Cephaelis ipecacuanha

There is a relatively large number of alkaloids which maybe considered as simple phenethyl amine [64-04-0] (59, R = H), CgH N, or tyramine [51-67-2] (59, R = OH), CgH NO, derivatives. These iaclude mescaline (61) from the small wooly peyotyl cactus l ophophora mlliamsii (L emaire) Coult. anhalamine (62) and lophocerine (63) from other Cactaceae, and the important antamebic alkaloids (—)-protoemetiae (64), (—)-ipecoside (65), and (—)-emetine (66) from the South American straggling bush Cephaelis ipecacuanha (Brotero) Rich. AH of these bases appear to be derived from tyrosiae (25,... 

Ipecac is prepared from the dried roots and rhizomes of Cephaelis ipecacuanha (Brot.) A. Rich, and contains the alkaloids emetine [483-18-1] (17) and cephaeJine [483-17-0] (18) in a ratio between 2 1 and 4 1. It has been used extensively in cough preparations and is beheved to act by gastric reflex stimulation. Toxic effects include vomiting, irritation of the gastrointestinal tract, and cardiac arrhythmias (19). Ipecac symp is available over-the-counter in the United States only in 30-mL containers for use as an emetic in treating poisonings. 

The contribution of Rubiaceae to Western pharmaceuticals and medicine is substantial because it is the source for Uncaria gambier (Hunt.) Roxb. (Catechu, British Pharmaceutical Codex, 1963), Cephaelis ipecacuanha (Brot.) A. Rich. (uragoga ipecacuanha, Brazilian ipecacuanha), or Cephaelis acuminata Karsten (Cartagena ipecacuanha) (Ipecacuanha, British Pharmacopeia, 1963), Cinchona calisaya (yellow... 

Ipecac syrup is prepared from the dried rhizome and roots of Cephaelis ipecacuanha or Cephaelis acuminata, plants from Brazil and Central America that have the alkaloid emetine as their active principal ingredient. It acts directly on the CTZ and also indirectly by irritating the gastric mucosa. Ipecac is cardiotoxic if absorbed and can cause cardiac conduction disturbances, atrial fibrillation, or fatal myocarditis. If emesis does not occur, gastric lavage using a nasogastric tube must be performed. 

Chemical Class Cephaelis ipecacuanha derivative I Clinical Pharmacology ... 

Emetine and dehydroemetine are natural alkaloid obtained from Cephaelis ipecacuanha and synthetic analog respectively. They are effective against tissue trophozoites of . histolytica. It has no effect on cysts but effective in amoebic liver abscess also. It acts by inhibiting protein synthesis by arresting intraribosome translocation of tRNA-amino acid complex. Dehydroemetine is less toxic than emetine and very effective drug for tissue amoebiasis. It is more rapidly eliminated from the body than emetine. 

Avarol and avarone derivatives (from the Red Sea sponge Dysidea cinerea), the alkaloids psy-chotrine and O-methylpsychotrine (from ipecac, the dried rhizome and root of Cephaelis ipecacuanha), and phloroglucinol derivatives such as mallotojaponin, from the pericarps of Mallotus japonicus, have all been reported to inhibit the reverse transcriptase activity of HIV-1, noncom-petitively with respect to the natural substrate (dNTP). In neither case was the anti-HIV-1 activity determined in cell culture, so it is not clear whether any of these compounds is really an effective... 

Note The most commonly used emetics are ipecac and apomorphine. Induced emesis is the preferred means of emptying the stomach in awake patients who have ingested a toxic substance or have recently taken a drug overdose. Emesis should not be induced if there is central nervous system depression or ingestion of certain volatile hydrocarbons and caustic substances. Ipecac syrup is prepared from the dried rhizome and roots of Cephaelis ipecacuanha or of C. accuminata, plants from Brazil and Central America, in which the alkaloid emetine is its active principal ingredient. 

