Ferulic acid is an antioxidant found naturally in plant cell walls, leaves and seeds. A good amount of ferulic acid is found in oats, brown rice, whole wheat, peanuts, apples, and pineapples.
Health benefit of ferulic acid
Ferulic acid
may be beneficial in the health of sperm and
fertility.
Food Chem Toxicology. 2014. Ferulic acid: Pharmacological and toxicological aspects. FA belongs to the family of phenolic acids and is very abundant in fruits and vegetables. Over the past years, several studies have shown that FA acts as a potent antioxidant by scavenging free radicals and enhancing the cell stress response through the up-regulation of cytoprotective systems, e.g. heme oxygenase-1, heat shock protein 70, extracellular signal-regulated kinase 1/2 and the proto-oncogene Akt. Furthermore, FA was shown to inhibit the expression and/or activity of cytotoxic enzymes, including inducible nitric oxide synthase, caspases and cyclooxygenase-2. Based on this evidence, FA has been proposed as a potential treatment for many disorders including Alzheimer's disease, cancer, cardiovascular diseases, diabetes mellitus and skin disease. However, despite the great abundance of preclinical research, only a few studies were carried out in humans, the majority of which used foods containing FA, and therefore the clinical efficacy of this mode of administration needs to be further documented.
Brain cell protection
Iran J Basic Med Sci. 2015. Ferulic acid protects PC12 neurons
against hypoxia by inhibiting the p-MAPKs and COX-2 pathways.
Chemistry
Ferulic acid is a ubiquitous plant constituent found in plant cell walls, leaves
and seeds. It is made from the metabolism
of phenylalanine and tyrosine. It occurs primarily in seeds and leaves both in
its free form and covalently linked to lignin and other biopolymers. Due to its phenolic nucleus and an extended side chain conjugation, it readily forms a
resonance stabilized phenoxy radical which accounts for its potent antioxidant
potential. UV absorption by ferulic acid catalyzes stable phenoxy radical
formation and thereby potentiates its ability to terminate free radical chain
reactions. By virtue of effectively scavenging deleterious radicals and
suppressing radiation-induced oxidative reactions, ferulic acid may serve an
important antioxidant function in preserving physiological integrity of cells
exposed to both air and impinging UV radiation. Similar photoprotection is
afforded to skin by ferulic acid dissolved in cosmetic lotions. Its addition to
foods inhibits lipid peroxidation and subsequent oxidative spoilage. By the same
mechanism ferulic acid may protect against various inflammatory diseases. A
number of other industrial applications are based on the antioxidant potential
of ferulic acid.
Ferulic acid and vanillin
Vanillin, vanillic and protocatechuic acids are catabolic products
of ferulic acid degradation. Conversion of ferulic acid to
vanillin occurs.
Ferulic acid is similar to curcumin in chemical structure. Ferulic acid is a
derivative of trans-cinnamic acid and a precursor to vanillin.
Ferulic acid in coffee
Coffee is particularly rich in bound phenolic acids, such as caffeic
acid, ferulic acid, and p-coumaric acid. Chlorogenic acid
(5'-caffeoylquinic acid), a bound form of caffeic acid, is present in
coffee at high levels. Wheat bran contains several ester-linked
dehydrodimers of ferulic acid.
Research
Amaranth as a rich dietary source of beta sitosterol and other phytosterols.
Plant Foods Hum Nutr. 2003.
The analysis of 4 commonly available amaranth varieties (Amaranthus K343,
RRC1011, K433, K432) revealed the presence of all three major phytosterols
(beta-sitosterol, campesterol, stigmas-terol) with a total sterol content being
several fold higher than those found in other studied plants. Substantial
differences in total phytosterol content and beta-sitosterol content were found
between the amaranth varieties. The most commonly cultivated amaranth variety in
the United States, i.e., Amaranthus K343 was found to possess the highest levels
of phytosterols of the varieties tested. The possibility of screening for
superior amaranth varieties with various health properties is outlined.
Ferulic acid is bound to the primary cell walls of
all gymnosperm families.
Biochem Syst Ecol. 2000.
