Polyprenylated polycyclic acylphloroglucinol: Angiogenesis inhibitor from Garcinia multiflora

Lin-Yang Cheng; Chun-Lin Chen; Yueh-Hsiung Kuo; Tsung-Hsien Chang; I-Wei Lin; Shih-Wei Wang; Mei-Ing Chung; Jih-Jung Chen

doi:10.1016/j.bmcl.2018.04.006

Polyprenylated polycyclic acylphloroglucinol: Angiogenesis inhibitor from Garcinia multiflora

Bioorg Med Chem Lett. 2018 Jun 1;28(10):1860-1863. doi: 10.1016/j.bmcl.2018.04.006. Epub 2018 Apr 6.

Authors

Lin-Yang Cheng¹, Chun-Lin Chen², Yueh-Hsiung Kuo³, Tsung-Hsien Chang⁴, I-Wei Lin⁵, Shih-Wei Wang⁵, Mei-Ing Chung¹, Jih-Jung Chen⁶

Affiliations

¹ School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
² Department of Biological Sciences, National Sun Yat-Sen University, Kaohsiung 804, Taiwan.
³ Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, China Medical University, Taichung 404, Taiwan; Department of Biotechnology, Asia University, Taichung 413, Taiwan.
⁴ Department of Medical Education and Research, Kaohsiung Veterans General Hospital, Kaohsiung 813, Taiwan.
⁵ Department of Medicine, Mackay Medical College, New Taipei City 252, Taiwan.
⁶ Faculty of Pharmacy, School of Pharmaceutical Sciences, National Yang-Ming University, Taipei 112, Taiwan; Department of Medical Research, China Medical University Hospital, Taichung 404, Taiwan. Electronic address: chenjj@ym.edu.tw.

PMID: 29655982
DOI: 10.1016/j.bmcl.2018.04.006

Abstract

A new polyprenylated polycyclic acylphloroglucinol, garcimultiflorone K (1), has been isolated from the stems of Garcinia multiflora, together with two known compounds, garcimultiflorone A (2) and garcimultiflorone B (3). The structure of new compound 1 was determined through spectroscopic methods including 1D and 2D NMR and MS analyses. The anti-angiogenic and anti-cancer effects of compounds 1-3 were evaluated in human endothelial progenitor cells (EPCs) and cancer cells. Of these, garcimultiflorone K (1) displayed the most potent anti-angiogenic property by suppressing cell growth and tube formation of EPCs. Compound 1 also exhibited growth-inhibitory activities against human hepatocellular carcinoma cell line SK-Hep-1 and hormone refractory prostate cancer cell line PC-3 with GI₅₀ values of 4.3 ± 1.6 and 6.6 ± 0.4 μM, respectively.

Keywords: Angiogenesis inhibitor; Garcimultiflorone K; Garcinia multiflora; Guttiferae; Polyprenylated polycyclic acylphloroglucinol.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Angiogenesis Inhibitors / chemistry*
Angiogenesis Inhibitors / isolation & purification
Angiogenesis Inhibitors / pharmacology
Antineoplastic Agents, Phytogenic / chemistry*
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology
Cell Line
Cell Proliferation / drug effects
Garcinia / chemistry*
Garcinia / metabolism
Humans
Magnetic Resonance Spectroscopy
Molecular Conformation
Phloroglucinol / chemistry*
Phloroglucinol / isolation & purification
Phloroglucinol / pharmacology

Substances

Angiogenesis Inhibitors
Antineoplastic Agents, Phytogenic
garcimultiflorone K
Phloroglucinol