New flavonoids from the underground parts of Eriosema laurentii

Ateba, Sylvin Benjamin; Njamen, Dieudonné; Ukowitz, Katrin; Zehl, Martin; Kählig, Hanspeter; Hobiger, Stefanie; Jungbauer, Alois; Krenn, Liselotte

doi:10.1016/j.phytol.2016.10.003

Cited by 4 publications

(2 citation statements)

References 20 publications

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“…The PE and EtOAc fraction from the crude EtOH extract from the whole herb of R. volubilis was subjected to repeated chromatography procedures (silica gel, Toyopearl HW-40C, Sephadex LH-20, and semipreparative HPLC), leading to the isolation of five new prenylated isoflavonoids, rhynchones A-E (1-5), the structures of which were characterized by interpretation of their HRMS, 1D and 2D NMR, and electronic circular dichroism (ECD) data. Besides the five new compounds (1)(2)(3)(4)(5), a new natural product, 5′-O-methylphaseolinisoflavan (6) [22], together with twelve known compounds (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) were obtained and identified as tonkinensisol ( 7) [23], lupinifolinol (8) [24], cathayanon H (9) [25], cajanone (10) [5], prunetin (11) [26], isowighteone (12) [27], erythrinin B (13) [28], semilicoisoflavone B (14) [29], eriosemaone D (15) [30], formononetin (16) [31], puerarone (17) [32], and bidwillon C (18) [33] by comparison with literature values (▶ Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Competitive CatSper Activators of Progesterone from Rhynchosia volubilis

Xiang

Kang

et al. 2021

Planta Med

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The root Rhynchosia volubilis was widely used for contraception in folk medicine, although its molecular mechanism on antifertility has not yet been revealed. In human sperm, it was reported that the cation channel of sperm, an indispensable cation channel for the fertilization process, could be regulated by various steroid-like compounds in plants. Interestingly, these nonphysiological ligands would also disturb the activation of the cation channel of sperm induced by progesterone. Therefore, this study aimed to explore whether the compounds in R. volubilis affect the physiological regulation of the cation channel of sperm. The bioguided isolation of the whole herb of R. volubilis has resulted in the novel discovery of five new prenylated isoflavonoids, rhynchones A – E (1 – 5), a new natural product, 5′-O-methylphaseolinisoflavan (6) (1H and 13C NMR data, Supporting Information), together with twelve known compounds (7 – 18). Their structures were established by extensive spectroscopic analyses and drawing a comparison with literature data, while their absolute configurations were determined by electronic circular dichroism calculations. The experiments of intracellular Ca2+ signals and patch clamping recordings showed that rhynchone A (1) significantly reduced cation channel of sperm activation by competing with progesterone. In conclusion, our findings indicat that rhynchone A might act as a contraceptive compound by impairing the activation of the cation channel of sperm and thus prevent fertilization.

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Section: Resultsmentioning

confidence: 99%

Competitive CatSper Activators of Progesterone from Rhynchosia volubilis

Xiang

Kang

et al. 2021

Planta Med

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“…In addition, based on the analysis of NMR spectra of compounds 4–21 , 18 known compounds were identified as follows: isoliquiritigenin ( 4 ) [ 18 ], glycyrol ( 5 ) [ 19 ], 6,8-diprenylgenistein ( 6 ) [ 20 ], lupiwighteone ( 7 ) [ 21 ], gancaonin L( 8 ) [ 22 ], luteone ( 9 ) [ 23 ], 2,3-dehydrokievitone ( 10 ) [ 24 ], 7-O-methylluteone ( 11 ) [ 25 ], isochandalone ( 12 ) [ 26 ], isoderrone ( 13 ) [ 27 ], licoisoflavone B ( 14 ) [ 28 ], methyleriosemaone D ( 15 ) [ 29 ], euchestraflavanone A ( 16 ) [ 30 ], liquiritigenin ( 17 ) [ 21 ], glabrol ( 18 ) [ 31 ], dihydroformononetin ( 19 ) [ 32 ], licoisoflavanone C ( 20 ) [ 17 ], and 1-(4-ethenylphenyl)enthanone ( 21 ).…”

Section: Resultsmentioning

confidence: 99%

Three New Compounds, Licopyranol A–C, Together with Eighteen Known Compounds Isolated from Glycyrrhiza glabra L. and Their Antitumor Activities

et al. 2022

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Glycyrrhiza glabra L., known as licorice, is one of the most famous herbs in the world. In this study, we investigated the phytochemical and antitumor activities of G. glabra, especially its anti-colorectal cancer activities. G. glabra was extracted with 70% methanol, and the ethyl acetate layer was separated by silica gel, ODS, LH-20 column chromatography, and semi-preparative HPLC to obtain the compounds. The structures were determined by NMR and MS methods. Three new compounds named licopyranol A-C (1–3), and eighteen known compounds (4–21) were isolated. Compounds with an isoprenyl group or dimethylpyran ring showed better antitumor activities. Licopyranol A (1) and glycyrol (5) both inhibited the proliferation, reduced clone formation and promoted apoptosis of RKO cells. The Western blotting assays showed that glycyrol significantly reduced the expression of E-cadherin, β-catenin, c-Myc, and GSK-3β proteins in RKO cells, suggesting that glycyrol may inhibit the growth of colorectal cancer RKO cells via the Wnt/β-catenin signaling pathway.

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