Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: stem bark
NCBI PubMed ID: 10705503Publication DOI: 10.1248/cpb.48.194Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Institutions: College of Pharmacy, Chungnam National University, Taejeon, South Korea, Institute of Natural Medicine, Toyama Medical and Pharmaceutical University, Toyama, Japan
From the stem-bark of Juglans mandshurica, two new naphthalenyl glucopyranosides, 1, 4, 8-trihydroxy-nahthalene 1-O-[α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside] (1) and 1, 4, 8-trihydroxynaphthalene 1-O-β-D[6'-O-(3", 5"-dihydroxy-4"-methoxybenzoyl)]glucopyranoside (4), and two new α-tetralonyl glucopyranosides, 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-(3", 5"-dihydroxy-4"-methoxybenzoyl)glucopyranoside (7) and 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-(3", 4", 5"-trihydroxybenzoyl)glucopyranoside (8), were isolated together with three known naphthalenyl glucopyranosides (2, 3 and 5), one α-tetralonyl glucopyranoside (6), four flavonoids (9-12), and two gaalloyl glucopyranosides (13, 14).Amongst the isolated compounds, 1, 2, 6-trigalloylglucopyranose (13) and 1, 2, 3, 6-tertagalloylglucopyranose (14) exhibited the most potent inhibition of reverse transcriptase (RT) activity with IC50 values of 0.067 and 0.040 μM, respectively, while the latter compound also inhibited ribonuclease H (RNase H) activity with an IC50 of 39 μM, comparable in potency to illimaquinone used as a positive contorl. 1, 4, 8-Trihydroxy-naphthalene 1-O-β-D-glucopyranoside (2), 1, 4, 8-trihydroxynaphthalene 1-O-β-D-[6'-O-(4"-hydroxy-3", 5"-dimethoxybenzoyl)]glu-copyranoside (3) and 8 showed moderate inhibition against both enyzme activities, and inhibitory potency of 2 against RNase H activity (IC50=156 μM) was slightly greater than that against the RT activity (IC50=290 μM).The inhibitory potencies of 4α, 5, 8-trihydroxy-α-tetralone 5-O-β-D-[6'-O-4"-hydroxy-3", 5"-dimethoxybenzoyl)] glucopyranoside (6), 7 and 8 against RT activity increased accompanied by an increase in the number of free hydroxyls on the galloyl residues, as represented by the IC50 values of >500, 330 and 5.8 μM, respectively.
reverse transcriptase, Juglans mandshurica, human immunodeficienc virus, naphthalenyl glucopyranoside, ribonuclease H, α-tetralonyl glucopyranoside
Structure type: monomer
C
21H
20O
12Location inside paper: p. 195, Chart 1, structure 12
Trivial name: myricitrin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
Methods: biological assays
Related record ID(s): 66885, 66886, 66887, 66888, 66889, 66890, 66891, 66892, 66893, 66894, 66896, 66897
NCBI Taxonomy refs (TaxIDs): 91218Reference(s) to other database(s): CCSD:
49968, CBank-STR:384
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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