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Chemical Structure| 327-97-9 Chemical Structure| 327-97-9

Structure of Chlorogenic acid
CAS No.: 327-97-9

Chemical Structure| 327-97-9

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Chlorogenic acid, a major phenolic compound in Lonicera japonica Thunb., is an orally active compound with antioxidant, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, antimicrobial, and antihypertensive properties.

Synonyms: 3-O-Caffeoylquinic acid; Heriguard; 3transCaffeoylquinic acid

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Minwoo Bae ; Chi Le (Chip) ; Raaj S. Mehta ; Xueyang Dong ; Lindsey M. Pieper ; Lorenzo Ramirez , et al.

Abstract: Gut microbial catechol dehydroxylases are a largely uncharacterized family of metalloenzymes that potentially impact human health by metabolizing dietary polyphenols. Here, we use metatranscriptomics (MTX) to identify highly transcribed catechol-dehydroxylase-encoding genes in human gut microbiomes. We discover a prevalent, previously uncharacterized catechol dehydroxylase (Gp Hcdh) from Gordonibacter pamelaeae that dehydroxylates hydrocaffeic acid (HCA), an anti-inflammatory gut microbial metabolite derived from plant-based foods. Further analyses suggest that the activity of Gp Hcdh may reduce anti-inflammatory benefits of polyphenol-rich foods. Together, these results show the utility of combining MTX analysis and biochemical characterization for gut microbial enzyme discovery and reveal a potential link between host inflammation and a specific polyphenol-metabolizing gut microbial enzyme.

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Krysa, Martyna ; Szymańska-Chargot, Monika ; Pieczywek, Piotr M ; Adamczuk, Agnieszka ; Pertile, Giorgia ; Frąc, Magdalena , et al.

Abstract: The study of plant waste-based composites as alternatives to plastic is significant due to their biodegradability and environmental impact. However, composites based on natural plant fibers still need improvement, particularly in terms of mechanical, hydrophobic, antioxidant, and antimicrobial properties. Bioactive compounds such as phenolic acids may enhance these properties. This study aims to elucidate the mechanisms and effects of polysaccharide films made from micro- and nanofibrillated cellulose derived from apple pomace, and the adsorption of phenolic acids (caffeic, chlorogenic, and gallic acids) on their surface. Molecular interactions affecting the surface, mechanical, antioxidant, and antimicrobial properties of the composites were investigated. Raman spectroscopy revealed spectral changes in C-O and C-OH bonds, which influenced the composites’ surface wettability. Nanocellulose-based composites with caffeic acid exhibited the best packaging properties, including a homogeneous structure, increased stiffness, deformation resistance, and enhanced hydrophobicity. Composites with gallic acid showed the highest surface hydrophilicity and antioxidant capacity. Understanding these molecular interactions can aid in the further development of packaging materials

Keywords: Plant waste-based composites ; Apple pomace ; Polysaccharide films ; Antioxidant properties ; Molecular structure ; Surface properties

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Scott, Jared Lee ;

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

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Product Details of Chlorogenic acid

CAS No. :327-97-9
Formula : C16H18O9
M.W : 354.31
SMILES Code : O=C([C@@]1(O)C[C@@H](OC(/C=C/C2=CC=C(O)C(O)=C2)=O)[C@H](O)[C@H](O)C1)O
Synonyms :
3-O-Caffeoylquinic acid; Heriguard; 3transCaffeoylquinic acid
MDL No. :MFCD00003862
InChI Key :CWVRJTMFETXNAD-JUHZACGLSA-N
Pubchem ID :1794427

Safety of Chlorogenic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
Caco-2 cells 5, 10, 20, 30 μg/mL 24 hours To evaluate the repair effects of EVs and GEVs on LPS-induced Caco-2 cell injury, results showed that the 10 μg/mL dose group exhibited higher cell viability, especially in the GEV group. Adv Sci (Weinh). 2023 Oct;10(28):e2302798.
Human Dermal Fibroblasts (HDF-α) 0.1 to 3 µM 48 hours CGA significantly up-regulated Col1 mRNA and protein expressions and increased collagen secretion in the supernatant of HDF-α cells without affecting cell viability Int J Mol Sci. 2022 Jun 22;23(13):6941.
Human Dermal Fibroblasts (HDF-α) 0.3 to 10 µM 48 hours CGA significantly enhanced Col1A1 and Col1A2 mRNA levels, especially Col1A2 mRNA expression Int J Mol Sci. 2022 Jun 22;23(13):6941.
Human melanoma cell line A375 0, 25, 50, 100, 200 µM 48 hours Chlorogenic acid significantly suppressed IFN-γ-induced PD-L1 expression Int J Biol Sci. 2024 Jan 1;20(1):61-77.
Ovarian cancer cell line SK-OV-3 0, 25, 50, 100, 200 µM 48 hours Chlorogenic acid significantly suppressed IFN-γ-induced PD-L1 expression Int J Biol Sci. 2024 Jan 1;20(1):61-77.
Triple-negative breast cancer cell line MDA-MB-231 0, 25, 50, 100, 200 µM 48 hours Chlorogenic acid significantly suppressed IFN-γ-induced PD-L1 expression Int J Biol Sci. 2024 Jan 1;20(1):61-77.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL/6 mice High-fat diet-induced prediabetes mouse model Gavage 100 mg/kg Three times per week for 10 weeks To investigate the effects of chlorogenic acid on hepatic lipid metabolism in high-fat diet-induced prediabetes mice, the results showed that CGA improved glucose and lipid metabolism Diabetes Metab J. 2023 Nov;47(6):771-783
Sprague Dawley rats PI-IBS rat model Rectal administration 50 mg/kg Once daily for one week To evaluate the alleviating effects of chlorogenic acid on PI-IBS symptoms in rats, results showed that rectal administration significantly reduced visceral sensitivity, inflammatory reactions, and mucosal damage. Adv Sci (Weinh). 2023 Oct;10(28):e2302798.
Mice MC38 colon cancer model and 4T1 breast cancer model Intraperitoneal injection 50 mg/kg Once daily for 21 days or 19 days Combination therapy of chlorogenic acid with anti-PD-1 antibody significantly suppressed tumor growth and reduced the expression of PD-L1 and IRF1 in tumor tissues Int J Biol Sci. 2024 Jan 1;20(1):61-77.

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02245204 Advanced Cancer PHASE1 COMPLETED 2025-10-16 Beijing Cancer Hospital, Beiji... More >>ng, 100142, China Less <<
NCT02728349 Glioblastoma PHASE1 COMPLETED 2017-09-13 Beijing Shijitan Hospital,Capi... More >>tal Medical University, Beijing, 100038, China Less <<
NCT03751592 Advanced Lung Cancer PHASE1|PHASE2 UNKNOWN 2021-04-30 Cancer Hospital Chinese Academ... More >>y of Medical Sciences, Beijing, 100021, China Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

2.82mL

0.56mL

0.28mL

14.11mL

2.82mL

1.41mL

28.22mL

5.64mL

2.82mL

Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1
Protocol 2

References

 

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