Syntheses and high selective cytotoxicity of dehydroabietylamine C-ring nitration derivatives

Gu, Zhenzhen; Lu, Weiying; Xue, Huayu; Zhang, Jingjing; Yang, Shilong; Xu, Li

doi:10.1016/j.fitote.2022.105232

Cited by 5 publications

(5 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Absorbance was measured at 595 nm in a microplate photometer. Cell viability values were determined (at least three times) according to the following formulae: cell viability (%) = the absorbance of the experimental group/the absorbance of the blank control group × 100% [ 29 , 30 ].…”

Section: Methodsmentioning

confidence: 99%

Research on Anthocyanins from Rubus “Shuofeng” as Potential Antiproliferative and Apoptosis-Inducing Agents

Zhao

Wang

et al. 2023

Foods

View full text Add to dashboard Cite

Blackberries have high nutritional value and strong biological activities, such as antiproliferative activity. Anthocyanins are important functional components in blackberries. We collected 25 kinds (lines) of blackberries from our nursery to investigate antiproliferative agents in natural foods. Among them, the Shuofeng variety had the highest anthocyanin content, with 2.54 mg/g of fresh fruit, which increased to 357.75 mg/g of dried powder through ultrasound-assisted solvent extraction and macroporous resin adsorption. Additional experiments showed that Shuofeng’s anthocyanin content had high anti-HepG2 activity in vitro and in vivo, as well as activity against Hela (68.62 μg/mL), HepG2 (55.85 μg/mL), MCF-7 (181.21 μg/mL), and A549 cells (82.01 μg/mL), as determined by MTT assay. It also had no apparent toxic effects. The combination of DDP and DOX significantly enhanced the antiproliferative activity of the four cell lines. The IC50 value of Shuofeng’s anthocyanin content combined with DOX in HepG2 cells was the lowest at only 0.08 μg/mL, indicating that the combination of drugs had additive and synergistic effects. Shuofeng’s anthocyanin content might intercalate into DNA and alter or destroy DNA, causing apoptosis and inhibiting cell proliferation. Our results show that blackberry anthocyanins can inhibit the proliferation of cancer cells and their possible mechanisms. However, we must study the deeper mechanism and explore its targeting effects in the future.

show abstract

Section: Methodsmentioning

confidence: 99%

Research on Anthocyanins from Rubus “Shuofeng” as Potential Antiproliferative and Apoptosis-Inducing Agents

Zhao

Wang

et al. 2023

Foods

View full text Add to dashboard Cite

show abstract

“…The cytotoxicity for the nonmalignant cell line (HUVEC cells) was also investigated to characterize the selectivity expressed according to selectivity index (SI) (SI = (IC 50 for nonmalignant cell line HUVEC)/(IC 50 for human tumor cell line)) [ 35 ], illustrated in Figure 2 . SI was an important aspect for prospective pharmacological applications.…”

Section: Resultsmentioning

confidence: 99%

“…Blueberry anthocyanins have been found to play a role in mitochondrial-mediated apoptosis [ 34 ]. Apoptosis plays a core role in cancer because its induction in cancer cells is the key to successful treatment [ 35 ]. Apoptosis is controlled by genes of orderly cell death.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

The Extraction and High Antiproliferative Effect of Anthocyanin from Gardenblue Blueberry

Zhao

Wang

et al. 2023

Molecules

View full text Add to dashboard Cite

Blueberries are rich in flavonoids, anthocyanins, phenolic acids, and other bioactive substances. Anthocyanins are important functional components in blueberries. We collected 65 varieties of blueberries to investigate their nutritional and functional values. Among them, Gardenblue had the highest anthocyanin content, with 2.59 mg/g in fresh fruit. After ultrasound-assisted solvent extraction and macroporous resin absorption, the content was increased to 459.81 mg/g in the dried powder. Biological experiments showed that Gardenblue anthocyanins (L1) had antiproliferative effect on cervical cancer cells (Hela, 51.98 μg/mL), liver cancer cells (HepG2, 23.57 μg/mL), breast cancer cells (MCF-7, 113.39 μg/mL), and lung cancer cells (A549, 76.10 μg/mL), and no apparent toxic effects were indicated by methyl thiazolyl tetrazolium (MTT) assay, especially against HepG2 cells both in vitro and in vivo. After combining it with DDP (cisplatin) and DOX (doxorubicin), the antiproliferative effects were enhanced, especially when combined with DOX against HepG2 cells; the IC50 value was 0.02 μg/mL. This was further evidence that L1 could inhibit cell proliferation by inducing apoptosis. The detailed mechanism might be L1 interacting with DNA in an intercalation mode that changes or destroys DNA, causing apoptosis and inhibiting cell proliferation. The findings of this study suggest that L1 extract can be used as a functional agent against hepatoma carcinoma cells.

show abstract

“…Its main component is resin acid with a tricyclic diterpenoid. , Dehydroabietylamine is a synthetically modified product of rosin. Dehydroabietylamine ( 1 ) presents a wide range of biological activities, including antibacterial, antifungal, antiherpetic, antidengue, and anticancer activities. − Modification of dehydroabietylamine mainly targets its chemically active sites, including the C-18 amino group in the A ring, − the C-7 benzylic position in the B ring, − and the aromatic ring (C ring). − …”

mentioning

confidence: 99%

Discovery of Dehydroabietylamine Derivatives as Antibacterial and Antifungal Agents

Zhang,

Wan,

Zhang

2024

J. Nat. Prod.

View full text Add to dashboard Cite

A diverse array of biologically active derivatives was derived by modifying the chemically active sites of dehydroabietylamine. Herein, we describe the synthesis of a new series of C-19arylated dehydroabietylamine derivatives using a palladiumcatalyzed C(sp 3 )−H activation reaction. Five analogues (3b, 3d, 3h, 3n, and 4a) exhibited antibacterial activity against Escherichia coli. Compound 4a exhibited strong inhibitory activity against DNA Topo II and Topo IV. Molecular docking modeling indicated that it can bind effectively to the target through interactions with amino acid residues. The synthesized compounds were tested in vitro for their antifungal activity against six common phytopathogenic fungi. The mechanism of action of compound 4c against Rhizoctorzia solani was investigated, revealing that it disrupts the morphology of the mycelium and enhances cell membrane permeability.

show abstract

Syntheses and high selective cytotoxicity of dehydroabietylamine C-ring nitration derivatives

Cited by 5 publications

References 36 publications

Research on Anthocyanins from Rubus “Shuofeng” as Potential Antiproliferative and Apoptosis-Inducing Agents

Research on Anthocyanins from Rubus “Shuofeng” as Potential Antiproliferative and Apoptosis-Inducing Agents

The Extraction and High Antiproliferative Effect of Anthocyanin from Gardenblue Blueberry

Discovery of Dehydroabietylamine Derivatives as Antibacterial and Antifungal Agents

Contact Info

Product

Resources

About