Medicinal plants and medical plant materials that contain phenol compounds, simple phenols and their glycosides

2. Biosynthesis of phenolic compounds. 1. Phenolic compounds and their classification. 2. Biosynthesis of phenolic compounds. 3. MP and MPM containing simple phenols and phenolic glycosides

Phenols and Polyphenols 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, 2,6-Dimethoxybenzoquinone, phenol, pirocatechol C6-1 Alkilphenol Phenolic alcohol Phenolic aldehydes Phenolic acids p-cresol Saligenin Vanilin, Salicylic Gallic, salicylic C6-C2 Acetophenones,Tyrosine derivatives, Phenylacetate 3-Acetyl-6-methoxybenzaldehyde, Tyrosol, p-Hydroxyphenylacetic acid C6-C3 Hydroxycinnamic acids, Phenylpropenes, Coumarins, Isocoumarins, Chromones Caffeic, ferulic acids, Myristicin, Eugenol, Umbelliferone, aesculetin, Bergenon, Eugenin C6-C4 Naphthoquinones Juglone, Plumbagin

Phenolic compounds with one 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

Biosynthesis some natural compounds p-hydroxycinnamic (p-coumaric) acid Phenolic acid Combined forms of hydroxycinnamic acids reducing, dimerization polymerisation + malonat 3 molecules Acetophenones Phenilacetate acids oxidation Stilbens Lignans Lignins Phlavonoids Coumarins

Phenol Pyrocatechin Pyrogalol Phloroglucinol Hydroquinone Salicylic alcohol Salicylic aldehyde Salicine Salidroside

Physicochemical properties of phenol glycosides Phenolic glycosides are white crystal substances, soluble in water, ethanol and insoluble in ether or chloroform. They can hydrolyse while heated with mineral acids.

Obtaining Phenolic glycosides are extracted from plants with ethanol and methanol

Uvae ursi folia Uvae ursi cormi Arctostaphylos uva-ursi- Bearberry Family: Ericaceae BAS: leaves – Arbutin glicosides (8-12 %), methylarbutin, hydroquinon, galic, elagic acids, tannin (7-19 %), (+)-catechol, ursone and the flavone derivative quercetin.

Chemical constituents Arbutin Methylarbutin Arbutin Hydroquinon

Medicinal uses 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 diarrhoea composition

Vaccinium vitis idaea and Chimaphyla umbellate can be collected by mistake as Arctostaphylos uva-ursi

Vitis idaea folia Vitis idaea cormi Vaccinium vitis idaea- Lingonberry, cowberry, foxberry, mountain cranberry Family: Ericaceae Medicines have diuretic and antiseptic action and are used in treatment of cystitis, gonorrhea, pyelonephritis and urolithiasis. “Brusniver” has diuretic and nephrolitic action. Leaves of lingonberry contain 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

Rhodiolae roseae rhizomata et radices Rhodiola rosea- Golden root, roseroot, Aaron’s root Family: Crassulaceae Liquid extract has tonic and anti-stress 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-to-moderate depression

Viola is the part of diuretic and chest (pectoral) mixes. Violae herba Viola tricolor- Heartsease, wild pansy Viola arvensis- Field pansy Family: Violaceae Herb of heartsease has 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 Family: Paeoniaceae Tincture of peony has sedative effect on the central nervous system and used for treatment of neurasthenia, insomnia and neuroses. In folk medicine- treatment of gastrointestinal system diseases and epilepsy

Salicis cortex Salix acutifolia- long-leaved violet willow Family: Salicaceae Willow is employed as an anti-inflammatory in the treatment of rheumatism, arthritis and muscular pains due to the high content of salicylic acid

Rubi idaei fructus Rubus idaeus- raspberry Family: 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

Extract, tincture, Cynarin (increases bile flow), Chophytol. Cynarae folia et anthodia Cynara scolymus- Artichoke Family: Asteraceae Leaves and/or stems are used to increase bile production, have cholegogic, diuretic, hepatoprotective action. Induce the metabolism of cholesterol and lipids in blood. Extract, tincture, Cynarin (increases bile flow), Chophytol.

Filicis maris rhizomata Dryopteris filix-mas- Male fern Dryopteridaceae ( Family: Aspidiaceae) Extracts of male fern were traditionally employed as taenicides, particularly for tape worms, but safer drugs are now available and used in preference