title: Seven New Tetrahydroanthraquinones from the Root of Prismatomeris connata and Their Cytotoxicity against Lung Tumor Cell Growth.
abstract: The root of Prismatomeris connata has been used in China for centuries as the medicinal herb "Huang Gen" (HG), but its phytochemicals or active ingredients are not well understood. In this study, we performed chemical analysis of the ethyl acetate fraction of a HG ethanol extract. We thus isolated seven new tetrahydroanthraquinones, prisconnatanones C-I (compounds 1-7) from the root of P. connata and identified their structures using spectroscopic analyses. Their absolute configurations were established by both modified Mosher's and Mo₂OAc₄ methods, and ORD techniques. Their cytotoxicity was tested in a panel of human lung tumor cells (H1229, HTB179, A549 and H520 cell lines). Prisconnatanone I (7) showed the highest activity, with an IC50 value ranging from 2.7 µM to 3.9 µM in the suppression of tumor cell growth, and the others with chelated phenolic hydroxyls exhibited relatively lower activity (IC50: 8-20 µM). In conclusion, these data suggest that some of the natural tetrahydroanthraquinones in HG are bioactive, and hydroxylation at C-1 significantly increases the cytotoxicity of these compounds against lung tumor cell growth.
authors.affiliation: Key Laboratory of South Subtropical Plant Diversity, Fairy Lake Botanical Garden, Shenzhen &amp; Chinese Academy of Sciences, Shenzhen 518004, China. cxwang2015@hotmail.com.|School of Life Sciences, Anhui Normal University, Wuhu 241000, China. cxwang2015@hotmail.com.
authors.forename: Chunxiang
authors.initials: C
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China. dingxiao@mail.kib.ac.cn.
authors.forename: Xiao
authors.initials: X
authors.lastname: Ding
authors.affiliation: Key Laboratory of South Subtropical Plant Diversity, Fairy Lake Botanical Garden, Shenzhen &amp; Chinese Academy of Sciences, Shenzhen 518004, China. fengshixiu@scbg.ac.cn.
authors.forename: Shi-Xiu
authors.initials: SX
authors.lastname: Feng
authors.affiliation: Department of Urologic Sciences, University of British Columbia, Vancouver, BC V6H 3Z6, Canada. qiunong@hotmail.com.
authors.forename: Qiunong
authors.initials: Q
authors.lastname: Guan
authors.affiliation: School of Life Sciences, Anhui Normal University, Wuhu 241000, China. pinghengxu@sina.com.
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Zhang
authors.affiliation: Department of Urologic Sciences, University of British Columbia, Vancouver, BC V6H 3Z6, Canada. caigan@mail.ubc.ca.
authors.forename: Caigan
authors.initials: C
authors.lastname: Du
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, China. diyt@mail.kib.ac.cn.
authors.forename: Ying-Tong
authors.initials: YT
authors.lastname: Di
authors.affiliation: Key Laboratory of South Subtropical Plant Diversity, Fairy Lake Botanical Garden, Shenzhen &amp; Chinese Academy of Sciences, Shenzhen 518004, China. taochen.mobg@gmail.com.
authors.forename: Tao
authors.initials: T
authors.lastname: Chen
mesh_terms: D000880:Anthraquinones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008175:Lung Neoplasms / Q000188:drug therapy*; D008958:Models, Molecular; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D019666:Rubiaceae / Q000737:chemistry*
chemical_list: D000880:Anthraquinones; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts
keywords: HPLC-NMR; Prismatomeris connata; anti-tumor activity; natural compound; prisconnatanones C–I; tetrahydroanthraquinones