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Isao Kubo – One of the best experts on this subject based on the ideXlab platform.

  • Evaluation of lipoxygenase inhibitory activity of Anacardic Acids.
    Zeitschrift fur Naturforschung. C Journal of biosciences, 2008
    Co-Authors: Isao Kubo, Kazuo Tsujimoto, Felismino E Tocoli, Ivan R Green
    Abstract:

    6-Alkylsalicylic Acids inhibit the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) competitively and without pro-oxidant effects. This activity is largely dependent on the nature of their alkyl side chains. Inhibitory activities of Anacardic Acids, viz. 6-pentadec(en)ylsalicylic Acids, isolated from the cashew Anacardium occidentale, were initially used for comparison because their aromatic head portions are the same. Consequently, the data should be interpreted to mean that changes in the hydrophobic side chain tail portions of the molecules evaluated correlate with the specific activity determined.

  • Anacardic Acids and ferric ion chelation.
    Zeitschrift fur Naturforschung. C Journal of biosciences, 2007
    Co-Authors: Kazuo Tsujimoto, Akio Hayashi, Isao Kubo
    Abstract:

    6-Pentadeca(e)nylsalicylic Acids isolated from the cashew Anacardium occidentale L. (Anacardiaceae), commonly known as Anacardic Acids, inhibited the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) competitively without prooxidant effects. Their parent compound, salicylic acid, did not have this inhibitory activity up to 800 pm, indicating that the pentadeca(e)nyl group is an essential element to elicit the activity. The inhibition is attributed to its ability to chelate iron in the enzyme. Thus, Anacardic Acids chelate iron in the active site of the enzyme and then the hydrophobic tail portion slowly begins to interact with the hydrophobic domain close to the active site. Formation of the Anacardic Acids-ferric ion complex was detected in the ratio of 2:1 as the base peak in the negative ion elecelectrospray ioniionization mass spectrometry. Hence, Anacardic Acids inhibit both Eox and Ered forms.

  • Design and evaluation of Anacardic acid derivatives as anticavity agents.
    European journal of medicinal chemistry, 2007
    Co-Authors: Ivan R Green, Ken-ichi Nihei, Felismino E Tocoli, Sang Hwa Lee, Isao Kubo
    Abstract:

    Abstract On the basis of antibacterial Anacardic Acids, 6-pentadecenylsalicylic Acids, isolated from the cashew apple, Anacardium occidentale L. (Anacardiaceae), a series of 6-alk(en)ylsalicylic Acids were synthesized and tested for their antibacterial activity against Streptococcus mutans ATCC 25175. Among them, 6-(4′,8′-dimethylnonyl)salicylic acid was found to exhibit the most potent antibacterial activity against this cariogenic bacterium with the minimum inhibition concentration (MIC) of 0.78 μg/ml.

Kazuo Tsujimoto – One of the best experts on this subject based on the ideXlab platform.

  • Evaluation of lipoxygenase inhibitory activity of Anacardic Acids.
    Zeitschrift fur Naturforschung. C Journal of biosciences, 2008
    Co-Authors: Isao Kubo, Kazuo Tsujimoto, Felismino E Tocoli, Ivan R Green
    Abstract:

    6-Alkylsalicylic Acids inhibit the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) competitively and without pro-oxidant effects. This activity is largely dependent on the nature of their alkyl side chains. Inhibitory activities of Anacardic Acids, viz. 6-pentadec(en)ylsalicylic Acids, isolated from the cashew Anacardium occidentale, were initially used for comparison because their aromatic head portions are the same. Consequently, the data should be interpreted to mean that changes in the hydrophobic side chain tail portions of the molecules evaluated correlate with the specific activity determined.

  • Anacardic Acids and ferric ion chelation.
    Zeitschrift fur Naturforschung. C Journal of biosciences, 2007
    Co-Authors: Kazuo Tsujimoto, Akio Hayashi, Isao Kubo
    Abstract:

    6-Pentadeca(e)nylsalicylic Acids isolated from the cashew Anacardium occidentale L. (Anacardiaceae), commonly known as Anacardic Acids, inhibited the linoleic acid peroxidation catalyzed by soybean lipoxygenase-1 (EC 1.13.11.12, type 1) competitively without prooxidant effects. Their parent compound, salicylic acid, did not have this inhibitory activity up to 800 pm, indicating that the pentadeca(e)nyl group is an essential element to elicit the activity. The inhibition is attributed to its ability to chelate iron in the enzyme. Thus, Anacardic Acids chelate iron in the active site of the enzyme and then the hydrophobic tail portion slowly begins to interact with the hydrophobic domain close to the active site. Formation of the Anacardic Acids-ferric ion complex was detected in the ratio of 2:1 as the base peak in the negative ion electrospray ionization mass spectrometry. Hence, Anacardic Acids inhibit both Eox and Ered forms.

