Discovery and Photoisomerization of New Pyrrolosesquiterpenoids Glaciapyrroles D and E, from Deep-Sea Sediment Streptomyces sp.

Keebeom Ko, Seong Hwan Kim, Subin Park, Hwa Seung Han, Jae Kyun Lee, Jin Wook Cha, Sunghoon Hwang, Ki Young Choi, Yoon Jae Song, Sang Jip Nam, Jongheon Shin, Seung Il Nam, Hak Cheol Kwon, Jin Soo Park, Dong Chan Oh

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5 Scopus citations

Abstract

Two new pyrrolosesquiterpenes, glaciapyrroles D (1) and E (2) were discovered along with the previously reported glaciapyrrole A (3) from Streptomyces sp. GGS53 strain isolated from deep-sea sediment. This study elucidated the planar structures of 1 and 2 using nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV), and infrared (IR) spectroscopic data. The absolute configurations of the glaciapyrroles were determined by Mosher’s method, circular dichroism spectroscopy, and X-ray crystallography. Under 366 nm UV irradiation, the glaciapyrroles were systematically converted to the corresponding photoglaciapyrroles (4–6) via photoisomerization, resulting in the diversification of the glaciapyrrole family compounds. The transformation of the glaciapyrrole Z to E isomers occurred in a 1:1 ratio, based on virtual validation of the photoisomer-ization of these olefinic compounds by1 H-NMR spectroscopy and liquid chromatography/mass spectrometry (LC/MS) analysis. Finally, when encapsulated in poly(lactic-co-glycolic acid) nanopar-ticles, glaciapyrrole E and photoglaciapyrrole E displayed significant inhibitory activity against influenza A virus. This is the first report of antiviral effects from glaciapyrrole family compounds, whose biological functions have only been subjected to limited studies so far.

Original languageEnglish
Article number281
JournalMarine Drugs
Volume20
Issue number5
DOIs
StatePublished - May 2022

Bibliographical note

Funding Information:
Funding: This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korea government (Ministry of Science and ICT) (2020R1A2C2003518 and 2021R1A4A 2001251) and Korea Institute of Science and Technology (KIST) Open Research Program 2E31881 and Basic Research Program of KOPRI (PE14062).

Publisher Copyright:
© 2022 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

  • Streptomyces
  • deep-sea sediment
  • glaciapyrrole
  • photoisomerization
  • pyrrolosesquiterpene
  • structure elucidation

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