Bioactive tetrahydrofuran lignans from roots, stems, leaves and twigs of Anogeissus rivularis

Synthesis of novel 2-methyl-3-furyl sulfide flavor derivatives as efficient preservatives

“…In this study, a series of 2-methyl-3-furyl sulde derivatives with fragrance and avor were synthesized by reactions of 2-methyl-3-furyl disulde with cyclic ethers, amides, ketones, and epoxides, respectively (Scheme 1). [18][19][20][21] These synthesized 2-methyl-3furyl sulde derivatives are expected to be volatile and may exhibit different bioactivities, because tetrahydrofuran, 22 1,4dioxane, 23 amides, 24 ketones, 23 and epoxides, 25 are important pharmacophore for drug design. Derivatives 3a-3i were synthesized by the C-H sulfurization of 2-methyl-3-furyl disul-de with cyclic ethers and amides, respectively.…”

Asymmetric Synthesis of ent-Anorisol A and Its Stereoisomers and Confirmation of the Absolute Configuration of Anorisol A Isolated from Anogeissus rivularis

“…R f = 0.40 (40% EtOAc in hexanes); [α] D 23 –61.9 ( c 0.4, MeOH) {Lit. 2 [α] D 24 +48.2 ( c 0.4, MeOH)}.…”

“…Usually, the relative stereochemistry across the THF ring of a new naturally occurring 2,5-diaryl-3,4-dimethyltetrahydrofuran is assigned by comparison of the observed spectroscopic data, especially the vicinal coupling constant values, with those of related natural derivatives reported in the literature. 2 3a d e We therefore envisioned that the conformational analysis of the THF cores 11 of the synthesized 1a , 1b , and 1c with respect to their vicinal coupling constant values would be of importance. This information should be a useful reference for the assignment of the stereochemistry of other related THF lignans.…”

“…Anorisol A ( 1 ) is a naturally occurring 2,5-diaryl-3,4-dimethyltetrahydrofuran 1 recently reported to be isolated from the roots, stems, leaves, and twigs of Anogeissus rivularis (Combretaceae) plant grown in the north-eastern part of Thailand (Figure 1 ). 2 The chemical structure of 1 was elucidated on the basis of its spectroscopic profiles and by comparison with literature data. The uncommon 2,3- anti -3,4- syn -4,5- syn relative stereochemistry 3 with 2 R ,3 R ,4 S ,5 R configurations of 1 was established by comparison of the electronic circular dichroism (ECD) spectra with the calculated ECD spectra.…”

The antioxidant activity of tetrahydrofuran lignans from Anogeissus rivularis: theoretical insights into the radical scavenging activity and enzyme inhibition

“…1) from Anogeissus rivularis. 3 Reverse transcriptase and syncytium reduction assays were used to assess the cytotoxic and anti-HIV-1 activities of the compounds; at 200 g mL À1 , compound 1 inhibited reverse transcriptase by 76.0% (IC 50 = 213.9 M). Effective antioxidant characteristics of these substances have been demonstrated experimentally, 7,[9][10][11] providing an impetus for a theoretical examination of their free radical scavenging capacity.…”