• Korean Journal of Pharmacognosy
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• 제42권3호
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• pp.229-232
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• 2011

Three dihydrochalcone compounds were isolated from the twigs of Stewartia koreana (Theaceae) through repeated column chromatography. Their chemical structures were elucidated as phloridizin, 2',4,4'-trihydroxy-6'-methoxydihydrochalcone and confusoside, respectively, by spectroscopic analysis. These compounds were isolated for the first time from this plant.

• Bulletin of the Korean Chemical Society
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• 제29권6호
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• pp.1199-1204
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• 2008

The efficient and concise total syntheses of naturally occurring dihydrochalcone nicolaioidesin C, crinatusin C1, and crinatusin $C_2$ have been achieved from the readily available 2,6-dihydroxy-4-methoxyacetophenone and 2,4-dihydroxy-6-methoxyacetophenone. The key steps in the synthetic strategy were aldol reaction and Diels-Alder reaction.

• Bulletin of the Korean Chemical Society
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• 제6권1호
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• pp.7-11
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• 1985

The crystal structure of phlorizin, a ${\beta}$ -D-glucopyranoside of a flavonoid dihydrochalcone phloretin, has been determined by single crystal diffraction methods using diffractometer data obtained by the ${\omega}-2{\theta}$ scan technique with Cu $K{\alpha}$ radiation from a crystal with space group symmetry $P2_12_12_1$ and unit cell parameters a = 4.9094 (2), b = 19.109 (1), c = 23.275 (4) $\AA$. The structure was solved by direct methods and refined by full-matrix least-squares to a final R = 0.047 for the 1697 observed reflections. The dihydrochalcone moiety is flat and fully extended. The glucose ring has the $^4C_1$ chair conformation and the conformation of the primary alcohol group is gauche-gauche. The crystal packing is dominated by an extensive hydrogen bonding pattern. There are one strong and two weak intramolecular hydrogen bonds in the phlorizin molecule.

• Preventive Nutrition and Food Science
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• 제1권2호
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• pp.186-189
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• 1996

Neohesperidin dihydrochalcone(NHDC) is an intense sweetener with lingering aftertaste, which limits NHDC to use as a sweetener in food products. This study was conducted to examine the changes of teste quality of NHDC when using $\beta$-cyclodextrin($\beta$-CD) as a taste modifier. A series of $\beta$-CD(0.01%, 0.03%, 0.1%, 0.176%) was added to NHDC solution (100ppm) and the taste quality was evaluated by magnitude estimation. It was found that $\beta$-CD produced a significant effect in the reduction of aftertaste of NHDC(p<0.01) and sweetness as well.(p<0.001). Linear regression(log mean magnitude estimate versus $\beta$-CD concentration) analysis showed that the intensity of sweetness(n=-0.31) decreased more rapidly than that of aftertaste(m=-0.17). This result suggests the possibility that $\beta$-CD may form inclusion complex with NHDC, so that the hydrophobic portion is encapsulated in the cavity of $\beta$-CD and the carbohydrate moiety is oriented to the outside of the cavity. Or it may be that $\beta$-CD competes with the NHDC molecule for binding to the taste receptor, resulting in reduced perceived intensity.

• Journal of the Korean Chemical Society
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• 제30권2호
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• pp.259-262
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• 1986

• Preventive Nutrition and Food Science
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• 제2권4호
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• pp.291-295
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• 1997

Some sensory properties of synthetic sweeteners are limiting factors for use in low calorie foods of soft drinks. By combining synthetic sweeteners(Neohesperidin dihydrochacone(NHDC), stevioside) with sucrose, sorbitol or xylitol, these limitations can be overcome. Using trained taste panelists and magnitude estimation methods, synergistic effects were investigated in binary sweetener mixtures, The results showed that synergism, as much as 28% to 69%,was noted at all concentration in xylitol-stevioside, NHDC-stevioside mixtures. Synergistic effects were found only at high concentration levels in mixtures of sucrose-NHDC, sucrose-stevioside, and sorbitol-stevioside, ranging from 11% to 22%.By taking advantage of synergistic effects, ginseng tea and orange flavored beverages, sweetened with either xylitol-stevioside of NHDC-stevioside, were prepared and the sensory quality was compared with that of sucrose containing beverages. It was found that sensory characteristics were judged to be very similar for all formulations. The result suggests the possibility of using of using these sweetener mixtures as sugar substitutes in ginseng tea and orange drink.

• Korean Journal of Pharmacognosy
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• 제24권4호
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• pp.282-288
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• 1993

Very little utilization of the fruits of Malus baccata(Rosaceae) has been employed for food and medicinal plants except for preparing fruit beverages. But, it was estimated as valuable to investigate the chemical components for the botanical resource of this plant. In this study, it was found that the fruits of this plant contained primary long chain alcohol, ${\beta}-sitosterol$, campesterol, ursolic acid and ${\beta}-_D-glucosides$ of ${\beta}-sitosterol$ and campesterol. However, phloretin(dihydrochalcone) and its 5-O-glucoside(phloridzin) known as plant growth regulators in many Rosaceae plants were not found in this plant material by co-TLC analysis with authentic specimens. Although plant sex hormone, estrone, was often contained in relates of M. baccata, e.g., Prunus spp., Crataegus spp. and Malus spp., this compound was not detected in this fruit by comparison with an authentic material. By RIC chromatography, it was suggested that the Soxhlet extraction by the solvent of ether was excellently useful to extract ursolic acid efficiently.

• Journal of Microbiology and Biotechnology
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• 제31권10호
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• pp.1409-1419
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• 2021

A growing number of healthy dietary ingredients in fruits and vegetables have been shown to exhibit diverse biological activities. Phloretin, a dihydrochalcone flavonoid that is abundant in apples and pears, has anti-inflammatory effects on ulcerative colitis (UC) mice. The gut microbiota and metabolism are closely related to each other due to the existence of the food-gut axis in the human colon. To investigate the interplay of faecal metabolites and the microbiota in UC mice after phloretin treatment, phloretin (60 mg/kg) was administered by gavage to ameliorate dextran sulfate sodium (DSS)-induced UC in mice. Gut microbes and faecal metabolite profiles were detected by high-throughput sequencing and liquid chromatography mass spectrometry (LC-MS) analysis, respectively. The correlations between gut microbes and their metabolites were evaluated by Spearman correlation coefficients. The results indicated that phloretin reshaped the disturbed faecal metabolite profile in UC mice and improved the metabolic pathways by balancing the composition of faecal metabolites such as norepinephrine, mesalazine, tyrosine, 5-acetyl-2,4-dimethyloxazole, and 6-acetyl-2,3-dihydro-2-(hydroxymethyl)-4(1H)-pyridinone. Correlation analysis identified the relations between the gut microbes and their metabolites. Proteus was negatively related to many faecal metabolites, such as norepinephrine, L-tyrosine, laccarin, dopamine glucuronide, and 5-acetyl-2,4-dimethyloxazole. The abundance of unidentified Bacteriodales_S24-7_group was positively related to ecgonine, 15-KETE and 6-acetyl-2,3-dihydro-2-(hydroxymethyl)-4(1H)-pyridinone. The abundance of Christensenellaceae_R-7_group was negatively related to the levels of 15-KETE and netilmicin. Stenotrophomonas and 15-KETE were negatively related, while Intestinimonas and alanyl-serine were positively related. In conclusion, phloretin treatment had positive impacts on faecal metabolites in UC mice, and the changes in faecal metabolites were closely related to the gut microbiota.