Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

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.

Download Full-text

Saccharpiscinols A–C: Flavans with Potential Inflammatory Activities from One Actinobacteria Saccharomonospora piscinae

Molecules ◽

10.3390/molecules26164909 ◽

2021 ◽

Vol 26 (16) ◽

pp. 4909

Author(s):

Yung-Shun Su ◽

Jih-Jung Chen ◽

Ming-Jen Cheng ◽

Chee-Yin Chai ◽

Aij-Lie Kwan ◽

...

Keyword(s):

Data Analysis ◽

Chromatographic Separation ◽

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

Raw 264.7 ◽

Phytochemical Investigation ◽

Inhibitory Activities ◽

New Compounds ◽

First Time

Phytochemical investigation and chromatographic separation of extracts from the actinobacteria strain Saccharomonospora piscinae that was isolated from dried fishpond sediment of Kouhu township, in the south of Taiwan, led to the isolation of three new compounds, saccharpiscinols A–C (1–3, respectively), and three new natural products, namely (2S)-5,7,3′,4′-tetrahydroxy-6,8-dimethylflavanone (4), methyl-4-hydroxy-2-methoxy-6-methylbenzoate (5), and (±)-7-acetyl-4,8-dihydroxy-6-methyl-1-tetralone (6). Compounds 4–6 were reported before as synthesized products, herein, they are reported from nature for the first time. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Saccharpiscinol A showed inhibitory activities against LPS-induced NO production.

Download Full-text

Secondary Metabolites with Anti-Inflammatory Activities from One Actinobacteria Amycolatopsis taiwanensis

Molecules ◽

10.3390/molecules26195765 ◽

2021 ◽

Vol 26 (19) ◽

pp. 5765

Author(s):

Yung-Shun Su ◽

Ming-Der Wu ◽

Jih-Jung Chen ◽

Ming-Jen Cheng ◽

Yueh-Hsiung Kuo ◽

...

Keyword(s):

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

The North ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Production Activity ◽

Inos Inhibitor ◽

Ic50 Values ◽

New Compounds

Phytochemical investigation and chromatographic separation of extracts from one new actinobacteria strain Amycolatopsis taiwanensis that was isolated from soil of Yilan township, in the north of Taiwan, led to the isolation of nine new compounds, amycolataiwanensins A–I (1–9, resp.), and one new natural product, namely amycolataiwanensin J (10). The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic-data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Of the isolates, 3, 5, 7 and 8 exhibited potent anti-NO production activity, with IC50 values of 17.52, 12.31, 17.81 and 13.32 μM, respectively, compared to that of quercetin, an iNOS inhibitor with an IC50 value of 35.94 μM. This is the first report on indole metabolite from the genus Amycolatopsis.

Download Full-text

Acylphloroglucinol Derivatives from Garcinia multiflora with Anti-Inflammatory Effect in LPS-Induced RAW264.7 Macrophages

Molecules ◽

10.3390/molecules23102587 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2587 ◽

Cited By ~ 6

Author(s):

Lin-Yang Cheng ◽

Yun-Chen Tsai ◽

Shu-Ling Fu ◽

Ming-Jen Cheng ◽

Ping-Jyun Sung ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

Drug Candidate ◽

No Production ◽

Raw264.7 Macrophages ◽

Spectroscopic Analyses ◽

Anti Inflammatory ◽

New Compounds ◽

Relative Luciferase Activity ◽

Inflammatory Effect

Two new acylphloroglucinol derivatives, 13,14-didehydroxygarcicowin C (1) and 13,14-didehydroxyisoxanthochymol (2), have been isolated from the stems of Garcinia multiflora, together with seven known compounds (3–9). The structures of new compounds 1 and 2 were elucidated by MS and extensive 1D/2D NMR spectroscopic analyses. Among the isolates, 13,14-didehydroxy-isoxanthochymol (2) and sampsonione B (3) exhibited inhibition against lipopolysaccharide (LPS)-induced NF-κB activation in macrophages at 30 μM with relative luciferase activity values (inhibitory %) of 0.75 ± 0.03 (24 ± 4%) and 0.12 ± 0.03 (88 ± 4%), respectively. Additionally, sampsonione B (3) reduced LPS-induced nitric oxide (NO) production in murine RAW264.7 macrophages and did not induce cytotoxicity against RAW 264.7 cells after 24 h treatment. Compound 3 is worth further investigation and may be expectantly developed as an anti-inflammatory drug candidate.

