Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania

Andersen, N.H.; Bissonette, P.; Liu, C. B.; Shunk, Belinda; Ohta, Yoshimoto; Tseng, Chia Li W; Moore, Ana L.; Huneck, Siegfried

doi:10.1016/0031-9422(71)85081-1

Cited by 78 publications

(26 citation statements)

References 72 publications

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“…This compound was the major volatile component in Bazzania trilobata. [38] Its presence was also confirmed in B. tricrenata [38] and B. pompeana. [35] Anastrepta orcadensis produces anastreptene (7) and β-barbatene (8) as the major EO components, while α-(19) and β-barbatene (8) together with α-longipinene (4) were found in Lepidozia reptans.…”

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 82%

“…Studies on the chemical composition of EOs obtained from liverworts carried out at the end of 1960s and in the early 1970s showed that these plants are an unusually rich source of sesquiterpenes, which in many cases are enantiomeric to those found in vascular plants. [33][34][35][36][37][38] The first well-documented study on liverwort components conducted by Huneck and Klein [31] indicated the presence of (À)-longiborneol (1) and (À)-longifolene (2) in the essential oil from the leafy liverwort Scapania undulata. Andersen and coworkers [38] confirmed the presence of both components in EO of S. undulata, and additionally identified longipinanol (3), α-(4) and β-longipinene (5), longicyclene (6) from the longifolane group and also anastreptene (7), β-barbatene (8), caryophyllene (9), α-(10) and δ-himachalene (11), and β-chamigrene (12).…”

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

“…[33][34][35][36][37][38] The first well-documented study on liverwort components conducted by Huneck and Klein [31] indicated the presence of (À)-longiborneol (1) and (À)-longifolene (2) in the essential oil from the leafy liverwort Scapania undulata. Andersen and coworkers [38] confirmed the presence of both components in EO of S. undulata, and additionally identified longipinanol (3), α-(4) and β-longipinene (5), longicyclene (6) from the longifolane group and also anastreptene (7), β-barbatene (8), caryophyllene (9), α-(10) and δ-himachalene (11), and β-chamigrene (12). Other studies showed that longifolane-type sesquiterpenoids were absent in S. parvitexta: this liverwort species contained β-cubebene (13), calamenene (14), β-chamigrene (12), β-selinene (15), bazzanene (16), and cuparene (17).…”

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

“…Unfortunately the structures of asperene and aequilobene remain to be unidentified. [38] The most characteristic component detected in the EOs from Bazzania species is bazzanene (16). This compound was the major volatile component in Bazzania trilobata.…”

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

“…[35] Anastrepta orcadensis produces anastreptene (7) and β-barbatene (8) as the major EO components, while α-(19) and β-barbatene (8) together with α-longipinene (4) were found in Lepidozia reptans. [38] The major component of EO from Diplophyllum albicans and D. taxifolium was diplophyllin (20), belonging to the ent-eudesmanolides group. Among the more polar constituents of both Diplophyllum species were 9α-acetoxydiplophyllin A. Ludwiczuk and Y. Asakawa (21), and several sesquiterpene alcohols including albicanol (22) (Figure 1).…”

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

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Chemotaxonomic value of essential oil components in liverwort species. A review

Ludwiczuk

Asakawa

2015

Flavour & Fragrance J

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A number of liverwort species are known to emit volatile terpenoids and simple aromatic compounds when crushed. The characteristic odour of these spore-forming plants is associated with oil body constituents. Secondary metabolites, which constitute the oil bodies, are also of value for taxonomic investigations. Liverworts have yielded a rich array of secondary metabolites. Many of these compounds are characterized by unique structures, and some of them have not been found in any other plants, fungi, or marine organisms. Gas chromatographic profiling of the volatile extracts obtained from the liverworts has been applied with success in differentiating liverworts species, and also used to resolve the taxonomic problems at genus and family level. Due to the fact that liverworts are morphologically very small and it is difficult to collect a sufficient amount of plant material, there are few research data on the composition of the essential oils obtained from these plants. Nevertheless, the available data indicate that, as in the case of aromatic plants, the components present in essential oils obtained from the liverworts can be used in chemosystematic studies of this plant group. The aim of this paper is to show whether: (i) there are differences in the essential oils composition between different liverwort species; (ii) it is possible to find chemical markers characteristic for the analysed liverwort species; and (iii) the data derived from an analysis of the essential oils are in accordance with the data received from volatile extracts.

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Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 82%

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

Section: Early Studies On the Essential Oils From Liverwort Speciesmentioning

confidence: 99%

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Chemotaxonomic value of essential oil components in liverwort species. A review

Ludwiczuk

Asakawa

2015

Flavour & Fragrance J

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Gold(I)‐Catalyzed Intramolecular Cyclopropanation of Dienynes

Nieto‐Oberhuber

López

Muñoz

et al. 2006

Chemistry A European J

166

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Gold(I) complexes are the most active catalysts for the biscyclopropanation of dienynes to form tetracyclic compounds. PtII and ZnII are also able to promote the biscyclopropanation, although less efficiently. The configurations obtained in all cases with the use of gold(I) catalysts can be explained by the pathway proceeding through anti cyclopropyl gold carbenes. Similar intermediates are most probably involved in reactions catalyzed by RuII and PtII. Two different cyclopropanation pathways have been found; they depend on the structures of the cyclopropyl gold carbenes (anti or syn) and the relative arrangements of the metal carbenes and the alkenes.

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Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

Dickschat

2020

Chemistry A European J

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This review summarises known sesquiterpenes whose biosyntheses proceed through the intermediate germacrene A. First, the occurrencea nd biosynthesis of germacrene Ai nN ature and its peculiar chemistry will be highlighted , followed by ad iscussion of 6-6 and 5-7 bicyclic compounds and their more complex derivatives. For each compound the absolutec onfiguration, if it is known,a nd the reasoning for its assignment is presented. 2. Germacrene A 2.1. Occurrence in Nature (À)-Germacrene A(1,S cheme 2) was first isolated in 1970 from the gorgonian Eunicea mammosa. [7] Its absolute configuration was established as (S)-(À)-1 through its Cope rearrangement to (+ +)-b-elemene (2)f or which the configurational assignment was performed by chemical correlation of (À)-elemol(3)t o (À)-2. [8, 9] Compound (À)-1 is also believed to occur in the soft coral Lobophytum, [10] andi st he alarm pheromone of the aphid Terioaphis maculata. [11, 12] In the course of this work it was noticed that the optical rotation([ a] D 25 = À26.8, c 1.0, CCl 4)w as significantly highert han initially reported ([a] D 25 = À3.2, c 14.4, CCl 4), [7] which is explainableb yapartial rearrangement of purified (À)-1 to (+ +)-2,o ra lternatively, 1 isolated from E. mammosa was not enantiomerically pure. However,the opticalrotation of (+ +)-2 ([a] D 25 =+15.1, neat) reported in this initial study [7] matches the reported value for (À)-2 ([a] D 25 = À15.8, c 0.50, CHCl 3)o btainedb yC ope rearrangement of (+ +)-1, [13] thus disfa-Scheme1.Te rpene cyclisation modes for FPP. Scheme2.Structure of 1 and its absolute configurationbyc hemicalcorrelation.

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Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania

Cited by 78 publications

References 72 publications

Chemotaxonomic value of essential oil components in liverwort species. A review

Chemotaxonomic value of essential oil components in liverwort species. A review

Gold(I)‐Catalyzed Intramolecular Cyclopropanation of Dienynes

Germacrene A–A Central Intermediate in Sesquiterpene Biosynthesis

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