Novel nortriterpenoids with new skeletons and limonoids from the fruits of Evodia rutaecarpa and their bioactivities

Shi, Yu-Sheng; Xia, Hong-Min; Wu, Chuanhai; Li, Chunbin; Duan, Chenchen; Che, Chang; Zhang, Xue‐Jing; Li, Hao-Tian; Zhang, Yan; Zhang, Xu-Fu

doi:10.1016/j.fitote.2020.104503

Cited by 10 publications

(5 citation statements)

References 15 publications

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“…In recent years, three new limonoids, such as evorubodinin ( 149 ), shihulimonin A ( 150 ) [ 73 ], and 6 α -acetoxyl-12 α -hydroxyevodol ( 143 ) [ 62 ], were first found from Euodiae Fructus, together with 12 known limonoids. Lately, an investigation of the 95% ethanol extract of Euodiae Fructus yielded two known limonoids (7-deacetylproceranone ( 156 ) and nomilin ( 157 )), two novel nortriterpenoids (evoditrilones A ( 165 ) and B ( 166 )), and three known triterpenoids (oleanic acid ( 164 ), ursolic acid ( 167 ), and 3 β -hydroxyoleana-11,13(18)-diene ( 168 )) [ 70 ]. Other triterpenoids mainly include 12-ursen-3-ol ( 159 ), 14-ursen-3-ol-1-one ( 160 ), glycyrrhizic acid ( 161 ), glycyrrhetinic ( 162 ) and taraxerone ( 163 ) [ 75 ].…”

Section: Phytochemistrymentioning

confidence: 99%

Traditional Chinese medicine Euodiae Fructus: botany, traditional use, phytochemistry, pharmacology, toxicity and quality control

Xiao¹,

Xu²,

Chen³

et al. 2023

Nat. Prod. Bioprospect.

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Euodiae Fructus, referred to as “Wuzhuyu” in Chinese, has been used as local and traditional herbal medicines in many regions, especially in China, Japan and Korea, for the treatment of gastrointestinal disorders, headache, emesis, aphtha, dermatophytosis, dysentery, etc. Substantial investigations into their chemical and pharmacological properties have been performed. Recently, interest in this plant has been focused on the different structural types of alkaloids like evodiamine, rutaecarpine, dehydroevodiamine and 1-methyl-2-undecyl-4(1H)-quinolone, which exhibit a wide range of pharmacological activities in preclinical models, such as anticancer, antibacterial, anti-inflammatory, anti-cardiovascular disease, etc. This review summarizes the up-to-date and comprehensive information concerning the botany, traditional uses, phytochemistry, pharmacology of Euodiae Fructus together with the toxicology and quality control, and discusses the possible direction and scope for future research on this plant.

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Section: Phytochemistrymentioning

confidence: 99%

Traditional Chinese medicine Euodiae Fructus: botany, traditional use, phytochemistry, pharmacology, toxicity and quality control

Xiao¹,

Xu²,

Chen³

et al. 2023

Nat. Prod. Bioprospect.

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“…The friedelane-type backbone is derived from the oleanane type by methyl translocation [145] (Figure 5). Representative sources of PTs are Betula pubescens (white birch) for lupane [146], Malus domestica (apple), Coffea arabica (arabic coffee), and Origanum vulgare (oregano) for ursane [147], Glycyrrhiza glabra (licorice), Olea europaea (olive), and Evodia rutaecarpa (evodia) for oleanane [148][149][150], and Tripterygium wilfordii and Celastrus orbiculatus (oriental bittersweet) for friedelane [151,152]. However, the diversity of PTs is not limited to these species; they can be found in many food and medicinal plants.…”

Section: Inhibitory Effect Of Triterpenoids On Inflammation-induced E...mentioning

confidence: 99%

“…The friedelane-type backbone is derived from the oleanane type by methyl translocation [145] (Figure 5). Representative sources of PTs are Betula pubescens (white birch) for lupane [146], Malus domestica (apple), Coffea arabica (arabic coffee), and Origanum vulgare (oregano) for ursane [147], Glycyrrhiza glabra (licorice), Olea europaea (olive), and Evodia rutaecarpa (evodia) for oleanane [148][149][150], and Tripterygium wilfordii and Celastrus orbicu- In plant cells, the mevalonate and methylerythritol phosphate pathways provide isoprene units in the form of isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are used as building blocks for the production of squalene. Oxidation of squalene yields 2,3-oxidosqualene, which serves as a precursor for the synthesis of all types of PT scaffolds, including lupane, ursane, oleanane, and friedelane.…”

