Conversion of Vindoline into 11-Mesyloxytabersonine.
نویسندگان
چکیده
Conversion of readily available vindoline to 11-mesyloxytabersonine, a versatile synthetic intermediate for indole alkaloids, has been achieved by a 9-step sequence in 39% overall yield.
منابع مشابه
The Suzuki-Miyaura reaction in the chemical transformations of vindoline.
Vindoline and its analogues are important constituents of the Madagascan periwinkle Catharanthus roseus, and some of them are valuable chemotherapy drugs used in treatment for some types of cancer, including leukaemia, lymphoma, breast and lung cancer. The search for semi-synthetic congeners of natural substances is still an important task for organic chemistry. In this communication we report ...
متن کاملA Cytochrome P-450 Monooxygenase Catalyzes the First Step in the Conversion of Tabersonine to Vindoline in Catharanthus roseus.
Hydroxylation at the C-16 position of the indole alkaloid tabersonine has been suggested as the first step toward vindoline biosynthesis in Catharanthus roseus. Tabersonine 16-hydroxylase (16-OH) activity was detected in total protein extracts from young leaves of C. roseus using a novel coupled assay system. Enzyme activity was dependent on NADPH and molecular oxygen and was inhibited by CO, c...
متن کاملCompletion of the seven-step pathway from tabersonine to the anticancer drug precursor vindoline and its assembly in yeast.
Antitumor substances related to vinblastine and vincristine are exclusively found in the Catharanthus roseus (Madagascar periwinkle), a member of the Apocynaceae plant family, and continue to be extensively used in cancer chemotherapy. Although in high demand, these valuable compounds only accumulate in trace amounts in C. roseus leaves. Vinblastine and vincristine are condensed from the monote...
متن کاملA pair of tabersonine 16-hydroxylases initiates the synthesis of vindoline in an organ-dependent manner in Catharanthus roseus.
Hydroxylation of tabersonine at the C-16 position, catalyzed by tabersonine 16-hydroxylase (T16H), initiates the synthesis of vindoline that constitutes the main alkaloid accumulated in leaves of Catharanthus roseus. Over the last decade, this reaction has been associated with CYP71D12 cloned from undifferentiated C. roseus cells. In this study, we isolated a second cytochrome P450 (CYP71D351) ...
متن کاملEnhancement of vindoline production in suspension culture of the Catharanthus roseus cell line C20hi by light and methyl jasmonate elicitation.
The effects of light and methyl jasmonate (MJ) on the transcription of biosynthetic genes as well as the accumulation of vindoline and catharanthine in Catharanthus roseus C20hi cell suspensions were studied. t16h (the gene encoding tabersonine 16-hydroxylase) could be induced by light and MJ, whereas d4h (the gene encoding deacetoxyvindoline 4-hydroxylase) could only be induced by light. Quant...
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ورودعنوان ژورنال:
- Chemical & pharmaceutical bulletin
دوره 64 7 شماره
صفحات -
تاریخ انتشار 2016