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RSC Advances · 2015 ·Vol. 5 ·期 58 ·46598-46607 · IF 3.84

Ultrasonic-assisted extraction of pigments from Hylocereus undatus flowers: optimization, antioxidant activity, and HPLC analysis

Yong Liu,Huifang Zhang,Shoulian Wei

The ultrasonic-assisted extraction of pigments from the Hylocereus undatus flowers was modeled using response surface methodology. A three-level, three-factor Box–Behnken design was employed to optimize three extraction variables, including liquid–solid ratio (X1), extraction time (X2), and ethanol concentration (X3), for the achievement of high absorbance. The statistical analysis shows that the model is significant to optimize the extraction variables (p < 0.01), and the independent variable (X3) and the quadratic term (X32) have a significant effect on the absorbance (p < 0.01). The optimized conditions are X1 of 42 : 1 mL g−1, X2 of 33.2 min, and X3 of 77.5%. Under these conditions, the experimental absorbance is 2.240 ± 0.095% (n = 3), which is in good agreement with the predicted value of 2.243. The evaluation of antioxidant activity by DPPH and hydroxyl free radicals, reducing power, and metal chelating ability indicate that the pigments from the H. undatus flowers possess significant antioxidant activity. HPLC analysis reveals that gallic acid, rutin, quercetin, kaempferol and isorhamnetin are the major components in the pigments.

研究领域: 植物化学 · 食品科学 · 分析化学
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PLANT PHYSIOLOGY AND BIOCHEMISTRY · 2021 · IF 4.27

CsUGT78A15 catalyzes the anthocyanidin 3-O-galactoside biosynthesis in tea plants

Xuqiu He,Ronghao Huang,Lipeng Liu,Yingying Li,Wenzhao Wang,Qingshan Xu,Youben Yu,Tianshan Zhou

Anthocyanins are a group of natural water-soluble pigments in plants that contribute to the pink-purple color of a range of tissues. Because anthocyanins have various biological activities in human health, there is great research interest in the development of anthocyanin-rich foods and beverages, including purple shoot tea. Anthocyanidin 3- O -galactosides have been identified as one of the main anthocyanin components in purple shoot tea, but the enzyme responsible for their biosynthesis remains unclear. UDP-galactose anthocyanidin 3- O -galactosyltransferase (UA3GalT) is presumed to catalyze the galactosylation of anthocyanidin. Therefore, we assayed the UA3GalT activity in five tea samples with varying degrees of purple color and found that its activity was strongly positively correlated (r = 0.929, p  < 0.05) with anthocyanin content. Phylogenetic analysis and sequence alignment suggested that CsUGT78A15 encoded a UA3GalT enzyme. Enzymatic assays indicated that r Cs UGT78A15 could catalyze the synthesis of cyanidin 3- O -galactoside and delphinidin 3- O -galactoside using UDP-galactose as a sugar donor, and it showed higher catalytic efficiency towards delphinidin than cyanidin. These results indicate that Cs UGT78A15 acts as a UA3GalT in vitro . Subcellular localization showed that Cs UGT78A15 was located in the endoplasmic reticulum (ER) and nucleus, consistent with the location of anthocyanin synthesis. Transient overexpression of CsUGT78A15 in the fruit of mature ‘Granny Smith’ apples showed that the upregulation of CsUGT78A15 promoted cyanidin 3- O -galactoside accumulation in apple skins. These results suggested that Cs UGT78A15 could catalyze galactosylation of anthocyanidins in planta . Our findings provide insight into the biosynthesis of anthocyanins in tea plants .

