scholarly journals Bioactive Flavonoid Glycosides and HPLC and UPLC Quantification of Commercial Astragali Complanati Semen

Molecules ◽  
2020 ◽  
Vol 25 (20) ◽  
pp. 4762
Author(s):  
Jenny Chun-Ling Kuo ◽  
Li-Jie Zhang ◽  
Hung-Tse Huang ◽  
Chia-Ching Liaw ◽  
Zhi-Hu Lin ◽  
...  
Keyword(s):  
Ethanol Extract ◽  
2D Nmr ◽  
Biological Evaluation ◽  
Uv Spectra ◽  
Flavonoid Glycosides ◽  
No Production ◽  
Chemical Structures ◽  
Isoflavone Glycoside ◽  
Two Samples ◽  
Hplc Profiles

Eleven compounds, including nine known flavonoid glycosides (1–4, 6–8, and 10–11), one isoflavone glycoside (5), and a glansreginic acid (9), were isolated from the 80% ethanol extract of commercial Astragali Complanati Semen (ACS). All chemical structures were determined by spectroscopic analyses, including 1D and 2D NMR. Compounds 2, 4, 5, 6, 9, and 10 were isolated and identified from the title plant for the first time. Biological evaluation revealed that all the isolates showed promising anti-NO production, and 1, 2, 3, and 8 were more potent in antioxidant activity than vitamin E. The major peaks in the UPLC and HPLC profiles identified their chemical structures by comparing their retention time and UV spectra with those of the reference substances. Furthermore, nine of the eleven samples collected from North, Middle, and South regions of Taiwan possessed similar HPLC fingerprints and were identified as Astragali Complanati Semen, whereas the other two samples from southern Taiwan would be the adulterants due to the different fingerprinting patterns. In addition, an HPLC-UV method was employed to determine the content of target compound complanatuside (11) with good linear regression (R2 = 0.9998) for ACS in the Taiwanese market. Of the isolates, flavonol glycosides 1 and 3 were the major peaks in HPLC/UPLC, and showed more potent antioxidant and anti-NO production activities than that of 11, revealing that these compounds can be the available agents for the quality control of ACS.

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.

scholarly journals New Acetylated Terpenoids from Sponge Rhabdastrella providentiae Inhibit NO Production in LPS Stimulated BV2 Cells

2018 ◽  
Vol 13 (6) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Duong Thi Dung ◽  
Pham Hai Yen ◽  
Nguyen Xuan Nhiem ◽  
Tran Hong Quang ◽  
Bui Huu Tai ◽  
...  
Keyword(s):  
2D Nmr ◽  
No Production ◽  
Esi Ms ◽  
Chemical Structures ◽  
Bv2 Cells

Three new acetylated terpenoids, rhabdaprovidines A-C (1-3), were isolated from the Vietnamese sponge Rhabdastrella providentiae. Their chemical structures were established by HR-ESI-MS, 1D and 2D-NMR experiments. These compounds share 6,6,5-tricyclic nucleus of isomalabaricane-type triterpene, the specific secondary constituents from Rhabdastrella species. Compounds 1-3 inhibited NO production in LPS stimulated BV2 cells with IC50 values of 20.4 ± 1.5, 17.5 ± 0.9, and 46.8 ± 2.3 μM, respectively.

scholarly journals Charantoside L, A New Cucurbitane-Type Glycoside from Momordica charantia L. with α-Glucosidase Inhibitory Activities

2022 ◽  
Vol 17 (1) ◽  
pp. 1934578X2110689
Author(s):  
Duong Thi Hai Yen ◽  
Pham Hai Yen ◽  
Nguyen Quang Hop ◽  
Nguyen Anh Hung ◽  
Ha Thi Thu Tran ◽  
...  
Keyword(s):  
Ethanol Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Momordica Charantia ◽  
Spectroscopic Methods ◽  
Inhibitory Effects ◽  
Chemical Structures ◽  
Glucosidase Activity ◽  
Inhibitory Activities ◽  
Reported Data

