Serpine-a new isomeride of yohimbine isolated from Rauwolfia serpentina Benth.
TL;DR: Durch Dehydrierung des Serpins mit Selenstaub wurde Yobyrin, das sogenannte «Tetrabyrin» und KetoyobyrIn gebildet, ergab sich die Konstitutionsformel des Serpin.
Abstract: AusRauwolfia serpentina Benth. wurde das neue Alkaloid Serpin, C21H26O3N2, Smp. 213–14°, isoliert. Es ist mit Yohimbin isomer. Das Alkaloid enthalt eine-OH- und eine -COOCH3-Gruppe. Das I.R.-Spektrum des Serpins zeigt die typische -COOMe-Bande (5,80µ). Eine Iminogruppierung -NH wird durch die intensive 2,95-µ-Bande verursacht. Bei der Bande bei 2,75µ handelt es sich um eine Hydroxyl-Gruppierung. Nach seinem UV.-Spektrum und IR.-Spektrum handelt es sich um ein Indolalkaloid. Durch Dehydrierung des Serpins mit Selenstaub wurdeYobyrin, das sogenannte «Tetrabyrin» undKetoyobyrin gebildet. Aus diesen Spaltstukken ergab sich die Konstitutionsformel des Serpins.
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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
TL;DR: Certain correlations are discernible and may be used by the plant chemist as first approximations of the types of materials he may expect in the analysis of previously unstudied genera.
Abstract: Of the 200 alkaloids in the relatively well-studied Apocynaceae, only 75 have had sufficient chemical investigation to permit their structural identity. Nonetheless, certain correlations are discernible and may be used by the plant chemist as first approximations of the types of materials he may expect in the analysis of previously unstudied genera.
21 citations
TL;DR: Although rauwolfia may ultimately not survive to take its place alongside the solanaceous drugs, the cardiac glycosides and opium, a study of its properties seems likely to lead to a clearer understanding of the complex mechanism underlying hypertensive disease in man.
Abstract: OVER the past two or three decades much attention has been paid by clinicians to the treatment of hypertensive disease. This has resulted in the introduction and trial of a number of drugs, including, amongst others, thiocyanates, nitroprussides, azides, hydrazinophthalazine (hydrallazine), veratrum, the ganglion blocking agents, ion exchange resins, barbiturates and the various extracts and alkaloids of Rauwolfia serpentina Benth. The introduction and use of Rauwolfia serpentina is of particular interest ; not only has it intriguing pharmacological properties, but it represents something of a return to the use of vegetable drugs, in an age which is becoming increasingly devoted to the use of synthetic chemicals in medicine. Although rauwolfia may ultimately not survive to take its place alongside the solanaceous drugs, the cardiac glycosides and opium, a study of its properties seems likely to lead to a clearer understanding of the complex mechanism underlying hypertensive disease in man. In this way it may establish itself firmly in the history of medicine. This may seem to be a jaundiced view to take of a new drug which is being widely used and widely studied. Many natural products have proved to be the starting points for further investigation and have yielded place to newer drugs with structures based upon the originals. A study of the literature indicates that this may be the fate of rauwolfia.
12 citations
01 Jan 1965
TL;DR: This chapter describes Rauwolfia alkaloids with special reference to the chemistry of reserpine, which has become important therapeutic agents, both as sedatives and antihypertensives.
Abstract: Publisher Summary This chapter describes Rauwolfia alkaloids with special reference to the chemistry of reserpine. Rauwolfia products have become important therapeutic agents, both as sedatives and antihypertensives. Although their production and use have fallen off since the peak years of 1955 and 1956, it is estimated that their total sales a t the consumers' level in 1961 still amounted to $100 million in the United States alone. Since 1952, the year reserpine was first isolated, several thousand articles have been published on the isolation, chemistry, pharmacology, and clinical aspects of reserpine and other Rauwolfia alkaloids, and today these investigations are still being pursued. Botanists estimate the number of identified Rauwolfia species to be about 50, of which R. serpentina, R. canescens, R. vomitoria, and R. ligustrina have been investigated in detail. Only the first three species are important from the standpoint of supplies of therapeutically useful alkaloids; the last species is not especially rich in reserpine, but has nevertheless been investigated in great detail. The Indian plant, R. serpentina, has lost much of its importance (except for local production), as its reserpine content (0.1%) is only about half that of R. vomitoria, which is at present the most important species. It grows so plentifully in Central Africa, especially in the Congo, that cultivation is not necessary. It is considerably taller than R. serpentina, and procedures have been developed by Congolese collectors by which the smaller side roots may be cut periodically without loss of the tree.
11 citations
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TL;DR: Durch alkalische Hydrolyse wird Reserpin in Reserpinsäure, 3,4,5-Trimethoxybenzoesäure und Methanol gespalten anderer Spaltstücken wieder resynthetisieren.
Abstract: Durch alkalische Hydrolyse wird Reserpin in Reserpinsaure, 3,4,5-Trimethoxybenzoesaure und Methanol gespalten. Das Esteralkaloid liess sich aus diesen Spaltstucken wieder resynthetisieren.
27 citations
TL;DR: In this paper, die Isolierung von zwei neuen Alkaloiden aus Rauwolfia serpentina Benth. beschrieben.
Abstract: Es wird die Isolierung von zwei neuen Alkaloiden aus Rauwolfia serpentina Benth. beschrieben. Die Bruttoformel C21H26O3N2 sowie physikalische und chemische Eigenschaften kennzeichnen sie als Isomere des Yohimbins, was durch die Bezeichnung Rauhimbin und Isorauhimbin zum Ausdruck gebracht wird.
25 citations
22 citations
TL;DR: I m Verlaufe unse re r schon sei t l~ngerer Zeit im Gange bef ind l ichen U n t e r s u c h u n g e l l fiber die Reil la lkaloide der Rauwol f i a Se rpen t ina h a b e n wir zwei lleue Stoffe aufgefulldell.
Abstract: I m Verlaufe unse re r schon sei t l~ngerer Zeit im Gange bef ind l ichen U n t e r s u c h u n g e l l fiber die Reil la lkaloide der Rauwol f i a Se rpen t ina h a b e n wir zwei lleue Stoffe aufgefulldell , die b i sher noch n i ch t besehr ieben wurden . Es h a n d e l t s ich u m zwei S u b s t a n z e n I und II , die in eiller g e m e i n s a m e n Frakt ion m i t d e m seda t iv w i rkenden Pr inz ip der Droge, d e m Reserp in , vorkommel l . Von e iner N a m e n g e b u l l g wollen wir absehen , bis ihre even tue l l e V e r w a n d t s c h a f t m i t schon bek a n n t e n Stoffen wei ter gekl/irt ist. Die p h y s i k o e h e m i s c h e n D a t e n s ind :
21 citations
TL;DR: Reserpinine, a minor alkaloid of Rauwolfia serpentina Benth, has been isolated, and its structural formula is proposed.
Abstract: Reserpinine, a minor alkaloid ofRauwolfia serpentina Benth. accompanying Reserpine, has been isolated, and its structural formula is proposed.
20 citations