Plants and Their Contained Alkaloids

This chapter is the inevitable miscellany devoted primarily to records of new alkaloids obtained mostly from plants not hitherto examined. Where known their structures and other pertinent data are included. 

Many of the data have been retrieved from Chemical Abstracts and the descriptions are consequently rather brief. The author s personal bias is perhaps evident in a number of instances where new knowledge of well known alkaloids is reported. Where a plant or an alkaloid has been discussed in previous volumes of The Alkaloids the volume number and page are given in parentheses following the subject heading. 

Acacia longifolia Willd. Acacia phlebophylla F. Muell.) 

A Aij-Dimethyltryptamine was the only alkaloid found in this plant 

Acronychia haplophylla Eng. (A. tetrandra F. Muell.) (Rutaceae) Acrophylline, C17H17O3N (mp 120°) (I) and acrophyllidine, C17H19O4N (mp 177°) (II). The structures were determined largely by spectroscopic methods but the hexahydro derivative of I was shown to have structure III by a synthesis. For this purpose A-acetyl-m-anisidine was alkylated with isoamyl bromide in the presence of sodium hydride in DMF. Hydrolysis gave A-isoamyl-m-anisidine which on heating to reflux temperature with diethyl malonate in diphenyl ether gave III (mp 174°) (3a). 

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Willaman, J. J. and B. Schubert, Alkaloid-Bearing Plants and Their Contained Alkaloids. U.S.D.A./A.R.S. Tech. Bull. 1234. Washington, DC, 1961. 

Willaman J J, Li H L 1970 Alkaloid-bearing plants and their contained alkaloids 1957-1968. (Suppl) J Nat Prod 33 1-286... 

Willaman JJ, Schubert BG 1961 Alkaloid bearing plants and their contained alkaloids. US Dep Agr ARS Tech Bull 1234... 

Willaman, J. J. and B. G. Schubert. 1961. Alkaloid-Bearing Plants and Their Contained Alkaloids. U.S. Department of Agriculture Technical Bulletin 1234, Washington, DC. Williamson, E. M. 2002. Major Herbs of Ayurveda. Churchill Livingstone. London. Willoughby, M. J. and S. Y. Mills. 1996. British Herbal Pharmacopoeia. British Herbal Medical Association. 

Some of the plant species contain many different alkaloids, e.g., Lunaria biennis Moench. (Cruciferaceae). The investigation of this field of plant metabolites seems to have been done randomly and not systematically. Furthermore, the occurrence of di- and polyamine derivatives in many cultivated plants is apparent (123). Their structural differences from the more complicated alkaloids are not very large. It appears very probable that many more plants and animals contain di- and polyamine alkaloids than are known today. 

C15H23NO5, Mr 297.35. A pyrrolizidine alkaloid found in some butterfly species of the family of the tiger moths (Arctiidae). The caterpillars feed on pyrro-lizidine-containing plants and store the alkaloids in their body . During pupation C. is formed in the moths by transesterification of a part of the stored pyr-rolizidine alkaloids with an acid produced by the in-... 

Similarly the class of nitrogen- and oxygen-containing organic bases isolated from plants and known as alkaloids (e.g. morphine, codeine, nicotine, quinine) was recognized in the early part of the century, and a number of pure alkaloids were isolated, but their structures defied elucidation for some time. Many of these natural products, particularly... 

Tobacco use is primarily due to psychopharmacological effects of nicotine (Henningfleld et al. 2006). Nicotine is a tobacco alkaloid, a basic substance that contains a cychc nitrogenous nucleus. In Nicotiana plants, most alkaloids are 3-pyridyl derivatives In cured leaf of Maryland Robinson Medium Broadleaf, 24 pyridine derivatives were identified, including nicotine, nomicotine, anabasine, oxynicotine, myosmine, 3-acetylpyridine, 2,3 -dipyridyl, iticotinamide, anatabine, nicotinic acid, and unidentified pyridine alkaloids of derivatives thereof (Tso 1990). Nicotine is the principal alkaloid in commercial tobacco (this was confirmed in 34 out of 65 Nicotiana species) nomicotine, rather than nicotine, appears to be the main alkaloid in 19 out of 65 species and anabasine is the third most important. In addition to the above-mentioned principal and minor alkaloids, the presence of many trace amounts of new alkaloids or their derivatives were frequently reported, including, for example, 2.4 -dipyridyl, 4,4 -dipyridyl, N -formylanabasine, A -formylanatabine, N -acetylanatabine, N -hexanoyl-nomicotine, N -octanoyl-nomicotine, T-(6-hydroxyoctanoyl) nomicotine, and l -(7-hydroxyoctanoyl) nor-nicotine. 

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