Identification and structural elucidation of anti-inflammatory stilbene oligomers and flavonoids from the subaerial parts of Scirpoides holoschoenus

The plant Scirpoides holoschoenus (Linnaeus) Soják (syn. Scirpus holoschoenus) (Cyperaceae) is native to Mediterranean and Asian countries and spreads to the western Himalaya. The subaerial plant material is used at the shores of the Danube delta as a traditional remedy to treat liver disorders [1], [2]. Up to now, the phytochemistry and bioactivity of S. holoschoenus has been poorly investigated [3], [4]. Phytochemical investigations of dichloromethane and methanol extracts of roots and rhizomes of S. holoschoenus afforded 19 stilbenes, six flavonoids, six ferulic acid derivatives and four diterpenes, which have not been reported as constituents of this species. Among these constituents, ten derivatives represent previously unreported natural products. Structure elucidation was performed by HRESI-MS, NMR, GC-MS, and ECD data evaluation. The stilbene dimer trans-scirpusin B and trimer cyperusphenol B showed promising inhibitory activities of NO production in LPS-stimulated J774A.1 murine macrophages in a concentration-dependent manner (IC₅₀ < 15 µM). Time-course experiments (3 – 20 h) in LPS-stimulated RAW 264.7 and THP-1 macrophages identified diprenylated flavonoids (euchestraflavanone A, gancaonin E and 2R-macarangaflavanone B) as highly active anti-inflammatory constituents. They attenuated the transcription levels of proinflammatory cytokines IL-1β and IL-6, measured by RT-qPCR, ELISA and Western blot analysis at concentrations of 0.1 – 5 µg/ml. The data obtained are the first results confirming the anti-inflammatory potential of S. holoschoenus and rationalize the traditional use of this plant to treat inflammation related disorders in the Danube delta.

• References

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Publication History

Article published online:
12 December 2022