Biotransformation of 4,5-O-dicaffeoylquinic acid methyl ester by human intestinal flora and evaluation on their inhibition of NO production and antioxidant activity of the products

2013 ◽  
Vol 55 ◽  
pp. 297-303 ◽  
Author(s):  
Xiu-Wei Yang ◽  
Nan Wang ◽  
Wei Li ◽  
Wei Xu ◽  
Shuai Wu
Keyword(s):  
Antioxidant Activity ◽  
Methyl Ester ◽  
Intestinal Flora ◽  
Acid Methyl Ester ◽  
No Production ◽  
Acid Methyl ◽  
Dicaffeoylquinic Acid

scholarly journals Azukisapogenol Triterpene Glycosides from Oxytropis chiliophylla Royle

Molecules ◽  
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.

scholarly journals Bioactive Variability and In Vitro and In Vivo Antioxidant Activity of Unprocessed and Processed Flour of Nine Cultivars of Australian lupin Species: A Comprehensive Substantiation

Antioxidants ◽  
2020 ◽  
Vol 9 (4) ◽  
pp. 282 ◽  
Author(s):  
Kishor Mazumder ◽  
Afia Nabila ◽  
Asma Aktar ◽  
Asgar Farahnaky
Keyword(s):  
Antioxidant Activity ◽  
Methyl Ester ◽  
Bioactive Compounds ◽  
Antioxidant Activities ◽  
Acid Methyl Ester ◽  
Heat Processing ◽  
Acid Methyl ◽  
Ms Analysis

The aim of this present investigation was to analyze bioactive compounds, as well as demonstrate the antioxidant activities of nine cultivars of Australian lupin species accompanied by observing the effect of domestic heat processing on their antioxidant activities adopting in vivo and in vitro approaches. Gas chromatography mass spectroscopy (GC-MS) analysis was performed for profiling bioactive compounds present in lupin cultivars. Multiple assay techniques involving quantification of polyphenolics, flavonoids and flavonol, electron transfer (ET) based assay, hydrogen atom transfer (HAT)-based assay and in vivo assays were performed. The major compounds found were hexadecanoic acid methyl ester, 9,12-octadecadienoic acid methyl ester, methyl stearate, lupanine,13-docosenamide and 11-octadecenoic acid (Z)- methyl ester. Mandelup was found to show excellent antioxidant activity. Moreover, Jurien, Gunyidi and Barlock had strong antioxidant activity. Both positive and negative impacts of heat processing were observed on antioxidant activity. Heating and usage of excess water during processing were the key determinants of loss of antioxidants. Negligible loss of antioxidant activity was observed in most of the assays whereas inhibition of both lipid peroxidation (33.53%) and hemolysis of erythrocytes (37.75%) were increased after processing. In addition, in vitro and in vivo antioxidant assays are found to show statistically significant (* p < 0.05 and ** p < 0.01) results, which are supported by the presence of a number of antioxidant compounds in GC-MS analysis.

scholarly journals Chemical Constituents of Pyrrosia calvata

2015 ◽  
Vol 10 (7) ◽  
pp. 1934578X1501000
Author(s):  
Yu-Jie Chen ◽  
Guo-Yong Xie ◽  
Guang-Kai Xu ◽  
Yi-Qun Dai ◽  
Lu Shi ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Chemical Constituents ◽  
Acid Methyl Ester ◽  
Caffeoylquinic Acid ◽  
Acid Methyl ◽  
Dicaffeoylquinic Acid ◽  
Whole Plant ◽  
The Family ◽  
First Time ◽  
Flavanone Glycoside

A novel flavanone glycoside, 3′,5′,5,7-tetrahydroxy-6- C- β-D-glucopyranosyl-flavanone (1), along with 16 known compounds, ( R/ S)-eriodictyol-8- C- β-D-glucopyranoside (2), quercetin-3- O- α-D-rhamnosyl (1′”→3′”)- β-D-glucopyranoside (3), hemipholin (4), 4 β-carboxymethyl-(-)-epicatechin methyl ester (5), kaempferol (6), quercetin (7), mangiferin (8), chlorogenic acid (9), 1,5- O-dicaffeoylquinic acid (10), 3,5- O-dicaffeoylquinic acid (11), 3- O-caffeoylquinic acid methyl ester (12), 1- O-caffeoyl glycoside (13), 4- O- β-D-glucopyranosyl-caffeic acid (14), 3′- O-methyleplcatechin-7- O- β-D-glucopyranoside (15), hop-22(29)-en-30-ol (16) and diploptene (17), were isolated from the whole plant of Pyrrosia calvata (Backer) Ching. Among them, compounds 2, 3, 4, 10, 11, 13 and 14 were isolated from the family Polypodiaceae for the first time, and compound 5 has not been recorded previously from the genus Pyrrosia.

scholarly journals Phytochemical analysis, cytotoxicity and antioxidant activity of cuckoo pint (Arum maculatum) leaf extract

