Medicinal plants and medical plant
materials that contain phenol
compounds, simple phenols and
their glycosides
Planner
1.
Phenolic
compounds
and
their
classification.
2. Biosynthesis of phenolic compounds.
3. MP and MPM containining simple phenols
and phenolic glycosides.
Phenolic compounds are the substances
containing benzoic nucleus with one or several
hydroxylic groups and their derivatives. If the
molecule contains two or more hydroxylic
groups there is polyphenols.
Phenolic compounds with one benzoic nucleus
Basic
skeleton
Class
Examples
C6
Simple phenols,
Benzoquinones
Catechol, Hydroquinone, 2,6Dimethoxybenzoquinone, phenol,
pirocatechol
C6-1
Alkilphenol
Phenolic alcohol
Phenolic aldehydes
Phenolic acids
p-cresol
Saligenin
Vanilin, Salicylic
Gallic, salicylic
C6-C2
Acetophenones, Tyrosine
derivatives, Phenylacetic acids
3-Acetyl-6-methoxybenzaldehyde, Tyrosol, pHydroxyphenylacetic acid
Hydroxycinnamic acids,
Phenylpropenes, Coumarins,
Isocoumarins, Chromones
Caffeic, ferulic acids, Myristicin, Eugenol,
Umbelliferone, aesculetin, Bergenon,
Eugenin
Naphthoquinones
Juglone, Plumbagin
C6-C3
C6-C4
Simple phenols
Phenolic acid
Phenolic alcohol
Acetophenone
Phenolic aldihyde
Phenylacetic acid
Hydroxycinnamic acid
Coumarin
Isocoumarin
Chromone
Phenolic compounds with two benzoic nucleus
Basic skeleton
Class
Examples
C6-C1-C6
Xanthonoids
Mangiferin
C6-C2-C6
Stilbenoids, Anthraquinones
Resveratrol, Emodin
C6-C3-C6
Chalconoids, Flavonoids,
Isoflavonoids,
Neoflavonoids
Quercetin, cyanidin, Genistein
(C6-C3)2
Lignans, Neolignans
Pinoresinol, Eusiderin,
rosmarinic acid
Polymeric compounds (polyphenols)
(C6-C3)n,
(C6)n,
(C6-C3-C6)n
Lignins,
Catechol melanins,
Flavolans (Condensed
tannins),
Polyphenolic proteins,
Polyphenols
Raspberry ellagitannin,
Tannic acid
C6-C1-C6
Benzophenones
Xantones
Stilbenes
Flavonoids
Biosynthesis some natural compounds
p-hydroxycinnamic (p-coumaric) acid
Phenolic
acid
Acetophenones
Phenilacetate acids
reducing,
dimerization
polymerisation
+ malonat
3 molecules
Combined forms
of hydroxycinnamic
acids
oxidation
Stilbens
Lignans
Lignins
Coumarins
Phlavonoids
Pyrocatechin
Hydroquinone
Pyrogalol
Phloroglucinol
Salicine
Salidroside
Phenol
Salicylic
alcohol
Salicylic aldehyde
Physicochemical properties
Free phenolics and their glycosides are crystals
of white and yellow colour with a fixed melting point,
soluble in water, ethanol, methanol, ethyl acetate,
water solution of alkali and sodium acetate and
insoluble in ether or chlorophorm. All glycosides
possess optical rotation. They can hydrolyse while
heated with mineral acids.
Extraction. Most phenolic acid derivatives accumulated
in the plant matrix are stored in vacuoles and are commonly
extracted with alcoholic or organic solvents. The common
solvents for extractions are hot water, ethanol, acetone, diethyl
ether, chloroform, ethyl acetate, and methanol (or aqueous
methanol), the latter being the most common. The following
liquid-solid extraction methods may be used: Soxhlet
extraction, ultrasonification (USAE), microwave-assisted
extraction (MAE), and accelerated solvent extraction (ASE).
