Recent Advances in Pharmaceutical Cocrystals: A Focused Review of Flavonoid Cocrystals

Xu, Jia; Shi, Qin; Wang, Yanan; Wang, Yong; Xin, Junbo; Cheng, Jun; Li, Fang

doi:10.3390/molecules28020613

Cited by 15 publications

(7 citation statements)

References 130 publications

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“…Solubility equilibrium is a type of dynamic equilibrium that exists when a chemical drug in the solid state is in chemical equilibrium with a solution of that compound . The cocrystal technique is used to increase the solubility of insoluble drugs and is one of the effective methods to increase their aqueous solubility. , To check whether the cocrystal technique improved the solubility of naringenin, we tested the solubility of NAR, NOR, and cocrystal 3 in pure water, phosphate buffer (pH = 6.8), and dilute hydrochloric acid solution (pH = 1.2) separately, and the results are shown in Figure . The experimental results showed that in pure water, the solubility in descending order was cocrystal 3 > NOR > NAR.…”

Section: Resultsmentioning

confidence: 99%

Cocrystal of Naringenin and Norfloxacin: Crystal Transformation, Solubility, and Antibacterial and Anticancer Activities

Zeng,

Zheng,

Qiu

et al. 2024

Crystal Growth & Design

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Drug cocrystals can modulate the physical and chemical properties of drugs, even complement each other’s strengths, and have a synergistic enhancement effect. Here, we reported a drug cocrystal prepared by norfloxacin (NOR) and naringenin (NAR), comprising an antibacterial drug and an antitumor active pharmaceutical ingredient. The cocrystal hydrate obtained by crystal transformation methods enhanced the antibacterial activity of NOR against one Gram-positive bacterium (Staphylococcus aureus), three Gram-negative bacteria (Escherichia coli, Dysentery bacillus, Pseudomonas aeruginosa), and one fungus (Candida albicans), improved the solubility of NAR, reduced the hygroscopicity of NOR, and enhanced the anticancer activity of NAR against human breast cancer cells MDA-MB-231. This combination has potential therapeutic synergy in clinical terms.

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Section: Resultsmentioning

confidence: 99%

Cocrystal of Naringenin and Norfloxacin: Crystal Transformation, Solubility, and Antibacterial and Anticancer Activities

Zeng,

Zheng,

Qiu

et al. 2024

Crystal Growth & Design

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“…However, it was very hard to identify the structure simply compared to the physical and spectroscopic data previously reported, since several monomethoxyflavones are possible. Attempted approaches to produce a single crystal directly the product or its cocrystals with coformers [ 32 , 33 ] such as isoniazid, isonicotinamide, and caffeine were fruitless. The problem was solved, to our delight, as its tetraacetate was suitable for X-ray analysis.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies toward 5,6,7,3′,4′-Monomethoxytetrahydroxyflavones: Synthesis of Pedalitin

Kamma,

Cho,

Won

et al. 2024

Molecules

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During the synthetic studies toward 5,6,7,3′,4′-monomethoxytetrahydroxyflavones, a concise pedalitin synthesis procedure was achieved. As previously reported, 6-hydroxy-2,3,4-trimethoxyacetophenone was prepared by Friedel–Crafts acylation of 1,4-dihydroxy-2,6-dimethoxybenzene with boron trifluoride diethyl etherate in acetic acid. When aldol condensation of 6-hydroxy-2,3,4-trimethoxyacetophenone 2b with vanillin was performed in basic conditions, it produced 2′-hydroxychalcone 3b, and, surprisingly, along with 3-hydroxyflavone 4 in a considerable amount. We propose that this oxidative cyclization is presumably due to the contribution of a quinone methide, likely to be subjected to aerobic oxidation. The chalcone was then subjected to oxidative cyclization with iodine in dimethyl sulfoxide to afford flavone 5 in good yield. To our delight, serial demethylation of the three methoxy groups at the 5-, 6-, and 3′-positions of 5 proceeded smoothly to produce pedalitin 1, under hydrogen bromide solution (30% in acetic acid). The crystal structures of 3-hydroxyflavone 4 and pedalitin tetraacetate 6 were unambiguously determined by X-ray crystallography.

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“…Flavonoids, including flavonols, flavonoids, chalcones, and proanthocyanidins, are natural active substances with significant health benefits and potential applications in healthcare and medicine [53,54]. In this study, we conducted a metabolomics analysis on the WR and RR of P. kingianum Coll.et Hemsl., and 200 flavonoid compounds were identified from these two organs.…”

Section: Discussionmentioning

confidence: 99%

Combined Metabolomics and Transcriptomics Analysis of the Distribution of Flavonoids in the Fibrous Root and Taproot of Polygonatum kingianum Coll.et Hemsl

Mo,

Wang,

et al. 2024

Genes

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Polygonati rhizoma, known for its distinct yellow rhizomes, is a common therapeutic and culinary plant in Far East Asia. The hue of medicinal plants is closely tied to the flavonoid biosynthesis and content levels. In this research, the fibrous root and taproot of Polygonatum kingianum Coll.et Hemsl. were studied to explore the secondary metabolite expression and flavonoid biosynthesis mechanisms using transcriptomics and metabolomics. Metabolic analysis identified that the differentially accumulated metabolites (DAMs) in the fibrous root and taproot were predominantly flavonoids, steroids, alkaloids, and phenolic acids. Overall, 200 flavonoids were identified in P. kingianum Coll.et Hemsl., with 170 exhibiting variances between the fibrous root and taproot. The transcriptome analysis revealed that a total of 289 unigenes encoding 32 enzymes were annotated into four flavonoid biosynthesis pathways, which include phenylpropanoid biosynthesis pathway, flavonoid biosynthesis pathway, isoflavonoid biosynthesis pathway, and flavone and flavonol biosynthesis pathway. The integration of transcriptomic and metabolomic data elucidated that the 76 differentially expressed genes (DEGs) encoding 13 enzyme genes (HCT, CCOMT, C4H, C3′H, CHI, PGT1, FLS, F3′H, CHS, ANR, DFR, F3′5′H, and LAR) and 15 DAMs preferred to be regulated in the flavonoid biosynthesis pathway. The expression of 10 DEGs was validated by qRT-PCR, agreeing with the same results by RNA-Seq. These findings shed light into the biosynthesis of secondary metabolites in P. kingianum Coll.et Hemsl., offering valuable information for the sustainable utilization and enhancement of this plant species.

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Recent Advances in Pharmaceutical Cocrystals: A Focused Review of Flavonoid Cocrystals

Cited by 15 publications

References 130 publications

Cocrystal of Naringenin and Norfloxacin: Crystal Transformation, Solubility, and Antibacterial and Anticancer Activities

Cocrystal of Naringenin and Norfloxacin: Crystal Transformation, Solubility, and Antibacterial and Anticancer Activities

Synthetic Studies toward 5,6,7,3′,4′-Monomethoxytetrahydroxyflavones: Synthesis of Pedalitin

Combined Metabolomics and Transcriptomics Analysis of the Distribution of Flavonoids in the Fibrous Root and Taproot of Polygonatum kingianum Coll.et Hemsl

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