Biogenetic Aspects of Sesquiterpene Lactone Chemistry

Herz, Werner

doi:10.1002/ijch.197700010

Cited by 65 publications

(25 citation statements)

References 143 publications

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“…Hydrocortisone, which is used as internal standard, was clustered together with the annotated STL. This proximity can be explained by the same biosynthetic origin that these compounds share (mevalonate/methylerythritol phosphate pathway) [28,29].…”

Section: Resultsmentioning

confidence: 99%

Natural Products Diversity in Plant-Insect Interaction between Tithonia diversifolia (Asteraceae) and Chlosyne lacinia (Nymphalidae)

et al. 2019

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The chemical ecology of plant-insect interactions has been driving our understanding of ecosystem evolution into a more comprehensive context. Chlosyne lacinia (Lepidoptera: Nymphalidae) is an olygophagous insect herbivore, which mainly uses host plants of Heliantheae tribe (Asteraceae). Herein, plant-insect interaction between Tithonia diversifolia (Heliantheae) and Chlosyne lacinia was investigated by means of untargeted LC-MS/MS based metabolomics and molecular networking, which aims to explore its inherent chemical diversity. C. lacinia larvae that were fed with T. diversifolia leaves developed until fifth instar and completed metamorphosis to the adult phase. Sesquiterpene lactones (STL), flavonoids, and lipid derivatives were putatively annotated in T. diversifolia (leaves and non-consumed abaxial surface) and C. lacinia (feces, larvae, pupae, butterflies, and eggs) samples. We found that several furanoheliangolide-type STL that were detected in T. diversifolia were ingested and excreted in their intact form by C. lacinia larvae. Hence, C. lacinia caterpillars may have, over the years, developed tolerance mechanisms for STL throughout effective barriers in their digestive canal. Flavonoid aglycones were mainly found in T. diversifolia samples, while their glycosides were mostly detected in C. lacinia feces, which indicated that the main mechanism for excreting the consumed flavonoids was through their glycosylation. Moreover, lysophospholipids were predominately found in C. lacinia samples, which suggested that they were essential metabolites during pupal and adult stages. These findings provide insights into the natural products diversity of this plant-insect interaction and contribute to uncovering its ecological roles.

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Section: Resultsmentioning

confidence: 99%

Natural Products Diversity in Plant-Insect Interaction between Tithonia diversifolia (Asteraceae) and Chlosyne lacinia (Nymphalidae)

et al. 2019

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“…We should also consider that the four possible isomers of farnesyl p yrophosphate: Cordell, 1976 andHerz, 1977). It is incongruous that diterpene biosynthesis should proceed through only one precursor.…”

Section: Jalropha Gossypifolia Lmentioning

confidence: 99%

The biosynthesis of tigliane and related diterpenoids; an intriguing problem

Schmidt

1987

Botanical Journal of the Linnean Society

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The biosynthesis of tigliane and related diterpenoids; an intriguing problem. An hypothesis to explain the relationships between various diterpenoids found in members of the Euphorbiaceae is proposed. The likely nature of the tetraprenyl pyrophosphate precursor is considered, as is the manner in which the precursor may cyclize. It is thought that up to eight possible precursors may exist, being the various cisjtrans isomers of geranyl‐geranyl pyrophosphate. This suggestion arises from an acceptance of the now well‐established (but as yet unproven) process of an initial head‐to‐taiF cyclization of the precursor to form the variously cyclized hydrocarbon skeletons of tigliane and related diterpenoids. It is considered that the necessary isomerization of up to three of the prenyl units, as would have to be the case if the tigliane skeleton were produced from the all‐trans geranyl‐geranyl pyrophosphate, is not reconcilable with an initial head‐to‐tail cyclization of the precursor either on the grounds of spatial considerations or on the evidence of the currently known chemical variation in the whole family of compounds.

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“…Guaianoliden spielt(25,28,30,31),wurde zur zweifelsfreien Klarung der sich widersprechenden Angaben zur Stereostruktur eine Rontgenstrukturanalyse durchgefuhrt, die die Struktur von Baileyinacetat (lb) als Germacrolid bestatigte. Die kristallographischen Daten sind im Abschnitt Experimentelles angegeben, die Atomparameter in Tabelle 2 gelistet.…”

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Germacranolide, Guaianolide und Xanthanolide aus Blüten vonArnica mollisund Röntgenstrukturanalyse von Baileyinacetat¹

Marcinek-Hüpen-Bestendonk¹,

Willuhn²,

Steigel³

et al. 1990

Planta Med

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The flowers of ARNICA MOLLIS afforded, in addition to baileyin ( 1A), baileyin acetate ( 1B), xanthalongin ( 3), and 2-deacetoxy-11alpha,13-dihydroxanthuminol ( 6), the new 1,5- CIS-guaianolides arnimollin acetate ( 2A) and arnimollin tiglinate ( 2A) and the new xanthanolides 11beta3,13-dihydroxanthalongin ( 4) and 11alpha,13-dihydroxanthalongin ( 5). No traces of helenanolides were discernible. The structures were elucidated mainly by high-field NMR spectroscopy. The stereochemistry of 1B has been revised on the basis of an X-ray crystallographic study to be a 4alpha,5beta-epoxygermacrolide instead of a 4alpha,5beta-epoxymelampolide. The implications for the biosynthesis of CIS- and TRANS-fused guaianolides are discussed. The co-occurrence of 1A with CIS-fused guaianolides and xanthanolides (no helenanolides) in A. MOLLIS and with TRANS-fused guaianolides and helenanolides (no xanthanolides) in A. ACAULIS supports the hypothesis that germacrolides represent the biogenetic precursors for CIS- and TRANS- fused guaianolides.

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Biogenetic Aspects of Sesquiterpene Lactone Chemistry

Abstract: Abstract. Current notions concerning the biogenesis of this large group of naturally occurring substances are discussed with emphasis on stereochemical aspects.

Cited by 65 publications

References 143 publications

Natural Products Diversity in Plant-Insect Interaction between Tithonia diversifolia (Asteraceae) and Chlosyne lacinia (Nymphalidae)

Natural Products Diversity in Plant-Insect Interaction between Tithonia diversifolia (Asteraceae) and Chlosyne lacinia (Nymphalidae)

The biosynthesis of tigliane and related diterpenoids; an intriguing problem

Germacranolide, Guaianolide und Xanthanolide aus Blüten vonArnica mollisund Röntgenstrukturanalyse von Baileyinacetat¹

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Biogenetic Aspects of Sesquiterpene Lactone Chemistry

Abstract: Abstract. Current notions concerning the biogenesis of this large group of naturally occurring substances are discussed with emphasis on stereochemical aspects.

Cited by 65 publications

References 143 publications

Natural Products Diversity in Plant-Insect Interaction between Tithonia diversifolia (Asteraceae) and Chlosyne lacinia (Nymphalidae)

Natural Products Diversity in Plant-Insect Interaction between Tithonia diversifolia (Asteraceae) and Chlosyne lacinia (Nymphalidae)

The biosynthesis of tigliane and related diterpenoids; an intriguing problem

Germacranolide, Guaianolide und Xanthanolide aus Blüten vonArnica mollisund Röntgenstrukturanalyse von Baileyinacetat1

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Germacranolide, Guaianolide und Xanthanolide aus Blüten vonArnica mollisund Röntgenstrukturanalyse von Baileyinacetat¹