Aporphine alkaloids

All the aporphine alkaloids are based on the 4H dibenzo quinoline structure or its 3-methyl derivative commonly known as the aporphine nucleus.

Index" The numbering system is as indicated, so as to conform with the "Ring

Glaucine

This widely occurring alkaloid has now been reported in Glaucium flavum (yellow horned poppy), and other plants. In mammals, glaucine produces slight narcosis ( لوهذ ) followed by convulsions, and is depressant to the heart and striated muscles .

Glaucium flavum (yellow horned poppy) Glaucium flavum (yellow horned poppy) is a summer flowering plant in the Papaveraceae family, which is native to Northern Africa, Micronesia, temperate zones in Western Asia and the Caucasus, as well as Europe. Habitat: the plant grows on the seashore and is never found inland. All parts of the plant, including the seeds, are toxic and can produce a range of symptoms up to and including respiratory failure resulting in death FDA poisonous plants database. It is a noxious weed( ةراض باشعأ ) in some areas of North America.

Laurolitsine

)

Norboldine

( Laurolitsine has been isolated from the leaves of

Neolitsea sericea and the root, bark, and wood of

Litsea japonica . It is an amorphous powder which can be characterized as the picrolonate, m.p. 239' dec., or the picrate salt, m.p. 212' dec. The alkaloid has two methoxyl and two hydroxyl groups, and in addition possesses a secondary aliphatic amine function as indicated by a positive Feigl test.

Laurolitsine

exhibited potent cytotoxicity towards pancreatic cancer cell line

Laurolitsine

Litsea japonica

Litsea is a genus trees or shrubs belonging to the Laurel family, Lauraceae. The genus includes 200 to 400 species in tropical and subtropical areas of both hemispheres. Trees or shrubs, dioecious.

The leaves can be either deciduous or evergreen depending on species, and aromatic. The flowers are from greenish to white, greenish-yellow, yellowish

Bulbocapnine • • Bulbocapnine is an alkaloid found in Corydalis cava (Papaveraceae) and Dicentra, plants in the family Fumariaceae that can cause fatal poisoning in sheep and cattle. It has been shown to act as an acetylcholinesterase inhibitor, and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase.

It "inhibits the reflex and motor activities of striated muscle. It has been used in the treatment of muscular tremors and vestibular nystagmus". The psychiatrist Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor.

Bulbocapnine

Corydalis cava (Papaveraceae)

Nor-lupinane ( Quinolizidine ) Alkaloids • • • • •

Quinolizidine alkaloids are a widely distributed, heterogeneous group of alkaloids having known toxicity to humans and domestic animals. Plants containing quinolizidine alkaloids with known toxicity include the following: Baptisia species (false indigo) Cytisus species (scotch broom) Laburnum species (goldenchain, laburnum) Lupinus species (lupine, bluebonnet) Sophora species (mescal bean, frijolito)

Quinolizidine

Cytisine Cytisine, also known as baptitoxine and sophorine, is a toxic alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. Despite its toxicity (LD 50 i.v., in mice ~2 mg/kg), it has been used medically to help with smoking cessation: recent clinical trials have shown cytisine to be more effective than conventional smoking cessation aids and it is much cheaper than similar products. Its molecular structure has some similarity to that of nicotine and it has similar pharmacological effects. Excessive doses can interfere with breathing and cause death. their stimulant effects and mild hallucinogenic properties.

Mescal bean may have been used by Native American peoples for ceremonial and medicinal purposes. Sophora root is used in traditional Chinese medicine where it is known as "Ku Shen" and is used to treat dysentery, scabies, itchy rashes such as with eczema, skin lesions, jaundice, edema, urinary dysfunction, and vaginal discharge

Cytisine

Mescal bean

Sparteine Sparteine is a lupin alkaloid containing a tetracyclic bis-quinolizidine ring system derived from three C 5 human use as an antiarrhythmic agent.

chains of L-lysine. It is a antiarrhythmic agent; a sodium channel blocker. It is an alkaloid and can be extracted from scotch broom. It is the predominant alkaloid in Lupinus mutabilis, and is thought to chelate the bivalents calcium and magnesium. It is not FDA approved for It is also used as a chiral base in organic chemistry, and as a ligand in an inorganic chemical synthesis.

Scotch Broom

Indolizidine Alkaloids

The indolizidine alkaloids can be divided into two major groups, the phenanthroindolizidines from the Asclepiadaceae and Moraceae families and the simpler indolizidines from all other sources.

Indolizidine Nucleous

PHENANTHROINDOLIZIDINE ALKALOIDS

Phenanthroindolizidines are a series of plant-derived natural alkaloids primarily found in the Asclepiadaceae and Moracea plant family.

