Taxonomic group: fungi / Mucoromycota
(Phylum: Mucoromycota)
The structure was elucidated in this paperPublication DOI: 10.1016/j.phytol.2014.06.009Journal NLM ID: 101513432Publisher: Amsterdam: Elsevier
Correspondence: He L <sxqiu
scbg.ac.cn>
Institutions: University of Chinese Academy of Sciences, Beijing, China, Program for Natural Product Medicinal Chemistry, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Guangzhou, China, Department of Plant Protection, Agricultural College, Jiangxi Agricultural University, Nanchang, China
The biotransformation of α-mangostin (1), prenylated xanthone isolated from the fruit hull of Garcinia mangostana Linn., by Cunninghamella blakesleana has been characterized. Due to regioselective glycosylation reactions at C3-OH, transformation of 1 gave two new higher polar compounds: α-mangostin-3-O-β-D-glucopyranoside (2), 4′-hydroxy-α-mangostin-3-O-β-D-glucopyranoside (3). Their structures were elucidated by spectroscopic analyses. Compound 2 displayed a lower cytotoxicity activity than 1, whereas they showed equal activity against Bacillus cereus.
glycosylation, biotransformation, Cunninghamella blakesleana, α-mangostin
Structure type: monomer ; 571.2171 [M-H]-
C
30H
36O
11Location inside paper: comopound 2, fig. 1(2), Table 3(2)
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, UV, optical rotation measurement, antibacterial assay, cytotoxicity assay, HMBC, HR–ESI-MS
Biological activity: In vitro inhibitory effects (MIC, μg/mL) of compound 2 against Staphyloccocus aureus (1.56), Bacillus subtilis (2.5), Bacillus cereus (0.78); In vitro cytotoxicity data of compound 2 by the MTT assay for cell lines (IC50, μM): A549 (6.70 ± 0.85), H460 (9.83 ± 0.35), Hela (3.76 ± 0.25)
Synthetic data: synthesis
Comments, role: compound was obtained by fermentation of α-mangostin by Cunninghamella blakesleana; NMR temperature was not specified
Related record ID(s): 47489
NCBI Taxonomy refs (TaxIDs): 155726
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24
3 bDGlcp 101.6 74.9 78.3 71.2 78.4 62.5
Subst 161.0 113.4 162.5 93.3 156.1 102.8 158.4 145.0 138.6 112.2 183.4 105.3 156.9 61.3 22.4 123.8 132.0 26.0 18.1 27.1 125.0 132.0 26.0 18.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24
3 bDGlcp 3.42-3.55 3.42-3.55 3.42-3.55 3.42-3.55 3.42-3.55 3.42-3.55
Subst - - 6.60 - 6.71 - 3.75 3.42-3.55 5.23 - 1.64 1.80 4.05 5.23 - 1.67 1.82 - 5.07 3.42-3.55 3.42-3.55 3.33-3.34 3.73 3.92
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 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24
3 bDGlcp 101.6/3.42-3.55 74.9/3.42-3.55 78.3/3.42-3.55 71.2/3.42-3.55 78.4/3.42-3.55 62.5/3.42-3.55
Subst 162.5/6.60 156.1/6.71 158.4/3.75 145.0/3.42-3.55 138.6/5.23 183.4/1.64 105.3/1.80 156.9/4.05 61.3/5.23 123.8/1.67 132.0/1.82 18.1/5.07 27.1/3.42-3.55 125.0/3.42-3.55 132.0/3.33-3.34 26.0/3.73 18.3/3.92
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 |
|---|
| 3 | bDGlcp | 3.42
3.55 | 3.42
3.55 | 3.42
3.55 | 3.42
3.55 | 3.42
3.55 | 3.42
3.55 | |
| | Subst |
|
| 6.60 |
| 6.71 |
| 3.75 | 3.42
3.55 | 5.23 |
| 1.64 | 1.80 | 4.05 | 5.23 |
| 1.67 | 1.82 |
| 5.07 | 3.42
3.55 | 3.42
3.55 | 3.33
3.34 | 3.73 | 3.92 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 |
|---|
| 3 | bDGlcp | 101.6 | 74.9 | 78.3 | 71.2 | 78.4 | 62.5 | |
| | Subst | 161.0 | 113.4 | 162.5 | 93.3 | 156.1 | 102.8 | 158.4 | 145.0 | 138.6 | 112.2 | 183.4 | 105.3 | 156.9 | 61.3 | 22.4 | 123.8 | 132.0 | 26.0 | 18.1 | 27.1 | 125.0 | 132.0 | 26.0 | 18.3 |
|
There is only one chemically distinct structure:
Taxonomic group: fungi / Mucoromycota
(Phylum: Mucoromycota)
The structure was elucidated in this paperPublication DOI: 10.1016/j.phytol.2014.06.009Journal NLM ID: 101513432Publisher: Amsterdam: Elsevier
Correspondence: He L <sxqiu
scbg.ac.cn>
Institutions: University of Chinese Academy of Sciences, Beijing, China, Program for Natural Product Medicinal Chemistry, Key Laboratory of Plant Resources Conservation and Sustainable Utilization, South China Botanical Garden, Guangzhou, China, Department of Plant Protection, Agricultural College, Jiangxi Agricultural University, Nanchang, China
The biotransformation of α-mangostin (1), prenylated xanthone isolated from the fruit hull of Garcinia mangostana Linn., by Cunninghamella blakesleana has been characterized. Due to regioselective glycosylation reactions at C3-OH, transformation of 1 gave two new higher polar compounds: α-mangostin-3-O-β-D-glucopyranoside (2), 4′-hydroxy-α-mangostin-3-O-β-D-glucopyranoside (3). Their structures were elucidated by spectroscopic analyses. Compound 2 displayed a lower cytotoxicity activity than 1, whereas they showed equal activity against Bacillus cereus.