Download Full-text

Azukisapogenol Triterpene Glycosides from Oxytropis chiliophylla Royle

Molecules ◽

10.3390/molecules23102448 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2448

Author(s):

Jun Wang ◽

Hongshuai Yang ◽

Yang Liu ◽

Kelsang Norbo ◽

Kewu Zeng ◽

...

Keyword(s):

Methyl Ester ◽

Glucuronic Acid ◽

Acid Methyl Ester ◽

Triterpene Glycosides ◽

Raw 264.7 Cells ◽

No Production ◽

Acid Methyl ◽

Potent Inhibition ◽

New Compounds ◽

First Time

Eight azukisapogenol triterpene glycosides, including five new compounds, oxychiliotriterpenosides A–E (1–5), two new methyl glucuronide derivatives that proved to be artifacts, oxychiliotriterpenoside E-glucuronic acid methyl ester (6) and myrioside B-glucuronic acid methyl ester (7), and a known one, myrioside B (8), was isolated from the aerial part of Oxytropis chiliophylla Royle. Their structures were elucidated based on extensive spectroscopic analyses and chemical methods. Triterpene glycosides were first obtained from O. chiliophylla, and those containing a galactose unit (1, 2, 5 and 6) and diglucosidic or triglucosidic linkage at C-29 (1–4), were reported from Oxytropis species for the first time, which might be recognized as a chemotaxonomic feature of O. chiliophylla. All isolated compounds were evaluated for their anti-inflammatory activities against NO production using lipopolysaccharide (LPS)-induced RAW 264.7 cells, but no compounds showed potent inhibition on NO production.

Download Full-text

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.

Download Full-text

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

Molecules ◽

10.3390/molecules26216626 ◽

2021 ◽

Vol 26 (21) ◽

pp. 6626

Author(s):

Edwin R. Sukandar ◽

Sutin Kaennakam ◽

Pia Raab ◽

Xuehong Nöst ◽

Kitiya Rassamee ◽

...

Keyword(s):

2D Nmr ◽

Stem Bark ◽

No Production ◽

Hep G2 ◽

Pharmacological Studies ◽

Ic50 Values ◽

Hela S3 ◽

Anti Inflammatory ◽

First Time ◽

Mcf 7

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.

Download Full-text

Anti-Inflammatory Flavonolignans from Triticum aestivum Linn. Hull

Applied Sciences ◽

10.3390/app10238656 ◽

2020 ◽

Vol 10 (23) ◽

pp. 8656

Author(s):

Ah-Reum Han ◽

Yun-Seo Kil ◽

Min Jeong Hong ◽

Jisu Park ◽

Hyeon Hwa Park ◽

...

Keyword(s):

Triticum Aestivum ◽

Crop Production ◽

Ethyl Acetate Fraction ◽

Inhibitory Effect ◽

Raw 264.7 Cells ◽

No Production ◽

Phytochemical Investigation ◽

Ic50 Values ◽

Anti Inflammatory ◽

Food Grain

Wheat (Triticum aestivum Linn.; Poaceae) is a very common and important food grain and ranks second in total cereal crop production. A large amount of wheat hull is produced after threshing that, as the non-food part of wheat, is agro-waste, accounting for 15~20% of the wheat. This study aimed at biologically and phytochemically investigating wheat hull for its valorization as a by-product. In our ongoing search for natural product-derived anti-inflammatory agents, T. aestivum hull was evaluated for its nitric oxide (NO) production inhibition in lipopolysaccharide (LPS)-activated RAW 264.7 cells, and the phytochemical investigation of the ethyl acetate fraction showing inhibitory effect led to the isolation of a flavone (1) and seven flavonolignans (2–8). Compounds 2–8 have not yet been isolated from Triticum species. All compounds were evaluated for their LPS-induced NO production inhibition, and 1, 2, 4, 6, and 8 exhibited inhibitory effects with IC50 values ranging from 24.14 to 58.95 μM. These results suggest the potential of using T. aestivum hull as a source for producing anti-inflammatory components, enhancing its valorization as a by-product.

