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36 Cards in this Set
- Front
- Back
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Phenols classes 9
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• Simple Phenolics
• Phenylpropanoids • Coumarins • Naphthopuinones • Antraquinones • Flavanoids • Isoflavanoids • Lignans • Tannins |
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Phenols Properties:
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• Simple phenol does not occur in nature. However, there are many plant constituents which are made from phenolic building blocks.
• The phenol molecule is made up of an aromatic ring (benzene ring) with one hydrogen atom replaced by a hydroxyl group. • If there are 2 hydroxyl substitutions then there are 3 possible isomers of dihyroxybenzene: 1. Catechol 2.Resorcinol 3.Hydroquinone • And 3 possible trihydroxybenzenes 1. Pyrogallol 2.Benzenitriol 3.Phloroglucinol. • The hydroxyl group gives the molecule properties similar to an alcohol, and therefore they can be considered tertiary alcohols, but in addition they are weakly acidic, due to the unsaturated nucleus. • Most phenolics occur as glycosides, but these are hydrolysed in the body to the aglycone and the sugar moiety. |
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The categories of compounds which are included in Phenols are: 6
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Simple phenolic compounds and their glycosides
Tannins Coumarins and their glycosides Anthraquinones, naphthaquinones and their glycosides Flavones and flavonoid glycosides Anthocyanins and anthocyanidins |
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Simple Phenolics compounds are generally: Actions 11
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• Bactericidal
• Antiseptic • Anthelmintic/ vermicidal –this action is enhanced by alkyl groups present in eugenol and thymol • Vesicant - blistering agent • Keratolytic removes warts or bumps on skin • Anaesthetic • Precipitate/bind protein – reduces activity in the bloodstream • Reduce inflammation internally • Hepatotoxic in overdose • Isolated phenols inhibit leucocyte activity in common with all bactericidal compounds (combination with Myrrh or silicon-containing herbs (Equisetem, Tussilago farfara, Plantago lanceolata/major) which promote leucocytosis may be worth considering when formulating prescriptions. |
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Caffeic acid derivative containing plants:2
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• Artichoke (Cynara scolymus)
• Jave tea (Orthosiphon stamineus), • Rosemary (Rosmarinus off.) containing rosmarinic acid |
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Salicylic acid is found in the following glycisides: 3
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• Salicin (salicyl alcohol + glucose) in Salix sp., Populus sp, Viburnum prunifolium
• Populin (salicyl alcohol +benzoic acid +glucose) Populus tremula • Gaultherin (methyl salicylate + primaverose) Gaultheria, Salix, Filipendula ulmaria. |
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Salicylic acid Actions 15
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• a strong antiseptic externally (used to treat warts and verrucae)
• In the whole herb form it aids regeneration of the epithelium. • Potential gastric irritant, particularly in the isolated form, potentially causes gastric submucosal haemorrhaging. The esters and salts are less irritant. • Absorbed as sodium salicylate, possibly changed back into the acid in acid environments e.g. inflamed joints. • Antipyretic – increase peripheral blood flow and sweating, probably by acting on the thermogenic centre of the hypothalamus. This gives a rapid drop in body temperature, but in healthy individuals this is compensated back to the normal range. • Salicylates act directly on the hepatocytes to increase the volume and concentration of bile production. This also disinfects these cells. • Increase uric acid concentrations, therefore contra-indicated for gout. • Diuretic effect, suitable for treating oedema associated with joint disease. • Analgesic cf. Aspirin • Anti-inflammatory due to anti-prostaglandin and bradykinin action • Anti-coagulant effect can be used to reduce risk of thrombisis and to treat them as well. However, excessive doses can lead to capillary bleeding and hypothrombinaemia. • Uncouples oxidative phosphorylation, leads to increased catabolism and heat production and hypoglycaemic effect, all useful for diabetes. • Excretion via the urinary system makes salicylate a valuable urinary antiseptic, less marked with alkaline urine • Crosses the placental barrier. • Methyl salicylate can be used locally as a topical rubefacient, anti-inflammatory and counter-irritant. Found in oil of wintergreen and oil of birch. Note that it is also anti-coagulant( due to prostaglandin antagonism) and therefore should not be used on those taking warfarin or heparin. |
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Eugenol
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• Volatile Oil – Phenol
• Found in clove , Eugenia caryophyllum, cinnamon (Cinnamomum zylanicum) • Externally rubefacient, counter-irritant , anti-parasitc, analgesic. • Internally stimulates salivary secretion and gastric activity due to effects on taste and smell receptors and as an intestinal antispasmodic lower in the GIT. |
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Thymol
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• Volatile Oil – Phenol
• Found in the volatile oil component of thyme oil and other members of Labiate/ Lamiaceae family • Anti-fungal at concentrations of 1-2%: thyme oil contains 20-30%. • Oral and intestinal infections as an antiseptic • Anthelmintic, but should be administered in capsules as it is extremely irritating to the upper GIT in concentration, not in the whole herb form. • Very insoluble and inactivated by proteins. • Antiseptic and rubefacient properties useful in toothpaste and mouthwashes to treat gum disease. |
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Hydroquinone
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• Part of the aglycone of arbutin found in plants of Ericaceae and Roseaceae, antspetic for urinary tract as excreted by kidneys.
