Molecular Geometry of Alkaloids Present in Seeds of Mexican Prickly Poppy
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MOLECULAR GEOMETRY OF ALKALOIDS PRESENT IN SEEDS OF MEXICAN PRICKLY POPPY Ricardo Gobato [[email protected]] Secretaria de Estado da Educação do Paraná (SEED/PR) Av. Maringá, 290, Jardim Dom Bosco, Londrina/PR, 86060-000, Brasil. Desire Francine Gobato Fedrigo [[email protected]] Panoramic Residence, Rua Uruguai, 1380, ap. 405, Parque Jardim America, Centro, Londrina/PR, 86010-210, Brasil Alekssander Gobato [[email protected]] Faculdade Pitágoras Londrina Rua Edwy Taques de Araújo, 1100, Gleba Palhano, Londrina/PR, 86047-500, Brasil. ABSTRACT The work is a study of the geometry of the molecules via molecular mechanics of the main alkaloids found in the seeds of Argemone Mexicana Linn, a prickly poppy, which is considered one of the most important species of plants in traditional Mexican and Indian medicine system. The seeds have toxic properties as well as bactericide, hallucinogenic, fungicide, insecticide, in isoquinolines and sanguinarine alkaloids such as berberine. A computational study of the molecular geometry of the molecules through molecular mechanics of the main alkaloids compounds present in plant seeds is described in a computer simulation. The plant has active ingredients compounds: allocryptopine, berberine, chelerythrine, copsitine, dihydrosanguinarine, protopine and sanguinarine. The studied alkaloids form two groups having similar charge distribution among themselves, which have dipole moments of these two times higher than in the other group. Keywords: Alkaloids, Argemone Mexicana Linn, Bactericidal, Fungicide, Hallucinogenic, Insecticide, Molecular Geometry, Prickly Poppy, Toxic. Contents 3.5 Dihydrosanguinarine . 6 3.6 Protopine . 6 Introduction 1 3.7 Sanguinarine . 6 1 The plant 2 4 Discussion and conclusions 6 1.1 Argemone Mexicana Linn . 2 Figures 7 1.2 History . 2 Acknowledgments 11 1.3 Ethnobotany and anthropology . 3 References 11 1.4 Current use . 3 1.5 Toxicity . 3 Introduction 2 Fundamentals 4 2.1 Introduction to Molecular Mechanics . 4 The Mexican Argemone Linn popularly known as 2.2 Steric Energy . .4 Mexican poppy, Mexican prickly poppy, thistle or holy 2.3 Geometry Optimization . 4 thistle [1] is a species of poppy found in Mexico and 3 Chemical formula and physico-chemical properties widespread in various parts of the world. It is an of the active ingredients 5 extremely resistant, tolerant to drought and poor soils 3.1 Allocryptopine . 5 plant, often being the only vegetation in the soil. It has 3.2 Berberine . 5 bright yellow latex, and although toxic to grazing 3.3 Chelerythrine . 5 animals, is rarely ingested [2]. The Family 3.4 Copsitine . .5 Papaveraceae, informally known as poppies, is an important ethnopharmacological family of 44 genera and bristly capsules containing seeds and resembling and about 760 species of flowering plants. The plant is black mustard seeds. A native of America, it has run the source of many types of chemical compounds such wild into many other countries including India. The as flavonoids, although the alkaloids are the most seeds yield from 22 to 36 per cent of nauseous, bitter, commonly found. In the pharmaceutical efficacy of non-edible oil, which is considered a remedy for skin certain parts of the plant also show toxic effects [3]. It diseases. In small amounts (1-2 ml.) it is a cathartic is used in different parts of the world, for treatment of and in larger doses it causes violent purging and various diseases, including tumors, warts, skin vomiting. The seeds are sometimes found mixed with diseases, rheumatism, inflammations, jaundice, black mustard. Adulteration of edible mustard oil with leprosy, microbial infections, malaria [3] agrobacteria argemone oil is probably responsible for outbreaks of [4], mong others, and as a larvicide against the Aedes epidermic dropsy [13, 14]. Its presence in aegypti, the dengue vector [5, 6]. Structurally, concentrations of 0.2 per cent or lessis detected by polyphenols or phenolic have one or more aromatic the rich orange-red colour which appears when rings with hydroxyl groups and may occur as simple concentrated nitric acid is added to the oil or its and complex molecules. The flavonoids are subgroups mixtures, or by the ferric chloride test [15, 16]. The of polyphenols [3, 7]. The sanguinarine and berberine plant contains barberine and protopine [17]. The have a wide range of biological and / or seeds also are considered to have a medicinal value, as pharmacological properties, including anti- a laxative, emetic, expectorant and demulcent; taken inflammatory, respiratory stimulation, transient in large quantities, they are said to be poisonous. The hypotension, convulsions, uterine contraction, yellow juice which exudes when