2020 ◽  
Vol 63 (2) ◽  
pp. 119-124
Author(s):  
Hanady SA Al-Shmgani ◽  
Zahraa Hussein M Kadri ◽  
Mohammad MF Al-Halbosiy ◽  
Yaser Hassan Dewir
Keyword(s):  
Antioxidant Activity ◽  
Methyl Ester ◽  
Cell Line ◽  
Leaf Extract ◽  
Octadecenoic Acid ◽  
Acid Methyl Ester ◽  
Enzyme Linked Immunosorbent Assay ◽  
Phytochemical Analysis ◽  
Acid Methyl ◽  
Arum Maculatum

Arum maculatum is traditionally used for the control of many diseases and illnesses such as kidney pain, liver injury, hemorrhoids. However, the detailed biomedical knowledge about this species is still lacking. This study reports on the bioactive components and the possible mechanisms underlying the antioxidant, anti-inflammatory and cytotoxic activity of A. maculatum leaf extract. Gas chromatography-mass spectrometry (GC-MS) was used for phytochemical analysis. Assay of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide ) (MTT) was used to determine the cytotoxicity in the murine cell line L20B upon exposure to different extract concentrations for 24 h. Enzyme-linked immunosorbent assay (ELISA) was used to detect pro-inflammatory cytokines and tumor necrosis factor-α (TNF-α). GC-MS analysis identified the presence of important phytochemical components, e.g., 9-octadecenoic acid, methyl ester, (E), hexadecanoic acid, methyl ester, followed by benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester (17.74%), heptadecanoic acid, 16-methyl-, methyl ester and dibutyl phthalate. The results indicated a significant dose-dependent decrease in L20B cell growth at a dose of 400 μg/ml (IC50) that is associated with a significant 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity. The results suggested that the aqueous extract of A. maculatum leaves have potent antioxidant activity and cytotoxicity against L20B cell line with potential pro-inflammatory activity.

scholarly journals Transformation of Psoralen and Isopsoralen by Human Intestinal Microbial In Vitro, and the Biological Activities of Its Metabolites

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4080 ◽  
Author(s):  
Lu Liu ◽  
Lei Zhang ◽  
Ze-Xu Cui ◽  
Xiao-Yan Liu ◽  
Wei Xu ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Biological Activities ◽  
Intestinal Flora ◽  
Acid Methyl Ester ◽  
Intestinal Bacteria ◽  
Ultra Performance Liquid Chromatography ◽  
Acid Methyl ◽  
Wide Range ◽  
Dried Fruit

Psoralen (P) and isopsoralen (IP) are the main active ingredients in the dried fruit of Psoralen corylifolia L. (PC), with a wide range of pharmacology activities. The intestinal bacteria biotransformation plays a central role in the metabolism of the complex ingredients in traditional Chinese medicine (TCM). Our study aimed to investigated the metabolic profile of P and IP in the intestinal condition, co-cultured with human fecal bacteria anaerobically. Four bio-transforming products were obtained, including 6,7-furano-hydrocoumaric acid (P-1) and 6,7-furano-hydro- coumaric acid methyl ester (P-2), which transformed from P, and 5,6-furano-hydrocoumaric acid (IP-1) and 5,6-furano-hydrocoumaric acid methyl ester (IP-2), which were transformed from IP. It is worth mentioning that IP-2 is a new compound that has not been published. Their structures were analyzed based on their spectroscopic data. Moreover, a highly sensitive ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was used to characterize the metabolic pathways of P, IP, and their bio-transforming products in the reaction samples. In addition, the dampening effects against the oxidative stress of P, IP, and their bio-transforming products by human intestinal flora were estimated in vitro via the human colorectal cells (HCT116) and heterogeneous human epithelial colorectal adenocarcinoma cells (Caco-2) cell lines. The results showed that the metabolites have stronger activity than P and IP, which possibly provides a basis for elucidating the treating mechanisms of PC extract against inflammatory bowel disease.

scholarly journals Hypouricemic Effects of Acacetin and 4,5-O-Dicaffeoylquinic Acid Methyl Ester on Serum Uric Acid Levels in Potassium Oxonate-Pretreated Rats

2005 ◽  
Vol 28 (12) ◽  
pp. 2231-2234 ◽  
Author(s):  
Mai Thanh Thi Nguyen ◽  
Suresh Awale ◽  
Yasuhiro Tezuka ◽  
Liying Shi ◽  
Syed Faisal Haider Zaidi ◽  
...  
Keyword(s):  
Uric Acid ◽  
Methyl Ester ◽  
Serum Uric Acid ◽  
Acid Methyl Ester ◽  
Acid Methyl ◽  
Dicaffeoylquinic Acid ◽  
Potassium Oxonate

scholarly journals Anti-Inflammatory Effects of Fermented Bark of Acanthopanax sessiliflorus and Its Isolated Compounds on Lipopolysaccharide-Treated RAW 264.7 Macrophage Cells

