The enhancement of isoflavones water solubility by complexation with modified cyclodextrins: A spectroscopic investigation with implications in the pharmaceutical analysis

Stancanelli, Rosanna; Mazzaglia, Antonino; Tommasini, S.; Calabrò, Marco; Villari, Valentina; Guardo, M.; Ficarra, P.; Ficarra, R.

doi:10.1016/j.jpba.2007.03.025

Cited by 64 publications

(41 citation statements)

References 14 publications

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“…5), including much higher concentrations of biochanin A, calycosin, and prunetin than in other treatments (Fig. 6) and also higher concentrations of the nonglucoside and less water-soluble (Stancanelli et al 2007) isoflavones genistein, daidzein, and glycitein. Biochanin A (Shajib 2012) and daidzein (Tamura et al 1969) can inhibit plant growth, while genistein can inhibit root absorption of nutrients (Stenlid 1961); the allelochemical effects of the other compounds have been poorly investigated.…”

Section: Microbial Interactions With Solid Residue Fractionsmentioning

confidence: 79%

Interactions between allelochemicals and the microbial community affect weed suppression following cover crop residue incorporation into soil

Lou

Davis²,

Yannarell

2015

Plant Soil

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Background and aims The objective of this study is to understand how soil microorganisms interact with cover crop-derived allelochemicals to suppress weed germination and growth following cover crop residue incorporation. Methods We conducted a time series experiment crossing sterilized and non-sterilized soil with four different residue treatments. We measured weed seed germination rates, radicle elongation, and disease incidence in seed germination bioassays. We also monitored cover crop-derived, isoflavone allelochemicals in these bioassays. We partitioned the total weed suppression into three sources: microbe-only inhibition, residue-only inhibition, and the microbe-residue interaction. Results Microbial activity suppressed weed germination and growth for 30 days, while cover crop-derived allelochemicals provided suppression for a limited time. There was an antagonistic interaction between microbes and allelochemicals. This interaction was strongest for water-soluble allelochemicals, while residue fractions containing intact plant tissues retained greater suppressiveness even in the presence of a live microbial community. Conclusions Microbial activity can directly suppress weed germination and growth, but microorganisms also indirectly help weeds by degrading cover crop-derived allelochemicals. As a result of these interactions, cover crop-derived weed suppression in agricultural soils shifts from an early allelochemical-dominated phase to a later phase where microbial suppression is more important.

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Section: Microbial Interactions With Solid Residue Fractionsmentioning

confidence: 79%

Interactions between allelochemicals and the microbial community affect weed suppression following cover crop residue incorporation into soil

Lou

Davis²,

Yannarell

2015

Plant Soil

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“…Resveratrol can induce deacetylation of PGC-1␣ (2) and AMP-activated protein kinase activation (2), which are potential mechanisms for PGC-1␣ activation. Both resveratrol and genistein are relatively insoluble in water, and increasing its water solubility does not increase resveratrol absorption (67), although genistein bioavailability can be increased by complexing genistein with cyclodextrins (68). In contrast, PQQ is relatively water-soluble (Ͼ1 g of PQQ/liter of water) and is easily absorbed at low dietary concentrations intakes (69).…”

Section: Discussionmentioning

confidence: 99%

Pyrroloquinoline Quinone Stimulates Mitochondrial Biogenesis through cAMP Response Element-binding Protein Phosphorylation and Increased PGC-1α Expression

