Phytocannabinoid-like meroterpenoids from twigs and leaves of Rhododendron spinuliferum

Phytochemistry. 2024 Aug 7:114241. doi: 10.1016/j.phytochem.2024.114241. Online ahead of print.

ABSTRACT

Six pairs of previously undescribed enantiomeric phytocannabinoid-like meroterpenoids, (±)-spinulinoids A‒F, and two naturally occurring compounds, (+)-rhododaurichromanic acid A and (E)-4-((3,7-dimethylocta-2,6-dien-1-yl)oxy)benzoic acid, together with one known congener, (‒)-rhododaurichromanic acid A, were obtained from the twigs and leaves of Rhododendron spinuliferum. Their structures were established by their extensive spectral data (NMR and HRESIMS), ECD calculations, and single-crystal X-ray diffraction data. Spinulinoids A and B are the unprecedented phytocannabinoid-like meroterpenoids constructed by the resorcinol moiety and a β-bisabolene unit, whereas spinulinoid C represents a rare adduct of quinone and β-bisabolene with a tricyclic 6/6/6 ring system.

PMID:39122160 | DOI:10.1016/j.phytochem.2024.114241