Thursday 31 January 2013

Materia medica and Bioactive compounds. Kader Kochi


Chemical constituents present in crude vegetable or animal parts responsible for biological activity are called bioactive compounds.


Primary metabolites of plants are essential for growth and daily functioning of the plants. 

They includecarbohydrates, amino acids, nucleotides, fatty acids, steroids and lipids.

The secondary metabolites are waste material of plants include, alkaloids, glycosides, non-protein amino acids, and amines. 

They are essential for defensive functions especially from mushroom, insects and herbivores animals. 

They are present in small quantities. 

Generally, they are present in the storage organs of the plants, especially in seeds and roots, and less in leaves, bark, wood or other plant parts.

Plants produce smell, nectar, and color for attraction,survival, and defensive purpose. 

The strength of bioactive principle of one plant may vary on different soil.

Bioactive compounds  

Alkaloids
Gum
Waxes
Neutral principles

Glycosides
Resins
Saponins
Lignans

Fats & Fixed oils
Gum resins
Tannins
Isoflavones

Volatile oils
Oleoresins
Balsams



Alkaloids

Alkaloids are Nitrogen-containing compound. 
15% of plants produce alkaloids. 
Total 12,000 alkaloids have been identified. 
The name alkaloid is derived from Arabic al-qalwi,means ashes of plants. 
These are final products of protein metabolism in plants as urea in mammals. 
Besides the nitrogen, it contain carbon, hydrogen, oxygen, sulphur, chlorine, bromine and phosphorus. 
Most of alkaloids contain oxygen, but nicotine and coniine are oxygen free. 
Colored alkaloids include berberine and sanguinarine.They are mostly solids and bitter in taste.

Solid alkaloids include atropine, hyosine, quinine, strychnine, codeine and theobaine.

Liquid alkaloids include nicotine, lobeline and pilocarpine.

Alkaloids are classified on basis of similarity of the carbon skeleton and its biogenetic precursor

True alkaloidsare that contain Nitrogen atoms in the heterocyclic position

Pyrrolidine
Bellaradine (belladonna), hygrine (coca,withania), nicotine, stachydrine (millefolium, alfalfa)

Pyrrolizidine
Symphytine, crotallaria, eupatorium purpurium, tussilago, senecionine ( hepatotoxic )

Pyridine
Trigonelline, ricinin, arecolin, nicotinic acid (belladonna, tobacco)

Piperidine

Trognelline, coniine, arecoine, lobeline, pomegranatine(root), nicotine, piperine (black pepper), anabasine   

Tropane
Scopolamine, atropine (anticholinergics), cocaine (stimulant), dubosia, and dioscorine. 
Tropane has anticholinergic, analgesic, anti secretary properties. 
It is smooth muscle relaxant.

Quinoline
Quinine and quinidine ( cinchona, angustura)

Isoquinoline
 Argemonine,  berberine, celandine, hydrastine, emetine, morphine, papaverine, narcine,  and sanguinarine
 Isoquinoline has antiviral, anti cancerous, bone marrow stimulating properties.

Quinolizidine
Spartine, yohimbine, baptisine and lupine.

Indol
Strychnine, reserpine, ergotamine, physostigmine, gelsemine, vincristine, aspidospermine,  bufotoxin, and yohimbinum

Imidazol
Pilocarpine

Steroidal alkaloids

Conicine, withanine, solanidine (shoots of potato), veratrum, kurichi, and arginine

Purine, methyl xantine
Caffeine, theophylline (tea, coffea, cola nuts), thiobromine (coaco)
It can cause testicular degeneration in male, and reduce acne in young

Others
Choline, neurine, and muscharine


 Proto alkaloids 
      These compounds are originated from amino acids and contain nitrogen atoms in the side chain.
   
Example includes mescaline, adrenaline, and ephedrine.

Pseudo alkaloids

These nitrogen contain compounds are formed by transamination from fat and carbohydrate, not derived from amino acid. 

The examples include ephedrine, colchicine and aconitine.

Biogenetic precursors of alkaloids are amino acids include ornithine, lysine, phenylalanine, tyrosine, histidine, aspartic acid (nicotine) and anthranilic acid. 

Many individual names are formed by adding the suffix "ine" to the species. 
Suffixes "idine", "anine", "aline", "inine" etc are added if several alkaloids are extracted from one plant.

Milestone of discovery of alkaloids

Friedrich serturner, the German chemist first isolated morphine from poppy in 1804

Morphine     (1804)
Atropine  (1819)
Coniine        (1827)
Sparteine              (1851)

Xanthine      (1817)
Quinine   (1820)
Nicotine       (1828)
Cocaine                (1860)

Strychinine  (1818)
Caffeine   (1820)
Cholchicine  (1833)
Synthetic coniine   (1886)

Glycosides
Glycosides are non-nitrogenous compounds. 
They give two portions on hydrolysis by enzymes and acids. 

