Hyperpatulones A-F, polycyclic polyprenylated acylphloroglucinols from Hypericum patulum and their cytotoxic activities

Zhong-Nan Wu; Qian-Wen Niu; Yu-Bo Zhang; Ding Luo; Qing-Guo Li; Ying-Ying Li; Guang-Kai Kuang; Li-Jun He; Guo-Cai Wang; Yao-Lan Li

doi:10.1039/c9ra00277d

Hyperpatulones A-F, polycyclic polyprenylated acylphloroglucinols from Hypericum patulum and their cytotoxic activities

RSC Adv. 2019 Mar 12;9(14):7961-7966. doi: 10.1039/c9ra00277d. eCollection 2019 Mar 6.

Authors

Zhong-Nan Wu¹, Qian-Wen Niu¹, Yu-Bo Zhang^{1

2}, Ding Luo¹, Qing-Guo Li³, Ying-Ying Li¹, Guang-Kai Kuang¹, Li-Jun He¹, Guo-Cai Wang^{1

2}, Yao-Lan Li¹

Affiliations

¹ Institute 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 twangguocai@jnu.edu.cn tliyl@jnu.edu.cn.
² Integrated Chinese and Western Medicine Postdoctoral Research Station, Jinan University Guangzhou 510632 People's Republic of China.
³ School of Pharmaceutical Sciences, Guangzhou University of Chinese Medicine Guangzhou 510006 China.

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.