ABSTRACT
Titanbicus (TB), a hybrid of Hibiscus moscheutos × H. coccineus (Medic.) Walt., has potential to be used as an edible flower. In this study, proximate nutritional content, anthocyanin content, total polyphenol content (TPC), and antioxidant activities in vitro and in vivo were investigated. Three cultivars of TB, namely Artemis (AR), Rhea (R), and Adonis (AD), were used as materials. Protein and carbohydrates were the primary macronutrients, while crude fat and ash were detected in trace amounts. Cyanidin 3-glucoside (Cy3-G) and cyanidin 3-sambubioside (Cy3-Sam), were identified in all TBs. The highest anthocyanin content was observed in AD (47.09 ± 1.45 mg/g extract), followed by R and AR (6.04 ± 0.20 and 2.72 ± 0.11 mg/g extract, respectively). The TPC of AD (225.01 ± 1.97 mg/g extract) was greater than that of AR and R (185.41 ± 3.24 and 144.10 ± 1.71 mg/g extract, respectively). AD exhibited the strongest in vitro antioxidant activity in hydrophilic oxygen radical absorbance capacity, compared to the other two TBs. In addition, AD extract suppressed the generation of reactive oxygen species in caudal fin of wounded zebrafish. Antioxidant activities of AD appeared to be related to its total anthocyanin content, Cy3-G, Cy3-Sam, and TPC. Our findings indicate that TB, particularly the AD cultivar, would be an attractive source of bioactive compounds with antioxidant activities, and can improve both nutritional value and appearance of food.
Subject(s)
Anthocyanins , Hibiscus , Antioxidants , Flowers , Plant Extracts , PolyphenolsABSTRACT
The blue sepal color of hydrangea is due to a metal complex anthocyanin composed of 3-O-glucosyldelphinidin (1) and an aluminum ion with the co-pigments 5-O-caffeoylquinic acid (2) and/or 5-O-p-coumaroylquinic acid (3). The three components, namely anthocyanin, Al3+ and 5-O-acylquinic acids, are essential for blue color development, but the complex is unstable and only exists in an aqueous solution. Furthermore, the complex did not give analyzable NMR spectra or crystals. Therefore, many trials to determine the detailed chemical structure of the hydrangea-blue complex have not been successful to date. Instead, via experiments mixing 1, Al3+ and 2 or 3 in a buffered solution at pH 4.0, we obtained the same blue solution derived from the sepals. However, the ratio was not stoichiometric but fluctuated. To determine the composition of the complex, we tried direct observation of the molecular ion of the complex using electrospray-ionization mass spectrometry. In a very low-concentration buffer solution (2.0 mM) at pH 4.0, we reproduced the hydrangea-blue color by mixing 1, 2 and Al3+ in ratios of 1:1:1, 1:2:1 and 1:3:1. All solution gave the same molecular ion peak at m/z = 843, indicating that the blue solution has a ratio of 1:1:1 for the complex. By using 3, the observed mass number was m/z = 827 and the ratio of 1, 3 and Al3+ was also 1:1:1. A mixture of 1, 3-O-caffeoylquinic acid (4) and Al3+ did not give any blue color but instead was purple, and the intensity of the molecular ion peak at m/z = 843 was very low. These results strongly indicate that the hydrangea blue-complex is composed of a ratio of 1:1:1 for 1, Al3+ and 2 or 3.
Subject(s)
Aluminum/isolation & purification , Anthocyanins/isolation & purification , Chlorogenic Acid/analogs & derivatives , Coumarins/isolation & purification , Glucosides/isolation & purification , Hydrangea/chemistry , Quinic Acid/analogs & derivatives , Aluminum/chemistry , Anthocyanins/chemistry , Chlorogenic Acid/chemistry , Chlorogenic Acid/isolation & purification , Coumarins/chemistry , Flowers/chemistry , Glucosides/chemistry , Hydrogen-Ion Concentration , Molecular Structure , Plant Extracts/chemistry , Quinic Acid/chemistry , Quinic Acid/isolation & purification , Spectrometry, Mass, Electrospray IonizationABSTRACT
penia-O-Methylquercetin (2) was prepared by permethylation of quercetin (1). Selective demethylation of 2 using either BBr or BCl3/TBAI (tetrabutylammonium iodide) gave five O-methylquercetins (3-6), with satisfactory yields. The reaction can be easily scaled-up. We established an efficient and large-scale preparation of O-methylquercetins.
Subject(s)
Quercetin/analogs & derivatives , Boranes/chemistry , Boron Compounds/chemistry , Bromides/chemistry , Chlorides/chemistry , Demethylation , Molecular Structure , Quaternary Ammonium CompoundsABSTRACT
Polyphenols are major plant secondary metabolites, structurally extremely diverse, essential for a variety of functions in plants, responsible for major organoleptic and nutritional properties of plant-derived foods, and useful for numerous practical applications. During the 27th International Conference on Polyphenols and 8th Tannin Conference, held jointly in September 2014 in Nagoya, Japan (ICP2014), the latest advances in polyphenol research have been presented. These include advances in polyphenol chemistry, physicochemistry, and materials science; their biosynthesis, genetics, and metabolic engineering; and their role in plant interactions with the environment, in nutrition and health, and in natural medicine. This special issue presents a selection of research papers presented at the meeting, covering these different fields. Major recent progress and perspectives in these areas are also outlined in this introductory paper.
