An epoxy-trinoreudesmane sesquiterpene from the liverwort Lophocolea bidentata

Rieck, Angela; Bülow, Nils; König, Wilfried Α.

doi:10.1016/0031-9422(95)00355-b

Cited by 18 publications

(11 citation statements)

References 8 publications

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“…trans-Configuration was assumed for the decaline skeleton for the following reasons: the methine proton H-6 has three axial coupling constants (δ 0.99, ddd, J 1 = 12. 3 (1) Hz, J 3 = 3.63 Hz). These facts also imply an equatorial position for the tetrahydrofuran ring, since H-5 and H-7 occupy the axial positions.…”

Section: Resultsmentioning

confidence: 94%

“…The protons of these two methyl groups show connectivity to the quaternary carbon atom C-11 (δ 82.1) and to the tertiary carbon atom C-7 (δ 52.8). This indicated that the two methyl groups are located on carbon C-11 (δ 82.1), which also bears an oxygen atom resulting in the partial structure CH 3 -C(O)-CH 3 . The protons of the methylene CH 2 -9 showed connectivity to the carbons C-1, C-7, C-9 and C-10.…”

Section: Resultsmentioning

confidence: 97%

“…GC-MS analysis of the hydrodistillation product of fresh plants of A. caucasicus revealed the presence of several monoterpene hydrocarbons [α-pinene (8.7%), camphene, β-pinene, myrcene, p-cymene, limonene (10.5%), γ-terpinene, terpinolene], the trinorsesquiterpene 4,8a-dimethyl-4a,5-epoxy-decalin, 3 sesquiterpenes, including anastreptene, β-elemene, aristolene, calarene, α-barbatene, β-barbatene (6.7%), allo-aromadendrene, bicyclogermacrene (4.9%), α-cuprenene (3.6%), β-bisabolene (2.7%), and traces of β-sesquiphellandrene, β-bazzanene and δ-cuprenene. In the high-boiling region of the gas chromatogram, E-nerolidol, maaliol, palustrol, spathulenol, viridiflorol, rosifoliol, 5-guaiene-11-ol, diplophyllolide, 16-kaurene and isoabienol were detected ( Figure 1).…”

Section: Resultsmentioning

confidence: 99%

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Chemical constituents of the essential oil of the hornwort Anthoceros caucasicus

Sonwa

König

2003

Flavour & Fragrance J

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

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Chemical constituents of the essential oil of the hornwort Anthoceros caucasicus

Sonwa

König

2003

Flavour & Fragrance J

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“…[69] The highly fragrant compound occurring in the EO of L. bidentata was epoxy-trinoreudesmane sesquiterpene (100). [70] The most characteristic components occurring in the Lophocolea species are furanoeudesmanes and 12,8-eudesmanolides. [11,23] Both types of compound were found in the EOs hydrodistilled from Lophocolea species.…”

Section: Leafy Liverwortsmentioning

confidence: 99%

“…ent-Isoalantolactone (101) [68] and furanoeudesma-4(15),7,11-trien-5a-ol (102) [71] were detected in L. heterophylla, while the presence of diplophyllolide (90) was confirmed in L. bidentata (Figure 10). [68,70] Other Studies Concerning EOs from Liverworts…”

Section: Leafy Liverwortsmentioning

confidence: 99%

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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A Detailed View on Geosmin Biosynthesis

Dickschat

2023

ChemBioChem

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The bacterial geosmin synthase is a fascinating bifunctional enzyme that has been discovered almost two decades ago. Several aspects of the cyclisation mechanism from FPP to geosmin are known, but a detailed picture of the stereochemical course of this reaction is unknown. This article reports on a deep investigation of the mechanism of geosmin synthase through isotopic labelling experiments. Furthermore, the effects of divalent cations on geosmin synthase catalysis were investigated. The addition of cyclodextrin to enzymatic reactions, a molecule that can capture terpenes, suggests that the biosynthetic intermediate (1(10)E,5E)‐germacradien‐11‐ol produced by the N‐terminal domain is passed to the C‐terminal domain not through a tunnel, but rather through release into the medium and uptake by the C‐terminal domain.

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An epoxy-trinoreudesmane sesquiterpene from the liverwort Lophocolea bidentata

Cited by 18 publications

References 8 publications

Chemical constituents of the essential oil of the hornwort Anthoceros caucasicus

Chemical constituents of the essential oil of the hornwort Anthoceros caucasicus

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

A Detailed View on Geosmin Biosynthesis

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