Ellagitannin Chemistry. Syntheses of Tellimagrandin II and a Dehydrodigalloyl Ether-Containing Dimeric Gallotannin Analogue of Coriariin A

1999 ◽  
Vol 64 (1) ◽  
pp. 209-216 ◽  
Author(s):  
Ken S. Feldman ◽  
Kiran Sahasrabudhe
Keyword(s):  
Tellimagrandin Ii

scholarly journals Hydrolysable Tannins Exhibit Acetylcholinesterase Inhibitory and Anti-Glycation Activities In Vitro and Learning and Memory Function Improvements in Scopolamine-Induced Amnesiac Mice

Biomedicines ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 1066
Author(s):  
Lih-Geeng Chen ◽  
Shyr-Yi Lin ◽  
Yi-Shan Lee ◽  
Ching-Chiung Wang ◽  
Wen-Chi Hou
Keyword(s):  
Agricultural Waste ◽  
Amyloid Β ◽  
Hot Water ◽  
Protein Glycation ◽  
Control Group ◽  
Amyloid Β Peptide ◽  
Hydrolysable Tannins ◽  
Inhibitory Activities ◽  
Tellimagrandin Ii

Agricultural waste from the hulls of water caltrop (Trapa taiwanesis Nakai, TT-hull) was extracted by either steeping them in cold 95% ethanol (C95E), refluxing 95E, refluxing 50E, or refluxing hot water (HW) to obtain C95EE, 95EE, 50EE, and HWE, respectively. These four extracts showed acetylcholinesterase (AChE) inhibitory activities and free radical scavenging activities, as well as anti-non-enzymatic protein glycation in vitro. Eight compounds were isolated from TT-hull-50EE and were used to plot the chromatographic fingerprints of the TT-hull extracts, among which tellimagrandin-I, tellimagrandin-II, and 1,2,3,6-tetra-galloylglucose showed the strongest AChE inhibitory activities, and they also exhibited anti-amyloid β peptide aggregations. The scopolamine-induced amnesiac ICR mice that were fed with TT-hull-50EE or TT-hull-HWE (100 and 200 mg/kg) or tellimagrandin-II (100 and 200 mg/kg) showed improved learning behavior when evaluated using passive avoidance or water maze evaluation, and they showed significant differences (p < 0.05) compared to those in the control group. The enriched hydrolysable tannins of the recycled TT-hull may be developed as functional foods for the treatment of degenerative disorders.

scholarly journals Anti-oxidative, acetylcholinesterase and pancreatic lipase inhibitory activities of compounds from Dasiphora fruticosa, Myricaria alopecuroides and Sedum hybridum

2017 ◽  
Vol 17 (43) ◽  
pp. 42-49 ◽  
Author(s):  
Odontuya G
Keyword(s):  
Gallic Acid ◽  
Pancreatic Lipase ◽  
Inhibitory Activity ◽  
Lipid Lowering ◽  
Lipase Enzyme ◽  
Quercetin Glycosides ◽  
Dpph Scavenging ◽  
Tellimagrandin Ii ◽  
Dasiphora Fruticosa ◽  
Potent Inhibitory Activity

Total of 35 phenolics and flavonols were isolated from flowers and leaves of Dasiphora fruticosa Rydb., from branches of Myricaria alopecuroides Schrenk. and from the herb of Sedum hybridum L. The isolated compounds were identified on the basis of spectral data and tested for their anti-oxidative, acetylcholinesterase and pancreatic lipase inhibitory activities.Quercetin glycosides, gallic acid, (-)EGCG and gossypetin-8-O-xylopyranoside tellimagrandin II exhibited strong anti-oxidative activity by the DPPH scavenging method. The acetylcholinesterase inhibitory activity of quercetin glycosides and (-)EGCG was higher than those of other compounds. Whereas, tellimagrandin II, (-)EGCG and gallic acid derivatives exhibited the most potent inhibitory activity against the pancreatic lipase enzyme among the isolated compounds. Only (-)EGCG showed a prominent activity against all assayed experiments. It was concluded that these plants could be studied further for their potential as anti-oxidative, anti-aging and lipid lowering active products.

scholarly journals Tellimagrandin II, A Type of Plant Polyphenol Extracted from Trapa bispinosa Inhibits Antibiotic Resistance of Drug-Resistant Staphylococcus aureus

2019 ◽  
Vol 20 (22) ◽  
pp. 5790 ◽  
Author(s):  
Yu-Wei Chang ◽  
Wan-Chun Huang ◽  
Chun-Yu Lin ◽  
Wen-Hung Wang ◽  
Ling-Chien Hung ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Inhibitory Concentration ◽  
Synergistic Effects ◽  
Drug Resistant ◽  
Penicillin Binding Protein ◽  
Antibacterial Effects ◽  
Transmission Electron ◽  
Antistaphylococcal Activity ◽  
Global Concern ◽  
Tellimagrandin Ii

