Studies on crystal structures, optical, dyeing and biological properties of protoberberine alkaloids and their supramolecular salts

Du, Haijuan; Hao, Keqian; Wang, Qi; Huang, Xin; Wu, Jie; Liu, Hongyun; Huang, Chunyue; Xu, Lang; Li, Yin; Lin, Jie

doi:10.1016/j.bioorg.2022.106256

Cited by 4 publications

(3 citation statements)

References 45 publications

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“…The extraction of PLTCl and synthesis of PLT-SA and PLT-SSA were performed following the reported papers. , …”

Section: Methodsmentioning

confidence: 99%

“…36−38 Similarly, the supramolecular salt of PLT-sulfosalicylic acid (PLT-SSA) was designed and synthesized by replacing the Cl − of PLTCl, and the physicochemical and biological properties were obviously improved. 39 Given that sulfosalicylic acid is a strong organic acid with rich functional groups such as hydroxyl, carboxylic acid, and sulfonic acid, it is likely to form new crystal supramolecular structures. 40−44 On the whole, the introduction of some aromatic carboxylic acids as guest ions to generate new crystalline supramolecular salts or cocrystals was a new strategy to design smart fluorescent materials with improved physicochemical properties by replacing anions.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Natural alkaloids, as secondary metabolites in plants, are widely found in nature with novel molecular structures and fluorescent properties. − The main sources of yellow alkaloids are plants, and some of them exhibit coloring properties and are used mainly as traditional Chinese medicines, e.g., derivatives of protoberberine. Alkaloids are also recognized as the largest group of nitrogen-containing secondary metabolites. − Palmatine (PLT) is a natural isoquinoline alkaloid as well as a close analogue of berberine (BB), sharing many performances and activities of BB. , Recently, PLT was widely used as a potential fluorescent dye in the application of bioimaging , as well as in sensing and developing of functional dyes. − PLT as a class of protoberberines is bright yellow in color that has been utilized for centuries in Chinese and other traditional medicines and also as dyes for textiles and paper. , PLT chloride (PLTCl) is the most commonly used salt form of PLT in commercial tablets, exhibiting a series of biochemical and pharmacological effects and coloring properties. , Some papers have suggested a new approach to design and produce single crystals of PLT-organic acid salt by replacing anions, offering insights into improving the physicochemical properties of active pharmaceutical ingredients. − Similarly, the supramolecular salt of PLT-sulfosalicylic acid (PLT-SSA) was designed and synthesized by replacing the Cl – of PLTCl, and the physicochemical and biological properties were obviously improved . Given that sulfosalicylic acid is a strong organic acid with rich functional groups such as hydroxyl, carboxylic acid, and sulfonic acid, it is likely to form new crystal supramolecular structures. − …”

Section: Introductionmentioning

confidence: 99%

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Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Du,

Huang,

Wang

et al. 2024

Crystal Growth & Design

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Palmatine as a natural isoquinoline alkaloid possesses biological activity, low toxicity, biodegradability, fluorescence, and antibacterial properties; however, the low fluorescent intensity and poor stability hindered its practical applications, especially in bioimaging, detection of probes, and functional dyes as the fluorophore. Serial aromatic carboxylic acids as guest ions were introduced by replacing anions of the host Palmatine to fabricate new crystalline Palmatine-based supramolecular salts or cocrystals. The structures and fluorescent properties of the prepared supramolecules were examined by single-crystal X-ray diffraction, thermogravimetry, ultraviolet spectrophotometry, fluorescence spectrometry, and infrared spectrometry. It was found that the fluorescence performance could be tuned by introducing guest molecules based on salicylic acid with different push−pull electronic groups to affect the π−π conjugation system. The introduction of −NO 2 in salicylic acid can result in a decrease in fluorescence on account of withdrawing electrons from the benzene ring, thereby reducing the probability of electron transition. Surprisingly, the fluorescence intensity of Palmatine-aminosalicylic acid (−NH 2 ) exhibited a 10-fold increase due to the decline of the energy gap between the highest occupied molecular orbital and the lowest unoccupied molecular orbital. These findings provided a theoretical basis for further regulating the fluorescence performance of Palmatine and other natural dyes through the introduction of guest molecules to form the supramolecular systems.

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“…The extraction of PLTCl and synthesis of PLT-SA and PLT-SSA were performed following the reported papers. , …”

Section: Methodsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Du,

Huang,

Wang

et al. 2024

Crystal Growth & Design

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Assembly of two palmatine pharmaceutical salts: Changing the motifs and affecting the physicochemical properties by adjusting the position of –COOH on salt formers

Liu

Zhang

et al. 2023

Journal of Drug Delivery Science and Technology

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Study on Dyeing Properties and Color Characteristics of Wool Fabrics Dyed with Geranium caespitosum L. Extract—A New Natural Yellow Dye

Zhao

Yan

et al. 2023

Coatings

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Natural dyes play an important role in sustainable dyeing processes. However, natural yellow dyes with good performance are rare. Traditional natural yellow dyes have issues, such as a narrow color range and poor light fastness. In this paper, a new natural yellow dye was extracted from a low-cost herb Geranium caespitosum L. (G. caespitosum). In addition, the dye composition was analyzed using UV-visible spectroscopy. The dyeing process of G. caespitosum dye on wool fabrics was optimized using single-factor experiments. Standard fastness tests were conducted to evaluate the sunlight, washing, and rubbing fastness of the dyed fabrics. The color characteristics and color gamut range of the dyed fabrics were evaluated. The obtained colors were compared and assessed with Pantone Matching Systems and Chinese traditional colors. The results showed that phenolic acids and flavonoids were present in the G. caespitosum dye solution as yellow dye compounds. The best dyeing process for wool fabrics was meta-mordanting. The dyed fabrics were bright yellow at 60 °C and golden yellow at 90 °C. All the obtained colors were in the yellow-red range. According to the ISO color fastness standards, wool fabrics dyed with G. caespitosum dye had good color fastness ratings, particularly sunlight fastness. Therefore, G. caespitosum dye is a promising natural yellow dye that can be used for wool fabric dyeing. It has advantages over other known natural yellow dyes and has certain application value.

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Studies on crystal structures, optical, dyeing and biological properties of protoberberine alkaloids and their supramolecular salts

Cited by 4 publications

References 45 publications

Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Significant Effect of Guest Ions on the Fluorescence Behaviors of Palmatine-Based Supramolecular Systems

Assembly of two palmatine pharmaceutical salts: Changing the motifs and affecting the physicochemical properties by adjusting the position of –COOH on salt formers

Study on Dyeing Properties and Color Characteristics of Wool Fabrics Dyed with Geranium caespitosum L. Extract—A New Natural Yellow Dye

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