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alcaloizi

alcaloizi

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Published by Isav
A short description of alkaloids
A short description of alkaloids

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Published by: Isav on Jan 26, 2009
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09/29/2012

 
1
ALKALOIDS.
ELZBIETA & HANS BRAND ELZBIETA COSMETICS BV, THE NETHERLANDS 
Alack, alack, is it not like that I,So early waking, what with loathsome smells,And shrieks like mandrakes' torn out of the earthThat living mortals, hearing them, run mad.
Romeo and Juliet 
; Act IV, Scene 3The forked root of mandrake was thought to be in the power of dark earth spirits.Mandrake would only be growing after a man was hung on the gallows, being fed by theurine and semen of the dead man. It was believed that it could be uprooted safely only inthe moonlight, after appropriate prayer and ritual. With the tip of a willow wand three cir-cles were drawn around the plant, and then a black, hungry dog was attached to theplant by a cord. The dog was put a juicy sausage in front of his nose, and his hungermade him pull the mandrake root out of the ground. It was thought that as the mandrakeroot was pulled from the ground, it uttered a shriek that killed or made mad those whodid not block their ears against it. The dog would die anyway, because of either starva-tion or instant overfeeding.Mandrake, also named Mandragora (Mandragora officinarum), is probably themost famous magic plant known. Already used in Egypt 3500 years ago, it was in theGrecian times considered as an extremely powerful aphrodisiac and fertility enhancer.Mentioned in the Koran, and strictly forbidden. The sponge that was given to Jesus onthe cross is said to contain mandragora juice.
 
2
In the dark ages mandragora was loaded with dozens of myths, and it played amajor role in witchcraft. Witches prepared mixtures of extracts of henbane (Hyoscyamusniger), deadly nightshade (Atropa belladonna) and mandrake root, to be applied on theskin or on the genitals. These plants belong to the family of Solanaceae, the nightshadefamily. The mixture is extremely rich in tropane alkaloids, such as hyoscyamine, sco-polamine, atropine, hyoscine, cuscohygrine and mandragorine. Biosynthesis of tropanealkaloids start with ornithine (a dibasic amino acid) or arginine an amino acid with aguanidium group attached to it); the biosynthetic pathway has been completely eluci-dated. Other alkaloids use lysine, phenylalanine, tyrosine, methionine or tryptophan asthe starting amino acid, eventually as their amino aldehydes or amines derived fromthem.All of these are characterised as alkaloids, in today’s nomenclature identified asorganic nitrogen bases from botanical origin (although that is strictly not true as also inthe Animal Kingdom alkaloids occur). The name “alkaloid” comes from the Arabic wordfor ash “
al-qali 
”. Al-qali was obtained by roasting (European) saltwort (Salsola kali), theashes being rich in sodium and potassium carbonate. In the Golden Century of Damas-cus craftsman were able to purify the ashes to obtain white crystals composed of a mix-ture of Na
2
CO
3
and K
2
CO
3
, and this enabled them to make transparent glass.On average alkaloids are poisonous to extremely poisonous, but frequently theyare extremely useful applied in pharmacy, usually without a synthetic countertype. Virtu-ally all plants contain alkaloids. Alkaloids are quite frequently responsible for the cos-metic benefits obtained from botanical extracts. Often condemned, frequently glorified.Like the girls on the catwalk who like to apply the juice of a deadly nightshade berry tothe eyelids to get nice, large pupils. The name “atropine” comes from Atropos, the Fatewho severs the thread of life; you will remember how Atropos works if you have readStephen King’s book “Insomnia”. Belladonna is also named Devil’s Cherries because ofthe excellent taste of the glossy, black berries, but eating a few will surely result in a hor-rible death.
ββ
-PHENETYLAMINES
β
-Phenetylamine (a colourless liquid with a boiling point of 197
°
C) is the parentsubstance of a group of alkaloids.
β
-Phenetylamine itself occurs in putrid meat; it isformed by decarboxylation of phenylalanine. It occurs in mistletoe (Viscum Album), andin Brassica species (cabbage, kale, cauliflower). d-(-)-Ephedrine is an important de-rivative which occurs in the genus Ephedra. It is one of the most important drugs in MaHuang (Ephedra Sinensis), a Chinese drug, containing ~2-2,5% ephedrine. Ma Huang,also known as ephedra, is used for weight management and appetite suppression,but is restricted in most countries. Pakistani ephedra contains much smaller amountsof ephedrine (~0,7%).
HHOORRDDEENNIINNEE 
ββββ
--PPHHEENNEETTYYLLAAMMIINNEE CH
2
 
( )NH
22
HO CH
2
( )NMe
22
 
3
Ephedra-containing supplements produce a state of wakefulness and alertness,a decreased sense of fatigue, and a mood elevation with increased self-confidenceand initiative. Unfortunately, the beneficial effects in weight management and mood al-teration come at a price: high doses of ephedrine result in depletion of epinephrine(adrenaline) and norepinephrine (noradrenaline), leading to the opposite effects: de-pression, a sense of loneliness and suspiciousness. Also, ephedrine may elevateblood pressure, increases heart rate and comes with severe palpitations. In very seri-ous cases this can cause ventricular fibrillation and death. The use of Ma Huang, par-ticularly in conjunction with caffeine, should be discouraged because of the side ef-fects.The physiological activity of ephedrine compares to benzedrine (amphetamine)and tyramine. Benzedrine is not found in nature, but tyramine occurs in germinating bar-ley (Hordeum vulgare), and is produced by putrefaction of proteins (decarboxylation oftyrosine). It is also found in tangerine (Citrus reticulata) and orange (Citrus Sinensis),although the amounts are insignificant. Mescaline (3,4,5-trimethoxy-
β
-phenetylamine isfound exclusively in Mexican peyote (Lophophora Williamsii), next to related alkaloidssuch as hordenine. Hordenine (4-hydroxy-N,N-dimethyl-
β
-phenetylamine) is more wide-spread in plants. It is found in e.g. Selenicereus grandiflorus (Queen-of-the-Night) andTamarindus indica (tamarind).Adrenaline is a non-steroid hormone belonging to the
β
-phenetylamine group; itwas the first hormone be to isolated in a crystalline form (Takamine; 1901). It raisesblood pressure and is used locally to stop haemorrhage. Adrenaline is responsible forthe storage and mobilisation of glycogen and fatty acids and tunes the correspondingmetabolic pathways. Adrenaline is also a neurotransmitter of the adrenergic nervoussystem.
PYRROLIDINE ALKALOIDS.
About 80 pyrrolidine alkaloids are known, hygrine being the simplest representa-tive. It is one of the coca alkaloids (Erythroxylum coca), chemically identified as N-
EEPPHHEEDDRRIINNEE CH NH(Me)CHOH CH
3
AAMMPPHHEETTAAMMIINNEE CH NH
2
CHCH
3
AADDRREENNAALLIINNEE CH NH(Me)CHOH CH
3
HOHONNOORRAADDRREENNAALLIINNEE CH NH
2
CHOH CH
3
HOHO
2
H
3
COH
3
COH
3
COCH
2
( )NH
22
MMEESSCCAALLIINNEE MESCAL

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