Triterpene acids from Rosa roxburghii Tratt fruits exert anti-hepatocellular carcinoma activity via ROS/JNK signaling pathway-mediated cell cycle arrest and mitochondrial apoptosis

Zhai, Bo-Wen; Zhao, Heng; Zhu, Han-Lin; Huang, Han; Zhang, Maoyu; Fu, Yujie

doi:10.1016/j.phymed.2023.154960

Cited by 8 publications

(6 citation statements)

References 26 publications

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“…By NMR data analysis and comparison with the reported spectroscopic data, 22 known compounds were identified as rosamultic acid (2), 18 hyptadienic acid (3), 22 euscaphic acid (6), 19 kaji-ichigoside F1 (7), 23 1α,2β,3β,19α-tetrahydroxyurs-12-en-28-oic acid (8), 24 1-hydroxy-2-oxopomolic acid (9), 25 rosamultin (10), 26 pomolic acid (11), 27 fupenzic acid (12), 28 alpinoside (13), 29 2α,3α,24-trihydroxy-urs-12,18-diene-28-oic acid ( 14), 30 rubuside B (15), 12 rubuside A (16), 12 1β,2α,3α,19α-tetrahydroxyurs-12-en-28-oic acid β-D-glucopyranosyl ester (17), 31 Proposed Biosynthetic Pathways. To our knowledge, the formation of five-membered A-ring triterpenoids mainly occurred through two hypothetical biogenetic pathways: 3,4ring cleavage (a) and 2,3-ring cleavage (b).…”

Section: ■ Results and Discussionmentioning

confidence: 93%

“…Plant-derived triterpenoids make up a large class of natural products that possess diverse structural scaffolds and bioactivities. Triterpenoids are characteristic secondary compounds found particularly in family Rosaceae and are especially abundant in genera Rosa , Rubus , and Agrimonia . − Triterpenoids in Rosaceae have anti-inflammatory, antifungal, antitumor, and α-glucosidase inhibitory activities. − Triterpenoids reported from the family Rosaceae plants are interesting from the viewpoints of chemical diversity and biological activity.…”

Section: Introductionmentioning

confidence: 99%

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Anti-Inflammatory and α-Glucosidase Inhibitory Triterpenoid with Diverse Carbon Skeletons from the Fruits of Rosa roxburghii

Zhang,

Xiang,

Long

et al. 2024

J. Agric. Food Chem.

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The fruits of Rosa roxburghii Tratt. are edible nutritional food with high medicinal value and have been traditionally used as Chinese folk medicine for a long time. In this study, 26 triterpenoids including four new pentacyclic triterpenoids, roxbuterpenes A−D (1, 4, 5, and 24), along with 22 known analogues (2, 3, 6−23, 25, and 26), were isolated from the fruits of R. roxburghii. Their chemical structures were determined on the basis of extensive spectroscopic analyses (including IR, HRESIMS and NMR spectroscopy). The absolute configuration of roxbuterpene A (1) was determined by an X-ray crystallographic analysis. This is the first report of the crystal structure of 5/6/6/6/6-fused system pentacyclic triterpenoid. Notably, roxbuterpenes A and B (1 and 4) possessed the A-ring contracted triterpenoid and nortriterpenoid skeletons with a rare 5/6/6/6/6-fused system, respectively.

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Section: ■ Results and Discussionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory and α-Glucosidase Inhibitory Triterpenoid with Diverse Carbon Skeletons from the Fruits of Rosa roxburghii

Zhang,

Xiang,

Long

et al. 2024

J. Agric. Food Chem.

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“…As a major source of medicinal natural products, monoterpenes and sesquiterpenes of the genus Rosa mainly contribute to the aroma, and triterpenoids are one of its main functional components [ 47 , 48 , 49 , 50 ]. Among the 38 detected terpenoids, 37 exhibited significant differences among five Rosa samples which included four monoterpenes, two diterpenes, two sesquiterpenes and 29 triterpenoids ( Supplementary Table S4 ).…”

Section: Resultsmentioning

confidence: 99%

“…Accumulating evidence has indicated that corosolic acid exerts anti-diabetic, anti-obesity, anti-inflammatory, anti-hyperlipidemic and anti-viral effects. More importantly, corosolic acid has recently attracted much attention due to its anticancer properties and innocuous effects on normal cells [ 50 , 70 ]. Moreover, 3β-hydroxy-28-norurs-17,19,21-trien, terminolic acid, and isoceanothic acid were first reported in RSS-F and with more than twice the abundance than those in RRT-F.…”

Section: Discussionmentioning

confidence: 99%

UPLC-ESI-MS/MS-Based Analysis of Various Edible Rosa Fruits Concerning Secondary Metabolites and Evaluation of Their Antioxidant Activities

