Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by <i>trans</i>‐resveratrol methyl ethers

Mikstacka, Renata; Przybylska, Dorota; Rimando, Agnes M.; Baer‐Dubowska, Wanda

doi:10.1002/mnfr.200600135

Cited by 99 publications

(66 citation statements)

References 44 publications

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“…RME was purified using preparative TLC and HPLC, and characterized by GC-MS). RME characteristics corresponded to published data (l max 307 nm, 320 nm in 50% acetonitrile, ion at m/z 242; Katsuyama et al, 2007;Mikstacka et al, 2007). HPLC-grade solvents (acetonitrile, methanol) were from Merck and used in combination with sterilized water from Aguettant.…”

Section: Chemicals and Radiochemicalsmentioning

confidence: 87%

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

et al. 2008

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Stilbenes are considered the most important phytoalexin group in grapevine (Vitis vinifera) and they are known to contribute to the protection against various pathogens. The main stilbenes in grapevine are resveratrol and its derivatives and, among these, pterostilbene has recently attracted much attention due both to its antifungal and pharmacological properties. Indeed, pterostilbene is 5 to 10 times more fungitoxic than resveratrol in vitro and recent studies have shown that pterostilbene exhibits anticancer, hypolipidemic, and antidiabetic properties. A candidate gene approach was used to identify a grapevine resveratrol O-methyltransferase (ROMT) cDNA and the activity of the corresponding protein was characterized after expression in Escherichia coli. Transient coexpression of ROMT and grapevine stilbene synthase in tobacco (Nicotiana benthamiana) using the agroinfiltration technique resulted in the accumulation of pterostilbene in tobacco tissues. Taken together, these results showed that ROMT was able to catalyze the biosynthesis of pterostilbene from resveratrol both in vitro and in planta. ROMT gene expression in grapevine leaves was induced by different stresses, including downy mildew (Plasmopara viticola) infection, ultraviolet light, and AlCl 3 treatment.

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Section: Chemicals and Radiochemicalsmentioning

confidence: 87%

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

et al. 2008

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“…5). In addition to chemopreventive activity, methylated resveratrols, such as desoxyrhapontigenin (4Ј-O-methylresveratrol) and pinostilbene (1k: 3-O-methyl-resveratrol), exhibit higher CYP1A1 inhibitory activity than resveratrol (2f) [52]. Furthermore, a pinosylvin monomethyl ether (1k) as a nematicidal agent from Pinus massoniana shows a tentimes smaller LC 50 value than pinosylvin (1f) [53].…”

Section: -2 Production Of Stilbene Methyl Ethersmentioning

confidence: 99%

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

Horinouchi

2008

J Antibiot

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One of the approaches of combinatorial biosynthesis is combining genes from different organisms and designing a new set of gene clusters to produce bioactive compounds, leading to diversification of both chemical and natural product libraries. This makes efficient use of the potential of the host organisms, especially when microorganisms are used. An Escherichia coli system, in which artificial biosynthetic pathways for production of plant-specific medicinal polyketides, such as flavonoids, stilbenoids, isoflavonoids, and curcuminoids, are assembled, has been designed and expressed. Starting with amino acids tyrosine and phenylalanine as substrates, this system yields naringenin, resveratrol, genistein, and curcumin, for example, all of which are beneficial to human health because of their wide variety of biological activities. Supplementation of unnatural carboxylic acids to the recombinant E. coli cells carrying the artificial pathways by precursor-directed biosynthesis results in production of unnatural compounds. Addition of decorating or modification enzymes to the artificial pathway leads to production of natural and unnatural flavonols, flavones, and methylated resveratrols. This microbial system is promising for construction of larger libraries by employing other polyketide synthases and decorating enzymes of various origins. In addition, the concept of building and expressing artificial biosynthetic pathways for production of non-bacterial and unnatural compounds in microorganisms should be successfully applied to production of not only plant-specific polyketides but also many other useful compound classes.

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“…그러나 quercetin 자체는 생물 이용 성이 낮아 급여시 그 이용이 제한적이다. 이는 hydroxylated flavonoids인 quercetin이 혈액이나 장기에 도달하기 전에 in vivo 상태에서 신속하게 대사되어 배설되고 transcellular 수 송이 낮은 단점이 있기 때문이다 (Lee et al, 2011;Suresh Babu et al, 2004;Mikstacka et al, 2007). 이를 보완하기 위해 수 산화기를 메틸기로 치환함으로써 (methoxylation) 친수성인 quercetin의 지용성을 증가시키고, 음이온을 띠게 하여 대사 안정성과 세포내 수송율을 높일 수 있다 (Graf et al, 2005;Wilson et al, 2008).…”

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Effect of Quercetin and Methoxylated Quercetin on Chicken Thigh Meat Quality during Cold Storage

Jang¹,

Ham²,

Chae³

et al. 2011

Korean Journal of Poultry Science

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This study was carried out to determine the effect of dietary supplementation of quercetin and methoxylated quercetin extracted from onions on chicken thigh meat quality during cold storage. For 35 days, 1-day-old 320 broiler chicks (Ross) were divided into 8 groups and supplemented the diet; basal diet only (CONTROL), CONTROL with antibiotics (AB), vitamin E 20 IU (VE20), vitamin E 200 IU (VE200), quercetin 20 ppm (QC20), quercetin 200 ppm (QC200), methoxylated quercetin 20 ppm (MQ20), and methoxylated quercetin 200 ppm (MQ200). After slaughtering the broilers, thighs were separated and analyzed the quality change of the meat during storage at 4℃ for 7 days. The meat quality factors such as pH, color, water holding capacity, and sensory characteristics of thigh meat were determined on the experiment day 0, 3, and 7. After slaughtering, the pH of AB, VE 20, QC 20, and MQ 200 showed no significant difference compare to that of CONTROL. However, VE 200 and QC 20 showed higher pH value than CONTROL on storage day 3. L* value of chicken thigh of MQ 20 was lower than CONTROL on storage day 0, however, no significant difference was found between CONTROL and treatments on storage day 3. Redness (a*) of chicken thigh in CONTROL was increased during storage. QC 20, QC 200, and MQ 200 significantly reduced the b* value of chicken thigh (p<0.05). Water holding capacity of VE 20 and MQ 200 was significantly higher than the CONTROL on the day 0. Also, QC 200 showed higher WHC compare to the CONTROL. In sensory evaluation, overall acceptability of chicken thigh in quercetin and methoxylated quercetin group showed no significant differences compare to that of CONTROL by storage day 3. These results suggested that the quercetin and methoxylated quercetin could be used as additives to enhance broiler thigh meat quality such as pH and WHC without adverse effect on color and sensory characteristics.

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Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans‐resveratrol methyl ethers

Cited by 99 publications

References 44 publications

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

A Stress-Inducible Resveratrol O-Methyltransferase Involved in the Biosynthesis of Pterostilbene in Grapevine

Combinatorial Biosynthesis of Non-bacterial and Unnatural Flavonoids, Stilbenoids and Curcuminoids by Microorganisms

Effect of Quercetin and Methoxylated Quercetin on Chicken Thigh Meat Quality during Cold Storage

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