Phenolic compounds are synthesized industrially; they also are produced by

plants and microorganisms, with variation between and within species. Although similar
to alcohols, phenols have unique properties and are not classified as alcohols (since the
hydroxyl group is not bonded to a saturated carbon atom). They have
higher acidities due to the aromatic ring's tight coupling with the oxygen and a relatively
loose bond between the oxygen and hydrogen. The acidity of the hydroxyl group in
phenols is commonly intermediate between that of aliphaticalcohols and carboxylic
acids (their pKa is usually between 10 and 12). Loss of a positive hydrogen ion (H +) from
the hydroxyl group of a phenol forms a corresponding negative phenolate
ion or phenoxide ion, and the corresponding salts are
called phenolates or phenoxides, although the term aryloxides is preferred according
to theIUPAC Gold Book. Phenols can have two or more hydroxy groups bonded to the
aromatic ring(s) in the same molecule. The simplest examples are the
three benzenediols, each having two hydroxy groups on a benzene ring. Organisms that
synthesize phenolic compounds do so in response to ecological pressures such as
pathogen and insect attack, UV radiation and wounding. As they are present in food
consumed in human diets and in plants used in traditional medicine of several cultures,
their role in human health and disease is a subject of research. Some phenols are
germicidal and are used in formulating disinfectants. Others
possess estrogenic or endocrine disrupting activity.
Phenolic compounds including simple phenols and phenolic acids,
hydroxycinnamic acid derivatives and flavonoids are bioactive
substances occurring widely in food plants. Phenolic compounds are
closely associated with the sensory and nutritional quality of fresh and
processed plant foods. The enzymatic browning reaction of phenolic
compounds, catalyzed by polyphenoloxidase, could cause the
formation of undesirable color and flavor and the loss of nutrient in
fruits and vegetables. Many phenolic compounds in plants are good
sources of natural antioxidants. It is a great interest in recent years that
many phenolic compounds in foods have inhibitory effects on
mutagenesis and carcinogenesis.The term 'phenolic' or 'polyphenol' can be defined
chemically as a substance which possesses an aromatic ring bearing one or more
hydroxy substituents, includingfunctional derivatives (esters, methyl ethers, glycosides
etc.). Most phenolics have two or more hydroxyl groups and are bioactive substances
occurring widely in food plants that are eaten regularly by substantial numbers of
people.
Phenolics are not the only cause of these maladies, and phenolic therapy is not a
"cureall", but Scientific studies and anecdotal experiences demonstrate that phenolics
do play a large part in many disease processes.Plants produce a large variety of
secondary compounds containing a phenol group. These phenolic compounds are
synthesized via two different routes: the shikimate pathway and the acetate-malonate
pathway, and thus represent a heterogeneous group. The shikimate pathway
participates in the synthesis of most plant phenolics, whereas the malonate pathway is

of less significance in higher plants, although it is an important source of phenolic

products in fungi and bacteria. (Taiz and Zeiger, 2002).
Phenolic compounds are classified into several groups, including anthocyanins, the
pigments that attract animals; flavonoids, the compounds to serve as ultraviolet light
protectants; isoflavonoids (phytoalexins), the compounds that act as antifungal and
antibacterial defences; lignin, the phenolic macromolecule which is involved in
mechanical support and protection; and tannins, polymeric phenolic compounds that
function as feeding deterrents to herbivores.
Most classes of phenolic compounds in plants are derived from phenylalanine and
tyrosine, andin most plant species the key step of the biosyntheses is the conversion of
phenylalanine to cinnamic acid by the elimination of an ammonia molecule. The reaction
is catalyzed by phenylalanine ammonia lyase (PAL), an important regulatory enzyme of
secondary metabolism (Yao et al., 1995). Evidences suggest that phenylpropanoid
pathway intermediates can regulate the expression of the pathway at the transcriptional
and posttranslational levels. For an example, the biosyntheses of phenylpropanoids
increase in cultured pine and soybean cells after treatment with a fungal elicitor and
have been correlated with increase of PAL activity (Campbell and Ellis, 1992). In
contrast, the inhibition of PAL activity by the mechanism of co-suppression
reduced the accumulation of chlorogenic acid in transgenic tobacco plants Plant
phenolics and polyphenols are secondary natural metabolites arising biogenetically
from either the shikimate/phenylpropanoid pathway, which directly provides
phenylpropanoids, or the polyketide acetate/malonate pathway, which can produce
simple phenols, or both, thus producing monomeric and polymeric phenols and
polyphenols, which fulfill a very broad range of physiological roles in plants. Higher
plants synthesize several thousand known different phenolic compounds. The ability to
synthesize phenolic compounds has been selected throughout the course of evolution
in different plant lineages, thus permitting plants to cope with the constantly changing
environmental challenges over evolutionary time.
Plant phenolics are considered to have a key role as defense compounds when
environmental stresses, such as high light, low temperatures, pathogen infection,
herbivores, and nutrient deficiency, can lead to an increased production of free radicals
and other oxidative species in plants. Both biotic and abiotic stresses stimulate carbon
fluxes from the primary to the secondary metabolic pathways, thus inducing a shift of
the available resources in favor of the synthesis of secondary products. An interesting
link between primary and secondary metabolism couples the accumulation of the stress
metabolite proline with the energy transfer toward phenylpropanoid biosynthesis via the
oxidative pentose phosphate pathway. The alternating oxidation of NADPH by proline
synthesis and reduction of NADP+ by the two oxidative steps of the oxidative pentose
phosphate pathway lead to the simultaneous accumulation of phenolic compounds.