Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

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Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

Molecules ◽

10.3390/molecules24081561 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1561 ◽

Cited By ~ 1

Author(s):

Qiao ◽

Khutsishvili ◽

Alizade ◽

Atha ◽

Borris

Keyword(s):

Cell Lines ◽

Human Tumor ◽

2D Nmr ◽

Human Tumor Cell Lines ◽

Abietane Diterpenoids ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Values ◽

First Time ◽

Mcf 7

A phytochemical investigation of the whole plant of Juniperus oblonga led to the isolationof one previously undescribed labdane diterpenoid, (4R,5S,9S,10R)‐13‐des‐ethyl‐13‐oxolabda‐8(17),11E‐dien‐19‐oic acid (1), together with nine known diterpenoids (2–3, 6–12), two lignans (4, 5),and a coumarin (13). The structures of all the compounds were elucidated on the basis ofspectrometric data, primarily one‐dimensional (1D)‐ and two‐dimensional (2D)‐NMR and massspectrometry. Electronic circular dichroism (ECD) calculations determined the absoluteconfiguration of 1. In addition, the isolated compounds were evaluated for their cytotoxic activityagainst three human tumor cell lines (HepG2, MCF‐7, and HeLa). 6,12‐Dihydroxyabieta‐5,8,11,13‐tetraen‐7‐one (6) showed moderate cytotoxicity against all three cell lines with IC50 values rangingfrom 24.41 μM to 58.39 μM and trilobinone (10) showed weaker activity with IC50 values rangingfrom 56.93 μM to 79.98 μM. None of the isolated diterpenoids have been previously reported fromJuniperus oblonga, and five compounds are here reported from the genus Juniperus for the first time.

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Chemical Constituents from Scindapsus officinalis (Roxb.) Schott. and Their Anti–Inflammatory Activities

Molecules ◽

10.3390/molecules23102577 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2577 ◽

Cited By ~ 2

Author(s):

Hongjing Dong ◽

Yanling Geng ◽

Xueyong Wang ◽

Xiangyun Song ◽

Xiao Wang ◽

...

Keyword(s):

Chemical Constituents ◽

2D Nmr ◽

No Production ◽

Inhibitory Effects ◽

Nmr Data ◽

Extensive Analysis ◽

Ic50 Values ◽

Monoterpene Glycoside ◽

Anti Inflammatory

One new monoterpene glycoside (1), one new phenyl glycoside (2), one new caffeoyl derivative (3), were isolated from Scindapsus officinalis (Roxb.) Schott., along with four known compounds (4–7). Structures of the isolated compounds were elucidated by extensive analysis of spectroscopic data, especially 2D NMR data and comparison with literatures. All isolates were evaluated for anti-inflammatory activity against nitric oxide (NO) production in vitro. Compounds 3 and 7 exhibited moderate inhibitory effects on NO production with IC50 values of 12.2 ± 0.8 and 18.9 ± 0.3 μM, respectively.

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Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽

10.3390/molecules24183336 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3336 ◽

Cited By ~ 2

Author(s):

Ping-Chen Tu ◽

Han-Chun Tseng ◽

Yu-Chia Liang ◽

Guan-Jhong Huang ◽

Te-Ling Lu ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Isolation And Characterization ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Anti Inflammatory ◽

New Compounds ◽

First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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Streptoglycerides E–H, Unsaturated Polyketides from the Marine-Derived Bacterium Streptomyces specialis and Their Anti-Inflammatory Activity

Marine Drugs ◽

10.3390/md20010044 ◽

2022 ◽

Vol 20 (1) ◽

pp. 44

Author(s):

Hee Jae Shin ◽

Chang-Su Heo ◽

Cao Van Anh ◽

Yeo Dae Yoon ◽

Jong Soon Kang

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

Ring System ◽

Membered Ring ◽

Inflammatory Activity ◽

Raw 264.7 Cells ◽

No Production ◽

Nmr Data ◽

Ic50 Values ◽

Anti Inflammatory

Four new streptoglycerides E–H (1–4), with a rare 6/5/5/-membered ring system, were isolated from a marine-derived actinomycete Streptomyces specialis. The structures of 1–4 were elucidated by detailed analysis of HRESIMS, 1D and 2D NMR data and ECD spectra as well as comparison of their spectroscopic data with those reported in literature. Compounds 1–4 showed significant anti-inflammatory activity by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production in Raw 264.7 cells with IC50 values ranging from 3.5 to 10.9 µM. Especially, 2 suppressed mRNA expression levels of iNOS and IL-6 without cytotoxicity.

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Novel Efficient Bioprocessing of Marine Chitins into Active Anticancer Prodigiosin

Marine Drugs ◽

10.3390/md18010015 ◽

2019 ◽

Vol 18 (1) ◽

pp. 15 ◽

Cited By ~ 9

Author(s):

Van Bon Nguyen ◽

Shan-Ping Chen ◽

Thi Hanh Nguyen ◽

Minh Trung Nguyen ◽

Thi Thanh Thao Tran ◽

...

