioscience, biotechnology, and biochemistry. 2013; 77(11):2298-301. doi: 10.1271/bbb.130408. [PMID: 24200781]
  • Tim Holm Jakobsen, Maria van Gennip, Richard Kerry Phipps, Meenakshi Sundaram Shanmugham, Louise Dahl Christensen, Morten Alhede, Mette Eline Skindersoe, Thomas Bovbjerg Rasmussen, Karlheinz Friedrich, Friedrich Uthe, Peter Østrup Jensen, Claus Moser, Kristian Fog Nielsen, Leo Eberl, Thomas Ostenfeld Larsen, David Tanner, Niels Høiby, Thomas Bjarnsholt, Michael Givskov. Ajoene, a sulfur-rich molecule from garlic, inhibits genes controlled by quorum sensing. Antimicrobial agents and chemotherapy. 2012 May; 56(5):2314-25. doi: 10.1128/aac.05919-11. [PMID: 22314537]
  • Coralie O M Millet, David Lloyd, Catrin Williams, David Williams, Gareth Evans, Robert A Saunders, Joanne Cable. Effect of garlic and allium-derived products on the growth and metabolism of Spironucleus vortens. Experimental parasitology. 2011 Feb; 127(2):490-9. doi: 10.1016/j.exppara.2010.10.001. [PMID: 21056027]
  • Raquel Ruiz, M P García, A Lara, L A Rubio. Garlic derivatives (PTS and PTS-O) differently affect the ecology of swine faecal microbiota in vitro. Veterinary microbiology. 2010 Jul; 144(1-2):110-7. doi: 10.1016/j.vetmic.2009.12.025. [PMID: 20080364]
  • Suresh Ambati, Jeong-Yeh Yang, Srujana Rayalam, Hea Jin Park, Mary Anne Della-Fera, Clifton A Baile. Ajoene exerts potent effects in 3T3-L1 adipocytes by inhibiting adipogenesis and inducing apoptosis. Phytotherapy research : PTR. 2009 Apr; 23(4):513-8. doi: 10.1002/ptr.2663. [PMID: 19051208]
  • Atsuhiko Hattori, Norihiko Yamada, Tomoaki Nishikawa, Hiroyuki Fukuda, Tsuchiyoshi Fujino. Antidiabetic effects of ajoene in genetically diabetic KK-A(y) mice. Journal of nutritional science and vitaminology. 2005 Oct; 51(5):382-4. doi: 10.3177/jnsv.51.382. [PMID: 16392712]
  • C Nelson-Dooley, M A Della-Fera, M Hamrick, C A Baile. Novel treatments for obesity and osteoporosis: targeting apoptotic pathways in adipocytes. Current medicinal chemistry. 2005; 12(19):2215-25. doi: 10.2174/0929867054864886. [PMID: 16178781]
  • N Yamada, A Hattori, T Hayashi, T Nishikawa, H Fukuda, T Fujino. Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice. Pharmacology, biochemistry, and behavior. 2004 Aug; 78(4):787-91. doi: 10.1016/j.pbb.2004.05.017. [PMID: 15301936]
  • H T Hassan. Ajoene (natural garlic compound): a new anti-leukaemia agent for AML therapy. Leukemia research. 2004 Jul; 28(7):667-71. doi: 10.1016/j.leukres.2003.10.008. [PMID: 15158086]
  • Bo Xu, Bernard Monsarrat, Jean Edouard Gairin, Elisabeth Girbal-Neuhauser. Effect of ajoene, a natural antitumor small molecule, on human 20S proteasome activity in vitro and in human leukemic HL60 cells. Fundamental & clinical pharmacology. 2004 Apr; 18(2):171-80. doi: 10.1111/j.1472-8206.2004.00219.x. [PMID: 15066131]
  • Eliades Ledezma, Rafael Apitz-Castro, José Cardier. Apoptotic and anti-adhesion effect of ajoene, a garlic derived compound, on the murine melanoma B16F10 cells: possible role of caspase-3 and the alpha(4)beta(1) integrin. Cancer letters. 2004 Mar; 206(1):35-41. doi: 10.1016/j.canlet.2003.10.031. [PMID: 15019157]
