Elucidation of iridodial formation mechanism - partial purification and characterization of the novel monoterpene cyclase from cell suspension cultures

Uesato, Shinichi; Ikeda, Hiromitsu; Fujita, Tetsuro; Inouye, Hiroyuki; Zenk, Meinhart H.

doi:10.1016/s0040-4039(00)96530-4

Cited by 32 publications

(12 citation statements)

References 4 publications

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“…The enzyme responsible for the cyclization has not yet been purified from C. roseus but was obtained from Rauwolfia serpentina (Uesato et al 1986(Uesato et al , 1987Verpoorte et al 1997).…”

Section: Cyclasementioning

confidence: 99%

Catharanthus terpenoid indole alkaloids: biosynthesis and regulation

2007

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Catharanthus roseus is still the only source for the powerful antitumour drugs vinblastine and vincristine. Some other pharmaceutical compounds from this plant, ajmalicine and serpentine are also of economical importance. Although C. roseus has been studied extensively and was subject of numerous publications, a full characterization of its alkaloid pathway is not yet achieved. Here we review some of the recent work done on this plant. Most of the work focussed on early steps of the pathway, particularly the discovery of the 2-C-methyl-D-erythritol 4-phosphate (MEP)-pathway leading to terpenoids. Both mevalonate and MEP pathways are utilized by plants with apparent cross-talk between them across different compartments. Many genes of the early steps in Catharanthus alkaloid pathway have been cloned and overexpressed to improve the biosynthesis. Research on the late steps in the pathway resulted in cloning of several genes. Enzymes and genes involved in indole alkaloid biosynthesis and various aspects of their localization and regulation are discussed. Much progress has been made at alkaloid regulatory level. Feeding precursors, growth regulators treatments and metabolic engineering are good tools to increase productivity of terpenoid indole alkaloids. But still our knowledge of the late steps in the Catharanthus alkaloid pathway and the genes involved is limited.

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“…The enzyme responsible for the cyclization has not yet been purified from C. roseus but was obtained from Rauwolfia serpentina (Uesato et al 1986(Uesato et al , 1987Verpoorte et al 1997).…”

Section: Cyclasementioning

confidence: 99%

Catharanthus terpenoid indole alkaloids: biosynthesis and regulation

2007

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“…3). It was isolated, semipurified and characterized from soluble extracts of C. roseus hairy roots (Sánchez-Iturbe et al 2005) and purified 440 fold from R. serpentina (Uesato et al 1986;Uesato et al 1987) and it seems to be a homotetramer with a molecular mass of 118 kDa and an optimal pH 7.0. The C. roseus enzyme has a molecular mass of 66 kDa.…”

Section: -Oxogeranial:iridodial Cyclasementioning

confidence: 99%

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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“…In this case, the cytochrome P450 enzyme VrtK was shown in vivo to catalyze the conversion of acyclic previridicatumtoxin (52) into 51 (Scheme 15). Based on isotope labeling studies with [ 13 C, 2 H]labeled mevalonates and quantum chemical modeling, Chooi et al proposed the formation of a tertiary carbocation intermediate (54) by a C15-C19 ring closure. However, since no C17-hydroxylated intermediate could be found in biotransformation assays, the dehydrogenation of 52 to a carbon radical, followed by electron transfer to the iron-heme center, thereby resulting in the formation of allylic cation 53, was suggested as an alternative.…”

Section: Meroterpene Cyclization Catalyzed By a Cytochrome P450 Enzymementioning

confidence: 99%

Terpenoid Biosynthesis Off the Beaten Track: Unconventional Cyclases and Their Impact on Biomimetic Synthesis

2014

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Terpene and terpenoid cyclizations are counted among the most complex chemical reactions occurring in nature and contribute crucially to the tremendous structural diversity of this largest family of natural products. Many studies were conducted at the chemical, genetic, and biochemical levels to gain mechanistic insights into these intriguing reactions that are catalyzed by terpene and terpenoid cyclases. A myriad of these enzymes have been characterized. Classical textbook knowledge divides terpene/terpenoid cyclases into two major classes according to their structure and reaction mechanism. However, recent discoveries of novel types of terpenoid cyclases illustrate that nature's enzymatic repertoire is far more diverse than initially thought. This Review outlines novel terpenoid cyclases that are out of the ordinary.

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Elucidation of iridodial formation mechanism - partial purification and characterization of the novel monoterpene cyclase from cell suspension cultures

Cited by 32 publications

References 4 publications

Catharanthus terpenoid indole alkaloids: biosynthesis and regulation

Catharanthus terpenoid indole alkaloids: biosynthesis and regulation

Catharanthus biosynthetic enzymes: the road ahead

Terpenoid Biosynthesis Off the Beaten Track: Unconventional Cyclases and Their Impact on Biomimetic Synthesis

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