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- Title
Tandocyclinones A and B, Ether Bridged C -Glycosyl Benz[ a ]anthracenes from an Intertidal Zone Streptomyces sp.
- Authors
Huynh, Thanh-Hau; Bae, Eun Seo; Heo, Bo Eun; Lee, Jayho; An, Joon Soo; Kwon, Yun; Nam, Sang-Jip; Oh, Ki-Bong; Jang, Jichan; Lee, Sang Kook; Oh, Dong-Chan
- Abstract
Two new proton-deficient metabolites, tandocyclinones A and B (1 and 2), were discovered via the chemical profiling of the Streptomyces sp. strain TDH03, which was isolated from a marine sediment sample collected from the intertidal mudflat in Tando Port, the Republic of Korea. The structures of 1 and 2 were elucidated as new ether-bridged C-glycosyl benz[a]anthracenes by using a combination of spectroscopic analyses of ultraviolet (UV) and mass spectrometry (MS) data, along with nuclear magnetic resonance (NMR) spectra, which were acquired in tetrahydrofuran (THF)-d8 selected after an extensive search for a solvent, resulting in mostly observable exchangeable protons in the 1H NMR spectrum. Their configurations were successfully assigned by applying a J-based configuration analysis, rotating-frame Overhauser enhancement spectroscopy (ROESY) NMR correlations, chemical derivatization methods based on NMR (a modified version of Mosher's method) and circular dichroism (CD) (Snatzke's method using Mo2(OAc)4-induced CD), as well as quantum-mechanics-based computational methods, to calculate the electronic circular dichroism (ECD). Tandocyclinones A and B (1 and 2) were found to have weak antifungal activity against Trichophyton mentagrophytes IFM40996 with an MIC value of 128 μg/mL (244 and 265 μM for 1 and 2, respectively). A further biological evaluation revealed that tandocyclinone A (1) displayed inhibitory activity against Mycobacterium avium (MIC50 = 40.8 μM) and antiproliferative activity against SNU638 and HCT116 cancer cells, with IC50 values of 31.9 µM and 49.4 µM, respectively.
- Subjects
SOUTH Korea; INTERTIDAL zonation; STREPTOMYCES; MYCOBACTERIUM avium; NUCLEAR magnetic resonance; CIRCULAR dichroism; ANTHRACENE; ANTHRACENE derivatives
- Publication
Marine Drugs, 2023, Vol 21, Issue 9, p500
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md21090500