Stilbenes in the roots of Carex acuta and Carex lepidocarpa were studied. Root samples were extracted with 100% methanol and analyzed by HPLC and LC-MS. In this way, trans-resveratrol dimers (m/z 455 Da [M + H]+), trimers (m/z 681 Da [M + H]+) and tetramers (m/z 907 Da [M + H]+) were identified in the extracts. Using LC-NMR in stop-flow mode, pallidol and trans-ε-viniferin as dimers were identified. After the separation of individual peaks and their measurement by 1H NMR, cis and trans-miyabenol A as a tetramer and cis-miyabenol C as a trimer were identified. In the case of miyabenol A, it is a chromatographically inseparable mixture of cis and trans isomers in the ratio of 2:3 according to 1H NMR measurement. In the case of cis-miyabenol C, the Z-trans-trans-miyabenol C configuration was confirmed. The remaining unidentified peak with a practically identical UV-VIS spectrum to that of cis-miyabenol C is most likely another isomer of miyabenol C.

Department of Analytical Chemistry University of Chemistry and Technology Technická 5 166 28 Prague Czech Republic

Department of Environmental Engineering Institute of Chemical Process Fundamentals Czech Academy of Sciences Rozvojová 2 135 165 02 Prague Czech Republic

Department of Experimental and Functional Morphology Institute of Botany Czech Academy of Sciences Dukelská 135 379 01 Třeboň Czech Republic

Laboratory of Metabolomics and Isotope Analyses Global Change Research Institute Czech Academy of Sciences Bělidla 986 4a 603 00 Brno Czech Republic

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Koopman J. Carex Europaea. The Genus Carex L. (Cyperaceae) in Europe, 1: Accepted Names, Hybrids, Synonyms, Distribution, Chromosome Numbers. Margraf Publishers; Weikersheim, Germany: 2011.

Schweingruber F.H., Kučerová A., Adamec L., Doležal J. Anatomic Atlas of Aquatic and Wetland Plant Stems. Springer; Berlin, Germany: 2020.

Hedrén M. Patterns of allozyme and morphological differentiation in the Carex flava complex (Cyperaceae) in Fennoscandia. Nord. J. Bot. 2002;22:257–301. doi: 10.1111/j.1756-1051.2002.tb01373.x. DOI

Blackstock N. Ph.D. Thesis. University of Lancaster; Lancaster, UK: 2007. A reassessment of Yellow Sedges—Carex flava agg. (Cyperaceae) in the British Isles.

de Moraes K.R., Souza A.T., Muška M., Hladík M., Čtvrtlíková M., Draštík V., Kolařík T., Kučerová A., Krolová M., Sajdlová Z., et al. Artificial floating islands: A promising tool to support juvenile fish in lacustrine systems. Hydrobiologia. 2023;850:1969–1984. doi: 10.1007/s10750-023-05204-8. DOI

Harris T., Klimeš A., Martínková J., Klimešová J. Herbs are not just small plants: What biomass allocation to rhizomes tells us about differences between trees and herbs. Am. J. Bot. 2023;110:e16202. doi: 10.1002/ajb2.16202. PubMed DOI

González-Sarrías A., Gromek S., Niesen D., Seeram N.P., Henry G.E. Resveratrol oligomers isolated from Carex species inhibit growth of human colon tumorigenic cells mediated by cell cycle arrest. J. Agric. Food Chem. 2011;59:8632–8638. doi: 10.1021/jf201561e. PubMed DOI

Hu J., Lin T., Gao Y., Xu J., Jiang C., Wang G., Bu G., Xu H., Chen H., Zhang Y. The resveratrol trimer miyabenol C inhibits β-secretase activity and β-amyloid generation. PLoS ONE. 2015;10:e0115973. doi: 10.1371/journal.pone.0115973. PubMed DOI PMC

Wang C., Ye X., Ding C., Zhou M., Li W., Wang Y., You Q., Zong S., Peng Q., Duanmu D., et al. Two resveratrol oligomers inhibit cathepsin L activity to suppress SARS-CoV-2 entry. J. Agric. Food Chem. 2023;71:5535–5546. doi: 10.1021/acs.jafc.2c07811. PubMed DOI

Arraki K., Totoson P., Decendit A., Badoc A., Zedet A., Jolibois J., Pudlo M., Demougeot C., Girard-Thernier C. Cyperaceae species are potential sources of natural mammalian arginase inhibitors with positive effects on vascular function. J. Nat. Prod. 2017;80:2432–2438. doi: 10.1021/acs.jnatprod.7b00197. PubMed DOI

Arraki K., Richard T., Badoc A., Pédrot E., Bisson J., Waffo-Téguo P., Mahjoub A., Mérillon J.M., Decendit A. Isolation, characterization and quantification of stilbenes from some Carex species. Rec. Nat. Prod. 2013;7:281–291.