Emetines (Phe C6N C6N -CH2 C5N Phe) Emetine, emetamine and psy-chotrine (from Cephaelis ipecacuanha (Rubiaceae), ipecacuanha being used as an emetic and expectorant due principally to its content of emetine, a DNA-binding compound). 

Pogonopus tubulosus, Psychotria granadensis, Cephaelis ipecacuanha (Rubiaceae)... 

Tubulosine Cephaelis ipecacuanha, Pogonopus [amoebicidal, antitumour,... 

Berberis, Mahonia spp. (Berberidaceae), Jateorrhiza palmata (Menispermaceae) Papaveraceae Alangium lamarckii (Alangiaceae) [bark, root, seed], Cephaelis ipecacuanha (ipecacuanha),... 

The close biogenetic relationship of the ipecac and monoterpenoid indole alkaloids has already been reviewed in several places (3,5,117,287). In the case of the ipecac alkaloids, tracer experiments (288) have shown that labeled geraniol (146) and loganin (148) are incorporated by Cephaelis ipecacuanha into radioactive cephaeline (149) and ipecoside (150). Thus, the C9-C,0 units of the ipecac alkaloid and ipecoside, represented by thickened lines in formulas 149 and 150, are of monoterpenoid origin from geraniol (145), and loganin (147) acts as a precursor for both alkaloids. The incorporation of glycine into the C9 unit of cephaeline (2) in Cephaelis plants has also been reported (289). 

Scheme 2. Biosynthesis of ipecac, Alangium, and indole alkaloids nitrogenous portion. Pathway (a) in Cephaelis ipecacuanha pathway (b) in Alangium lamarckii.

An alkaloid present in ipecacuanha, the dried root, or rhizome and root, of Cephaelis ipecacuanha =Uragoga ipecacuanha) (Rubiaceae) or C. acuminata. 

Asperula odorata (sweet woodruff) Cephaelis ipecacuanha (ipecac) Hintonia latiflora (copalchi bark) Morinda citrifolia (non )... 

Cephaelis ipecacuanha (ipecac) Chelidonium majus (celandine) Chenopodium ambrosioides (American wormseed) Chrysanthemum vulgaris (common tansy)... 

Ipecac Cephaelis ipecacuanha Sweet vernal grass Anthoxanthum odoratum... 

Ipecacuanha is an extract of the root of Psychotria ipecacuanha, also known as Cephaelis ipecacuanha, a member of the Rubiaceae. It contains the emetic alkaloids cephaehne and emetine. It has often been used as a home remedy for various purposes, and not only as an emetic. It is a traditional ingredient of some expectorants, since expectoration often accompanies vomiting. Misuse of ipecacuanha by patients with anorexia nervosa and bulimia has resulted in severe myopathy, lethargy, eiythema, dysphagia, cardiotoxi-city, and even death. Use in infancy generally seems safe. 

Table 5. Alkaloid content (% dry weight) in the leaves of Cephaelis ipecacuanha in vitro shoots cultured on solid medium at 25 °C under 16 hr/day light (80 pEm S ) for 8 weeks...

Fig. (11). HPLC chromatogram of the leaf extract of Cephaelis ipecacuanha...

Callus and adventitious roots of ipecac (Cephaelis ipecacuanha ) were induced on the leaf segments from axenic shoot culture and their capabilities for alkaloid production were investigated [15, 52]. 

A one-year-old Cephaelis ipecacuanha plant propagated through shoot-tip culture (section 1.1) in a greenhouse accumulated ca. 2 mg emetine and ca. 2 mg cephaeline, respectively, in its roots ca. 0.2 g total dry weight). On the other hand, the root culture of ipecac cultured for 7 weeks in 50 ml MS medium containing 0.01 mg/1 5,6-Cl2-IAA yielded almost the same amounts of alkaloids, 0.6 mg emetine and 2.4 mg cephaeline. Thus the root culture of ipecac is a realistic economic source of the isoquinoline alkaloids. 

Transformation of ipecac Cephaelis ipecacuanha A. Richard) by Agrobacterium rhizogenes... 

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