Subject(s)
Plant Extracts/chemistry , Plants, Edible/chemistry , Polyphenols/chemistry , Animals , Humans , Plant Extracts/metabolism , Plant Extracts/pharmacology , Plants, Edible/genetics , Plants, Edible/metabolism , Polyphenols/metabolism , Polyphenols/pharmacologyABSTRACT
Aminopiperidine derivatives, Compound 1a and 1b, are novel small molecules that inhibit C-14 reduction catalyzed by Erg24p in ergosterol synthesis of Candida albicans. We evaluated the properties of the in vitro and in vivo activities of these compounds against pathogenic fungi and compared their activities with those of fluconazole. Compound 1a and 1b exhibited potent in vitro activities against clinically important fungi such as Candida species, including both of fluconazole-resistant strains of C. albicans and non-albicans Candida, Aspergillus fumigatus, and Cryptococcus neoformans. Against C. albicans, its mode of action was fungistatic. Furthermore, orally administered Compound 1b clearly prolonged the survival of infected mice in systemic lethal infection caused by C. albicans. These results suggest that aminopiperidine derivative is a promising lead compound for an orally available novel antifungal drug with a broad spectrum.
Subject(s)
Antifungal Agents/therapeutic use , Candida albicans/drug effects , Candidiasis/drug therapy , Ergosterol/antagonists & inhibitors , Fluconazole/pharmacology , Fungi/drug effects , Piperidines/therapeutic use , Animals , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Candidiasis/microbiology , Female , Inhibitory Concentration 50 , Kaplan-Meier Estimate , Mice , Microbial Sensitivity Tests , Molecular Structure , Piperidines/chemistry , Piperidines/pharmacologyABSTRACT
Blue color in flowers is due mainly to anthocyanins, and a considerable part of blue coloration can be attributed to metal-complexed anthocyanins. However, the mechanism of metal ion transport into vacuoles and subsequent flower color development has yet to be fully explored. Previously, we studied the mechanism of blue color development specifically at the bottom of the inner perianth in purple tulip petals of Tulipa gesneriana cv. Murasakizuisho. We found that differences in iron content were associated with the development of blue- and purple-colored cells. Here, we identify a vacuolar iron transporter in T. gesneriana (TgVit1), and characterize the localization and function of this transporter protein in tulip petals. The amino acid sequence of TgVit1 is 85% similar that of the Arabidopsis thaliana vacuolar iron transporter AtVIT1, and also showed similarity to the AtVIT1 homolog in yeast, Ca(2+)-sensitive cross-complementer 1 (CCC1). The gene TgVit1 was expressed exclusively in blue-colored epidermal cells, and protein levels increased with increasing mRNA expression and blue coloration. Transient expression experiments revealed that TgVit1 localizes to the vacuolar membrane, and is responsible for the development of the blue color in purple cells. Expression of TgVit1 in yeast rescued the growth defect of ccc1 mutant cells in the presence of high concentrations of FeSO(4). Our results indicate that TgVit1 plays an essential role in blue coloration as a vacuolar iron transporter in tulip petals. These results suggest a new role for involvement of a vacuolar iron transporter in blue flower color development.
Subject(s)
Anthocyanins/metabolism , Cation Transport Proteins/metabolism , Iron/metabolism , Plant Proteins/metabolism , Tulipa/genetics , Amino Acid Sequence , Cation Transport Proteins/genetics , Cloning, Molecular , DNA, Complementary/genetics , Ferrous Compounds/metabolism , Flowers/metabolism , Gene Expression Regulation, Plant , Molecular Sequence Data , Pigmentation/genetics , Plant Proteins/genetics , Plants, Genetically Modified/genetics , Plants, Genetically Modified/metabolism , RNA, Plant/genetics , Sequence Alignment , Tulipa/metabolism , Vacuoles/metabolismABSTRACT
A series of 4-oxo-4H-pyrido[1,2-a]pyrimidine derivatives, substituted at the 2-position with piperidines bearing quaternary ammonium salt side chains, were synthesized and evaluated for their ability to potentiate the activity of the fluoroquinolone levofloxacin (LVFX) and the beta-lactam aztreonam (AZT) in Pseudomonas aeruginosa. Attachment of the charged entity using an N-ethylcarbamoyloxy linker led to the discovery of the highly soluble compound 22 (D13-9001), which maintained good potency in vitro and displayed excellent activity in vivo in a rat pneumonia model of P. aeruginosa.