CAS / MDL: 28053-08-9
研究领域: 植物学 · 植物生物化学 · 分子生物学 · 遗传学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2020 · IF 4.006

Assessment of the formation of A-type proanthocyanidin by model reaction to blueberry extract and epicatechin

Wei Li,Jian Zhang,Lianfu Zhang

Blueberries are lacking in A-type proanthocyanidins, which assist in the prevention of urinary tract infections. Additive reactions to anthocyanins and a flavanol monomer promoted the formation of A-type proanthocyanidins. The four major anthocyanins of blueberry extracts are malvidin 3- O -glucoside, cyanidin 3- O -glucoside, delphinidin 3- O -glucoside and petunidin 3- O -glucoside. The model reaction of their two deglycosylation products, cyanidin and delphinidin with epicatechin, was investigated with different pH levels and under different thermal treatment conditions. At a pH 2.0–4.0, a nucleophilic addition occurred between the epicatechins and the anthocyanidins under flavylium form. Among the products, two colorless dimer adducts, A-type cyanidin-epicatechin (PAC-A2) and A-type delphinidin-epicatechin were obtained under optimal conditions (pH 2.0, at 90 °C, for 80 min, anerobic) and proved to be linked through a bicyclic bond (C4–C8, C2– O –C7) as detected in the A-type proanthocyanidins. This indicates that blueberry extract, originally rich in B-type proanthocyanidins, can produce A-type proanthocyanidins after processing.

研究领域: 食品科学 · 植物化学
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Antioxidants · 2023 ·Vol. 12 ·期 2 ·468 · IF 7

Extraction, Identification and Antioxidant Activity of 3-Deoxyanthocyanidins from Sorghum bicolor L. Moench Cultivated in China

Yanbei Wu,Yali Wang,Zhengyan Liu,Jing Wang

3-deoxyanthocyanidins (3-DAs) are typical flavonoids found in sorghum bran, and they have received much attention in recent years owing to their bioactivities. To further enhance the resource utilization of sorghums cultivated in China, three brewing sorghum cultivars (Liaoza-48, Liaonuo-11, and Liaonian-3) commonly used in China were selected as raw materials for the construction of an extraction technology system for 3-DAs and the clarification of their structures and bioactivities. Based on single-factor experiments and response surface analysis, the optimized system for the extraction of 3-DAs from sorghum grains was as follows: a hydrochloric acid-methanol solution (1:100,v/v) was the extraction solvent, the solid-liquid ratio was 1:20 (g/mL), the extraction time was 130 min, and the temperature was 40 °C. This extraction system was simple and feasible. High performance liquid chromatography analysis suggested that the main monomeric compounds of the extracted 3-DAs were Apigeninidin (AE) and Luteolinidin (LE). Among the three selected sorghum grains, Liaoza-48 had the highest amount of AE (329.64 μg/g) and LE (97.18 μg/g). Antioxidant experiments indicated that the 3-DAs extracted from Liaoza-48 showed higher free-radical scavenging activities for DPPH, ABTS+, and hydroxyl radicals than those extracted from Liaonuo-11 and Liaonian-3. These results provide basic data and technical support for the high-value and comprehensive utilization of sorghums in China.Keywords:sorghum;3-deoxyanthocyanidins;solvent extraction;Apigeninidin;Luteolinidin;bioactivity

CAS / MDL: 1898-66-4 28752-68-3
研究领域: 农业化学 · 食品科学 · 植物化学
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ANALYTICAL LETTERS · 2016 · IF 1.088

Determination of Eriodictyol by a Modified Multi-Walled Carbon Nanotube Glassy Carbon Electrode

Wan-Ling Cai,Ling Liu,Xue-Qing Liao,Kai-Li Tao,Fang Feng,Gong-Jun Yang

A modified multi-walled carbon nanotube glassy carbon electrode was fabricated, and the electrochemical behavior of eriodictyol on the surface of the multi-walled carbon nanotubes was investigated in detail. The cyclic voltammetry of eriodictyol showed a significant enhancement of the anodic peak current and a negative shift of the anodic peak potential at the modified glassy carbon electrode compared to a bare glassy carbon electrode. These results indicated that the multi-walled carbon nanotubes catalyzed the oxidation of eriodictyol. A method for the electrochemical determination of eriodictyol was developed using differential pulse voltammetry. Under the optimized conditions, the calibration relationship between the anodic peak current and eriodictyol concentration was linear from 1.0 to 1.0 × 103 ng mL−1 with a detection limit of 0.33 ng mL−1. The device was validated for precision and accuracy and used to determine eriodictyol in peanut shells with satisfactory results.

