title: Synthesis and bioactivity of tripolinolate A from Tripolium vulgare and its analogs.
abstract: A new coniferol derivative, named as tripolinolate A (1), and 11 known compounds (2-12) were isolated from whole plants of Tripolium vulgare Nees. The structure of this new compound was determined as 4-(2S-methylbutyryl)-9-acetyl-coniferol based on its NMR and HRESIMS spectral analyses. A simple and efficient method was designed to prepare tripolinolate A and its 19 analogs including nine new chemical entities for bioactive assay. Tripolinolate A and its analog 4,9-diacetyl-coniferol were found to be the two most active compounds that significantly inhibited the proliferation of different cancer cell lines with IC50 values ranging from 0.36 to 12.9μM and induced apoptosis in tumor cells. Structure-activity relationship analysis suggested that the molecular size of acyl moieties at C-4 and C-9 position might have an effect on the activity of this type of coniferol derivatives.
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Lu
authors.initials: L
authors.lastname: Chen
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Ying
authors.initials: Y
authors.lastname: Liang
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Tengfei
authors.initials: T
authors.lastname: Song
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Komal
authors.initials: K
authors.lastname: Anjum
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Wenling
authors.initials: W
authors.lastname: Wang
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Siran
authors.initials: S
authors.lastname: Yu
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China.
authors.forename: Haocai
authors.initials: H
authors.lastname: Huang
authors.affiliation: College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China. Electronic address: xylian@zju.edu.cn.
authors.forename: Xiao-Yuan
authors.initials: XY
authors.lastname: Lian
authors.affiliation: Ocean College, Zhejiang University, Hangzhou 310058, China. Electronic address: zzhang88@zju.edu.cn.
authors.forename: Zhizhen
authors.initials: Z
authors.lastname: Zhang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D019659:Asteraceae / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D005910:Glioma / Q000188:drug therapy / Q000473:pathology; D006801:Humans; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D000972:Antineoplastic Agents, Phytogenic
keywords: Apoptosis; Compositae; Inhibition of cancer cell proliferation; Structure–activity relationship; Synthesis of tripolinolate A and analogs; Tripolinolate A; Tripolium vulgare