Distant Precursors of Benzylisoquinoline Alkaloids and their Enzymatic Formation

  title={Distant Precursors of Benzylisoquinoline Alkaloids and their Enzymatic Formation},
  author={M. Rueffer and M. Zenk},
  journal={Zeitschrift f{\"u}r Naturforschung C},
  pages={319 - 332}
The incorporation rates of labelled tyrosine, DOPA. tyramine. and dopamine have been investigated during the in vivo formation of the protoberberine alkaloid, jatrorrhizine, in callus cultures of Berberis canadensis. While tyrosine was equally well incorporated into both the isoquinoline (54%) and benzyl (46%) portions of the alkaloid, DOPA was almost exclusively (91%) transformed into the isoquinoline moiety. However, tyramine (25%) and to a lesser extent, dopamine (15%) were incorporated into… Expand
Implication of tyramine in the biosynthesis of morphinan alkaloids in Papaver
Of the total radioactivity in the alkaloids 97% was found to be associated with the ethylamines, a distribution consistent with the NMR data, which can be explained by the compartmentalization of intermediates and enzymes of the pathway. Expand
Tyrosine Aminotransferase Contributes to Benzylisoquinoline Alkaloid Biosynthesis in Opium Poppy1[W]
The modest correlation between transcript levels and BIA accumulation in opium poppy supports a role for TyrAT in the generation of alkaloid precursors, but it also suggests the occurrence of other sources for 4-hydroxyphenylacetaldehyde. Expand
Molecular cloning and characterization of norcoclaurine synthase, an enzyme catalyzing the first committed step in benzylisoquinoline alkaloid biosynthesis.
The novel catalytic functions of NCS and HYP1 define a new class of plant secondary metabolic enzymes within the Bet v 1 and PR10 protein families. Expand
Tyrosinase involved in betalain biosynthesis of higher plants
It is proposed that this tyrosinase is specifically involved in the betalain biosynthesis of higher plants. Expand
Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy
Enzymes of this type catalyze regulatory, or rate-limiting, steps in metabolism, suggesting that NCS plays a role in controlling the rate of pathway flux in benzylisoquinoline alkaloid biosynthesis. Expand
Heterologous expression of alkaloid biosynthetic genes--a review.
The biosynthesis at the enzyme level of at-least two tetrahydrobenzylisoquinoline alkaloids, the benzophenanthridine alkaloid sanguinarine in the California poppy, Eschscholtzia californica, and the bisbenzymunine in barberry, Berberis stolonifera, has been elucidated in detail. Expand
Biosynthesis of bisbenzylisoquinoline alkaloids in cultured roots of Stephania cepharantha
The ratio of 13C‐enrichments of C‐4 and C‐α in (R) and (S) halves of aromoline was the same within experimental limits, which indicated that the two coclaurine units must have one and the same biogenetic origin. Expand
Biosynthetic Studies of Protoberberine and Related Alkaloids Using Plant Cell Cultures
The benzylisoquinolines comprise the largest group of alkaloids with about 2000 structures some of which possess valuable medicinal importance (such as codeine or morphine). During the past years theExpand
Analysis of promoters from tyrosine/dihydroxyphenylalanine decarboxylase and berberine bridge enzyme genes involved in benzylisoquinoline alkaloid biosynthesis in opium poppy
The data suggest that the wound signal caused by the entry of DNA-coated microcarriers into opium poppy cells was sufficient to induce tydc7 and bbe1 promoter activity, and that wound-responsive regulatory elements are located within domains identified by deletion analysis. Expand
Phloem-Specific Expression of Tyrosine/Dopa Decarboxylase Genes and the Biosynthesis of Isoquinoline Alkaloids in Opium Poppy.
The differential expression of TYDC genes and the organ-dependent accumulation of different alkaloids suggest a coordinated regulation of specific alkaloid biosynthetic genes that are ultimately controlled by specific developmental programs. Expand


in: Comprehensive Biochemistry 20
  • 231
  • 1968
Planta Medica 48
  • 212
  • 1983
  • 5
  • 1981
and D
  • B. M acLean, Can. J. Chem. 57, 1588
  • 1979
The Chemistry and Biology of Isoquinoline Alkaloids (Ed
  • J. D . Phillipson et a l.),
  • 1985
  • J. Peetsm a, Th. M. Malingre, and H. J. Huizing, Planta 162, 334
  • 1984
  • Biochem. Biophys. 222, 599
  • 1983
Phytochemistry 22
  • 1941
  • 1983
Naturwissenschaften 67
  • 620
  • 1981