Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
The structure was elucidated in this paperNCBI PubMed ID: 28939024Publication DOI: 10.1016/S1875-5364(17)30089-4Journal NLM ID: 101504416Publisher: Beijing: Science Press; Elsevier
Correspondence: Zhang J <wilson1978
163.com>
Institutions: Jiangsu Provincial Key Laboratory for TCM Evaluation and Translational Research, China Pharmaceutical University, Nanjing, China, Institute of Biotechnology for TCM Research, School of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing, China
With an attempt to synthesize high-value isoquercitrin (quercetin-3-O-β-D-glucopyranoside), we carried out the biotransformation of quercetin (1) by Gliocladium deliquescens NRRL 1086. Along with the aimed product quercetin 3-O-β-D-glycoside (2), three additional metabolites, 2-protocatechuoyl-phlorogucinol carboxylic acid (3), 2,4,6-trihydroxybenzoic acid (4), and protocatechuic acid (5), were also isolated. The time-course experiments revealed that there were two metabolic routes, regio-selectivity glycosylation and quercetin 2,3-dioxygenation, co-existing in the culture. Both glycosylation and oxidative cleavage rapidly took place after quercetin feeding; about 98% quercetin were consumed within the initial 8 h and the oxdized product (2-protocatechuoyl-phlorogucinol carboxylic acid) was hydrolyzed into two phenolic compounds (2,4,6-trihydroxybenzoic acid and protocatechuic acid). We also investigated the impact of glucose content and metal ions on the two reactions and found that high concentrations of glucose significantly inhibited the oxidative cleavage and improved the yield of isoquercitrin and that Ca2+, Fe2+, Mn2+, Mg2+, and Zn2+ inhibited glycosylation. To test the promiscuity of this culture, we selected other four flavonols as substrates; the results demonstrated its high regio-selectivity glycosylation ability towards flavonols at C-3 hydroxyl. In conclusion, our findings indicated that the versatile microbe of G. deliquescens NRRL 1086 maitained abundant enzymes, deserving further research.
glycosylation, quercetin, biotransformation, Gliocladium deliquescens NRRL 1086, quercetin-2, 3-dioxygenase
Structure type: monomer ; 465.1 [M+H]+
C
21H
20O
11Location inside paper: compound 2, table 1(2), fig. 3(2)
Trivial name: isoquercitrin
Compound class: flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, ESI-MS, HPLC, cell growth
Synthetic data: biosynthesis
Comments, role: compound 2 was produced by G. deliquescens NRRL 1086 from quercetin
Related record ID(s): 62231
NCBI Taxonomy refs (TaxIDs): 29861
Show glycosyltransferases
NMR conditions: in DMSO-d6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16
3 bDGlcp 100.9 74.1 77.4 69.9 76.4 60.8
xXQuercetin - 156.2 133.3 177.4 161.2 98.6 164.0 93.4 156.1 103.9 121.1 115.1 144.7 148.4 116.1 121.5
1H NMR data:
missing...
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3 | bDGlcp | 100.9 | 74.1 | 77.4 | 69.9 | 76.4 | 60.8 | |
| | xXQuercetin |
| 156.2 | 133.3 | 177.4 | 161.2 | 98.6 | 164.0 | 93.4 | 156.1 | 103.9 | 121.1 | 115.1 | 144.7 | 148.4 | 116.1 | 121.5 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
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