Additional alkaloids from Zoanthus vietnamensis with neuroprotective and anti-angiogenic effects

Shu-Rong Chen; Shih-Wei Wang; Yu-Chi Lin; Chen-Lin Yu; Juei-Yu Yen; Yih-Fung Chen; Yuan-Bin Cheng

doi:10.1016/j.bioorg.2021.104700

Additional alkaloids from Zoanthus vietnamensis with neuroprotective and anti-angiogenic effects

Bioorg Chem. 2021 Apr:109:104700. doi: 10.1016/j.bioorg.2021.104700. Epub 2021 Feb 8.

Authors

Shu-Rong Chen¹, Shih-Wei Wang², Yu-Chi Lin³, Chen-Lin Yu⁴, Juei-Yu Yen⁴, Yih-Fung Chen⁵, Yuan-Bin Cheng⁶

Affiliations

¹ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan.
² Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; Department of Medicine, Mackay Medical College, New Taipei City 25245, Taiwan; Institute of Biomedical Sciences, Mackay Medical College, New Taipei City 25245, Taiwan.
³ Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan.
⁴ Department of Medicine, Mackay Medical College, New Taipei City 25245, Taiwan.
⁵ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; Department of Fragrance and Cosmetic Science, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; Drug Development and Value Creation Research Center, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan. Electronic address: yihfungchen@kmu.edu.tw.
⁶ Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan; Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan; Department of Fragrance and Cosmetic Science, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, Taiwan. Electronic address: jmb@mail.nsysu.edu.tw.

PMID: 33607361
DOI: 10.1016/j.bioorg.2021.104700

Abstract

A chemical investigation of the zoantharian Zoanthus vietnamensis, collected off Taiwan, yielded eleven new alkaloids, 7α-hydroxykuroshine J (1), 18β-hydroxykuroshine J (2), 5α-hydroxyzoanthenamine (3), 5β-hydroxyzoanthenamine (4), 14α-hydroxyzoanthenamine (5), 30-hydroxyzoanthenamine (6), 11-dehydroxy-18-epi-kuroshine A (7), 5α-hydroxykuroshine A (8), 7β-hydroxykuroshine A (9), 11-keto-oxyzoanthamine (10), and 30-hydroxyzoanthamine (11), along with eight known compounds (12-19). The structures of these compounds were identified by detailed spectroscopic data, including HRESIMS, IR, NMR, and UV spectra. All secondary metabolites isolated from Z. vietnamensis were investigated for the anti-angiogenic effect in human endothelial progenitor cells (EPCs). Compounds 6, 7, 11, and 13 exhibited mild anti-angiogenic effect by blocking cell growth and tube formation of EPCs. The neuroprotective potential of four major compounds 12, 14, 15, and 19 against paclitaxel-induced neurotoxicity was evaluated. Pretreatment of 14 and 15 protected paclitaxel-damaged neurite outgrowth of dorsal root ganglion (DRG) neurons, without interfering the cytotoxic activity of paclitaxel on cervical cancer SiHa cells.

Keywords: Anti-angiogenic activity; Marine natural product; Neuroprotection; Zoanthus vietnamensis.

Publication types

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

MeSH terms

Alkaloids / chemistry
Alkaloids / pharmacology*
Animals
Anthozoa / chemistry*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Survival / drug effects*
Drug Discovery
Ganglia, Spinal / cytology
Humans
Mice
Molecular Structure
Neovascularization, Pathologic / drug therapy*
Neurons / drug effects*
Paclitaxel / toxicity
Stem Cells / drug effects

Substances

Alkaloids
Antineoplastic Agents
Paclitaxel