R-tylophorine, R-antofine, and R-cryptopleurine are well known representatives in the family having been reported to have potent antitumor activity. Phenanthroindolizidine alkaloids have been isolated from only two plant families.

Their presence has been established in several species of five genera,

Tylophora, Cyanchum, Vincetoxzcum, Pergularza and Antitoxzcum among the more than 300

genera of the Asclepiadaceae family and in one species of the genus Ficus of the Moraceae family. A major side effect

of these natural alkaloids impacting their use as therapeutic agents is their severe CNS toxicity.

Tylophorine

Tylophorine, a phenanthraindolizidine alkaloid isolated from Tylophora indica exerts antiangiogenic and antitumor activity by targeting vascular endothelial growth factor receptor 2-mediated angiogenesis, thus may be a viable drug candidate in anti-angiogenesis and cancer therapy

Tylophorine

(R)-antofine

R-cryptopleurine

Imidazole Alkaloids

• •

alkaloids containing the imidazole nucleus.

the smallest group in terms of structure numbers, which are formed by precursors derived directly from the amino acid L-histidine

.

imidazole nucleus

L-histidine.

Pilocarpus alkaloids

Chemically, the majority of Pilocarpus alkaloids hold

simultaneously an imidazole and a γ-lactone ring.

Pilocarpine was first isolated, in 1875, by Hardy and by Gerrard, in distinct works, as colourless crystalline salts from P. jaborandi Holmes leaves . This alkaloids

is also found in several other species such as P. microphyllus Stapf.,where total pilocarpine content range from ca. 3.0 to 70% of total alkaloids. Isopilocarpine is the epimerization product of pilocarpine produced by enolization pathway.

Pilocarpine

Pilocarpine is a drug used to treat dry mouth (xerostomia) and glaucoma. It is a parasympathomimetic alkaloid obtained from the leaves of tropical American shrubs from the genus Pilocarpus. It is a non-selective muscarinic receptor agonist in the parasympathetic nervous system, which acts therapeutically at the muscarinic acetylcholine receptor M3 due to its topical application, e.g., in glaucoma and xerostomia.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Pilocarpine stimulates the secretion of large amounts of saliva and sweat.

P ilocarpine

Histamine

• Histamine is a biogenic amine formed by L histidine decarboxylation mediated by HDC (histidine decarboxylase) and naturally occurs in some fungi, marine and plant species. It was isolated from aerial parts of Capsella bursa-

pastoris L. (Brassicaceae), Lolium perenne L.

(Poaceae) and Spinacea biosynthesis such as amides.

oleracea L.

(Chenopodiaceae). This amine may act as an intermediate in many imidazole derivatives

Histamine involved in local immune responses as well as regulating physiological function in the gut and acting as a neurotransmitter.

Histamine is involved in the inflammatory response. As part of an immune response to foreign pathogens, histamine is produced by basophils and by mast cells found in nearby connective tissues.

Histamine increases the permeability of the capillaries to white blood cells and some proteins, to allow them to engage pathogens in the infected tissues Histamine

Purine (Xanthine) Alkaloids

The purines are consisting of a six-membered pyrimidine ring fused to a five-membered imidazole ring. The pharmaceutically important bases of this group are all methylated derivatives of 2,6 dioxy-purine (Xanthine). This group includes mainly Caffeine, theobromine and theophylline alkaloids. These alkaloids are weak bases, they give no precipitate with Mayer's reagent.

Purine Xanthine

Caffeine

Caffeine is a bitter, white crystalline xanthine alkaloid and a stimulant drug. Caffeine is found in varying quantities in the seeds, leaves, and fruit of some plants, where it acts as a natural pesticide that paralyzes and kills certain insects feeding on the plants, as well as enhancing the reward memory of pollinators. It is most commonly consumed by humans in infusions extracted from the seed of the coffee plant and the leaves of the tea bush, as well as from various foods and drinks containing products derived from the kola nut.

Other sources include yerba mate, guarana berries, guayusa, and the yaupon holly.

In humans, caffeine acts as a central nervous system stimulant, temporarily warding off drowsiness and restoring alertness. It is the world's most widely consumed psychoactive drug, but unlike many other psychoactive substances, it is legal and unregulated in nearly all parts of the world. Beverages containing caffeine, such as coffee, tea, soft drinks, and energy drinks, enjoy great popularity.

Caffeine

Theobromine

Theobromine, is a bitter alkaloid of the cacao plant, with the chemical formula. It is found in, chocolate as well as in a number of other foods, including the leaves of the tea plant, and the kola (or cola) nut. It is classified as a xanthine alkaloid. Despite its name, the compound contains no bromine—theobromine is derived from Theobroma, the name of the genus of the cacao tree, (which itself is made up of the Greek roots theo ("God") and broma ("food"), meaning "food of the gods") with the suffix -ine given to alkaloids and other basic nitrogen-containing compounds. Theobromine is a slightly water-soluble (330 mg/L), crystalline, bitter powder. Theobromine is white or colourless, but commercial samples can be yellowish. It has a similar, but lesser, effect to caffeine in the human nervous system, making it a lesser homologue.

