Syntheses of marine molecules

Martı́n, Julio D.; Palazón, José M.; Pérez, Caridad N.; Ravelo, José L.

doi:10.1351/pac198658030395

Cited by 22 publications

(13 citation statements)

References 12 publications

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“…Moreover, although a-barbatene, thujopsene, and b-chamigrene have been isolated from a variety of diverse natural sources including marine organisms (Blunt et al, 2004), liverworts (von Reuss et al, 2004), and flowering plants (Aharoni et al, 2003;Chen et al, 2003) and have represented important challenges to the field of organic synthesis (Martin et al, 1986), the enzymatic mechanism(s) responsible for their biosynthesis have remained elusive (Scheme II). Extensive studies by Cane et al (Cane, 1990;Cane et al, 1997;Rynkiewicz et al, 2002) on the biosynthesis of trichodiene, the enantiomer of bazzanene, have provided an analogous model for the biosynthesis of this class of sesquiterpenes, which has been tested by feeding specificlabeled precursors to liverwort cell cultures (Nabeta et al, 1998;Warmers and Kö nig, 2000).…”

Section: Use Of the Surrogate Splicing Methods To Isolate Novel Terpenmentioning

confidence: 99%

Surrogate Splicing for Functional Analysis of Sesquiterpene Synthase Genes

Schoenbeck

Greenhagen

et al. 2005

Plant Physiology

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A method for the recovery of full-length cDNAs from predicted terpene synthase genes containing introns is described. The approach utilizes Agrobacterium-mediated transient expression coupled with a reverse transcription-polydeoxyribonucleotide chain reaction assay to facilitate expression cloning of processed transcripts. Subsequent expression of intronless cDNAs in a suitable prokaryotic host provides for direct functional testing of the encoded gene product. The method was optimized by examining the expression of an intron-containing b-glucuronidase gene agroinfiltrated into petunia (Petunia hybrida) leaves, and its utility was demonstrated by defining the function of two previously uncharacterized terpene synthases. A tobacco (Nicotiana tabacum) terpene synthase-like gene containing six predicted introns was characterized as having 5-epi-aristolochene synthase activity, while an Arabidopsis (Arabidopsis thaliana) gene previously annotated as a terpene synthase was shown to possess a novel sesquiterpene synthase activity for a-barbatene, thujopsene, and b-chamigrene biosynthesis.Terpene synthases are a class of enzymes that catalyze the conversion of prenyl diphosphates to mono-, sesqui-, and diterpenoid compounds (Chappell, 1995;Davis and Croteau, 2000). The reactions catalyzed by many of these enzymes are stereospecific and complex, often generating one to upwards of 30 reaction products (Steele et al., 1998), many of which may contain one or more ring structures. Terpene synthases are of particular interest to phytochemists for their role in the synthesis of natural products, including flavors and fragrances, such as nootkatone and patchouli alcohol and antimicrobial phytoalexins like capsidiol (Chappell, 1995). Sesquiterpene synthases, a subset of terpene synthases catalyzing the biosynthesis of products derived from farnesyl diphosphate, have been characterized from many plant species including tobacco (Nicotiana tabacum;Facchini and Chappell, 1992) Many of the initial molecular studies of sesquiterpene synthases were based on the identification of cDNA clones encoding for enzymes catalyzing the biosynthesis of particular sesquiterpene compounds (Facchini and Chappell, 1992). More recently, many of the plant genetic databases contain genomic sequences bearing significant similarity to known terpene synthases. However, the actual biochemical function for many of these genes is unknown. For example, the Arabidopsis genome contains between 34 and 40 genes annotated as having similarity to terpene synthases (Aubourg et al., 2002; Supplemental Figs. 1 and 2), though less than one-third of these have been confirmed through direct demonstration of catalytic function (Bohlmann et al., 2000;Chen et al., 2003Chen et al., , 2004 Fäldt et al., 2003). Furthermore, genome sequencing projects, by virtue of their comprehensive nature, are bound to reveal genes that may not be expressed because of any number of molecular alterations, yet are nonetheless of interest for mechanistic and evolutionary studies of catalytic ...

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Section: Use Of the Surrogate Splicing Methods To Isolate Novel Terpenmentioning

confidence: 99%

Surrogate Splicing for Functional Analysis of Sesquiterpene Synthase Genes

Schoenbeck

Greenhagen

et al. 2005

Plant Physiology

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“…The molecular mechanism of the anticancer activity of I3A (5) is unclear, and it has been suggested to be twofold, involving a combination of necrotic and immunostimulating effects [171]. Depending on the concentration and cell type, I3A shows necrotic or apoptotic properties, the latter seemingly dependent upon the activation of PKCδ and its translocation from the cytoplasm into the nuclear membrane.…”

Section: Molecular and Clinical Pharmacology Of Picato ®mentioning

confidence: 99%

Progress in the Chemistry of Organic Natural Products 102

Kinghorn¹,

Falk²,

Gibbons³

et al. 2016

Progress in the Chemistry of Organic Natural Products

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“…[16] The discovery of haloperoxidases in many marine organisms provided for the first time potential catalysts, and indeed vanadium-dependent bromoperoxidases (V-BrPOs) from marine algae turned out to catalyze the bromonium ion initiated cyclization of terpenes and ethers in vitro. [16] The discovery of haloperoxidases in many marine organisms provided for the first time potential catalysts, and indeed vanadium-dependent bromoperoxidases (V-BrPOs) from marine algae turned out to catalyze the bromonium ion initiated cyclization of terpenes and ethers in vitro.…”

Section: Novel Terpene Cyclases Frommentioning

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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Syntheses of marine molecules

Cited by 22 publications

References 12 publications

Surrogate Splicing for Functional Analysis of Sesquiterpene Synthase Genes

Surrogate Splicing for Functional Analysis of Sesquiterpene Synthase Genes

Progress in the Chemistry of Organic Natural Products 102

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

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