From Terpenes to Sterols: Macroevolution and Microevolution

Ourisson, Guy; Rohmer, Michel; Anton, Robert Michael

doi:10.1007/978-1-4757-0097-8_5

Cited by 10 publications

(10 citation statements)

References 23 publications

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“…Bauerenol (77), germanicol (78), and phyllanthol (79) are pentacyclic triterpenes found in many plants from the genus Euphorbia (Rizk & El-Missiry, 1986). In general, herbaceous species accumulate cycloartenol, cactuslike species accumulate euphol and euphorbol, whereas "coral-like species" accumulate euphol and tirucallol (Ponsinet et al, 1968;Ourisson et al, 1979;Ramaiah et al, 1979;Rizk & El-Missiry, 1986). Members of the American subgenus Poinsettia usually contain fatty acid esters of pentacyclic triterpenes (Hegnauer, 1989;Ourisson et al, 1979).…”

Section: Many Plants Of the Euphorbiaceae Possess Latex That Ij Rich mentioning

confidence: 97%

“…The major triterpenes present are compounds related to cycloartenol, tetracyclic triterpenes, and pentacyclic triterpenes (Hegnauer, 1989;Ourisson et al, 1979). Bauerenol (77), germanicol (78), and phyllanthol (79) are pentacyclic triterpenes found in many plants from the genus Euphorbia (Rizk & El-Missiry, 1986).…”

Section: Many Plants Of the Euphorbiaceae Possess Latex That Ij Rich mentioning

confidence: 99%

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Phytochemistry and Systematics of the Euphorbiaceae

Seigler¹

1994

Annals of the Missouri Botanical Garden

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JSTOR is a not-for-profit service that helps scholars, researchers, and students discover, use, and build upon a wide range of content in a trusted digital archive. We use information technology and tools to increase productivity and facilitate new forms of scholarship. For more information about JSTOR, please contact support@jstor.org.. Missouri Botanical Garden Press is collaborating with JSTOR to digitize, preserve and extend access to Annals of the Missouri Botanical Garden. ABSTRACTPhytochemical data provide much useful information concerning relationships both within the Euphorbiaceae and between that family and putative relatives. Within the Euphorbiaceae, the presence of several groups of secondary metabolites support certain infrafamilial groupings, whereas data related to the biosynthesis and distribution of other secondary metabolites provide information concerning the relationship of the Euphorbiaceae to other families. Similarities in chemistry to both the Geraniales and Malvales are found, supporting the suggestion by Webster (1987) that the differences between the Dilliniidae and Rosidae may not be as great as previously thought, and that the Euphorbiaceae may have arisen from ancestors intermediate to those two groups.The chemistry of the Euphorbiaceae is among the most diverse and interesting of flowering plant families (Evans, 1986a, b; Hegnauer, 1966b Hegnauer, , 1989 and is comparable to the biological diversity of the family (Radcliffe-Smith, 1986; Webster, 1987). Because of the presence of unusual secondary metabolites, many species of euphorbiaceous plants are poisonous and have been involved in humanand livestock poisoning. Plants of this family, especially those of the genus Euphorbia, are known for their ability to induce dermatitis (Evans & Schmidt, 1980). Others have been used in folk medicine, as piscicides, or as arrow poisons. Several euphorbs are important food plants, and a number are important economically as ornamental plants and as sources of rubber, chemical precursors, lubricants, and medicinal compounds (RadcliffeSmith, 1986; Rizk, 1987).The principal goal of this article is to evaluate systematic and evolutionary relationships in the Euphorbiaceae with information derived from extant phytochemical literature. These data point to certain affinities of the Euphorbiaceae and suggest alignments of subfamilial taxa of this enigmatic family as well.What types of secondary compound data are likely to be useful? Both the presence and absence of secondary metabolites and the biosynthetic pathways responsible for their production are useful for establishing taxonomic and phylogenetic relationships. The products of relatively short pathways beginning with readily available precursors are more likely to have originated several times and usually are widespread among higher plants. Examples are glycosides of the flavones apigenin and luteolin and the flavonols kaempferol and quercetin (Seigler, 1977(Seigler, , 1981b. In general, compounds that are formed via complicated pathways with ma...