A new cucurbitane-type glycoside (1) and two known compounds (2-3) were isolated from the ethanol extract of the fruits of Momordica charantia L. Their chemical structures were determined as (19 S,23 E)-5 β­,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol 3 -O-β-D-allopyranoside (1), goyaglycoside d (2), and (19 S,23 E)-5 β,19-epoxy-19-methoxycucurbita-6,23-diene-3 β,25-diol (3) on the basis of the extensive spectroscopic methods, including 1D, 2D NMR, HRESIMS, and in comparison with the reported data. Compounds 1 to 3 were evaluated for α-glucosidase inhibitory effects. Compounds 1 and 2 showed anti α-glucosidase activity with IC50 values of 134.12 ± 11.20 and 163.17 ± 13.71 µM, respectively, compared with the positive control, acarbose, IC50 160.99 ± 14.30 μM. Compounds 2 and 3 were first isolated from plant M. charantia growing in Vietnam.

scholarly journals FLAVONOIDS AND TRITERPENOIDS FROM CALLISTEMON CITRINUS AND THEIR INHIBITORY EFFECT ON NO PRODUCTION IN LPS-STIMULATED RAW264.7 MACROPHAGES

2016 ◽  
Vol 54 (2) ◽  
pp. 214 ◽  
Author(s):  
Nguyen Manh Cuong ◽  
Pham Ngoc Khanh ◽  
Ho Viet Duc ◽  
Tran Thu Huong ◽  
Youn-Chui Kim ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Raw264.7 Cells ◽  
No Production ◽  
Inhibition Activity ◽  
Chemical Structures ◽  
Raw264.7 Macrophages ◽  
Phytochemical Investigation ◽  
Methoxy Flavone

Phytochemical investigation of the leaves and stems of Callistemon citrinus (Curtis) Skeels led to the isolation of 12 flavonoid and triterpenoid compounds,  including one new flavonoid, callistine A (1) and six known flavonoids 6,7- dimethyl-5,7-dihydroxy-4’-methoxy flavone (2), astragalin (3), quercetin (4), catechin (5), eucalyptin (6), and 8-demethyleucalyptin (7), along with 5 triterpenoids, 3-β-acetylmorolic acid (8), 3β-hydroxy-urs-11-en-13(28)-olide (9), betulinic acid (10), diospyrolide (11) and ursolic acid (12). Their chemical structures were determined from the spectroscopic evidences counting 1D- and 2D-NMR and HR-MS data. All the isolated compounds were examined for their anti-inflammatory activity against LPS-activated NO production in macrophage RAW264.7 cells. Among them, quercetin (4) and 3β-hydroxy-urs-11-en-13(28)-olide (9) showed potential inhibition activity in nitric oxide (NO)  production in RAW264.7 cells exposed to LPS.

Antidiabetic and Anticholinesterase Properties of Extracts and Pure Metabolites of Fruit Stems of Pistachio (Pistacia vera L.)

2020 ◽  
Vol 24 (7) ◽  
pp. 785-797
Author(s):  
Yabo Dambagi Lawali ◽  
Akyuz Mehmet ◽  
Aydin Tuba ◽  
Cakir Ahmet
Keyword(s):  
Shikimic Acid ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Chemical Structures ◽  
Ic50 Values ◽  
Ft Ir ◽  
High Concentrations ◽  
Ethanol Extracts ◽  
Anticholinesterase Properties

: Five metabolites were isolated by chromatographic methods from the fruit stems of P. vera and their chemical structures were characterized as masticadienonic acid (1), tirucallol (2), masticadienolic acid (3), pistachionic acid (4) and inulobiose (5) via FT-IR, 1H-NMR, 13C-NMR, 1D-NMR and 2D-NMR. Pistachionic acid (4), a new shikimic acid derivative, was isolated from the ethanol extract for the first time. The hexane, chloroform, ethanol extracts and pure metabolites exhibited antidiabetic properties by inhibiting α- glycosidase and α-amylase enzymes at different rates. Their inhibitory effects against the α- glycosidase enzyme were also higher than that of the acarbose (IC50=10.30 mg/mL). Masticadienolic acid (3) (IC50=0.03 mg/mL), masticadienonic acid (1) (IC50=0.13 mg/mL) and hexane extract (IC50=0.09 mg/mL) with the lowest IC50 values were found to be most active substances. Nevertheless, the inhibitory effect of acarbose against the α-amylase enzyme was determined to be higher than the inhibition effects of the extracts and pure metabolites. According to the IC50 values, the best inhibitors against the α-amylase were ethanol extract (IC50=5.17 mg/mL), pistachionic acid (4) (IC50=7.35 mg/mL), tirucallol (2) (IC50=7.58 mg/mL) and masticadienolic acid (3) (IC50=8.22 mg/mL), respectively among the applications. In addition, anticholinesterase properties of the extracts and pure metabolites were investigated by testing the inhibitory properties against acetylcholine esterase (AChE) and butrylcholine esterase (BChE) enzymes activities. The results showed that the anticholinesterase properties of all extracts and pure metabolites were weaker than those of the commercial cholinesterase inhibitors, neostigmine and galantamine, and all applications reduced the activity of these enzymes at very high concentrations.