Senda N., Kubota Y., Hoshino T., Nozaki H., Hayashi H., Nakayama M. Mass spectra of some stilbene oligomers from Carex species. J. Mass Spectrom. Soc. Jpn. 1995;43:45–51. doi: 10.5702/massspec.43.45. DOI

Fiorentino A., Ricci A., D’Abrosca B., Pacifico S., Golino A., Letizia M., Picolella S., Monaco P. Potential food additives from Carex distachya roots: Identification and in vitro antioxidant properties. J. Agric. Food Chem. 2008;56:8218–8225. doi: 10.1021/jf801603s. PubMed DOI

Suzuki K., Shimizu T., Kawabata J., Mizutani J. New 3,5,4′-trihydroxystilbene (resveratrol) oligomers from Carex fedia Nees var. miyabei (Franchet) T. Koyama (Cyperaceae) Agric. Biol. Chem. 1987;51:1003–1008.

Li L., Henry G.E., Seerman N.P. Identification and bioactivities of resveratrol oligomers and flavonoids from Carex folliculata seeds. J. Agric. Food Chem. 2009;57:7282–7287. doi: 10.1021/jf901716j. PubMed DOI

Seo H., Kim M., Kim S., Mahmud H.A., Islam M.I., Nam K.W., Cho M.L., Kwon H.-S., Song H.Y. In vitro activity of alpha-viniferin isolated from the roots of Carex humulis against Mycobacterium tuberculosis. Pulm. Pharmacol. Ther. 2017;46:41–47. doi: 10.1016/j.pupt.2017.08.003. PubMed DOI

Kawabata J., Ichikawa S., Kurihara H., Mizunati J. Kobophenol-A, a unique tetrastilbene from Carex kobomugi Ohwi (Cyperaceae) Tetrahedron Lett. 1989;30:3785–3788. doi: 10.1016/S0040-4039(01)80655-9. DOI

Meng Y., Bourne P.C., Whiting P., Šik V., Dinan L. Identification and ecdysteroid antagonist activity of three oligostilbenes from the seeds of Carex pendula (Cyperaceae) Phytochemistry. 2001;57:393–400. doi: 10.1016/S0031-9422(01)00061-9. PubMed DOI

Kurihara H., Kawabata J., Ichikawa S., Mizutani J. (-)-ɛ-viniferin and related oligostilbenes from Carex pumita Thunb. (Cyperaceae) Agric. Biol. Chem. 1990;54:1097–1099.

Niesen D.B., Ma H., Yuan T., Bach A.C., Henry G.E., Seeram N.P. Phenolic constituents of Carex vulpinoidea seeds and their tyrosinase inhibitory activities. Nat. Prod. Commun. 2015;10:491–493. doi: 10.1177/1934578X1501000328. PubMed DOI

Dávid C.Z., Hohmann J., Vasas A. Chemistry and pharmacology of Cyperaceae stilbenoids: A review. Molecules. 2021;26:2794. doi: 10.3390/molecules26092794. PubMed DOI PMC

Gajbhiye R., Sarma S.S., Kumar D., Singh S. The treasure trove of the genus Carex: A phytochemical and pharmacological review. Health Sci. Rev. 2024;10:100151. doi: 10.1016/j.hsr.2024.100151. DOI

Biais B., Krisa S., Cluzet S., Costa G.D., Waffo-Teguo P., Mérillon J.M., Richard T. Antioxidant and cytoprotective activities of grapevine stilbenes. J. Agric. Food Chem. 2017;65:4952–4960. doi: 10.1021/acs.jafc.7b01254. PubMed DOI

Soural I., Vrchotová N., Tříska J., Balík J., Horník Š., Cuřínová P., Sýkora J. Various extraction methods for obtaining stilbenes from grape cane of Vitis vinifera L. Molecules. 2015;20:6093–6112. doi: 10.3390/molecules20046093. PubMed DOI PMC

Mattivi F., Vrhovsek U., Malacarne G., Masuero D., Zulini L., Stefanini M., Moser C., Velasco R., Guella G. Profiling of resveratrol oligomers, important stress metabolites, accumulating in the leaves of hybrid Vitis vinifera (Merzling × Toroldego) genotypes infected with Plasmopara viticola. J. Agric. Food Chem. 2011;59:5364–5375. doi: 10.1021/jf200771y. PubMed DOI