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

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5765
Author(s):  
Yung-Shun Su ◽  
Ming-Der Wu ◽  
Jih-Jung Chen ◽  
Ming-Jen Cheng ◽  
Yueh-Hsiung Kuo ◽  
...  

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.

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3336 ◽  
Author(s):  
Ping-Chen Tu ◽  
Han-Chun Tseng ◽  
Yu-Chia Liang ◽  
Guan-Jhong Huang ◽  
Te-Ling Lu ◽  
...  

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.


Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4909
Author(s):  
Yung-Shun Su ◽  
Jih-Jung Chen ◽  
Ming-Jen Cheng ◽  
Chee-Yin Chai ◽  
Aij-Lie Kwan ◽  
...  

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.


Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4149
Author(s):  
Shiou-Ling Li ◽  
Ho-Cheng Wu ◽  
Tsong-Long Hwang ◽  
Chu-Hung Lin ◽  
Shuen-Shin Yang ◽  
...  

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.


Marine Drugs ◽  
2022 ◽  
Vol 20 (1) ◽  
pp. 44
Author(s):  
Hee Jae Shin ◽  
Chang-Su Heo ◽  
Cao Van Anh ◽  
Yeo Dae Yoon ◽  
Jong Soon Kang

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.


Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 1923 ◽  
Author(s):  
Liyao Wang ◽  
Kaixue Zhang ◽  
Shu Han ◽  
Liu Zhang ◽  
Haiying Bai ◽  
...  

Licorice, the root and rhizome of Glycyrrhiza uralansis Fisch, is one of the most frequently used Traditional Chinese Medicines in rigorous clinical trials to remove toxins and sputum, and to relieve coughing. However, the aerial parts are not used so widely at present. It has been reported that the aerial parts have many bioactivities such as anti-microbial and anti-HIV activities. In this study, we aimed to discover the bioactive compounds from the leaves of G. uralensis. Four new compounds, licostilbene A-B (1–2) and licofuranol A-B (3–4), together with eight known flavonoids (5–12), were isolated and identified from the leaves of G. uralensis. Their structures were elucidated mainly by the interpretation of high-resolution electrospray mass spectrometry (HR-ESI-MS) and nuclear magnetic resonance (NMR) spectroscopic data. Compared with quercetin, which showed a 50% inhibitory concentration (IC50) value of 4.08 μg/mL, compounds 1–9 showed significant anti-inflammatory activities by inhibiting lipopolysaccharide (LPS)-induced nitric oxide (NO) production with IC50 values of 2.60, 2.15, 3.21, 3.25, 2.00, 3.45, 2.53, 3.13 and 3.17 μg/mL, respectively. The discovery of these active compounds is important for the prevention and treatment of inflammation.


2021 ◽  
Vol 7 (6) ◽  
pp. 408
Author(s):  
Virayu Suthiphasilp ◽  
Achara Raksat ◽  
Tharakorn Maneerat ◽  
Sarinya Hadsadee ◽  
Siriporn Jungsuttiwong ◽  
...  

Chemical investigation of the mycelia of the pathogenic fungus Curvularia sp. which was isolated from a leaf of Dactyloctenium aegyptium (crowfoot grass), resulted in the isolation of a new compound, curvulariahawadride (5), along with five known compounds (1–4, and 6). Their structures were determined on the basis of spectroscopic data, including 1D and 2D NMR and HRESIMS. The absolute configuration of 5 was established from experimental and calculated electronic circular dichroism (ECD). Compounds 1, 3, and 5 showed nitric oxide (NO) production inhibitory activity with IC50 values of 53.7, 32.8, and 12.8 µM, respectively. Compounds 2 and 4 showed significant cytotoxicity against lung cancer A549, colorectal cancer SW480, and leukemic K562 cells with an IC50 ranging value of 11.73 to 17.59 µM.


Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 470 ◽  
Author(s):  
Longfang Guo ◽  
Jie Lin ◽  
Shubin Niu ◽  
Shuchun Liu ◽  
Ling Liu

Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3), 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (4), isosulochrin (5), chloroisosulochrin (6), and pestalotether D (9), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). The structures of the new compounds were unambiguously deduced by HRESIMS and 1D/2D-NMR spectroscopic data. Compound 6 showed modest cytotoxicity against the HeLa cell line with an IC50 value of 35.2 μM. Compound 9 also showed cytotoxic to the HeLa and MCF-7 cell lines, with IC50 values of 60.8 and 22.6 μM, respectively. Additionally, compounds 1 and 2 exhibited antioxidant activity in scavenging DPPH radical with IC50 values of 54.2 and 59.2 μg/mL, respectively.


2018 ◽  
Vol 17 (3) ◽  
pp. 134-139
Author(s):  
R.M. Perez-Gutierrez

Methanol extract from Lippia graveolens (Mexican oregano) was studied in order to identify inhibitory bioactives for protein tyrosine phosphatase 1B (PTP1B). Known flavone as lutein (1), and another flavone glycoside such as lutein-7-o-glucoside (2), 6-hydroxy-lutein-7-ohexoside (3) and lutein-7-o-ramnoide (4) were isolated from methanol extract of aerial parts of the Lippia graveolens. All isolates were identified based on extensive spectroscopic data analysis, including UV, IR, NMR, MS and compared with spectroscopic data previously reported. These flavones were evaluated for PTP1B inhibitory activity. Among them, compounds 1 and 3 displayed potential inhibitory activity against PTP1B with IC50 values of 7.01 ± 1.25 μg/ml and 18.4 μg/ml, respectively. In addition, compound 2 and 4 showed moderate inhibitory activity with an IC50 value of 23.8 ± 6.21 and 67.8 ± 5.80 μg/ml respectively. Among the four compounds, luteolin was found to be the most potent PTP1B inhibitor compared to the positive control ursolic acid, with an IC50 value of 8.12 ± 1.06 μg/ml. These results indicate that flavonoids constituents contained in Lippia graveolens can be considered as a natural source for the treatment of type 2 diabetes.


Marine Drugs ◽  
2021 ◽  
Vol 19 (6) ◽  
pp. 305
Author(s):  
Guangyuan Luo ◽  
Li Zheng ◽  
Qilin Wu ◽  
Senhua Chen ◽  
Jing Li ◽  
...  

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.


Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1561 ◽  
Author(s):  
Qiao ◽  
Khutsishvili ◽  
Alizade ◽  
Atha ◽  
Borris

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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