Ternstroenols A – E: Undescribed pentacyclic triterpenoids from the Australian rainforest plant Ternstroemia cherryi. (August 2020)

• Record Type: Journal Article
• Authors: Singh, Ahilya; Cullen, Jason K.; Bruce, Zara C.; Reddell, Paul; Münch, Gerald; Raju, Ritesh
• Is Part Of: Phytochemistry. Volume 176(2020)
• Publication Date: 2020-08
• Subjects: Ternstroemia cherryi -- Pentaphylacaceae -- Anti-inflammatory -- Triterpenoid -- Ternstroenols; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2020.112426
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: Chromatographic separation of the extracts of the Australian rainforest plant Ternstroemia cherryi led to the isolation of five undescribed barrigenol-like triterpenoids, ternstroenols A – E, from the fruits and three known ones from the leaves. Ternstroenols A – E represent a new form of structural diversity, being the first in its kind to incorporate a trans - 2, 4, 6- decatrienoyl moiety at C-22. The structures of the ternstroenols were assigned by detailed spectroscopic analysis, degradation and chemical derivatization. All compounds exhibited potent anti-inflammatory activity in LPS and IFN- γ activated RAW 264.7 macrophages, with IC50 values as low as 0.7 μM. Despite the remarkable potency, high levels of unwanted cell growth inhibition was also observed, which prompted their cytotoxic evaluation in U87/U251 human glioblastoma cell lines. Graphical abstract: Image 1 Highlights: Five undescribed barrigenol like triterpenoids isolated from T. Cherryi. Ternstroenols A - E exhibited potent anti-inflammatory activity. The ternstroenols inhibited the growth of glioblastoma cell lines.