6533b822fe1ef96bd127cbf5
RESEARCH PRODUCT
Hydroquinone derivatives from the marine-derived fungus Gliomastix sp.
Mohamed S. ElnaggarMohamed S. ElnaggarTibor KurtánWerner E.g. MüllerRainer KalscheuerPeter ProkschAttila MándiAbdel Nasser B. SingabWenhan LinWeaam EbrahimWeaam EbrahimZhen Liusubject
biologyHydroquinone010405 organic chemistryStereochemistryGeneral Chemical EngineeringAlkaloidGliomastixGeneral ChemistryFungusbiology.organism_classification01 natural sciences0104 chemical sciencesMycobacterium tuberculosis010404 medicinal & biomolecular chemistrychemistry.chemical_compoundTermészettudományokchemistryIc50 valuesKémiai tudományokCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopydescription
Eight new hydroquinone derivatives, gliomastins A–D (1–4), 9-O-methylgliomastin C (5), acremonin A 1-O-β-D-glucopyranoside (6), gliomastin E 1-O-β-D-glucopyranoside (7), and 6′-O-acetyl-isohomoarbutin (8), together with seven known analogues were isolated from the marine-derived fungus Gliomastix sp. Their structures were elucidated by extensive spectroscopic analysis including 1D and 2D NMR measurements aided by DFT NMR calculations as well as MS data. TDDFT-ECD and OR calculations were performed to determine the absolute configurations of 1 and the aglycones of 6 and 7. Compound 1 features a novel skeleton, biogenetically derived from a Diels–Alder reaction between derivatives of 11 and 13. Compound 2 represents a rare sulfur-containing alkaloid derived from the known hydroquinone 13. Compounds 1, 10 and 12 showed strong cytotoxicity against the L5178Y mouse lymphoma cell line with IC50 values of 1.8, 1.0 and 1.1 μM, respectively. Compound 3 exhibited moderate antitubercular activity against Mycobacterium tuberculosis with a MIC value of 12.5 μM.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-01-01 | RSC Advances |