Dihydrochalcones and Diterpenoids from Pteris ensiformis and Their Bioactivities

• Published in: Molecules (Basel, Switzerland) Vol. 22; no. 9; p. 1413
• Main Authors: Shi, Yu-Sheng, Zhang, Yan, Hu, Wen-Zhong, Zhang, Xiu-Fu, Fu, Xin, Lv, Xia
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 25.08.2017; MDPI
• Subjects: Animals; Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Arthritis; Cell Line, Tumor; Chalcones - chemistry; Chalcones - isolation & purification; Chalcones - pharmacology; Chromatography, High Pressure Liquid; Circular Dichroism; cytotoxic activity; Cytotoxicity; dihydrochalcone; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; diterpenoid; Drug dosages; Edema; Ethanol; Flavonoids; Humans; inhibitory activity on nitric oxide production; Laboratories; Macrophage Activation - drug effects; Mice; Nitric Oxide - antagonists & inhibitors; Nitric Oxide - biosynthesis; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Pteris - chemistry; Pteris ensiformis; Short Note; Spectrum analysis; Pteris ensiformis; inhibitory activity on nitric oxide production; cytotoxic activity; diterpenoid; dihydrochalcone
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22091413

Two new dihydrochalcone enantiomers (+)-1 and (−)-1, along with eight known compounds 3–10, were obtained from Pteris ensiformis. The planar structures were determined on the basis of extensive 1D and 2DNMR and HRESIMS. The resolution of (+)-1 and (−)-1 was achieved by chiral HPLC analysis. The absolute configurations of (+)-1 and (−)-1 were established by the bulkiness rule using Rh2(O2CCF3)4-induced circular dichroism (ICD) method. Compounds (+)-1, (−)-1, 8, 9 and 10 exhibited the inhibitory assay of NO production in mouse macrophages stimulated by LPS, with IC50 values of 2.0, 2.5, 8.0, 9.5 and 5.6 μM, respectively. Otherwise, compound 10 showed moderate cytotoxic activity against HCT-116, HepG-2 and BGC-823 cell lines with IC50 values of 3.0, 10.5 and 6.3 μM, respectively.