Abstract
Six new compounds, hyperpatulones A–F (1–6), along with ten additional known related derivatives (7–16), were isolated from Hypericum patulum (Guttiferae). Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D and 2D NMR), X-ray crystallography, electronic circular dichroism (ECD) spectroscopy and Rh2(OCOCF3)4-induced ECD. All compounds were tested for their cytotoxic activities on human HepG-2, HeLa, MCF-7, and A549 cell lines via 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Compound 5 exhibited significant cytotoxicities against HepG-2, HeLa and A549 cell lines with IC50 values of 9.52 ± 0.27, 11.87 ± 0.22 and 12.63 ± 0.12 μM, respectively.
Highlights
Hyperpatulones A–F [1,2,3,4,5,6], along with ten additional known related derivatives [7,8,9,10,11,12,13,14,15,16], were isolated from Hypericum patulum (Guttiferae). Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D and 2D NMR), X-ray crystallography, electronic circular dichroism (ECD) spectroscopy and Rh2(OCOCF3)4-induced ECD
We report the isolation and structural elucidation of six new polyprenylated acylphloroglucinols (PPAPs) [1,2,3,4,5,6] (Fig. 1), together with ten known aInstitute of Traditional Chinese Medicine & Natural Products, Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou 510632, People's Republic of China
The 95% EtOH extract of Hypericum patulum was subjected to liquid–liquid fractionation to afford a petroleum ether (PE)soluble fraction and an ethyl acetate (EtOAc)-soluble fraction
Summary
Hypericum patulum (Guttiferae) is well known as “Jinsimei” in China, and is distributed mainly in southwest China, such as Guizhou, Sichuan and Yunnan Provinces.1 The herbs of H. patulum are used as a traditional medicine to clear heat, cool blood, relax tendons and activate collaterals, and to treat gonorrhea, hepatitis, colds, etc.2–6 Modern pharmacological investigations demonstrated that the plants of the genus Hypericum possessed anti-depression,7–11 anti-tumor,12–18 antibacterial,19,20 anti-viral,17,18,21–23 and liver protective activities.24 Previous phytochemical studies on these plants showed that derivatives of polycyclic polyprenylated acylphloroglucinols (PPAPs), which possessed a highly oxygenated bicyclo[3.3.1] nonane-2,4,9-trione or other related core decorated with C5H9 or C10H17 (prenyl or geranyl) side chains, were the main bioactive components.7,13–19,21,24,25In this paper, we report the isolation and structural elucidation of six new PPAPs [1,2,3,4,5,6] (Fig. 1), together with ten known.
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