2. Academic Validation
  3. Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues

Total synthesis and cytotoxic activities of longamide B, longamide B methyl ester, hanishin, and their analogues

  • Bioorg Med Chem Lett. 2016 Jan 1;26(1):6-8. doi: 10.1016/j.bmcl.2015.11.069.
Deng-Gao Zhao 1,  Yan-Yan Ma 1,  Wei Peng 1,  Ai-Yu Zhou 1,  Yu Zhang 2,  Liugang Ding 3,  Zhiyun Du 4,  Kun Zhang 5
Affiliations

Affiliations

  • 1 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.
  • 2 School of Chemistry & Environmental Engineering, Wuyi University, Jiangmen 529020, People's Republic of China.
  • 3 Infinitus (China) Company Ltd, People's Republic of China.
  • 4 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.
  • 5 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.
PMID: 26615890 DOI: 10.1016/j.bmcl.2015.11.069
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.

Keywords

Cytotoxic activity; Hanishin; Longamide B; Longamide B methyl ester; Total synthesis.

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