Keyword(s):

Serratia Marcescens ◽

Bioactive Compound ◽

Potential Candidate ◽

Hep G2 ◽

Anticancer Activities ◽

Anti Cancer ◽

Initial Ph ◽

Ic50 Values ◽

First Time ◽

Mcf 7

Marine chitins (MC) have been utilized for the production of vast array of bioactive products, including chitooligomers, chitinase, chitosanase, antioxidants, anti-NO, and antidiabetic compounds. The aim of this study is the bioprocessing of MC into a potent anticancer compound, prodigiosin (PG), via microbial fermentation. This bioactive compound was produced by Serratia marcescens TKU011 with the highest yield of 4.62 mg/mL at the optimal conditions of liquid medium with initial pH of 5.65–6.15 containing 1% α-chitin, 0.6% casein, 0.05% K2HPO4, and 0.1% CaSO4. Fermentation was kept at 25 °C for 2 d. Notably, α-chitin was newly investigated as the major potential material for PG production via fermentation; the salt CaSO4 was also found to play the key role in the enhancement of PG yield of Serratia marcescens fermentation for the first time. PG was qualified and identified based on specific UV, MALDI-TOF MS analysis. In the biological activity tests, purified PG demonstrated potent anticancer activities against A549, Hep G2, MCF-7, and WiDr with the IC50 values of 0.06, 0.04, 0.04, and 0.2 µg/mL, respectively. Mytomycin C, a commercial anti-cancer compound was also tested for comparison purpose, showing weaker activity with the IC50 values of 0.11, 0.1, 0.14, and 0.15 µg/mL, respectively. As such, purified PG displayed higher 2.75-fold, 1.67-fold, and 3.25-fold efficacy than Mytomycin C against MCF-7, A549, and Hep G2, respectively. The results suggest that marine chitins are valuable sources for production of prodigiosin, a potential candidate for cancer drugs.

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Isolation and Identification of Lignans and Other Phenolic Constituents from the Stem Bark of Albizia julibrissin Durazz and Evaluation of Their Nitric Oxide Inhibitory Activity

Molecules ◽

10.3390/molecules25092065 ◽

2020 ◽

Vol 25 (9) ◽

pp. 2065

Author(s):

Wei Li ◽

Hye Jin Yang

Keyword(s):

Nitric Oxide ◽

Stem Bark ◽

No Production ◽

Isolation And Identification ◽

Albizia Julibrissin ◽

Chemical Structures ◽

Phenolic Constituents ◽

Ic50 Values ◽

First Time

A dibenzylbutane-type lignan (16), along with eight furofuran-type (1–8), five furan-type (9–13), two dibenzylbutane-type (14 and 15), two bibenztetrahydronaphthalene-type lignans (17 and 18), two neolignans (19 and 20), and six phenolic derivatives (21–26) were isolated from an MeOH extract of the stem bark of Albizia julibrissin Durazz. The chemical structures of the obtained compounds were elucidated by nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. Of the evaluated compounds, 14 were isolated from A. julibrissin and the Fabaceae family for the first time. Anti-inflammatory effects of the isolated analogs were investigated in terms of the inhibition of the nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated murine RAW264.7 macrophage cells. Ten compounds (10–12, 14, and 17–22) displayed significant dose-dependent inhibitory effects against the NO production, with IC50 values ranging from 5.4 to 19.2 µM. Moreover, eight compounds (1–4, 9, 13, 15, and 16) exhibited moderate inhibitory activities, with IC50 values ranging from 21.0 to 62.5 µM.

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Bioactive PKS–NRPS Alkaloids from the Plant-Derived Endophytic Fungus Xylaria arbuscula

Molecules ◽

10.3390/molecules27010136 ◽

2021 ◽

Vol 27 (1) ◽

pp. 136

Author(s):

Ya Wang ◽

Sinan Zhao ◽

Tao Guo ◽

Li Li ◽

Tantan Li ◽

...

Keyword(s):

Endophytic Fungus ◽

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

Hep G2 ◽

Antitumor Activities ◽

Chemical Structures ◽

Spectroscopic Analyses ◽

Ic50 Values

A novel hybrid PKS–NRPS alkaloid, xylarialoid A (1), containing a 13-membered macrocyclic moiety and [5,5,6] fused tricarbocyclic rings, together with ten known cytochalasins (2–11), was isolated from a plant-derived endophytic fungus, Xylaria arbuscula. The chemical structures of all compounds were elucidated using 1D and 2D NMR, HR ESIMS spectroscopic analyses, and electronic circular dichroism (ECD) calculation. Compounds 1–3 and 10 exhibited significant antitumor activities against A549 and Hep G2 cell lines, with IC50 values of 3.6–19.6 μM. In addition, compound 1 showed potent anti-inflammatory activity against LPS-induced nitric oxide (NO) production in macrophage RAW 264.7 cells (IC50, 6.6 μM).

