3-hydroxy-16-methoxy-2,3-dihydrotabersonine

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine

3-Hydroxy-16-methoxy-2,3-dihydrotabersonine

Chemical compound


3-Hydroxy-16-methoxy-2,3-dihydrotabersonine is a terpene indole alkaloid produced by Catharanthus roseus. The metabolite is a substrate for 3-hydroxy-16-methoxy-2,3-dihydrotabersonine N-methyltransferase (NMT) which transfers a methyl group to the nitrogen of the indole ring forming desacetoxyvindoline.[1] The enzyme catalyzing the formation of 3-hydroxy-16-methoxy-2,3-dihydrotabersonine from 16-methoxytabersonine is currently unknown, but is a result of hydration of the double bond connecting the 6 and 13 position carbons.[2] [3]

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References

  1. Dethier and De Luca (1993) Partial purification of an N-methyltransferase involved in vindoline biosynthesis in Catharanthus roseus. Phytochemistry. 32(3). 673-678
  2. Liscombe, Usera and O’connor (2010) Homolog of tocopherol C methyltransferases catalyzes N methylation in anticancer alkaloid biosynthesis. Proceedings of the National Academy of Sciences. 107(44). 18793-18798
  3. O'connor and Maresh (2006) Chemistry and biology of monoterpene indole alkaloid biosynthesis. Natural Product Reports. 23(4). 532-547

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