scholarly journals TWO NOVEL FLAVONE C-GLYCOSIDES ISOLATED FROM AFROCARPUS GRACILIOR: POM ANALYSES AND IN VITRO CYTOTOXIC ACTIVITY AGANIST HEPATOCELLULAR CARCINOMA

2019 ◽  
pp. 57-62 ◽  
Author(s):  
Amel M. Kamal ◽  
Mohamed Abdelhady ◽  
Taibi Ben Hadda
Keyword(s):  
Hepatocellular Carcinoma ◽  
Cytotoxic Activity ◽  
Anticancer Agents ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Ionization Mass ◽  
Hep G2 ◽  
Chemical Structures ◽  
Pom Analyses

Objective: Cancer is considered as one of the top reasons of death and the number of cases increasing gradually. Cancer is severe clinical difficulty to the health caution system. This study explored two novel polyphenols of Afrocarpus gracilior Pilger growing in Egypt and evaluated their cytotoxic activity. Methods: Methanolic (80%) extract of the leaves of A. gracilior was subjected to column chromatography; the chemical structures of the isolated compounds were established by advanced spectral techniques: UV, 1H, 13C NMR, two dimensional NMR (2D NMR) and electron spray ionization mass spectroscopy (ESI-MS). Compounds 1 and 2 were studied for their cytotoxic activity against hepatocellular carcinoma (Hep-G2) using sulforhodamine B (SRB) assay. Furthermore the pharmacokinetics profiles of these molecules were accessed by employing Petra/Osiris/Molinspiration (POM) analyses. Results: Two novel C-flavonoid glycosides were isolated [1: Apigenin 8-C-β-D-glucopyranosyl-(1```→4``)-O-β-D-glucopyranoside] and [2: 7-O methyl-luteolin 8-C-β-glucopyranosyl-(1```→4``)-O-β-D-glucopyranoside]. They exhibited significant cytotoxic activity (IC50 = 9.02 and 15.61 µg/ml, respectively) against Hep-G2 cells. The POM analyses revealed that the activity of these two compounds depends on the presence of glucosyl and alkyl groups at the internal and terminal atmosphere of the compounds. Conclusion: These findings demonstrated that the leaves of A. gracilior contain a series of bioactive polyphenolic compounds with significant cytotoxic properties against hepatocellular carcinoma and may be used as alternative anticancer agents for doxorubicin. On the basis of POM calculations, it will be interesting to develop some alternative flavones because the deglucosylated derivatives have a better drug score than parent molecules. This preliminary study will be extended to other strains of cancer.

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

Molecules ◽  
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).

scholarly journals Glycosylated Coumarins, Flavonoids, Lignans and Phenylpropanoids from Wikstroemia nutans and Their Biological Activities

2021 ◽  
Author(s):  
Meifang Wu ◽  
Xiangdong Su ◽  
Yichuang Wu ◽  
Yuanjing Luo ◽  
Ying Guo ◽  
...  
Keyword(s):  
Biological Activities ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
No Production ◽  
Inhibitory Effects ◽  
Traditional Herbal Medicine ◽  
First Time ◽  
Raw264.7 Macrophage ◽  
Structure Diversity

Wikstroemia nutans Champ. ex Benth., a traditional herbal medicine collected at the Lingnan region of China, was chemically investigated. A new bis-coumarin glucoside, wikstronutin (1), along with three known bis- and tri-coumarin glucosides (2–4), two flavonoid glycosides (5–6), and eleven lignan glucosides (7–17) were isolated from the stems and roots of W. nutans. The new structure including its absolute configuration was elucidated based on a combination of 1D- and 2D-NMR, UV, IR, HRESIMS spectroscopic data, as well as chemical transformation. Compounds (1–17) were first isolated from the plant species W. nutans, while compounds 1–3, 8, and 11 was reported from the genus Wikstroemia for the first time. All co-isolates were evaluated for their in vitro inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine RAW264.7 macrophage cells. The antibacterial activity of the selected compounds was also tested. Our work enriches the structure diversity of the secondary metabolites from the genus Wikstroemia.