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Structural Characterization and Assessment of Anti-Inflammatory and Anti-Tyrosinase Activities of Polyphenols from Melastoma normale

Molecules ◽

10.3390/molecules26133913 ◽

2021 ◽

Vol 26 (13) ◽

pp. 3913

Author(s):

Rui-Jie He ◽

Jun Li ◽

Yong-Lin Huang ◽

Ya-Feng Wang ◽

Bing-Yuan Yang ◽

...

Keyword(s):

Enzyme Inhibitors ◽

Enzyme Inhibitor ◽

Structure Identification ◽

No Production ◽

Protective Effects ◽

Successful Isolation ◽

Ic50 Values ◽

Development And Utilization ◽

Inhibitory Activities ◽

Anti Inflammatory

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme inhibitory activities of compounds from title plant. Using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, the extract of Melastoma normale roots was separated. Four new ellagitannins, Whiskey tannin C (1), 1-O-(4-methoxygalloyl)-6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (2), 1-O-galloyl-6-O-(3-methoxygalloyl)-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (3), and 1-O-galloyl-6-O-vanilloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (4), along with eight known polyphenols were firstly obtained from this plant. The structures of all isolates were elucidated by HRMS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW2 64.7 cells, we investigated the anti-inflammatory activities of compounds 1–4, unfortunately, none of them exhibit inhibit nitric oxide (NO) production, their IC50 values are all > 50 μM. Anti-tyrosinase activity assays was done by tyrosinase inhibition activity screening model. Compound 1 showed weak tyrosinase inhibitory activity with IC50 values of 426.02 ± 11.31 μM. Compounds 2–4 displayed moderate tyrosinase inhibitory activities with IC50 values in the range of 124.74 ± 3.12–241.41 ± 6.23 μM. The structure–activity relationships indicate that hydroxylation at C-3′, C-4′, and C-3 in the flavones were key to their anti-tyrosinase activities. The successful isolation and structure identification of ellagitannin provide materials for the screening of anti-inflammatory drugs and enzyme inhibitors, and also contribute to the development and utilization of M. normale.

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Cytokine and inflammatory mediators are associated with cytotoxic, anti-inflammatory and apoptotic activity of honeybee venom

Journal of Complementary and Integrative Medicine ◽

10.1515/jcim-2019-0182 ◽

2020 ◽

Vol 0 (0) ◽

Author(s):

Mohamed A. Salama ◽

Mohamed A. Younis ◽

Roba M. Talaat

Keyword(s):

Nitric Oxide ◽

Cell Lines ◽

Cancer Cell ◽

Hela Cells ◽

No Production ◽

Hep G2 ◽

Normal Cells ◽

Tnf Α ◽

Ifn Γ ◽

Mcf 7

AbstractObjectiveThe present study aimed to evaluate cytotoxic, apoptotic, and anti-inflammatory properties of bee venom (BV) as well as changes in cytokine secretion levels and nitric oxide (NO) production using three different cancer cell lines [liver (Hep-G2), breast (MCF-7), and cervical (HPV-18 infected HeLa cells)] and two normal cells (splenocytes and macrophages (MQ).MethodsCytotoxic activity of BV against tumor cell lines and normal splenocytes/MQ was tested by MTT assay. By ELISA (ELISA); Tumor necrosis factor (TNF-α), Interleukine (IL-10) and interferon (IFN-γ) were measured. Caspase three expressions was evaluated using reverse transcription-polymerase chain reaction (RT-PCR). Nitric oxide (NO) was estimated using a colorimetric assay.ResultsBV has a significant cytotoxic effect on all cell lines in a dose- and time-dependent manner; none of them was toxic for normal cells. Treating Hep-G2 cells with BV showed a reduction in IL-10, elevation in TNF-α with no change in IFN-γ level. MCF-7 cells have low IL-10 and TNF-α and high IFN-γ production level. Elevation of IL-10 and IFN-γ coincides with a reduction in TNF-α level was demonstrated in HeLa cells. The expression of Caspase three was dramatically increased with elevation in BV concentration in all tested cancer cell lines. A gradual decrease in NO production by MQ with increasing BV dose was observed.ConclusionTaken together, our results stressed on the importance of BV as a potent anti-tumor agent against various types of cancers (Liver, Breast, and Cervix). Further steps towards the use of BV for pharmacological purposes must be done.

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Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

Natural Product Communications ◽

10.1177/1934578x21993345 ◽

2021 ◽

Vol 16 (2) ◽

pp. 1934578X2199334

Author(s):

Do Thi Trang ◽

Bui Huu Tai ◽

Dan Thuy Hang ◽

Pham Hai Yen ◽

Phan Thi Thanh Huong ◽

...

Keyword(s):

Cytotoxic Activity ◽

Spectral Data ◽

Absolute Configuration ◽

Marine Sponge ◽

Chemical Constituents ◽

2D Nmr ◽

Extensive Analysis ◽

First Time ◽

Tddft Method ◽

Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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