The Citrus (syn. Rue) botanical family (Rutaceae Juss.) contains more than 150 genera and over 900 species (Table 6). The distribution of these species is worldwide across tropical and sub-tropical areas. Many species contain both anthranilic
Definition, Typology and Occurrence of Alkaloids Table 6 General botanical characteristics of the Citrus family312,313,316,318
Botanical Forms and Parts
Some typical genera
Special characteristics Leaves
Shrubs Shrublets Trees Herbs
Usually aromatic with resinous tissues
Dotted with translucent in oil glands
Bisexual or unisexual
Ovary superior, usually syncarpous
Samara or berry acid (Figure 13) and L-histidine (Figure 14) derived alkaloids. Anthranilic acid-derived alkaloids are dictamnine, skimmianine (in such species as Dicta-mus albus or Skimmia japonica), acronycine in Acronychia baueri, melicop-icine in Melicope fareana, and rutacridone in Ruta graveolens. In the genus
L-anthranilic acid co2h
Figure 13. L-anthranilic acid is a precursor of quinazoline, quinoline and acridine alkaloids.
ch2 I 2
Figure 14. L-histidine is a precursor of imidazole alkaloids.
Haplophyllum A. Juss., a lot of alkaloids with potential estrogenic activity were reported54. These are acutine, acetylfolifidine, bucharidine, dubinidine, dubinine, glycoperine, evoxine, y-fagarine, folifidine, foliosidine, haplophyline, haplopine, perfamine and skimmianine. Moura et al.56 reported on alkaloids from Helietta longifoliata Britt., a Rutaceae family plant, which grows in South America and is used in Brazilian folk medicine. Helietidine, y-fagarine, flindrsine, kokusaginine and maculasine have been isolated and their antibacterial activity demonstrated. Alkaloids derived from L-histidine are, for example, pilocarpine and pilosine, in such species as Pilocarpus microphyllus and Pilocarpus jaborandi. Recent investigation has described fagaronine, the alkaloid extracted from Fagara zan-thoxyloides Lam. There is evidence that this alkaloid induces erythroleukemic cell differentiation by gene activation85.
From Zanthoxylum integrifolium Merr., an evergreen tree which grows in the northern Philippines and Taiwan, three new alkaloids have recently been isolated: 7,8-dehydro-1-methoxyrutaecarpine, isodecarpine and 8-demethyloxychelerythine&6. In earlier studies 1-hydroxyrutaecarpine, rutae-carpine and 1-methoxyrutaecarpine have been reported from this plant87. In Zanthoxylum hyemaline St. Hill two quinoline alkaloids (—)-R-geilbalansine and hyemaline were isolated56. Bioassay-guided fractionation led to the isolation of three indolopyridoquinazoline alkaloids, 1-hydroxy rutaecarpine, rutaecarpine and 1-metoxyrutaecarpine, from the fruit of Z. integrifolium8. Moreover, Melicope semecarpifolia produces melicarpine and samecarpine88. The genera Toddalia, Dictamus, Pelea and Stauranthus were also present in these furoguinoline alkaloids89'90'91'92'93'94'95. Galipea officinalis Hancock, a shrub growing in tropical America and used in folk medicine as an antispasmodic, antipyreti, astringent and tonic96'97'98, yields nine quinoline alkaloids, of which galipine, cusparine, cuspareine, demethoxycusparine and galipinine are the most important99. The fruits of Evodia officinalis, which has traditionally been used as a folk medicine in Korea for the treatment of gastrointestinal disorders, postpartum haemorrhage and amenorrhea, contain six quinoline alkaloids: (2-hydroxy-4-methoxy)-3-(3'-methyl-2/-butenyl)-quinoline, evocarpine, dihydroevocarpine, evodiamine, rutaecarpine, and
1-methyl-2-[(Z)-6-undecenyl]-4(1H)-quinolone100. In addition, the fruits of the similar species, Evodia rutaecarpa, contain four quinolone alkaloids:
1-methyl-2-tetradecyl-4(1H)-quinolone, evocarpine, 1-methyl-2-[(4Z,7Z)-4,7-decadienyl]-4(1H)-quinolone and 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl]-4(1H)-quinolone101. Alkaloids occurring in E. rutaecarpa show various bioactivities, including angiotensin II antagonistic effects, an inhibitory effect on Helicobacter pyroli growth, and DGAT inhibition activity. Moreover, Rah-mani et al.102 reported on the new carbazole alkaloid 7-methoxy-glycomaurin, discovered in Glycosmis rupestris Ridely. Rahman and Gray103 reported on carbazole alkaloids from Murraya koenigii (L.) Spreng., a small tree with dark grey bark, which grows in Asia. Mahanimbine has been reported to possess insecti-cidal and antimicrobial properties103 104. The isolation and identification of six
2-alkyl-4(1H)-quinolone alkaloids from the leaves of previously uninvestigated Spathelia excelsa (K. Krause) has been described by Lima et al.105. These data have chemosystematic significance in order to clarify the relationships of this species and Rutaceae plant family. Moreover, a new carbazole alkaloid, named clausine Z, has been isolated from stems and leaves of Clausena excavata Burm. by Potterat et al.106. Clausine structure was established by spectroscopic methods and its bioactivity was determined. According to Potterat et al.106 this compound exhibits inhibitory activity against cyclin-dependent kinase 5 (CDK5) and shows protective effects on cerebellar granule neurons in vitro.
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