Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana

Kondo, Yoko; Shimoda, Kei; Miyahara, Keiichi; Hamada, Hatsuyuki; Hamada, Hiroki

doi:10.5511/plantbiotechnology.23.291

Cited by 15 publications

(11 citation statements)

References 17 publications

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“…americana cells were subcultured at four-week intervals for two months on solid Murashige and Skoog medium (MS; 100 mL in a 300-mL conical flask) containing 3% sucrose, 10 mM 2,4-dichlorophenoxyacetic acid, and 1% agar (adjusted to pH 5.7) at 25°C. [23][24][25][26][27][28][29] A suspension culture was started by transferring the cultured cells to 100 mL of liquid medium in a 300-mL conical flask, and incubated on a rotary shaker (120 rpm) at 25°C. Prior to use in this work, some of the callus tissue (fresh weight (fr.…”

Section: Analysesmentioning

confidence: 99%

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Uesugi

Hamada

Shimoda

et al. 2017

Bioscience, Biotechnology, and Biochemistry

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The stilbene compound resveratrol was glycosylated to give its 4'-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4'-O-β-D-glucoside, and converted pinostilbene to its 4'-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.

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Section: Analysesmentioning

confidence: 99%

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Uesugi

Hamada

Shimoda

et al. 2017

Bioscience, Biotechnology, and Biochemistry

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“…Microalgae, which are at the base of the food web in most aquatic environments, can metabolise BPA to form glycosides, which in turn may be digested to BPA by b-glucosidases in the animal intestine (Nakajima et al 2007). Processes such as hydroxylation, oxidation and glycosylation of BPA occur in higher plants (Hamada et al 2001;Xuan et al 2002;Kondo et al 2006). Experimental data collected for many plant species, from both cell culture and whole plant systems, show that they are able to take up, transform, accumulate and translocate BPA (Nakajima et al 2002(Nakajima et al , 2005Morohoshi et al 2003;Ferrara et al 2006).…”

Section: Introductionmentioning

confidence: 99%

The environmental endocrine disruptor, bisphenol A, affects germination, elicits stress response and alters steroid hormone production in kiwifruit pollen

et al. 2010

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In vitro toxicity of the endocrine disruptor bisphenol A (BPA) to pollen, the male haploid generation of higher plants, was studied. BPA caused significant inhibition of both tube emergence and elongation of kiwifruit pollen in a dose-dependent manner, beginning at 10 mg · l(-1); morphological changes to tubes were also detected. Despite strong inhibition of pollen tube production and growth, a large percentage of treated cells remained viable. Immunoblotting experiments indicated that levels of BiP and 14-3-3, which are proteins involved in stress response, substantially increased in BPA-treated pollen compared to controls. The increases were dose-dependent in the range 10-50 mg · l(-1) BPA, i.e. even when germination ability was completely blocked. Steroid hormones (17 β-estradiol, progesterone and testosterone) were detected in kiwifruit pollen, and their levels increased during germination in basal medium. In a BPA treatment of 30 mg · l(-1), larger increases in both estrogen and testosterone concentrations were detected, in particular, a six-fold increase of 17 β-estradiol over control concentration (30 min). The increased hormone levels were maintained for at least the 90 min incubation. Increasing concentrations of exogenous testosterone and 17 β-estradiol increasingly inhibited pollen tube emergence and elongation. Current data for BPA-exposed kiwifruit pollen suggest a toxicity mechanism that is at least in part based on a dramatic imbalance of steroid hormone production during tube organisation, emergence and elongation. It may be concluded that BPA, a widespread environmental contaminant, can cause serious adverse effects to essential pollen functions. On a broader scale, this chemical poses a potential risk to the reproductive success of higher plants.

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“…Many of these secondary metabolites have specific physiological activities and have been widely used in folk medicines [2]. Therefore, the glycosylation of organic compounds by biocatalysts is of pharmaceutical importance and has been carried out for many exogenous compounds [2][3][4][5][6][7][8]. Although studies on physiological properties of (+)--viniferin have been reported [1], there are few reports on glycosylation of (+)--viniferin by biocatalysts.…”

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confidence: 99%

Synthesis of ε-Viniferin Glycosides by Glucosyltransferase from Phytolacca americana and their Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells

Hamada

Shimoda

2015

Natural Product Communications

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Regioselective hydroxylation, reduction, and glycosylation of diphenyl compounds by cultured plant cells of Eucalyptus perriniana

Cited by 15 publications

References 17 publications

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

The environmental endocrine disruptor, bisphenol A, affects germination, elicits stress response and alters steroid hormone production in kiwifruit pollen

Synthesis of ε-Viniferin Glycosides by Glucosyltransferase from Phytolacca americana and their Inhibitory Activity on Histamine Release from Rat Peritoneal Mast Cells

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