Radikalfängereigenschaften, antisklerotische, lipidsenkende, antihypertensive und antikanzerogene Wirkungen
[Nhlanhla Wiseman Nsele]
The term phenolic compound embraces a wide range of plant substances which possess in common an aromatic ring bearing one or more hydroxyl substitutes (Harbone, 1984).
They tend to be water-soluble, since they most frequently occur combined with sugar as glycosides and are usually located in the cell vacuole. Among the natural phenolic compounds, of which several structures are known, flavonoids form the largest group, but simple monocyclic phenols, phenolpropanoids and phenolic quinines all exist in considerable numbers (Harbone, 1984). In many cases, these substances serve as defence mechanisms of plants against predation by microorganisms, insects and herbivores (Marjorie, 1999).
Some such as terpenoids give plants their odours; others such as tannins and quinines are responsible for plant pigment. Aromatic compounds are responsible for plant flavour.
Useful antimicrobial phytochemicals can be divided into several categories, described below.
Simple phenols and phenolic acids
Phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl functional group (-OH) attached to an aromatic hydrocarbon group.
The simplest of the class is phenol (C6H5OH). Some phenols are germicidal and are used in formulating disinfectants. Phenol, the parent compound, is used as a disinfectant and for chemical synthesis.
Coffee is particularly rich in bound phenolic acids, such as caffeic acid, ferulic acid, and P-coumaric acid (Nardini et al., 2002).
Quince and Aloe ferox both have phenolic acids
Spices are known to significantly contribute to the flavour, taste, and medicinal properties of food because of phenolics. Most spices contain phenolic acids (tannic, gallic, caffeic, cinnamic, chlorogenic, ferulic and vanillic acids). A high amount of tannic and gallic acids are found in black mustard and clove.
Caffeic, chlorogenic and ferulic acids are found in a high concentration in cumin.
Vanillic and cinnamic acids are found in onion seeds (Nigella sativa).
Salicylic acid is a phenolic compound which is a precursor compound to aspirin (Montenegro et al., 2009).
Aspirin (acetylsalicylic acid) is still the most commonly used salicylate. After oral administration as an aqueous solution, aspirin is rapidly absorbed at the low pH of the stomach. And can cause bleeding of stomach. Less rapid absorption is observed with other formulations due to the rate limiting step of tablet disintegration - this latter factor being maximal in alkaline pH. The rate of aspirin absorption is dependent not only on the formulation but also on the rate of gastric emptying. Aspirin absorption follows first-order kinetics with an absorption half-life ranging from five to sixteen minutes. Hydrolysis of aspirin to salicylic acid by nonspecific esterases occurs in the liver and, to a lesser extent, the stomach so that only 68% of the dose reaches the systemic circulation as aspirin. Both aspirin and salicylic acid are bound to serum albumin (aspirin being capable of irreversibly acetylating many proteins), and both are distributed in the synovial cavity, central nervous system, and saliva.
The serum half-life of aspirin is approximately 20 minutes. The fall in aspirin concentration is associated with a rapid rise in salicylic acid concentration.
Salicylic acid is renally excreted in part unchanged and the rate of elimination is influenced by urinary pH, the presence of organic acids, and the urinary flow rate.
Benefit of phenols
Phenolic acids are plant metabolites widely spread throughout the plant kingdom.
Phenolic compounds are essential for the growth and reproduction of plants, and are produced as a response for defending injured plants against pathogens.
Recent interest in phenolic acids stems from their potential protective role, through ingestion of fruits and vegetables, against oxidative damage diseases (coronary heart disease, stroke, and cancers).
The absorption and bioavailability of phenolics in humans are controversial. Data on these aspects of phenolics are scarce and merely highlight the need for extensive investigations of the handling of phenolics by the gastrointestinal tract and their subsequent absorption and metabolism.
Plant phenolic compounds are diverse in structure but are characterised by hydroxylated aromatic rings (e.g. flavan-3-ols).
They are categorised as secondary metabolites, and their function in plants is often poorly understood. Many plant phenolic compounds are polymerised into larger molecules such as the proanthocyanidins and lignins. Furthermore, phenolic acids may occur in food plants as esters or glycosides conjugated with other natural compounds such as flavonoids, alcohols, hydroxyfatty acids, sterols, and glucosides.
Some herbs such as tarragon and thyme both contain caffeic acid, which is effective against bacteria, viruses and fungi (Marjorie, 1999).