2020 ◽  
Vol 2020 ◽  
pp. 1-10 ◽  
Author(s):  
Min Ji Kim ◽  
Hye Soo Wang ◽  
Min Won Lee
Keyword(s):  
Protocatechuic Acid ◽  
Acid Methyl Ester ◽  
No Production ◽  
Acid Methyl ◽  
Dicaffeoylquinic Acid ◽  
Raw 264.7 Macrophage Cells ◽  
Acanthopanax Sessiliflorus ◽  
Lignan Glycoside ◽  
Anti Inflammatory ◽  
Necrosis Factor

The fermentation was carried out on the bark of Acanthopanax sessiliflorus (AS). Acanthopanax species have been used in traditional medicine as tonics, sedatives, and antispasmodics. An activity-guided isolation of the fermented bark of A. sessiliflorus (FAS) yielded several phytochemicals: acanthoside D (1), acanthoside B (2), daucosterol (3), protocatechuic acid (4), chlorogenic acid methyl ester (5), ciwujiatone (6), syringaresinol (7), farnesol (8), 3,4-dicaffeoylquinic acid (9), and falcarindiol (10). HPLC analysis showed that content of lignan glycoside (1) was decreased and 4 and 7 were increased after fermentation. Anti-inflammatory activities on FAS showed the decrease of nitric oxide (NO) production, and inhibitory activities of iNOS and COX-2, proinflammatory cytokines (IL-6 and tumor necrosis factor-α), and collagenase. The aglycone, syringaresinol (7), which was increased through fermentation showed enhanced activity than 1. Thus, FAS may have the potential to treat inflammatory disorders, such as arthritis.

scholarly journals The Apoptosis-inducing Antiproliferative Activity and Quantitative Phytochemical Profiling of Polyphenol-rich Part of Leea Aequata L. Leaves

2021 ◽  
Author(s):  
Md. Golam Mostofa ◽  
A. S.M. Ali Reza ◽  
Zidan Khan ◽  
Toshifumi Tsukahara ◽  
AHM Khurshid Alam ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Free Radicals ◽  
Methyl Ester ◽  
Ethyl Acetate ◽  
Petroleum Ether ◽  
Methanolic Extract ◽  
Acid Methyl Ester ◽  
Chemical Compositions ◽  
Acid Methyl ◽  
Anti Cancer

Abstract Aim/Objectives: Oxidative stress (OS) caused by the accumulation of free radicals in the body triggers many life-threatening diseases, including cancer. Plants are the rich source of safe and effective medicinal compounds like antioxidants that can prevent OS by scavenging free radicals. The aim of this study was to explore the chemical compositions of the methanolic extract of Leea aequata L. leaves possessed the highest antioxidant and cytotoxic activities.Methods and Materials: The Leea aequata leaves (LAL) was extracted with 80% methanol and the crude methanolic extract of LAL (CME) was successively fractionated with petroleum ether, chloroform, ethyl acetate and finally with water to get petroleum ether (PEF), chloroform (CHF), ethyl acetate (EAF) and aqueous (AQF) fraction, respectively. The antioxidant activity was evaluated by the in vitro standard spectrophotometric methods. The MTT colorimetric method was used to measure cytotoxic activity. Apoptosis was measured using fluorescein annexin V-FITC/PI staining method. GC-MS was used to investigate phytochemical compositions.Results: Among the fractions, the highest phenolic and flavonoid-rich fraction was EAF, which contained 267.05± 8.53 mg of gallic acid equivalent (GAE) and 152.98±1.96 mg of catechin equivalent (CAE)/gm of dried extract, respectively. The EAF was found to be the highest antioxidant and reducing power activities. Also, EAF had the strongest free radical scavenging activity with IC50 values of 5.11, 36.54 and 38.96 µg/mL for DPPH, hydroxyl and lipid peroxide free radicals, respectively. Moreover, EAF significantly reduced the HeLa cell proliferation and it was due to the induction of apoptosis of HeLa cells. Furthermore, GC-MS data revealed that EAF contained 17 compounds. Methyl esters of long chain fatty acid were the major chemical constituents. Interestingly, hexadecanoic acid, methyl ester; 9-octadecenoic acid (Z)-, methyl ester; 9,12-octadecadienoic acid, methyl ester (Z, Z) and phenol, 2,4-bis(1,1-dimethylethyl) are known to be antioxidant and cytotoxic. Antioxidant and anti-cancer activity were significantly correlated with the total content of phenolics and flavonoids, suggest that the fractions could be the good source of antioxidant and anti-cancer agents.Conclusion: The EAF of Leea aequata has strong polyphenolic content compared to the other fractions. The cytotoxic and antioxidant activity of Leea aequata were due to the presence of different bioactive compounds.

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