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

  • J Nat Prod. 2022 Jan 28;85(1):83-90. doi: 10.1021/acs.jnatprod.1c00703.
Thanh-Hau Huynh  1 ,  Jayho Lee  2 ,  Dong Hyun Moon  1 ,  Thanh Quang Nguyen  3 ,  Sangkeun Son  4 ,  Sunghoon Hwang  1 ,  Young Eun Du  1 ,  Jinsheng Cui  1 ,  Jae-Hyuk Jang  4 ,  Sang-Jip Nam  5 ,  Jongheon Shin  1 ,  Jichan Jang  3 ,  Sang Kook Lee  1 ,  Ki-Bong Oh  2 ,  Dong-Chan Oh  1
Affiliations
  • 1. Natural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea.
  • 2. Department of Agricultural Biotechnology, College of Agriculture and Life Sciences, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea.
  • 3. Molecular Mechanism of Antibiotics, Division of Life Science, Division of Bio & Medical Big Data Department (BK4 Program), Research Institute of Life Science, Gyeongsang National University, Jinju 52828, Republic of Korea.
  • 4. Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju 28116, Republic of Korea.
  • 5. Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of Korea.
PMID: 34931849 DOI: 10.1021/acs.jnatprod.1c00703
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).