In vitro suppression of HIV-1 replication by ajoene [(e)-(z)-4,5,9-trithiadodeca-1,6,11-triene-9 oxide]

Walder, R.; Kalvatchev, Z.; Garzaro, Domingo; Linares‐Barrios, Mario; Apitz‐Castro, Rafael

doi:10.1016/s0753-3322(97)89433-4

Cited by 28 publications

(19 citation statements)

References 16 publications

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“…(E)-Ajoene ((E)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene; ( 1 ), (Z)-ajoene ((Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene; ( 2 ), 3-vinyl-4H-1,2-dithiin (3-ethenyl-3,4-dihydrodithiine; ( 3 ), 2-vinyl-4H-1,3-dithiin (2-ethenyl-4H-1,3-dithiine; ( 4 ), and diallyl disulfide (3-(prop-2-enyldisulfanyl)prop-1-ene; ( 5 ) were isolated. 1 and 2 exhibit antimicrobial [25, 26] and anticancer effect [27, 28]. 3 and 4 participate in the inhibition of thrombocyte aggregation, cyclooxygenase and 5-lipoxygenase inhibition, and regulation of systolic and diastolic blood pressure [29].…”

Section: Resultsmentioning

confidence: 99%

Transformation of Synthetic Allicin: The Influence of Ultrasound, Microwaves, Different Solvents and Temperatures, and the Products Isolation

Ilić

Nikolić

Stanković

et al. 2012

The Scientific World Journal

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The transformation of the synthesized allicin, using conventional method, the influence of ultrasound and microwaves, in different organic solvents (acetonitrile, acetone, methanol, and chloroform), at various temperatures (room temperature, 45°C, and 55°C) was investigated. Allicin degradation kinetic was monitored by HPLC. Allicin transformation under the effect of microwaves is faster than transformations performed under the influence of ultrasound or by conventional method. Increase of the temperature accelerates allicin transformation. Pharmacologically active compounds of (E)-ajoene, (Z)-ajoene, 3-vinyl-4H-1,2-dithiin, 2-vinyl-4H-1,3-dithiin, and diallyl disulfide were isolated from the mixture of transformation products of allicin under the influence of microwaves in methanol at 55°C, which is according to kinetic parameters (highest values of the order of reaction and the lowest activation energy) the optimal method.

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Section: Resultsmentioning

confidence: 99%

Transformation of Synthetic Allicin: The Influence of Ultrasound, Microwaves, Different Solvents and Temperatures, and the Products Isolation

Ilić

Nikolić

Stanković

et al. 2012

The Scientific World Journal

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“…Among the organosulfur compounds identified in garlic extracts, ajoene (4,5,9-trithiadodeca-1,6,11-triene 9-oxide) has enjoyed increasing attention in view of its remarkably wide range of activities, which includes antithrombotic [3], antimicrobial [4], antifungal [5], cytostatic and cytotoxic [6], hypocholesterolemic [7], antidiabetic [8], immunosuppressive and antineoplastic [9], anti-HIV [10] and other effects. Its isolation and in vitro inhibition of human platelet aggregation were reported in 1983 [3].…”

Section: Introductionmentioning

confidence: 99%

Preparation, Thermal Behaviour and Solid-state Structures of Inclusion Complexes of Permethylated-β-cyclodextrin with the Garlic-derived Antithrombotics (E)- and (Z)-Ajoene

Caira

Hunter

Bourne

et al. 2004

Supramolecular Chemistry

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The E and Z isomers of the antithrombotic ajoene (4,5,9-trithiadodeca-1,6,11-triene 9-oxide), components of garlic (Allium Sativa, L.), were complexed with heptakis(2,3,6-tri-O-methyl)-b-cyclodextrin (TRIMEB) to yield solid inclusion compounds with the compositions TRIMEB·(E)-ajoene·0.5H 2 O (1) and TRIMEB·(Z)-ajoene (2). These species were investigated by thermal analysis techniques (HSM, TGA, DSC), powder X-ray diffraction (PXRD) and single-crystal X-ray diffraction at 173 K. Thermal analysis of 1 revealed dehydration followed by melting at 143.88C, and only melting at 140.58C for 2. The complexes yielded different PXRD traces, indicating crystallization in different arrangements. Single-crystal X-ray methods revealed the space groups P2 1 (1) and P2 1 2 1 2 1 (2) and the simultaneous presence of the guest stereoisomers in both complexes. Refinement of guest site-occupancies showed that each complex crystal consists of a mixture of diastereomers in 1:1 molar ratio. The different crystal packing arrangements for 1 and 2 are induced by the distinctly different modes of inclusion of the E and Z isomers.

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“…As anti‐viral properties of Z ‐ajoene have been previously reported [9], we examined whether it could block HCMV spreading in vitro. U373MG and MRC5 cell lines which are known to be permissive for HCMV in vitro, have been infected for 24 h before treatment with non‐toxic doses of Z ‐ajoene (see ) for further 24 h. Apoptosis was then quantified by using Annexin V staining.…”

Section: Resultsmentioning

confidence: 99%

“…In the Middle Ages, it was used to treat plague and cholera and in the World War I for curing wounds. Anti‐bacterial activity of garlic is known from Pasteur since 1858 and its anti‐proliferative, pro‐apoptotic, anti‐tumoral, anti‐viral and anti‐platelet aggregation properties are known for 50 years [1–11]. Garlic's efficacy depends on the activity of products resulting from the breakage of alliin into allicin.…”

Section: Introductionmentioning

confidence: 99%

Activities of Z‐ajoene against tumour and viral spreading in vitro

Terrasson

et al. 2007

Fundamemntal Clinical Pharma

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Z-ajoene is a garlic-derived compound with known anti-tumour properties. This report argues in favour of pro-apoptotic and cell cycle blockage activities of Z-ajoene on various cell lines involving activation of the p53-family gene products, p53, p63 and p73, at indicated doses. According to its known anti-proteasome activity, Z-ajoene induced a downregulation of MHC-class I expression at the surface of treated cells but did not impair their recognition by CD8+ T cells. We further demonstrated a new activity of Z-ajoene against human cytomegalovirus spreading in vitro that was mediated by an increased number of apoptotic cells after infection. Altogether our data point at the ubiquitous efficiency of Z-ajoene as a new compound to fight against cancers of various origins including those that put up viruses.

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In vitro suppression of HIV-1 replication by ajoene [(e)-(z)-4,5,9-trithiadodeca-1,6,11-triene-9 oxide]

Cited by 28 publications

References 16 publications

Transformation of Synthetic Allicin: The Influence of Ultrasound, Microwaves, Different Solvents and Temperatures, and the Products Isolation

Transformation of Synthetic Allicin: The Influence of Ultrasound, Microwaves, Different Solvents and Temperatures, and the Products Isolation

Preparation, Thermal Behaviour and Solid-state Structures of Inclusion Complexes of Permethylated-β-cyclodextrin with the Garlic-derived Antithrombotics (E)- and (Z)-Ajoene

Activities of Z‐ajoene against tumour and viral spreading in vitro

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