170. Triterpenes of the friedelane series. Part III. The course of the friedelene–oleanene rearrangement

Courtney, J.L.; Gascoigne, R. M.; Szumer, A. Z.

doi:10.1039/jr9580000881

Cited by 20 publications

(7 citation statements)

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“…Pentacyclic triterpenes are known to undergo structural rearrangements (Courtney et al, 1958;Coates, 1967;Chatterjee et al, 1976;Ageta et al, 1987;Rullkötter et al, 1994). For example, ten Haven et al ( 1992) have shown that taraxerane-type structures are converted into thermodynamically more stable oleanane-type compounds.…”

Section: Diagenesis Of Ptmesmentioning

confidence: 99%

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Jacob

Disnar

Boussafir

et al. 2005

Organic Geochemistry

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The lipid extracts of sediments collected from the Quaternary filling of a tropical lacustrine series (Lagoa do Caçó, Brazil) were investigated by gas chromatography-mass spectrometry (GC-MS). Various pentacyclic triterpene 3-methyl ethers (PTMEs) were present in the neutral fraction. Comparison of retention times and mass spectra with available standards allowed us to certify the presence of olean-12-en-3β-ol ME (β-amyrin ME), olean-18-en-3β-ol ME (miliacin), taraxer-14-en-3β-ol ME (crusgallin), fern-9(11)-en-3β-ol ME (arundoin) and arbor-9(11)-en-3β-ol ME (cylindrin). The following other compounds coud also be tentatively identified from their GC-MS characteristics: urs-12-en-3β-ol ME, bauer-7-en-3β-ol ME and fern-8-en-3β-ol ME. Other compounds such as possible 3α isomers of the PTMEs as well as di-or tri-unsaturated counterparts might be PTME diagenetic derivatives. According to previous chemotaxonomic studies, all these compounds most probably originate from Gramineae that used to colonize the savannas of Northern Brazil at the time of deposition.

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Section: Diagenesis Of Ptmesmentioning

confidence: 99%

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Jacob

Disnar

Boussafir

et al. 2005

Organic Geochemistry

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“…Rullkötter et al, 1994). This phenomenon that is well documented from laboratory experiments for compounds the oleanane series (Courtney et al, 1958;Coates et al, 1967), is also observed in sedimentary records (Rullkötter et al, 1994). Precisely, friedel-3-ene, glutin-5-ene, multiflor-7-ene and taraxer-14-ene are progressively rearranged to olean-18-ene, olean-12-ene and finally olean-13(18)-ene isomers.…”

Section: Comparison Of Soil Triterpenyl Acetate Diversity With Local mentioning

confidence: 60%

Occurrence of triterpenyl acetates in soil and their potential as chemotaxonomical markers of Asteraceae

Lavrieux

Jacob

Milbeau

et al. 2011

Organic Geochemistry

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As a part of a wider study aimed at determining new molecular biomarkers in soils and sediments that could be specific of distinct vegetation types with respect to unravelling past changes in land use, we analysed the neutral lipid content of soil developed in the catchment of a small lake in central France. The ketone/acetate lipid fraction of soil under pasture or meadow contains a series of pentacyclic triterpenyl acetates of wide structural diversity, most being reported in soil for the first time. The restricted number of potential plant sources of triterpenyl acetates (some produced by a single species) underlines the potential of triterpenyl acetates as new biomarkers to track past vegetation change in palaeoenvironmental studies, when found in natural archives such as soil, sediments or peat.

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“…Taraxaryl acetate (371-0Ac) (459), various taraxarane derivatives (460)(461)(462), and multiftorenyl acetate (372-0Ac) ( 463) are readily isomerized to ß-amyrin acetate (352-0Ac), or the corresponding N 2 -oleanene. The relief of a severe steric interaction between the :x-oriented methyl groups at C13 and C20 is considered to be a major driving force in these rearrangements.…”

Section: References Pp 205-230mentioning

confidence: 99%

Biogenetic-Type Rearrangements of Terpenes

Coates

1976

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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170. Triterpenes of the friedelane series. Part III. The course of the friedelene–oleanene rearrangement

Cited by 20 publications

References 0 publications

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Pentacyclic triterpene methyl ethers in recent lacustrine sediments (Lagoa do Caçó, Brazil)

Occurrence of triterpenyl acetates in soil and their potential as chemotaxonomical markers of Asteraceae

Biogenetic-Type Rearrangements of Terpenes

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