Catechol and pyrogallol both are hydroxylated phenols, shown to be toxic against microorganisms (Marjorie, 1999). Some authors have found that more highly oxidized
phenols are more inhibitory (Scalbert, 1991). The mechanisms thought to be responsible for phenolic toxicity to micro-organisms include enzyme inhibition by the oxidized compounds, possibly through reaction with sulhydryl groups or through more non-specific interactions with the proteins (Mason and Wasserman, 1987).
FLAVONES, FLAVONOIDS AND FLAVONOLS
Flavones are phenolic structures containing one carbonyl group. The addition of a 3-hydroxyl group yields a flavonol.
Flavonoids are hydroxylated phenolic compounds but occur as a C6 - C3 unit linked to an aromatic ring (Marjorie, 1999). They are known to be synthesised by plants in response to microbial infection (Dixon and Lamb, 1983). They have been found in vitro to be effective antimicrobial substances against a wide range of micro-organisms. Their activity is probably due to their ability to complex with bacterial cell walls, as described for quinines. More lipophilic flavonoids may also disrupt microbial cell membranes (Marjorie, 1999).
Catechins, the most reduced form of the C3 unit of flavonoid compound have been found to be present in oolong green tea (Marjorie, 1999).
It was found some time ago that teas exerted antimicrobial activity (Marjorie, 1999) and that they contain a mixture of catechin compounds. These compounds inhibited in vitro Vibrio cholera 01 (Borris, 1996) and Streptococcus mutans (Batista et al.,1994).There is a considerable range of flavonol glycosides in plants. More than 200 different glycosides of Quercetin alone have been described, of which by far the most common is quercetin 3 rutinose, known as rutin (Harborne, 1984).
Flavones occur as glycosides but the range of different glycosides is less than in the case of flavonols.
More than one study has found that flavone derivatives are inhibitory to respiratory syncytial virus (RSV) (Barnard et al., 1993/Kaul et al .1985).
Flavone is one of the main groups of flavonoids, and the most widespread flavone is quercetin serves as the backbone for other flavonoids, and is the most active of
the flavonoids (Ikan, 1991). Many medicinal plants have significant quercetin content.
Quercetin behaves like auxins in stimulating the germination of wheat seeds. The possible function of this colouring matter in insect-pollinated flowers and edible fruits is to make these organs more conspicuous in order to aid seed dispersion by animals (Ikan, 1991).
Small quantities of quercetin may act as cardiac stimulants. It is used to strengthen weak capillary blood vessels (Ikan, 1991)
Flavonoids are able to join together to form other flavonoids e.g. catechin.
Catechins are monomeric flavonoids which, joined together, can form new compounds; it is a yellowish amorphous solid. There are different types of catechins and they bond together in various ways to form different compounds with very different characteristics. Two catechins joined togetherare called dimer and three catechins bonded together a trimer and so on up to oligomers and polymers. These new compounds are called proanthocyanidis, or condensed tannins.
Oligomeric proanthocyanidins are oligomeric flavonoids. These molecules are found in the bark of pine trees (Wijesekera, 1991).
Catechin easily binds to proteins, blocking bacteria from adhering to cell walls and thereby disrupting their ability to destroy them.
It decreases cholesterol level in blood and prevents LDL cholesterol caused by oxidation, which prevents narrowing of blood vessels caused by the build-up of LDL cholesterol (Bishop et al., 2005)
Catechin is a useful component for the prevention and treatment of substances that suppresses the immunesystem (Wijesekera, 1991).
It fights bacteria and viruses and prevents influenza. It is an antioxidant.
Tannins by definition have the ability to react with protein, forming stable water insoluble co-polymers (Harbone, 1998). They are of plant origin, which through their ability to cross-link with protein are capable of transforming raw animal skin into leather. Plant tissues high in tannin content impart an astringent taste, which acts as
a deterrent to most feeders. Tannins are divided into two groups, hydrolysable and condensed tannins. Hydrolysable tannins are based on gallic acid, usually as multiple esters with D-glucose while the condensed tannins are derived from flavonoid monomers (Marjorie, 1999).
Tannins may be formed by polymerisation of quinone units. Many human physiological activities, such as stimulation of phagocytic cells, host mediated tumour activity and a wide range of anti-infective actions have been assigned to tannins (Haslam, 1996). Their mode of antibacterial action is related to their ability to inactivate microbial adhesions, enzymes and cell envelope transport proteins. They also form complexes with polysaccharides. There is also evidence for direct inactivation of micro-organisms. Condensed tannins have been determined to bind cell wall of bacteria, preventing growth and protease activity (Jones et al 1994).
Tannins consist mainly of gallic acid residues that are linked to glucose via glycosidic bonds.
