Alkaloids
((Compilation and arrangement of Engineer Javidi))
Description:
– Compounds of 1 to several nitrogen atoms that are connected to at least 2 carbon atoms in the ring ring system.
– They are widely distributed in plants.
– Vitamins and hormones are not alkaloids, but structurally, they are in the form of alkaloids in certain cases.
– Most alkaloids are derived from at least a number of amino acids (as their precursors) and a small number of isoprene units. Various combinations such as
aldehydes, hydroperoxides, organic nitrates and epoxies are converted), have been derived.
– The word alkaloid was coined by Meissner (a German chemist) and refers to all plant alkalis.
Abundance of alkaloids:
So far, more than 10,000 alkaloids have been identified in nature (more than 300 plant species) or in chemical experiments.
– It is found in 15 to 30 percent of plants, which shows this characteristic mostly in the families (Bagalai-Liliaceae-Alalgan-Palms and Anemones(.
– The most alkaloids in the world are caffeine and berberine.
– Most of the higher plants (plants: have seeds and a complete vascular system), have alkaloids.
Alkaloids are found in low plants (non-zoster: they reproduce by spores and do not have flowers or seeds like fungi) – microorganisms – insects and some mammalian organs.
– Dispersion of alkaloids:
Root-rhizome-leaf-peel-fruit-seed-juice
Examining the physical states of alkaloids:
-Generally white or colorless compounds with oxygenated crystalline salt
– They mostly have free oxygen and are in liquid form (nicotine-conine-spatine-lobulin(
– There are some alkaloids such as sanguinarine (red) and gelidonine (yellow(
– Most alkaloids, if they turn blue litmus red, means they are alkaline, except ephedrine and berberine, which are acidic.
Most alkaloids are insoluble in water, except ephedrine and colchicine, which are soluble in water.
Most alkaloids are soluble in chloroform-ether-alcohol.
Alkaloid salts are soluble in water and alcohol.
first group
Piperine and piperidine alkaloids:
Description:
– It has 6 nitrogen atoms in the (normal) ring. Of course, there is a benzene ring in the case of pyridine.
– The precursor of this alkaloid is ornithine and nicotinic acid.
Types of piperine and piperidine:
1).Coniine……………..:
– Toxic and volatile oily compound with short side aliphatic chain
– In hemlock (Conium maculatum from Chetrian family
2). Nicotine……………….
-Chemical formula (1-methyl2-3-pyridyl propylene), nicotine is a colorless oily alkaloid and soluble in water (alkaline state)
– It is the third most addictive substance in the world after heroin and cocaine
– Among the sources of nicotine, we can mention tobacco and other plants from the oleander family, including the Australian pittori.
Important nicotine alkaloids:
Nicotine-anabasein-neuronicotin
– The mechanism and effects of nicotine:
After consuming nicotine, it enters the brain from 7 seconds and after 15 to 30 seconds it involves the whole body. 80% is broken down in the liver – half life is 1 hour
– Involvement of central nerves
– Adrenaline stimulation and increase (heart rate, blood pressure, blood sugar, deep breathing, blood fat level, colon movements, lung and cough stimulation, and lung mixing) – increasing the adhesion of platelets – creating pleasant mental states, which after about 2 The clock turns into depression (causing a momentary release of dopamine in the brain) – Helping with early menopause – Stopping the mechanism of estrogen production in the brain of women (one cigarette is equivalent to one dose of nicotine) – (Nicotine addiction is stronger in women than in men) }-Increasing the risk of gallstones – Changes in the shape of sperm – Decrease in fertility and the speed and number of sperm – Destruction of eggs and…
Nicotine consumption from the perspective of traditional medicine:
increasing the production of bile and eventually burning and turning into soda…
Increased phlegm of burnt soda, causes: weight loss, loss of appetite, depression, susceptibility to various cancers and…
3). Trigonelline……………………
-Methylation product of nicotinic acid (vitamin B3)
Plants containing trigonelline: green coffee beans, fenugreek seeds, soybeans, alfalfa seeds, peas…
Properties: increasing insulin sensitivity (anti-diabetes) – anti-migraine – helping to treat cancer – reducing blood fat – anti-infection
4).Piperine…………………………………………..