CAS / MDL: 552-58-9
研究领域: 分析化学 · 材料科学 · 植物化学
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Cell Death & Disease · 2023 ·Vol. 14 ·期 4 ·1-10 · IF 9

Cryptochrome 2 acetylation attenuates its antiproliferative effect in breast cancer

Xia Kangkai,Li Shujing,Yang Yuxi,Shi Xiaoxia,Zhao Binggong,Lv Linlin,Xin Zhiqiang,Kang Jie,Ren Ping,Wu Huijian

Breast cancer is the most commonly diagnosed cancer, and its global impact is increasing. Its onset and progression are influenced by multiple cues, one of which is the disruption of the internal circadian clock. Cryptochrome 2 (Cry2) genetic dysregulation may lead to the development of some diseases and even tumors. In addition, post-translational modifications can alter the Cry2 function. Here, we aimed to elucidate the post-translational regulations of Cry2 and its role in breast cancer pathogenesis. We identified p300-drived acetylation as a novel Cry2 post-translational modification, which histone deacetylase 6 (HDAC6) could reverse. Furthermore, we found that Cry2 inhibits breast cancer proliferation, but its acetylation impairs this effect. Finally, bioinformatics analysis revealed that genes repressed by Cry2 in breast cancer were mainly enriched in the NF-κB pathway, and acetylation reversed this repression. Collectively, these results indicate a novel Cry2 regulation mechanism and provide a rationale for its role in breast tumorigenesis.

CAS / MDL: 1313-82-2
研究领域: 肿瘤学 · 分子生物学 · 癌症生物学
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Frontiers in Pharmacology · 2023 · IF 5.6

Cryptochrome 1 activation inhibits melanogenesis and melanosome transport through negative regulation of cAMP/PKA/CREB signaling pathway

Gao Rongyin,Zhang Ximei,Zou Kun,Meng Duo,Lv Jinpeng

Cutaneous pigmentation was recently shown to be an event regulated by clock proteins. Cryptochrome (CRY) is a key protein composing the feedback loop of circadian clock, however, the function of CRY in melanocytes remains unclear. Here, we found that KL001, a synthetic small molecule modulator of CRY1, inhibited melanin synthesis, as well as reduced melanocyte dendrite elongation and melanosome transport. In addition, the dominant role of CRY1 in KL001-induced anti-melanogenesis was revealed by small interfering RNA transfection. Cellular tyrosinase activity and expression level of melanogenic proteins, including tyrosinase, TRP-1, TRP-2, and transport proteins like Rab27a, Cdc42 and Myosin Va induced by α-MSH were remarkably reversed after KL001 treatment. Mechanistically, CRY1 activation inhibited melanogenesis through CREB-dependent downregulation of MITF and CREB phosphorylation was mediated by classical cAMP/PKA pathway. In addition, the other CRY1 activator, KL044 also suppressed cAMP/PKA/CREB pathway and inhibited melanogenesis. Finally, anti-melanogenic efficacy of KL001 was confirmed by determination of melanin contents in UVB-tanning model of brown guinea pigs, which indicated that targeting CRY1 activity, via topical application of small molecule activator, can be utilized therapeutically to manage human pigmentary disorders.

研究领域: 细胞生物学 · 分子生物学 · 药理学 · 皮肤科
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Chemical Composition Profiling and Biological Activities of Phenolic Compounds in Eleven Red Sorghums

Yanfang Li,Ming Li,Jiaping Liu,Wenhao Zheng,Yaqiong Zhang,Tongcheng Xu,Boyan Gao,Liangli Yu

The profiles of soluble and insoluble phenolic compounds in 11 commercial red sorghums (B11, B12, B13, B14, J124, J127, J138, J140, J142, J152, and J158) were investigated using ultraperformance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry (UPLC/Q-TOF-MS) analysis. A total of 48 phenolic compounds including 35 phenolic acids and their derivatives, 12 flavonoids, and 1 proanthocyanidin were identified, and 8 phenolic compounds were reported for the first time in sorghums. Four major 3-deoxyanthocyanidins were also quantified, with their soluble forms accounting for 99.75–99.87% of the total contents. Pearson’s correlation analyses indicated that 3-deoxyanthocyanidins significantly contributed to the antioxidant capacities of the red sorghums and that 5-methoxy-luteolinidin showed the strongest correlation. Besides, the soluble phenolic fraction of B13 dose-dependently inhibited the proliferation of Caco-2 cells and the secretion of IL-1β and NO in RAW264.7 macrophages, which might be attributed to its relatively high total phenolic (TPC), flavonoid (TFC), and proanthocyanidin content (TPAC) values and radical scavenging capacities.