The Lamiaceae. contain aromatic carbohydrates in the form of phenols, which have an antiseptic as well as an aromatic action.
Alth. und andere Pflanzen enthalten Phenolsäure
Arbin. wird im Darm durch Bakterien zu Glucose und Hydrochinon umgesetzt
Ben. hat ähnliche Formel
Carbol-ac. Enthält Phenol
Kres. = Produkt aus Buchenteer/enthält 5% Phenol
Lamiaceae. enthalten Phenol
Pic-ac. = Trinitrophenolum
Tan-ac. = Phenol/= Gerbsäure
Geschmacksträger. in Whisky (= rauchiger Geschmack).
Have laxative effects.
Found in Aloe (Asparagales)
Cascara buckthorn (Rosales).
The family sensation is of a dry and tickling irritation. The mental state can be irritable or weary of life and indifferent.
Theme: Oppression: Irritation vs. Indifference.
Useful in cancer of uterus or as a matter of fact in any advanced cancer it helps me as a good palliative.
From Wikipedia, the free encyclopedia
Not to be confused with quinine.
A quinone is a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds," resulting in "a fully conjugated cyclic dione structure." The class includes some heterocyclic compounds.
The prototypical member of the class are 1,4-benzoquinone or cyclohexadienedione, often called simply quinone (whence the name of the class). Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.
Quinones are oxidised derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. (Quinones are conjugated but not aromatic). Quinones are electrophilic acceptors stabilised by conjugation. Depending on the quinone and the site of reduction, reduction can either rearomatise the compound or break the conjugation. Conjugate addition nearly always breaks the conjugation.
Chinone sind eine große und wichtige Gruppe organischer Verbindungen, die als Oxidationsprodukte von Aromaten, insbesondere von Phenolen, aufgefasst werden können. Der Name Chinon leitet sich von der Chinasäure ab, deren Oxidation u. a. zu 1,4-Benzochinon führt. Chinone sind Benzolderivate, in denen unter Aufhebung der Aromatizität des Ringes an zwei Kohlenstoffatomen die Substituenten durch doppelbindigen Sauerstoff ersetzt sind. Stoffe, deren chemische Struktur ein Chinon-Element enthält, nennt man chinoid, das Strukturelement selbst chinoides System.
Die Reduktion von Chinonen liefert die zugehörigen Phenole, die auch Chinole genannt werden.
Die durchweg farbigen Chinone sind Oxidationsmittel, deren Redoxpotential durch Substituenten (Halogen-, Cyan-, Alkyl-, Hydroxy-Gruppen) deutlich verändert wird. Man unterscheidet 1,2-(ortho-)Chinonen (z. B. PQQ) und 1,4-(para-)Chinonen (z. B. Anthrachinon).
Formaler Ersatz des Sauerstoffs einer chinoiden Carbonyl-Gruppe durch =NH, =NOH, =N2 oder =CH2 führt zu Chinoniminen, Chinonoximen, Chinondiaziden und Chinonmethiden. Synonym bezeichnet Chinon die Verbindung 1,4-Benzochinon, die durch Oxidation aus 1,4-Dihydroxybenzol (Hydrochinon) entsteht.
Unter den Chinonen finden sich viele Gifte, aber auch ein breites Spektrum lebensnotwendiger Vitalstoffe, z. B. Ubichinone, Phyllochinone, PQQ.
Bekannte Chinone sind:
die Ubichinone als Elektronenüberträger in der Atmungskette
die Plastochinone bei der Photosynthese
die K-Vitamine (Phyllochinon, Menachinon)
das Pyrrolochinolinchinon (PQQ)
das Tryptophantryptophylchinon (TQQ)
das Dichlordicyanochinon (DDQ)
die Hydroxynaphthochinone (in Henna und Walnüssen)
Echinochrom A, Adrenochrom, Dopachrom
Chinone werden auch in den Wehrsekreten von Insekten: gefunden.
Quinones contain aromatic rings (Marjorie, 1999). They are ubiquitous in nature and are characteristically highly reactive. Although they are widely distributed and exhibit great structural variation, they make relatively little contribution to colour in higher plants (Harbone, 1984). They are commonly present in bark, roots, or else in tissues (such as leaves) where their colours are masked by other pigments. These compounds, being coloured, are responsible for the browning reaction in cut or injured fruits and vegetables. They are also an intermediate in the melanin synthesis pathway of the human skin. Quinones provide a source of stable free radicals and are known to complex irreversibly with nucleophilic amino acids in proteins (Stern et al., 1996), often leading to inactivation of protein and loss of function. For that reason, the potential range of quinine antimicrobial effect is great. Probable targets in the microbial cell are surface-exposed adhesions, cell wall polypeptides, and membrane-bound enzymes (Marjorie, 1999).