  • M Pérez-Blanco, R Hernández Valles, G Fernández Zeppenfeldt, R Apitz-Castro. Ajoene and 5-fluorouracil in the topical treatment of Cladophialophora carrionii chromoblastomycosis in humans: a comparative open study. Medical mycology. 2003 Dec; 41(6):517-20. doi: 10.1080/13693780310001616519. [PMID: 14725326]
  • Katsuhito Teranishi, Rafael Apitz-Castro, Simon C Robson, Egidio Romano, David K C Cooper. Inhibition of baboon platelet aggregation in vitro and in vivo by the garlic derivative, ajoene. Xenotransplantation. 2003 Jul; 10(4):374-9. doi: 10.1034/j.1399-3089.2003.02068.x. [PMID: 12795687]
  • Lorenzo Benatuil, Rafael Apitz-Castro, Egidio Romano. Ajoene inhibits the activation of human endothelial cells induced by porcine cells: implications for xenotransplantation. Xenotransplantation. 2003 Jul; 10(4):368-73. doi: 10.1034/j.1399-3089.2003.02016.x. [PMID: 12795686]
  • C M L J Tilli, A J W Stavast-Kooy, J D D Vuerstaek, M R T M Thissen, G A M Krekels, F C S Ramaekers, H A M Neumann. The garlic-derived organosulfur component ajoene decreases basal cell carcinoma tumor size by inducing apoptosis. Archives of dermatological research. 2003 Jul; 295(3):117-23. doi: 10.1007/s00403-003-0404-9. [PMID: 12756587]
  • Nicola Ferri, Kohei Yokoyama, Martin Sadilek, Rodolfo Paoletti, Rafael Apitz-Castro, Michael H Gelb, Alberto Corsini. Ajoene, a garlic compound, inhibits protein prenylation and arterial smooth muscle cell proliferation. British journal of pharmacology. 2003 Mar; 138(5):811-8. doi: 10.1038/sj.bjp.0705126. [PMID: 12642382]
  • Stephen R Davis, Rosemary Perrie, Rafael Apitz-Castro. The in vitro susceptibility of Scedosporium prolificans to ajoene, allitridium and a raw extract of garlic (Allium sativum). The Journal of antimicrobial chemotherapy. 2003 Mar; 51(3):593-7. doi: 10.1093/jac/dkg144. [PMID: 12615859]
  • Dorothee S M Antlsperger, Verena M Dirsch, Dulce Ferreira, Jen-Liang Su, Ming-Liang Kuo, Angelika M Vollmar. Ajoene-induced cell death in human promyeloleukemic cells does not require JNK but is amplified by the inhibition of ERK. Oncogene. 2003 Jan; 22(4):582-9. doi: 10.1038/sj.onc.1206161. [PMID: 12555071]
  • Tomoaki Nishikawa, Norihiko Yamada, Atsuhiko Hattori, Hiroyuki Fukuda, Tsuchiyoshi Fujino. Inhibition by ajoene of skin-tumor promotion in mice. Bioscience, biotechnology, and biochemistry. 2002 Oct; 66(10):2221-3. doi: 10.1271/bbb.66.2221. [PMID: 12450136]
  • Eliades Ledezma, Alicia Jorquera, Herminia Bendezú, Julio Vivas, Gladinex Pérez. Antiproliferative and leishmanicidal effect of ajoene on various Leishmania species: ultrastructural study. Parasitology research. 2002 Aug; 88(8):748-53. doi: 10.1007/s00436-002-0649-9. [PMID: 12122433]
  • Min Li, Jing-Rong Ciu, Ying Ye, Ji-Mei Min, Li-He Zhang, Kui Wang, Michèle Gares, Jean Cros, Michel Wright, Jeanne Leung-Tack. Antitumor activity of Z-ajoene, a natural compound purified from garlic: antimitotic and microtubule-interaction properties. Carcinogenesis. 2002 Apr; 23(4):573-9. doi: 10.1093/carcin/23.4.573. [PMID: 11960908]
  • Min Li, Ji-Mei Min, Jing-Rong Cui, Li-He Zhang, Kui Wang, Annie Valette, Christian Davrinche, Michel Wright, Jeanne Leung-Tack. Z-ajoene induces apoptosis of HL-60 cells: involvement of Bcl-2 cleavage. Nutrition and cancer. 2002; 42(2):241-7. doi: 10.1207/s15327914nc422_14. [PMID: 12416266]