  • Antioxidant activity of Anacardic Acids
    Food Chemistry, 2006
    Co-Authors: Isao Kubo, Noriyoshi Masuoka, Kazuo Tsujimoto
    Abstract:

    Abstract Anacardic Acids, 6-pentadec(en)ylsalicylic Acids isolated from the cashew Anacardium occidentale L. (Anacardiaceae) nut and apple, were found to possess preventive antioxidant activity while salicylic acid did not show this activity. These Anacardic Acids prevent generation of superoxide radicals by inhibiting xanthine oxidase (EC 1.1.3.22, Grade IV) without radical-scavenging activity. Notably, the inhibition kinetics of Anacardic Acids do not follow hyperbolic dependence of enzyme inhibition on inhibitor contents (Michaelis–Menten equation) but follow the Hill equation instead. Anacardic acid (C 15:1 ) inhibited the soybean lipoxygenase-1 (EC 1.13.11.12, Type 1) catalyzed oxidation of linoleic acid with an IC 50 of 6.8 μM. The inhibition is a slow and reversible reaction without residual enzyme activity. The inhibition kinetics indicate that Anacardic acid (C 15:1 ) is a competitive inhiinhibitor and the inhibition constant, K I , was 2.8 μM. Anacardic Acids act as antioxidants in a variety ways, including inhibition of various prooxidant enzymes involved in the production of the reactive oxygen species and chelate divalent metal ions such as Fe 2+ or Cu 2+ , but do not quench reactive oxygen species. The C 15 -alkenyl side chain is largely associated with the activity.

Hisae Muroi – One of the best experts on this subject based on the ideXlab platform.

  • Synergistic effects of Anacardic Acids and methicillin against methicillin resistant Staphylococcus aureus
    Bioorganic & medicinal chemistry, 2004
    Co-Authors: Hisae Muroi, Kazuo Tsujimoto, Ken-ichi Nihei, Isao Kubo
    Abstract:

    The synergistic effects of 6-alk(en)ylsalcylic Acids, also known as Anacardic Acids, in combination with methicillin against Staphylococcus aureus ATCC 33591 (MRSA) was investigated. The double bond in C15-Anacardic Acids is not essential in eliciting the antibacterial activity but is associated with increasing the activity. The synergistic effects decreased with increasing the number of double bonds in the alkyl chain. On the other hand, the antibacterial activity of Anacardic Acids possessing different alkyl chain lengths against the same MRSA strain was found to be a parabolic function of their lipophilicity and maximized with the alkyl chain length of C10 and C12. Notably, the synergistic effects were noted to increase with increasing the alkyl chain length.

  • structure antibacterial activity relationships of Anacardic Acids
    Journal of Agricultural and Food Chemistry, 1993
    Co-Authors: Isao Kubo, Hisae Muroi, Masaki Himejima, Yoshiro Yamagiwa, Hiroyuki Mera, Kimihiro Tokushima, Shigeo Ohta, Tadao Kamikawa
    Abstract:

    A series of Anacardic Acids possessing different side-chain lengths were synthesized, and their antimicrobial activity was tested. In the case against Staphylococcus aureus, the Anacardic acid having the C 10 alkyl side chain was most active, while against Propionibacterium acnes, Streptococcus mutant, and Brevibacterium ammoniagenes, the Anacardic acid possessing the C 12 alkyl side chain was most effective

  • Bactericidal activity of Anacardic Acids against Streptococcus mutans and their potentiation
    Journal of Agricultural and Food Chemistry, 1993
    Co-Authors: Hisae Muroi, Isao Kubo
    Abstract:

    Anacardic Acids isolated from the cashew Anacardium occidentale L. (Anacardiaceae) apple and a series of their synthetic analogs, 6-alkylsalicylic Acids, were found to be bactericidal against Streptococcus mutans by the time-kill curve method. The maximum antibacterial activity of 6-alkylsalicylic Acids against this cariogenic bacterium showed when the carbon length comprised 12 carbon atoms in the side chain. To enhance the bactericidal activity of Anacardic Acids, various combinations were tested. Synergistic bactericidal activity was found in the combination of Anacardic acid [6-[8(Z,11(Z),14-pentadecatrienyl]salicylic acid] and anethole or linalool

Vassya Bankova – One of the best experts on this subject based on the ideXlab platform.

