Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Organ / tissue: leaves
The structure was elucidated in this paperPublication DOI: 10.1002/(SICI)1099-1573(199812)12:8<562::AID-PTR356>3.0.CO;2-6Journal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Núcleo de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Instituto de Microbiologia, Departamento de Virologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Instituto Biológico de São Paulo, Seção de Biologia Celular, São Paulo, Brazil
An infusion of Persea americana leaves (Lauraceae) strongly inhibited herpes simplex virus type 1 (HSV-1), Aujeszky's disease virus (ADV) and adeno virus type 3 (AD3) in cell cultures. Its fractionation, guided by anti-HSV-1 and ADV assays, allowed the isolation and identification of two new flavonol monoglycosides, kaempferol and quercetin 3-O-alpha-D-arabinopyranosides, along with the known kaempferol 3-O-alpha-L-rhamnopyranoside (afzelin), quercetin 3-O-alpha-L-rhamnopyranoside (quercitrin), quercetin 3-O-beta-glucopyranoside and quercetin, The known quercetin 3-O-beta-galactopyranoside was identified in a mixture. Afzelin and quercetin 3-O-alpha-D-arabinopyranoside showed higher activity against acyclovir-resistant HSV-I, Chlorogenic add significantly inhibited the HSV-1 replication without any cytotoxicity. However, all the substances tested were less active than the infusion or fractions. The same substances did not affect ADV replication. Chemical structures were elucidated by the analysis of UV, H-1 and C-13 NMR data, mainly by APT, homo and heteronuclear COSY experiments. The configuration of the D-arabinose unit, not usual in natural plant products, was established on the basis of the optical rotation of the free sugar obtained after acid hydrolysis.
quercetin, leaves, quercitrin, Persea americana, kaempferol 3-o-alpha-d-arabinopyranoside, quercetin 3-o-alpha-d-arabinopyranoside, afzelin, quercetin 3-o-beta-glucopyranoside, quercetin 3-o-beta-galactopyranoside, chlorogenic acid, herpes simplex virus type 1, aujeszky's disease virus, adenovirus type 3
Structure type: monomer
C
21H
20O
11Location inside paper: p. 564, column 1, paragraph 2 (compound 4)
Trivial name: quercitrin, baohuoside-II, quercetin 3-rhamnoside, quercetin 3-O-rhamnoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
Methods: 13C NMR, 1H NMR, TLC, acid hydrolysis, paper chromatography, UV, optical rotation measurement, CC, melting point determination, antiviral assay
Related record ID(s): 61147, 61148, 61151, 61152, 61490
NCBI Taxonomy refs (TaxIDs): 3435Reference(s) to other database(s): CCSD:
49971, CBank-STR:599
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
3 aLRhap 103.8 72.2 72.5 73.6 72.3 17.9
xXQuercetin - 159.6 136.5 179.9 163.5 100.2 166.4 95.1 158.9 106.1 123.3 117.2 146.7 150.1 116.7 123.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13 H14 H15 H16
3 aLRhap 5.54 4.40 3.92 3.70 3.70 1.15
xXQuercetin - - - - - 6.39 - 6.54 - - - 7.52 - - 7.10 7.47
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 aLRhap 103.8/5.54 72.2/4.40 72.5/3.92 73.6/3.70 72.3/3.70 17.9/1.15
xXQuercetin 100.2/6.39 95.1/6.54 117.2/7.52 116.7/7.10 123.2/7.47
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 | H13 | H14 | H15 | H16 |
|---|
| 3 | aLRhap | 5.54 | 4.40 | 3.92 | 3.70 | 3.70 | 1.15 | |
| | xXQuercetin |
|
|
|
|
| 6.39 |
| 6.54 |
|
|
| 7.52 |
|
| 7.10 | 7.47 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 | C13 | C14 | C15 | C16 |
|---|
| 3 | aLRhap | 103.8 | 72.2 | 72.5 | 73.6 | 72.3 | 17.9 | |
| | xXQuercetin |
| 159.6 | 136.5 | 179.9 | 163.5 | 100.2 | 166.4 | 95.1 | 158.9 | 106.1 | 123.3 | 117.2 | 146.7 | 150.1 | 116.7 | 123.2 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":103.8,"l":"1","c":[0,0,225]},{"s":72.2,"l":"2","c":[0,0,225]},{"s":72.5,"l":"3","c":[0,0,225]},{"s":73.6,"l":"4","c":[0,0,225]},{"s":72.3,"l":"5","c":[0,0,225]},{"s":17.9,"l":"6","c":[0,0,225]},{"s":159.6,"l":"2","c":[230,0,30]},{"s":136.5,"l":"3","c":[230,0,30]},{"s":179.9,"l":"4","c":[230,0,30]},{"s":163.5,"l":"5","c":[230,0,30]},{"s":100.2,"l":"6","c":[230,0,30]},{"s":166.4,"l":"7","c":[230,0,30]},{"s":95.1,"l":"8","c":[230,0,30]},{"s":158.9,"l":"9","c":[230,0,30]},{"s":106.1,"l":"10","c":[230,0,30]},{"s":123.3,"l":"11","c":[230,0,30]},{"s":117.2,"l":"12","c":[230,0,30]},{"s":146.7,"l":"13","c":[230,0,30]},{"s":150.1,"l":"14","c":[230,0,30]},{"s":116.7,"l":"15","c":[230,0,30]},{"s":123.2,"l":"16","c":[230,0,30]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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