Pharmacognosy with the Basics of Plant Biochemistry - Kovalyov, V. M. 2004

Special Part
Alkaloids
Medicinal Plants and Raw Materials Containing Isoquinoline Alkaloids

POPPY CAPSULES, OPIUM — PAPAVERIS CAPITATA, OPIUM

Opium poppy — Papaver somniferum L., fam. Papaveraceae

Opium poppy; papaver is the latinized name of the poppy, derived from papa (children's porridge); Lat. somniferum from somnus (Sleep) and ferre (to bear).

An annual herbaceous plant, glabrous or sparsely setose.

Stem erect, simple or branched above, 50-120 cm high. Leaves, except the lowest ones, stem-clasping, entire, coarsely dentate or incised-lobed, glaucous.

Flowers large, bisexual, four-petaled, solitary, on long terminal pedicels; petals white, violet, or purple, with a white, violet, or yellowish spot at the base. Fruit — a globose or barrel-shaped capsule.

The cultivation of the opium poppy and The production of opium are controlled by the UN International Narcotics Control Board. Cultivating poppies in Ukraine is prohibited.

Distribution. Poppies are cultivated in Turkey, Kazakhstan, Uzbekistan, Romania, Australia, France, and Spain. Processing plants receive raw opium or oilseed poppy waste in the form of poppy straw.

Chemical composition of opium. About 30 Alkaloids of various isoquinoline subgroups have been identified: 1) morphine subgroup — morphine, codeine, thebaine; 2) benzylisoquinoline and benzyltetrahydroisoquinoline subgroup — papaverine, narcotine, narceine. Ballast substances account for 80% of the mass of opium. Opium processed for medical purposes must contain at least 10% morphine.

Opium contains 3-5% meconic acid, which exists both in a free state and as salts (meconates) with morphine, codeine, and other alkaloids. Meconic acid is easily identified in both free and bound states by its purple (red) coloration with iron(III) chloride. The presence of this acid confirms the presence of opium alkaloids.

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Meconic acid

Biological activity and application. Omnopon (a mixture of opium hydrochlorides) and morphine are prescribed as analgesics for injuries, prolonged pain, etc.

To reduce the narcotic effects of morphine, morphilong was developed, which is a 0.5% solution of morphine hydrochloride in a 30% aqueous solution of polyvinylpyrrolidone. This drug is used as a non-addictive analgesic.

Codeine (codeine phosphate and codeine base), codterpin, and cough tablets are prescribed to suppress coughs.

Papaverine is an antispasmodic agent used for spasms of Blood Vessels (Hypertension, angina pectoris, migraine), spasms of the smooth Muscles of the Abdominal cavity, and Bronchial Asthma.

Papaverine is a component of combined drugs: paphylin (papaverine + platyphylline), papazol (papaverine + dibazole), cheliverine (papaverine + khellin), chelatrine (papaverine + khellin + atropine), bepaeal, nicoverine, paluphin, theoverine, tepaphilin, etc.

In homeopathy, opium is used as a respiratory stimulant that restores Blood Circulation; for delirium tremens, constipation, spasm of the Urinary Bladder sphincter, stuttering, Epilepsy, insomnia, and nervous excitation.

YELLOW HORNED POPPY HERB — HERBA GLAUCII FLAVI

Yellow horned poppy — Glaucium flavum Crantz, fam. Papaveraceae

Yellow horned poppy, yellow glaucium; the name comes from Lat. glaucus — glaucous; flavus, -um — yellow.

A herbaceous plant, 30-50 cm high. ROOT vertical, containing milky juice. Above-ground parts usually devoid of milky juice. Stems glabrous, branched. Leaves thickish, glaucous, basal ones densely pubescent, large (15-35 cm long), lyrate-pinnatifid, middle stem leaves sessile, more deeply lobed, upper ones stem-clasping at the base, glabrous. Flowers large, up to 5 cm in diameter. Calyx of two sepals that fall off when the flower opens. Petals four, yellow, sometimes orange. Fruit — a pod-like capsule up to 15 cm long. Blooms in May-June; the flowering period is very protracted, so buds, flowers, and ripe fruits can be found simultaneously.

Distribution. In the wild, the yellow horned poppy is found along the Black Sea coast on sands, sometimes among weeds along the banks of rivers flowing into the sea, less often on stony slopes. The reserves of the horned poppy in the Crimea and the Caucasus are insignificant, which is why it has been introduced into cultivation in the Crimea and Krasnodar Krai.

