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: In this article, the Stellung der einen Methoxylgruppe festgelegt, wogegen die Haftstellen der drei weiteren funktionelle Gruppen noch nicht gesichert sind.
Abstract: Bei der Permanganatoxydation und der Kalischmelze der Reserpinsaure wurden 4-Methoxy-oxalylanthranilsaure und 5-Oxyisophtalsaure isoliert. Als Arbeitshypothese wird deshalb fur Reserpinsaure eine Yohimbanstruktur postuliert. Durch die obigen Abbauergebnisse ist die Stellung der einen Methoxylgruppe festgelegt, wogegen die Haftstellen der drei weiteren funktionellen Gruppen noch nicht gesichert sind.
20 citations
TL;DR: Die funktionellen Gruppen des Indolalkaloids Ajmalin (Rauwolfin) werden aufgeklärt and die Base wird mit Natronkalk and mit Zinkstaub destilliert, die Abbauresultate lassen vermuten.
Abstract: Die funktionellen Gruppen des Indolalkaloids Ajmalin (Rauwolfin) werden aufgeklart und die Base wird mit Natronkalk und mit Zinkstaub destilliert. Die Abbauresultate lassen vermuten, das es sich beim Ajmalin um einen Korper handelt, der Strukturelemente des Strychnins enthalt. Als weniger wahrscheinliche Alternative wird eine Struktur vorgeschlagen, die der Yohimbinformel nahesteht.
18 citations
TL;DR: Achlioptas et al. as discussed by the authors have shown that it is possible to identify the person who is the root of the root cause of the outbreak of the plague in the first place.
Abstract: yon 2 t0 -4 m lest. Die gleichen Ergebnisse h a b e n vor uns TIVOli, SON ~) m i t e inem unge re in ig t en Gehi rnchol ines te rase p r~pa ra t uud MASSART n n d DU~AIT n) m i t der Se rumchol in es te rase e rha l ten . Zur K l g r u n g dieser ~Widersprfiche wurde dahe r eine eingehende U n t e r s u c h u n g der A r s e n i t h e m m u n g unse r e r A C h E anges te l l t . W i t f a n d e n dabei , dab du rch Z usa t z von Arsen i t v611ig verg i f te te F e r m e n t a n s g t z e s ich bere i t s d u t c h 24stf indige Dia lvse gegen dest i l l ier tes W a s s e r volls tXndig reak t iv ie ren lieBen, was gegen eine feste M e r c a p t i d b i n d u n g spr ichL Bei V e r w e n d u n g einer o rgan i schen dre iwer t igen Arsenv e r b i n d u n g ( m a m i n o p h y d r o x y p h e n y l a r s e n o x y d , Maphar sen) sind, u m eine gleich grof3e H e m m u n g zu erreichen, wie sic d u t c h Arseni t erfolgt, u m zwei Z e h n e r p o t e n z e n h6here molare K o n z e n t r a t i o n e n erforderl ich, obwohl n a c h der LiteraturI2), ~) das Gegente i l zu e rwar ten w~Lre. V e r w a n d t e n wi t an Stelle yon N a t r i n m a r s e n i t die ana logen V e r b i n d u n g e n der Metal io ide Selen u n d Tel lur (Na t r iumseleni t u n d Na t r iumte l lu r i t ) , welche gleihhfalls Mercap t id b i ldner sindl~), so blieb die H e m m u n g der A C h S p a l t u n g se lbs t hei V e r w e n d u n g yon K o n z e n t r a t i o n e n in der Gr6Be t 10 2 m aus. Die H e m m u n g der A C h E du rch N a t r i u m a r s e n i t sche in t dahe r n i ch t au f d e m Wege der M ercap t i db i l dung mi t einer fiir die F e r m e n t a k t i v i t g t wich t igen S I t G r u p p e z u s t a n d e zu k o m m e n . Wie die Io lgenden Versuche zeigen, liegt der A n g r i f f s p u n k t des Arsen i t s o f fenbar a m , , ak t iven Z e n t r u m \" der ACHE. Bei gleicher Arsen i t u n d versch iedener S u b s t r a t k o n z e n t r a t ion wird die S p a l t u n g des ACh u m so m e h r gehemms je kleiner die zugese tz t en ACh-Mengen sind. E s hande l t sich d e m n a c h u m eiue k o m p e t i t i v e H e m m u n g , w o m i t wahr sche in lictl g e m a c h t wird, dab Arsen i t u n d ACh an der gleichen akr iven Gruppe des F e r m e n t e s angre i fen . E inen we i t e r en Beweis hierft ir l iefer ten Ver suche m i t e inem H e m m s t o f f au s der Re ihe der A l k y l p h o s p h a t e (p-Ni t rophenold i g t h y l p h o s p h a t , ,Mintacol\" , Bayer), die h e k a n n t l i c h eine P h o s p h o r y l i e r u n g des a k t i v e n Z e n t r u m s der Chol ines terase ve ru r sachen . Es gel ingt ngml ich , die A C h E d u t c h vorher ige ]3ehandluug m i t Arsen i t vo r der i r revers ib len H e m m u n g m i t p N i t r o p h e n o l d i ~ t h y l p h o s p h a t we i tgehend zu schfi tzen. Mit Arsen i t g e h e m m t e und d a n a c h m i t t . t 0 ~ p N i t r o p h e n o l di~Lthylphosphat behande l t e F e r m e n t l 6 s u n g e n k 6 n n e n nach d e m Herausd i a ly s i e r en der be iden Stoffe bis zu 85% ihrer an fgng l ichen A k t i v i t ~ t wieder erreichen, w~hrend Eermen~16sungen ohne vo rhe r igen Arsen i t zusa t z d u t c h p -Ni t ropheno l d i ~ t h y l p h o s p h a t vo l l s tgnd ig und i r revers ibel g e h e m m t werden. D u r c h nach t rgg t i che Dia lvse s ind sie n i ch t m e h r zu e n t h e m m e n .
18 citations
16 citations
TL;DR: In this paper, the Darstellung des Py-Tetrahydro-serpentins is discussed, and the Alkaloid Serpentin eine im Ring E modifizerte Konstitutionsformel aufgestellt.
Abstract: Es wurde fur das Alkaloid Serpentin eine im Ring E modifizerte Konstitutionsformel aufgestellt und die Darstellung des Py-Tetrahydro-serpentins beschrieben.
16 citations