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

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

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).

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