Rutaceae family

Rutaceae family (11) have a one-carbon-substituent at position 3 of the carbazole nucleus and an oxygen substituent at position 1 or 2. The structure of these alkaloids can vary from simple substituted carbazoles to molecules containing complex terpene moieties. 

The second type of quinohne alkaloid, found especially found in the Rutaceae family, has a as anthranilic acid. Typical compounds from this group are eduli-tine, halfordamine, folifidine, folinine, casimiroin, fohosidine and swietenidine. The /3 is 3-carboxyquinoline and the A is graveoline in the case of those alkaloids from Ruta angustifolia. 

Quinoline alkaloids from the Rutaceae family (a = L-anthranilic acid) show antimicrobial activity. Moreover, quinoline alkaloids of the Haplophyllum species are known for their powerful biological properties. For example, skim-mianine has sedative, hypothermic and antidiuretic uses. Haplophyllidine is a strong depressant of the CNS. 

Another large group of isoquinoline alkaloids are the alkoxybenzo[a]-phenanthridines. They occur most frequently in the Fumariaceae, the Papaveraceae, and the Rutaceae families. Their close botanical relationship with the... 

The common citrus fruits belong to three genera, Citrus, Poncirus (trifoliate orange), and Fortunella (in the Rutacea family) (Castle, 1987). Hereafter, citrus will refer to any or all of these three genera. The citrus tree is a native of Southeast Asia (Woodhead, 1981). 

The acridone alkaloids constitute a small group of natural products found exclusively in the Rutaceae family of higher plants. A sustained interest in this field has been due to the reported activity of acronycine a constituent of Acronnychia baueri and Vepris amphody as an anti-tumor agent. 

Linalool and linalyl acetate are the intensively studied chiral monoterpenoids. Their enantiomeric ratio had been investigated in the precious bergamot oil [36-38], lavender oils [39], and many other plants used as fragrance and flavour materials mainly fi-om Labiatae and Rutaceae families [40-42]. 

An interesting variability is observed in plants from Rutaceae family. In bergamot (Citrus auranthium Bergamia), neroli and petitgrain (Citrus auranhtium ssp. amara), and lime oils (Citrus aurantifolia) the prevalence of (-)-linalool has been found. In orange (Citrus sinensis) and tangerine (Citrus reticulata) (+)-linalool is the dominant enantiomer, while in lemon (Citrus limon) and grapefruit (Citrus paradisi) the enantiomeric ratio of linalool is close to racemate [31,40]. 

These two monocyclic terpene alcohols also occur in many essential oils but not in large quantities. Their enantiomeric composition has been investigated in essential oils from Rutaceae family, essential oils from Madagascar and many others [31,33,35,49-51]. 

Since the main work (C.C.C. 2nd edn., Vol.lVG, Ch.31. pp 171-255) was written interest in this group of natural products has continued apace. Many new alkaloids have been Isolated and their structures determined principally by H-and C-n.m.r. spectroscopy, and by part syntheses from known alkaloids. In addition "new" plants of the Rutacea family have been examined and found to contain familiar structures. A measure of this latter activity is provided by the Tables 1 - 6 in which extractives of established structure present in these plants are listed. 

Polyenamides from Compositae, Piperaceae and Rutaceae families... 

Plants of the Compositae, Piperaceae and Rutaceae families [2] have been used as ingredients in many medicinal preparations and as food spices and many of them are used as insecticides [6]. Several long-chain unsaturated amides have been isolated from these plants, and they can be classified into two main structural types (a) (2 , 4 )-dienamides derived from straight-chain fatty acids and isobutylamine, pyrrolidine or piperidine units (1-22) (Chart 1), and (b) amides with the piperonal unit derived mainly from piperic acid in combination with the above mentioned amines (23-34) (Chart 2). 

Acronycine (1.) is a natural alkaloid which was first isolated in 1948 from the bark of a small Australian Rutaceous tree, Acronychia baueri Schott (1). Since that time, the status of this plant within the Rutaceae family has been revised several times, in the course of successive taxonomic studies (2-5). It is now widely accepted that the plant belongs to the genus Sarcomelicope and should be named Sarcomelicope simplicifolia (Endl.) Hartley ssp. simplicifolia (4). 

The alkaloids sanguinarine and chelerythiine are in most cases accompanied by the minor alkaloids chelirubine, chelilutine, sanguilutine, sangui-rubine, and, in several plants, macarpine. These minor alkaloids have never been found in the Rutaceae family. In contrast, alkaloids of the nitidine type occur exclusively in the Rutaceae and are one of the chemotaxonomic features of some genera. 

Addendum. A comprehensive review on the occurrence of alkaloids in the Rutaceae family has appeared. The broad spectrum of alkaloid types, including quinolines, furoquinolines, and acridones, may be appreciated from the list of species given in this review. 

Demethylation of acid-sensitive aryl methyl ethers, such as 2,4-dimethoxyquinolines, can be accomplished using a trimethylsilyl iodide/DMAP reagent system, where DMAP is used as a Lewis base to prevent protonation of the alkene from the HIby-product. This reaction was utilized to form the quinoline-containing alkaloid natural product, atanine, from the Rutaceae family. 

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