2. Academic Validation
  3. Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species

Polyketides and Anthranilic Acid Possessing 6-Deoxy-α-l-talopyranose from a Streptomyces Species

  • J Nat Prod. 2017 May 26;80(5):1378-1386. doi: 10.1021/acs.jnatprod.6b01059.
Sangkeun Son 1 2,  Sung-Kyun Ko 1 2,  Mina Jang 1 2,  Jae Kyoung Lee 1,  Min Cheol Kwon 1 2,  Dong Hyo Kang 1 2,  In-Ja Ryoo 1,  Jung-Sook Lee 2 3,  Young-Soo Hong 1 2,  Bo Yeon Kim 1 2,  Jae-Hyuk Jang 1 2,  Jong Seog Ahn 1 2
Affiliations

Affiliations

  • 1 Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology , Cheongju 28116, Korea.
  • 2 Department of Biomolecular Science, University of Science and Technology , Daejeon 34141, Korea.
  • 3 Korean Collection for Type Cultures, Korea Research Institute of Bioscience and Biotechnology , Jeongeup 56212, Korea.
PMID: 28406643 DOI: 10.1021/acs.jnatprod.6b01059
Abstract

A bioassay-guided investigation in conjunction with chemical screening led to the isolation of three new glycosides, ulleungoside (1), 2-methylaminobenzoyl 6-deoxy-α-l-talopyranoside (2), and naphthomycinoside (3), along with three known secondary metabolites (5-7) from Streptomyces sp. KCB13F030. Their structures were elucidated by detailed NMR and MS spectroscopic analyses. Absolute configurational analysis of the sugar units based on the magnitudes of the coupling constants, NOESY correlations, chemical derivatization, and optical rotation measurements revealed that compounds 1-3 and 5 incorporate the rare deoxyhexose 6-deoxy-α-l-talopyranose. The absolute configuration of a polyketide extender unit of 3 was determined by applying the J-based configuration analysis and modified Mosher's method. Ulleungoside (1) and naphthomycin A (7) showed in vitro inhibitory effects against indoleamine 2,3-dioxygenase activity. Further bioevaluation revealed that compounds 1 and 7 had moderate antiproliferative activities against several Cancer cell lines, and compounds 5 and 6, which are members of the piericidin family, induced autophagosome accumulation.

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