Hydroxycinnamic acid
Hydroxycinnamic acids (hydroxycinnamates) are a class of Aromatic acids or phenylpropanoids having a C6-C3 skeleton. These compounds are hydroxy derivatives of cinnamic acid.
In the category of phytochemicals that can be found in food, there are :
- α-Cyano-4-hydroxycinnamic acid
- Caffeic acid – burdock, hawthorn, artichoke, pear, basil, thyme, oregano, apple
- Cichoric acid
- Cinnamic acid – aloe
- Chlorogenic acid – echinacea, strawberries, pineapple, coffee, sunflower, blueberries
- Diferulic acids
- Coumaric acid
- Coumarin – citrus fruits, maize
- Ferulic acid (3-methoxy-4-hydroxycinnamic acid) – oats, rice, artichoke, orange, pineapple, apple, peanut
- Sinapinic acid (3,5-dimethoxy-4-hydroxycinnamic acid or sinapic acid)
Hydroxycinnamoyltartaric acids
|
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| | Aglycones | Precursor | |
|---|
| Monohydroxycinnamic acids
(Coumaric acids) | |
|---|
| | |
|---|
| Trihydroxycinnamic acids |
- 3,4,5-Trihydroxycinnamic acid
- 3,4,6-Trihydroxycinnamic acid
|
|---|
| O-methylated forms | |
|---|
| others | |
|---|
|
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| | Esters | glycoside-likes | Esters of
caffeic acid
with cyclitols | esters of
quinic acid |
- Chlorogenic acid (3-caffeoylquinic acid)
- Cryptochlorogenic acid (4-O-caffeoylquinic acid)
- Neochlorogenic acid (5-O-Caffeoylquinic acid)
- Cynarine (1,5-dicaffeoylquinic acid)
- 3,4-dicaffeoylquinic acid
- 3,5-dicaffeoylquinic acid
|
|---|
| esters of
shikimic acid | |
|---|
|
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| Glycosides | |
|---|
|
|---|
| Tartaric acid esters | |
|---|
| Other esters
with caffeic acid | |
|---|
| Caffeoyl phenylethanoid
glycoside (CPG) |
- Echinacoside
- Calceolarioside A, B, C and F
- Chiritoside A, B and C
- Cistanoside A, B, C, D, E, F, G an H
- Conandroside
- Myconoside
- Pauoifloside
- Plantainoside A
- Plantamajoside
- Tubuloside B
- Verbascoside (Isoverbascoside, 2'-Acetylverbascoside)
|
|---|
|
|---|
| | Oligomeric forms | Dimers |
- Diferulic acids (DiFA) : 5,5'-Diferulic acid, 8-O-4'-Diferulic acid, 8,5'-Diferulic acid, 8,5'-DiFA (DC), 8,5'-DiFA (BF), 8,8'-Diferulic acid
|
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| Trimers | |
|---|
| Tetramers | |
|---|
|
|---|
| Conjugates with
coenzyme A | |
|---|
|
References
- ↑ Straightforward Method To Quantify GSH, GSSG, GRP, and Hydroxycinnamic Acids in Wines by UPLC-MRM-MS. Anna Vallverdú-Queralt, Arnaud Verbaere, Emmanuelle Meudec, Veronique Cheynier and Nicolas Sommerer, J. Agric. Food Chem. 2015, 63, 142−149, doi:10.1021/jf504383g
- ↑ 2.0 2.1 2.2 Vrhovsek U. (1998). "Extraction of Hydroxycinnamoyltartaric Acids from Berries of Different Grape Varieties". J Agric Food Chem. 46: 4203–8. doi:10.1021/jf980461s.