Abstract
Phytochemical investigation of the stem bark of Diospyros longiflora yielded longiflorol (1), a new bergenin α-d-apioside, together with bergenin (2) and five known compounds: lupeol (S1), betulin (S2), betulinic acid (S3), stigmasterol (S4) and stigmasterol glucoside (S5). Their structures were determined by one-dimensional (1D) and 2D nuclear magnetic resonance experiments along with electrospray ionization high-resolution mass spectrometry and extended density-functional theory calculations of chiroptical properties. Longiflorol (1) and bergenin (2) were evaluated for their DPPH (2,2-diphenyl-1-picrylhydrazyl) antioxidant activity, with the crude extract for comparison and ascorbic acid as standard. The results showed that the extract and 2 had good antioxidant activity, whereas 1 showed only moderate activity at high concentration (>2 mg mL−1).
Acknowledgments
We thank Dr. H. Frauendorf and Dr. M. John for the mass spectroscopy and NMR measurements, respectively. We are very thankful to Dr. Sean Ohlinger and Dr. Warren Hehre (Wavefunction Inc., Irvine, CA, USA) for their continuous help in using Spartan.
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The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2018-0019).
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