Assignments of1H and13C NMR resonances of some isoquinoline alkaloids

Janssen, R. H. A. M.; Wijkens, Peter; Kruk, C.; Biessels, H. W. A.; Menichini, Francesco; Theuns, Hubert G.

doi:10.1016/0031-9422(90)80210-8

Cited by 30 publications

(9 citation statements)

References 32 publications

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“…All the signals of 1 appear to be broad peaks in DMSO-d6, possibly due to chemical exchange. The chemical shifts and integration of peaks agree with previous reported NMR data of 1 (refs 72 , 73 ). HRMS ( m / z ): [M+H] + calcd.…”

Section: Methodssupporting

confidence: 91%

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

2016

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Noscapine is a potential anticancer drug isolated from the opium poppy Papaver somniferum, and genes encoding enzymes responsible for the synthesis of noscapine have been recently discovered to be clustered on the genome of P. somniferum. Here, we reconstitute the noscapine gene cluster in Saccharomyces cerevisiae to achieve the microbial production of noscapine and related pathway intermediates, complementing and extending previous in planta and in vitro investigations. Our work provides structural validation of the secoberberine intermediates and the description of the narcotoline-4′-O-methyltransferase, suggesting this activity is catalysed by a unique heterodimer. We also reconstitute a 14-step biosynthetic pathway of noscapine from the simple alkaloid norlaudanosoline by engineering a yeast strain expressing 16 heterologous plant enzymes, achieving reconstitution of a complex plant pathway in a microbial host. Other engineered yeasts produce previously inaccessible pathway intermediates and a novel derivative, thereby advancing protoberberine and noscapine related drug discovery.

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Section: Methodssupporting

confidence: 91%

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

2016

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“…The present study has led to the isolation of a new bisbenzylisoquinoline, lancifoliaine ( 1 ), together with N -allyllaurolitsine ( 2 ) [ 6 ], reticuline ( 3 ) [ 7 , 8 , 9 ], actinodaphnine [ 10 ], norboldine [ 11 , 12 , 13 ], pallidine [ 14 , 15 , 16 ], cassythicine [ 17 ] and boldine [ 18 , 19 , 20 ] ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Lancifoliaine, a New Bisbenzylisoquinoline from the Bark of Litsea lancifolia

et al. 2011

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A new bisbenzylisoquinoline, lancifoliaine (1), together with seven known alkaloids – N-allyllaurolitsine (2), reticuline (3), actinodaphnine, norboldine, pallidine, cassythicine and boldine – were isolated from the stem bark of Litsea lancifolia (Lauraceae). In addition to that of lancifoliaine, complete 13C-NMR data of N-allyl-laurolitsine (2) was also reported. The alkaloidal structures were elucidated by means of high field 1D- and 2D-NMR IR, UV, and LCMS-IT-TOF spectral data. N-Allyllaurolitsine (2) showed a moderate vasorelaxant activity on isolated rat aorta.

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“…In our continuing research work on drugs that could complement the CQ action, we further investigated the stem bark of an about seven-yearold tree of H. voyronii since old trees become very rare as a result of their intensive use for manufacturing water-resistant coffins, dugouts, and wooden buildings. In this paper, we report the structure elucidation of a new pavine-BTlQdimer, herveline D (4), the 13C-NMR data of laetanine (3), (5), lindcarpine (4) (6), norpredicentrine (5) (7), norisocorydine (6) (8), and ocobotrine (7) (9), isolated together with N-methyllaurotetanine (8) (10), and (-)-pallidine (9) (11) as well as the biological activity of the A-D hervelines series, (S)-reticulirie (10) (12), and laudanosine (11) (13) in terms of antiplasmodial effect and CQenhancing action.…”

Section: Introductionmentioning

confidence: 99%

“…By counter-current distribution of the basic extract of the stem bark of an about seven-year-old tree of Hernandia voyronii, a new pavine-BTIQ dimer, herveline D (4) was isolated together with herveline A (1), five aporphine alkabids, laetanine (5), lindcarpine(6), norpredicentrine (7), norisocoridine (8), and N-methyllaurotetanine(10), two marphinane alkaloids, ocobotrine (9), and (-)-pallidine (11), and the BTIQ (S)-reticuline(12). Compounds 1, 7, and 9 were previously isolated from H. voyronii(2).…”

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confidence: 99%

Alkaloids ofHernandia voyronii: Chloroquine-Potentiating Activity and Structure Elucidation of Herveline D

et al. 1998

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Further investigation of Hernandia voyronii led to the isolation of a new pavine-benzyltetrahydroisoquinoline (pavine-BTIQ) dimer, herveline D, together with herveline A, five aporphine alkaloids, two morphinane alkaloids, and their bio-synthetic precursor, i.e., the BTIQ ( S)-reticuline. Hervelines A-D have a moderate intrinsic in vitro antimalarial activity (IC (50) in the range of 1.68-3.28 microM), but displayed different effects ranging from synergism for herveline B and herveline C to simple additive effect for herveline A, and antagonism for herveline D in a chloroquine (CQ) combination evaluation and this was confirmed in vivo for hervelines A and B. Furthermore, the antiplasmoidal activity of CQ was potentiated in vitro by reticuline and its dimethyl derivative laudanosine (for the latter also in vivo), whereas herveline C moderately potentiated in vitro the anti-plasmodial activity of herveline D.

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Assignments of1H and13C NMR resonances of some isoquinoline alkaloids

Cited by 30 publications

References 32 publications

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

Engineering biosynthesis of the anticancer alkaloid noscapine in yeast

Lancifoliaine, a New Bisbenzylisoquinoline from the Bark of Litsea lancifolia

Alkaloids ofHernandia voyronii: Chloroquine-Potentiating Activity and Structure Elucidation of Herveline D

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