COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci

International Journal of Molecular Sciences

Chayanard Phukhamsakda¹  Frank Surup²  Gian Primahana²  Marc Stadler²  Andreas Ratzenböck³  Jeremiah Francis A. Llaguno⁴  Allan Patrick G. Macabeo⁴  Hans-Martin Dahse⁵  Mark Joseph B. Cano⁶  Mark Tristan J. Quimque⁶  Katherine Yasmin M. Garcia⁶ 

[1] Center of Excellence in Fungal Research, Mae Fah Luang University, Chiang Rai 57100, Thailand;Department of Microbial Drugs, Helmholtz Centre for Infection Research and German Centre for Infection Research (DZIF), Partner Site Hannover/Braunschweig, Inhoffenstrasse 7, 38124 Braunschweig, Germany;Institut für Organische Chemie, Universität Regensburg, Universitätstrasse 31, 93053 Regensburg, Germany;Laboratory for Organic Reactivity, Discovery and Synthesis (LORDS), Research Center for the Natural and Applied Sciences, University of Santo Tomas, España Blvd., Manila 1015, Philippines;Leibniz-Institute for Natural Product Research and Infection Biology, Hans-Knöll-Institute (HKI), 07745 Jena, Germany;The Graduate School, University of Santo Tomas, España Blvd., Manila 1015, Philippines;

关键词: Sparticola junci;    structure elucidation;    ECD-TDDFT;    COX inhibitory;    molecular docking;    antiproliferative;   

DOI  :  10.3390/ijms222212379

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown