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Book ChapterDOI

Chapter 13 Rauwolfia Alkaloids with Special Reference to the Chemistry of Reserpine

E. Schlittler
- Vol. 8, pp 287-334
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TLDR
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.

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Citations
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Journal ArticleDOI

A divergent approach to the synthesis of the yohimbinoid alkaloids venenatine and alstovenine

TL;DR: A functionalized hydrindanone enables a divergent strategy that builds on existing precedent to address this long-standing challenge of complete control in setting the C(3) stereocentre at a late stage of the yohimbinoid skeleton.
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Quantification and characterization of alkaloids from roots of Rauwolfia serpentina using ultra-high performance liquid chromatography-photo diode array-mass spectrometry

TL;DR: A new UHPLC-UV method has been developed for the simultaneous analysis of seven alkaloids from the root samples of Rauwolfia serpentina (L.) Benth and the results indicated that commercial products are of variable quality.
Book ChapterDOI

The Pharmacology of Rauwolfia Alkaloids

M. J. Rand, +1 more
TL;DR: Preparations derived from species of Rauwolfia, a plant genus belonging to the Apocynaceae family, have been used for the treatment of a great variety of diseases in the folk medicine of the regions in which they are found.
Journal ArticleDOI

Natural Products and Their Mimics as Targets of Opportunity for Discovery

TL;DR: In the recent excursion into applications of synthetic organic chemistry to neuroscience, avoiding the more-traveled paths was richly rewarding, and the unexpected often led to new revelations and insights.
References
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Journal ArticleDOI

Sarpagin, ein neues Alkaloid aus Rauwolfia serpentina Benth

A. Stoll, +1 more
TL;DR: In this article, die Isolierung eines neuen Alkaloids aus Rauwolfia serpentina Benth is discussed, i.e., a basischen basische alkaloid, which besitzt die Bruttoformel C19H22O2N2, HX.
Journal ArticleDOI

Untersuchungen über asymmetrische Synthesen II. Über den sterischen Verlauf der Umsetzung von Phenylglyoxylsäure-estern des Menthols, Neomenthols, Borneols und Isoborneols mit Methylmagnesiumjodid

V. Prelog, +1 more
TL;DR: In this article, die Phenylglyoxylsaure-ester des (−)-Menthols, (+)-Neomenthol, (−)-Borneols and (−)-Isoborneols wurden mit Methylmagnesiumjodid umgesetzt, und das optische Drehungsvermogen der nach der Verseifung des Reaktionsproduktes erhaltenen Atrolactinsaure wurde bestimmt.
Journal ArticleDOI

Vomilenin und seine Umwandlung in Perakin

TL;DR: Vomilenine (III), a minor alkaloid from Rauwolfia vomitoria of the indolenine type, could be structurally related to ajmaline.