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Gentianelloids A and B: Immunosuppressive 10,11-<i>seco</i>-Gentianellane Sesterterpenoids from the Traditional Uighur Medicine <i>Gentianella turkestanorum</i>

Kai Guo, Xin Liu, Tingting Zhou, Yanchun Liu, Yan Liu, Qiu-Mei Shi, Xiao‐Nian Li, Sheng‐Hong Li

2020The Journal of Organic Chemistry28 citationsDOI

Abstract

Two sesterterpenoids, possessing an unusual 10,11-seco-gentianellane skeleton, gentianelloids A and B, were isolated from a traditional Uighur medicine Gentianella turkestanorum. Through extensive spectroscopic analysis and single-crystal X-ray diffraction, their structures including absolute configurations were unambiguously determined. A plausible biosynthetic pathway for the two compounds was proposed. Both compounds showed remarkable immunosuppressive activity, including inhibition of the proliferation, activation, and cytokine IFN-γ production of T cells. The findings suggested that sesterterpenoids could contribute positively to the therapeutic effects of this popular traditional Uighur medicine.

Topics & Concepts

StereochemistryTraditional medicineChemistryPharmacologyMedicineNatural product bioactivities and synthesisPhytochemistry and Biological ActivitiesPlant biochemistry and biosynthesis