  • New Insights into Tropical Propolis: Propolis from Pitcairn Island
    , 2018
    Co-Authors: Boryana Trusheva, Milena Popova, Kristina Georgieva, Veselina Uzunova, Tihomira Stoyanova, Violeta Valcheva, Rumiana Tzoneva, Vassya Bankova
    Abstract:

    Propolis (bee glue) has a long history of being used in traditional medicine and nowadays it is extensively used in food diet to improve health and prevent diseases such as inflammation, heart disease, diabetes, and even cancer. Because of its broad spectrum of biological activities there is an undying interest in the composition of propolis, which depends on the vegetation of the area from which propolis was collected. There are numerous reports in the literature on the isolation and structural elucidation of biologically active phytochemicals from propolis collected in Europe, South America, Asia and the Pacific region. However there is no data about chemical composition and biological activity of propolis from Pitcairn Islands 1 . The chemical profiles of Pitcairn propolis extracts were obtained by GC-MS analysis after silylation. The major constituents were terpenoids (mainly diterpenes and less triterpenes). Phenolic components (cardanols, alk(en)ylresorcinols and Anacardic Acids) are present in significantly lower amounts, as flavonoids and the usually present phenolic Acids are completely absent. After detailed chemical investigation of propolisdichloromethane extract, four new cycloartane triterpenes with good antimicrobial activity, along with 18 known compounds, were isolated. The biological activity of this extract was also examined and the results showed that it inhibits human breast cancer MDA-MB-231 cells proliferation and induces changes of malignant cells’ morphology, which hint to apoptotic events. Apart from this the studied propolis extract possesses strong antimicrobial activity against some of the most common pathogens causing infections in humans: Staphylococcus aureus , Escherichia coli , and Candida albicans . Thus, the present research provides additional data for the tropical propolis constituents, revealing the distinct character of Pitcairn propolis. Furthermore, these findings once again certify the potential role of propolis as a natural chemopreventive agent and a valuable bioactive mixture for a combination therapy approach. Acknowledgements: The Pitcairn Island Producers’ Co-operative (PIPCO) for providing the sample.

  • RESEARCH ARTICLE Open Access Omani propolis: chemical profiling, antibacterial
    , 2014
    Co-Authors: Milena Popova, Rosa Dimitrova, Hassan Talib Al-lawati, Iva Tsvetkova, Hristo Najdenski, Vassya Bankova
    Abstract:

    Background: Propolis (bee glue) is a resinous honeybee product having a long history of application in many countries as a traditional remedy for treating wounds, burns, soar throat, stomach disorders, etc. It has been proved to possess beneficial biological effects, including antimicrobial, antioxidant, anti-inflammatory, cytotoxic, antiulcer, and many others. Bees gather propolis from diverse resinous plant parts and in different phytogeographic regions its chemical composition might vary significantly. In this article we report the results of the first study on the chemical profiles of propolis from Oman, its plant origin and antibacterial activity. Results: The chemical profiles of Omani propolis extracts were obtained by GC-MS analysis after silylation. Over 50 individual compounds were identified in the samples, belonging to different compound types: sugars, polyols, hydroxy Acids, fatty Acids, cardanols and cardols, Anacardic Acids, flavan derivatives, triterpenes, prenylated flavanones and chalcones. The profiles were dissimilar from other known propolis types. They demonstrate that although Oman is not a large country, the plant sources of propolis vary significantly, even in the same apiary and the same season. Based on chemical profiles, and isolation and identification of major marker compounds (new propolis constituents), new plant sources of propolis were found: Azadiracta indica (neem tree) and Acacia spp. (most probably A. nilotica). The ethanol extracts of the studied propolis samples demonstrated activity agains

  • Omani propolis: chemical profiling, antibacterial activity and new propolis plant sources
    Chemistry Central Journal, 2013
    Co-Authors: Milena Popova, Rosa Dimitrova, Hassan Talib Al-lawati, Iva Tsvetkova, Hristo Najdenski, Vassya Bankova
    Abstract:

