Taxonomic group: plant / Streptophyta (Phylum: Streptophyta)
 
Publication DOI: 10.1248/cpb.43.338
Journal NLM ID: 0377775
Publisher: Pharmaceutical Society Of Japan
Institutions: Department of Botany, St. Xavier's College (Autonomous), Palayamkottai, India, Department of Chemistry, Manonmaniam Sundaranar University, Tirunelveli, India, Faculty of Pharmaceutical Sciences, Science University of Tokyo, Tokio, Japan

Three dihydroflavonol glycosides, 3-O-α-L-rhamnosides of (2S,3S)-, (2R,3R)- and (2R,3S)-5,7,3',4'-tetrahydroxydihydroflavonol, were isolated from Sphaerostephanos arbuscula as the first example of dihydroflavonols from ferns. Aglycone chirality was determined by 1H-NMR data.

1H-NMR, astilbin, Sphaerostephanos arbuscula, dihydroflavonol, chirality determination, fern

Structure type: oligomer
C₂₇H₃₀O₁₆
Location inside paper: p. 339, rutin
Trivial name: rutin, rutoside, rutin, quercetin rutinoside, rutoside, quercetin 3-O-rutinose, quercetin-3-O-rutinoside, quercetin 3-O-rutinoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
 
Methods: 13C NMR, 1H NMR, EI-MS, IR, acid hydrolysis, GLC, HPLC, UV, extraction, optical rotation measurement, CD, CC, melting point determination, precipitation, derivatization
 
Related record ID(s): 50488, 50489, 50490
NCBI Taxonomy refs (TaxIDs): 1521241
Reference(s) to other database(s): CCSD:50720, CBank-STR:3399
Show glycosyltransferases
 
NMR conditions: in DMSO-d6        [as TSV]

1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16 3,6 aLRhap 4.40 ? ? ? ? 1.00   3 bDGlcp 5.35 ? ? ? ? ?     xXQuercetin 6.20 6.39 6.85 ? ?

13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 3,6 aLRhap 100.7 70.4 70.0 71.8 68.2 17.7   3 bDGlcp 101.2 74.0 76.4 70.6 75.9 67.0     xXQuercetin 156.4 133.3 177.4 161.2 98.7 164.1 93.6 156.6 104.0 121.2 115.2 144.7 148.4 116.3 121.6

The spectrum also has 1 signal at unknown position (not plotted).

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