Hypersampones A–C, Three Nor-Polycyclic Polyprenylated Acylphloroglucinols with Lipid-Lowering Activity from Hypericum sampsonii

Abstract

Hypersampones A−C (1−3), three unprecedented nor-polycyclic polyprenylated acylphloroglucinols (PPAPs), were isolated from Hypericum sampsonii. These compounds represent the first nor-PPAPs with an unexpected tetracyclic 6/5/5/6 ring system. Their structures were assigned through the analysis of detailed spectroscopic data, X-ray crystallography, and electronic circular dichroism calculations. Compound 1 significantly inhibited the accumulation of lipid in an oleic acid-treated HepG2 cell model by suppressing the protein expression of FAS and ACACA at 5 μM.

Three rare nor-sesquiterpenoids with lipid-lowering activity from Belamcanda chinensis

“…Cell viability (HepG2 cells) was tested by using the MTT assay. 29 The HepG2 cells were seeded in 96-well plates (1 × 10 4 cells per well) for 12 h at 37 °C and treated with oleic acid at 0.5 mM concentration for 24 h; then, compounds 1–4 (5, 10, 20 μM) were added to the cell culture medium for 24 h. Colorimetry was performed with DMEM (100 μL) containing MTT (5 mg mL −1 ) at 37 °C for 4 h. The optical density was measured at 490 nm using a microplate reader. Then, 150 μL DMSO was added and kept for 10 min, and the complete medium was used as the blank control.…”

“…HepG2 cells in the logarithmic growth phase were seeded in 6-well plates at a density of 3 × 10 5 cells per mL. 29 After 12 h, the cells in the 6-well culture plates were washed with PBS, and the medium containing 0.5 mM oleic acid–bovine serum albumin (OA-BSA) complex was added in the presence or absence of compounds and the positive drug (atorvastatin, 10 μM) for 24 h. The medium with only BSA was selected as the control. The triglyceride (TG) level was determined according to the instructions in the kit.…”

Hyperpatone A, a polycyclic polyprenylated acylphloroglucinol with a rare 8/6/5/6/5 pentacyclic skeleton from Hypericum patulum

“…26,27 Further oxidation of ii might give the common intermediate iii, which could undergo an intermolecular dehydration reaction between two hydroxyl groups to obtain compound 2. Baeyer-Villiger oxidation and nucleophilic reaction might happen for iii to give intermediate iv, 28,29 which could be followed by esterolysis, decarboxylation, and epoxidation to obtain the key intermediate vi. 30,31 Further intermolecular cyclization reaction might occur to give intermediate vii.…”

Discovery from Hypericum elatoides and synthesis of hyperelanitriles as α-aminopropionitrile-containing polycyclic polyprenylated acylphloroglucinols

“…PPAPs found mainly in plants of the genera Hypericum and Garcinia are a special class of fascinating natural products composed of a highly oxygenated acylphloroglucinol-derived cores and dense prenyl or geranyl side chains 1 , 6 . According to the different structural features, the various PPAPs are typically divided into three groups: the bicyclic polyprenylated acylphloroglucinols (BPAPs) with major bicyclo[3.3.1]nonane-2,4,9-trione core, the caged PPAPs with adamantane and homoadamantane scaffolds, spirocyclic PPAPs, and other complicated PPAPs 1 , 7 – 9 . Up to date, more than 1100 PPAPs have been characterized 10 , 11 .…”