    Propolis (bee glue) is a resinous honeybee product having a long history of application in many countries as a traditional remedy for treating wounds, burns, soar throat, stomach disorders, etc. It has been proved to possess beneficial biological effects, including antimicrobial, antioxidant, anti-inflammatory, cytotoxic, antiulcer, and many others. Bees gather propolis from diverse resinous plant parts and in different phytogeographic regions its chemical composition might vary significantly. In this article we report the results of the first study on the chemical profiles of propolis from Oman, its plant origin and antibacterial activity. The chemical profiles of Omani propolis extracts were obtained by GC-MS analysis after silylation. Over 50 individual compounds were identified in the samples, belonging to different compound types: sugars, polyols, hydroxy Acids, fatty Acids, cardanols and cardols, Anacardic Acids, flavan derivatives, triterpenes, prenylated flavanones and chalcones. The profiles were dissimilar from other known propolis types. They demonstrate that although Oman is not a large country, the plant sources of propolis vary significantly, even in the same apiary and the same season. Based on chemical profiles, and isolation and identification of major marker compounds (new propolis constituents), new plant sources of propolis were found: Azadiracta indica (neem tree) and Acacia spp. (most probably A. nilotica). The ethanol extracts of the studied propolis samples demonstrated activity against S. aureus (MIC 

Ken-ichi Nihei – One of the best experts on this subject based on the ideXlab platform.

  • Design and evaluation of Anacardic acid derivatives as anticavity agents.
    European journal of medicinal chemistry, 2007
    Co-Authors: Ivan R Green, Ken-ichi Nihei, Felismino E Tocoli, Sang Hwa Lee, Isao Kubo
    Abstract:

    Abstract On the basis of antibacterial Anacardic Acids, 6-pentadecenylsalicylic Acids, isolated from the cashew apple, Anacardium occidentale L. (Anacardiaceae), a series of 6-alk(en)ylsalicylic Acids were synthesized and tested for their antibacterial activity against Streptococcus mutans ATCC 25175. Among them, 6-(4′,8′-dimethylnonyl)salicylic acid was found to exhibit the most potent antibacterial activity against this cariogenic bacterium with the minimum inhibition concentration (MIC) of 0.78 μg/ml.

  • Synergistic effects of Anacardic Acids and methicillin against methicillin resistant Staphylococcus aureus
    Bioorganic & medicinal chemistry, 2004
    Co-Authors: Hisae Muroi, Kazuo Tsujimoto, Ken-ichi Nihei, Isao Kubo
    Abstract:

    The synergistic effects of 6-alk(en)ylsalcylic Acids, also known as Anacardic Acids, in combination with methicillin against Staphylococcus aureus ATCC 33591 (MRSA) was investigated. The double bond in C15-Anacardic Acids is not essential in eliciting the antibacterial activity but is associated with increasing the activity. The synergistic effects decreased with increasing the number of double bonds in the alkyl chain. On the other hand, the antibacterial activity of Anacardic Acids possessing different alkyl chain lengths against the same MRSA strain was found to be a parabolic function of their lipophilicity and maximized with the alkyl chain length of C10 and C12. Notably, the synergistic effects were noted to increase with increasing the alkyl chain length.

  • Antibacterial Action of Anacardic Acids against Methicillin Resistant Staphylococcus aureus (MRSA)
    Journal of agricultural and food chemistry, 2003
    Co-Authors: Isao Kubo, Ken-ichi Nihei, Kazuo Tsujimoto
    Abstract:

    The structural and antibacterial activity relationship of 6-alk(en)ylsalicylic Acids, also known as Anacardic Acids, was investigated against Gram-positive bacteria, emphasizing the methicillin resistant Staphylococcus aureus ATCC 33591 (MRSA) strain. The unsaturation in the alkyl side chain is not essential in eliciting activity but is associated with increasing the activity. The antibacterial activity of methicillin against MRSA strains was significantly enhanced in combination with C12:0-Anacardic acid, and the fractional inhibitory concentration index for this combination was calculated as 0.281. It appears that biophysical disruption of the membrane (surfactant property) is due to the primary response to their antibacterial activity, while biochemical mechanisms are little involved. The compounds possessing the similar log P values exhibit similar activity. Keywords: Antibacterial activity; methicillin resistant Staphylococcus aureus (MRSA); Anacardic Acids; surfactants; synergists; methicillin; frac…