Ternstroenols A – E: Undescribed pentacyclic triterpenoids from the Australian rainforest plant Ternstroemia cherryi

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...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2020-08, Vol.176, p.112426-112426, Article 112426
Main Authors: Singh, Ahilya, Cullen, Jason K., Bruce, Zara C., Reddell, Paul, Münch, Gerald, Raju, Ritesh
Format: Article
Language:English
Subjects:
Anti-inflammatory
Pentaphylacaceae
Ternstroemia cherryi
Ternstroenols
Triterpenoid
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Summary: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. [Display omitted] •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.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2020.112426