scholarly journals Lignans from the Twigs of Litsea cubeba and Their Bioactivities

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 306 ◽  
Author(s):  
Xiuting Li ◽  
Huan Xia ◽  
Lingyan Wang ◽  
Guiyang Xia ◽  
Yuhong Qu ◽  
...  
Keyword(s):  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Specific Rotation ◽  
No Production ◽  
Etoh Extract ◽  
Litsea Cubeba ◽  
Raw264.7 Macrophages ◽  
A2780 Cell ◽  
Ic50 Values ◽  
Relationship Importance

Litsea cubeba, an important medicinal plant, is widely used as a traditional Chinese medicine and spice. Using cytotoxicity-guided fractionation, nine new lignans 1–9 and ten known analogues 10–19 were obtained from the EtOH extract of the twigs of L. cubeba. Their structures were assigned by extensive 1D- and 2D-NMR experiments, and the absolute configurations were resolved by specific rotation and a combination of experimental and theoretically calculated electronic circular dichroism (ECD) spectra. In the cytotoxicity assay, 7′,9-epoxylignans with feruloyl or cinnamoyl groups (compounds 7–9, 13 and 14) were selectively cytotoxic against NCI-H1650 cell line, while the dibenzylbutyrolactone lignans 17–19 exerted cytotoxicities against HCT-116 and A2780 cell lines. The results highlighted the structure-activity relationship importance of a feruloyl or a cinnamoyl moiety at C-9′ or/and C-7 ketone in 7′,9-epoxylignans. Furthermore, compound 11 was moderate active toward protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 13.5 μM, and compounds 4–6, 11 and 12 displayed inhibitory activity against LPS-induced NO production in RAW264.7 macrophages, with IC50 values of 46.8, 50.1, 58.6, 47.5, and 66.5 μM, respectively.

scholarly journals Lignans from the Twigs of Litsea cubeba and Their Bioactivities

2018 ◽  
Author(s):  
Xiuting Li ◽  
Huan Xia ◽  
Lingyan Wang ◽  
Guiyang Xia ◽  
Yuhong Qu ◽  
...  
Keyword(s):  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Specific Rotation ◽  
No Production ◽  
Etoh Extract ◽  
Litsea Cubeba ◽  
Raw264.7 Macrophages ◽  
A2780 Cell ◽  
Ic50 Values ◽  
Relationship Importance

Litsea cubeba, an important medicinal plant, is widely used as traditional Chinese medicine and spice. Using cytotoxicity-guided fractionation, nine new lignans (1-9) and eleven known analogues (10-19) were obtained from the EtOH extract of the twigs of L. cubeba. Their structures were assigned by extensive 1D and 2D NMR experiments, and the absolute configurations were resolved by specific rotation and a combination of experimental and theoretically calculated electronic circular dichroism (ECD) spectra. In the cytotoxicity assay, 7',9-epoxylignans with feruloyl or cinnamoyl group (7-9, 13 and 14) were selectively cytotoxic against NCI-H1650 cell line, while the dibenzylbutyrolactone lignans (17-19) exerted cytotoxicities against HCT-116 and A2780 cell lines. The results highlighted the structure-activity relationship importance of a feruloyl or a cinnamoyl moiety at C-9′ or/and C-7 ketone in 7',9-epoxylignans. Furthermore, compound 11 was moderate active toward protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 13.5 μM, and compounds 4-6, 11 and 12 displayed inhibitions against LPS-induced NO production in RAW264.7 macrophages, with IC50 values of 46.8, 50.1, 58.6, 47.5, and 66.5 μM, respectively.

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

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2577 ◽  
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.

scholarly journals A New Pentacyclic Triterpene fromHumata tyermanniMoore with the Inhibitory Activities against LPS-Induced NO Production in RAW264.7 Macrophages

2013 ◽  
Vol 2013 ◽  
pp. 1-4
Author(s):  
Lei Zhang ◽  
Feng Wang ◽  
Zhen-You Jiang ◽  
Yao-Kui Zhu ◽  
Ying-Zhou Cen
Keyword(s):  
Nitric Oxide ◽  
Spectral Analysis ◽  
2D Nmr ◽  
No Production ◽  
Pentacyclic Triterpene ◽  
Raw264.7 Macrophages ◽  
Inhibitory Activities

One new pentacyclic triterpene, hopane-22 (29)-en-24ol(2), with five known hopane-type pentacyclic triterpene compounds: hop-22(29)-ene(1), adiantone(3), 22-hydroxyhopane(4), 6α, 22-dihydroxyhopane(5), and 17(21)-hopene(6)were isolated fromHumata tyermanniMoore. The structure of compound2was elucidated on the basis of its 1D and 2D NMR spectral analysis. All these compounds were evaluated for their inhibitory activities of LPS-induced nitric oxide (NO) production in RAW264.7 macrophages.

