Mehrere Mitteln

Phenol

ir.dut.ac.za/bitstream/handle/10321/938/Nsele_2012.pdf?sequence=1&isAllowed=y

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)

Catechin

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.

Tannin

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.

[Rob Peters]

The Lamiaceae. contain aromatic carbohydrates in the form of phenols, which have an antiseptic as well as an aromatic action.

Phenolengruppe

Alth. und andere Pflanzen enthalten Phenolsäure

Arbin. wird im Darm durch Bakterien zu Glucose und Hydrochinon umgesetzt

Ben. hat ähnliche Formel

Brachinus = Bombardierkäfer/verteidigt.x sich durch Spritzen von Hydrochinon gemischt mit Wasserstoffperoxid Coleoptera.x

Carbol-ac. Enthält Phenol

Kres. = Produkt aus Buchenteer/enthält 5% Phenol

Lamiaceae. enthalten Phenol

Pic-ac. = Trinitrophenolum

Tan-ac. = Phenol/= Gerbsäure

Vitis. R

Geschmacksträger. in Whisky (= rauchiger Geschmack).

Anthraquinone

Have laxative effects.

Found in Aloe (Asparagales)

Senna (Fabales),

Rhubarb (below),

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.

Benzoquinone

[Farokh Master]

Useful in cancer of uterus or as a matter of fact in any advanced cancer it helps me as a good palliative.

Quinone

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

Repertorium:

Kopf: Tumoren im Gehirn schnell wachsend

Gesicht: bläuliche Lippen

Bauch: Darmkrebs

Nieren: Degeneration/Polyzystische Nierendegeneration - stark ausgeprägt

Blase: Krebs - schmerzhaft, qualvoll

Prostata: Entzündet

Krebs

Atmung: Asthma, asthmatische Atmung bei Rauchern

Brust: Entzündete Mammae

Zyanose

Beschwerden der Aortenklappe - Stenose

Allgemeines: Konvulsionen epileptisch - traumatisch

unzureichende Funktion der Nebenniere

Vergleich. Enthalten in: Lawsonia (allergen/Hennatattoo) + Impatiens balsamica (= jewelweed/Geraniales);

Siehe: Farbstoffen

Allerlei: verursacht Anämie/absorbiert UV.

obtained by oxidizing naphthalene with Chr-ac

[D. Riley]

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

Diarrhea

Repertory:

Mind: Dreams – red colored (cars/flags)/being pursued/silly/remembered (throughout the day)/vivid

Dull mind/unclear thoughts when feverish

Worried

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”

Lethargic

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

Increased hunger

Abdominal cramps with nausea in the evening

Growling

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

Respiration:

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

Repertorium:

Bauch: Entzündete Gallenblase - chronisch

Brust: Schwäche im Herz + Lungen - Krebs - Atemnot

Allgemeines: Fettleibigkeit + unterentwickelten Genitalien

Repertory:

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

Day dreaming

Memory weak/forgets what is about to do/has just done

Feeling of being in trance/”As if in a dream”

Dull

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.

Nail-biting

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

Thirsty

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

Watery

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

Respiration:

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

Parabenzoquinonum

Repertorium:

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

Osteochondrosis

Osteogenesis imperfecta tarda

Schwäche nach Bluttransfusion

Nebenniereninsuffizienz

Resorcinum (Res) = C₆H₆O₂

Gebrauch: Taubheit/SCHWEIß/giddiness/salivation/convulsions;

Repertorium:

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.

Thymolum (Thymol)

Vorwort/Suchen Zeichen/Abkürzungen Impressum