  • V M Dirsch, D S M Antlsperger, H Hentze, A M Vollmar. Ajoene, an experimental anti-leukemic drug: mechanism of cell death. Leukemia. 2002 Jan; 16(1):74-83. doi: 10.1038/sj.leu.2402337. [PMID: 11840266]
  • A Hattori, N Yamada, T Nishikawa, H Fukuda, T Fujino. Protective effect of ajoene on acetaminophen-induced hepatic injury in mice. Bioscience, biotechnology, and biochemistry. 2001 Nov; 65(11):2555-7. doi: 10.1271/bbb.65.2555. [PMID: 11791733]
  • N Ahmed, L Laverick, J Sammons, H Zhang, D J Maslin, H T Hassan. Ajoene, a garlic-derived natural compound, enhances chemotherapy-induced apoptosis in human myeloid leukaemia CD34-positive resistant cells. Anticancer research. 2001 Sep; 21(5):3519-23. doi: . [PMID: 11848518]
  • V M Dirsch, A M Vollmar. Ajoene, a natural product with non-steroidal anti-inflammatory drug (NSAID)-like properties?. Biochemical pharmacology. 2001 Mar; 61(5):587-93. doi: 10.1016/s0006-2952(00)00580-3. [PMID: 11239502]
  • E Ledezma, K Marcano, A Jorquera, De Sousa L, M Padilla, M Pulgar, R Apitz-Castro. Efficacy of ajoene in the treatment of tinea pedis: a double-blind and comparative study with terbinafine. Journal of the American Academy of Dermatology. 2000 Nov; 43(5 Pt 1):829-32. doi: 10.1067/mjd.2000.107243. [PMID: 11050588]
  • J A MacDonald, R F Langler. Structure-activity relationships for selected sulfur-rich antithrombotic compounds. Biochemical and biophysical research communications. 2000 Jul; 273(2):421-4. doi: 10.1006/bbrc.2000.2950. [PMID: 10873621]
  • E Ledezma, J C López, P Marin, H Romero, G Ferrara, L De Sousa, A Jorquera, R Apitz Castro. Ajoene in the topical short-term treatment of tinea cruris and tinea corporis in humans. Randomized comparative study with terbinafine. Arzneimittel-Forschung. 1999 Jun; 49(6):544-7. doi: 10.1055/s-0031-1300459. [PMID: 10417874]
  • H Gallwitz, S Bonse, A Martinez-Cruz, I Schlichting, K Schumacher, R L Krauth-Siegel. Ajoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: crystallographic, kinetic, and spectroscopic studies. Journal of medicinal chemistry. 1999 Feb; 42(3):364-72. doi: 10.1021/jm980471k. [PMID: 9986706]
  • V M Dirsch, A K Kiemer, H Wagner, A M Vollmar. Effect of allicin and ajoene, two compounds of garlic, on inducible nitric oxide synthase. Atherosclerosis. 1998 Aug; 139(2):333-9. doi: 10.1016/s0021-9150(98)00094-x. [PMID: 9712340]
  • H Yoshida, N Iwata, H Katsuzaki, R Naganawa, K Ishikawa, H Fukuda, T Fujino, A Suzuki. Antimicrobial activity of a compound isolated from an oil-macerated garlic extract. Bioscience, biotechnology, and biochemistry. 1998 May; 62(5):1014-7. doi: 10.1271/bbb.62.1014. [PMID: 9648236]
  • V M Dirsch, A L Gerbes, A M Vollmar. Ajoene, a compound of garlic, induces apoptosis in human promyeloleukemic cells, accompanied by generation of reactive oxygen species and activation of nuclear factor kappaB. Molecular pharmacology. 1998 Mar; 53(3):402-7. doi: 10.1124/mol.53.3.402. [PMID: 9495804]
  • J A Esté, E De Clercq. Ajoene [(e,z)-4,5,9-trithiadodeca-1,6,11-triene 9 oxide] does not exhibit antiviral activity at subtoxic concentrations. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 1998; 52(5):236-8. doi: 10.1016/s0753-3322(98)80022-x. [PMID: 9755821]
  • R Walder, Z Kalvatchev, R Apitz-Castro. Selective in vitro protection of SIVagm-induced cytolysis by ajoene, [(E)-(Z)-4,5,9-trithiadodeca-1,6,11-triene-9 oxide]. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 1998; 52(5):229-35. doi: 10.1016/s0753-3322(98)80021-8. [PMID: 9755820]
