COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci

Garcia, Katherine Yasmin M. and Quimque, Mark Tristan J. and Primahana, Gian and Ratzenboeck, Andreas and Cano, Mark Joseph B. and Llaguno, Jeremiah Francis A. and Dahse, Hans-Martin and Phukhamsakda, Chayanard and Surup, Frank and Stadler, Marc and Macabeo, Allan Patrick G. (2021) COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22 (22): 12379. ISSN 1422-0067

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Abstract

Axenic fermentation on solid rice of the saprobic fungus Sparticola junci afforded two new highly oxidized naphthalenoid polyketide derivatives, sparticatechol A (1) and sparticolin H (2) along with sparticolin A (3). The structures of 1 and 2 were elucidated on the basis of their NMR and HR-ESIMS spectroscopic data. Assignment of absolute configurations was performed using electronic circular dichroism (ECD) experiments and Time-Dependent Density Functional Theory (TDDFT) calculations. Compounds 1-3 were evaluated for COX inhibitory, antiproliferative, cytotoxic and antimicrobial activities. Compounds 1 and 2 exhibited strong inhibitory activities against COX-1 and COX-2. Molecular docking analysis of 1 conferred favorable binding against COX-2. Sparticolin H (2) and A (3) showed a moderate antiproliferative effect against myelogenous leukemia K-562 cells and weak cytotoxicity against HeLa and mouse fibroblast cells.

Item Type: Article
Uncontrolled Keywords: CLADOSPIRONE BISEPOXIDE; FUNGUS; BIOSYNTHESIS; DERIVATIVES; SYSTEM; Sparticola junci; structure elucidation; ECD-TDDFT; COX inhibitory; molecular docking; antiproliferative; cytotoxic
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 13 Sep 2022 09:41
Last Modified: 13 Sep 2022 09:41
URI: https://pred.uni-regensburg.de/id/eprint/48024

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