Download Full-text

Phytochemical Investigation and Anti-Inflammatory Activity of the Leaves of Machilus japonica var. kusanoi

Molecules ◽

10.3390/molecules25184149 ◽

2020 ◽

Vol 25 (18) ◽

pp. 4149

Author(s):

Shiou-Ling Li ◽

Ho-Cheng Wu ◽

Tsong-Long Hwang ◽

Chu-Hung Lin ◽

Shuen-Shin Yang ◽

...

Keyword(s):

Superoxide Anion ◽

2D Nmr ◽

Human Neutrophils ◽

Superoxide Anion Generation ◽

Phytochemical Investigation ◽

Potent Inhibition ◽

Bioassay Guided Fractionation ◽

Ic50 Values ◽

Anti Inflammatory ◽

New Compounds

In a series of anti-inflammatory screenings of lauraceous plants, the methanolic extract of the leaves of Machilus japonica var. kusanoi (Hayata) J.C. Liao showed potent inhibition on both superoxide anion generation and elastase release in human neutrophils. Bioassay-guided fractionation of the leaves of M. japonica var. kusanoi led to the isolation of twenty compounds, including six new butanolides, machinolides A–F (1–6), and fourteen known compounds (7–20). Their structures were characterized by 1D and 2D NMR, UV, IR, CD, and MS data. The absolute configuration of the new compounds were unambiguously confirmed by single-crystal X-ray diffraction analyses (1, 2, and 3) and Mosher’s method (4, 5, and 6). In addition, lignans, (+)-eudesmin (11), (+)-methylpiperitol (12), (+)-pinoresinol (13), and (+)-galbelgin (16) exhibited inhibitory effects on N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation in human neutrophils with IC50 values of 8.71 ± 0.74 μM, 2.23 ± 0.92 μM, 6.81 ± 1.07 μM, and 7.15 ± 2.26 μM, respectively. The results revealed the anti-inflammatory potentials of Formosan Machilus japonica var. kusanoi.

Download Full-text

Anti-Inflammatory Compounds from Vietnamese Piper bavinum

Journal of Chemistry ◽

10.1155/2020/1038636 ◽

2020 ◽

Vol 2020 ◽

pp. 1-7

Author(s):

Viet Dung Hoang ◽

Phi Hung Nguyen ◽

Minh Thu Doan ◽

Manh Hung Tran ◽

Nhu Tuan Huynh ◽

...

Keyword(s):

Raw 264.7 Cells ◽

No Production ◽

Dependent Manner ◽

Protein Levels ◽

Chemical Structures ◽

Anti Inflammatory ◽

First Time ◽

Dose Dependent ◽

Potent Inhibitory Activity

This study reports the anti-inflammatory activity-guided fractionation of the aerial part of Piper bavinum C. CD. (Piperaceae) that led to the isolation of eight secondary metabolites (1–8). The chemical structures of 1–8 were established mainly by NMR and mass spectra. Compound 5 was isolated from P. bavinum for the first time. All the isolated compounds were evaluated against LPS-induced NO production in macrophage RAW 264.7 cells in vitro. Among them, compound 4 showed the most potent inhibitory activity against the LPS-induced NO production with an IC50 value of 5.2 μM followed by compound 5 that inhibited NO production with an IC50 value of 13.5 μM. In the protein levels, compound 4 suppressed LPS-induced COX-2 and iNOS expressions in a dose-dependent manner. The results suggested that P. bavinum and its constituents might exert anti-inflammatory effects.

Download Full-text

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.

Download Full-text