title: Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues.
abstract: The marine alkaloids, longamide B (1), longamide B methyl ester (2), hanishin (3), and a series of non-naturally occurring analogues were synthesized in an efficient manner from inexpensive commercially available dl-aspartic acid dimethyl ester. The cytotoxicities of these natural products (1-3) and their analogues (9-15) were evaluated against human lung adenocarcinoma (A549) and human prostate cancer (PC3) cells. This is the first evaluation of the cytotoxicities of these alkaloids in these cancer cell lines and it revealed that analogue 15 had comparable cytotoxic activity to its natural parent compound, (±)-hanishin (3). This study provides useful information for further structural modification of these alkaloids in order to develop novel antitumor agents.
authors.affiliation: Institute of Natural Medicinal Chemistry & Green Chemistry, Department of Pharmaceutical Engineering, School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China.
authors.forename: Deng-Gao
authors.initials: DG
authors.lastname: Zhao
authors.affiliation: Institute of Natural Medicinal Chemistry & Green Chemistry, Department of Pharmaceutical Engineering, School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China.
authors.forename: Yan-Yan
authors.initials: YY
authors.lastname: Ma
authors.affiliation: Institute of Natural Medicinal Chemistry & Green Chemistry, Department of Pharmaceutical Engineering, School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China.
authors.forename: Wei
authors.initials: W
authors.lastname: Peng
authors.affiliation: Institute of Natural Medicinal Chemistry & Green Chemistry, Department of Pharmaceutical Engineering, School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China.
authors.forename: Ai-Yu
authors.initials: AY
authors.lastname: Zhou
authors.affiliation: School of Chemistry & Environmental Engineering, Wuyi University, Jiangmen 529020, People's Republic of China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Infinitus (China) Company Ltd, People's Republic of China.
authors.forename: Liugang
authors.initials: L
authors.lastname: Ding
authors.affiliation: Institute of Natural Medicinal Chemistry & Green Chemistry, Department of Pharmaceutical Engineering, School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China. Electronic address: zhiyundu@foxmail.com.
authors.forename: Zhiyun
authors.initials: Z
authors.lastname: Du
authors.affiliation: Institute of Natural Medicinal Chemistry & Green Chemistry, Department of Pharmaceutical Engineering, School of Light Industry and Chemical Engineering, Guangdong University of Technology, Guangzhou 510006, People's Republic of China; School of Chemistry & Environmental Engineering, Wuyi University, Jiangmen 529020, People's Republic of China. Electronic address: kunzhang@gdut.edu.cn.
authors.forename: Kun
authors.initials: K
authors.lastname: Zhang
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D011758:Pyrroles; C511000:hanishin; C511002:longamide B; C511001:longamide B methyl ester
keywords: Cytotoxic activity; Hanishin; Longamide B; Longamide B methyl ester; Total synthesis