CAS / MDL: 153-18-4
研究领域: 食品科学 · 营养学 · 药理学 · 分析化学
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Frontiers in Molecular Biosciences · 2022 · IF 6.113

Investigation of Tannins Transformation in Sanguisorbae Radix Over Carbonizing by Stir-Frying

Wei Gu,Hao Wang,Man Su,Yiwei Wang,Fei Xu,Qinglian Hu,Xuyi Cai,Jinyun Song,Huangjin Tong,Yuerong Qian,Hongyu Zhao,Jun Chen

Carbonizing by stir-frying (CSF) is the most common technology in botanical folk medicines to enhance the convergence, hemostasis, and antidiarrheal effects. Sanguisorbae Radix (SR), a well-known herbal medicine in China, has extensive therapeutic functions, while charred SR is known as an additional product obtained from SR after CSF. In this study, mass spectrometry was used to investigate the effect of charring on tannins transformation of SR. The findings showed that the content level of tannins in SR decreased significantly after carbonizing process, while their three categories, gallotannins, ellagitannins, and procyanidins, had downward trends in general. Moreover, CSF also induced the polyphenol in SR to release relevant monomers from its origins. Significant amount of hydrolyzable tannins were detected by mass spectrometry, including gallotannins and ellagitannins, suggesting that hydrolysis during CSF yielded gallic and ellagic acid and their derivatives, in addition to sugar moieties. Subsequently, gallic and ellagic acid can further polymerize to form sanguisorbic acid dilactone. The amount of proanthocyanidins, the oligomers of catechin, including procyanidin, procyanidin C2, procyanidin B3, and 3-O-galloylprocyanidin B3, decreased to form catechin and its derivatives, which may further degrade to protocatechualdehyde. Quantitative analysis illustrated that the amount of gallic, pyrogallic, and ellagic acid and methyl gallate, the essential effectors in SR, significantly increased after CSF, with increased ratios of 1.36, 4.28, 10.33, and 4.79, respectively. In contrast, the contents of cathechin and epigallocatechin dropped remarkably with increased ratios of 0.04 and 0.02. Tannins exhibit moderate absorption, while their relevant monomers have a higher bioavailability. Therefore, CSF is proved here to be an effective technique to the release of active monomers from the original polyphenol precursor. This study explored the mechanism by which tannins are transformed upon CSF of SR.

CAS / MDL: 970-74-1
研究领域: 药用植物学 · 分析化学 · 中药学
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PLANT PHYSIOLOGY AND BIOCHEMISTRY · 2023 · IF 6.5

Onion cryptochrome 1 (AcCRY1) regulates photomorphogenesis and photoperiod flowering in Arabidopsis and exploration of its functional mechanisms under blue light

Qingwei Jia,Yuqing Yin,Shuting Gai,Lu Tian,Zhihao Zhu,Lei Qin,Yong Wang

Cryptochromes (CRYs), as blue-light photoreceptors, play a crucial role in regulating flowering time and hypocotyl and cotyledon development. Their physiological functions have been extensively studied in various plant species. However, research on onions remains limited. In this study, we identified AcCRY1 and conducted preliminary investigations into its function. Our results demonstrate that AcCRY1 possesses a conserved domain typical of cryptochromes with high homology to those found in monocots. Furthermore, we examined the expression level of AcCRY1 in onion. The green tissues is significantly higher compared to non-green tissues, and it exhibits a significant response to blue-light induction. AcCRY1 demonstrates cytoplasmic localization under blue-light conditions, while it localizes in the nucleus during darkness, indicating a strong dependence on blue-light for its subcellular distribution. In comparison to cry1 , overexpression of AcCRY1 leads to a significant shorten in seedling hypocotyl length, notable expansion of cotyledons, and acceleration of flowering time. The yeast two-hybrid experiment demonstrated the in vitro interaction between AcCRY1, AcCOP1, and AcSPA1. Additionally, BIFC analysis confirmed their interaction in Onion epidermis. Notably, under blue-light conditions, a significantly enhanced binding activity was observed compared to dark conditions. These findings establish a functional foundation for the regulatory role of AcCRY1 in important physiological processes of onion and provide initial insights into the underlying molecular mechanisms.