  • I V Andrianova, Z A Gabbasov, V G Ionova, A N Orekhov. [Effect of the garlic tablets allicor on thrombocyte aggregation in vitro and ex vivo]. Biulleten' eksperimental'noi biologii i meditsiny. 1997 Jul; 124(7):97-100. doi: ". [PMID: 9303744]
  • Gioconda San-Bias, Julio A Urbina, Edgar Marchán, Lellys M Contreras, Françoise Sorais, Felipe San-Blas. Inhibition of Paracoccidioides brasiliensis by ajoene is associated with blockade of phosphatidylcholine biosynthesis. Microbiology (Reading, England). 1997 May; 143 ( Pt 5)(?):1583-1586. doi: 10.1099/00221287-143-5-1583. [PMID: 9168609]
  • R Villar, M T Alvariño, R Flores. Inhibition by ajoene of protein tyrosine phosphatase activity in human platelets. Biochimica et biophysica acta. 1997 Feb; 1337(2):233-40. doi: 10.1016/s0167-4838(96)00170-7. [PMID: 9048900]
  • E L Romano, R F Montaño, B Brito, R Apitz, J Alonso, M Romano, S Gebrán, A Soyano. Effects of Ajoene on lymphocyte and macrophage membrane-dependent functions. Immunopharmacology and immunotoxicology. 1997 Feb; 19(1):15-36. doi: 10.3109/08923979709038531. [PMID: 9049657]
  • R Walder, Z Kalvatchev, D Garzaro, M Barrios, R Apitz-Castro. In vitro suppression of HIV-1 replication by ajoene [(e)-(z)-4,5,9-trithiadodeca-1,6,11-triene-9 oxide]. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 1997; 51(9):397-403. doi: 10.1016/s0753-3322(97)89433-4. [PMID: 9452790]
  • K Ishikawa, R Naganawa, H Yoshida, N Iwata, H Fukuda, T Fujino, A Suzuki. Antimutagenic effects of ajoene, an organosulfur compound derived from garlic. Bioscience, biotechnology, and biochemistry. 1996 Dec; 60(12):2086-8. doi: 10.1271/bbb.60.2086. [PMID: 8988645]
  • R Naganawa, N Iwata, K Ishikawa, H Fukuda, T Fujino, A Suzuki. Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic. Applied and environmental microbiology. 1996 Nov; 62(11):4238-42. doi: 10.1128/aem.62.11.4238-4242.1996. [PMID: 8900018]
  • E Ledezma, L DeSousa, A Jorquera, J Sanchez, A Lander, E Rodriguez, M K Jain, R Apitz-Castro. Efficacy of ajoene, an organosulphur derived from garlic, in the short-term therapy of tinea pedis. Mycoses. 1996 Sep; 39(9-10):393-5. doi: 10.1111/j.1439-0507.1996.tb00160.x. [PMID: 9009665]
  • S Rai, U P Singh, G D Mishra, S P Singh, Samarketu, K G Wagner. Synergistic effects of ajoene and the microwave power density memories of water on germination inhibition of fungal spores. Medical & biological engineering & computing. 1995 May; 33(3):313-6. doi: 10.1007/bf02510505. [PMID: 7475368]
  • R Apitz-Castro, J J Badimon, L Badimon. A garlic derivative, ajoene, inhibits platelet deposition on severely damaged vessel wall in an in vivo porcine experimental model. Thrombosis research. 1994 Aug; 75(3):243-9. doi: 10.1016/0049-3848(94)90235-6. [PMID: 7992235]
  • R Gebhardt, H Beck, K G Wagner. Inhibition of cholesterol biosynthesis by allicin and ajoene in rat hepatocytes and HepG2 cells. Biochimica et biophysica acta. 1994 Jun; 1213(1):57-62. doi: 10.1016/0005-2760(94)90222-4. [PMID: 8011681]
  • H A Perez, M De la Rosa, R Apitz. In vivo activity of ajoene against rodent malaria. Antimicrobial agents and chemotherapy. 1994 Feb; 38(2):337-9. doi: 10.1128/aac.38.2.337. [PMID: 8192460]
