Areca nut alkaloids

The saliva of betel nut chewers contains nitrosamines derived from areca nut alkaloids (4), and the use of areca nuts has been widely imphcated in the development of oral cancers. 

Nuts have many uses, both industrial and domestic. For instance, the ivory nut, or tagua, is a source material for the manufacture of buttons and turnery articles. The kola nut supplies ingredients for popular cola beverages in the United States (see Carbonated beverages). StTychnos nux-vomica provides the important medicine and poison, strychnine. The areca or betel nut is chewed by the Indian and Malayan people as a narcotic a slice of the nut is placed in a leaf of the pepper plant Piper betle) together with a pinch of lime the mixture is an acrid, astringent narcotic that dyes the mouth red, blackens and destroys the teeth. The areca nut contains, among other alkaloids, arecoline, an active anthelminthic widely used in veterinary practice for the treatment of tapeworm infections. 

Arecoline is usually stated to be present to the extent of 0-1 per cent., but Chemnitius gives the yield of hydrobromide as 0-35 to 0-4 per cent. Arecaidine and guvacine occur in smaller quantities, whilst guvacoline and arecolidine are found only in minute amounts. Alkaloidal assay processes for areca nuts have been published by Bourcet, and the National Formulary Committee, and Bond has described a method of estimation for arecoline hydrobromide. A microchemical test for the identification of arecoline has been devised by Gornyi. ... 

Guvacoline, CjHjjOjN. K. Hess assigned this name to an alkaloid, obtained by E. Merck from areca nut, which yields a hydrobromide, short prisms, m.p. 144-5°, that he identified with guvacine methyl ester hydrobromide see above). The base is a colourless oil, b.p. 114°/13 mm., which yields a hydrochloride, m.p. 121-2°, a platinichloride, m.p. 211°, and on methylation furnishes a mixture of arecoline methiodide and hydriodide (p. 12). 

Arecoline, CgHj 302N. This, the most important alkaloid of areca nut, is an odourless, alkaline oil, b.p. 209°, volatile in steam, miseible with most organic solvents and water, but extractable from the latter by ether in presence of dissolved salts. The salts are crystalline, but usually deliquescent the hydrobromide, B. HBr, forms slender prisms, m.p. 177-9°, from hot alcohol the aurichloride, B. HAUCI4, is an oil, but the platinichloride, B2. H2PtClg, m.p. 176°, crystallises from water in orange-red rhombs. The methiodide forms glancing prisms, m.p. 173-4°. 

Areca nuts (betel nuts) are the seeds of Areca catechu (Palmae/Arecaceae), a tall palm cultivated in the Indian and Asian continents. These nuts are mixed with lime, wrapped in leaves of the betel pepper (Piper betle) and then chewed for their stimulant effect, and subsequent feeling of well-being and mild intoxication. The teeth and saliva of chewers stain bright red. The major stimulant alkaloid is arecoline (up to 0.2%) (Figure 6.36), the remainder of the alkaloid content (total about 0.45%) being composed of related reduced pyridine... 

Many of the world s population (more than 200 million people worldwide) chew betel nut quid, a combination of areca nut, betel pepper leaf (from Piper betle), hme paste, and tobacco leaf. The major alkaloid of the areca nut, arecoline, can produce chohnergic adverse effects (such as bronchoconstriction) (1) as well as antagonism of anticholinergic agents (2). The lime in the betel quid causes hydrolysis of arecohne to arecaidine, a central nervous system stimulant, which accounts, together with the essential oil of the betel pepper, for the euphoric effects of chewing betel quid. 

Areca, Betel nuts pinang. Nuts (seeds) of Areca catechu L., Palmaceae. Habit. East Indies. Consiif. Areco-line, arecaidine, guvacine, guvacoline, arecolidine, choline, about 15% red tannin, about 14% fat. Reviews.- L. Marion The Alkaloids of Areca Nut in Manske-Holmes, The Alkaloids Vol. I (Academic Press, New York, 1950) pp 171-175 Raghavan. Earuah, Earn. Bot. 12, 3IS (1958). 

As early as 1886, it was discovered that the active principle of the areca nut was alkaloidal in nature (75) and since then six alkaloids from that source have been characterized they are arecoline (76), arecaidine (76), (arecaine (78)), guvacine (78), guvacoline (81), isoguvacine (79), and arecolidine (80). The structure of the first four of these has been completely elucidated, but little is known of that of arecolidine, and the homogeneity of isoguvacine is uncertain. 

Betel nut quids consist of areca nut Areca catechu) wrapped in betel vine leaf Piper betle) and smeared with a paste of burnt (slaked) lime. It is chewed for the euphoric effects of the major constituent, arecoline, a cholinergic alkaloid, which appears to be absorbed through the mucous membrane of the mouth. Arecoline has identical properties to pilocarpine and normally has only mild systemic cholinergic properties however asthmatic subjects seem to be particularly sensitive to the bronchocon-strictor effects of this alkaloid and possibly other substances contained in the nut. 

Areca alkaloids. General term for dehydro- piperi-dine alkaloids of the betel (areca) nut, the seeds of the betel palm Areca catechu (Palmae, Areceae). Pyridine alkaloids are isolated from the hemispherical, ca. 3-cm large nuts of the betel palm cultivated in India and east Asia. 

Alkaloid of areca nuts. Plates -f- IHgO from EtOH.Aq. M.p. 223-4° decomp., anhyn. 232°, Sol. HgO. Insol. most org. solvents, Dil. aq. sol. reacts neutral, cone, as weak acid. 

Shih YT, Chen PS, Wu CH, Tseng YT, Wu YC, Lo YC (2010) Arecoline, a major alkaloid of the areca nut, causes neurotoxicity through enhancement of oxidative stress and suppression of the antioxidant protective system. Free Radic Biol Med 49 1471-1479... 

Pyridine Group. Piperine, Piperovatine, Leucenol, Mimosine, Alkaloids of Ricinus communis, Foenugrec, Areca Nut, Hemlock, Lobelia, Tobacco Nicotiana spp.). Anabasis aphylla. Pomegranate Root Bark. ... 

The choline ester, carbachol, activates M-cholinoceptors, but is not hydrolyzed by AChE. Carbachol can thus be effectively employed for local application to the eye (glaucoma) and systemic administration (bowel atonia, bladder ato-nia). The alkaloids, pilocarpine (from Pilocarpus jaborandi) and arecoline (from Areca catechu betel nut) also act as direct parasympathomimetics. As tertiary amines, they moreover exert central effects. The central effect of muscarinelike substances consists of an enlivening, mild stimulation that is probably the effect desired in betel chewing, a widespread habit in South Asia. Of this group, only pilocarpine enjoys therapeutic use, which is limited to local application to the eye in glaucoma... 

The nut of the palm Areca catechu contains a mildly stimulatory alkaloid and in some Asian countries the chewing of pieces of the nut is enjoyed because of the mild euphoric state it induces. Restrictions in the use of betel nut remain rather few despite some... 

Nicotinic acid undoubtedly provides the basic skeleton for some other alkaloids. Ricinine (Figure 6.35) is a 2-pyridone structure and contains a nitrile grouping, probably formed by dehydration of a nicotinamide derivative. This alkaloid is a toxic constituent of castor oil seeds (Ricinus communis Euphorbiaceae), though the toxicity of the seeds results mainly from the polypeptide ricin (see page 434). Arecoline (Figure 6.36) is found in Betel nuts (Areca catechu Palmae/Arecaceae) and is a tetrahydronicotinic acid derivative. Betel nuts are chewed in India and Asia for the stimulant effect of arecoline. 

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