glycosylation, biotransformation, Cunninghamella blakesleana, α-mangostin
Structure type: monomer ; 587.2135 [M-H]-
C
30H
36O
12Location inside paper: comopound 3, fig. 1(3), Table 3(3)
Compound class: phenolic glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, UV, optical rotation measurement, antibacterial assay, cytotoxicity assay, HMBC, HR–ESI-MS
Biological activity: In vitro inhibitory effects (MIC, μg/mL) of compound 3 against Staphyloccocus aureus (50), Bacillus subtilis (31.25), Bacillus cereus (12.5); In vitro cytotoxicity data of compound 2 by the MTT assay for cell lines (IC50, μM): A549 (31.91 ± 1.64), H460 (70.93 ± 3.076), Hela (14.72 ± 0.78)
Synthetic data: synthesis
Comments, role: compound was obtained by fermentation of α-mangostin by Cunninghamella blakesleana; NMR temperature was not specified
Related record ID(s): 47488
NCBI Taxonomy refs (TaxIDs): 155726
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24
3 bDGlcp 101.6 74.9 78.3 71.2 78.4 62.5
Subst 161.1 112.8 162.6 93.4 156.3 102.8 158.6 145.1 138.6 112.2 183.4 105.3 157.0 61.3 22.0 125.1 135.6 69.1 14.0 27.1 124.9 132.0 26.0 18.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24
3 bDGlcp 3.40-3.54 3.40-3.54 3.40-3.54 3.40-3.54 3.40-3.54 3.40-3.54
Subst - - 6.64 - 6.74 - 3.76 3.40-3.54 5.54 - 3.89-3.91 1.84 4.07 5.21 - 1.67 1.83 - 5.08 3.40-3.54 3.40-3.5 3.40-3.54 3.72 3.89-3.91
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 C17/H17 C18/H18 C19/H19 C20/H20 C21/H21 C22/H22 C23/H23 C24/H24
3 bDGlcp 101.6/3.40-3.54 74.9/3.40-3.54 78.3/3.40-3.54 71.2/3.40-3.54 78.4/3.40-3.54 62.5/3.40-3.54
Subst 162.6/6.64 156.3/6.74 158.6/3.76 145.1/3.40-3.54 138.6/5.54 183.4/3.89-3.91 105.3/1.84 157.0/4.07 61.3/5.21 125.1/1.67 135.6/1.83 14.0/5.08 27.1/3.40-3.54 124.9/3.40-3.5 132.0/3.40-3.54 26.0/3.72 18.3/3.89-3.91
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 | H17 | H18 | H19 | H20 | H21 | H22 | H23 | H24 |
|---|
| 3 | bDGlcp | 3.40
3.54 | 3.40
3.54 | 3.40
3.54 | 3.40
3.54 | 3.40
3.54 | 3.40
3.54 | |
| | Subst |
|
| 6.64 |
| 6.74 |
| 3.76 | 3.40
3.54 | 5.54 |
| 3.89
3.91 | 1.84 | 4.07 | 5.21 |
| 1.67 | 1.83 |
| 5.08 | 3.40
3.54 | 3.40
3.5 | 3.40
3.54 | 3.72 | 3.89
3.91 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 | C17 | C18 | C19 | C20 | C21 | C22 | C23 | C24 |
|---|
| 3 | bDGlcp | 101.6 | 74.9 | 78.3 | 71.2 | 78.4 | 62.5 | |
| | Subst | 161.1 | 112.8 | 162.6 | 93.4 | 156.3 | 102.8 | 158.6 | 145.1 | 138.6 | 112.2 | 183.4 | 105.3 | 157.0 | 61.3 | 22.0 | 125.1 | 135.6 | 69.1 | 14.0 | 27.1 | 124.9 | 132.0 | 26.0 | 18.3 |
|
There is only one chemically distinct structure:
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