Description:
With the chemical name of 1piperyl piperidine-piperine, it was first discovered in 1819 by a chemist named Hans Christian Oersted and named it piperina. Piperine consists of a piperidine nucleus attached to an aromatic moiety containing methylenedioxyphenyl. The piperidine ring system gives piperine the spicy taste of pepper, which, of course, has many medicinal effects.
–Properties:
Liver tonic-increasing the bioabsorption of medicinal and other food substances-high absorption in the small intestine and increasing the absorption of other substances and making the membrane of intestinal cells better permeable-modulating nerve receptors related to pain and depression-antioxidant and anti-inflammatory properties
Plants with piperine:
They are mostly found in the Piperaceae family.
Black pepper Piper nigrum, Ashwagandha Withania somnifera, cube pepper Piper cubeba, long pepper Piper longum and…
5).Arecoline…………………………
Description:
with the chemical name of arkaidine methyl ester
Plant sources: betel-pepper
Properties: In the food industry, by roasting betel nuts, brown areca powder is prepared, which is used as an extract of areca to repel tapeworms in cows, dogs, and horses. to empty the bowels of animals; and to treat intestinal colic in horses.
6).lobeline………………………………..
Description:
Lobeline alkaloid and its relatives lobelaline and lobelanidine are found in Lobelia plant or Indian tobacco (Lobelia inflate) in abundance.
Clinical properties: respiratory tract opener (anti-cough and asthma), improving immune health and helping to quit smoking (not addictive)
Anti-muscle spasm, reduces appetite by affecting the hormone ghrelin, anti-diabetic, antibacterial, heals insect bites, etc. (it is toxic in high doses and is only used clinically).
the second group)):Quinoline and Isoquinoline alkaloids:
Description:
– Bicyclic chemical structure of the combination of benzene and piperidine ring, which are similar to indole alkaloid in terms of chemical structure.
– Formed from the amino acids tryptophan and a monoterpene loganin (airoid(.
Quinine Alkaloid:………………………….
Description:
Anubinin and gammafergalin can be mentioned from quinine derivatives.
In the plants of the Ronasian family (Cenkonina bark) and the Sedabian family (Indian cedar), they have the most quinone.
Properties:
Food is highly toxic and can be consumed in canical form.
Local: spasmolytic-abortion-analgesic
Clinical (quinidine sulfate): abortion-cardiac arrhythmia-atrial fibrillation and…
Isoquinoline alkaloid:…………………………….
Description:
The result of condensation of one of the derivatives of phenylethylamine with derivatives of phenylacetaldehyde, which are derived from phenylalanine and tyrosine.
Plant sources:
They are mostly seen in the families of: Shagaigian-Zarshkian and Alalgan.
Among the most famous of these alkaloids:
Morphine-Tebaine-Toscapine and…
Clinical properties:
Spasmolytic – some of them are narcotic – antitussive – allelopathic compounds (antifungal, antibacterial and viral) – antioxidant – and…
Opium…………………………………………...
Description:
The sap of unripe fruits of the poppy plant is called.
The medicinal standard of opium is to have a minimum percentage of morphine of 10.
Opium alkaloids:………………………………
1).Morphine: 8-14 percent
sedative-narcotic-sedative-antipain-anti-cough-anti-spasm…
2). Noscapine: 4-8%
Anti cough
3).Codeine: 5.2-5.3 percent
Semi-narcotic-antitussive-reliever
4). Papaverine: 1-0.5%
Antitussive-spasmolytic
5).Tebain (paramorphine): 0.1-2%
Nausea-stimulant-convulsive
6). Berberine
Anti-inflammatory, anti-pyretic, anti-infective
7). Coptisin:
Anti bacterial
8). Canadian
Antibacterial-sedative
9). Cryptopin
Eliminate heart arrhythmia-reduce blood pressure
10).Isobolidine:
Help to release adrenaline-antibacterial
11).Staphylidine:
Lowering blood pressure-fever
12).Scorbodin
Sedative – binds to dopamine receptors
13).Isocorypalmin:
Decreased PLT
14).Levadonin:
Increased breathing
15).Magnofluorine:
Lowering blood pressure-anti-inflammatory
16).Immature:
Increasing respiratory movements (opposite to codeine) – analgesic
17).Protropin:
Lowering blood pressure and heart rate – anti-cardiac arrhythmia
18).Saguniarin:
Antitumoral-reducing tooth decay-antibacterial-increasing bowel movements.
