Cinchona species

Analyses of Cinchona Barks. For galenical preparations, pharmacopoeia recognition is usually restricted to barks of cultivated cinchona species known to yield total alkaloids satisfactory in composition thus, the British Pharmacopoeia 1932 prescribes the varieties to be used, and specifies not less than 6 per cent, of total alkaloids, of which at least half must be quinine and cinchonidine, determined by the process prescribed. Numerous other processes have been published and references to the more important of these are given under the following headings —identifica-... 

Quinine is an alkaloid produced by various Cinchona species (e.g. Cinchona pubescens or fever tree), which are mainly native to South America. The bark of these trees were initially used to treat malaria. Quinine itself was subsequently isolated in 1820 and found to be toxic not only to the protozoan Plasmodium (which causes malaria) but also to several other protozoan species. 

Quinuclidine (l-azabicyclo[2.2.2]octane) is a heterocyclic system which is part of the structure of a number of natural physiologically active compounds and synthetic drugs.1 Among the natural alkaloids, the following quinoline and indole derivatives contain the quinuclidine ring cinchonine, cinchonamine (alkaloids of Cinchona species),8-12... 

Cinchona species (Rubiaceae) are sources of quinine and quinidine, containing a quinoline nucleus and derived through the extensive elaboration of strictosidine (Fig. 42). The intriguing history of the antimalarial quinine and its role in world politics over the past 350 years are legendary. It is frequently the only antimalarial drug to which patients are not resistant. Its widest use, however, is in the beverage industry in tonic water. Quinidine, an isomer of quinine, is used to treat cardiac arrythmias. 

Cinchona Ledgeri-ana, C. Calisaya and hybrids of these with other Cinchona species Botanical origin Cinchona succirubra or its hybrids Coffea arabica Coffea liberica... 

Source Cinchona pubescens Vahl (C. succirubra Pav. ex Klotzsch) and other Cinchona species (Rubiaceae). 

Quinoline is a high-boiling liquid isoquinoUne is a low-melting solid each has a sweetish odour. Both bases have been known for a long time quinoline was first isolated from coal tar in 1834, isoquinoUne from the same source in 1885. Shortly after the isolation of quinoline from coal tar, it was also recognised as a pyrolytic degradation product of cinchonamine, an alkaloid closely related to quinine, from which the name quinoline is derived the word quinine, in turn, derives from quina, a Spanish version of a local South American name for the bark of quinine-containing Cinchona species. 

The inheritance of alkaloids in Cinchona species has been the subject of an extensive program (230). If two Solanum species containing demis-sine and solanine, respectively, are hybridized a plant results which elaborates both alkaloids (231). 

Cinchona species have not been extensively studied. One such... 

Cinchona can be considered to be recalcitrant with regard to cell and tissue culture. Although it has been possible to obtain cell and tissue cultures of some Cinchona species, they often require special treatments also, growth is usually slow, and viability of cells is rapidly lost. Moreover, the cell cultures are poor producers of alkaloids. In order to arrive at... 

CkiehonkMiie [(85,9/()-cinchonan-9-ol]. Formula, see quinine. C,9H22N20, Mr 294.40 plates or prisms, mp. 2I0 C, (a][) -110 (C2H5OH) well soluble in alcohol and chloroform. C. is an alkaloid of the Cinchona group ( Cinchona alkaloid), a quinoline alkaloid. C. is isolated from many Cinchona species (C. tucujensis, C. pubescens) and also occurs in Remijia species (Ruhi-aceae) and in some members of the olive family such as Olea europaea (olive tree) and Ligustrum vulgare (common privet). C. is obtained commercially from cinchona bark. 

Papaver somniferum Cinchona species Atropa belladonna Hyoscyamus niger Datura stramonium Catharanthus roseus Digitalis lanata... 

Among others in our laboratories cell and tissue cultures of Cinchona species have been initiated. For a review of this work is referred to Wijnsma and Verpoorte (29). Summarizing the results cell suspension cultures of Cinchona are very poor producers of alkaloids. With an increase of organisation of the culture an increase of the alkaloid production can be observed (Fig. 2). 

R. Wijnsma and R. Verpoorte, Quinoline alkaloids in cell and tissue cultures of Cinchona species. Cell cultures and somatic genetics of plants. Vol. 5. 

R. Wijnsma, T.B. van Vliet, P.A.A. Harkes, H.J. van Groningen, R. van der Heijden, R. Verpoorte and A. Baerheim Svendsen, An improved method for the extraction of alkaloids from cell and tissue cultures of Cinchona species. Plants Medics, 53 (1987) 80-84. 

As is true for the naphthoquinones, anthraquinones are synthesized by a variety of routes in plants and fimgi (Pack-ter, 1980). Most are derived from either acetate-malonate or isochorismate-a-ketoglutaric acid-mevalonate pathways. Anthraquinones also are produced frequently in plant tissue cultures (Ellis, 1988). Tissue cultures of Cinchona species (Rubiaceae) produce at least 30 different anthraquinones. 

Several alkaloids of Cinchona species [e.g., quinine (66), quinidine (73), cinchonidine (68), and cinchonine (67)] serve as feeding deterrents to Syntomis larvae (Lepidoptera), bees, Leptinotarsa (Coleoptera), Locusta, Agelaius, and a variety of other organisms (Wink, 1993). The presence of quinine sulfate or chloride at 4 X 10 or 1.5 X 10 M reduced... 

Certain insects that feed on Cinchona species appear to accumulate the alkaloids in their bodies. For example, a Hel-opeltis species mdAttacus atlas both accumulate cinchonine (67) or cinchonine-like alkaloids (Waller and Nowacki, 1978). 

The molecules of alkaloids belonging to the group of cinchonine-cinchonamine [4-6] (alkaloids of Cinchona species), sarpagine-ajmaline (Rauwolfia alkaloids) [4,7] and to that of makuzine (Strychnos alkaloids) [8,9] contain the quinuclidine... 

Cinchona plants yielded a crucial phytochemical resource to nineteenth century European people involved in trade and colonization of tropical lands - quinine [52], Before quinine, malaria was a major health issue in the new world, lowering quality of life by causing severe discomfort and even death. Quinine is an alkaloid present in the bark of several Cinchona species known as quina quina by native populations. It is most concentrated in Cinchona calisaya however, the most widely known quina quina plant became Cinchona officinalis officinalis means medical herb ). Besides quinine, Cinchona plants produce other antimalarial alkaloids, namely, quinidine, cinchonine, and cinchonidine. Cinchona alkaloids can be found in other Rubiaceae genera as well, as described for Remijia peruviana [53], Cinchona alkaloids have other bioactivities besides antimalarial. Quinine has been used to treat cramps [54]. Cinchonine is an inhibitor of MDR [55]. MDR is a detoxification mechanism present in certain cancer cell lines that renders them less sensitive to chemotherapeutic medications. Administration of cinchonine along with chemotherapeutic agents would result in better efficiency of treatment oti MDR cancer cells. 

---