New Stilbene Derivatives from Calligonum leucocladum

Okasaka, Mamoru; Takaishi, Yoshihisa; Kogure, Kentarou; Fukuzawa, Kenji; Shibata, Hirohumi; Higuti, Tomihiko; Honda, Gisho; Ito, Michiho; Khojimatov, Olim K.; Ashurmetov, Ozodbek

doi:10.1021/np0304823

Cited by 45 publications

(30 citation statements)

References 22 publications

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“…In addition, we found that resveratrol 3-(6Љ-galloyl)-O-␤-Dglucopyranoside possessed ILSMR activity, while resveratrol 3-(4Љ-acetyl)-O-␤-D-glucopyranoside did not (26). These results are indicative of a feature common to the molecular structures of all the ILSMRs listed above: a lipophilic portion is connected via an ester linkage to the galloyl group bearing the polar hydroxyl groups.…”

Section: Discussionmentioning

confidence: 68%

Alkyl Gallates, Intensifiers of β-Lactam Susceptibility in Methicillin-Resistant Staphylococcus aureus

Shibata¹,

Kondo²,

Katsuyama³

et al. 2005

Antimicrob Agents Chemother

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We found that ethyl gallate purified from a dried pod of tara (Caesalpinia spinosa) intensified ␤-lactam susceptibility in methicillin-resistant and methicillin-sensitive strains of Staphylococcus aureus (MRSA and MSSA strains, respectively). This compound and several known alkyl gallates were tested with MRSA and MSSA strains to gain new insights into their structural functions in relation to antimicrobial and ␤-lactam susceptibility-intensifying activities. The maximum activity of alkyl gallates against MRSA and MSSA strains occurred at 1-nonyl and 1-decyl gallate, with an MIC at which 90% of the isolates tested were inhibited of 15.6 g/ml. At concentrations lower than the MIC, alkyl gallates synergistically elevated the susceptibility of MRSA and MSSA strains to ␤-lactam antibiotics. Such a synergistic activity of the alkyl gallates appears to be specific for ␤-lactam antibiotics, because no significant changes were observed in the MICs of other classes of antibiotics examined in this study. The length of the alkyl chain was also associated with the modifying activity of the alkyl gallates, and the optimum length was C5 to C6. The present work clearly demonstrates that the length of the alkyl chain has a key role in the elevation of susceptibility to ␤-lactam antibiotics.

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Section: Discussionmentioning

confidence: 68%

Alkyl Gallates, Intensifiers of β-Lactam Susceptibility in Methicillin-Resistant Staphylococcus aureus

Shibata¹,

Kondo²,

Katsuyama³

et al. 2005

Antimicrob Agents Chemother

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“…17 Acetylated derivatives of polyphenols can be found in natural sources such as plants. [18][19][20][21] The ability of acetylated polyphenols to promote tumor cell cycle arrest, death and to sensitize them to other anticancer agents remained to be explored. In the present study, we compare the effects of trans-resveratrol obtained from vine shots (R), the acetylated form of trans-resveratrol (trans-resveratrol triacetate, R3A), the resveratrol oligomer e-viniferin (eV) and its penta-acetate derivative (eV5A) and the vineatrol preparation (Vinea).…”

mentioning

confidence: 99%

Effects of resveratrol analogs on cell cycle progression, cell cycle associated proteins and 5fluoro‐uracil sensitivity in human derived colon cancer cells

Colin

Gimazane

Lizard

et al. 2009

Intl Journal of Cancer

115

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Epidemiological studies suggested that trans-resveratrol, a wine grape component, could prevent malignant tumor development. This compound also demonstrated cytostatic and cytotoxic effects on tumor cells in vitro. To obtain trans-resveratrol derivatives with a better cellular uptake and enhanced antiproliferative effects, we synthesized a triacetate derivative as well as an oligomer, e-viniferin and its acetylated form, e-viniferin penta-acetate. We also obtained vineatrol, a wine grape shoot extract that associates several polyphenols that may act synergistically, including trans-resveratrol and e-viniferin. We show here that resveratrol triacetate and vineatrol are as efficient as trans-resveratrol in inducing the accumulation of human colon cancer cells in early S phase of the cell cycle. This effect is associated with a nuclear redistribution of cyclin A and the formation of a cyclin A/cyclindependent kinase 2 complex whose kinase activity is increased. In contrast, e-viniferin and its acetylated form do not demonstrate any significant activity on these cells when tested alone. Interestingly, resveratrol triacetate and vineatrol dramatically enhance 5-Fluoro-Uracil-mediated inhibition of colon cancer cell proliferation. Thus, acetylated derivatives of resveratrol have retained the cytostatic and cytotoxic activities of the parental molecule and thus deserve to be tested as chemosensitizers in animal models. ' UICCKey words: colon cancer; cell cycle; polyphenols; resveratrol; vineatrol; chemosensitization Epidemiological studies suggested that the polyphenol resveratrol (trans-3,4 0 ,5-trihydroxystilbene) was one of the main wine grape components that protect from vascular diseases, neurodegenerative processes and cancers. 1 The ability of resveratrol to prevent the occurrence of carcinomas was related to the inhibition of tumor cell cycle 2,3 and induction of tumor cell death. 4,5 In addition, there is compelling in vitro evidence that trans-resveratrol behaves as a chemosensitizer when combined with cytotoxic drugs, 6 cytokines 7 and other polyphenols such as quercetin, apigenin and genistein. 8,9 Resveratrol is probably not the only bioactive compound present in the grape wine. Oligomers of resveratrol such as viniferins, were suggested to block the proliferation of several tumoral cell lines 10-12 and a vineatrol preparation containing both trans-resveratrol and e-viniferin exhibited a greater antiproliferative effect on malignant cell lines than each compound tested separately. 13,14 Lipophilic derivatives were obtained through esterification of the hydroxyl functions with aliphatic molecules, which improved their intestinal absorption and cell penetration. 15,16 Acetylation of the phenolic compounds could also favor their absorption, as demonstrated for catechins. 17 Acetylated derivatives of polyphenols can be found in natural sources such as plants. [18][19][20][21] The ability of acetylated polyphenols to promote tumor cell cycle arrest, death and to sensitize them to other anticancer agents remai...

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“…It is usually not known if the analysed samples have been healthy or had been stressed. Resveratrol has also been identified in many medicinal plants, such as Calligonum leucocladum (Okasaka et al, 2004), Cassia quinquangulata, C. garrettiana (Hata et al, 1979;Pezzuto, 2011), Erythropleum lasiantum (Orsini et al, 1997), Ficus barteri fruits (Ogungbamila et al, 1997), Reynoutria japonica (Kimura et al, 1995), Polygonum cuspidatum (Jayatilake et al, 1993;Vastano et al, 2000), and Smilax glabra (Chen et al, 1999). Paul et al (1999) demonstrated that darakshasava, an ayurvedic medicine from India, which main ingredient is Vitis vinifera, contains resveratrol and pterostilbene.…”

Section: Other Products Containing Stilbenesmentioning

confidence: 99%