The IBOGA alkaloids and their role as precursors of anti-neoplastic bisindole catharanthus alkaloids

Sundberg, Richard J.; Smith, Stanton Q.

doi:10.1016/s0099-9598(02)59009-x

Cited by 25 publications

(15 citation statements)

References 295 publications

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“…The numbers inside the circle indicate the enzymes: tryptophan decarboxylase (1); strictosidine synthase (2); strictosidine glucosidase (3); geissoschizine dehydrogenase (4). The slash arrows show different metabolic steps (De Luca 1993;Meijer et al 1993c;Verpoorte et al 1997;Sundberg and Smith 2002) Phytochem Rev (2007) 6:307-339 317 was similar to that detected in suspension cultures, whereas the production of alkaloids recovered to 90% with respect to the initial production. These data suggest that the cells do not require elevated amounts of TDC activity to produce the TIAs.…”

Section: Biosynthesis Of the Tiasmentioning

confidence: 67%

“…The slash arrows show different metabolic steps. There is the possibility that the pathway does not start with 4,21-dehydrogeissoschizine, but with the 20,21-aldehyde of dehydrocorinanteine (Verpoorte et al 1997;Roberts 1998;Sundberg and Smith 2002) the plant cells to maintain ajmalicine stored inside the vacuole. In cellular suspensions of C. roseus the oxidation of ajmalicine seems to be regulated by light because in its presence the cultures produce a great amount of serpentine, but when cultivated in the dark they only accumulate ajmalicine (Blom et al 1991;Loyola-Vargas et al 1992).…”

Section: Biosynthesis Of the First Tiasmentioning

confidence: 99%

“…The dotted arrows indicate unknown enzymes and metabolic steps. Several arrows in the same step indicate the probability of various metabolic steps (Sundberg and Smith 2002) nine:NADP + oxidoreductase (EC 1.5.1.32) (reaction 6, Fig. 6).…”

Section: Biosynthesis Of the First Tiasmentioning

confidence: 99%

“…7) (Sundberg and Smith 2002). Nothing is known about the nature of the enzymes involved in the conversion of cathenamine to catharanthine and tabersonine.…”

Section: Biosynthesis Of Catharanthine and Tabersoninementioning

confidence: 99%

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Catharanthus biosynthetic enzymes: the road ahead

2007

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Alkaloids are one of the most diverse groups of secondary metabolites found in living organisms. The most economically important alkaloids are the bisindole vinblastine, and vincristine. Unraveling the complexity of the genetic, catalytic and transport processes of monoterpene indole alkaloids biosynthesis is one of the most stimulating intellectual challenges in the plant secondary metabolism field. More than 50 metabolic steps are required to synthesize the most important alkaloids in Catharanthus roseus. Until now about only 20 of the 50 enzymes required for their biosynthesis have been determined and characterized. Hence, there are still a number of important enzymes that need to be characterized, beginning with the isolation and cloning of genes. It is also of fundamental importance to elucidate the regulatory aspects of their biosynthesis, both at the cellular and the molecular level, in order to address the question of their function in the plants that are producing them. In this review, we present an analysis of the state of the art related to the biosynthesis of the monoterpene indole alkaloids.

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Section: Biosynthesis Of the Tiasmentioning

confidence: 67%

Section: Biosynthesis Of the First Tiasmentioning

confidence: 99%

Section: Biosynthesis Of the First Tiasmentioning

confidence: 99%

“…7) (Sundberg and Smith 2002). Nothing is known about the nature of the enzymes involved in the conversion of cathenamine to catharanthine and tabersonine.…”

Section: Biosynthesis Of Catharanthine and Tabersoninementioning

confidence: 99%

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Catharanthus biosynthetic enzymes: the road ahead

2007

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“…This ring has serve as an important precursor for natural product synthesis and has immense synthetic applications. The 2-azabicyclo-[2,2,2]-octane skeleton is found in a variety of natural products, particularly the Iboga family of alkaloids [13,14]. The imine derived in situ acts as a dienophile in this reaction.…”

Section: Introductionmentioning

confidence: 99%