A caffeic acid ester from Halocnemum strobilaceum

Caffeic acid is a bioactive compound found in a variety of plants including vegetables, fruits, herbs, and drinks. It belongs to the huge group of chemicals called polyphenols and is a major representative of the polyphenol subgroup of hydroxycinnamic acids. In foods, caffeic acid occurs mostly as a quinic acid ester called chlorogenic acid. Caffeic acid, like other polyphenols, is believed to exhibit many health benefits associated with their antioxidant properties, including the prevention of inflammation, cancer, neurodegenerative diseases, and diabetes. Nowadays, the use of naturally occurring bioactive substances, including caffeic acid, is becoming a very common phenomenon. Thus, information about their functions and properties is very important.Keywords: caffeic acid, polyphenols, bioactive compound, oxidative stress

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A caffeic acid ester mediates host recognition by a parasitic wasp

The Science of Nature ◽

10.1007/bf01140427 ◽

1993 ◽

Vol 80 (2) ◽

pp. 92-94 ◽

Cited By ~ 12

Author(s):

J. D. Hare ◽

J. G. Millar ◽

R. F. Luck

Keyword(s):

Caffeic Acid ◽

Acid Ester ◽

Parasitic Wasp ◽

Host Recognition

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Absolute configuration assignment of caffeic acid ester derivatives from Tithonia diversifolia by vibrational circular dichroism: the pitfalls of deuteration

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2017.10.025 ◽

2017 ◽

Vol 28 (12) ◽

pp. 1823-1828 ◽

Cited By ~ 5

Author(s):

Gari V. Ccana-Ccapatinta ◽

Bruno L. Sampaio ◽

Fernando M. dos Santos ◽

João M. Batista ◽

Fernando B. Da Costa

Keyword(s):

Circular Dichroism ◽

Caffeic Acid ◽

Absolute Configuration ◽

Acid Ester ◽

Vibrational Circular Dichroism ◽

Tithonia Diversifolia ◽

Configuration Assignment ◽

Circular Dichroïsm

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2-Deoxyglycosylation towards more effective and bioavailable neuroprotective molecules inspired by nature

Pure and Applied Chemistry ◽

10.1515/pac-2019-0303 ◽

2019 ◽

Vol 91 (7) ◽

pp. 1209-1221

Author(s):

Catarina Dias ◽

Ana M. Matos ◽

Maria T. Blásquez-Sanchez ◽

Patrícia Calado ◽

Alice Martins ◽

...

Keyword(s):

Central Nervous System ◽

Nervous System ◽

Caffeic Acid ◽

Acid Ester ◽

Water Solubility ◽

Artificial Membrane ◽

Natural Polyphenols ◽

D Values ◽

Permeability Assay

Abstract The neuroprotective role of natural polyphenols is well established but phenolics poor water solubility affects their bioavailability and bioactivity. Aiming to overcome this issue, we were encouraged to investigate the 2-deoxyglycosylation of natural or nature inspired neuroprotective molecules, using glycals as easily accessed glycosyl donors. This robust methodology allowed the generation of a set of new resveratrol and caffeic acid ester glycosides, envisioning more effective and bioavailable compounds. Resveratrol 2-deoxyglycosides were more effective at protecting the neuronal cells from peroxide-induced cytotoxicity than resveratrol itself, while the caffeic acid ester glycoside also showed extraordinary neuroprotection activity. Coefficient partition measurements demonstrated the moderate lipophilicity of resveratrol glycosides, which Log D values are typical of a central nervous system (CNS) drug and ideal for blood-brain barrier (BBB) penetration. Passive permeation assessed by the parallel artificial membrane permeability assay (PAMPA) revealed that 2,6-dideoxy-l-arabino-hexopyranosides were more effective than 2-deoxy-d-arabino-hexopyranosides. The lack of toxicity of the neuroprotective glycosides and their promising physicochemical properties revealed the usefulness of sugar coupling towards the modulation of natural product properties and bioactivity.

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