• Particularly active in Arctostaphylus uva-ursi. However, this herb is only active in alkaline urine. Follow alkaline diet or give bicarbonate of soda at same time. |
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Lignans Properties
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• are 3 dimensional compounds based on phenyl propane
• Often found in grains and pulses • Many have phytoestrogenic effects |
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Lignans Contraindication
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• Some lignans have significant toxicity
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Lignans Actions & Examples
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• Shizandrins in Scihzandra chinensis reverses liver cell destruction by inducing cytochrome P-450.
• Silymarin is a mixture of flavolignans found in Carduus marianum known to be hepatoprotective. • Linseed/Flaxseed (Linum usitatissimum) contains two oestrogenic lignans enterodiol and enterolactone in the seeds which are potent phytoestrogens. |
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Coumarins Properties 3
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• Can be discussed under volatile compounds and phenolic compounds
• They are found in a wide range of plant species and have diverse actions • They often occur as glucosides |
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Coumarins Contraindictaion 3
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• Furanocoumarins may produce a phototoxic reaction in people with normal skin. Found in Apiaceae and Rutaceae familes. Bergapten (a furanocoumarin) Apium graveolens
• Hogweed, one occurrence with parsley – Umbelliferae family – dermatitis due to a phototoxic reaction casued by furacoumarins and simultaneous exposure to sunlight. • Another one is psoralen from Ammi majus They have been used to treat vitiligo and psoriasis in conjunction with sunlight, but can lead to burns. |
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Coumarins Actions and Examples
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• Melilotus officinalis – Yellow sweet clover contains coumarins which metabolise to dicoumarol which act as an anticoagulant.
• Ammi visnaga for heart disease and asthma, • Hieracium pilosella brucellosis and renal problems, • Angelica archangelic GIT and respiratory complaintsa, • Galium odorata nervine for minor sleep disturbance and GIT |
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Properties of Essential Oil Families 14
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• Hydrocarbons/ terpenes, containing only carbon and hydrogen- Stimulant, decongestant, antiviral, anti –tumour
• Sesquiterpenes – Anti-inflammatory, anti-viral • Alcohols- generally antimicrobial and immunostimulating and tonic • Sesquiterpene alcohols – Anti inflammatory, anti-allergenic • Aldehydes - sedative, antiviral and antimicrobial • Aromatic aldehydes - spasmolytic • Ketones - mucolytic, cicatrisant(helps formation of scar tissue). Some are neurotoxic and abortifacient in high dose. • Phenols - strongly antimicrobial, immune stimulating; dermal and mucous membrane irritants. • Phenyl methyl ethers/ phenolic ethers • Oxides - expectorant and stimulent • Esters - sedative and antispasmodic, antifungal • Acids - soothing to the skin • Coumarins – UV sensitising and antimicrobial • Sesquiterpene lactones mucolytic, immune stimulating |
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EO Monterpenes hydrocarbons examples and actions
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• Stimulant, decongestant, antiviral, anti –tumour
• Pinene Coriander, Cypress, Eucalyptus globulus, Fennel, Pine, Rosemary, Black Pepper, Juniper, Cajeput (pinene is thought to be the most abundant hydrocarbon in nature). – skin irritant and can cause kidney damage • Limonene Bergamot, Fennel, Lemon, Neroli, Orange, Black Pepper, Pine, - expectorant sedative, antitumour and a solvent for gall stones |
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EO Sesquiterpenes
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Anti-inflammatory, anti-viral
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EO Alcohols
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generally antimicrobial and immunostimulating and tonic
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EO Sesquiterpene alcohols
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Anti inflammatory, anti-allergenic
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EO Aldehydes
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sedative, antiviral and antimicrobial
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EO Aromatic aldehydes
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spasmolytic
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EO Ketones
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mucolytic, cicatrisant(helps formation of scar tissue). Some are neurotoxic and abortifacient in high dose.
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EO Phenols
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strongly antimicrobial, immune stimulating; dermal and mucous membrane irritants.
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EO Oxides
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expectorant and stimulant
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EO Esters
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sedative and antispasmodic, antifungal
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EO Coumarins
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UV sensitising and antimicrobial
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EO Sesquiterpene lactones
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mucolytic, immune stimulating
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EO Sesquiterpenes example
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(Cham)azulene German chamomile, Roman chamomile.
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EO Alcohol example
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Citronellol Geranium, Palmarosa.
Geraniol Palmarosa, Rose, |
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eo Sesquiterpene Alcohol example
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Santalol (Cardiotonic, immune stimulant/ anti-infectious for UTIs) Sandalwood
Carotol (Liver cell regenerator) Carrot seed |
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EO Acid example
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febrifuges and are hypotensive. They are calming on an emotional level.
Benzoic acid Benzoin, |
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EO Ketones example
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Camphor/Borneone [Camphor, Mugwort, Spike Lavender], Cinnamon, Rosemary
Carvone (Cholagogue, choloretic) [Caraway, Spearmint, Dill], Peppermint Can be highly toxic treat with care |
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EO Esters example
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Lavandulyl acetate Lavender
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EO Coumarins example
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Furanocoumarins (Bergaptene, Bergamotine, Angelicine) are photosensitising which means that they sensitise the skin to U.V.
Coumarin Lavender |
