Recovery of Low-molecular Weight Galloyltannins from Agricultural Residue of Juglans sigillata Dode Seed Husks and their Tyrosinase Inhibitory Effect

Si, Chuanling; Wu, Lei; Shen, Ting; Huang, Xiaofeng; Du, Zhen-Guo; Ren, Xiancheng; Luo, Xue‐Gang; Hu, Weicheng

doi:10.15376/biores.9.2.2226-2236

Cited by 10 publications

(5 citation statements)

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“…Based on the characteristics mentioned above, referencing the previous reports [ 16 , 25 ], the valonea tannin inhibition reaction was classified as a reversible type. As for tannic acid or gallic acid, their tyrosinase concentration-reaction rate plots also showed significant characteristics of the reversible type as well ( Figure 4 B,C), in agreement with the results obtained by previous research [ 26 ].…”

Section: Resultssupporting

confidence: 91%

Valonea Tannin: Tyrosinase Inhibition Activity, Structural Elucidation and Insights into the Inhibition Mechanism

Liu

et al. 2021

Molecules

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Valonea tannin is a natural product readily extracted from acorn shells that has been suggested to have potential skin whitening properties. This study investigated the tyrosinase inhibition activity of extracted valonea tannin and the associated structure–function activity. Nuclear magnetic resonance spectroscopy and molecular weight analysis with gel permeation chromatography revealed that valonea tannin could be characterized as a hydrolysable tannin with galloyl, hexahydroxydiphenoyl and open formed-glucose moieties and an average molecular weight of 3042 ± 15 Da. Tyrosinase inhibition assays demonstrated that valonea tannin was 334 times more effective than gallic acid and 3.4 times more effective than tannic acid, which may relate to the larger molecular size. Kinetic studies of the inhibition reactions indicated that valonea tannin provided tyrosinase inhibition through mixed competitive–uncompetitive way. Stern–Volmer fitted fluorescence quenching analysis, isothermal titration calorimetry analysis and in silico molecule docking showed valonea tannin non-selectively bound to the surface of tyrosinase via hydrogen bonds and hydrophobic interactions. Inductively coupled plasma-optical emission spectroscopy and free radical scavenging assays indicated the valonea tannin had copper ion chelating and antioxidant ability, which may also contribute to inhibition activity. These results demonstrated the structure–function activity of valonea tannin as a highly effective natural tyrosinase inhibitor that may have commercial application in dermatological medicines or cosmetic products.

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Section: Resultssupporting

confidence: 91%

Valonea Tannin: Tyrosinase Inhibition Activity, Structural Elucidation and Insights into the Inhibition Mechanism

Liu

et al. 2021

Molecules

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“…Only four types of galloyl glucosides were detected in the leaves, [8] whereas gallic acid (GA), ellagic acid, tannic acids, (+)-catechin, (−)-epicatechin, (+)-catechin(4 → 8″)-(+)-catechin, (+)-catechin(4α 65 → 658)-(+)-catechin, five types of galloyl glucosides, and 9 α-tetralone derivatives were found in green husks. [9][10][11][12] GA, ellagic acid, pedunculagin, 2,3-O-4,4′,5,5′,6,6′-hexahydroxydiphenoyl-(α/β)-glucose, and six types of galloyl glucosides were found in stem bark. [13] Walnut green husks are primary by-products of walnut production and are an important source of natural phenolic compounds; however, because of the lack of research attention, the use of phenolic compounds constituent in green husks of J. sigillata is limited.…”

Section: Introductionmentioning

confidence: 99%

Seasonal variations of phenolic profiles and antioxidant activity of walnut (Juglans sigillata Dode) green husks

Shi

Wen-e

Xue

et al. 2017

International Journal of Food Properties

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The phenolics content and antioxidant activity of walnut (Juglans sigillata Dode) green husks were analysed during different stages of development. Contents of total phenolics and total flavonoids decreased from April 25th to June 7th, then increased during June and July, and decreased again at the beginning of August. Thirteen types of phenolic compounds were identified using HPLC of which juglone had the highest content. Because of seasonal variations, the trends of different phenolic compounds were different. Contents of both total phenolics and total flavonoids were strongly correlated with antioxidant activity; however, compared with totals, less significant correlations were observed between individual phenolic compounds and antioxidant activities.

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“…It is a fast-growing deciduous tree indigenous to the mountain regions of Tibet, Sichuan, Yunnan, and Guizhou provinces in southwest China. 17 The seeds of J. sigillata are highly valued for their dietary nutrition, and its seed husks have long been used as folk medicine for the treatment of esophageal, gastric, cardiac, and lung cancers. 18 The husks of J. sigillata fruits, long been treated as an agricultural and food industry residue, are therefore a valuable resource for extracting potential value-added medicines, healthcare agents, and cosmetics.…”

Section: Introductionmentioning

confidence: 99%

Apigenin-7-O-β-d-glucuronide inhibits LPS-induced inflammation through the inactivation of AP-1 and MAPK signaling pathways in RAW 264.7 macrophages and protects mice against endotoxin shock

Wang

et al. 2016

Food Funct.

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Apigenin-7-O-β-D-glucuronide (AG), an active flavonoid derivative isolated from the agricultural residue of Juglans sigillata fruit husks, possesses multiple pharmacological activities, including anti-oxidant, anti-complement, and aldose reductase inhibitory activities. To date, no report has identified the anti-inflammatory mechanisms of AG. This study was therefore designed to characterize the molecular mechanisms of AG on lipopolysaccharide (LPS)-induced inflammatory cytokines in RAW 264.7 cells and on endotoxin-induced shock in mice. AG suppressed the release of nitric oxide (NO), prostaglandin E2 (PGE2), and tumour necrosis factor-α (TNF-α) in LPS-stimulated RAW 264.7 macrophages in a dose-dependent manner without affecting cell viability. Additionally, AG suppressed LPS-induced mRNA expression of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and TNF-α. AG treatment decreased the translocation of c-Jun into the nucleus, and decreased activator protein-1 (AP-1)-mediated luciferase activity through the inhibition of both p38 mitogen-activated protein kinase (MAPK) and extracellular signal-regulated kinase (ERK) phosphorylation. Consistent with the in vitro observations, AG protected mice from LPS-induced endotoxin shock by inhibiting proinflammatory cytokine production. Taken together, these results suggest that AG may be used as a source of anti-inflammatory agents as well as a dietary complement for health promotion.

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Recovery of Low-molecular Weight Galloyltannins from Agricultural Residue of Juglans sigillata Dode Seed Husks and their Tyrosinase Inhibitory Effect

Cited by 10 publications

References 0 publications

Valonea Tannin: Tyrosinase Inhibition Activity, Structural Elucidation and Insights into the Inhibition Mechanism

Valonea Tannin: Tyrosinase Inhibition Activity, Structural Elucidation and Insights into the Inhibition Mechanism

Seasonal variations of phenolic profiles and antioxidant activity of walnut (Juglans sigillata Dode) green husks

Apigenin-7-O-β-d-glucuronide inhibits LPS-induced inflammation through the inactivation of AP-1 and MAPK signaling pathways in RAW 264.7 macrophages and protects mice against endotoxin shock

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