The emergence of methicillin-resistant Staphylococcus aureus (MRSA) has become a critical global concern. Identifying new candidates of anti-S. aureus agents is urgently required because the therapeutic strategies for infected patients are limited currently. Therefore, the present study investigated whether Tellimagrandin II (TGII), a pure compound extracted from the shells of Trapa bispinosa, exhibits antibacterial effects against MRSA. We first showed that TGII exerted potent inhibitory activity against MRSA with a minimum inhibitory concentration of 128 μg/mL. The obtained fractional inhibitory concentration suggested that TGII could alone exert antistaphylococcal activity, and TGII combined with low doses of antibiotics displayed synergistic effects against MRSA. Moreover, we found that TGII exerted bactericidal activity by reducing the expression of mecA followed by the negative regulation of the penicillin-binding protein 2a (PBP2a) of MRSA. Transmission electron microscopy (TEM) images further confirmed that TGII destroyed the integrity of the cell wall of MRSA and caused the loss of cytoplasm content. In conclusion, we evidenced the antibacterial effects of TGII against MRSA, which enables the effective dose of current antibiotics to be reduced and the predicament of drug-resistant S. aureus isolates to be overcome.

scholarly journals Lipopolysaccharide-Induced Nitric Oxide and Prostaglandin E2 Production Is Inhibited by Tellimagrandin II in Mouse and Human Macrophages

Life ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 411
Author(s):  
Chun-Yu Lin ◽  
Shih-Han Kao ◽  
Ling-Chien Hung ◽  
Hsin-Ju Chien ◽  
Wen-Hung Wang ◽  
...  
Keyword(s):  
Nitric Oxide ◽  
Prostaglandin E2 ◽  
Inflammatory Diseases ◽  
Human Monocyte ◽  
Basic Mechanism ◽  
No Production ◽  
Microbial Infection ◽  
Cox 2 ◽  
Pre Treatment ◽  
Tellimagrandin Ii

Sepsis develops from a serious microbial infection that causes the immune system to go into overdrive. The major microorganisms that induce sepsis are Gram-negative bacteria with lipopolysaccharide (LPS) in their cell walls. Nitric oxide (NO) and cyclooxygenase-2 (COX-2) are the key factors involved in the LPS-induced pro-inflammatory process. This study aimed to evaluate the effects of polyphenol Tellimagrandin II (TGII) on anti-inflammatory activity and its underlying basic mechanism in murine macrophage cell line RAW 264.7 and human monocyte-derived macrophages. Macrophages with more than 90% cell viability were found in the cytotoxicity assay under 50 μM TGII. Pre- or post-treatment with TGII significantly reduced LPS-induced inducible nitric oxide synthase (NOS2) protein and mRNA expression, reducing LPS-induced COX-2 protein. Downstream of NOS2 and COX-2, NO and prostaglandin E2 (PGE2) were significantly inhibited by TGII. Upstream of NOS2 and COX-2, phospho-p65, c-fos and phospho-c-jun were also reduced after pre-treatment with TGII. Mitogen-activated protein kinases (MAPKs) are also critical to nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) stimulation, and phospho-p38 expression was found to have been blocked by TGII. TGII efficiently reduces LPS-induced NO production and its upstream regulatory factors, suggesting that TGII may be a potential therapeutic agent for sepsis and other inflammatory diseases.

scholarly journals Stability of Principal Hydrolysable Tannins from Trapa taiwanensis Hulls

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 365 ◽  
Author(s):  
Ching-Chiung Wang ◽  
Hsyeh-Fang Chen ◽  
Jin-Yi Wu ◽  
Lih-Geeng Chen
Keyword(s):  
Protective Effect ◽  
Water Solution ◽  
Gastric Fluid ◽  
Simulated Gastric Fluid ◽  
Intestinal Fluid ◽  
Buffer Solution ◽  
Simulated Intestinal Fluid ◽  
Hydrolysable Tannins ◽  
The Stability ◽  
Tellimagrandin Ii

The fruit and hulls of the water caltrop (Trapa taiwanensis Nakai) are used as hepatoprotective herbal tea ingredients in Taiwan. The stability of hydrolysable tannins in herbal drinks has rarely been reported. In the present study, two hydrolysable tannins, tellimagrandin II (TGII) and 1,2,3,4,6-pentagalloylglucopyranose (PGG), were isolated from water caltrop hulls. The stability of the two compounds was evaluated by treatment with various pH buffer solutions, simulated gastric fluid and intestinal fluid, different temperatures, and photo-irradiation at 352 nm in different solvents. Results showed that TGII and PGG were more stable in a pH 2.0 buffer solution (with 91.88% remaining) and in a water solution with 352 nm irradiation (with 95% remaining). TGII and PGG were more stable in methanol or ethanol solutions (with >93.69% remaining) than in an aqueous solution (with <43.52% remaining) at 100 °C. In simulated gastric fluid, more than 96% of the hydrolysable tannins remained after incubation at 37 °C for 4 h. However, these hydrolysable tannins were unstable in simulated intestinal fluid, as after incubation at 37 °C for 9 h, the content of TGII had decreased to 31.40% and of PGG to 12.46%. The synthetic antioxidants, butyl hydroxy anisole (BHA), di-butyl hydroxy toluene (BHT), and propyl gallate, did not exhibit photoprotective effects on these hydrolysable tannins. However, catechin, a natural antioxidant, displayed a weak photoprotective effect. Ascorbic acid had a short-term thermal-protective effect but not a long-term protective effect. The different stability properties of hydrolysable tannins in solutions can be used in the development of related herbal teas in the future.

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