Rauwolfia Alkaloids. XIX.1 The Constitution of Deserpidine and Reserpine
01 Feb 1955-Journal of the American Chemical Society (American Chemical Society)-Vol. 77, Iss: 16, pp 1071-1072
About: This article is published in Journal of the American Chemical Society.The article was published on 1955-02-01. It has received 44 citations till now. The article focuses on the topics: Deserpidine & Rauwolfia alkaloid.
Citations
More filters
TL;DR: This review covers the literature on simple indole alkaloid and those with a nonrearranged monoterpenoid unit and newly isolated alkaloids, structure determinations, total syntheses and biological activities.
531 citations
TL;DR: The mode of action of reserpine (Serpasil) has been under intensive investigation since Miiller, Schlittler and Bein' identified this crystalline alkaloid from the crude extract of RauwolJa serpenlina Benth and clinical trials were started immediately both in the field of hypertension and psychiatric disorders.
Abstract: The mode of action of reserpine (Serpasil) has been under intensive investigation since Miiller, Schlittler and Bein' identified this crystalline alkaloid from the crude extract of RauwolJa serpenlina Benth. When it was recognized as an alkaloid principally responsible for the pharmacological action of the whole root (Bein2), clinical trials were started immediately both in the field of hypertension (e .g . Wilkins? Loefflel-') and psychiatric disorders (e .g . S a i n ~ , ~ Noce,6 Kline7). Meanwhile, the pharmacology of the new alkaloid was carefully analyzed by various groups of investigators. The general pharmacology has been discussed by Bein et aZ.B and Plummer el ~ 1 . ~ 3 l o Tripod and Meier,\" Trapold, Plummer, and Yonkman,12* l3 and Cronheim el aZ.14 analyzed some cardiovascular aspects of reserpine, whereas Tripod, Bein, and Meierl6 and Schneider and E a r P , l 7 , characterized the tranquilizing properties of reserpine and compared its effects with sedation obtained after administration of commonly used sedatives, especially the barbiturates. Recently, Gaunt el aZ.'9, 2o and Gross et a1.21 were able to give experimental evidence of the hypotensive and life-prolonging effect of reserpine in chronically induced hypertension in rats. Reserpine is not the only pharmacologically active alkaloid found in different Rauwolfia species. Klohs et a1.22 isolated rescinnamine from Rauwolfia serpentina Benth. This compound was demonstrated, by Cronheim and his
45 citations
TL;DR: In this article, a review of the stereoselective formation of organic compounds is presented, where a number of examples of such syntheses, especially those of alkaloids and steroids, are described.
Abstract: This review deals with the stereoselective formation of organic compounds. A number of examples of such syntheses, especially those of alkaloids and steroids, are described. An asymmetric synthesis, which avoids the intricacies and wastefulness of optical resolution, has been successful in a few cases only. The procedures of configurational change and of optical resolution, as well as the planning of multi-step stereoselective syntheses, are discussed.
40 citations
TL;DR: It is concluded that epimerization in these alkaloids involves initial C2 protonation according to Scheme II because 3-Deuterio-isoreserpine dedeuterates faster than it epimerizes.
38 citations
TL;DR: Active chemical and pharmacological interest in R. serpentina has resulted in the discovery of several new alkaloids, and the isolation by Muller, Schlittler, and Bein of reserpine, an alkaloid with pronounced hypotensive and sedative activity, has lent further impetus to the pharmacological and chemical study of the alkal steroids of R. Serpentina.
Abstract: Rauwolfia is an important genus of the plant family Apocynaceae. There are nearly one hundred and twenty‐five species of Rauwolfia which are distributed all over the tropical regions of the world (1‐8). The most important member of the genus is R. serpentina Benth; the crude drug was known to the ancient Indians as a useful febrifuge (8), a remedy for snake bite, and as a cure for dysentery. In more recent times it has been used for insomnia, hypochondria and insanity.
The presence of alkaloidal principles in R. serpentina was first pointed out in 1890 by Greshoff (9). In 1933, Chopra, Gupta, and Mukherjee (10) reported the hypotensive activity of the material extracted from the plant and in 1931 Siddiqui and Siddiqui (11) isolated a series of crystalline alkaloids from R. serpentina. Active chemical and pharmacological interest in R. serpentina has resulted in the discovery of several new alkaloids (Table I). The isolation by Muller, Schlittler, and Bein (12) of reserpine, an alkaloid with pronounced hypotensive and sedative activity, has lent further impetus to the pharmacological and chemical study of the alkaloids of R. serpentha. A brief summary of the chemical aspects of R. serpentina will be presented in this review.
36 citations