Hydrolysis of the esters and glycosides to a free
phenolic acid has been a strategy employed to simplify the
analysis. There are two main procedures to cleave the ester
and glycoside bond: acidic hydrolysis (for glycosides), and
alkaline hydrolysis (for esters). A third, less prevalent
technique is cleavage through the use of enzymes (esterases or
glucosidases).
IDENTIFICATION
Phenolic compounds react with diazonium salts, iron alum (ferric
ammonium sulphate), ferric (III) chloride, lead (II) acetate (sediment).
•
An azo coupling is an organic reaction between a diazonium
compound and a phenol or other aromatic compound, which produces an
azo compound. The product will absorb longer wavelengths of light than
the reactants because of increased conjugation. Aromatic azo
compounds tend to be brightly coloured (red, orange) due to the
extended conjugated systems; many are used as dyes.
•Phenolic acids are substances, which absorb in the UV region and their
detection on thin layers containing a fluorescent indicator is relatively
easy.
TLC is widely used for qualitative analysis of phenolics. The
advantage of separation on thin layer is possibility of additional detection
after treatment by various reagents. The simple way of detection is
treatment the plates with ammonia vapour. Phenolic compounds should
be observed in the UV light at λ=254 or 366 nm.
Quantitative analysis
Titration can be used for quantitative analysis of phenolic compounds.
The most common types of titrations used are acid-base titration
(alkalimetry) and red-ox titrations (iodometry, bromatometry). For
example, the State Pharmacopoeia of the USSR of the XI edition
suggested using iodometry for qualitative analysis of arbutin in bearberry
leaves.
The British Pharmaopoeia 2009 and Europe Ph. suggest using
liquid chromatography for quantative analysis of arbutin.
TLC combined with densitometry is often used for quantitative
analysis of phenolic compounds in different parts of plants and herbs.
Biological Action and Application
Stress conditions such as excessive UV light, wounding, or
infection induce biosynthesis of phenolic compounds. Thus,
environmental factors may have a significant contribution to the content
of phenolic acids in plants.
Most of them have shown an excellent scavenging activity of
active oxygens. The antioxidant activity of phenolic acids and their
ethers depends on the number of hydroxyl groups.
Recent investigations have linked a series of phenolic acids
(ferulic, caffeic, ellagic, tannic, protocatechuic, chlorogenic, rosmarinic
acids, and curcumin) with the anticancer activity. Some of phenolic acids
(caffeic, gentisic, rosmarinic, ferulic, salicylic acids, curcumin) have
anti-inflammatory and antirheumatic properties. Caffeic acid is known as
a selective blocker of the biosynthesis of leukotrienes, components
involved in inflammatory and immunoregulation diseases, asthma, and
allergic reactions.
In recent years, more and more clinical studies were focused on
phenolic acids as a group of potential immunostimulating compounds.
Possibly, systemic application of caffeic, gallic, or salicylic acid could
result in suppression of leukocytes accumulation in extravascular sites,
that may be beneficial in the treatment of chronic inflammatory diseases.
Chlorogenic, ellagic, gallic, caffeic, protocatechuic, and salicylic acids
have significant stimulatory influence on the production IgG antibodies.
Phenolic acids are currently being investigated for their potential
antiviral therapy (rosmarinic, caffeic, ferulic acids).
There are other biological activities of phenolic acids: astringent
(rosmarinic acid), sedative on the central nervous system (rosmarinic
acid, chlorogenic acid), choleretic and cholekinetic (most of phenolic
acids), hepatoprotective, analgetic, antipyretic, and keratolytic (salicylic
acid).
Uvae ursi folia, Eu Ph
Arctostaphylos uva-ursi - Bearberry
Ericaceae
BAS: leaves – arbutin glicosides
(8-12
%),
methylarbutin,
hydroquinone, galic, elagic acids,
tannins (7-19 %), (+)-catechol,
triterpenoid saponins α-amyrin ursolic acid and flavonoids
(hyperoside,
quercetin,
kaempferol).
