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Anthraquinones (Alexandrian > Indian)

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Anthraquinones (Alexandrian > Indian) Fruits belonging to other Families 1- Capsicum 7- Cubebs 2- Vanilla pods 8- Star Anise 3- Colocynth 9- Poppy capsule 10- Juniper berries 4- Senna pods 11- Pimento 5- Cassia pods 12- Cereals 6-Cocculus Capsicum (Chillies) 1- Capsicum minimum, Solanaceae. It contains a pungent principle: Capsaicin Oxidizing agents destroy the pungency of capsaicin It also contains fixed oil, red carotenoids and vit. C. used as: condiment, counter-irritant and for flatulent dyspepsia Capsaicin H N O MeO OH Counter-irritants Counter-irritants or external (topical) analgesics are: [Agents that are applied locally to produce an inflammatory reaction (cold, warmth, or itching) with the object of affecting another site usually adjacent to or underlying the irritated surface !] What is the precise mechanism of Capsaicin ? The precise mechanism of action of capsaicin is not fully understood !! What is the possible mechanism of capsaicin ? By depleting Substance P and preventing its accumulation. Substance P is a neurotransmitter that transmits pain impulses from the peripheral neurons to the central nervous system. Pain relief is experienced after Substance P is totally depleted. Other effects of capsaicin • Enhance energy metabolism in mammals , inducing thermogenesis (Thermogenesis is the heat produced from the burning of calories). • Reduce the levels of serum cholesterol. • Promote hair growth !!!. Counter-irritants [precautions] Precautions: 1- Keep out of eyes and mucous membranes. 2- Don’t apply to wounds or broken skin. 3- Don’t use for infants and children. 4- Don’t apply for large areas of the body. Vanilla pods 1- Carefully cured, full grown unripe fruits of Vanilla planifolia (Orchidaceae). It has a fragrant odour and taste Vanilla pods 6- Vanillin is the fragrant principle of Vanilla pods. 7- Uses: A- Perfumery. B- Confectionary. C- Falvouring agent. Colocynth (Bitter apple) 1- The unripe, full-grown fruits of Citrullus colocynthis, Cucurbitaceae deprived of its seeds and hard outer part of the pericarp (rind). 2- Spherical & yellow in colour. 3- Odourless with very bitter taste. 10- It contains: A- A purgative resin & a purgative alkaloid B- Eleven tetracyclic triterpenoidal glycosides (cucurbitacins). The most important is cucurbitacin E (a-elaterin). C- A crystalline alcohol (citrollol). 11- Used as cathartic and antitumour • Citrullus colocynthis is used to treat diabetes, since it may be able to induce insulin secretion from the pancreas after supplementation, while reducing blood glucose and improving lipid levels. • Used as cathartic • Even low doses (100mg, taken three times) of Citrullus colocynthis can cause diarrhea, while higher doses (1,500 mg) can cause colonic inflammation and rectal bleeding. These side-effects stop once supplementation is ceased. TAKE CARE ! Death has resulted from a dose of 1 1/2 teaspoonsful of the powdered Colocynth. Senna Pods • Remember: • 1- Cassia acutifolia (Alexandrian) & Cassia angustifolia (Indian or Tinnevelly), Leguminosae. • 2- Reniform (4-5 cm long). • 3- Odourless with bitter taste. Senna Pods -Constituents- • 4- It contains free and combined anthraquinones (Alexandrian > Indian). • 5- Sennoside A is the major component of these anthraquinones. • 6- Used as a mild laxative. • 7- It produces less griping than leaves . • The basic structure of all anthranoid laxatives is anthracene • Ring to which a hydroxyl or carbonyl function is substituted at C-9 • And hydroxy group at C-8 for the laxative function • Based on the group present at C-10 anthranoids can be divided • into three groups • Anthrones (H2) • Anthraquinones (=O) • dianthrones (other anthracene) Cassia Pods • Remember: • 1- Cassia fistula, Leguminosae. • 2- It comes from India. • 3- Cylindrical (40-70 cm long). • 4- Chocolate-brown in colour. • 5- Odourless and bitter. Cassia Pods -Constituents- • 6- It contains: • A- Anthraquinone derivatives e.g. rhein, sennidin-like compounds. • B- Sugars (50%). • 7- Uses: • A- A mild laxative. • B- In confection of Senna. Anthraquinones • Site of action: colonic mucosa. • Mechanism of action: • 1- Anthraquinone glycosides are directly transported to the colon. • 2- The glycosides are metabolised by the intestinal flora (formation of anthrones by reduction). • 3- Anthrones are the most active metabolites. • Important Notes: • 1- The most reactive anthrones are those having 1,8-dihydroxy groups. • 2- LD50 of pure sennosides A&B are: 4100 mg/kg (i.v), 5000 mg/kg (orally). • 3- LD50 of Senna extract: 172 mg/kg (i.v.) and 2500 mg/kg (orally). • 4- 20-30 % of people above 60 take laxatives once a week. 80% are taking Senna and related anthraquinones !. • 5- Laxative abuse syndrome (LAS) includes the following symptoms: • A- Loss of electrolytes. • B- Pathological changes in colonic mucosa. • C- Discoloration of the urine and faeces. • 6- Contraindications: • A- Children younger than 12 years. • B- In inflammatory intest. diseases. • C- For more than 8-10 days. • 7- Side effects