On the origins of triterpenoid skeletal diversity.

doi:10.1016/J.PHYTOCHEM.2003.11.014

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On the origins of triterpenoid skeletal diversity.

Journal Article•DOI•

On the origins of triterpenoid skeletal diversity.

Ran Xu¹, Gia C. Fazio¹, Seiichi P. T. Matsuda¹•Institutions (1)

Rice University¹

01 Feb 2004-Phytochemistry (Phytochemistry)-Vol. 65, Iss: 3, pp 261-291

TL;DR: The triterpenoids are a large group of natural products derived from C(30) precursors and each of these structures is classified and mechanisms for their formation are provided.

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About: This article is published in Phytochemistry.The article was published on 2004-02-01. It has received 500 citations till now. The article focuses on the topics: Triterpene.

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Monograph•DOI•

The Biomarker Guide

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Kenneth E. Peters¹, Clifford C. Walters², J. M. Moldowan³•Institutions (3)

United States Geological Survey¹, ExxonMobil², Stanford University³

16 Dec 2004

TL;DR: The second edition of The Biomarker Guide as mentioned in this paper provides a comprehensive account of the role that biomarker technology plays both in petroleum exploration and in understanding Earth history and processes.

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Abstract: The second edition of The Biomarker Guide is a fully updated and expanded version of this essential reference. Now in two volumes, it provides a comprehensive account of the role that biomarker technology plays both in petroleum exploration and in understanding Earth history and processes. Biomarkers and Isotopes in the Environment and Human History details the origins of biomarkers and introduces basic chemical principles relevant to their study. It discusses analytical techniques, and applications of biomarkers to environmental and archaeological problems. The Biomarker Guide is an invaluable resource for geologists, petroleum geochemists, biogeochemists, environmental scientists and archaeologists.

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2,163 citations

Journal Article•DOI•

Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants.

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Jörg Degenhardt¹, Tobias G. Köllner¹, Jonathan Gershenzon¹•Institutions (1)

Max Planck Society¹

01 Oct 2009-Phytochemistry

TL;DR: This review covers the monoterpene and sesquiterpene synthases presenting an up-to-date list of enzymes reported and evidence for their ability to form multiple products.

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857 citations

Cites background from "On the origins of triterpenoid skel..."

...Triterpene syn- thases and the formation of the triterpene carbon skeleton have been very authoritatively reviewed in several recent articles (Xu et al., 2004; Phillips et al., 2006)....
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Journal Article•DOI•

Saponins, classification and occurrence in the plant kingdom

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Jean-Paul Vincken¹, L. Heng¹, Aede de Groot¹, Harry Gruppen¹•Institutions (1)

Wageningen University and Research Centre¹

01 Feb 2007-Phytochemistry

TL;DR: The oleanane skeleton was the most common skeleton and is present in most orders of the plant kingdom, and the relationship between the type of skeleton and the plant origin was investigated.

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592 citations

Cites background from "On the origins of triterpenoid skel..."

...These advancements have stimulated the classification of natural products based on the biosynthesis of their carbon skeletons (Devon and Scott, 1972; Connolly and Hill, 1991; Xu et al., 2004)....
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Journal Article•DOI•

Molecular activities, biosynthesis and evolution of triterpenoid saponins.

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Jörg M. Augustin¹, Vera Kuzina¹, Sven Bode Andersen¹, Søren Bak¹•Institutions (1)

University of Copenhagen¹

01 Apr 2011-Phytochemistry

TL;DR: This review summarizes current knowledge of triterpenoid saponin biosynthesis in plants, molecular activities, evolutionary aspects and perspectives for further gene discovery.

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560 citations

Journal Article•DOI•

Triterpene Biosynthesis in Plants

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Ramesha B. Thimmappa¹, Katrin Geisler, Thomas Louveau, Paul E. O'Maille, Anne Osbourn² - Show less +1 more•Institutions (2)

Norwich Research Park¹, John Innes Centre²

29 Apr 2014-Annual Review of Plant Biology

TL;DR: Recent developments in the field of triterpene biosynthesis are reviewed, an overview of the genes and enzymes that have been identified to date are given, and strategies for discovering new triterpenes pathways are discussed.

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Abstract: The triterpenes are one of the most numerous and diverse groups of plant natural products. They are complex molecules that are, for the most part, beyond the reach of chemical synthesis. Simple triterpenes are components of surface waxes and specialized membranes and may potentially act as signaling molecules, whereas complex glycosylated triterpenes (saponins) provide protection against pathogens and pests. Simple and conjugated triterpenes have a wide range of applications in the food, health, and industrial biotechnology sectors. Here, we review recent developments in the field of triterpene biosynthesis, give an overview of the genes and enzymes that have been identified to date, and discuss strategies for discovering new triterpene biosynthetic pathways.

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506 citations

Cites background from "On the origins of triterpenoid skel..."

