839. Triterpenoids in the bark of mountain ash (sorbus aucuparia L.)

Lawrie, W.; McLean, John H.; Taylor, George R.

doi:10.1039/jr9600004303

Cited by 12 publications

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“…Various acidic conditions have been applied for this transformation, which is now known to belong to the class of Wagner-Meerwein rearrangements. Hydrobromic acid in chloroform [ 9 ], sulfuric acid in acetic acid [ 10 ], concentrated hydrochloric acid in ethanol [ 11 , 12 ] and even the highly toxic dimethyl sulfate [ 13 ] have been used for the transformation of 1 to 2 in moderate to good yields. The yield can be substantially improved by using acid reagents adsorbed on solid supports.…”

Section: Betulin-allobetulin Rearrangementmentioning

confidence: 99%

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Allobetulin and Its Derivatives: Synthesis and Biological Activity

2011

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This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last part, the most important biological activities of allobetulin derivatives are listed. One hundred and fifteen references are cited and the relevant literature is covered, starting in 1922 up to the end of 2010.

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Section: Betulin-allobetulin Rearrangementmentioning

confidence: 99%

“…The naturally occurring 23-hydroxybetulin ( 13 , obtained from the bark of Sorbus aucuparia L.) was transformed to the diformate 14a (R = CHO) by an adaptation of the Schulze-Pieroh procedure [ 11 ]. Removal of the formate lead to 23-hydroxyallobetulin ( 14b , R = H).…”

Section: Betulin-allobetulin Rearrangementmentioning

confidence: 99%

Allobetulin and Its Derivatives: Synthesis and Biological Activity

2011

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“…(1979) gave the chemical composition of the bark (per cent dry weight, with 95% confidence limits): ash 4.8 ± 0.3, Ca 1.6 ± 0.2, K 0.4 ± 0.1, Na 0.02 ± 0.01, Mg 0.15 ± 0.02, P 0.07 ± 0.01, tannins 7.9 ± 1.4, pH 4.6–5.2. Lawrie et al . (1960) isolated lupeol, betulin and 23‐hydroxybetulin from the bark.…”

Section: Structure and Physiologymentioning

confidence: 99%

Sorbus aucuparia L.

Findlay²,

2000

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“…Nonetheless, the first of these peaks has a significantly lower RI (3551) than that assigned to betulin in the NIST database (RI = 3740). At the same time, it is known that rowan bark contains not only betulin but also its isomer allobetulin, which has higher chromatographic mobility due to the replacement of the alcohol group by an ether one, without a change in spectral data [ 30 ].…”

Section: Resultsmentioning

confidence: 99%

A GC-MS Chemotaxonomic Study on Lipophilic Compounds in the Bark of S. aucuparia subsp. sibirica Trees from the Population Growing in Akademgorodok, Novosibirsk (Russia)

et al. 2023

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Determination of chemotypes and of their role in the polymorphism of populations is an important field in the research on secondary metabolites of plants. In the present study, by gas chromatography coupled with mass spectrometry, the composition of bark extracts from rowan S. aucuparia subsp. sibirica was determined for 16 trees growing within Akademgorodok of Novosibirsk, with bark samples collected both in winter and summer. Among 101 fully or partially identified metabolites, there are alkanes, alkenes, linear alcohols, fatty acids and their derivatives, phenols and their derivatives, prunasin and its parent and derivative compounds, polyprenes and their derivatives, cyclic diterpenes, and phytosterols. These compounds were grouped according to their biosynthesis pathways. Cluster analysis revealed two groups among the bark samples collected in winter and three groups among bark samples collected in summer. The key determinants of this clustering are the biosynthesis of metabolites via the cyanogenic pathway (especially potentially toxic prunasin) and their formation via the phytosterol pathway (especially potentially pharmacologically useful lupeol). It follows from the results that the presence of chemotypes having sharply different profiles of metabolites in a population from a small geographic area invalidates the practice of general sampling to obtain averaged data when a population is described. From the standpoint of possible industrial use or plant selection based on metabolomic data, it is possible to select specific sets of samples containing a minimal amount of potentially toxic compounds and the largest amount of potentially useful substances.

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839. Triterpenoids in the bark of mountain ash (sorbus aucuparia L.)

Cited by 12 publications

References 0 publications

Allobetulin and Its Derivatives: Synthesis and Biological Activity

Allobetulin and Its Derivatives: Synthesis and Biological Activity

Sorbus aucuparia L.

A GC-MS Chemotaxonomic Study on Lipophilic Compounds in the Bark of S. aucuparia subsp. sibirica Trees from the Population Growing in Akademgorodok, Novosibirsk (Russia)

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