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Ajoene

目录号 : GC46821

A disulfide with antitumor and antiplatelet activities

Ajoene Chemical Structure

Cas No.:92285-01-3

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产品描述

Ajoene is a disulfide that has been found in A. sativum and has diverse biological activities, including antibacterial, anticancer, antiplatelet, and antioxidant properties.1,2,3,4 It is active against Gram-positive (MICs = 5-160 µg/ml) and Gram-negative bacteria (MICs = 136-200 µg/ml), as well as yeasts (MICs = 10-20 µg/ml).1 Ajoene is cytotoxic to mouse melanoma cells (IC50 = 18 µM), as well as human colon, lung, mammary, and pancreatic cancer cells (IC50s = 7-41 µM).2 It reduces tumor growth in a B16/BL6 mouse model of melanoma when administered at a dose of 25 mg/kg every other day and decreases the number of lung metastases when administered prior to tumor cell inoculation at doses ranging from 1-25 mg/kg. It inhibits ADP- or collagen-induced platelet aggregation in isolated baboon platelets when used at concentrations ranging from 75 to 150 µg/ml and in platelet-rich plasma isolated from baboons when administered at a dose of 25 mg/kg.3 Ajoene (25 mg/kg) prevents thrombus formation on damaged arterial walls in heparinized pigs in an in situ model of thrombogenesis.5 It also reduces high-fat diet-induced hepatic steatosis, histopathological markers of liver damage, thiobarbituric acid reactive substances (TBARS) formation, and protein oxidation in a mouse model of non-alcoholic fatty liver disease (NAFLD).4

1.Naganawa, R., Iwata, N., Ishikawa, K., et al.Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlicAppl. Environ. Microbiol.62(11)4238-4242(1996) 2.Taylor, P., Noriega, R., Farah, C., et al.Ajoene inhibits both primary tumor growth and metastasis of B16/BL6 melanoma cells in C57BL/6 miceCancer Lett.239(2)298-304(2006) 3.Teranishi, K., Apitz-Castro, R., Robson, S.C., et al.Inhibition of baboon platelet aggregation in vitro and in vivo by the garlic derivative, ajoeneXenotransplantation10(4)374-379(2003) 4.Han, C.Y., Ki, S.H., Kim, Y.W., et al.Ajoene, a stable garlic by-product, inhibits high fat diet-induced hepatic steatosis and oxidative injury through LKB1-dependent AMPK activationAntioxid. Redox Signal.14(2)187-202(2011) 5.Apitz-Castro, R., Badimon, J.J., and Badimon, L.A garlic derivative, ajoene, inhibits platelet deposition on severely damaged vessel wall in an in vivo porcine experimental modelThromb. Res.75(3)243-249(1994)

Chemical Properties

Cas No. 92285-01-3 SDF
化学名 2-propen-1-yl[3-(2-propen-1-ylsulfinyl)-1-propen-1-yl] disulfide
Canonical SMILES C=CCS(C/C=C/SSCC=C)=O
分子式 C9H14OS3 分子量 234.4
溶解度 Chloroform: slightly soluble,Ethyl Acetate: slightly soluble,Methanol: slightly soluble 储存条件 Store at -20°C
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1 mM 4.2662 mL 21.3311 mL 42.6621 mL
5 mM 0.8532 mL 4.2662 mL 8.5324 mL
10 mM 0.4266 mL 2.1331 mL 4.2662 mL
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Research Update

Ajoene (natural garlic compound): a new anti-leukaemia agent for AML therapy

Leuk Res 2004 Jul;28(7):667-71.PMID:15158086DOI:10.1016/j.leukres.2003.10.008.

The reputation of garlic (Allium sativum) as an effective remedy for tumours extends back to the Egyptian Codex Ebers of 1550 b.c. Several garlic compounds including allicin and its corresponding sulfide inhibit the proliferation and induce apoptosis of several human non-leukaemia malignant cells including breast, bladder, colorectal, hepatic, prostate cancer, lymphoma and skin tumour cell lines. Ajoene (4,5,9-trithiadodeca-1,6,11-triene-9-oxide) is a garlic-derived compound produced most efficiently from pure allicin and has the advantage of a greater chemical stability than allicin. Several clinical trials and in vitro studies of Ajoene have demonstrated its best-known anti-thrombosis, anti-microbial and cholesterol lowering activities. Recently, topic application of Ajoene has produced significant clinical response in patients with skin basal cell carcinoma. Ajoene was shown to inhibit proliferation and induce apoptosis of several human leukaemia CD34-negative cells including HL-60, U937, HEL and OCIM-1. Also, Ajoene induces 30% apoptosis in myeloblasts from chronic myeloid leukaemia patient in blast crisis. More significantly, Ajoene profoundly enhanced the apoptotic effect of the two chemotherapeutic drugs: cytarabine and fludarabine in human CD34-positive resistant myeloid leukaemia cells through enhancing their bcl-2 inhibitory and caspase-3 activation activities. The two key anti-leukaemia biological actions of Ajoene were the inhibition of proliferation and the induction of apoptosis. Studies have shown the anti-proliferation activity of Ajoene to be associated with a block in the G2/M phase of cell cycle in human myeloid leukaemia cells. The apoptosis inducing activity of Ajoene is via the mitochondria-dependent caspase cascade through a significant reduction of the anti-apoptotic bcl-2 that results in release of cytochrome c and the activation of caspase-3. Since acute myeloid leukaemia (AML) is a heterogeneous malignant disease in which disease progression at the level of CD34-positive cells has a major impact on resistance to chemotherapy and relapse and the inability to undergo apoptosis is a crucial mechanism of multi-drug resistance in AML patients. The recent findings of the potent enhancing activity of Ajoene on chemotherapy-induced apoptosis in CD34-positive resistant human myeloid leukaemia cells suggest a novel promising role for the treatment of refractory and/or relapsed AML patients as well as elderly AML patients. Further studies are warranted to evaluate similar enhancing effect for Ajoene in blast cells from AML patients in primary cultures before its introduction in pilot clinical study.