Chowanadisai

Bauerly

Tchaparian

et al. 2010

Journal of Biological Chemistry

194

172

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Bioactive compounds reported to stimulate mitochondrial biogenesis are linked to many health benefits such increased longevity, improved energy utilization, and protection from reactive oxygen species. Previously studies have shown that mice and rats fed diets lacking in pyrroloquinoline quinone (PQQ) have reduced mitochondrial content. Therefore, we hypothesized that PQQ can induce mitochondrial biogenesis in mouse hepatocytes. Exposure of mouse Hepa1-6 cells to 10 -30 M PQQ for 24 -48 h resulted in increased citrate synthase and cytochrome c oxidase activity, Mitotracker staining, mitochondrial DNA content, and cellular oxygen respiration. The induction of this process occurred through the activation of cAMP response element-binding protein (CREB) and peroxisome proliferator-activated receptor-␥ coactivator-1␣ (PGC-1␣), a pathway known to regulate mitochondrial biogenesis. PQQ exposure stimulated phosphorylation of CREB at serine 133, activated the promoter of PGC-1␣, and increased PGC-1␣ mRNA and protein expression. PQQ did not stimulate mitochondrial biogenesis after small interfering RNA-mediated reduction in either PGC-1␣ or CREB expression. Consistent with activation of the PGC-1␣ pathway, PQQ increased nuclear respiratory factor activation (NRF-1 and NRF-2) and Tfam, TFB1M, and TFB2M mRNA expression. Moreover, PQQ protected cells from mitochondrial inhibition by rotenone, 3-nitropropionic acid, antimycin A, and sodium azide. The ability of PQQ to stimulate mitochondrial biogenesis accounts in part for action of this compound and suggests that PQQ may be beneficial in diseases associated with mitochondrial dysfunction.Bioactive compounds, such as pyrroloquinoline quinone (PQQ), 2 resveratrol, genistein, hydroxy-tyrosol, and quercetin have been reported to improve mitochondrial respiratory control or stimulate mitochondrial biogenesis (1-5), which is potentially important to a number of health-related issues ranging from increased longevity, improved energy utilization, and protection from reactive oxygen species (6 -8). Furthermore, mitochondrial DNA depletion and mutations are associated with cardiomyopathy, lactic acidosis, developmental delay, failure to thrive, and impaired neurological function (9). The response to most biofactors is observed after pharmacological intervention or dietary supplementation, although often neargram amounts per kg of diet, or millimolar quantities, are needed for such responses in vivo. PQQ stimulates mitochondriogenesis with the addition of only milligram quantities of PQQ per kg of diet, or micromolar concentrations, in vivo. For example, PQQ deprivation depresses mitochondrial function, which is reversed when as little as 200 -300 g of PQQ/kg of diet are added (1, 10). PQQ also remains detectable in tissues when there is no or little dietary exposure (11), which has not been observed for other dietary polyphenolic compounds known to promote mitochondriogenesis.Recently, PQQ produced by rhizobacterium has been identified as an important plant growth factor (12) and is a...

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“…However, its activities are conditioned to the aglicone form, which presents reduced aqueous solubility. 7,8 This fact limits its application in the pharmaceutical field and the complexation of this isoflavone with cyclodextrins (CDs) has emerged as an interesting alternative for the improvement of GEN aqueous solubility. CDs are cyclic oligosaccharides consisting of variable glucopyranose units linked by a-(1,4) bonds, with relative water solubility.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13] The association of GEN with CDs was firstly investigated by Crupi et al, 7 who performed phase-solubility studies with β-CD, hydroxypropyl-β-CD and methyl-β-CD and employed FTIR-ATR in the analysis of the 1:1 solid complexes obtained by co-precipitation method. In the same way, Stancanelli et al 8 prepared GEN/ hydroxypropyl-β-CD complexes in liquid media followed by UV-VIS spectrophotometry and circular dichroism analysis. More recently, Daruházi et al 14 reported the obtention of GEN/β-CD complexes employing kneading method.…”

Section: Introductionmentioning

confidence: 99%

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

et al. 2010

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Recebido em 17/3/09; aceito em 7/9/09; publicado na web em 23/2/10 Genistein:β-cyclodextrin complexes with high drug loading (19.22%) were prepared by freeze-drying and characterized by differential scanning calorimetry and hydrogen nuclear magnetic resonance spectroscopy. The spatial configuration of the complex was proposed by means of 2D-NOESY experiment combined with molecular modeling. According to the results obtained, the interaction of genistein with β-cyclodextrin in a 1:1 complex is supposed to occur mainly through the insertion of the guest A-ring in cyclodextrin cavity, without rule out the possibility of inclusion through the B-ring, as previously reported in the literature.

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The enhancement of isoflavones water solubility by complexation with modified cyclodextrins: A spectroscopic investigation with implications in the pharmaceutical analysis

Cited by 64 publications

References 14 publications

Interactions between allelochemicals and the microbial community affect weed suppression following cover crop residue incorporation into soil

Interactions between allelochemicals and the microbial community affect weed suppression following cover crop residue incorporation into soil

Pyrroloquinoline Quinone Stimulates Mitochondrial Biogenesis through cAMP Response Element-binding Protein Phosphorylation and Increased PGC-1α Expression

Improvement of genistein content in solid genistein/-cyclodextrin complexes β

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