New dihydro-β-agarofuran sesquiterpenes from Parnassia wightiana wall: isolation, identification and cytotoxicity against cancer cells

• Published in: International journal of molecular sciences 2014-06, Vol.15 (6), p.11111-11125
• Main Authors: Lv, Chao, Zheng, Zuo-Lue, Miao, Fang, Geng, Hui-Ling, Zhou, Le, Liu, La-Ping
• Format: Article
• Language: English
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - toxicity; Celastraceae - chemistry; Celastraceae - metabolism; Cell Line, Tumor; Cell Survival - drug effects; Crystallography, X-Ray; Drug Screening Assays, Antitumor; HL-60 Cells; Humans; MCF-7 Cells; Molecular Conformation; Plant Extracts - chemistry; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - toxicity; Structure-Activity Relationship
• ISSN: 1422-0067; 1422-0067
• DOI: 10.3390/ijms150611111

Five new (4-8) and three known (1-3) dihydro-β-agarofuran sesquiterpene polyesters were isolated from the whole plants of Parnassia wightiana. The structures of all compounds were elucidated through spectroscopic analysis including 2D-NMR and HR-MS. The absolute configuration of these compounds was established by X-ray diffraction analysis, comparison of NOESY spectra and biogenetic means. The cytotoxities of compounds 2-8 were evaluated in vitro against HL-60, SMMC-7721, A549, MCF-7 and SW480 cell lines. Compounds 5-7 exhibited the highest activities with IC₅₀ values of 11.8-30.1 μM in most cases. The SAR revealed that the introduction of hydroxyl group was able to significantly improve the activities of the compounds for most of the cell lines.