of anthraquinones: • A- Pigmentation of colonic and rectal mucosa (reversible in 4- 12 months). • B- Anal fissures (irreversible, 7- 12% need surgery). • C- Damage of smooth muscles decreasing the peristalsis and leading finally to paralysis. • 8- Interactions: • A- Decrease absorption of oral drugs. • B- Increase the toxicity of cardenolides due to hypokalemia. • 9- Effects on Pregnancy: • Anthraquinones are safe and not teratogenic. • 10- Effects on Lactation: • Very small amounts are excreted in the milk, so should be given carefully !. Cocculus (Fishberries) • Remember: • 1- Anamirta paniculata, family: Menispermaceae. • the seed is very bitter. Cocculus (Fishberries) -Constituents- • 4- The seed contains a bitter substance (picrotoxin). • 5- Picrotoxin = C30H34O13. • 6- Picrotoxin = Picrotin (C15H18O7) + Picrotoxinin (C15 H16O6). • 7- The fruit contains 2 alkaloids: menispermine and p-menispermine. Cocculus (Fishberries) -Pharmacology & Uses- • 8- Picrotoxin is very toxic substance used in stupefying fish. • 9- Intravenously was used as antidote for barbiturates and narcotics. • 10- Picrotoxin is a CNS stimulant (GABA inhibitor) Tailed Pepper (Cubebs) • Remember: • 1- Piper cubeba, Piperaceae. • 2- From Indonesia. • 3- Contains v.o., resin, cubebic acid and cubebin (a lignan). • 4- Powder + 80 % H2SO4 crimson colour (due to cubebin). Tailed Pepper (Cubebs) • 5- Used for treatment of: • A- Chronic bronchitis. • B- Gonorrhoea. • Star Anise (Chinese Anise, Aniseed stars) • 1- Illicium verum, Illiciaceae. Star Anise • 2- From China. • 3- Consists of 5-7 seeded follicles. • 4- Odour and taste are exactly similar to Anise. • 5- Contains v.o. (anethole constitutes 80-90% of the oil). • 6- Carminative and flav. Agent in cough mixtures. Japanese star anise (shikimi or bastard fruits) • 1- An allied drug of star anise. • 2- Illicium religiosum, Illiciaceae. • 3- Cultivated near the Buddhist temples in Japan. • 4- Toxic because of sikimitoxin, sikimin and shikimic acid. TAKE CARE ! • Recently, many sesquiterpenes were isolated from Illicium species including I. verum. Some of them are convulsants ! • Poppy Capsule • 1- Nearly ripe capsule of Papaver somniferum, Papaveraceae. Poppy Capsule • 2- Globular or ovoid with sessile radiating stigma at the apex. • 3- Yellowish-brown, odourless and bitter. • 4- Contains morphine, codeine, narcotine, narceine and papaverine as major alkaloids together with meconic acid. Opiumm Fields Poppy Capsule • 5- No morphine in the seed. The oil of the seed is used by artists and for cooking. • 6- Meconic acid is used as a guide for detection of the alkaloids in opium and its preparations. • 7- Meconic acid is biologically inactive. Poppy Capsule -Uses- • 8- Morphine is a very potent analgesic. • 9- Codeine is the most powerful antitussive. • 10- Papaverine is a potent smooth muscle relaxant. • 11- Morphine and Codeine are narcotics causing addiction . Morphine -mechanism of action- • Morphine acts on the opiate receptors of the CNS in a similar manner to the endogenous enkephalins and endorphins increasing the pain tolerance. Tamarind pulp • 1- Tamarindus indica, family Leguminosae. • 2- From tropical Africa and India. • 3- Contains free organic acids (11- 16% acidity) and sugars (25-40%). • 4- Used in confection of Senna and as a mild laxative. Juniper berries • 1- Juniperous communis, family Cupressaceae. • 2- From Italy, Hungary, …etc. • 3- Contains v.o., sugars, resin and organic acids. • 4- Used as diuretic and urinary antiseptic (so, effective for kidney stones). Pimento (Jamaica Pepper) • 1- Pimenta officinalis, Myrtaceae. • 2- Contains tannins and v.o. (eugenol is the mojor constituent). • 3- Used as astringent, flavouring agent and stimulant. • It’s used as a substituent for Clove. Cereals • 1- Wheat: Triticum vulgare. • 2- Maize: Zea mays. • 3- Barley: Hordeum sativum. • All of them belong to family Graminae. • They contain protein, fat, sugars, amino acids and enzymes. Cereals -uses- • Uses: • 1- Production of grains and bran. • 2- Production of starch and germ oil. • 3- A source for vit. B and E. • 4- Bran is useful in atherosclerosis and used as slimming agent. • Bulk producer herbs a sense of fullness reducing appetite. • They are plant cell walls consisting of: polysaccharides (mainly cellulose, pectin, hemicellulose) + lignins + cutin + waxes + glycoproteins. • Effects of fibres: 1- decrease movement of food and acidic fluid from the stomach to the intestines helping people with duodenal ulcers by reducing the exposure of the small intestine to stomach acids. 2- reduce cholesterol and triglyceride levels. 3- protect against colon and breast cancer, gall bladder disease & ulcers (The National Cancer Institute recommends incorporating 30g of fibers into the daily diet) Examples of bulk producers: 1- Natural fibres 2- Semisynthetic polysaccarides (methylcellulose &carboxymethylcellulose) Types of Natural Fibres: 1- Insoluble (wheat and rice bran), fruits and vegetables, whole grains and psyllium (Plantago) 2- Soluble (beans, psyllium, corn, barley and fruits as mucilages, pectins and gums). .
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