Leaves alkaloids

Clematis angitslifolia, 780 Coca leaves, alkaloids, 92 Cocaethyline, 96 Cocaine, 79, 92, 93, 99, 100 detection, 94 homologues, 90... 

Khat Catha edulis Leaves Alkaloids cathinone, cathine Chewed, tea Stimulant Yemenis, Ethiopians, Somalis etc. East Arabia, East Africa, Madagascar... 

We will then leave alkaloids and move back in time to a target that became important in the 1960 s, Cecropia juvenile hormone (Introduction-5). Approaches to this deceptively simple structure constitute a study in stereoselective tri-substituted olefin synthesis. Given the importance of olefins (both synthesis and chemistry of) to modern organic synthesis, I think that a visit to this old topic will be instructive, and will help set the stage for a discussion of targets of more contemporary interest. In addition, it will focus on the important role synthesis plays in structure determination, and the stimulus natural products can provide for the development of new synthetic methodology. 

Goodbody and co-workers (7/9) have examined the production of alkaloids in root and shoot cultures induced from seedlings of C. roseus. The pattern of alkaloids in the root cultures was similar to that of the roots from intact plants. Thus ajmalicine (39) and catharanthine (4) were produced, but no vindoline (3), a major leaf alkaloid, and no bisindole alkaloids. Similarly, the pattern of the alkaloid content of the shoot cultures was like that of the leaves of the intact plant, showing the presence of vindoline (3), catharanthine (4), and ajmalicine (39), with 3 predominating. A search for the bisindole alkaloids in the cultures indicated the presence of anhydrovinblastine (8) and leurosine (11) in the shoot cultures (2.6 and 0.3 xg/g fresh weight, respectively), but no vinblastine (1) or vincristine (2). 

Hoft, M., Verpoorte, R. and Beck, E. 1998. Leaf alkaloid contents of Tabernae-montana pachysiphon as influenced by endogenous and environmental factors in the natural habitat. Planta Medica, 64 148-152. 

Jones CG, Firn RD. (1991). On the evolution of plant secondary chemical diversity. The Philosophical Transactions of the Royal Society, 333, 273-80. Despite the overwhelming evidence that most NPs possess no potent, specific biological activity, NP researchers often imply the opposite by using generalisations that imply the opposite. For example, leaf alkaloids... 

Emilia sonchifolia (L.) DC Zi Bei Cao (Red tasselflower) (leaf) Alkaloids.63 For dysentery, phthisis, coughs, a detoxicant, diuretic, febrifuge. 

Hyoscyamus bohemicus F. W. Schmidt H. niger L. Liang Shi (Henbane) (root, leaf) Alkaloid, hyoscyamine, hyoscine, scopolomine, hyoscypierin, choline, mucilage, albumin.60,144,450 This herb is toxic. Antispasmodic activity. 

Other isolation studies are summarized in Table l 2-7 five new alkaloids have been obtained this year. Cell suspension cultures of Baptisia australis, Lupinus polyphyllus, and Sarothamnus scoparius produce lower yields of alkaloids than the differentiated plants, with lupanine as the main component8 (cj Vol. 11, p. 63). Examination of the leaf alkaloids of B. australis by g.l.c. and by g.l.c.-m.s. resulted in the identification of eleven constituents, including two new alkaloids.2 The structures and the distribution of some quinolizidine alkaloids that may be used as systematic markers in the Leguminosae have now been supplemented by more recent data.9... 

A wide variety of alkaloids has been encountered in the bark of Aspidosperma quebrachoblanco (see Table I). An investigation of the leaf alkaloids yielded a new base, quebrachidine (CCCXXXVIII-D, 179b), whose UV- (A 242, 290) and NMR-spectra were indicative of a dihydroindole unsubstituted in the benzene ring, while the IR-spectrum showed the presence also of the groupings NH, OH, and CO2R. The NMR-spectrum further indicated that the ester was a carbomethoxyl group... 

Bhattacharyya and Serur established the structures of delbine (54), m.p. 229-231°C, and montrifoline (56), m.p. 191-193°C, the leaf alkaloids of Monnieria trifolia direct comparison of delbine with heliparvifoline (55), m.p. 245-247°C, showed that the compounds were not identical (cf. Vol. 12, p.86). Clearly unaware of the... 