Sugar portion is glycone and non-sugar portion is aglycone. 
If glycone is glucose, they are called as glucosides.

The main groups of glycosides are

Alcoholic
glycosides
Examples include salicin found in salix nigra.
They have antipyretic and anti-inflammatory action.


Cardiac
glycosides
They are calcium promoters in lower dose. So strong contraction, prolonged diastole and increased venous return are developed. 
Examples include steroids found in scilla, digitalis, oleander, strophanthus, and convallaria.


Anthraquinone
glycosides
They are aglycone and have laxative effect. Antraquinine can promote water & electrolyte secretion and peristalsis. 
Example include rumex and rheum


Coumarin
glycosides
Examples include coumarin found in psoralea leaves.
 They can dilate coronary vessel and inhibit calcium channel (paralysis).


Cyanogenic
glycosides

Examples include amygdalin found in cherries, rose, sambucus, lauroceracus, plums, apple seeds, apricot seed, peach, yucca, bamboo shoots, flax seeds, mushroom, cassava, and almonds. 
They have some anticancer properties. 
Cyanides can promote hypothyroidism.


Flavonoids
glycosides
They have antioxidant, anti-inflammatory and anti neoplastic (phytoestrogen) properties. 
They decrease capillary fragility. 
Examples include quercitrin, rutin, and hesperidin .
Common causes of chronic inflammation are excess of co2 and salt; lack of O2, enzymes and vitamin E; electron loss, and radiation.
Vitamin E present in peanut, selenium and bran rice.


Phenolic
glycosides
They have urinary antiseptic property. 
They found in uva-ursi. 
Example includes arbutin.  
Phenols derivatives are hypericum, quercus and heracleum. 
They have anti vitilgo properties.


Saponin
glycosides
They are good expectorant, anti-inflammatory, immune modulator and anti neoplastic.
Examples include liquorice.

Steroid saponin is diosxin found in dioscorea. 
It can cause hepatitis and hyper pigmentation.(liliacea)


Triterpen
glycosides


Example includes triterpen found in ginseng.
Stevia
glycosides

Example includes stevioside and rebaudioside found in stevia plant.


Thio
glycosides 
They are sulphur contain compound. 
Examples include singrin found in black mustard and sinalbin found in white mustard. Glucosinolates can inhibit procarcinogens in liver. They can prevent hyperthyroidism.


Fixed oils

They are the esters of higher fatty acids. 
They form soaps with alkalis, and can decompose on distillation.

Fats

They are solid oils. These include the triglycerides.

Volatile oils

They are aromatic and usually solids like camphor, thymol and menthol. 
Some are liquids like oil of eucalyptus, clove oil, cardamom oil, turpentine oil, sandalwood oil, balsam of tolu etc.

Waxes

 They are the esters of fatty acids with monohydric alcohol.

Saponins

They are “soap forming compound.  
They can cause haemolysis of RBC. 
They have photosensitization, hepatic toxicity, neoplastic and anti neoplastic properties. 
They are useful in vitiligo examples include senega. dioscorea, liquorice and quillaya.

Gums

They are transparent compounds form viscous solution with water. Examples include gum acacia and gum tragacanth.

Resins

They are sticky lipid soluble mixtures. 
They have antimicrobial and wound healing properties. 
Example includes podophyllum.

Gum resins

They are the combination of gums and resins. 
Examples include myrrh and asafetida

Oleoresins

They are the resins dissolved in volatile oils. 
Example includes copaiva.

Balsams

They are the resins in combination with benzoic acid with or without cinnamic acid. 
Examples include benzoin, peru and tolu.

Tannins

They can harden the mucous membrane by coagulation of proteins. They act as condensed astringents, and have anti diarrheal and anti hemorrhagic properties.

Neutral principles

They do not confer to any special group and include santonin and aloin.

Other bioactive compounds

Phytoestrogens

Phytoestrogens reduce hot flushes of menopause. 
It can reduce growth of ventral part of prostate.  
High oestrogenocity can cause infertility or can cause hypospadias during pregnancy.
The two main groups are isoflavones and lignans.

Isoflavoneshave both antioxidant and anti  hyper cholesterolemic properties 
Example include gentian. fenugreek, sebal serrulata and thuja.

Lignans present in the bran fraction of cereals. 
They present in podophyllum and sesame seeds. 
They can control hormone related cancers.



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