the plant is damaged antiaritmica property, positive inotropic, is used externally in scabies, dropsy, jaundice, adrenocorticotropic hormone activity and analgesic cutaneous affections and ophthalmic. The oil is effect [8]. Because of its quaternary nitrogen atom considered to be a purgative and is also used for and planar polycyclic structure, sanguinarine and cutaneous affections. [18] berberine can react with nucleophilic amino acids and anionic groups of different biomolecules, receptors and enzymes. For example, these alkaloids bind to microtubules, inhibit various enzymes including sodium-potassium-ATPase, promoting oxidative phosphorylation and are able to intercalate in DNA regions rich in guanine-cytosine [8]. Contents of alkaloids in the seeds of Argemone mexicana in percentage, total alkaloids 0.13%, diidrosanguinarine 87.00%, sanguinarine 5.00%, berberine 0.57%, protopine 0.34%, chelerythrine 0.12% and coptisine 0.03%. [9] 1. The plant 1.1 Argemone Mexicana Linn The Argemone Mexican Linn, family: Papaveraceae, genius: Argemone, species: Mexicana, common names: Amapolas del campo, Bermuda Thistle, Bird-in- the-bush, Brahmadanti, Cardo Santo, Caruancho, Chadron, Flowering Thistle, Gamboge Thistle, Gold Thistle of Peru, Hierba Loca, Jamaican Thistle, Kawinchu, Mexican Prickly Poppy, Mexican Thistle, Mexican Thorn Poppy, Prickly Pepper, Prickly Poppy, Queen Thistle, Satayanasi, Shate, Svarnasiri, Thistle- bush, xate, Yellow Thistle, Zebe Dragon. [10, 11] Figure 1. Photo papaveraceae plant, Argemone Mexicana Common Indian names: Linn Hindi: Shialkanta, Satyanashi; Gujrati: Darudi; Danarese: Balurakkisa, Datturi, Pirangi, datturi; 1.2 History Marathi: Daruri, Firangikote-pavola, dhotara; Sanskrit: The Florentine Codex, in the sixteenth century, Brahmadandi, Pitopushpa, Srigalkanta, Svarnakshiri; indicated for sore eyes. In the same century, Francisco Malyalam: Ponnummattu, Kantankattiri; Tamil: Hernandez he says: “evacuates all moods, mainly Kutiyotti, Ponnummuttai; Telugu: Brahmadandicettu. pituitous and damaging the joints, cure inflammation [12] of the eyes, is effective against fevers accesses, heals An annual with prickly leaves, bright yellow flowers, ulcers sexual parts, scabies, dissolves clouds eyes, consume superfluous flesh and calm the pain of boiled, often bathe drinkers (alcohol) that have migraine.” In the late eighteenth century, Vicente irritated skin. For use as a laxative, the seeds are Cervantes tells that “purges pituitous moods, relieves boiled. It is also reported useful in the treatment of inflammation of the eyes and dissipates the clouds bile, toothache, colic in children (newborn colic V.) which begin to form in them.” [11] The Mexican expulsion of placenta, flow, wounds and ulcers, kidney Society of Natural History records it as antidiarrheal, pain, diabetes, skin infections, pimples, spots, rashes, anti-dysentery, anti-gonorrhoeal, astringent, eye inflammation, malaria, convulsions, spasms, infection diseases, diuretic, emeto-cathartic, hypnotic, chest, and bleeding, as a purgative and healing. [10, 11] hair tonic and analgesic, for cafalalgias, dermatosis. Later, Francisco Flores slogan use for simple 1.4 Current use conjunctivitis, combat the emerging leucome, The Argemone Mexicana Linn is used as a medicinal nephelion eyes, chemosis and as a sedative. In the plant in several countries. In Mexico the seeds are same years that Flores, Eleuterio Gonzalez considered an antidote to the poison of the snakes in appointment to cure clouds corneal against headaches India while the smoke of the seeds are used to relieve as work as a lever and soothing to wash the head and toothache. The extract fresh seeds contain substances thus is bornhair, and as a drastic purgative[11]. In the that dissolve the protein and is effective in the twentieth century, Narciso Souza describes their use treatment of warts, herpes sores, skin infections, skin for diseases of the pancreas liver, lack of appetite, as diseases, itching and also in the treatment of an emetic and purgative, for eye inflammation and dropsy and jaundice [19]. Also in India the plant is skin diseases. Make attributed pectoral properties and used in Ayurvedic and Unani medicine for the soporific. Around the same time that Souza, Luis treatment of a wide range of diseases including Cabrera registers as antitussive, hypnotic and cough malaria. The use against malaria is also widespread in whooping. Finally, the Pharmaceutical Society of several African countries, including Benin, Mali and Mexico mentions its use as anti-escabiotic, Sudan [20]. There is no documentation of the antispasmodic, antitussive, cathartic, dermatosis, psychoactive properties the plant. From the emeto-cathartic, hypnotic, pectoral and sedative. [11] information contained in the websites it shows that the leaves