Retinestatin, a Polyol Polyketide from a Termite Nest-Derived Streptomyces sp

  • J Nat Prod. 2024 Mar 5. doi: 10.1021/acs.jnatprod.3c01043.
Thanh-Hau Huynh  1 ,  Hee Kyung Kim  2 ,  Jayho Lee  3 ,  Yeon Hee Ban  4 ,  Yong-Joon Jang  5 ,  Bo Eun Heo  6 ,  Thanh Quang Nguyen  6 ,  Joon Soo An  1 ,  Yun Kwon  7 ,  Sang-Jip Nam  8 ,  Jichan Jang  6 ,  Ki-Bong Oh  3 ,  Min-Kyoo Shin  1  2 ,  Dong-Chan Oh  1
Affiliations
  • 1. Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
  • 2. College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul 08826, Republic of Korea.
  • 3. Department of Agricultural Biotechnology, College of Agriculture and Life Sciences and Natural Products Research Institute, Seoul National University, Seoul 08826, Republic of Korea.
  • 4. Department of Molecular Bioscience, College of Biomedical Science, Kangwon National University, Chuncheon 24341, Republic of Korea.
  • 5. Natural Center of Life and Environment, Seoul 08826, Republic of Korea.
  • 6. Division of Life Science, Department of Bio & Medical Big Data (BK21 Four Program), Research Institute of Life Science, Gyeongsang National University, Jinju 52828, Republic of Korea.
  • 7. Research Institute of Pharmaceutical Sciences, College of Pharmacy, Kyungpook National University, Daegu 41566, Republic of Korea.
  • 8. Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of Korea.
PMID: 38442389 DOI: 10.1021/acs.jnatprod.3c01043
Abstract

A new polyol polyketide, named retinestatin (1), was obtained and characterized from the culture of a Streptomyces strain, which was isolated from a subterranean nest of the termite Reticulitermes speratus kyushuensis Morimoto. The planar structure of 1 was elucidated on the basis of the cumulative analysis of ultraviolet, infrared, mass spectrometry, and nuclear magnetic resonance spectroscopic data. The absolute configuration of 1 at 12 chiral centers was successfully assigned by employing a J-based configuration analysis in combination with ROESY correlations, a quantum mechanics-based computational approach to calculate NMR chemical shifts, and a 3 min flash esterification by Mosher's reagents followed by NMR analysis. Biological evaluation of retinestatin (1) using an in vitro model of Parkinson's disease revealed that 1 protected SH-SY5Y dopaminergic cells from MPP+-induced cytotoxicity, indicating its neuroprotective effects.

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