Taxonomic group: plant, fungi / Streptophyta, Ascomycota
(Phylum: Streptophyta, Ascomycota)
Organ / tissue: spores,
pericarp
NCBI PubMed ID: 24128471Publication DOI: 10.1016/j.foodchem.2013.08.048Journal NLM ID: 7702639Publisher: Elsevier Applied Science Publishers
Correspondence: Jiang Y <ymjiang
scbg.ac.cn>
Institutions: University of Chinese Academy of Sciences, Beijing, China, Key Laboratory of Plant Resource Conservation and Sustainable Utilization, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, China, Food Science Institute, Zhejiang Academy of Agricultural Sciences, Hangzhou, China, Department of Food, Nutrition and Packaging Sciences, Clemson University, Clemson, SC, USA
Our previous work exhibited Aspergillus awamori fermentation of the litchi pericarp increased significantly antioxidant activity and DNA protection effect. In this present study, the litchi pericarp and its aqueous-organic extracted residues were fermented by A. awamori in order to elucidate the enhanced beneficial effects. The study identified that rutin which present in litchi pericarp could be deglycosylated to form quercetin and quercetin-3-glucoside after the fermentation. Application the standard compounds (rutin, quercetin 3-glucoside, quercetin, kaempferol-3-glucoside and kaempferol) further revealed the effective biotransformation by A. awamori fermentation. It was hypothesised that rutin was initially dehydroxylated to form kaempferol-3-rutinoside and then deglycosylated to form kaempferol-3-glucoside and kaempferol. To our best knowledge, it is the first report on dehydroxylated effect of polyphenols caused by A. awamori fermentation. Thus, A. awamori fermentation can provide an effective way to produce health benefiting value-added products from litchi pericarp in food industry.
quercetin, Aspergillus awamori, dehydroxylation, kaempferol, litchi, pericarp
Structure type: monomer ; 463.0 [M+Na]+
C
21H
20O
12Location inside paper: F4, quercetin-3-glucoside, fig. 2c (26.5 min)
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, ESI-MS, GC, UV, statistical analysis, radical scavenging assay, HPLC-DAD, TFA hydrolysis
Synthetic data: biosynthesis
Comments, role: compound was obtained by A. awamori GIM 3.4 fermentation of L. chinensis pericarp
Related record ID(s): 47474
NCBI Taxonomy refs (TaxIDs): 151069,
105351
Show glycosyltransferases
NMR conditions: in CD3OD at 303 K
[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 105.7 75.7 78.1 71.2 78.1 62.6
xXQuercetin - 158.2 135.6 179.5 163.0 99.9 166.0 94.7 159.0 104.4 123.2 116.0 146.0 149.8 117.5 123.0
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3 bDGlcp 5.35 3.58-3.72 3.27 3.36 3.58-3.72 3.58-3.72
xXQuercetin - - - - - 6.20 - 6.39 - - - 7.71 - - 6.87 7.59
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12 C13/H13 C14/H14 C15/H15 C16/H16
3 bDGlcp 105.7/5.35 75.7/3.58-3.72 78.1/3.27 71.2/3.36 78.1/3.58-3.72 62.6/3.58-3.72
xXQuercetin 99.9/6.20 94.7/6.39 116.0/7.71 117.5/6.87 123.0/7.59
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3 | bDGlcp | 5.35 | 3.58
3.72 | 3.27 | 3.36 | 3.58
3.72 | 3.58
3.72 | |
| | xXQuercetin |
|
|
|
|
| 6.20 |
| 6.39 |
|
|
| 7.71 |
|
| 6.87 | 7.59 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3 | bDGlcp | 105.7 | 75.7 | 78.1 | 71.2 | 78.1 | 62.6 | |
| | xXQuercetin |
| 158.2 | 135.6 | 179.5 | 163.0 | 99.9 | 166.0 | 94.7 | 159.0 | 104.4 | 123.2 | 116.0 | 146.0 | 149.8 | 117.5 | 123.0 |
|
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
Found 
report error