[reaction: see text] Total syntheses of seven biologically important lignan natural products, including (-)-arctigenin, (-)-matairesinol, and (-)-alpha-conidendrin, by way of a highly stereoselective domino radical sequence is presented. The reported stereochemistry of the natural product 7-hydroxyarctigenin is shown to be erroneous; a diastereoisomeric structure is assigned to the natural product.

Download full-text PDF

Source
http://dx.doi.org/10.1021/ol049878bDOI Listing

Publication Analysis

Top Keywords

--arctigenin --matairesinol
8
natural products
8
natural product
8
radical carboxyarylation
4
carboxyarylation approach
4
approach lignans
4
lignans total
4
total synthesis
4
synthesis --arctigenin
4
natural
4

Similar Publications

The fruit of (Thunb.) Vahl has been used in traditional Chinese medicine as "". The species is also grown in parks and gardens, and on streets and building lots, as an ornamental plant, but it requires pruning.

View Article and Find Full Text PDF

Arctigenin is a bioactive dibenzylbutyrolactone-type lignan exhibiting various pharmacological activities. The neuroprotective effects of arctigenin were demonstrated to be mediated via inhibition of AMPA and KA type glutamate receptors in the somatosensory cortex of the rat brain. The aim of this study was to compare the effects of arctigenin with matairesinol and trachelogenin on synaptic activity in rat brain slices.

View Article and Find Full Text PDF

Chromatographic fingerprint combined with quantitative analysis of multi-components by single-marker for quality control of total lignans from Fructus arctii by high-performance liquid chromatography.

Phytochem Anal

December 2022

Innovative Chinese Medicine Research Institute, Engineering Research Centre of Modern Preparation Technology of Traditional Chinese Medicine, Ministry of Education, Shanghai University of Traditional Chinese Medicine, Shanghai, China.

Introduction: The total lignans from Fructus arctii (TLFA) is a mixture of a series of lignans isolated from dried ripe fruit of Arctium lappa L. We previously reported on the pharmacological activity of TLFA that is related to diabetes. An accurate and practical TLFA quantitative analysis method for utilising it needs to be established.

View Article and Find Full Text PDF

Phytochemical investigation of the aerial parts obtained from the Turkish plant Centaurea kotschyi subsp. persica led to the isolation of nine sesquiterpene lactones belonging to the guaiane class, including the undescribed kotschyols A and B, a monoterpene lactone (daphnauranin E), four known lignans (matairesinol, matairesinoside, arctiin and arctigenin) and an undescribed dihydrobenzofuran neolignan (4-O-glucosylcrataegifin A). The structures of these compounds were defined by spectroscopic analysis, including ECD and 1D/2D NMR, and chemical conversion.

View Article and Find Full Text PDF

Seven sesquiterpene lactones, chlorophyssopifolin E (), aguerin B (), repdiolide triol (), solistitiolide (), aitchisonolide (), sinicin B (), cynaropicrin (), along with four lignans arctigenin (), arctiin (), matairesinol (), and matairesinoside () were isolated for the first time from the aerial parts of Bornm. Among the isolated compounds, aguerin B () showed the most cytotoxic activity against MCF7 cell lines with IC value of 18.9 μM.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!