COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from Sparticola junci

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 st...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Katherine Yasmin M. Garcia, Mark Tristan J. Quimque, Gian Primahana, Andreas Ratzenböck, Mark Joseph B. Cano, Jeremiah Francis A. Llaguno, Hans-Martin Dahse, Chayanard Phukhamsakda, Frank Surup, Marc Stadler, Allan Patrick G. Macabeo
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	<i>Sparticola junci</i> structure elucidation ECD-TDDFT COX inhibitory molecular docking antiproliferative Biology (General) QH301-705.5 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/c385e909fad44c9dbb7d831d65acde72
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:c385e909fad44c9dbb7d831d65acde72
record_format	dspace
spelling	oai:doaj.org-article:c385e909fad44c9dbb7d831d65acde722021-11-25T17:55:57ZCOX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>10.3390/ijms2222123791422-00671661-6596https://doaj.org/article/c385e909fad44c9dbb7d831d65acde722021-11-01T00:00:00Zhttps://www.mdpi.com/1422-0067/22/22/12379https://doaj.org/toc/1661-6596https://doaj.org/toc/1422-0067Axenic fermentation on solid rice of the saprobic fungus <i>Sparticola junci</i> afforded two new highly oxidized naphthalenoid polyketide derivatives, sparticatechol A (<b>1</b>) and sparticolin H (<b>2</b>) along with sparticolin A (<b>3</b>). The structures of <b>1</b> and <b>2</b> 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 <b>1–3</b> were evaluated for COX inhibitory, antiproliferative, cytotoxic and antimicrobial activities. Compounds <b>1</b> and <b>2</b> exhibited strong inhibitory activities against COX-1 and COX-2. Molecular docking analysis of <b>1</b> conferred favorable binding against COX-2. Sparticolin H (<b>2</b>) and A (<b>3</b>) showed a moderate antiproliferative effect against myelogenous leukemia K-562 cells and weak cytotoxicity against HeLa and mouse fibroblast cells.Katherine Yasmin M. GarciaMark Tristan J. QuimqueGian PrimahanaAndreas RatzenböckMark Joseph B. CanoJeremiah Francis A. LlagunoHans-Martin DahseChayanard PhukhamsakdaFrank SurupMarc StadlerAllan Patrick G. MacabeoMDPI AGarticle<i>Sparticola junci</i>structure elucidationECD-TDDFTCOX inhibitorymolecular dockingantiproliferativeBiology (General)QH301-705.5ChemistryQD1-999ENInternational Journal of Molecular Sciences, Vol 22, Iss 12379, p 12379 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	<i>Sparticola junci</i> structure elucidation ECD-TDDFT COX inhibitory molecular docking antiproliferative Biology (General) QH301-705.5 Chemistry QD1-999
spellingShingle	<i>Sparticola junci</i> structure elucidation ECD-TDDFT COX inhibitory molecular docking antiproliferative Biology (General) QH301-705.5 Chemistry QD1-999 Katherine Yasmin M. Garcia Mark Tristan J. Quimque Gian Primahana Andreas Ratzenböck Mark Joseph B. Cano Jeremiah Francis A. Llaguno Hans-Martin Dahse Chayanard Phukhamsakda Frank Surup Marc Stadler Allan Patrick G. Macabeo COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>
description	Axenic fermentation on solid rice of the saprobic fungus <i>Sparticola junci</i> afforded two new highly oxidized naphthalenoid polyketide derivatives, sparticatechol A (<b>1</b>) and sparticolin H (<b>2</b>) along with sparticolin A (<b>3</b>). The structures of <b>1</b> and <b>2</b> 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 <b>1–3</b> were evaluated for COX inhibitory, antiproliferative, cytotoxic and antimicrobial activities. Compounds <b>1</b> and <b>2</b> exhibited strong inhibitory activities against COX-1 and COX-2. Molecular docking analysis of <b>1</b> conferred favorable binding against COX-2. Sparticolin H (<b>2</b>) and A (<b>3</b>) showed a moderate antiproliferative effect against myelogenous leukemia K-562 cells and weak cytotoxicity against HeLa and mouse fibroblast cells.
format	article
author	Katherine Yasmin M. Garcia Mark Tristan J. Quimque Gian Primahana Andreas Ratzenböck Mark Joseph B. Cano Jeremiah Francis A. Llaguno Hans-Martin Dahse Chayanard Phukhamsakda Frank Surup Marc Stadler Allan Patrick G. Macabeo
author_facet	Katherine Yasmin M. Garcia Mark Tristan J. Quimque Gian Primahana Andreas Ratzenböck Mark Joseph B. Cano Jeremiah Francis A. Llaguno Hans-Martin Dahse Chayanard Phukhamsakda Frank Surup Marc Stadler Allan Patrick G. Macabeo
author_sort	Katherine Yasmin M. Garcia
title	COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>
title_short	COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>
title_full	COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>
title_fullStr	COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>
title_full_unstemmed	COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>
title_sort	cox inhibitory and cytotoxic naphthoketal-bearing polyketides from <i>sparticola junci</i>
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/c385e909fad44c9dbb7d831d65acde72
work_keys_str_mv	AT katherineyasminmgarcia coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT marktristanjquimque coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT gianprimahana coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT andreasratzenbock coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT markjosephbcano coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT jeremiahfrancisallaguno coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT hansmartindahse coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT chayanardphukhamsakda coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT franksurup coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT marcstadler coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii AT allanpatrickgmacabeo coxinhibitoryandcytotoxicnaphthoketalbearingpolyketidesfromisparticolajuncii
_version_	1718411827077971968

COX Inhibitory and Cytotoxic Naphthoketal-Bearing Polyketides from <i>Sparticola junci</i>

Ejemplares similares