Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives

Ren, Yulin; Anaya-Eugenio, Gerardo D.; Czarnecki, Austin; Ninh, Tran Ngoc; Yuan, Chunhua; Chai, Hee Byung; Soejarto, Djaja D.; Burdette, Joanna E.; Blanco, Esperanza J. Carcache de; Kinghorn, A. Douglas

doi:10.1016/j.bmc.2018.07.025

Cited by 40 publications

(28 citation statements)

References 51 publications

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“…A recent review report elegantly explains the context-dependent role of autophagy on cancer [14]. The modulation of autophagy, or the molecules involved in the signaling pathways that trigger autophagy, could be targets for investigating and discovering new anticancer agents [15,16]. In that perspective, it has been reported that ursolic and oleanolic acids stimulate autophagy in cancer cells [3,17,18,19].…”

Section: Introductionmentioning

confidence: 99%

Ursolic and Oleanolic Acids Induce Mitophagy in A549 Human Lung Cancer Cells

et al. 2019

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Ursolic and oleanolic acids are natural isomeric triterpenes known for their anticancer activity. Here, we investigated the effect of triterpenes on the viability of A549 human lung cancer cells and the role of autophagy in their activity. The induction of autophagy, the mitochondrial changes and signaling pathway stimulated by triterpenes were systematically explored by confocal microscopy and western blotting. Ursolic and oleanolic acids induce autophagy in A549 cells. Ursolic acid activates AKT/mTOR pathways and oleanolic acid triggers a pathway independent on AKT. Both acids promote many mitochondrial changes, suggesting that mitochondria are targets of autophagy in a process known as mitophagy. The PINK1/Parkin axis is a pathway usually associated with mitophagy, however, the mitophagy induced by ursolic or oleanolic acid is just dependent on PINK1. Moreover, both acids induce an ROS production. The blockage of autophagy with wortmannin is responsible for a decrease of mitochondrial membrane potential (Δψ) and cell death. The wortmannin treatment causes an over-increase of p62 and Nrf2 proteins promote a detoxifying effect to rescue cells from the death conducted by ROS. In conclusion, the mitophagy and p62 protein play an important function as a survival mechanism in A549 cells and could be target to therapeutic control.

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Section: Introductionmentioning

confidence: 99%

Ursolic and Oleanolic Acids Induce Mitophagy in A549 Human Lung Cancer Cells

et al. 2019

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“…The freeze dried fruit pulp also induced cell death in different breast cancer cell lines (MCF-7, MCF-10A, and MDA-MB-231) [ 21 ]. Ren et al [ 22 ] studied the NF-κB and mitochondrial transmembrane potential inhibitory effects of ursolic acid (31 nM) isolated from S. corticosum . All these study reports reveal the cytotoxic properties of phenolic compounds.…”

Section: Discussionmentioning

confidence: 99%

Anti-Proliferative, Analgesic and Anti-Inflammatory Properties of Syzygium mundagam Bark Methanol Extract

2020

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Cancer, pain and inflammation have long been a cause for concern amongst patients, clinicians and research scientists. There is an alarming increase in the demand for medicines suppressing these disease conditions. The present study investigates the role of Syzygium mundagam bark methanol (SMBM) extract against MCF-7 breast cancer cells, pain and inflammation. The MCF-7 cells treated with SMBM were analyzed for adenosine triphosphate (ATP), lactate dehydrogenase (LDH) levels, changes in cell morphology and nuclear damage. Hot plate, acetic acid and formalin-induced pain models were followed to determine the analgesic activity. Anti-inflammatory activity was studied using carrageenan, egg albumin and cotton pellet induced rat models. Microscopic images of cells in SMBM treated groups showed prominent cell shrinkage and nuclear damage. Hoechst stain results supported the cell death morphology. The decline in ATP (47.96%) and increased LDH (40.96%) content indicated SMBM induced toxicity in MCF-7 cells. In the in vivo study, a higher dose (200 mg/kg) of the extract was found to be effective in reducing pain and inflammation. The results are promising and the action of the extract on MCF-7 cells, pain and inflammation models indicate the potential of drugs of natural origin to improve current therapies.

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“…A large number of studies had reported that triterpenoids have potential antitumor activity, including examples of lupane-, oleanane-, and ursane-type triterpenoids. Previous studies had confirmed that ursane-type triterpenoids have extensive anti-inflammatory, antibacterial, antifungal, and antitumor activities [45][46][47][48]. However, the antitumor effect of ursane-type triterpenoids from the F. palmata had not been reported, especially the anticervical cancer effect of ursane-type triterpenoid compound 10.…”

Section: Cytotoxicmentioning

confidence: 99%

Antioxidant, Anti-Inflammatory, and Cytotoxic Properties and Chemical Compositions of Filipendula palmata (Pall.) Maxim.

Zhang

Han

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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Filipendula palmata (Pall.) Maxim. remains unexplored and underutilized resources with a high potential to improve human health. In this study, a new ursane-type triterpenoid, namely, 2α, 3β-dihydroxyurs-12-en-28-aldehyde (compound 10), and other 23 known compounds were isolated. 5 triterpenoids (compounds 6, 8, and 10–12), 11 flavonoids (compounds 13–15 and 17–24), 6 phenolic compounds (compounds 1, 2, 4, 5, 9, and 16), 2 sterols (compounds 3 and 7) were isolated from the aqueous solution extract of the aerial parts of F. palmata. The structures of all compounds were elucidated by the use of extensive spectroscopic methods such as infrared spectroscopy (IR), high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1H-NMR, and 13C-NMR. The solvent extractions of ethyl acetate fraction were evaluated for antioxidant activities using DPPH (2, 2-diphenyl-1-picrylhydrazyl) and ABTS+ (2, 2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)) methods. The anti-inflammatory effects of the compounds were evaluated in lipopolysaccharide- (LPS-) stimulated RAW 264.7 macrophages. The extract cytotoxicity on the cancer cell lines MCF-7, HeLa, 4T1, and A549 was determined by MTT assay. As a result, compounds 10, 11, and 12 exhibited better antioxidant activity compared to the other compounds. Compounds 8–24 had different inhibitory effects on the release of NO, TNF-α, and IL-6 in LPS-stimulated RAW 264.7 cells. The new compound has shown a significant inhibiting effect on cancer cells, and the cell inhibition rate increased in a dose-dependent manner. Further research to elucidate the chemical compositions and pharmacological effects of F. palmata is of major importance towards the development and foundation of clinical application of the species.

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Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives

Cited by 40 publications

References 51 publications

Ursolic and Oleanolic Acids Induce Mitophagy in A549 Human Lung Cancer Cells

Ursolic and Oleanolic Acids Induce Mitophagy in A549 Human Lung Cancer Cells

Anti-Proliferative, Analgesic and Anti-Inflammatory Properties of Syzygium mundagam Bark Methanol Extract

Antioxidant, Anti-Inflammatory, and Cytotoxic Properties and Chemical Compositions of Filipendula palmata (Pall.) Maxim.

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