Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula

Klischies, Martina; Zenk, Meinhart H.

doi:10.1016/s0031-9422(00)94574-6

Cited by 20 publications

(4 citation statements)

References 6 publications

(2 reference statements)

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“…Hirsutanonol (19); oregonin (27); genkwanin (164); rhododendrin {3-(4-hydroxyphenyl)-l-methylpropyl-β-D-glucopyranoside} (167) and glutinic acid (2,3-pentadienedioic acid) (168). [ 74 – 77 ]…”

Section: Chemical Constituents Of Genus Alnusmentioning

confidence: 99%

Bioactive constituents and medicinal importance of genus Alnus

Sati

2011

Phcog Rev

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The genus Alnus has been reviewed for its chemical constituents and biological activities including traditional importance of some common species. The plants of this genus contain terpenoids, flavonoids, diarylheptanoids, phenols, steroids, and tannins. Diarylheptanoids are the dominant constituents within the genus Alnus, few of them exhibited antioxidant effects and inhibitory activity against nuclear factor kappaB activation, nitric oxide and tumor necrosis factor-α production, human umbilical vein endothelial cells, farnesyl protein transferase, cell-mediated low-density lipoprotein oxidation, HIF-1 in AGS cells, and the HIV-1-induced cytopathic effect in MT-4 cells. Some ellagitannines showed hepatoprotective activity even in a dose of 1 mg/kg which is ten-fold smaller compared with the dose of traditional flavonoid-based drugs. The members of genus Alnus are well known for their traditional uses in the treatment of various diseases like cancer, hepatitis, inflammation of uterus, uterine cancer, rheumatism, dysentery, stomachache, diarrhea, fever, etc. The aim of the present review is to summarize the various researches related to the chemistry and pharmacology of genus Alnus.

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Section: Chemical Constituents Of Genus Alnusmentioning

confidence: 99%

Bioactive constituents and medicinal importance of genus Alnus

Sati

2011

Phcog Rev

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“…Biosynthetically, these stuctures are derived from a cinnamic acid derivative which is subsequently reduced to a dihydrocinnamoyl alcohol. Finally, an additional methyl group is transferred enzymatically from SAM [88]. Similar to the biosynthesis of diarylheptanoids, e.g., acerogenin A [89], the curcuminoids [90][91][92] or gingerols [91][92][93], the aglycon of cmpd.…”

Section: Discussionmentioning

confidence: 99%

Anthelmintic A-Type Procyanidins and Further Characterization of the Phenolic Composition of a Root Extract from Paullinia pinnata

Spiegler

2020

Molecules

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Extracts from the roots of Paullinia pinnata L. are used in West Africa as traditional remedies for a variety of diseases including infestations with soil-transmitted helminths. Based on the results of an ethnopharmacological survey in Ghana, an aqueous acetone (70%) extract was investigated for its anthelmintic and phytochemical properties. Partitioning of the crude extract followed by several fractionation steps of the ethyl acetate phase using Sephadex® LH-20, fast centrifugal partition chromatography, RP-18-MPLC and HPLC led to isolation of six oligomeric A-type procyanidins (1 to 6). To determine the anthelmintic activity, the crude extract, fractions and isolated compounds were tested in vitro against the model organism Caenorhabditis elegans. A significantly better activity was observed for the trimeric A-type procyanidin (1) compared to a B-type trimer. However, this effect could not be generalized for the tetrameric procyanidins, for which the type of the interflavan-linkage (4→6 vs. 4→8) had the greatest impact on the bioactivity. Besides the procyanidins, three novel compounds, isofraxidin-7-O-α-l-rhamnopyranosyl-(1″→6′)-β-d-glucopyranoside (17), 4-methoxycatechol-2-O-(5′′-O-vanilloyl-β-apiofuranosyl)-(1′′→2′)-β-glucopyranoside (18) and a 6-(3-methoxy-4-hydroxyphenyl)-hexane-2,4-diol-2-O-hexoside (19) were isolated together with further ten known compounds (7 to 16), mainly coumarins and coumarinolignans. Except for 3-β-d-glucopyranosyloxy-4-methyl-2(5H)-furanone (15), none of the isolated compounds has previously been described for P. pinnata. The anthelmintic activity was attributed to the presence of procyanidins, but not to any of the other compound classes. In summary, the findings rationalize the traditional use of P. pinnata root extracts as anthelmintic remedies.

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“…Flavonones 189 – 195 ( Table 13 ) were found in A. sieboldiana , Alnus pendula Matsum., Alnus maximowiczii Call., Alnus firma S.Z. and A. glutinosa [ 49 , 50 , 51 , 52 , 53 ]. Two flavanonols 197 and 198 are shown in Figure 8 .…”

Section: Chemical Constituentsmentioning

confidence: 99%

The Genus Alnus, A Comprehensive Outline of Its Chemical Constituents and Biological Activities

et al. 2017

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The genus Alnus (Betulaceae) is comprised of more than 40 species. Many species of this genus have a long history of use in folk medicines. Phytochemical investigations have revealed the presence of diarylheptanoids, polyphenols, flavonoids, terpenoids, steroids and other compounds. Diarylheptanoids, natural products with a 1,7-diphenylheptane structural skeleton, are the dominant constituents in the genus, whose anticancer effect has been brought into focus. Pure compounds and crude extracts from the genus exhibit a wide spectrum of pharmacological activities both in vitro and in vivo. This paper compiles 273 naturally occurring compounds from the genus Alnus along with their structures and pharmacological activities, as reported in 138 references.

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Stereochemistry of C-methylation in the biosynthesis of rhododendrin in Alnus and Betula

Cited by 20 publications

References 6 publications

Bioactive constituents and medicinal importance of genus Alnus

Bioactive constituents and medicinal importance of genus Alnus

Anthelmintic A-Type Procyanidins and Further Characterization of the Phenolic Composition of a Root Extract from Paullinia pinnata

The Genus Alnus, A Comprehensive Outline of Its Chemical Constituents and Biological Activities

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