Rauwolfia serpentina Benth

Rauwolfia serpentina Benth, which derives its name from Leonhart Rauwolf, a 16th century botanist, and its serpentine root (Figure 56.1), has long been used in India for a variety of ailments. The discovery of its tranquilizing action, particularly in lowering the blood pressure, led to its introduction into Western medicine. The Rauwolfia alkaloids are derived from a family of tropical and semitropical plants related to oleander and periwinkle. They vary from small shrubs to tall trees. The important species from which the alkaloids are derived include Rauwolfia serpentina (Ophioxylon serpentinum or Indian snakeroot), R. micrantha, R. vomitoria, and R. hirsuta (Canescens heterophylla). 

Rauwolfia serpentina (Benth. ex Kurz Apocynaceae Ajmalicidine (72)... 

The natural representative of this group is 8-yohimbine or ajmalicine first, found in Yohimbe and in Rauwolfia serpentina Benth. ex Kurz (Volume VII). 

Schiibel, H., Stockigt, J., Feicht, R. and Simon, H. (1986) Partial purification and characterisation of raucaffricine fJ-D-glucosidase from plant cell suspension cultures of Rauwolfia serpentina Benth. Helv. Chim. Acta, 69, 538-47. 

Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodward s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, has been used to manage mild hypertension associated with anxiety. 

No studies were found on the hypnotic activity of the phenolic acids however, the hypnotic activity of alkaloids is known. Dl-Tetrahydropalmatine (dl-THP), a naturally occurring alkaloid, has been intensively studied for its sedative and hypnotic effects. A putative explanation for its mechanism and target of action involves the dopaminergic neurotransmission system [371]. Reserpine, an alkaloid from Rauwolfia serpentina Benth. ex Kurz, was widely used for its antihypertensive action. Flowever, its use has been reduced because of its... 

The deep-yellow base serpentinine, first isolated from Rauwolfia serpentina Benth. ex Kurz and later from other related species, possesses the molecular formula C42H44O6N4, based on elemental analyses and molecular weight determinations. The anhydrous compound is hygroscopic and crystallises with 1—2 moles of water. The analyses of a number of salts agree with this formula. 

Rauwolfia serpentina Benth. is the source of several related alkaloids. Ajmaline, ajmalicine, ajmalinine, serpentine, serpentinine, isoajmaline, and neoajmaline have been identified. Ajmaline and serpentine have been given provisional structural formulas (81, 82). Other members of the Apocynaceae yield alkaloids of similar properties. Although Rauwolfia preparations have been used in Ayurvedic medicine for hypertension, there appear no indications that they have been used in clinical cardiac arrhythmia. Yet, incomplete pharmacologic studies indicate properties for these alkaloids which should prompt additional studies toward their possible use in auricular fibrillation. 

Muller, J.M., Schlittler, E. and Bein, H.L (1952) Reserpin, der sedative Wirkstoff aus Rauwolfia serpentina Benth. Experientia (Basel) 8 338. 

H. SchUbel and J. Stfickigt, RLCC-isolation of Raucaffricine from its most efficient source-cell suspension cultures of Rauwolfia serpentina Benth, Plant Cell. Rep., 3 (1984) 72-74. 

Hofmann A 1954 Die Isolierung weiterer Alkaloide aus Rauwolfia serpentina Benth. 3. Mitteilung iiber Rauwolfia Alkaloide. Helv Chim Acta 37 849-865... 

Resetpine was isolated in 1952 from the Indian snake-root, Rauwolfia serpentina Benth. The structure was determined by 1955 and the compound quickly became important for the treatment of nervous and mental disorders. The first total synthesis of reserpine was reported a year later and the compound has remained a popular target for synthesis throughout the past half century. We will examine six syntheses that span this time period. We will begin with the Woodward group synthesis Woodward, R B. Bader, F. E. Biokel, H. Frey, A. J. Kierstead, R. W. The Total Synthesis of Reserpine" J. Am. Chem. Soc. 1956, 78, 2023-2025. Woodward, R. B. Bader, F. E. Biokel, H. Frey, A. J. Kierstead, R W. "A Simplified Route to a Key Intermediate in the Total Synthesis of Reserpine" J. Am. Chem. Soc. 1956, 78, 2657. Woodward, R. B. Bader, F. E. Bickel, H. Frey, A. J. Kierstead, R. W. "The Total Synthesis of Reserpine" Tetrahedron 1958, 2, 1-57. 

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