Isolation, structure elucidation, and antibacterial evaluation of the metabolites produced by the marine-sourced Streptomyces sp. ZZ820. Issue 9 (1st March 2019)

• Record Type: Journal Article
• Authors: Yi, Wenwen; Li, Qiao; Song, Tengfei; Chen, Lei; Li, Xing-Cong; Zhang, Zhizhen; Lian, Xiao-Yuan
• Is Part Of: Tetrahedron. Volume 75:Issue 9(2019)
• Page Start: 1186
• Page End: 1193
• Publication Date: 2019-03-01
• Subjects: Streptomyces sp. ZZ820 -- Marine actinomycetes -- Streptoprenylindoles -- Cyclooctatin analogues -- Antibacterial activities; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.01.025
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: New indole alkaloids streptoprenylindoles A–C (1 –3 ) and diterpenoids 18-acetyl-cyclooctatin (8 ), 5, 18-dedihydroxy-cyclooctatin (9 ), and 5-dehydroxy-cyclooctatin (10 ) were isolated from the culture of marine-derived Streptomyces sp. ZZ820, along with known 3-cyanomethyl-6-[3-methyl-2-butenyl]indole (4 ), N -(2-(1 H -indol-3-yl)ethylacetamide (5 ), 1-acetyl-β-carboline (6 ), indole-3-methylethanoate (7 ), cyclooctatin (11 ), and chromomycin A3 (12 ). Their structures were elucidated by a combination of extensive spectroscopic analyses, ECD calculation, and the Mosher's method. Streptoprenylindoles A (1 ) and B (2 ) are enantiomers that were separated through the preparation of their Mosher esters. Three new diterpenoids (8 –10 ) showed antibacterial activities against methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli with MIC values of 24.11–55.12 μM, while chromomycin A3 (12 ) showed potent antibacterial activities against MRSA (MIC: 0.59 μM) and E. coli (MIC 0.04 μM). Graphical abstract: Image 1 Highlights: Six previously undescribed compounds are reported in this study. Streptoprenylindoles A and B were separated by the preparation of their Mosher esters. Four diterpenoids and chromomycin A3 showed activities against MRSA and E. coli.