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香叶木素
FOOD CHEMISTRY · 2016 · IF 4.052

The structure-antifungal activity relationship of 5,7-dihydroxyflavonoids against Penicillium italicum

Shuzhen Yang,Jie Zhou,Dongmei Li,Chunyu Shang,Litao Peng,Siyi Pan

To evaluate the structure-activity relationship of 5,7-dihydroxyflavonoids against P. italicum , we tested the antifungal activity of 23 selected 5,7-dihydroxyflavonoids against spore germination of P. italicum , and the effects of hydroxyl group, hydrogenation, methylation and glycosylation on the antifungal activity are explored. C-4′-OH and C-3-OH are active groups for the 5,7-dihydroxyflavonoids against P. italicum. We find that hydrogenation of the C2/C3 bond decreases the antifungal activity of 5,7-dihydroxyflavonoids. Antifungal activity of 5,7-dihydroxyflavonoids against P. italicum was affected by the conjugation site of glycosylation and the class of sugar moiety. The correlation between antifungal activity and the inhibition of respiration of 5,7-dihydroxyflavonoids was further evaluated. We find no significant relationship among the IC50 of 5,7-dihydroxyflavonoids on spore germination and on respiration. Some 5,7-dihydroxyflavonoids even enhance the respiration of P. italicum . This indicate respiration is not the only target for 5,7-dihydroxyflavonoids against P. italicum .

✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD RESEARCH INTERNATIONAL · 2025 · IF 8

Influence of hydroxyl substitution on the inhibition of flavonoids in advanced glycation end-products formation in glucose-lysine-arginine Maillard reaction models

Li-Feng Li,Meng-Di Wang,Chen-Yang Zhang,Meng-Yao Jin,Hua-Lei Chen,Huan Luo,Tian-Yu Hou,Zhi-Jun Zhang,He Li

Advanced glycation end products (AGEs) generated from the Maillard reaction (MR) during food processing in the human physiological environment, have been proven to be significantly associated with various chronic metabolic diseases. In this study, 18 flavonoids were investigated to study their effects on AGEs formation during MR within a glucose-lysine-arginine model system. Five AGEs— N ε -carboxymethyl-lysine (CML), N ε -carboxyethyl-lysine (CEL), pyrraline, pentosidine, and argpyrimidine—were determined by high-performance liquid chromatography-mass spectrometry, with inhibitory rates ranging between 0 % and 71.35 %. Isorhamnetin and naringenin exhibited the strongest inhibitory effect on the formation of CML and CEL, respectively, whereas myricetin exhibited the strongest inhibitory effect on pyrraline, pentosidine, and argpyrimidine formation. In addition, each flavonoid was reacted with glyoxal (GO) and methylglyoxal (MGO) to investigate their trapping activities and adducts. The results showed that the 18 flavonoids could effectively clear GO and MGO, with clearance rates of 1.03 %–71.42 % and 0.93 %–69.37 % for GO and MGO, respectively. Six flavonoids—chrysin, naringenin, apigenin, luteolin, diosmetin, and kaempferol—could form adduct products with mono-/di-MGO, with flavonoid to mono-/di-MGO adduct ratios of approximately 6:1, 2:1, 8:1, 23:1, 10:1, and 3:1, respectively. The number and site of phenolic hydroxyl groups, as well as methoxy substitution on the B-ring in flavonoids, had little effect, but phenolic hydroxyl groups at the C-3 position in the C-ring impeded adduct formation. The flavonoids lowered the degradation of glucose itself, and decreased ammonia-induced degradation and Amadori rearrangement product oxidation due to their antioxidant activities, and they trapped the reactive 1,2-di‑carbonyl species via nucleophilic addition reaction to form AGEs.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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CARBOHYDRATE POLYMERS · 2025 · IF 12.5

Premna microphylla Turcz pectin-modified diosmetin nanoparticles: A galectin-3 targeting strategy for precise colitis intervention

Yuanyuan Chen,Qian Zhou,Yue Zhou,Jinlan Huang,Renjie Niu,Jian Ming,Mingfu Wang

Oral delivery of natural antioxidants represents a promising therapeutic strategy for ulcerative colitis (UC), yet their therapeutic efficacy is hindered by instability and poor accumulation at inflamed sites. To address this, we developed Galectin-3 (Gal-3)-targeted nanoparticles (ZDP-NPs) by encapsulating diosmetin within zein complexes modified with a galactose- and rhamnogalacturonan-I (RG-I)-rich pectin (PMTP, Mw: 228.8 kDa, DM: 34.21 %, RG-I content: 43 %) extracted from Premna microphylla Turcz leaves. Surface plasmon resonance (SPR) analysis confirmed a strong binding affinity between PMTP and Gal-3 (KD = 2.83 μM). ZDP-NPs exhibited uniform spherical morphology (~170 nm), high drug loading (87.9 %) and colloidal stability. Under simulated gastrointestinal conditions, ZDP-NPs showed reduced Dio release (45.6 %) compared to PMTP-free nanoparticles (ZD-NPs, 75.6 %). In vitro studies showed that PMTP surface modification significantly enhanced nanoparticle uptake by LPS-induced macrophages via Gal-3-mediated endocytosis. In vivo colitis experiment of mice revealed that ZDP-NPs selectively accumulated in inflamed colons via Gal-3 targeting, prolonged retention, and significantly alleviated colonic damage by reducing oxidative stress, suppressing pro-inflammatory cytokines, and restoring epithelial barrier integrity. Biocompatibility assays confirmed minimal toxicity of ZDP-NPs. This study presented a food-derived pectin-based nanoplatform for precise colitis intervention through Gal-3 targeting, offering a multifaceted strategy to break the inflammation-oxidative stress cycle.

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