Drug sample I Vinca minor (fresh leafs), (alkaloid extraction method C, 40 [U)... 

Full details are also available of the structure elucidation of elaeokanines A-E, and elaeokanidines A-C, the leaf alkaloids of E. kaniensis Schltr. further, the structures of elaeokanines A-C have been confirmed by synthesis. The reaction of the diazoketone prepared from butyroyl chloride and diazomethane with pyrrole in the presence of copper powder gave the ketone (9), which was hydrogenated to the basic pyrrolidine ketone (10). Michael addition of ethyl acrylate... 

DasGupta S, Ray AB, Bhattacharya SK, Bose R 1979 Constituents of Pachygone ovata and pharmacological action of its major leaf alkaloid. J Nat Prod 42 399-406... 

Moody JO, Sofowora EA 1984 Leaf alkaloids of Zanthoxylum rubescens, Planta Med 50 101-103... 

The concentration of alkaloids, as well as the specific area of occurrence or localization within the plant or animal, can vary enormously. Thus the amount of nicotine [54-11-5] (21), C2QH24N2, apparentiy synthesized ia the roots of various species of JSHcotiana and subsequentiy translocated to the leaves varies with soil conditions, moisture, extent of cultivation, season of harvest, etc and may be as high as 8% of the dry leaf, whereas the amount of morphine (2, R = H) ia cerebrospiaal duid is of the order of 2 to 339 fmol/mL (23). 

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. 

The best source of the alkaloids is commercial nicotine or the concentrated tobacco extracts, used as horticultural insecticides. The average alkaloidal content of tobacco leaf is about 4,- and does not as a rule exceed 6, per cent. In 1,026 parts of the total alkaloids of Kentucky tobacco, Pictet and Rotschy found nicoteine 20, nicotimine 5 and nicotelline 1, the rest being nicotine, but, as Markwood has pointed out. 

A variety of chemicals may be leached from the aerial portions of plants by rainwater or by fog-drip (16) including organic acids, sugars, amino acids, pectic substances, gibberellic acids, terpenoids, alkaloids, and phenolic compounds. Colton and Einhellig (17) suggested that leaf leachates of velvetleaf (Abutilon theophrasti) may be inhibitory to soybean (Glycine maxT We have recently discovered specialized hairs on the stems of velvetleaf plants which exude toxic chemicals. 

Elder leaves contain the alkaloid sambucine, a precursor of hydrocyanic acid, which is somewhat toxic. Thus, the leaves are used only topically in ointments for sprains or bruises. Bruised leaves can be rubbed on the body or worn under a hat to prevent being pestered by insects. Cooled strained leaf tea can be applied to plants to discourage aphids. 

The coca leaf is either consumed by the natives of South America or exported to other countries for consumption. Another use of the coca leaf is in the extraction of cocaine either for illegitimate or legitimate use. The majority of the legal and/or clandestine cocaine factories are in South America due to the cost and bulk of transporting the whole leaf. In 1961, Bolivia produced an annual crop of from 12,000 to 18,000 tons of leaves although only half reached the legal market. The alkaloid cocaine is extracted from the coca leaf in basically three different chemical procedures. These procedures are used both in licit and illicit labs in the production of cocaine. 

Once the cocaine has been legally produced from the coca leaf, it is exported to various countries for medicinal use, basically as a topical local anesthetic (applied to the surface, not injected, only treating a particular area). In the United States the crystalline powder is imported to pharmaceutical companies who process and package the cocaine for medical use. Merck Pharmaceutical Company and Mallinckrodt Chemical Works distribute cocaine in crystalline form (Hydrochloride Salt) in dark colored glass bottles to pharmacies and hospitals throughout the United States. Cocaine, in the alkaloid form (base drug containing no additives such as hydrochloride in the crystalline form) is rarely used for medicinal purposes. Cocaine hydrochloride crystals or flakes come in Vs, A and 1 ounce bottles from the manufacturer and has a wholesale price of approximately 20 to 25 per ounce (100% pure). 

Two classes of dendrobatid alkaloids have potential dietary sources. The first are the pyrrolizidine oximes (32), whose carbon skeleton is identical to that of nitropolyzonamine, an alkaloid from a small millipede (33). Indeed, raising the dendrobatid frog D. auratus in Panama on leaf-litter arthropods, gathered weekly, resulted in skin levels of the... 

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