Gwanakosides A and B, 6-Deoxy-α-l-talopyranose-Bearing Aromatic Metabolites from a Streptomyces sp. and Coculture with Pandoraea sp.

Thanh Hau Huynh, Jayho Lee, Dong Hyun Moon, Thanh Quang Nguyen, Sangkeun Son, Sunghoon Hwang, Young Eun Du, Jinsheng Cui, Jae Hyuk Jang, Sang Jip Nam, Jongheon Shin, Jichan Jang, Sang Kook Lee, Ki Bong Oh, Dong Chan Oh

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Single-strain cultivation of a mountain soil-derived Streptomyces sp. GA02 and its coculture with Pandoraea sp. GA02N produced two aromatic products, gwanakosides A and B (1 and 2, respectively). Their spectroscopic analysis revealed that 1 is a new dichlorinated naphthalene glycoside and 2 is a pentacyclic aromatic glycoside. The assignment of the two chlorine atoms in 1 was confirmed by the analysis of its band-selective CLIP-HSQMBC spectrum. The sugars in the gwanakosides were identified as 6-deoxy-α-l-talopyranose based on 1H–1H coupling constants, Rotating frame Overhauser enhancement spectroscopy (ROESY) NMR correlations, and chemical derivatization followed by spectroscopic and chromatographic analyses. The absolute configuration of 2, whose production was enhanced approximately 100-fold in coculture, was proposed based on a quantum mechanics-based chemical shift analysis method, DP4 calculations, and the chemically determined configuration of 6-deoxy-α-l-talopyranose. Gwanakoside A displayed inhibitory activity against pathogenic bacteria, including Staphylococcus aureus (MIC = 8 μg/mL) and Mycobacterium tuberculosis (MIC50 = 15 μg/mL), and antiproliferative activity against several human cancer cell lines (IC50 = 5.6–19.4 μM).

Original languageEnglish
Pages (from-to)83-90
Number of pages8
JournalJournal of Natural Products
Volume85
Issue number1
DOIs
StatePublished - 28 Jan 2022

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© 2021 American Chemical Society and American Society of Pharmacognosy

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