Indole alkaloids from "hairy roots" of <i>Rauwolfia</i> <i>serpentina</i>

Falkenhagen, Heike; Stöckigt, Joachim; Кузовкина, И. Н.; Alterman, I. E.; Kolshorn, Heinz

doi:10.1139/v93-276

Cited by 33 publications

(21 citation statements)

References 6 publications

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“…Both alkaloids became important drugs on the general pharmaceutical market. During the last two decades, cell systems derived from R. serpentina plants have been exhaustively investigated for alkaloid formation [6], [7]. Based on these results, cell suspension cultures were selected and applied to deliver a whole series of novel enzymes allowing for the first time the elucidation in great detail of the ajmaline biosynthetic pathway starting with the progenitors tryptamine and secologanin [8], (Fig.…”

Section: Introductionmentioning

confidence: 99%

A Newly-Detected Reductase fromRauvolfiaCloses a Gap in the Biosynthesis of the Antiarrhythmic Alkaloid Ajmaline

2002

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A new enzyme, 1,2-dihydrovomilenine reductase (E.C. 1.3.1), has been detected in Rauvolfia cell suspension cultures. The enzyme specifically converts 2beta( R)-1,2-dihydrovomilenine through an NADPH-dependent reaction into 17-O-acetylnorajmaline, a close biosynthetic precursor of the antiarrhythmic alkaloid ajmaline from Rauvolfia. A five-step purification procedure using SOURCE 30Q chromatography, hydroxyapatite chromatography, 2',5'-ADP Sepharose 4B affinity chromatography and ion exchange chromatography on DEAE Sepharose and Mono Q delivered an approximately 200-fold enriched enzyme in a yield of approximately 6%. SDS-PAGE showed an M r for the enzyme of approximately 48 kDa. Optimum pH and optimum temperature of the reductase were at pH 6.0 and 37 degrees C. The enzyme shows a limited distribution in cell cultures expressing ajmaline biosynthesis, and is obviously highly specific for the ajmaline pathway.

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Section: Introductionmentioning

confidence: 99%

A Newly-Detected Reductase fromRauvolfiaCloses a Gap in the Biosynthesis of the Antiarrhythmic Alkaloid Ajmaline

2002

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“…The six known yohimbine derivatives ( 3 – 8 ) were identified as rauvomitorine D ( 3 ), [10] pseudo‐ β ‐yohimbine ( 4 ), [23] 18 β ‐hydroxy‐3‐epi‐ α ‐yohimbine ( 5 ), [24] β ‐yohimbine ( 6 ), [25] corynanthine ( 7 ), [12] and rauvomitorine I ( 8 ) [10] by comparing the observed and reported NMR data.…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic Yohimbine‐Type Alkaloids from the Leaves of Rauvolfia vomitoria

Zhan

Miao

Zhang

et al. 2020

Chemistry & Biodiversity

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Two new yohimbine-type monoterpene indole alkaloids, rauvines A and B, and six known derivatives were obtained from the leaves of R. vomitoria. The structures of rauvines A and B were determined by extensive spectroscopic analyses, 13 C-NMR, and ECD calculations. This is the first time to determine the absolute configurations of yohimbine-type N-oxides by quantum chemistry calculations (13 C-NMR and ECD calculations). All the isolates were tested for their cytotoxicity against five human cancer cell lines. Rauvine B showed moderate cytotoxicity on human MCF-7 breast, SWS80 colon, and A549 lung cancer cell lines with IC 50 values of 25.5, 22.6, and 26.0 μM, respectively.

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“…A third Rauvolfia system analyzed for alkaloid biosynthesis is represented by "hairy root" cultures. In 1993 three papers appeared describing the alkaloid pattern of such root systems [20][21][22]. A re-investigation of these roots resulted in the identification of 19 alkaloids including three novel compounds of the sarpagan alkaloid group [23].…”

Section: Novel Plant Systems Of Rauvolfiamentioning

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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Indole alkaloids from "hairy roots" of Rauwolfia serpentina

Cited by 33 publications

References 6 publications

A Newly-Detected Reductase fromRauvolfiaCloses a Gap in the Biosynthesis of the Antiarrhythmic Alkaloid Ajmaline

A Newly-Detected Reductase fromRauvolfiaCloses a Gap in the Biosynthesis of the Antiarrhythmic Alkaloid Ajmaline

Cytotoxic Yohimbine‐Type Alkaloids from the Leaves of Rauvolfia vomitoria

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

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