Everything about Caffeic Acid totally explained
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Caffeic acid,
C9H8O4 is a naturally occurring
phenolic compound, (formerly called a carbolic acid), which is found in many
fruits,
vegetables, and
herbs, including
coffee, although varying in amounts depending on the
plant.
Caffeic acid has been shown to act as a
carcinogenic inhibitor. It is also known as an
antioxidant in vitro and also
in vivo.
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Caffeic acid is a yellow crystalline acid that's
soluble in hot water and
alcohol. It is related to
cinnamic acid, but it has two
hydroxyl groups not found in cinnamic acid. Both are part of the carbocyclic
carboxylic acid group.
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Caffeic acid can be esterified with
quinic acid to form
chlorogenic acid. Both caffeic acid and chlorogenic acid are found in coffee beans.
Caffeine is a different compound than caffeic acid. A derivative of caffeic acid is caffeic acid phenethyl ester (CAPE).
It is used as a matrix in
MALDI mass spectroscopy analyses.
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Biological importance
Caffeic acid and its derivative caffeic acid phenethyl ester (CAPE) are produced in many plants including:
pears,
basil,
thyme,
verbena,
tarragon,
oregano,
wood betony,
burning bush,
turmeric,
dandelion,
yarrow,
horsetail,
rosemary,
hawthorn and
coffee. The amount of caffeic acid is strongly dependent on the plant species.
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Both caffeic acid and chlorogenic acid have been shown to be absorbed in humans. Caffeic acid absorption is hampered when it's esterified with quinic acid to form chlorogenic acid.
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In laboratory experiments, colonies of a
nut tree mould were grown on extracts of
walnut and
pistachio. Next,
fungal colonies were exposed to three compounds thought to be
antioxidants:
gallic acid, which has
aflatoxin-combating impacts in
walnuts, and chlorogenic acid and caffeic acid.
Caffeic acid outperformed the other antioxidants, reducing aflatoxin production by more than 95 percent. The studies are the first to show that oxidative stress that would otherwise trigger or enhance
Aspergillus flavus aflatoxin production can be stymied by caffeic acid. This opens the door to using natural anti-
fungicide methods by supplementing trees with antioxidants.
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Pharmaceutical Uses
Oral administration of high doses of caffeic acid in rats has caused
stomach papillomas, leading to the perception of caffeic acid as carcinogenic. In the same study, only high doses of combined antioxidants, including caffeic acid, showed a significant decrease in growth of
colon tumors in those same rats. No significant effect was noted otherwise.
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Caffeic Acid is still listed under older Hazard Data sheets
(External Link) as a potential carcinogen because of two early experiments on rats and mice. More recent data show that
bacteria in the rats' guts may alter the formation of
metabolites of Caffeic Acid.
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(External Link) There have been no known ill-effects of Caffeic Acid in humans.
Caffeic Acid and its derivative, Caffeic Acid Phenethyl Ester (CAPE) have shown tumor-shrinking properties. When an anti-
cancer drug was being sought, Caffeic Acid and CAPE were derived from
Burning Bush (
Euonymus alatus). "The
subcutaneous and oral administrations of CA and CAPE significantly reduced
liver metastasis. These results confirm the
therapeutic potential of the compounds and suggest that the anti-metastatic and anti-tumor effects of CA and CAPE are mediated through the selective suppression of
MMP-9
enzyme activity and
transcriptional down-
regulation by the dual
inhibition of
NF-B as well as MMP-9
catalytic activity."
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A study using the caffeic acid phenethyl ester (CAPE) showed a positive effect on reducing
carcinogenic incidence. Caffeic acid phenethyl
ester (CAPE) is an active component of
propolis from
honeybee hives.
(External Link) It is known to have
antimitogenic, anticarcinogenic,
anti-inflammatory, and
immunomodulatory properties.
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Another study also showed that CAPE suppresses
acute immune and
inflammatory responses and holds promise for therapeutic uses to reduce inflammation.
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This anti-inflammatory and anti-cancer property has also been shown to protect
skin cells when exposed to
ultraviolet (UV)
radiation, in particular UVC radiation
(External Link) and UVB radiation.
(External Link). This anti-cancer effect was also seen when mice skin was treated with bee propolis and exposed to TPA (a
chemical) that induced skin
papillomas. CAPE significantly reduced the number of papillomas.
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Caffeic Acid and chlorogenic acid from coffee beans both reduced
DNA methylation in vitro in two lines of human cancer cells. DNA methylation contributes to the growth of tumors and regulates the
epigenetics of cells that are passed along with
DNA to future generations
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Caffeic acid has been shown to be an inhibitor of the lipoxygense enzyme that forms leukotrienes from the membrane-derived phospholipid arachadonic acid. this function has been useful in scientific experiments to elucidate the roles of the leukotrienes in various inflammatory responses.
Further Information
Get more info on 'Caffeic Acid'.
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