Two New Phenylhydrazone Derivatives from the Pearl River Estuary Sediment-Derived Streptomyces sp. SCSIO 40020

Wei Liu; Liang Ma; Liping Zhang; Yuchan Chen; Qingbo Zhang; Haibo Zhang; Weimin Zhang; Changsheng Zhang; Wenjun Zhang

doi:10.3390/md20070449

Two New Phenylhydrazone Derivatives from the Pearl River Estuary Sediment-Derived Streptomyces sp. SCSIO 40020

Mar Drugs. 2022 Jul 9;20(7):449. doi: 10.3390/md20070449.

Authors

Wei Liu^{1

2}, Liang Ma^{1

3}, Liping Zhang^{1

3}, Yuchan Chen², Qingbo Zhang^{1

3}, Haibo Zhang^{1

3}, Weimin Zhang², Changsheng Zhang^{1

3

4}, Wenjun Zhang^{1

3

4}

Affiliations

¹ Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Innovation Academy for South China Sea Ecology and Environmental Engineering, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, China.
² State Key Laboratory of Applied Microbiology Southern China, Institute of Microbiology, Guangdong Academy of Sciences, 100 Central Xianlie Road, Guangzhou 510070, China.
³ Southern Marine Science and Engineering Guangdong Laboratory (Guangzhou), No.1119, Haibin Road, Guangzhou 511458, China.
⁴ University of Chinese Academy of Sciences, Beijing 100049, China.

Abstract

Two new phenylhydrazone derivatives and one new alkaloid, penzonemycins A-B (1-2) and demethylmycemycin A (3), together with three known compounds including an alkaloid (4) and two sesquiterpenoids (5-6), were isolated from the Streptomyces sp. SCSIO 40020 obtained from the Pearl River Estuary sediment. Their structures and absolute configurations were assigned by 1D/2D NMR, mass spectroscopy and X-ray crystallography. Compound 1 was evaluated in four human cancer cell lines by the SRB method and displayed weak cytotoxicity in three cancer cell lines, with IC₅₀ values that ranged from 30.44 to 61.92 µM, which were comparable to those of the positive control cisplatin. Bioinformatic analysis of the putative biosynthetic gene cluster indicated a Japp-Klingemann coupling reaction involved in the hydrazone formation of 1 and 2.

Keywords: Japp–Klingemann coupling reaction; Streptomyces sp.; marine natural products; penzonemycins; phenylhydrazones.

MeSH terms

Alkaloids*
Estuaries
Humans
Hydrazones
Molecular Structure
Rivers
Streptomyces* / chemistry
Streptomyces* / genetics

Substances

Alkaloids
Hydrazones
phenylhydrazone

Grants and funding

This work was supported in part by NSFC (42176127, 22193072, 21907098), Guangdong Basic and Applied Basic Research Foundation (2021A1515110284, 2021A1515010839), by the Science and Technology Planning Project of Guangzhou (202102020513), K. C. Wong Education Foundation (GJTD-2020-12), by the State Key Laboratory of Applied Microbiology, Southern China (Grant No. SKLAM004-2021).