Chondrodendron tomentosum, alkaloids

Para, Tube or Bamboo Curare. This variety was packed in sections of bamboo, but this almost traditional information needs modification since tube curare became a commercial article. It is now a viscous, solid or even powdered extract, exported in sealed tins. In view of the relationship established between bebeerine, curine, and tubocurarhie, the active alkaloid of this variety of curare, the suggestion was made, first by Spath, Leithe and Ladeck, and more definitely by King that its botanical source should be sought among the Brazilian Menispermaceae, and as shown later the search for the source of the d-tubocurarine found in this variety of curare has been narrowed down to Chondrodendron tomentosum, or possibly a closely related species liable to be confused with it. 

Alkaloids of Chondrodendron tomentosum. Butcher has examined a curare prepared by Indians of the Upper Amazon, in which the only plant used was Chondrodendron tomentosum, Ruiz and Pavon. From it he isolated the known alkaloids, d-tjochondrodendrine (p. 365), d-wochondro-... 

These results seemed to establish with certainty that the active component of tube curare is derived from Chondrodendron tomentosum, but the matter again became doubtful when King reported that in the stems of a carefully authenticated specimen of the plant, collected at Tarapoto in Peru, he had found 1-curine and Z-tubocurarine chloride. This is the first recorded natural occurrence of the latter and seems to indicate either that the alkaloidal components of the plant are not constant in character, or that the botanical description of Chondrodendron tomentosum covers two species containing the dextro- and Icevo- quaternary alkaloids respectively. 

Chondrodendron polyanthum, 371 Chondrodendron tomentosum, 363, 371, 373, 377, 391 alkaloids, 376 Chondrodine, 363, 364 Chondrofoline, 364, 365 Chrycentrine, 172, 313 Chiysanthemine, 773 Chrysanthemum cineraricefoHum, 773 Chuchuara, 781 Chuehuhuasha, 781 Cicuta virosa, 13 Cinchamidine, 419, 429 Cinchene, 439 Cinchenine, 438, 439, 440 apoCinchenine, 440, 441 Cincholoipon, 438 Cincholoiponic acid, 438, 443 Cinchomeronic acid, 183 Cinchona alkaloid structure, synthesis, 457 Cinchona alkaloids, bactericidal action of some derivatives, 478 centres of asymmetry, 445 constitution, 435 formulae and characters of transformation products, 449, 451 general formula, 443 hydroxydihydro-bases, 448, 452-4 melting-points and specific rotations, 446... 

C-alkaloid E Chondrodendron tomentosum, calabash (curare arrow poison)... 

Curare. General name for arrow poisons produced by the Indians in tropical South America from the barks of many Strychnos species, especially S. toxifera. Other plants such as Chondrodendron tomentosum are used for the same purpose. For further names for the toxin, see Lit.. Of the 40 alkaloids contained in C., only those with two quaternary nitrogen atoms show the typical toxic action. C-Curarine I (see toxiferines) and C-dihydrotoxiferine are the most active compounds. Depending on the compositions, distinctions are made between ... 

So-called tube curares (because they are stored in bamboo tubes) often are prepared from the menispermaceous plant Chondrodendron tomentosum. These extracts are prepared and used in localized areas of the upper Amazon and Colombia. Most of the active alkaloids are bisbenzylisoquinoline alkaloids. The major alkaloid is tubocurarine (97), a quaternary species. 

Dutcher J D 1946 Curare alkaloids from Chondrodendron tomentosum Ruiz and Pavon. J Am Chem Soc 68 419-424... 

Kaul A, Ahuja MM (1980) An extensive survey for argemone contamination in rape and mustard oil seed and oil. Indian Chem J 15(1) 36-38. Cited from Chem Abstr 93 166344 (1980) King H (1935) Curare alkaloids. Part I. Tubocurarine. J Chem Soc 1381-1389 King H (1947) Curare alkaloids. Part VI. Alkaloids from Chondrodendron tomentosum R. and P. J Chem Soc 936-937... 

Full understanding is hampered by current deficiencies in our knowledge of the chemical composition of the plants concerned—for tubocurarine has so far only been found in Chondrodendron tomentosum—yet, as demonstrated by the curare formulas given in Section 1.2.3.1, there are curares from regions 2 and 3 that do not have this species as an ingredient, so that their muscle-relaxant activity must be due to alkaloids from other plants, e.g. Abuta (cf. Section 1.4.6.4) or Cur area species. 

It is (H-)-tubocurarine and its associated alkaloids that have been at the centre of interest. The monoquaternary (H-)-tubocurarine (18j) is rather less active than the parent bis-quaternary indole bases. The head-drop dose in the mouse is about 125 fig/kg and in man about 150 /tg/kg (252). In contrast, the enantiomeric (—)-tubocurarine (181) is 30-60 times weaker (354). (H-)-Chondrocurarine (18n), the fully N-methylated alkaloid and the base with the bis-quaternary structure originally assigned to (+)-tubocurarine, has almost four times the potency of that alkaloid. It is responsible for a considerable part of the activity of Chondrodendron tomentosum extracts (353). Data supposedly for 0,0 -dimethyl-(+)-tubocurarine (18m) are probably for the completely methylated AT,0,0 -trimethyl derivative (18o), since the method used for its preparation also quaternizes the tertiary nitrogen (500). The compound is two to three times more potent than (H-)-tubocurarine it is also known as metocurine and has acquired limited use in surgery as a muscle relaxant (501). The muscle-relaxant properties of quaternized curine derivatives continue to be investigated (see 345 and references cited therein). 

An isoquinoline alkaloid isolated from Chondrodendron tomentosum causes muscular relaxation more potent than its (—)-enantiomer today synthetic alternatives such as atracurium are more often used. 

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