Quinones may also render substrates unavailable to the microorganisms.
One example of a quinone is p-benzoquinone.
Naphthoquinone = Naphtachinon (Naphtoc) = Lawsone/= natural orange/= Juglon-ähnlich (= Teil Jug-r)/C10H6O2
Kopf: Tumoren im Gehirn schnell wachsend
Gesicht: bläuliche Lippen
Nieren: Degeneration/Polyzystische Nierendegeneration - stark ausgeprägt
Blase: Krebs - schmerzhaft, qualvoll
Atmung: Asthma, asthmatische Atmung bei Rauchern
Brust: Entzündete Mammae
Beschwerden der Aortenklappe - Stenose
Allgemeines: Konvulsionen epileptisch - traumatisch
unzureichende Funktion der Nebenniere
Vergleich. Enthalten in: Lawsonia (allergen/Hennatattoo) + Impatiens balsamica (= jewelweed/Geraniales);
Allerlei: verursacht Anämie/absorbiert UV.
obtained by oxidizing naphthalene with Chr-ac
Important Proving Symptoms and Themes Noted by the Investigators
Affecting sleep patterns (easy falling asleep/restless and increased remembrance of dreams)
Headache “Like a band”. Improvement of premenstrual abdominal distension and swelling (limbs/premenstrual spotting)/waking to urinate
Mind: Dreams – red colored (cars/flags)/being pursued/silly/remembered (throughout the day)/vivid
Dull mind/unclear thoughts when feverish
Feeling smart, confident, intelligent
Talking in sleep person awakens without remembering
Waking with weeping after a dream
Anxious (and apprehension/”As if time moved too slowly)
Generalities: Desires: ice-cold things/salad/chocolate;
Feeling shaky and jittery “As from a reaction to diet medication”
Premenstrual symptoms decrease: less bloating and swelling
Engorgement of blood vessels
Vertigo: Dizzy after eating, with a relaxed and floating sensation
Head: Pain – stitching/sharp and stabbing in forehead/sharp shooting on r. vertex/piercing/pressing “Like a cap” is dull constant pain/raging “Like a vise” on waking/
stitching in forehead/sharp, shooting at vertex/pressing “Like a cap”/dull/piercing
Eye: Uncontrollable twitching of r. lid
Ear: Wax bright yellow
Hearing: “As if plugged”/”As if sound is less perceived”
Nose: Increased mucus in postnasal passages
Tickling internal leads to sneezing
Face: Cold sore in the r. corner of mouth
Mouth: Aphthae on r. side of mouth
Soreness on the tongue like a swollen taste bud or “As from biting”
Biting the inside of the mouth when talking.
Teeth: Tooth sensitive to hot and cold
Throat: Dryness internal < at bedtime
Euphoric feeling in throat “As if tingling”
Scratchy sensation of throat with postnasal mucus
Clears throat in evening
Stomach: Thinking of food causes desire to gag
Abdominal cramps with nausea in the evening
Abdomen: “As if a hole like an empty cavity”
Pain - dull above the umbilicus/cramping with nausea and cold perspiration/aching followed by bowel movements
Swelling and distended before menses
Rectum: Feeling of incomplete evacuation after a bowel movement
Flatus with involuntary stool
Diarrhea on waking, or causes rushing to the toilet
Intense itching in the anus
Stool: Diarrhea with foul-smelling stool
Stool: starts solid and becomes more liquid.
Rushing to the toilet with runny, loose stools
Female organs: Spotting preceding menstrual flow
Menses starts and suddenly
Cramping before or during menses
Speech and Voice: Hoarse towards evening
Chest: Breast swollen for menses and painful/tender
Back: “Neck as if swollen” with dullness of the mind.