Section: Inhibitory Effect Of Triterpenoids On Inflammation-induced E...mentioning

confidence: 99%

“…In addition, CDDO inhibited the expression of the mesenchymal markers fibronectin, α-SMA, and collagen I, as well as the deposition of collagen fibers in the lungs of irradiated mice, suggesting that CDDO inhibits the EMT in lung epithelial cells in mice with radiation-induced lung fibrosis [173]. Pristimerin isolated from Celastraceae plants and evoditrilone A isolated from Evodia rutaecarpa were reported to inhibit migration ability and regulate EMT-associated markers in H1299 and A549 cells, respectively [148,151]. The exact mechanisms of the EMT-inhibitory activity of cyanoenone-bearing PTs, as well as pristimerin and evoditrilone A, remain to be elucidated.…”

Section: Oleanane-and Friedelane-type Triterpenoidsmentioning

confidence: 99%

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The Nexus of Inflammation-Induced Epithelial-Mesenchymal Transition and Lung Cancer Progression: A Roadmap to Pentacyclic Triterpenoid-Based Therapies

Odarenko,

Zenkova,

Markov

2023

IJMS

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Lung cancer is the leading cause of cancer-related death worldwide. Its high mortality is partly due to chronic inflammation that accompanies the disease and stimulates cancer progression. In this review, we analyzed recent studies and highlighted the role of the epithelial–mesenchymal transition (EMT) as a link between inflammation and lung cancer. In the inflammatory tumor microenvironment (iTME), fibroblasts, macrophages, granulocytes, and lymphocytes produce inflammatory mediators, some of which can induce EMT. This leads to increased invasiveness of tumor cells and self-renewal of cancer stem cells (CSCs), which are associated with metastasis and tumor recurrence, respectively. Based on published data, we propose that inflammation-induced EMT may be a potential therapeutic target for the treatment of lung cancer. This prospect is partially realized in the development of EMT inhibitors based on pentacyclic triterpenoids (PTs), described in the second part of our study. PTs reduce the metastatic potential and stemness of tumor cells, making PTs promising candidates for lung cancer therapy. We emphasize that the high diversity of molecular mechanisms underlying inflammation-induced EMT far exceeds those that have been implicated in drug development. Therefore, analysis of information on the relationship between the iTME and EMT is of great interest and may provide ideas for novel treatment approaches for lung cancer.

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“…They can be traced to the effects of numerous marine compounds from different classes of constituents such as alkaloids, terpenoids, steroids, flavonoids, peptides, proteins, polyphenols, carotenoids, vitamins, tocopherols, tocotrienols, peptides, carbohydrates, etc. Not only marine compounds, but also terrestrial plant constituents have anticancer properties [ 1 , 2 , 3 , 4 , 5 ], as well as a plethora of other biological activities. The activities of these compounds have been screened in various disease conditions including cancer using in vivo or in vitro methods, and the documented evidence of these activities is reviewed regularly [ 6 , 7 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Marine Secondary Metabolites Worthy of Development as Anticancer Agents: A Review

et al. 2021

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Secondary metabolites from marine sources have a wide range of biological activity. Marine natural products are promising candidates for lead pharmacological compounds to treat diseases that plague humans, including cancer. Cancer is a life-threatening disorder that has been difficult to overcome. It is a long-term illness that affects both young and old people. In recent years, significant attempts have been made to identify new anticancer drugs, as the existing drugs have been useless due to resistance of the malignant cells. Natural products derived from marine sources have been tested for their anticancer activity using a variety of cancer cell lines derived from humans and other sources, some of which have already been approved for clinical use, while some others are still being tested. These compounds can assault cancer cells via a variety of mechanisms, but certain cancer cells are resistant to them. As a result, the goal of this review was to look into the anticancer potential of marine natural products or their derivatives that were isolated from January 2019 to March 2020, in cancer cell lines, with a focus on the class and type of isolated compounds, source and location of isolation, cancer cell line type, and potency (IC50 values) of the isolated compounds that could be a guide for drug development.

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Novel nortriterpenoids with new skeletons and limonoids from the fruits of Evodia rutaecarpa and their bioactivities

Cited by 10 publications

References 15 publications

Traditional Chinese medicine Euodiae Fructus: botany, traditional use, phytochemistry, pharmacology, toxicity and quality control

Traditional Chinese medicine Euodiae Fructus: botany, traditional use, phytochemistry, pharmacology, toxicity and quality control

The Nexus of Inflammation-Induced Epithelial-Mesenchymal Transition and Lung Cancer Progression: A Roadmap to Pentacyclic Triterpenoid-Based Therapies

Novel Marine Secondary Metabolites Worthy of Development as Anticancer Agents: A Review

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