Unlignified primary cell walls containing ester-linked ferulic acid
fluoresce blue in ultraviolet radiation which changes to green with
increased intensity on treatment with ammonium hydroxide. Using this
fluorescence behaviour, we detected ester-linked ferulic acid in the
primary cell walls of all 41 species of gymnosperms we examined. These
species were in 17 families representing all four extant classes of
gymnosperms. In addition, we obtained cell-wall preparations containing
>95% primary cell walls from nine gymnosperm species in nine families,
representing all four extant classes. These preparations were analysed for
ester-linked monomeric phenolic acids. We found ferulic acid (mostly
trans) (88-1,561microg/g cell walls) in all of the preparations and p-coumaric
acid (mostly trans) (0-106microg/g cell walls) in all except one of them.
Ferulic acid ester-linked to primary cell walls has previously been found
in angiosperms: in the commelinoid monocotyledons and in the dicotyledon
order Caryophyllales, both monophyletic groups. From the present results,
we postulate that the extant classes of gymnosperms are monophyletic and
no class is sister to the angiosperms.
Reactivity of ferulic acid and its derivatives toward hydrogen peroxide
and peracetic acid.
J Agric Food Chem. 1999.
The reactions of ferulic acid and its derivatives with hydrogen
peroxide and peracetic acid in lignin-retaining bleaching conditions have
been investigated to determine their susceptibility to oxidative
degradation. The conjugated side chain of ferulic acid and its etherified
or esterified derivative was shown to be fairly stable, especially to
hydrogen peroxide. The major reaction was trans-cis isomerization that
possibly involved a radical mechanism but did not cause bond cleavage. The
peracetic acid reaction increased the rate of trans-cis isomerization and
was also accompanied by a minor cleavage of the side chain. Esterification
did not have a substantial effect on the reactivity of ferulic acid, but
4-O-etherification significantly stabilized it against these two oxidants.
By contrast, aldehyde substitution tremendously enhanced the
susceptibility of the cinnamyl side chain to oxidative degradation, as
evidenced by an intensive degradation of coniferaldehyde.
Effects of ferulic acid on fertile and
asthenozoospermic infertile human sperm motility, viability, lipid
peroxidation, and cyclic nucleotides.
Free Radic Biol Med. 1997.
Department of Biology, Lanzhou University, P.R. China.
The capacity of human sperm fertilization principally depends on sperm
motility and membrane integrity. Reactive oxygen species, such as
superoxide anion and hydrogen peroxide, are known to impair sperm motility
and membrane integrity by inducing membrane lipid peroxidation (LPO).
Ferulic acid, an effective constituent in various medicinal herbs, has
recently been shown to scavenge oxygen free radicals and increase the
intracellular cAMP and cGMP. The aim of this study is to investigate the
effects of ferulic acid on human sperm motility, viability, lipid
peroxidation, and cyclic nucleotides in fertile and asthenozoospermic
infertile individuals in vitro. The results showed: in both fertile and
infertile spermatozoa, the viability, trans-membrane migration ratio (TMMR)
and the levels of intracellular cAMP and cGMP in ferulic acid -treated
spermatozoa were significantly higher than those of spermatozoa in control
groups, while TBA-reactive substances contents in treated spermatozoa were
significantly lower than those in control spermatozoa. The effects of
ferulic acid on these processes were concentration dependent. These data
suggested that ferulic acid is beneficial to sperm viability and motility
in both fertile and infertile individuals, and that reduction of lipid
peroxidative damage to sperm membranes and increase of intracellular cAMP
and cGMP may be involved in these benefits. It is possible that ferulic
acid may be used for cure of asthenozoospermic infertility.
Trans-4-hydroxy-3-methoxycinnamic acid (ferulic
acid) inhibits the effect of androgens on the rat prostate.
Experientia. 1979.
Trans-4-hydroxy-3-methoxycinnamic acid antagonized
the effect of exogenous androgens on the ventral prostate (VP) in
castrated rats as well as the effect of endogenous androgens in intact
rats. Ferulic acid, however, had no effect on the seminal vesicles (SV)
and levator ani muscle (LAM), nor oestrogenic effect in female rats and
mice. Ferulic acid did not antagonize the receptor binding of testosterone
nor inhibit the conversion of testosterone into 5 alpha-dihydrotestosterone
(DHT).