Harvesting. Subject to proper agricultural practices, two harvests of the herb can be carried out during flowering in the First and Second years of cultivation. The herb is dried in dryers at a Temperature of 50-60 °C or in the open air.

Chemical COMPOSITION OF THE raw material. The total alkaloid content in the phase of mass flowering reaches 4 %. The most valuable component is glaucine, an alkaloid of the aporphine group. The content of glaucine constitutes nearly 50% of the total alkaloids and sometimes reaches 2% of the dry weight of the aerial parts. In addition, other aporphine-type alkaloids have been isolated from the yellow horned poppy, including corydine, isocorydine, the protopine-group alkaloid isoboldine, protopine and allocryptopine of the protopine group, as well as benzophenanthridine-group alkaloids such as sanguinarine, chelerythrine, chelerubine, norchelidonine, chelidonine, magnoflorine, etc. Other identified compounds include fumaric (glaucinic) and dioxymaleic acids, mucus, and Flavonoids (rutin).

Biological activity and application. Glaucine exhibits an antitussive effect that exceeds codeine in potency and duration without producing narcotic side effects. Glaucine preparations, such as glaucine hydrochloride, glauvent, and broncholitin, are used as antitussive agents for Diseases of the Lungs and Upper Respiratory Tract, Bronchitis, and Pneumonia.

Glaucine lowers blood pressure, exerts a sedative effect, and relaxes smooth muscles. The Use of glaucine preparations is particularly advisable in cases where respiratory disorders are combined with hypertension.

MACLEAYA HERB — HERBA MACLEAYAE

Plume poppy — Macleaya cordata (Willd.) R. Br., microcarpus plume poppy — Macleaya microcarpo (Maxim.) Fedde, fam. Papaveraceae. Named in honor of the Scottish entomologist A. Macleay; microcarpus, -a — small-fruited; cordatus, -a — cordate.

A perennial herbaceous plant with an orange milky sap and an unpleasant odor. Stems are erect, up to 2.5 m in height. Leaves are long-petiolate, alternate, palmately lobed, 5-7-parted, large (20-30 cm long), bluish-green above, nearly white underneath, with prominent Veins. Flowers are pink, pleasantly scented, gathered in long (30-40 cm) terminal racemes. The fruit is a capsule.

The species differ in flower and fruit Structure. Macleaya cordata has 25-30 stigmas per flower and a lanceolate capsule containing 2-6 seeds, whereas Macleaya microcarpa has 8-12 stigmas and a rounded capsule with a single seed.

Distribution. Native to Japan and China. Cultivated in Ukraine and the Krasnodar Krai.

Harvesting. Alkaloid accumulation reaches its maximum during the third year of plant growth. The herb is harvested mechanically in the budding to early flowering stages and dried immediately at 40-50 °С. Safety precautions must be observed when handling Macleaya, as the plant is poisonous.

Chemical composition of minder raw material. Macleaya herb contains isoquinoline alkaloids (0.7-1.5 %), including allocryptopine, sanguinarine, chelerythrine, protopine, and berberine.

Sanguinarine

Chelerythrine

Biological activity and application. The sum of sanguinarine and chelerythrine alkaloid bisulfates forms the drug sanguirythrine, which exhibits antimicrobial activity against Gram-positive Bacteria and antiprotozoal (anti-trichomonal) activity. As an anticholinesterase agent, it is prescribed for cerebral palsy, myopathies, spastic Facial Nerve paresis, and progressive muscular dystrophy.

GREATER CELANDINE HERB — HERBA CHELIDONII

Greater celandine — Chelidónium majus L., fam. Papaveraceae

The name originates from the latinized Greek name of the plant, chelidonion, derived from chelidon — swallow; Lat. major, majus — greater.

A perennial herbaceous plant with a multi-headed, branched root that is reddish-brown on the outside and brown on the inside.

The stem is branched. Basal and lower stem leaves are petiolate, while the upper ones are sessile and alternate. All leaves are deeply pinnatifid, with 3-5 pairs of lobes; the lobes are rounded and irregularly crenate, with the terminal lobe being more rounded, typically trilobed. The leaves are green above and have a characteristic bluish-green color underneath. Flowers are tetramerous, yellow, grouped in simple umbels of 3-8. The Ovary is superior, elongated, with a sessile bilobed stigma. The fruit is a multi-seeded elongated capsule. Seeds are black, glossy, with a white crest-like appendage. The entire plant contains a yellow milky sap.