  • K Scharfenberg, T Ryll, R Wagner, K G Wagner. Injuries to cultivated BJA-B cells by ajoene, a garlic-derived natural compound: cell viability, glutathione metabolism, and pools of acidic amino acids. Journal of cellular physiology. 1994 Jan; 158(1):55-60. doi: 10.1002/jcp.1041580108. [PMID: 8263028]
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  • J A Urbina, E Marchan, K Lazardi, G Visbal, R Apitz-Castro, F Gil, T Aguirre, M M Piras, R Piras. Inhibition of phosphatidylcholine biosynthesis and cell proliferation in Trypanosoma cruzi by ajoene, an antiplatelet compound isolated from garlic. Biochemical pharmacology. 1993 Jun; 45(12):2381-7. doi: 10.1016/0006-2952(93)90217-k. [PMID: 8328978]
  • G San-Blas, L Mariño, F San-Blas, R Apitz-Castro. Effect of ajoene on dimorphism of Paracoccidioides brasiliensis. Journal of medical and veterinary mycology : bi-monthly publication of the International Society for Human and Animal Mycology. 1993; 31(2):133-41. doi: 10.1080/02681219380000151. [PMID: 8509950]
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  • P P Tadi, B H Lau, R W Teel, C E Herrmann. Binding of aflatoxin B1 to DNA inhibited by ajoene and diallyl sulfide. Anticancer research. 1991 Nov; 11(6):2037-41. doi: . [PMID: 1776837]
  • R Apitz-Castro, M K Jain, F Bartoli, E Ledezma, M C Ruiz, R Salas. Evidence for direct coupling of primary agonist-receptor interaction to the exposure of functional IIb-IIIa complexes in human blood platelets. Results from studies with the antiplatelet compound ajoene. Biochimica et biophysica acta. 1991 Sep; 1094(3):269-80. doi: 10.1016/0167-4889(91)90086-d. [PMID: 1911878]
  • G Blania, B Spangenberg. [Formation of allicin from dried garlic (Allium sativum): a simple HPTLC method for simultaneous determination of allicin and ajoene in dried garlic and garlic preparations]. Planta medica. 1991 Aug; 57(4):371-5. doi: 10.1055/s-2006-960120. [PMID: 1775580]
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  • F Rendu, D Daveloose, J C Debouzy, N Bourdeau, S Levy-Toledano, M K Jain, R Apitz-Castro. Ajoene, the antiplatelet compound derived from garlic, specifically inhibits platelet release reaction by affecting the plasma membrane internal microviscosity. Biochemical pharmacology. 1989 Apr; 38(8):1321-8. doi: 10.1016/0006-2952(89)90339-0. [PMID: 2539823]
  • J C Debouzy, J M Neumann, M Hervé, D Daveloose, J Viret, R Apitz-Castro. Interaction of antiaggregant molecule ajoene with membranes. An ESR and 1H, 2H, 31P-NMR study. European biophysics journal : EBJ. 1989; 17(4):211-6. doi: 10.1007/bf00284727. [PMID: 2558875]
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  • R Apitz-Castro, E Ledezma, J Escalante, M K Jain. The molecular basis of the antiplatelet action of ajoene: direct interaction with the fibrinogen receptor. Biochemical and biophysical research communications. 1986 Nov; 141(1):145-50. doi: 10.1016/s0006-291x(86)80346-1. [PMID: 3800991]
  • R Apitz-Castro, J Escalante, R Vargas, M K Jain. Ajoene, the antiplatelet principle of garlic, synergistically potentiates the antiaggregatory action of prostacyclin, forskolin, indomethacin and dypiridamole on human platelets. Thrombosis research. 1986 May; 42(3):303-11. doi: 10.1016/0049-3848(86)90259-8. [PMID: 3520940]