Neck and back - left-sided tightness ext. to hamstrings and calves
Limbs: Stiffness and aching in ankle and elbow joints
Muscles tight l. sided ext. from neck and back to hamstrings and calves
Swollen hand/fingers/ankle before menses
Pain – cramp in l. calf on waking at night
Sleep: Falling asleep early in the evening
Restless with tossing and turning
Getting hot during sleep and throwing off the covers
Need to wake during the night to urinate
Sleeps on the back
Skin: Moles on neck
Picricum acidum (Pic-ac) = TNP/= Trinirophenol/= C6H3N3O7
Hydroquinone (Hydroq) = Hydrochinon/= Phenol
Bauch: Entzündete Gallenblase - chronisch
Brust: Schwäche im Herz + Lungen - Krebs - Atemnot
Allgemeines: Fettleibigkeit + unterentwickelten Genitalien
Important Proving Symptoms and Themes Noted by the Investigators
Restless or frequent waking
Eczema (dry/flaky/< moisture) of the (r.) hand/fingers,
Mind: Active thoughts causes sleeplessness
Absence of thoughts - when alone/driving - startles when awareness returns
Vacancy of thought/must force the mind to concentrate while driving
Memory weak/forgets what is about to do/has just done
Feeling of being in trance/”As if in a dream”
Dreams – vivid/fragments/nightmares (darkness/desolation/bleakness/destruction/imprisonment/among strangers/violence/being whipped)
“As if isolated or separated”
Delusions – friends looking down
Confidence in self
Strong irritability when skin lightly stroked/touched.
Generalities: Physical energy increased and sleep decreased
Food: Desires: cold cereal/meat (hamburger with cheese)
Flushes of heat during the night requiring blankets removed and replaced several times
Head: Chronic daily pain – “As if a band”/pressing
Pain - sudden/sinus headache during menses
Eye: Photophobia during daytime causing squinting
Vision: Foggy and incoordinated
Nose: Epistaxis r. sided with bright blood on blowing the nose
Coryza r. sided
Postnasal bloody discharge
Mouth: Dry with thirst
Sore gums and tongue
Tongue – indented/”As if swollen”/”As if too large”
Teeth: Pain – stitching while eating
Throat: Eruptions – “Like boils” on opposite sides of neck in same size and location
External throat: “As if swollen”/”As if burning” in trachea after running a short distance.
Stomach: Appetite - decreased during pain/lost after few bites
“As if full”
Heartburn – daily/morning acid
Abdomen: Distended - before menses/in the afternoon
Pain – clutching/cramping ext. middle of back
Pain - before/during menses
Rectum: Evacuation feels incomplete after straining
Diarrhea - urgent and sudden/after eating/anticipatory
Flatus [and diarrhea (before a sports competition)]
Pain - cramping before stool
Stool: Sudden and explosive
Female Genitalia: Bloody discharge preceding onset of menses
Menses 1. stops suddenly, followed by swollen fingers/face/breasts; 2. Menses begins again shortly thereafter
Painful, aching menstrual cramps
Speech and Voice: hoarse and husky
Clearing throat improves hoarseness that prevented speech
Back: Abdominal cramps ext. thoracic region
Lower back stiff on motion after sitting > heat
Limbs: Stiff > heat
Eczema - eruptions on fingers/(palm) hand/painful: stinging/burning/itching/desquamating/only r. hand < with moisture/flaky/white/dry
Fingers sensitive (pressure)/shriveled/appearing small with eczema
Perspiration in palm of hand with eczema
Itchy red rash in hollow of knee
Dropping objects “As from lack of hand-eye coordination
Sleep: Falling asleep difficult (after waking)
Perspiration during sleep
Restless/tossing and turning/unrefreshing
Sleepless from thoughts
Frequent sudden waking
Perspiration: During sleep matting hair and soaks the pillow
Skin: Eczema see Limbs
Allerlei: In hautaufhellende Cremes gebraucht
Gemüt: Eigensinnig, starr-/dickköpfig (Kinder)
Streitsüchtig (bei Alkoholikern)
Ungehorsam (Kindern)/Verhaltensstörungen (Kindern)
Auge: Degenerierte Netzhaut
Bauch: Leber entzündet
Verletzungen des Milzes
Nieren: Addison Syndrom
Atmung: Atemnot, Dyspnoe, erschwertes Atmen
Brust: Entzündete Endokard und Myokard
Glieder: Entzündet Gelenke - wandernd
Allgemeines: Multiple Sklerose
Osteogenesis imperfecta tarda
Schwäche nach Bluttransfusion
Resorcinum (Res) = C6H6O2
Magen: Erbricht während Durchfall
Rektum: Cholera infantum
Uitwendige toepassing als antiseptisch en desinfecterend middel. Chronische huidaandoeningen: 5 - 10% in zalf bij psoriasis, hidradenitis suppurativa, eczeem.
Zelfzorg anti-Acne-middelen: 2%.
Weak, watery solutions of resorcinol (25 to 35 g/kg) allay itching in erythematous eczema. A 2% solution as a spray in hay fever/whooping cough (0.6 ml of the 2% solution internally).
As an anti-dandruff agent in shampoo or in sunscreen cosmetics. It has also been employed in the treatment of gastric ulcers in doses of 125 to 250 mg in pills, and is said to be analgesic and haemostatic in its action.