Arbutin
Methylarbutin
Arbutin
Hydroquinon
It can be used to treat arthritis, back pain, bed wetting,
bile problems, bladder infections, bloating, cystitis, diabetes
(by removing excessive sugar from the blood), diarrhoea,
gallstones, gonorrhoea, haemorrhoids, kidney stones and other
diseases
It has a strong bacteriostatic action against
Staphylococci and E. coli
It is advised to use bearberry no more than 7-10 days at
a time.
Decoctum is the component of the diuretic herbal composition
Vitis idaea folia
Vaccinium vitis idaea – cowberry,
lingonberry,, foxberry, mountain cranberry
Ericaceae
Constituents. Up to 9 % arbutin,
methylarbutin and melampsorine,
hedroquinone; up to 10 % tannins,
phenolic acids, flavonoids, ursolic,
quinic, ellagic and gallic acid.
• Medicines have diuretic and antiseptic
action and are used in treatment of cystitis,
gonorrhea, pyelonephritis , acute and
chronic urinary inflamation.
• “Brusniver”, it’s a diurenic and nephrolitic
herbal composition.
• Leaves of cowberrycontain less tannins
than leaves of bearberry and thus can be
prescribed for people with kidney disease.
• Inhalations and sprays from lingonberry
extract can be used for complex treatment
of pneumonia and bronchitis.
• For treatment of stomatitis, parodontitis,
angina, chronic tonsillitis, gingivitis,
mouth ulcers the decoction is prescribed
as rinsing agent
• It is used at light forms of diabetis.
Rhodiolae roseae rhizomata et radices
Rhodiola rosea- Golden root, roseroot,
Aaron’s root
Crassulaceae
Constituents.
Phenolic
glycoside
salidroside (up to 1 %), rosavin, rosin,
hedrolysable tannins (up to 20 %),
flavonoids
(kaempferol,
quercetin,
isoquercetin, hyperoside, rodiolin, tricin),
organic
acids,
essential
oils
(monoterpenes
rosiridol,
rosaridin),
sugars,
proteins,
waxes,
mineral
compounds.
Tyrosol
Rosavin
Rosyridol
Liquid extract has tonic and antistress action. A clinical trial showed
significant effect for a golden rose extract in
doses 340-680 mg per day in 18-70-year-old
male and female patients with mild-tomoderate depression. Rhodiola is used as
adaptogen
Medical application:
Asthenic condition after suffering
nerve and systemic diseases,
neurasthenia, vegetative-vascular
dystonia, fatigue and .
Violae herba, EuPh
Viola tricolor- Heartsease, wild pansy
Viola arvensis- Field pansy
Violaceae
Constituents. Up to 0,3 % salicylic acid and its
derivatives as the methyl ester of violutoside,
further phenolic carboxylic acids such as caffeic,
p-coumaric, gentisic, etc.; 10 % micilage, made up
of Glc, Gal, Ara, Rham; up to 5 % tannins;
flavonoids ( rutin, violanthin, vitexin…);
carotenoids, violaxanthin, coumarins
(umbelliferone); small amounts of saponins
ascorbic acid.
violaxanthin
Medical application:
• Herbs have expectorant, diuretic, diaphoretic and anti-inflammation
action.
• Viola is the part of diuretic and chest (pectoral) mixes.
• In homeopathy fresh flowering plant is used for treatment of diathesis
in babies, skin problems and night bed wetting
Peoniae anomale herba
Peoniae anomale rhizomata et
radices
Paeonia anomala- Peony
Paeoniaceae
• Tincture of peony has
sedative effect on the
central nervous system
and used for treatment of
neurasthenia, insomnia
and neuroses.
