1856-95-7

Usage

InChI:InChI=1/C16H16O6/c1-16(19)7-10(17)14-12(22-16)5-8-4-9(20-2)6-11(21-3)13(8)15(14)18/h4-6,18-19H,7H2,1-3H3

Upstream product

• 4724-10-1 methyl 2-(3,5-dihydroxyphenyl)acetate 
• 28955-31-9 5-(2-methoxy-2-oxoethyl)-1,3-phenylene diacetate 
• 186581-53-3 diazomethane 
• 3748-39-8 fonsecin 

Relevant academic research and scientific papers

13C NMR Spectroscopy of Naphtho-γ-pyrones

The 13C NMR spectra of three naphtho-γ-pyrones produced by Aspergillus fonsecaeus (NRRL 67, O 16-1) viz. 5-hydroxy-6,8-dimethoxy-2-methyl-4H-naphthopyran-4-one (rubrofusarin B), 2,3-dihydro-2,5-dihydroxy-6,8-dimethoxy-2-methyl-4H-naphthopyran-4-one (fonsecin B) and 2,3-dihydro-2,5,8-trihydroxy-6-methoxy-2-methyl-4H-naphthopyran-4-one (fonsecin), have been determined.Assignments of the carbon resonances were carried out from chemical shifts, long-range carbon-hydrogen couplings and hydrogen-deuterium exchange information.Carbon shift assignments previouly reported for fonsecin have been revised.The C-4 and C-5 signals show that the angle of twist of the carbonyl group with the aryl ring system is larger in fonsecin than in fonsecin B, indicating the occurrence of different preferred conformations in the dihydropyrone ring of these compounds.

Synthesis of the Fungal Metabolite YWA1 and Related Constructs as Tools to Study MelLec-Mediated Immune Response to Aspergillus Infections ?

We describe the chemical synthesis of the fungal naphthopyrones YWA1 and fonsecin B, as well as their functionalization with an amine-spacer arm and the conjugation of the resulting molecules to three different functional tags (i.e., biotin, Oregon green, 1-[3-(succinimidyloxycarbonyl)benzyl]-4-[5-(4-methoxyphenyl)-2-oxazolyl]pyridinium bromide (PyMPO)). The naphthopyrone-biotin and -PyMPO constructs maintained the ability to bind the C-type lectin receptor MelLec, whose interaction with immunologically active fungal metabolites (i.e., 1,8-dihydroxynaphthalene-(DHN)-melanin and YWA1) is a key step in host recognition and induction of protective immune responses against Aspergillus fumigatus. The fluorescent Fonsecin B-PyMPO construct 21 was used to selectively visualize MelLec-expressing cells, thus validating the potential of this strategy for studying the role and functions of MelLec in immunity.