Angucyclines containing β-ᴅ-glucuronic acid from Streptomyces sp. KCB15JA151

Gil Soo Kim; Jun-Pil Jang; Tae Hoon Oh; Mincheol Kwon; Byeongsan Lee; Jung-Sook Lee; Sung-Kyun Ko; Young-Soo Hong; Jong Seog Ahn; Jae-Hyuk Jang

doi:10.1016/j.bmcl.2021.128237

Angucyclines containing β-ᴅ-glucuronic acid from Streptomyces sp. KCB15JA151

Bioorg Med Chem Lett. 2021 Sep 15:48:128237. doi: 10.1016/j.bmcl.2021.128237. Epub 2021 Jul 1.

Authors

Affiliations

¹ Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju 28116, Republic of Korea; Department of Biomolecular Science, KRIBB School of Bioscience, University of Science and Technology, Daejeon 34113, Republic of Korea.
² Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju 28116, Republic of Korea.
³ Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju 28116, Republic of Korea; College of Pharmacy, Chungbuk National University, Cheongju 28160, Republic of Korea.
⁴ Korean Collection for Type Cultures, Korea Research Institute of Bioscience and Biotechnology, Jeongeup 56212, Republic of Korea.
⁵ Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju 28116, Republic of Korea; Department of Biomolecular Science, KRIBB School of Bioscience, University of Science and Technology, Daejeon 34113, Republic of Korea. Electronic address: jsahn@kribb.re.kr.
⁶ Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology, Cheongju 28116, Republic of Korea; Department of Biomolecular Science, KRIBB School of Bioscience, University of Science and Technology, Daejeon 34113, Republic of Korea. Electronic address: jangjh@kribb.re.kr.

PMID: 34216745
DOI: 10.1016/j.bmcl.2021.128237

Abstract

Two angucyclines, pseudonocardones D (1) and E (2), were isolated from Streptomyces sp. KCB15JA151. The planar structure was elucidated by comprehensive spectroscopic analysis. The absolute configuration of the sugar unit was determined based on the basis of coupling constants, ROESY, chemical derivatization and HPLC analysis. The biological activities of compounds 1 and 2 were examined by performing a computational target prediction, which led to tests of the antiestrogenic activity. The result suggested that compound 1 might be an ERα antagonist.

Keywords: Angucycline; Streptomyces sp.; β-ᴅ-Glucuronic acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Dose-Response Relationship, Drug
Estrogen Receptor alpha / antagonists & inhibitors*
Estrogen Receptor alpha / metabolism
Glucuronic Acid / chemistry
Glucuronic Acid / isolation & purification
Glucuronic Acid / pharmacology*
Humans
Molecular Structure
Streptomyces / chemistry*
Structure-Activity Relationship

Substances

Estrogen Receptor alpha
Glucuronic Acid