Rauwolfia Alkaloids. XXXVIII.1 Stereospecific Degradations Leading to the Absolute Configurations and Structures of Ajmaline, Sarpagine and Corynantheidine2

Bartlett, M. F.; Sklar, R.; Taylor, W. I.; Schlittler, E.; Amai, Robert L. S.; Beak, Peter; Bringi, N. V.; Wenkert, Ernest

doi:10.1021/ja00863a024

Cited by 75 publications

(25 citation statements)

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“…Ofi$ena.uer-Oxydation von Seredamin (7) (Fluorenon/Kalium-t-butylat [5]) gab das Keton 9, das auf Grund des Vergleiches mit den publizierten spektralen Daten identisch rnit dem (+)-Purpelin [715) ist.…”

unclassified

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N_(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

Hanaoka

Hesse

Schmid

1970

Helvetica Chimica Acta

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unclassified

“…[lo]. Auch das (+)-2l-Desoxyajmalon (14) [ 5 ] , dessen absolute Konfiguration bekannt ist, zeigt bei 300 nm einen positiven Keton-Cotton-Effekt (u x = -1347 bzw. -1141).…”

unclassified

N_(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

Hanaoka

Hesse

Schmid

1970

Helvetica Chimica Acta

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“…In addition to the known alkaloids sandwicine (3) (Danieli et al, 1984;Gorman et al, 1957), isosandwicine (4) (Ahmad et al, 1988;Jokela and Lounasmaa, 1996;Russo et al, 1971), spegatrine (8) (Madinaveitia et al, 1995;Orazi et al, 1966), lochneram (9) (Arnold et al, 1958;Bartlett et al, 1962;Edwankar et al, 2013;Madinaveitia et al, 1995), and flavopereirine (13) (Bejar et al, 1957;Hughes and Rapoport, 1958;Janot et al, 1958;Reina et al, 2012;Steele et al, 2002), six compounds are described for the first time: norsandwicine (5), isonorsandwicine (6), N bmethylisosandwicine (7), 10-methoxypanarine (10), nortueiaoine (11) and tueiaoine (12) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Indole alkaloids from the Marquesan plant Rauvolfia nukuhivensis and their effects on ion channels

et al. 2015

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“…In addition, the alkaloid exhibits nine chiral carbon centers. It was the enormous effort of Woodward's group and also the elegant structure elucidation work done by his colleagues at Ciba Geigy which at the end resulted in the successful structure determination of ajmaline [9,10].…”

Section: Introduction -Some Historical Remarksmentioning

confidence: 99%

Alkaloid Biosynthesis in Rauvolfia- cDNA Cloning of Major Enzymes of the Ajmaline Pathway

Ruppert¹,

Ma²,

Stöckigt³

2005

COC

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All the major reactions taking part in the biosynthesis of ajmaline in cell suspension cultures of the Indian medicinal plant Rauvolfia have now been established at the enzyme level. Of the well investigated 10 steps six of the involved enzymes have been functionally cloned. These are strictosidine synthase (STR), strictosidine glucosidase (SG), polyneuridine aldehyde esterase (PNAE), vinorine synthase (VS), cytochrome P450 reductase (CPR) and acetylajmalan acetylesterase (AAE). Because the cDNAs of these enzymes are now known their detailed molecular analysis became attainable for the first time. Some of these enzymes such as STR, SG or VS could be produced in E. coli at a preparative scale resulting in mg amounts of pure enzymes. They also have been crystallized and their preliminary X-ray analyses were published recently. It is only a matter of time that their molecular structure and the mechanisms of the catalyzed reactions will be elucidated. Of the soluble enzymes vomilenine reductase and 1.2-dihydrovomilenine reductase remain to be heterologously expressed. Appropriate cDNA clones have recently been isolated. What membrane bound enzymes of this pathway is concerned cloning could not be achieved up to now. Our future strategy is to purify these enzymes first and to use the "reverse genetic" approach as we did for the soluble enzymes. The sarpagine bridge enzyme (SBE), vinorine hydroxylase (VH) and norajmaline N-methyltransferase (NAMT) are the only enzymes which remain as the major candidates for expression studies in order to express heterologously the complete ajmaline biosynthetic pathway.

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Rauwolfia Alkaloids. XXXVIII.¹ Stereospecific Degradations Leading to the Absolute Configurations and Structures of Ajmaline, Sarpagine and Corynantheidine²

Cited by 75 publications

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N_(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

N_(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

Indole alkaloids from the Marquesan plant Rauvolfia nukuhivensis and their effects on ion channels

Alkaloid Biosynthesis in Rauvolfia- cDNA Cloning of Major Enzymes of the Ajmaline Pathway

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Rauwolfia Alkaloids. XXXVIII.1 Stereospecific Degradations Leading to the Absolute Configurations and Structures of Ajmaline, Sarpagine and Corynantheidine2

Cited by 75 publications

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N(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

N(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

Indole alkaloids from the Marquesan plant Rauvolfia nukuhivensis and their effects on ion channels

Alkaloid Biosynthesis in Rauvolfia- cDNA Cloning of Major Enzymes of the Ajmaline Pathway

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Resources

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Rauwolfia Alkaloids. XXXVIII.¹ Stereospecific Degradations Leading to the Absolute Configurations and Structures of Ajmaline, Sarpagine and Corynantheidine²

N_(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide

N_(a)‐Demethylseredamin, ein neues Alkaloid aus Rauwolfia sumatrana; absolute Konfiguration von Seredamin. 140. Mitteilung über Alkaloide