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

Molecules ◽  
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.

scholarly journals Structure Revision and Protein Tyrosine Phosphatase Inhibitory Activity of Drazepinone

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 714
Author(s):  
Fei Cao ◽  
Li Pan ◽  
Wen-Bin Gao ◽  
Yun-Feng Liu ◽  
Cai-Juan Zheng ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Chemical Shifts ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Nmr Data ◽  
Structure Revision ◽  
Ic50 Values

From the marine-derived fungus Penicillium sumatrense (Trichocomaceae), a pair of enantiomers [(+)-1 and (−)-1] were isolated with identical 1D NMR data to drazepinone, which was originally reported to have a trisubstituted naphthofuroazepinone skeleton. In this study, we confirmed the structures of the two enantiomers as drazepinone and revised their structures by detailed analysis of extensive 2D NMR data and a comparison of the calculated 13C chemical shifts, ECD, VCD, and ORD spectra with those of the experiment ones. (+)-1 and (−)-1 were evaluated for their PTP inhibitory activity in vitro. (−)-1 showed selective PTP inhibitory activity against PTP1B and TCPTP with IC50 values of 1.56 and 12.5 μg/mL, respectively.

scholarly journals Four New Iridoid Metabolites Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Anti-Inflammatory Activities on LPS-Induced RAW264.7 Cells

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4271
Author(s):  
Fang-Pin Chang ◽  
Shyh-Shyun Huang ◽  
Tzong-Huei Lee ◽  
Chi-I Chang ◽  
Tzong-Fu Kuo ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Detailed Analysis ◽  
Cell Line ◽  
Spectroscopic Data ◽  
Protocatechuic Acid ◽  
Control Group ◽  
No Production ◽  
Raw264.7 Macrophages ◽  
Ic50 Values ◽  
Inhibitory Activities

One new iridoid, namely neonanin C (1) one monocyclic iridoid ring-opened derivative namely neonanin D (2), two new bis-iridoid derivatives namely reticunin A (3) and reticunin B (4) with sixteen known compounds (5–20) were isolated from the stems of Neonauclea reticulata (Havil.) Merr. These new structures were determined by the detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1–20 were evaluated for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages cell line. The results showed that all compounds exhibited no obvious cytotoxicity compared to the control group and five compounds including isoboonein (7), syringaresinol (10), (+)-medioresinol (12), protocatechuic acid (14) and trans-caffeic acid (15) exhibited inhibitory activities with IC50 values at 86.27 ± 3.45; 9.18 ± 1.90; 76.18 ± 2.42; 72.91 ± 4.97 and 95.16 ± 1.20 µg/mL, respectively.

scholarly journals A New Megastigmane Glucoside and Other Constituents from Desmodium gangeticum

2020 ◽  
Vol 2020 ◽  
pp. 1-4
Author(s):  
Hau Viet Dang ◽  
Giang Hoang Do ◽  
Phuong Thi Ngo ◽  
Tien Dat Nguyen ◽  
Ha Minh Le
Keyword(s):  
Nmr Spectra ◽  
Aerial Part ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Methyl Benzoate ◽  
Raw264.7 Cells ◽  
No Production ◽  
2D Nmr Spectra ◽  
Ic50 Values ◽  
Megastigmane Glucoside

A new megastigmane glycoside, gangeticoside (1), and three known compounds leonuriside A (2), methyl benzoate 2-O-β-D-glucopyranoside (3), and tortoside A (4) were isolated from the aerial part of Desmodium gangeticum. Their structures were determined by 1D and 2D NMR spectra. The isolated compounds were evaluated for their inhibitory effect on NO production in LPS-stimulated RAW264.7 cells. Among them, compounds 1, 2, and 3 exhibited strong effect with the IC50 values of 22.3, 15.6, 7.3 μM, respectively.

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 ◽  
...  
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.

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

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
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.

scholarly journals A New Phenylpropanoid from the Roots of Solanum melongena L. and Evaluation of Anti-inflammatory Activity

2021 ◽  
Vol 15 (4) ◽  
pp. 261-266
Author(s):  
Yan Liu ◽  
Xin Yin ◽  
Yanping Sun ◽  
Yuan Liu ◽  
Dongxv Lu ◽  
...  
Keyword(s):  
Solanum Melongena ◽  
Ethanol Extract ◽  
2D Nmr ◽  
No Production ◽  
Raw 264.7 ◽  
Chemical Structures ◽  
Raw 264.7 Cell ◽  
Ic50 Values ◽  
Inhibitory Activities ◽  
Raw 264.7 Cell Line

Fifteen phenylpropanoids were isolated from the ethanol extract of the roots of Solanum melongena L., including a new compound, melongenapanoid A (1), together with fourteen known compounds (2-15). Their chemical structures were elucidated by 1D and 2D NMR and HR-MS data according to those values of the literatures. The fourteen known compounds (2-15) were all firstly isolated from this plant. While, the isolates were evaluated for the inhibitory activities on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in RAW 264.7 cell line. Compounds 2, 4 and 5 showed moderate inhibition of NO production with IC50 values of 28.7, 24.4 and 32.6 μM, respectively.

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