A unique indolizinium alkaloid streptopertusacin A and bioactive bafilomycins from marine-derived Streptomyces sp. HZP-2216E. (December 2017)

• Record Type: Journal Article
• Authors: Zhang, Xiufang; Chen, Lu; Chai, Weiyun; Lian, Xiao-Yuan; Zhang, Zhizhen
• Is Part Of: Phytochemistry. Volume 144(2017)
• Page Start: 119
• Page End: 126
• Publication Date: 2017-12
• Subjects: Streptomyces sp. -- Marine actinomycete -- Streptopertusacin A -- Bafilomycins -- Antiproliferative and antibacterial activities -- Glioma cells -- Methicillin-resistant Staphylococcus aureus; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2017.09.010
• Languages: English
• ISSNs: 0031-9422

Abstract

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. Graphical abstract: A unique indolizinium alkaloid streptopertusacin A (1 ) existing as a zwitterion and two previously undescribed bafilomycin analogues of 21, 22-en-bafilomycin D (2 ) and 21, 22-en-9-hydroxybafilomycin D (3 ) were isolated from a culture of seaweed-derived Streptomyces sp. HZP-2216E. Bafilomycins2 and3 had potent activities in inhibiting the proliferation of glioma cells and the growth of methicillin-resistant Staphylococcus aureus . Highlights: Streptopertusacin A and bioactive bafilomycins were isolated from Streptomyces sp. Streptopertusacin A is a unique indolizinium alkaloid existing as a zwitterion. Bafilomycins showed potent activity against the proliferation of glioma cells. Bafilomycins had activity against methicillin-resistant Staphylococcus aureus.