|Molar mass||354.31 g·mol−1|
|Melting point||207 °C (405 °F; 480 K)|
|S-phrases||S24 S25 S28 S37 S45|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Chlorogenic acid (CGA) is a natural chemical compound which is the ester of caffeic acid and (−)-quinic acid. It is an important biosynthetic intermediate. Chlorogenic acid is an important intermediate in lignin biosynthesis. This compound, known as an antioxidant, may also slow the release of glucose into the bloodstream after a meal.
Despite the "chloro" of the name, chlorogenic acids contain no chlorine. Instead, the name comes from the Greek χλωρός (light green) and -γένος (a suffix meaning "giving rise to"), because of the green color produced when chlorogenic acids are oxidized.
Isomers of chlorogenic acid include 4-O-caffeoylquinic acid (cryptochlorogenic acid or 4-CQA), 5-O-caffeoylquinic acid (neochlorogenic acid or 5-CQA). The epimer at position 1 has not yet been reported.
Isomers containing two caffeic acid molecules are called isochlorogenic acid. It can be found in coffee. There are several isomers such as 3,4-dicaffeoylquinic acid and 3,5-dicaffeoylquinic acid Cynarine (1,5-dicaffeoylquinic acid) is an other isomer with two caffeic acid molecules..
Isomers of chlorogenic acid are found in potatoes.
Chlorogenic acid can be found in bamboo Phyllostachys edulis. as well as in many other plants. It is one of the major phenolic compounds identified in peach and in prunes. It also is one of the phenols found in green coffee bean extract.
Chlorogenic acid is marketed under the tradename Svetol, a standardized green coffee extract, as a food additive used in coffee products, chewing gum, and mints, and also as a stand-alone product. Dried sunflower leaves collected immediately after opening are processed into 98.38% chlorogenic acid extract and marketed in Bulgaria under the name of "Yamiagra"or "Yummyiagra".
Review articles in 2014 and 2011 report modest, but significant, blood pressure lowering effects from chlorogenic acid administration. No studies have appeared to assess possible interactions with antihypertensive drugs or advisability in patients being treated for low blood pressure.
One study showed that chlorogenic acid may have weak psychostimulant effects in mice.
Another study showed chlorogenic acid to have a protective effect in neuroinflammatory conditions on dopaminergic neurons.
In an online news story article appearing in MSN Healthy Living, accessed in May 2014, scientists gave mice nitric oxide (NO), which creates oxidative stress and promotes the formation of certain harmful free radicals, leading to (among other problems) retinal degeneration, which impairs the crucial rods and cones and leads to other retinal tissue damage, and ultimately, loss of sight. Any animal's retina- whether in mice or in humans or other species- is very metabolically active, and requires, like the brain it communicates with via the optic nerve, a consistently high and steady supply of uncontaminated oxygen. The mice exposed to the nitric oxide who were pretreated with chlorogenic acid (CLA) did not develop any detectable signs of retinal damage.
Chlorogenic acid (CGA), at a level equivalent to the CGA in three cups of coffee a day for humans, added to the diet of mice in a mouse model for colon cancer, reduced colon cancer incidence from 56% to 18%. To cause cancer in the model diet, a standard diet plus 0.2% deoxycholate (DOC) was used, to raise the level of DOC in the colons of the mice to the level of DOC in colons of humans on a high fat Western diet. DOC is a natural endogenous component of the digestive system in humans and is considerably increased in the human colon when a high fat diet is eaten.
In mice on diet plus DOC, as in humans progressing to colon cancer, 8-OH-dG was substantially increased, DNA repair protein ERCC1 was strongly decreased, autophagy protein beclin-1 was strongly increased and, in the stem cell region at the base of crypts there was substantial nuclear localization of beta-catenin as well as considerably increased cytoplasmic beta-catenin. However, in mice with both CGA and DOC added to their diet (with reduced frequency of cancer), mouse tissue showed almost complete amelioration of the aberrancies in ERCC1, beclin-1 and beta-catenin (8-OH-dG was not measured), suggesting that chlorogenic acid is protective at the molecular level against colon cancer.
As reviewed by Scott et al., the DNA damage 8-OH-dG is carcinogenic. In a rat model leading to tongue cancer, in which the oxygen radical forming carcinogen 4-NQO was added to drinking water, 8-OH-dG increased with carcinogen treatment. However, also adding chlorogenic acid to the rat diet brought the 8-OH-dG level back to normal. In another report, feeding of chlorogenic acid starting one week before exposure to 4-NQO significantly reduced the incidences of tongue neoplasms (squamous cell papilloma and carcinoma) and preneoplastic lesions (hyperplasia and dysplasia).
DNA damages are a major primary cause of cancer. If a compound increases DNA repair, this would indicate a likely protective role against cancer. In a study of 19 antioxidants applied to cells in vitro, only chlorogenic acid and three metabolic by-products of chlorogenic acid [ m-coumaric acid, 3-(m-hydroxyphenyl) propionic acid and caffeic acid] increased the protein expression of two tested DNA repair enzymes, PARP and PMS2.
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- "Effects of chlorogenic acid and its metabolites on spontaneous locomotor activity in mice.". Biosci Biotechnol Biochem 70 (10): 2560–3. 2006. doi:10.1271/bbb.60243. PMID 17031047.
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