Heroin alkaloid:
Chemical name: diacetylmorphine
– From synthetic derivatives of morphine
– Hallucinogenic – High narcotic – Decreases lung movements – Has hallucinogenic effects – Central nervous system stimulant
Harmful effects of morphine:
Addictive – reduction of eye pupil diameter – reduction of stomach acid – in higher doses: blockage of respiratory tract and death….
Ipcock……………………………..
The substance inside the rhizome of Cefalin plant (Ronasian family) has 3 important alkaloids:
– Alkaloid ometin: anti-chronic bonyitis
Alkaloidsphalin: strong nausea
Psychotrine alkaloid
Cledonine alkaloid……………………………..
Yellow alkaloid from Mamiran Kabir plant
Analgesic (less effective than morphine)-toxic
Berberine alkaloid.
in the roots of plants (barberry-Orkon grape-Indian barberry) and in the golden pig plant from the Hydrastis Canadensis family
Protoberberine subgroup – contains yellow crystalline salts
Properties:
Antibacterial and anti-fungal-opener of bile vessels-stimulatory effect-inhibitory effect on elastase enzyme (anti-inflammatory and tissue repair)-antitumoral.
Berberine + Sangonearin: Inhibitor of DNA synthesis of viruses
Berberine + sangonearin + palmatine: combination of allelopathy (allergic: toxic for viruses, bacteria, fungi, insects, parasites, etc.).
Disadvantages of barbarian:
Negative effect on the heart (decreasing heart rhythm)…
Boldine Alkaloid:
Chemical name: 1,10-dimethoxy-2,9-dihydroxyporphine
Derived from the leaves of the boldo plant and from the root of the Linderae Radix plant.
Properties: liver tonic-anti-dilation of liver vessels-antioxidant-cleansing bile-anti-gallstone-spasmolytic and…
Group of tropane alkaloids……………………………..
Description:
Complex molecules with pyrrolidine and piperidine ring structures derived from precursors of ornithine and phenylalanine (isoleucine and acetate) also play a role in tropane structures.
– Plants with tropane alkaloids are exclusively in the Solanaceae family.
– The important alkaloids of this group are hyoscyamine-hyosine-scopolamine-atropine (it is the racemic form of hyosine and is found very rarely in nature).
Hyoscyamine alkaloid:
Property: anti-cholinergic, anti-muscarinic
Increasing the heart rate – reducing the pain of smooth muscles (stomach and uterus) – reducing sweating – dilating the pupils of the eyes – reducing the secretion of the stomach – and…
Alkaloid hyoscyamine + alkaloid atropine: anti-diarrhoeal-anti-tremor in parking lot
Alkaloid scopolamine:
useful in motion disorders and…
Atropine alkaloid: muscle relaxant, antispasmodic, anti-alzheimer and…
Clinical drugs such as atropine (neostigmine-physostigmine-rivastigmine): anti-Alzlimer-muscle paralysis and…
Complications of tropane alkaloids (especially Solanacea A: Bazalbanj, Shabizak, Datura, etc.):
Pupil dilation-Visual disorders-Dry skin-Illusions-Excessive sweating-Dry mouth mucosa-Decreased level of consciousness-For children and those who have a low resistance level, it is fatal in high doses…
Quinolizidine alkaloid group (lupine)
Description:
This alkaloid was discovered for the first time in the Lupine plant species from the Papilionaceae family, and the name of the alkaloid comes from the name of the plant species.
Chemical structure: bicyclic carbon with a common nitrogen atom
Important group alkaloids:
Aspartine alkaloid:
In the large mammary plant and the peacock flower
Properties: Exotoxin, heart stimulant, diuretic and…
Alkaloid cytisine:
It is available in the plant species of lupins.
Mirin Alkaloid:
in the Qaraqat plant (Khalengian family is available)
In some countries, they make a type of cigarette that is very dangerous.
group of pyrrolizidine alkaloids………………….