Distribution. Grows throughout Ukraine in shady places among bushes and in forests; does not form large thickets.

Harvesting. During the flowering phase, the herb is cut using knives or sickles; in dense stands, the upper parts are mown without the coarse stem bases. Drying is carried out in attics or dryers at 50-60 °С. Dust irritates mucous membranes, therefore respirators should be worn when working with the dried raw material.

Chemical composition of the raw material. All PARTS OF THE plant contain alkaloids (1.8–3%): chelidonine, homo-, oxy-, methoxychelidonine, chelerythrine, sanguinarine, protopine, a- and ß-allocryptopine, sparteine, berberine, etc. The alkaloids are present in pure form or bound to chelidonic acid.

Chelidonine

Chelidonic acid

The herb contains saponins, flavonoids, ascorbic acid, carotene, and organic acids.

Biological activity and application. An infusion of celandine herb and the juice of the fresh herb and roots are used to treat condylomas and pharyngeal papillomatosis.

In small doses, celandine preparations are taken orally for Liver and Gallbladder disorders. Experiments show they inhibit the growth of malignant tumors and exhibit fungistatic and bacteriostatic effects against tuberculosis pathogens.

In homeopathy, the fresh flowering herb with roots is used for pain beneath the shoulder blade, a bitter taste in the Mouth, severe nausea, and topically for warts and polyps.

BARBERRY LEAVES — FOLIA BERBERIDIS

BARBERRY ROOTS — RADICES BERBERIDIS

Common barberry — Berberis vulgaris L., fam. barberry — Berberidaceae

Common barberry; the name comes from berberis, idis, the Latinized plant name; Lat. vulgaris means common.

Plant description. A branched, deciduous, spiny shrub up to 2.5 m in height. The roots are woody, over 6 cm wide, nearly cylindrical, often branched, brownish-gray, and lemon-yellow when fractured.

Young branchlets are yellowish or yellowish-purple, glabrous, erect, and ridged; older branches are gray, rod-like, and covered with tripartite, occasionally five-partite or simple sturdy spines. Shortened branchlets bearing clusters of leaves develop in the axils of the spines. Leaves are thin, obovate or oval, finely toothed, 2–7 cm long and 1–4 cm wide, with a cuneate base and rounded apex, finely serrulate margins, and small stipules; each tooth extends into a soft bristle. The petiole is grooved and winged in the upper part. The inflorescence is a drooping, multi-flowered raceme. Flowers feature six yellow petaloid perianth segments, six large nectaries, and six stamens opposite the perianth segments. The fruit is a bright red, elongated-elliptical, acid berry up to 10–12 mm long. There are two brownish, matte seeds.

Distribution. It grows wild only in Crimea and the Caucasus, along dry stony slopes, river terraces, forest edges, and coastal sands of the Black Sea region, typically at altitudes from 600 to 1,700 m above sea level. The plant is also cultivated.

Harvesting. Leaves are harvested during the budding and flowering phase of the plant. Roots are dug up in autumn or spring when alkaloid content reaches its peak. To preserve natural resources, harvesting areas must be rotated. It is recommended not to repeat harvesting in the same Location more frequently than once every 10 years. To prevent depletion of the thickets, only one-fifth to one-third of the entire root system should be harvested, leaving the remainder untouched. During harvesting, the above-ground part of the bush is removed, The Root System is uncovered, and then dug up. Roots are thoroughly cleaned of soil but not washed. They are dried in well-ventilated attics, under sheds, or in dryers at a temperature of 45–50 °C.

Chemical composition of the raw material. All parts of the barberry plant contain alkaloids; the principal one is berberine, the concentration of which in the roots reaches 1.5%. The highest amount of alkaloids accumulates in the root bark. In addition, palmatine, columbamine, jatrorrhizine, berberrubine, oxycanthine, and others have been identified in them. They also contain chelidonic acid, Polysaccharides, anthocyanins, ascorbic acid, carotenoids, and phenolcarboxylic acids.

Biological activity and application. Berberine bisulfate (obtained from the roots) is used in medical practice as a choleretic agent for chronic hepatitis and cholelithiasis. Barberry leaf tincture is used for uterine hypotonia in the postpartum period and as a hemostatic agent for bleeding associated with inflammatory processes.