scholarly journals Antiviral Activities of Compounds Isolated from Pinus densiflora (Pine Tree) against the Influenza A Virus

Biomolecules ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 711
Author(s):  
Thi Kim Quy Ha ◽  
Ba Wool Lee ◽  
Ngoc Hieu Nguyen ◽  
Hyo Moon Cho ◽  
Thamizhiniyan Venkatesan ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Influenza A ◽  
Pinus Densiflora ◽  
2D Nmr ◽  
Surface Proteins ◽  
No Production ◽  
Dependent Manner ◽  
Viral Mrna ◽  
Chemical Structures ◽  
Pine Tree

Pinus densiflora was screened in an ongoing project to discover anti-influenza candidates from natural products. An extensive phytochemical investigation provided 26 compounds, including two new megastigmane glycosides (1 and 2), 21 diterpenoids (3–23), and three flavonoids (24–26). The chemical structures were elucidated by a series of chemical reactions, including modified Mosher’s analysis and various spectroscopic measurements such as LC/MS and 1D- and 2D-NMR. The anti-influenza A activities of all isolates were screened by cytopathic effect (CPE) inhibition assays and neuraminidase (NA) inhibition assays. Ten candidates were selected, and detailed mechanistic studies were performed by various assays, such as Western blot, immunofluorescence, real-time PCR and flow cytometry. Compound 5 exerted its antiviral activity not by direct neutralizing virion surface proteins, such as HA, but by inhibiting the expression of viral mRNA. In contrast, compound 24 showed NA inhibitory activity in a noncompetitive manner with little effect on viral mRNA expression. Interestingly, both compounds 5 and 24 were shown to inhibit nitric oxide (NO) production and inducible nitric oxide synthase (iNOS) expression in a dose-dependent manner. Taken together, these results provide not only the chemical profiling of P. densiflora but also anti-influenza A candidates.

Hybridized Quinoline Derivatives as Anticancer Agents: Design, Synthesis, Biological Evaluation and Molecular Docking

2019 ◽  
Vol 19 (4) ◽  
pp. 439-452 ◽  
Author(s):  
Mohamed R. Selim ◽  
Medhat A. Zahran ◽  
Amany Belal ◽  
Moustafa S. Abusaif ◽  
Said A. Shedid ◽  
...  
Keyword(s):  
Cell Cycle ◽  
Anticancer Agents ◽  
Caspase 3 ◽  
Biological Evaluation ◽  
Tubulin Polymerization ◽  
Design Synthesis ◽  
Chemical Structures ◽  
M Phase ◽  
Induced Apoptosis ◽  
Derivatives Of

Objective: Conjugating quinolones with different bioactive pharmacophores to obtain potent anticancer active agents. Methods: Fused pyrazolopyrimidoquinolines 3a-d, Schiff bases 5, 6a-e, two hybridized systems: pyrazolochromenquinoline 7 and pyrazolothiazolidinquinoline 8, different substituted thiazoloquinolines 13-15 and thiazolo[3,2-a]pyridine derivatives 16a-c were synthesized. Their chemical structures were characterized through spectral and elemental analysis, cytotoxic activity on five cancer cell lines, caspase-3 activation, tubulin polymerization inhibition and cell cycle analysis were evaluated. Results: Four compounds 3b, 3d, 8 and 13 showed potent activity than doxorubicin on HCT116 and three compounds 3b, 3d and 8 on HEPG2. These promising derivatives showed increase in the level of caspase-3. The trifloromethylphenyl derivatives of pyrazolopyrimidoquinolines 3b and 3d showed considerable tubulin polymerization inhibitory activity. Both compounds arrested cell cycle at G2/M phase and induced apoptosis. Conclusion: Compounds 3b and 3d can be considered as promising anticancer active agents with 70% of colchicine activity on tubulin polymerization inhibition and represent hopeful leads that deserve further investigation and optimization.

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