Bioactive Compounds and Biological Functions of Garlic ( Allium sativum L.)

Foods 2019 Jul 5;8(7):246.PMID:31284512DOI:10.3390/foods8070246.

Garlic (Allium sativum L.) is a widely consumed spice in the world. Garlic contains diverse bioactive compounds, such as allicin, alliin, diallyl sulfide, diallyl disulfide, diallyl trisulfide, Ajoene, and S-allyl-cysteine. Substantial studies have shown that garlic and its bioactive constituents exhibit antioxidant, anti-inflammatory, antibacterial, antifungal, immunomodulatory, cardiovascular protective, anticancer, hepatoprotective, digestive system protective, anti-diabetic, anti-obesity, neuroprotective, and renal protective properties. In this review, the main bioactive compounds and important biological functions of garlic are summarized, highlighting and discussing the relevant mechanisms of actions. Overall, garlic is an excellent natural source of bioactive sulfur-containing compounds and has promising applications in the development of functional foods or nutraceuticals for the prevention and management of certain diseases.

[Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent]

Rev Iberoam Micol 2006 Jun;23(2):75-80.PMID:16854181DOI:10.1016/s1130-1406(06)70017-1.

The curative properties of garlic in medicine have been known for a long time. But, it was only in the last three decades when garlic properties were seriously investigated confirming its potential as therapeutic agent. Allicin, Ajoene, thiosulfinates and a wide range of other organosulphurate compounds, are known to be the constituents linked to the garlic properties. Regarding the biochemical properties of these compounds, Ajoene [(E,Z)-4,5,9 Trithiadodeca 1,6,11 Triene 9-oxide] is stable in water, and it can be obtained by chemical synthesis. There is evidence that some of the garlic constituents exert a wide variety of effects on different biological systems. However, Ajoene is the garlic compound related to more biological activities, as showed in in vitro and in vivo systems. Those studies found that Ajoene has antithrombotic, anti-tumoral,antifungal, and antiparasitic effects. This study deals with a recently described antifungal property of Ajoene, and its potential use in clinical trails to treat several fungal infections.

Garlic-derived anticancer agents: structure and biological activity of Ajoene

Biofactors 2010 Jan-Feb;36(1):78-85.PMID:20108330DOI:10.1002/biof.76.

Garlic has been used throughout the centuries to treat infections, heart disease, and cancer. Ajoene is one of the main compounds formed from heating crushed garlic as a mixture of E- and Z-isomers (E- and Z-4,5,9-trithiadodeca-1,6,11-triene 9-oxide). Ajoene possesses a broad spectrum of biological activities that include anticancer activity. It's cytotoxicity towards cancer cells is postulated to occur via an apoptotic mechanism involving activation of the mitochondrial-dependent caspase cascade. Structure-activity studies on Ajoene and Ajoene analogues have revealed that the Z-isomer is moderately more active than the E-isomer at inhibiting in vitro tumor cell growth, suggesting that specific protein interactions may be important. Substitution of the terminal end allyl groups in Ajoene for alkyl, aromatic, or heteroaromatic groups produces some analogs with superior in vitro anticancer activity to Ajoene, opening up the way to developing ajoene-based anticancer agents.

Z-ajoene from Crushed Garlic Alleviates Cancer-Induced Skeletal Muscle Atrophy

Nutrients 2019 Nov 10;11(11):2724.PMID:31717643DOI:10.3390/nu11112724.

Skeletal muscle atrophy is one of the major symptoms of cancer cachexia. Garlic (Allium sativum), one of the world's most commonly used and versatile herbs, has been employed for the prevention and treatment of diverse diseases for centuries. In the present study, we found that Ajoene, a sulfur compound found in crushed garlic, exhibits protective effects against muscle atrophy. Using CT26 tumor-bearing BALB/c mice, we demonstrate in vivo that Ajoene extract alleviated muscle degradation by decreasing not only myokines secretion but also janus kinase/signal transducer and activator of transcription 3 (JAK/STAT3) and SMADs/forkhead box (FoxO) signaling pathways, thereby suppressing muscle-specific E3 ligases. In mouse skeletal myoblasts, Z-ajoene enhanced myogenesis as evidenced by increased expression of myogenic markers via p38 mitogen-activated protein kinase (MAPK) activation. In mature myotubes, Z-ajoene protected against muscle protein degradation induced by conditioned media from CT26 colon carcinoma cells, by suppressing expression of muscle specific E3 ligases and nuclear transcription factor kappa B (NF-κB) phosphorylation which contribute to muscle atrophy. Moreover, Z-ajoene treatment improved myofiber formation via stimulation of muscle protein synthesis. These findings suggest that Ajoene extract and Z-ajoene can attenuate skeletal muscle atrophy induced by cancer cachexia through suppressing inflammatory responses and the muscle wasting as well as by promoting muscle protein synthesis.