In homeopathy, root bark is used for uric acid diathesis, passage of calculi through the Ureters, renal or hepatic colic, Gout, and other manifestations of Protein METABOLISM disorders.

TUBERS WITH ROOTS OF SMOOTH STEPHANIA — TUBERA CUM RADICIBUS STEPHANIAE GLABRAE

Smooth stephania — Stephania glabra (Roxb.) Miers, fam. moonseed — Menispermaceae

Smooth stephania; from Greek Stephanos meaning crown; Latin glabra meaning smooth.

Plant description. A dioecious perennial liana with a large rounded tuber and thin fibrous roots growing from its lower part. The stem is glabrous, woody at the base. Leaves are large, up to 20 cm long, rounded, acuminate, with petioles longer than the leaves. Flowers are greenish-yellow, arranged in capitate, umbellate inflorescences. The fruit is a red, globose drupe with a juicy pericarp.

Distribution. The native range of stephania includes China, Indochina, and India, where its shoots can reach 10-15 m in length. Efforts to introduce and cultivate the plant are concentrated at the Batumi Botanical Garden and the Transcaucasian Zonal Research Station (Kobuleti).

Harvesting. The tubers and roots of stephania are dug up in autumn, cleaned of soil, cut into pieces, and dried in dryers at 60-80 °C.

Chemical composition. The total alkaloid content is 6-8 %. The primary alkaloid found in stephania tubers of Indian origin is gindarine (accounting for up to 30 % of the total alkaloids), while stephaglabrine (stepharine) makes up 15-18 %. Tubers cultivated in Transcaucasia contain 6-7.5 % alkaloids, one-third of which is gindarine and about 10 % is cycleanine.

Gindarine

Stephaglabrine (stepharine)

Biological activity and application. Gindarine hydrochloride is classified as a tranquilizer and is used for functional Disorders of the Central Nervous system, exhibiting sedative, mild hypnotic, and hypotensive effects. Stephaglabrine sulfate acts as an anticholinesterase agent.

UNGERNIA LEAVES — FOLIA UNGERNIAE VICTORIS

Ungernia Victoria — Ungernia victoris Uved. ex Artjushenko, family Amaryllidaceae

Ungernia victoris is named after the botanist F. Ungern-Sternberg; the Latin epithet "victoris" honors the Soviet botanist Viktor Petrovych Bochantsev.

This perennial plant grows up to 40 cm tall and features bulbs 7-12 cm in diameter, which produce seven to ten basal leaves arranged in two rows. The leaves are linear, succulent, smooth, with a blunt apex, 20-35 cm long and 24 cm wide. They emerge in spring and wither away in summer. After 1-2 months, a leafless floral scape develops, bearing an umbel of 2-11 flowers. The flowers are yellowish or yellowish-pink, featuring a pinkish-purple stripe on the inner side, and are regular and funnel-shaped.

Distribution. Ungernia victoris is an endemic species found in the mountains of Uzbekistan and Tajikistan at altitudes of 2000-2500 m above sea level.

Harvesting is carried out in April-May. The leaves are cut, sliced into pieces on the day of harvest, and quickly dried in the sun.

Chemical composition of the raw material. The leaves contain galanthamine- and lycorine-type alkaloids. The main components are galanthamine, galanthin, and lycorine (0.05-0.1 %). The alkaloid galanthamine can be classified as an indolizidine derivative.

Galanthamine

Lycorine

Biological activity and application. Galanthamine hydrobromide is a cholinesterase inhibitor used in the Treatment of myasthenia gravis, progressive muscular dystrophy (myopathy), radiculitis, and related conditions. It is effective for residual symptoms of poliomyelitis, cerebral palsy, and decreased tone in the digestive and urinary tracts.

Lycorine hydrochloride exhibits bronchodilatory effects. It is used as an expectorant for chronic and acute inflammatory processes in the lungs and Bronchi, as well as for bronchial asthma.

Galanthamine-type alkaloids can be obtained from the leaves of Ungernia sewertzowii (Folia Ungerniae sewertzowii) and the bulbs of Voronov's snowdrop (Bulbi Galanthi woronovii). The genus Leucojum (snowflake) is closely related to Voronov's snowdrop and holds great promise for The Development of new medicines.