Theobromine is an isomer of theophylline, as well as paraxanthine.

Theobromine is categorized as a dimethyl xanthine. In modern medicine, theobromine is used as a vasodilator (a blood vessel widener), a diuretic (urination aid), and heart stimulant.

Theobromine

Theophylline

• • • • • • • Theophylline, also known as 1,3-dimethylxanthine, is a methylxanthine drug used in therapy for respiratory diseases such as COPD(Chronic obstructive pulmonary disease) and asthma under a variety of brand names. As a member of the xanthine family, it bears structural and pharmacological similarity to caffeine. The main actions of theophylline involve: relaxing bronchial smooth muscle increasing heart muscle contractility and efficiency increasing heart rate increasing blood pressure increasing renal blood flow anti-inflammatory effects central nervous system stimulatory effect mainly on the medullary respiratory center

Theophylline

Coffee Tree

Cacao Tree

STEROIDAL ALKALOIDS

steroid nucleus

Classification Steroidal alkaloids may be divided into three groups on the basis of botanical source:

(a)solanum alkaloids, obtained from S. tuberosum (potato), S.

lycopersicum (tomato), and other species ;

(b) veratrum alkaloids usually from V. album and V. viride (European and American “ hellebore ”) or from sabadilla (V. sabadilla) seeds ;

(c) kurchi or holarrhena

alkaloids from ‘‘ kurchi ” (H. antidysenterica), a small Indian shrub, and from other Indian and African species of Holarrhena. All the kurchi alkaloids of well-authenticated structure contain a carbon framework of twenty-one atoms similar to that of the steroid hydrocarbon pregnane ; owing however to the presence of N-methyl groups the number of carbon atoms in the molecules of these alkaloids may rise to twenty-four (the alkaloid conkurchinine may contain twenty-five carbon atoms in the molecule.

a)solanum alkaloids

α-chaconine and α-solanine, derived from the aglycone solanidine

,

solanidine The sugar portion of these glycoalkaloids hydrolyses in the body, leaving the solanidine portion

Solanine

Solanine is a glycoalkaloid poison found in species of the nightshade family (Solanaceae), such as the potato (Solanum tuberosum) and the tomato (Solanum lycopersicum). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has fungicidal and pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade (Solanum nigrum), after which it was named.

Solanine

Solanine poisoning

Solanine poisoning is primarily displayed by gastrointestinal and neurological disorders. Symptoms include nausea, diarrhea, vomiting, stomach cramps, burning of the throat, cardiac dysrhythmia, nightmare, headache and dizziness. In more severe cases, hallucinations, loss of sensation, paralysis, fever, jaundice, dilated pupils, hypothermia and death have been reported.

Ingestion of solanine in moderate amounts can cause death. One study suggests that doses of 2 to 5 mg per kilogram of body weight can cause toxic symptoms, and doses of 3 to 6 mg per kilogram of body weight can be fatal. Symptoms usually occur 8 to 12 hours after ingestion, but may occur as rapidly as 30 minutes after eating high-

solanine foods. Solanum glycoalkaloids can inhibit cholinesterase, disrupt cell membranes, and be teratogenic (cause birth defects).

Chaconine

α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the Solanaceae family. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste. Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties

Tomatidine

It is obtained from the roots of Rutgers tomato plant [Lycopersicon esculentum Mill., cultivar.

“Rutgers”] (Solanaceae).

Identification Test Its hydrochloride derivative (C 27 H 45 NO 2 .HCl) is obtained as crystals from absolute ethanol having mp 265-270°C and [α ] D 25 -5 o (methanol).

b)Veratrum Alkaloids

Veratridine

Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by abolishing inactivation of sodium ion channels. It is primarily obtained from the herb Veratrum and sabadilla seeds It is used in ointments for the treatment of neuralgia and rheumatoid pain

Veratridine

Jervine

it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.

c) Alkaloids from ‘‘ kurchi

The plant Holarrhena antidysenterica Linn. is

commonly known in India as , Kurchi.

Kurchi

Conessine

Conessine is a steroid alkaloid found in a number of plant species from the Apocynaceae family, including Holarrhena antidysenterica. several of which are used in traditional herbal medicine as a treatment for amoebic dysentery. It acts as a histamine antagonist.

The following two alkaloids in high dilutions, kill Paramecia, Colpidia and Daphnia conkurchine holarrhenine