Ni,

Chen,

et al. 2024

Foods

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The genus Rosa is globally popular with well-established applications since it has a high edible and medicinal value. However, relatively limited research has been conducted on the composition and quality of wild Rosa fruits. The present study aimed to compare the properties and chemical components of five wild edible Rosa fruits, Rosa roxburghii, Rosa sterilis, Rosa laevigata, Rosa davurica, and Rosa sericea. The UPLC-ESI-MS/MS approach identified the key metabolites among the five Rosa fruits as flavonoids, phenolic acids, and organic acids. The main differential metabolites among the five fruits are flavonoids (22.29–45.13%), phenolic acids (17–22.27%), and terpenoids (7.7–24%), respectively. In total, 125 compounds served as potential markers for the five Rosa species. Differential metabolic pathways of five Rosa fruits were analyzed using the KEGG approach. Rosa laevigata fruits showed the highest total polysaccharide (TPS) content of 64.48 g/100 g. All the five Rosa extracts effectively decreased the levels of malondialdehyde while increasing the activities of superoxide dismutase and glutathione peroxidase in the H2O2-induced HaCaT cell model, demonstrating high potential for antioxidant development. Our findings suggest that the five studied Rosa fruits exhibit biological activity and edible value worth further exploration.

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“…The comprehensive score (S) was then weighted and combined as follows: S = 0.5X + 0.5Y 3.4.6. Single-Factor Test Polysaccharide solutions of 5 mg/mL were prepared, and keeping all other factors constant, the effects of decoloration time (1.0, 2.0, 3.0, 4.0, 5.0 h), resin content (1.0, 2.0, 3.0, 4.0, 5.0 g), and decoloration temperature (30,40,50,60,70 • C) were assessed on both the rate of polysaccharide pigment removal and polysaccharide retention.…”

Section: Comprehensive Scorementioning

confidence: 99%

Inhibition of Proliferation and Induction of Apoptosis in Prostatic Carcinoma DU145 Cells by Polysaccharides from Yunnan Rosa roxburghii Tratt

Yang,

Chen

2024

Molecules

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Objective: This study aimed to investigate methodologies for the extraction and purification of polysaccharides from Rosa roxburghii Tratt fruits and their impact on various cellular processes in prostate cancer DU145 cells, including survival rate, migration, invasion, cell cycle, and apoptosis. Results: Compared to the control group, the polysaccharide exhibited a significant reduction in the viability, migration, and invasion rates of DU145 cells in a time- and dose-dependent manner within the polysaccharide-treated groups. Additionally, it effectively arrested the cell cycle of DU145 cells at the G0/G1 phase by downregulating the expressions of CDK-4, CDK-6, and Cyclin D1. Furthermore, it induced apoptosis by upregulating the expressions of Caspase 3, Caspase 8, Caspase 9, and BAX. Methods: Polysaccharides were extracted from Rosa roxburghii Tratt sourced from Yunnan, China. Extraction and decolorization methods were optimized using response surface methodology, based on a single-factor experiment. Polysaccharide purification was carried out using DEAE-52 cellulose and Sephadex G-100 column chromatography. The optimal dosage of R. roxburghii Tratt polysaccharide affecting DU145 cells was determined using the CCK-8 assay. Cell migration and invasion were assessed using transwell and scratch assays. Flow cytometry was employed to analyze the effects on the cell cycle and apoptosis. Western blotting and Quantitative real-time PCR were utilized to examine protein and mRNA expressions in DU145 cells, respectively. Conclusions: Rosa roxburghii Tratt polysaccharides, consisting of D-mannose, L-rhamnose, N-acetyl-D-glucosamine, D-galacturonic acid, D-glucose, D-galactcose, D-xylose, L-arabinose, and L-fucose, possess the ability to hinder DU145 cell proliferation, migration, and invasion while inducing apoptosis through the modulation of relevant protein and gene expressions.

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Triterpene acids from Rosa roxburghii Tratt fruits exert anti-hepatocellular carcinoma activity via ROS/JNK signaling pathway-mediated cell cycle arrest and mitochondrial apoptosis

Cited by 8 publications

References 26 publications

Anti-Inflammatory and α-Glucosidase Inhibitory Triterpenoid with Diverse Carbon Skeletons from the Fruits of Rosa roxburghii

Anti-Inflammatory and α-Glucosidase Inhibitory Triterpenoid with Diverse Carbon Skeletons from the Fruits of Rosa roxburghii

UPLC-ESI-MS/MS-Based Analysis of Various Edible Rosa Fruits Concerning Secondary Metabolites and Evaluation of Their Antioxidant Activities

Inhibition of Proliferation and Induction of Apoptosis in Prostatic Carcinoma DU145 Cells by Polysaccharides from Yunnan Rosa roxburghii Tratt

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