A unique indolizinium alkaloid streptopertusacin A and bioactive bafilomycins from marine-derived Streptomyces sp. HZP-2216E.

Xiufang Zhang, Lu Chen, Weiyun Chai, Xiao-Yuan Lian, Zhizhen Zhang
Author Information
  1. Xiufang Zhang: Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, China.
  2. Lu Chen: Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, China.
  3. Weiyun Chai: Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, China.
  4. Xiao-Yuan Lian: College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China. Electronic address: xylian@zju.edu.cn.
  5. Zhizhen Zhang: Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, China. Electronic address: zzhang88@zju.edu.cn.

Abstract

Streptopertusacin A, a unique indolizinium alkaloid existing as a zwitterion, and six bafilomycins including two previously undescribed ones of 21,22-en-bafilomycin D and 21,22-en-9-hydroxybafilomycin D were isolated from a culture of the seaweed-derived Streptomyces sp. HZP-2216E. Structures of these isolated compounds were determined based on extensive NMR spectroscopic analyses, HRESIMS and MS-MS data. The stereochemical assignments were achieved by NOE information, chemical degradation, Marfey's method, and electronic circular dichroism (ECD) calculation. Streptopertusacin A is the first example of this type of indolizinium alkaloid from microorganisms and showed moderate activity against the growth of methicillin-resistant Staphylococcus aureus (MRSA). 21,22-en-bafilomycin D and 21,22-en-9-hydroxybafilomycin D had potent activities in inhibiting the proliferation of glioma cells and the growth of MRSA.

Keywords

MeSH Term

Animals
Anti-Bacterial Agents
Cell Proliferation
Dose-Response Relationship, Drug
Glioma
Humans
Macrolides
Methicillin-Resistant Staphylococcus aureus
Microbial Sensitivity Tests
Molecular Conformation
Phenazines
Rats
Streptomyces
Structure-Activity Relationship
Tumor Cells, Cultured

Chemicals

Anti-Bacterial Agents
Macrolides
Phenazines
streptophenazine A
bafilomycin D

Word Cloud

Created with Highcharts 10.0.021DStreptopertusacinindoliziniumalkaloidStreptomycesspuniquebafilomycins22-en-bafilomycin22-en-9-hydroxybafilomycinisolatedHZP-2216EgrowthStaphylococcusaureusMRSAactivitiescellsexistingzwitterionsixincludingtwopreviouslyundescribedonescultureseaweed-derivedStructurescompoundsdeterminedbasedextensiveNMRspectroscopicanalysesHRESIMSMS-MSdatastereochemicalassignmentsachievedNOEinformationchemicaldegradationMarfey'smethodelectroniccirculardichroismECDcalculationfirstexampletypemicroorganismsshowedmoderateactivitymethicillin-resistantpotentinhibitingproliferationgliomastreptopertusacinbioactivemarine-derivedAntiproliferativeantibacterialBafilomycinsGliomaMarineactinomyceteMethicillin-resistant

Similar Articles

Cited By