Description:
Chemical structure: a 5-membered bicyclic ring with a common nitrogen atom between them is the precursor of pyrrolizidine alkaloid, ornithine.
In this example, alkaloids are generally water-soluble nitrogen oxides.
The family of plants with pyrrolizidine alkaloid:
Family (Borage-Astracea-Papilliona C.A(
Properties: In high doses, liver poisoning is fatal.
Indole alkaloids group:
Description:
A large alkaloid group with a pyrrole ring fused to benzene
– The amino acid tryptophan is seen in the biosynthesis of certain indoles.
– In the main subgroups of indole in Paryosha plants and Raulphia plants (Apocynaceae), other secondary compounds called monoterpene iroid lignans are also found.
– In indole alkaloids, there is a complex polycyclic system.
– There is this alkaloid in the family of plants (mousetails-runasian-pitchakians-mushrooms (large psilocybin mushroom))
– They can be seen in plants (Madagascar sedum-Rawlfia-Alstonia-Zaravandhandi).
Properties: Sedative-reduces blood pressure-fever-stimulates the uterus-effect on heart rate.
Types of indole alkaloids:
Reserpine-resinamine-dispyridine-ajmaline-alstonin-alstonidine.
Periwinkle plant species (Madagascar)………………….
Description:
More than 100 alkaloids have been discovered in this plant species.
Alkaloids: vinbalastine and vincirizine, which are anti-neoplastic and are used in children’s chemotherapy (leukemia) and Hodgkin’s (lymphatic gland cancer)
Provencals are alkaloids (vinsamine-majodine-majordine). which are mostly astringent and anti-bleeding.
Note:
Not all types of paryosha have neoplastic properties.
Alkaloid group of Ergot
Description:
-Ergot (cereal rust): mushroom (long-spiny-brown and purple outer layer) from Claviceps purpurea family – has a sclerotium 1-5 cm long and 2-5 mm wide – ergot means rotten tooth (in Latin) It lives on cereal grains, especially rye.
It has 20 indole alkaloids.
Ergot poisoning
Oral blisters-diarrhea and vomiting-heartache-in some people constipation-increased salivation-miscarriage
Ergot alkaloids:
Ergotamine alkaloid: clinical properties: anti-migraine
Ergonavine alkaloid: clinical properties: oxytocin and vasoconstrictor, and is used in the treatment of postpartum hemorrhage.
Lysergic acid alkaloid
Alkaloid stregnine: extremely lethal, in a dose of 60-90 mg, it causes blockage of blood vessels and death.
It is found in ergot and horsetail plant (mouse tail family(.
Brucine alkaloid: like stregnine with a milder effect.
Yohimbine alkaloid: Blanco skin (Khorzareyan family): sexual tonic.
Alkaloid Yohime: It is found in the Rhonasian family and is a sexual tonic.
Steroidal alkaloid group:
Description:
– derived from terpenoids – found in plants of the family (Liliaceae and Solanaceae).
– In Solanaceae, they are in glycosidic form
Solasodine alkaloid: It is extracted from the fruit of Tajrizi and a species of Avicular Estravia.
Alkaloid solanine and alkaloid beta chaconine: (glycoalkaloid) and containing solanidine aglycone – found in potato sprouts and unripe potatoes
Property: extremely toxic and lethal (high doses) – causes abortion – reduces growth and…
– The green and white gorse plant (Liliaceae family) contains ester alkaloids, some of which are oxidized, called alkaloid watrin, which affects the Na-k ATPax enzyme and causes a decrease in cardiac activity and blood pressure. They are highly toxic.
The group of alkaloid amines (false alkaloids)……..
Description:
– Simple compounds derived from ammonium.
– Contains precursors of aromatic amino acids.
Ephedrine and pseudoephedrine alkaloids:
Description:
It has a simple aromatic skeleton structure derived from phenylalanine (an additional group is derived from methionine). The isomeric structure of ephedrine is pseudoephedrine.
Property:
Nervous system stimulant – narrowing and blocking of blood vessels – increasing blood pressure and heart pulses – diuretic – opening respiratory passages – used in the treatment of anaphylaxis shock – in high doses, it causes drowsiness, hallucinations, and decreases heart rate.
Good luck – Engineer Javidi
