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1. (Article ID: 8875)
Elsbaey M, Sallam A, El-Metwally M, Nagata M, Tanaka C, Shimizu K, Miyamoto T
Melanogenesis inhibitors from the endophytic fungus Aspergillus amstelodami
Chemistry and Biodiversity 16(8) (2019)
ID e1900237
Two new compounds, named 3,4-dimethoxyphenyl α-D-ribofuranoside (1) and 3β-(β-D-glucopyranosyloxy)olean-12-ene-23,28,30-trioic acid (2), together with thirteen known compounds, were isolated from the white beans culture of the marine derived endophytic fungus Aspergillus amstelodami. Structure elucidation of the new compounds was carried out by one-, two-dimensional spectroscopy, and high resolution electrospray ionization mass. The antimelanogenic and anti-allergic activity of the isolated compounds were investigated. Compounds 4, 7, 1, 3, 11, 6 and 9 selectively suppressed melanin production in B16 melanoma cells, using arbutin as a positive control. Their IC50 values were 30.8±5.57, 38.5±6.08, 52.6±6.64, 98.0±1.16, 100.4±3.05, 112.0±0.22 and 144.7±2.35 μm, respectively, while that of arbutin was 151.7±1.27 μm. The tested compounds did not show any significant anti-allergic activity in RBL-2H3 cells, as compared to quercetin.
biological activity, 3, 4-dimethoxyphenyl α-D-ribofuranoside, 3β-(β-D-glucopyranosyloxy)olean-12-ene-23, 28, 30-trioic acid, Aspergillus amstelodami, B16 melanoma cells, β-hexosaminidase
NCBI PubMed ID: 31241824Publication DOI: 10.1002/cbdv.201900237Journal NLM ID: 101197449Publisher: Verlag Helvetica Chimica Acta
Correspondence: marwaelsebay1611
mans.edu.eg
Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt, Department of Natural Products Chemistry, Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan, Division of Marine Environment, National Institute of Oceanography and Fisheries, Hurghada, Egypt, Department of Agro-environmental Sciences, Graduate School of Bioresource and Bioenvironmental Science, Kyushu University, Fukuoka, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, IR, PCR, TLC, acid hydrolysis, HPLC, extraction, CC, cell growth, HR-ESI-MS, enzymatic assay, cell viability assay, cytotoxicity assay, MTT
The publication contains the following compound(s):
- Compound ID: 21919
|
a-D-Ribf-(1-4)-Subst1Me2Me
Subst = 2,4-dihydroxyphenol = SMILES O{4}C1=CC={1}C(O){2}C(O)=C1 |
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Structure type: monomer
; 309.1009 [M+Na]+
C13H18O7
Compound class: glycoside
- Compound ID: 21920
|
b-D-Glcp-(1-3)-Subst
Subst = 3β-hydroxy-olean-12-ene-23,28,30-trioic acid = SMILES C[C@]5({30}C(=O)O)CC[C@]4({28}C(=O)O)CC[C@]3(C)/C(=C\C[C@@H]2[C@@]1(C)CC{3}[C@H](O)[C@@](C)({23}C(=O)O)[C@@H]1CC[C@]23C)[C@@H]4C5 |
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Structure type: monomer
; 701.3600 [M+Na]+
C36H54O12
Compound class: glycoside
- Compound ID: 21921
|
b-D-Glcp-(1-3)-Subst
Subst = stigmasterol = SMILES CC[C@H](/C=C/[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC{3}[C@@H](C4)O)C)C)C(C)C |
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Structure type: monomer
Trivial name: stigmasterol 3-O-β-D-glucopyranoside
Compound class: saponin glycoside, glycoside, steroid glycoside, triterpenoid glycoside
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