研究领域: 植物生物学 · 分子生物学 · 遗传学
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JOURNAL OF MOLECULAR STRUCTURE · 2021 · IF 3.196

Two novel mono-hydroxyl pyranoanthocyanidins bearing dimethylamino substituent(s) for dye-sensitized solar cell

Xiaolong Shi,Yuanzuo Li,Lihai Wang

Two novel analogues (AF3-1 and AF3-2) of natural pigments that were originally found in wine product, pyranoanthocyanidins, were designed based on pyrano-4′-dimethylamino-10-phenyl-flavylium (AF3) by respectively introducing another electron donor(s), dimethylamino and two methoxyl groups, to the phenyl moiety. They were synthesized and then successfully applied as sensitizers in DSSC to study effect of the additional donor(s) on the DSSC performance for such pyranoanthocyanidin. The introduced second dimethylamino substituent of AF3-1 slightly red shifts the absorption spectrum. Both title dyes show relatively strong ability to shield the photoanode surface from electrolyte and to restrain the electron recapture process. Yet it is difficulty for them to adsorb on the semiconductor surface effectively and to avoid undesirable dye aggregation. DSSCs based on the designed pyranoanthocyanidin turn out to have much higher V oc but decreased J sc compared to AF3. PCE of DSSC assembled with the better of the two pyranoanthocyanidins, AF3-1, is 1.79%, on the same level as that of the reference sensitizer.

研究领域: 化学 · 材料科学 · 太阳能
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2024 · IF 7.7

Structural and mechanistic insights into the anti-tyrosinase, anti-melanogenesis, and anti-browning effect of proanthocyanidins from seed coats of Acer truncatum Bunge

Jiangping Huang,Meiting Li,Chengyun Han,Zhongwei Zhang,Xiang Liu,Zhixuan Ying,Peipei Yin,Lingguang Yang

Acer truncatum is a multifunctional tree species with broad applications in ornamental, healthy drink, and seed oil. In the present study, proanthocyanidins were isolated from the seed coats of A. truncatum , which were largely discarded as industrial wastes in seed oil production. Meanwhile, structural features, effects and mechanisms of anti-tyrosinase, anti-melanogenesis, and anti-browning of A. truncatum seed coat proanthocyanidins (ASPs) were systematically investigated. The joint application of FT-IR, MALDI-TOF-MS, hiolysis-coupled reverse-phase LC-ESI-MS, together with normal-phase LC confirmed that ASPs were predominately constituted by procyanidins with a mean polymerization degree of 12.09. Furthermore, ASPs powerfully inhibited both monophenolase and diphenolase activities of tyrosinase, and the inhibition of diphenolase was proved to be reversible and competitive−uncompetitive mixed type. Analyses of fluorescence quenching, UV spectra, and copper-ion chelation indicated that ASPs could inhibit tyrosinase in varied stages, and molecular docking and dynamic simulation further revealed the interaction mode between ASPs and tyrosinase. Cell assays further suggested that ASPs exhibited a strong inhibition against intracellular tyrosinase activity and melanin production through suppressing the expression of tyrosinase and microphthalmia transcription factor (MITF) at transcription level and caused apoptosis in B16F10 cells at higher concentrations. Antioxidant and anti-browning studies demonstrated that ASPs possessed high capacities of antioxidant, and potently suppress the browning of fresh-cut potatoes. Therefore, this study confirmed that seed coats of Acer truncatum is a potential natural source of tyrosinase, melanogenesis, and browning inhibitor, which provided a theoretical basis for the utilization of ASPs in the cosmetics, pharmaceutical, and food industries.

研究领域: 药理学 · 生物化学 · 化妆品科学 · 食品科学 · 植物科学
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