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Section: Many Plants Of the Euphorbiaceae Possess Latex That Ij Rich mentioning

confidence: 97%

Section: Many Plants Of the Euphorbiaceae Possess Latex That Ij Rich mentioning

confidence: 99%

Phytochemistry and Systematics of the Euphorbiaceae

Seigler¹

1994

Annals of the Missouri Botanical Garden

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“…Hopane-like compounds are present in a number of prokaryotes including Nostoc, and it is thought that they are components of membranes, analogous to sterols in eukaryotic cells. They are thought to be primitive phylogenetic precursors of sterols, de-rived from the same precursor squalene, but cyclised in the absence of oxygen and possibly representing persistence of a chemical adaptation compatible with archaebiotic, prephotosynthetic conditions (Ourisson et al, 1979). The similarity of lichen hopanes which are produced in quantity in species of Nephroma, Peltigera, and PseudocypheUaria in cool temperate habitats, and of hopane biomarkers (such as 17a 21B hopane and 17B 21a hopane) used by petroleum chemists when assaying oil deposits in various geological formations, suggests the possibility of relating chemical structures to geological formations of known age, which may have important implications in phylogenetic reconstructions in the Peltigerales (Galloway, 1991c).…”

Section: Chemistrymentioning

confidence: 99%

Ascomycete Systematics

1994

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A series presenting the results of activities sponsored by the NA TO Science Committee, which aims at the dissemination of advanced scientific and technological knowledge, with a view to strengthening links between scientific communities.The series is published by an international board of publishers in conjunction with the Library of Congress Cataloging in Publication InformationOn file ISBN 978-1-4757-9292-8 ISBN 978-1-4757-9290-4 (eBook) All rights reservedNo part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher

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“…These specialized cells represent a closed system devoted to the production and storage of latex, a white, milky liquid [4]. This latex is characterized by a high content of isoprenoids, mainly triterpenes with a rather large structural diversity [5,6], and to a lesser extent of diterpenoids, most of them being irritant toxics, causing intense inflammatory reactions and acting often as procarcinogens [7,8]. The triterpene fingerprint of Euphorbia latex has been used as chemotaxonomic marker and allowed division of the huge genus Euphorbia into subgroups according to the triterpene composition of the latex [5,6].…”

Section: Introductionmentioning

confidence: 99%

“…This latex is characterized by a high content of isoprenoids, mainly triterpenes with a rather large structural diversity [5,6], and to a lesser extent of diterpenoids, most of them being irritant toxics, causing intense inflammatory reactions and acting often as procarcinogens [7,8]. The triterpene fingerprint of Euphorbia latex has been used as chemotaxonomic marker and allowed division of the huge genus Euphorbia into subgroups according to the triterpene composition of the latex [5,6]. Plant triterpenes are derived from enzymatic cyclization of oxidosqualene and are characterized by a C 30 H 50 O crude chemical formula [9,10,11], which makes them suitable for fuel production by the methods used by the oil industry [12,13].…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Isoprene Units in Euphorbia lathyris Laticifers vs. Other Tissues: MVA and MEP Pathways, Compartmentation and Putative Endophytic Fungi Contribution

et al. 2019

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Euphorbia species are characterized by a net of laticifers producing large amounts of triterpenes. These hydrocarbon-like metabolites can be converted into fuel by the methods of the oil industry. Euphorbia lathyris is easily grown at an industrial scale. In an attempt to increase its triterpene production, the metabolic pathways leading to isoprenoid were investigated by incorporation of 13C labeled glucose and mevalonate and 2H labeled deoxyxylulose as well as by natural abundance isotope ratio GC-MS. Latex triterpenes are exclusively synthesized via the mevalonate (MVA) pathway: this may orient future search for improving the triterpene production in E. lathyris. Phytosterols and their precursors are mainly derived from MVA pathway with a slight contribution of the methylerythritol phosphate (MEP) pathway, whereas phytol is issued from MEP pathway with a minor contribution of the MVA pathway: this is in accordance with the metabolic cross-talk between cytosolic and plastidial compartments in plants. In addition, hopenol B behaved differently from the other latex triterpenes. Its 13C isotope abundance after incorporation of 13C labeled glucose and its natural abundance δ2H signature clearly differed from those of the other latex triterpenes indicating another metabolic origin and suggesting that it may be synthesized by an endophytic fungus.

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From Terpenes to Sterols: Macroevolution and Microevolution

Cited by 10 publications

References 23 publications

Phytochemistry and Systematics of the Euphorbiaceae

Phytochemistry and Systematics of the Euphorbiaceae

Ascomycete Systematics

Biosynthesis of Isoprene Units in Euphorbia lathyris Laticifers vs. Other Tissues: MVA and MEP Pathways, Compartmentation and Putative Endophytic Fungi Contribution

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