• In folk medicinetreatment of
gastrointestinal system
diseases and epilepsy
Willow bark - Salicis cortex, EuPh
Salix acutifolia- Willow, Sallow, Osier
Salicaceae
Constituents. 0.5 to more than 11% phenolic
glycosides, the salicylates salicin, salicorin,
tremulacin, populin, fragilin, saliperoside,
triandrin, vimalin, picein, grandidentatin, and
3'and
4'-acetylsalicortin.
Aromatic
compounds: salidroside, vanillin, syringaaldehyde, syringin; salicylic, p-coumaric,
vanillic, syringic, p-hydroxybenzoic, caffeic
and ferulic acids; salicyl alcohol (saligenin).
Flavonoids (isoquercitrin, naringenin, chalcone
isosalipurposide, catechol), up to 20% tannin.
Medical application. For mild feverish colds and
infections, acute and chronic rheumatic disorders,
mild headaches, and pain caused by inflammation.
It is mainly salicin and the salicyl glycosides,
which form salicin after hydrolysis of the acyl
group that represent a salicyil acid pro-drug and
that
like
it
have
antipyretic,
analgesic/antirheumatic, and antiseptic actions.
Salicin is split by the intestinal flora into saligenin
and glucose. Saligenin is absorbed and oxidised in
the blood and the liver to salicylic acid.
Assalix® powers of the willow bark.
In gut and liver, its main active
ingredient salicin is converted to the
actual active ingredient salicylic acid.
Salicylic acid has an analgesic,
antipyretic and anti-inflammatory
effect.
salicin
saligenin
Rubi idaei fructus
Rubus idaeus- raspberry
Rosaceae
• From fruits we can do a
tincture with diaphoretic
and diuretic action which
can be used to treat
infection diseases and
high temperature.
• Syrup is very tasty and
used to correct the taste
of medicines
Cynarae folia , EuPh
Cynara scolymusArtichoke
Asteraceae
Constituents. Leaves contain phenolic acids:
coffeic, chlorogenic, neochlorogenic, 4-0caffeoyl-quinic and l-O-cofliyl-D-quinic
acids, and also cynarin (l,5-di-O-caffeoyl-Dquinic acid); tannins, flavonoids (luteolin
derivatives).
Cynarin
Medical application:
• Leaves stems are used to increase bile production, have
cholegogic, diuretic, hepatoprotective action. Induce the
metabolism of cholesterol and lipids in blood.
The presence of cynarin provides antisclerotic, cholagogue,
diuretic activity of artichoke extracts. Similar properties have
the phenolic acids of artichoke. They activate the bile
synthesis, increase diuresis, increase the volume of excreted
urine, regulate the functions of thyroid gland. Artichoke buds
are often used in cookery.
Filicis maris rhizomata
Dryopteris filix-mas- Male fern
Dryopteridaceae
Constituents.
The
major
active
substances are phloroglucinol derivatives:
aspidinol, albaspidin, filixic acid,
flavaspidic acid, filmaron, tannins, resins,
bitter, flavonoids, starch and essential oil.
The plant is poisonous!
Other types of fern can be collected by mistake-lady fern and ostrich fern
8-10 vascular bundle (Dryopteris felix-mas); 2 flatten vascular bundle
(Athyrium filix-femina); 2 (Matteuccia struthiopteris).
Uses. The rhizome is sometimes used for the treatment of a variety of
worm infestations. As the plant is poisonous, the treatment should be
conducted under doctor s supervision and the patient should be prepared
in a specific way (diet before administration, osmotic laxative in 30 min
after administration).
CANNABIS HERB - CANNABIS
HERBA
Cannabis — Cannabis sativa L., Fam.
Cannabaceae.
Synonym(s): Bhang, Dagga, Ganja, Hashish,
Indian hemp, Marihuana, Marijuana.
Constituents. Cannabis is the source of
phytocannabinoids — oxygen-containing C21
aromatic hydrocarbon compounds. At least 85
cannabinoids have been isolated from the
cannabis plant.