...Specifically, cyclization of 2,3-oxidosqualene to lanosterol proceeds through a series of carbocationic intermediates (C-2 → C-6 → C-10 → C-14 → C-20) to form the tetracyclic C-20 protosterol cationic intermediate (163)....
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...More than 100 different triterpene scaffolds are currently known in plants (163)....
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References

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Journal Article•DOI•

Plant terpenoid synthases: Molecular biology and phylogenetic analysis

[...]

JÃ¶rg Bohlmann¹, Gilbert Meyer-Gauen, Rodney Croteau•Institutions (1)

Max Planck Society¹

14 Apr 1998-Proceedings of the National Academy of Sciences of the United States of America

TL;DR: This review focuses on the monoterpene, sesquiterpenes, and diterpene synthases of plant origin that use the corresponding C10, C15, and C20 prenyl diphosphates as substrates to generate the enormous diversity of carbon skeletons characteristic of the terpenoid family of natural products.

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Abstract: This review focuses on the monoterpene, sesquiterpene, and diterpene synthases of plant origin that use the corresponding C10, C15, and C20 prenyl diphosphates as substrates to generate the enormous diversity of carbon skeletons characteristic of the terpenoid family of natural products. A description of the enzymology and mechanism of terpenoid cyclization is followed by a discussion of molecular cloning and heterologous expression of terpenoid synthases. Sequence relatedness and phylogenetic reconstruction, based on 33 members of the Tps gene family, are delineated, and comparison of important structural features of these enzymes is provided. The review concludes with an overview of the organization and regulation of terpenoid metabolism, and of the biotechnological applications of terpenoid synthase genes.

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1,011 citations

"On the origins of triterpenoid skel..." refers background in this paper

...SCs and OSCs catalyze reactions that are mechanistically similar but phylogenetically distinct from terpene synthases a–f, which convert the acyclic allylic diphosphates geranyl pyrophosphate, farnesyl pyrophosphate, and geranylgeranyl pyrophosphate to monoterpenes, sesquiterpenes, and diterpenes, respectively (Bohlmann et al., 1998; Trapp and Croteau, 2001)....
[...]
...…but phylogenetically distinct from terpene synthases a–f, which convert the acyclic allylic diphosphates geranyl pyrophosphate, farnesyl pyrophosphate, and geranylgeranyl pyrophosphate to monoterpenes, sesquiterpenes, and diterpenes, respectively (Bohlmann et al., 1998; Trapp and Croteau, 2001)....
[...]

Journal Article•DOI•

Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes

[...]

Ikuro Abe¹, Michel Rohmer², Glenn D. Prestwich¹•Institutions (2)

Stony Brook University¹, University of Upper Alsace²

01 Sep 1993-Chemical Reviews

592 citations

Journal Article•DOI•

The isoprene rule and the biogenesis of terpenic compounds.

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L. Ruzicka

15 Oct 1953-Cellular and Molecular Life Sciences

TL;DR: Die Zusammenhänge zwischen Diterpenen und Triterpenen in bezug auf ihre Konstitution and Konfiguration werden diskutiert, wobei auf die weitgehende Übereinstimmung ihrer Konfigurations mit der Konfigification der Steroide hingewiesen wird.

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Abstract: Es wird eine Ubersicht uber die Kohlenstoffgeruste der Sesquiterpene, Diterpene und Triterpene gegeben. Die Isoprenregel zeigt in jeder dieser Gruppen besondere Eigenheiten. Auch die C30-Steroide und ein Steroid mit 31 Kohlenstoffatomen, die mit den Triterpenen verwandt sind, werden besprochen. Die Zusammenhange zwischen Diterpenen und Triterpenen in bezug auf ihre Konstitution und Konfiguration werden diskutiert, wobei auf die weitgehende Ubereinstimmung ihrer Konfiguration mit der Konfiguration der Steroide hingewiesen wird. Die kurzlich durch die Experimentalarbeiten vonBloch gewonnenen Kenntnisse uber die biologische Entstehung des Cholesterins aus Essigsaure, unter sehr wahrscheinlicher Zwischenbildung des Triterpens Squalen, geben Anlass zur Erorterung hypothetischer Wege fur die Biogenese der pentazyklischen Triterpene aus Squalen, der zyklischen Sesquiterpene aus Farnesol, der zyklischen Diterpene aus Geranyl-geraniol und schliesslich auch der zyklischen Monoterpene aus Geraniol, unter Beachtung der elektronischen Zyklisierungsmechanismen der organischen Chemie. Schliesslich wird die «biogenetische» Isoprenregel definiert und ihre Bedeutung diskutiert.

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580 citations

"On the origins of triterpenoid skel..." refers background in this paper

...Ruzicka and co-workers proposed that this stereochemical information was maintained via well-defined bridged (nonclassical), short-lived, ionic intermediates (Ruzicka et al., 1953; Eschenmoser et al., 1955; Arigoni, 1959; Ruzicka, 1959, 1963)....
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...…triterpene alcohols known by that time were biosynthesized similarly, and they proposed the biogenetic isoprene rule, a set of governing principles that could explain the biosynthesis of each triterpene skeleton (Ruzicka et al., 1953; Eschenmoser et al., 1955; Arigoni, 1959; Ruzicka, 1959, 1963)....
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...In the early 1950s, Ruzicka and co-workers deduced that all C30H50O triterpene alcohols known by that time were biosynthesized similarly, and they proposed the biogenetic isoprene rule, a set of governing principles that could explain the biosynthesis of each triterpene skeleton (Ruzicka et al., 1953; Eschenmoser et al., 1955; Arigoni, 1959; Ruzicka, 1959, 1963)....
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Journal Article•DOI•

Zur Kenntnis der Triterpene. 190. Mitteilung. Eine stereochemische Interpretation der biogenetischen Isoprenregel bei den Triterpenen

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Albert Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni

01 Jan 1955-Helvetica Chimica Acta

TL;DR: In this article, the biogenetic isoprene rule in its application to the triterpenes is discussed from a stereochemical standpoint, and a scheme has been developed leading from squalene to the formulae of the basic representatives of all known cyclic triterpene groups in their full structural and configurational detail.

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Abstract: The biogenetic isoprene rule in its application to the triterpenes is discussed from a stereochemical standpoint. On the basis of a well defined system of arbitrary assumptions a scheme has been developed leading from squalene to the formulae of the basic representatives of all known cyclic triterpene groups - i.e. euphol, tirucallol, lupeol, taraxasterol, germanicol, β-amyrin, taraxerol, friedelin, α-amyrin, lanosterol - in their full structural and configurational detail. This result is considered to support the squalene hypothesis of the biogenesis of cyclic triterpenes.

...read moreread less

502 citations

"On the origins of triterpenoid skel..." refers background in this paper

...Ruzicka and co-workers proposed that this stereochemical information was maintained via well-defined bridged (nonclassical), short-lived, ionic intermediates (Ruzicka et al., 1953; Eschenmoser et al., 1955; Arigoni, 1959; Ruzicka, 1959, 1963)....
[...]
...…triterpene alcohols known by that time were biosynthesized similarly, and they proposed the biogenetic isoprene rule, a set of governing principles that could explain the biosynthesis of each triterpene skeleton (Ruzicka et al., 1953; Eschenmoser et al., 1955; Arigoni, 1959; Ruzicka, 1959, 1963)....
[...]

Journal Article•DOI•

Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications

[...]

S Trapp¹, Rodney Croteau¹•Institutions (1)

Washington State University¹

01 Jun 2001-Genetics

TL;DR: A model presented for the evolutionary history of plant terpenoid synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization.

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Abstract: Terpenoids are the largest, most diverse class of plant natural products and they play numerous functional roles in primary metabolism and in ecological interactions. The first committed step in the formation of the various terpenoid classes is the transformation of the prenyl diphosphate precursors, geranyl diphosphate, farnesyl diphosphate, and geranylgeranyl diphosphate, to the parent structures of each type catalyzed by the respective monoterpene (C(10)), sesquiterpene (C(15)), and diterpene synthases (C(20)). Over 30 cDNAs encoding plant terpenoid synthases involved in primary and secondary metabolism have been cloned and characterized. Here we describe the isolation and analysis of six genomic clones encoding terpene synthases of conifers, [(-)-pinene (C(10)), (-)-limonene (C(10)), (E)-alpha-bisabolene (C(15)), delta-selinene (C(15)), and abietadiene synthase (C(20)) from Abies grandis and taxadiene synthase (C(20)) from Taxus brevifolia], all of which are involved in natural products biosynthesis. Genome organization (intron number, size, placement and phase, and exon size) of these gymnosperm terpene synthases was compared to eight previously characterized angiosperm terpene synthase genes and to six putative terpene synthase genomic sequences from Arabidopsis thaliana. Three distinct classes of terpene synthase genes were discerned, from which assumed patterns of sequential intron loss and the loss of an unusual internal sequence element suggest that the ancestral terpenoid synthase gene resembled a contemporary conifer diterpene synthase gene in containing at least 12 introns and 13 exons of conserved size. A model presented for the evolutionary history of plant terpene synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization. This novel molecular evolutionary approach focused on genes of secondary metabolism may have broad implications for the origins of natural products and for plant phylogenetics in general.

...read moreread less

463 citations

"On the origins of triterpenoid skel..." refers background in this paper

...SCs and OSCs catalyze reactions that are mechanistically similar but phylogenetically distinct from terpene synthases a–f, which convert the acyclic allylic diphosphates geranyl pyrophosphate, farnesyl pyrophosphate, and geranylgeranyl pyrophosphate to monoterpenes, sesquiterpenes, and diterpenes, respectively (Bohlmann et al., 1998; Trapp and Croteau, 2001)....
[...]
...…but phylogenetically distinct from terpene synthases a–f, which convert the acyclic allylic diphosphates geranyl pyrophosphate, farnesyl pyrophosphate, and geranylgeranyl pyrophosphate to monoterpenes, sesquiterpenes, and diterpenes, respectively (Bohlmann et al., 1998; Trapp and Croteau, 2001)....
[...]