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. 2021 Nov 17;22(22):12379.
doi: 10.3390/ijms222212379.

COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci

Katherine Yasmin M Garcia  1   2 , Mark Tristan J Quimque  1   2   3 , Gian Primahana  4   5   6 , Andreas Ratzenböck  7 , Mark Joseph B Cano  1   2 , Jeremiah Francis A Llaguno  2 , Hans-Martin Dahse  8 , Chayanard Phukhamsakda  9   10 , Frank Surup  4   5 , Marc Stadler  4   5 , Allan Patrick G Macabeo  2
Affiliations

COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci

Katherine Yasmin M Garcia et al. Int J Mol Sci. .

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.

Keywords: COX inhibitory; ECD-TDDFT; Sparticola junci; antiproliferative; cytotoxic; molecular docking; structure elucidation.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Dioxynaphthalenoids 1–3 from Sparticola junci.
Figure 2
Figure 2
COSY and HMBC correlations in 1 and 2.
Figure 3
Figure 3
Experimental ECD spectrum of sparticatechol A (1, black solid curve) compared with B3LYP/6-31G(d)-calculated ECD spectra (red solid curve) for the B3LYP/6-31G(d)-optimized conformers of (8S,22R)-1.
Figure 4
Figure 4
Experimental ECD spectrum of sparticolin H (2, black solid curve) compared with WB97XD/DGDZVP (PCM/MeCN)-calculated ECD spectra (red solid curve) for the WB97XD/DGDZVP-optimized conformers of (4S,5S,7R)-2.
Figure 5
Figure 5
3D and 2D docked poses of sparticatechol A (1) against (A) COX-2 (PDB ID: 3LN1) and (B) COX-1 (PDB ID: 3KK6).
Figure 6
Figure 6
Prediction of GI tract and brain permeation of compounds 1–3 by brain or the intestinal estimated permeation predictive model (BOILED-Egg) method.
See this image and copyright information in PMC

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