Chemical constituents from the fruits of Ligustrum japonicum and their inhibitory effects on T cell activation

Ngo, Quynh-Mai Thi; Lee, Hyun Su; Nguyen, Van Thu; Kim, Jeong Ah; Woo, Mi Hee; Min, Byung Sun

doi:10.1016/j.phytochem.2017.06.001

Cited by 27 publications

(14 citation statements)

References 46 publications

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“…17 Compound 1 has been reported as a new compound in our previous study. 2 Thirteen isolated triterpenoids (1 -13) were evaluated for cytotoxic effects on Hela and HL-60 cell lines. As results, 8 (oleanolic acid) showed significant activities against Hela cells with IC 50 values of 5.5 µM, and moderate activities against and HL-60 cells with IC 50 values of 55.9 µM (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…1 Our previous study reported the isolation of triterpenoids, secoiridoids, and lignans from the fruits of L. japonicum. 2 A large number of phytochemicals, including triterpenoids, have been reported to have significant inhibitory activities against cancer cells. Triterpenoids, which consist 30 carbons and biosynthesized from isoprene units, have been considered as potentially cytotoxic compounds leading to complementary and alternative cancer treatments with low toxicities against normal cells.…”

Section: Introductionmentioning

confidence: 99%

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Cytotoxic Triterpenoids from the Fruits of Ligustrum japonicum

et al. 2018

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Medicinal plants are potential sources of anticancer agents screening. A large number of phytochemicals, including triterpenoids, have been reported to have significant cytotoxic effects on cancer cells. From the fruits of Ligustrum japonicum Thunb., thirteen triterpenoids (1-13) were isolated and evaluated for their cytotoxic activity against Hela and HL-60 cells. As results, 8 (oleanolic acid) showed significant effects on Hela with IC 50 values of 5.5 µM, and moderate effects on HL-60 cells with IC 50 values of 55.9 µM. Meanwhile, 10 (oleanderic acid) and 11 (3β-acetoxy-urs-12-en-28-oic acid) exhibited moderate inhibitory effects on Hela with IC 50 value of 55.0 and 68.8 µM, respectively. Moreover, 10 showed cytotoxic effect on HL-60 cell line with IC 50 value of 63.9 µM. To our knowledge, this is the first report that oleanderic acid was isolated from L. japonicum and investigated in cytotoxic effects on Hela and HL-60 cells.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cytotoxic Triterpenoids from the Fruits of Ligustrum japonicum

et al. 2018

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“…(Fouquieraceae) 37 , with its 13 C NMR data presented in the literature 19 . However, detailed information about its configuration and complete assignments of its NMR spectroscopic data have not been reported 38 . A C 30 H 52 O 3 molecular formula deduced from the HRESIMS and NMR spectroscopic data, along with seven tertiary methyl groups at δ H 0.77, 0.84, 0.88, 0.96, 0.97, 1.15, and 1.73 (singlets, 3H each) exhibited in the 1 H NMR spectrum, indicated a tetracyclic triterpene for 2 , which contains three hydroxyl groups and a double bond, as supported by its UV (λ max 201 nm) and IR (ν max 3418 and 1667 cm −1 ) spectra.…”

Section: Resultsmentioning

confidence: 99%

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

Ren

Anaya-Eugenio

Czarnecki

et al. 2018

Bioorganic & Medicinal Chemistry

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Syzygium is a large genus of flowering plants, with several species, including the clove tree, used as important resources in the food and pharmaceutical industries. In our continuing search for anticancer agents from higher plants, a chloroform extract of the leaves and twigs of Syzygium corticosum collected in Vietnam was found to be active toward the HT-29 human colon cancer cell line. Separation of this extract guided by HT-29 cells and nuclear factor-kappa B (NF-κB) inhibition yielded 19 known natural products, including seven triterpenoids, three ellagic acid derivatives, two methylated flavonoids, a cyclohexanone, four megastigmanes, a small lactone, and an aromatic aldehyde. The full stereochemistry of (+)-fouquierol (2) was defined for the first time. Biological investigations showed that (+)-ursolic acid (1) is the major cytotoxic component of S. corticosum, which exhibited also potent activities in the NF-κB and mitochondrial transmembrane potential (MTP) inhibition assays conducted, with IC values of 31 nM and 3.5 µM, respectively. Several analogues of (+)-ursolic acid (1) were synthesized, and a preliminary structure-activity relationship (SAR) study indicated that the C-3 hydroxy and C-28 carboxylic acid groups and 19,20-dimethyl substitution are all essential in the mediation of the bioactivities observed for this triterpenoid.

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“…There is growing evidence that specific bioactive compounds present in plants used as spices, fruits, vegetables, and nuts can be effective against some cancers. Secoiridoids, isolated from Oleaceae family, which are now widely used in the fields of food and medicine, have been extensively investigated in recent years and have been shown to possess a variety of pharmacological effects [24][25][26][27][28][29], such as anti-diabetic [30,31], anti-oxidant [32,33], anti-inflammatory [34][35][36], immunosuppressive [37], neuroprotective [36,38,39], and anti-cancer [1,[40][41][42]. Multifloroside (4), together with 10-hydroxyoleoside 11-methyl ester (1), 10-hydroxyoleoside dimethyl ester (2), and 10-hydroxyligustroside (3), are all 10-oxyderivatives of oleoside secoiridoids.…”

Section: Discussionmentioning

confidence: 99%

Multifloroside Suppressing Proliferation and Colony Formation, Inducing S Cell Cycle Arrest, ROS Production, and Increasing MMP in Human Epidermoid Carcinoma Cell Lines A431

Zhang

Feng

et al. 2019

Molecules

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Multifloroside (4), together with 10-hydroxyoleoside 11-methyl ester (1), 10-hydroxyoleoside dimethyl ester (2), and 10-hydroxyligustroside (3), are all secoiridoids, which are naturally occurring compounds that possess a wide range of biological and pharmacological activities. However, the anti-cancer activity of 1-4 has not been evaluated yet. The objective of this work was to study the anti-cancer activities of 1-4 in the human epidermoid carcinoma cell lines A431 and the human non-small cell lung cancer (NSCLC) cell lines A549. The results indicate that 1-4 differ in potency in their ability to inhibit the proliferation of human A431 and A549 cells, and multifloroside (4) display the highest inhibitory activity against A431 cells. The structure-activity relationships suggest that the o-hydroxy-p-hydroxy-phenylethyl group may contribute to the anti-cancer activity against A431 cells. Multifloroside treatment can also inhibit cell colony formation, arrest the cell cycle in the S-phase, increase the levels of reactive-oxygen-species (ROS), and mitochondrial membrane potential (MMP), but it did not significantly induce cell apoptosis at low concentrations. The findings indicated that multifloroside (4) has the tendency to show selective anti-cancer effects in A431 cells, along with suppressing the colony formation, inducing S cell cycle arrest, ROS production, and increasing MMP.

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Chemical constituents from the fruits of Ligustrum japonicum and their inhibitory effects on T cell activation

Cited by 27 publications

References 46 publications

Cytotoxic Triterpenoids from the Fruits of Ligustrum japonicum

Cytotoxic Triterpenoids from the Fruits of Ligustrum japonicum

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

Multifloroside Suppressing Proliferation and Colony Formation, Inducing S Cell Cycle Arrest, ROS Production, and Increasing MMP in Human Epidermoid Carcinoma Cell Lines A431

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